Winter Park FL Single Family Real Estate, Homes for Sale

3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 06 SubDv. ⋅ 32792 Zip Code

Discover the epitome of comfortable living in this fantastic single-family home situated on a generous and spacious corner lot. This meticulously renovated property features 3 bedrooms and 2 bathrooms, offering a perfect blend of modern style and cozy charm. Step inside to experience the allure of an open floor plan that seamlessly connects the living spaces. The kitchen, fully renovated and boasting a contemporary design, is the heart of this home—a perfect gathering place for family and friends. Indulge in the luxury of a private backyard oasis, where tranquility meets outdoor enjoyment. A delightful retreat awaits with a nice backyard, ideal for entertaining or simply unwinding under the stars. Plus, your vehicles and recreational gear are well taken care of with a 2-car garage and an additional boat space. The charm continues outdoors with a great covered lanai, providing the perfect setting for al fresco dining or cozy evenings by the fireplace. Every detail of this home has been thoughtfully curated to enhance your lifestyle. Don't miss the opportunity to make this Winter Park residence your own—where spacious living, thoughtful design, and comfort converge. Schedule your tour today and envision the possibilities that await in this truly remarkable home!

1886 Clematis Lane, Winter Park

$429,000

4 Beds ⋅ 2 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code

Rare opportunity in Winter Park's 32789! Located on a quiet cul-de-sac in one of Central Florida's most sought-after ZIP codes, this spacious 4-bedroom, 2-bath home offers approximately 2,400 square feet of living space, a brand new roof (2025), water heater (2021), and is situated on a generous lot with no HOA. Whether you're dreaming of creating your forever home, searching for your next renovation project, or looking to add a prime rental property to your portfolio, this is one you won't want to miss. With a little vision and updating, this property can truly shine in a neighborhood where beautifully renovated homes and stunning new construction continue to elevate property values. The location is exceptional—minutes from Park Avenue, Winter Park Village, top-rated schools, Rollins College, AdventHealth, downtown Orlando, and convenient access to I-4 and SR 408. Enjoy some of Central Florida's finest dining, boutique shopping, parks, museums, and entertainment, all just moments from your doorstep. Families will also appreciate Killarney Elementary School is just one street away. With endless possibilities to reimagine, renovate, or invest, opportunities to purchase a home like this seldom come along. If you're looking to build equity, generate rental income, or create the home you've always envisioned, this exceptional property is ready for its next chapter.

2323 Devon Court, Winter Park

$1,419,900

4 Beds ⋅ 4 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code

Under Construction. Under Construction. NEW CONSTRUCTION!!! Welcome to Winter Park Grove — Winter Park’s newest community by one of the areas finest builders. This stunning new farmhouse-inspired home is designed to impress with its architectural flair, meticulous craftsmanship, and luxurious finishes. Perfectly located near all the shopping, dining, and entertainment Winter Park is famous for, this home combines convenience, style, and comfort. Step onto the inviting front porch and through the elegant 2 story entryway to discover a spacious, open floor plan filled with natural light. Just off the foyer, you’ll find a flexible fourth bedroom or private study with a full bath—ideal for a home office or serene guest suite. The heart of the home is the gourmet kitchen, featuring quartz countertops, custom cabinetry, and a premium Bosch appliance package including a 36" gas cooktop. The kitchen flows seamlessly into the living and dining areas—perfect for entertaining or family gatherings. Enjoy Florida living at its finest on the covered lanai, overlooking your sparkling pool and lushly landscaped backyard—your own private retreat. The first-floor primary suite offers a spa-inspired bath with dual vanities, a freestanding soaking tub, and a spacious walk-in closet with custom shelving. A convenient laundry area is thoughtfully located just off the suite. Upstairs, a large bonus room with a closet offers versatility as a fifth bedroom, game room, or home office. Two additional bedrooms feature walk-in closets and share a beautifully appointed bath with dual sinks. An upstairs laundry room with a sink and plenty of natural light adds everyday convenience. The photos shown are of the same model in another location. Finishes will vary. Located near top-rated schools, local parks, and all that Winter Park has to offer — this home truly has it all. Schedule your private showing today before this exceptional new build is gone!

1546 Miller Avenue, Winter Park

$430,000

3 Beds ⋅ 2 Baths ⋅ Howell Branch Woods SubDv. ⋅ 32792 Zip Code

Virtually Staged. Discover this spacious 3-bedroom, 2-bathroom home offers 1,483 sq ft of comfortable living space with a functional layout and plenty of room for everyday living. The home features a well-appointed kitchen, open living areas, and generously sized bedrooms. Outside, enjoy a private backyard with a swimming pool, creating the perfect space for relaxing, entertaining, and enjoying the Florida lifestyle.

5409 Albert Drive, Winter Park

$339,000

3 Beds ⋅ 2 Baths ⋅ Eastbrook Subd Unit No 05 SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully updated 3-bedroom, 2-bath home in beautiful Winter Park! This move-in-ready property features stylish wood-look tile flooring throughout, creating a seamless, modern look that's both attractive and easy to maintain. The home has two beautifully renovated bathrooms with contemporary finishes, along with a newer A/C and a new roof in 2026. The air-conditioned laundry room has plenty of storage space. Step outside to your spacious, fully fenced backyard, where you'll find plenty of room to entertain, play, or unwind around the cozy fire pit. The generous outdoor space offers endless possibilities for gatherings, gardening, or simply enjoying Florida's beautiful weather. A rare highlight is the oversized swing gate providing convenient side-yard access with ample room to park an RV, boat, trailer, or other recreational vehicles. Best of all, there's no HOA, giving you the freedom to make the most of your property without additional HOA restrictions. Perfectly situated just minutes from Costco, grocery stores, shopping, dining, and the popular Cady Way Trail, this home offers the ideal combination of comfort, convenience, and outdoor recreation. With easy access to major roadways and everything Winter Park has to offer, this home truly has it all. Welcome home!

3562 Bougainvillea Drive, Winter Park

$795,000

3 Beds ⋅ 2 Baths ⋅ Lakeview Terrace SubDv. ⋅ 32789 Zip Code

This well-cared-for immaculate home features quality workmanship inside and out! The mature tropical oasis landscaping, cozy seating areas, and winding pathways make you feel right at home and at the same time on vacation! Open Kitchen, dining room, living room and bonus room. Located on a quaint street nestled among custom built homes. Have the best of both worlds, family life with upscale restaurants and shopping, and the annual Art and Holiday Festivals, movies in the park, parades, Rollins College, Boat Tours, kayaking and paddleboarding on the Winter Park Chain of Lakes all linked together and easily accessed via an Italian-inspired canal system. Only a mile away from famous ‘Park Avenue’ where visitors travel from all over the world to experience and celebrate our romantic sidewalk cafés and festivities.

1850 Bryan Avenue, Winter Park

$324,900

3 Beds ⋅ 2 Baths ⋅ Woodcrest Unit 03 SubDv. ⋅ 32792 Zip Code

Virtually Staged. Opportunity Awaits in the Heart of Winter Park! Welcome to 7426 Blue Jacket Place, a 3-bedroom, 2-bathroom home that's ready for its next chapter. Nestled on a quiet street in an established neighborhood, this property offers a fantastic opportunity for buyers looking to add their personal touch and create the home of their dreams. Plus, enjoy added peace of mind knowing the roof was replaced approximately six years ago. Inside, you'll find a spacious layout featuring a large living area, a functional kitchen with an adjoining dining space, and generously sized bedrooms. The screened-in porch is the perfect place to relax and enjoy the peaceful backyard. Step outside and discover one of this home's standout features—a beautiful, mature camphor tree that creates a picturesque backyard retreat with plenty of shade and room to garden, entertain, or simply unwind. The property also includes a storage shed, ample outdoor space for endless possibilities, and an existing 25-foot-deep well on the property, offering potential for future use. Conveniently located near shopping, dining, major roadways, parks, and all the highly sought-after Winter Park amenities, this home offers an unbeatable location with tremendous potential. Whether you're a first-time homebuyer, investor, or someone looking for a renovation project, this is an opportunity you won't want to miss. Bring your vision and make 7426 Blue Jacket Place your own!

7426 Blue Jacket Place E, Winter Park

$2,275,000

4 Beds ⋅ 5 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

This WINTER PARK POOL HOME is set on a corner lot with entrances from both Palmer Avenue and Temple Drive. Located within Winter Park's exclusive J Kronenberger community, this luxury property is tucked away approximately a half mile to Winter Park's YMCA, Phelps Park & the lovely Kraft Azalea Garden, and approximately 1.5 miles to Park Avenue's restaurants, boutiques and farmer's market. The floor plan offers 4 bedrooms, 4.5 bathrooms & a home office/bonus room. The bedrooms are organized in a triple split plan arrangement that frames the open-concept gathering areas. Three bedrooms have private ensuite bathrooms, the 4th bedroom is placed directly next to the hall bath, and the office/bonus room sits adjacent to the guest half bath...everyone has a bathroom! Multiple exits lead out to the backyard, seamlessly merging the indoor and outdoor spaces. Mature hedges provide natural privacy for the open-air pool, spacious pool deck and backyard lawn. Additionally, a backyard paver path provides access to the property's 2-car detached garage. There is plenty of parking for year-round entertaining with the front half circle drive and the rear 2-car garage with multi-car driveway. This home uses natural gas to fuel the range, tankless water heater and outdoor firepit on the pool deck. Recent updates include outdoor perimeter lighting, rear fence, privacy hedges & irrigation. Prime real estate within Winter Park’s historic tree-lined streets.

1271 Palmer Avenue, Winter Park

$469,000

3 Beds ⋅ 2 Baths ⋅ Casa Aloma SubDv. ⋅ 32792 Zip Code

Okay, let's talk about this one. Yes, there's green carpet. Yes, it needs your vision. I know exactly what you're thinking right now. But hear me out, because this house has some things going for it that are genuinely hard to find. Start with the location. In under 10 minutes in any direction, you could be having lunch on Park Ave, shopping at Altamonte Mall, or launching your boat up in Maitland. That kind of range is rare in Central Florida, and this spot has it. And there's no HOA here, which if you know, you know. Then there's the pool. A real pool, tucked behind a block wall for total privacy, so you can actually enjoy it without the whole street watching. That kind of setup doesn't come around often. This is a 3 bedroom, 2 bath home with real bones and real space. The layout gives you room to breathe, and the systems that actually matter have already been taken care of. Water heater, brand new in 2026. HVAC, also brand new in 2026. Roof was done in 2025. Plumbing was updated in 2017. So the expensive, unglamorous stuff, the stuff that actually protects your investment, is already handled. The home has been professionally cleaned and pressure washed, so it's not just clean, it's move in ready clean. You could genuinely move in as is and update it slowly, on your own timeline, as your taste and budget allow. No rush. No pressure. Just a solid home with good bones, a pool, an unbeatable location, and all the boring but important stuff already done for you. Sometimes the right house isn't the one that's already finished. It's the one that's ready for you to finish it.

2703 Tierra Circle, Winter Park

$1,375,000

1 Beds ⋅ 1 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Versatile Live/Work (0-1) zoned parcel in Winter Park's prestigious 32789 ZIP code. This 0.43-acre lot offers flexibility for residential, office, or mixed-use development. Part of a four-lot portfolio that includes three direct lakefront parcels on Lake Killarney - available together or individually. Steps from Winter Park Village, Park Avenue, and Rollins College.

1298 Beachview Avenue, Winter Park

$684,000

4 Beds ⋅ 2 Baths ⋅ Winter Park Pines Rep SubDv. ⋅ 32792 Zip Code

Virtually Staged. Welcome to a residence where timeless design meets modern sophistication in the highly sought-after Winter Park Pines community—one of Winter Park's most established neighborhoods, celebrated for its tree-lined streets, oversized homesites, exceptional schools, and proximity to world-class dining, shopping, golf, and cultural attractions. With no HOA, this thoughtfully renovated home offers the perfect balance of refined living and everyday comfort in one of Central Florida's most desirable locations. This 1,605 sqft, 4-bedroom, 2-bath residence, has been transformed with modern finishes, upgraded systems, and thoughtful design throughout. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a bright and inviting space ideal for both everyday living and entertaining. The interior features new luxury vinyl flooring in all main areas and fully remodeled bathrooms with floor and wall tile, elongated modern toilets, updated vanities, and premium finishes. The main bathroom includes a new bathtub, medicine cabinet, and mirror cabinet, while the master bathroom offers a glass-walled shower with a niche and a double floating vanity with mirrored cabinets. The kitchen is a true centerpiece, showcasing a large island, quartz countertops, high-end custom cabinetry with soft-close drawers, and a pantry with built-in shelving. Luxury FORNO white-and-gold appliances elevate the space, including an induction cooktop and range, hood fan, double-door refrigerator with ice maker, and a microwave built into an island drawer. The kitchen is completed with a high-end white sink bowl and garbage disposal, adding both style and functionality. Major improvements were completed with permits, including new HVAC (2026), new water heater (2026), new 200 Amps electrical panel (2026), and a full plumbing repipe (2026). Additional upgrades include new wired smoke alarms and new doors throughout. The living room features modern potlights, and all bedrooms include contemporary ceiling fans. The lanai has been renovated, offering a comfortable outdoor retreat. Exterior enhancements include an updated roof (2020), fresh interior and exterior paint, a refinished garage floor, and an upgraded garage door opener (2026). The property also features a brand-new irrigation system (2026) to keep the grounds lush and easy to maintain. Smart-home additions include a smart Blink doorbell and a smart front-door lock, providing added convenience and security. The spacious, fully-fenced backyard offers privacy and endless possibilities for outdoor enjoyment, gardening, or future enhancements. Perfectly positioned just minutes from Winter Park Pines Golf Club, Cady Way Trail, Park Avenue, Rollins College, AdventHealth Winter Park, and the boutiques, fine dining, and cafés that have made Winter Park one of Central Florida's most coveted destinations, you'll also enjoy convenient access to Downtown Orlando, Baldwin Park, major highways, Orlando International Airport, and countless entertainment venues. With meticulous renovations, modern systems, smart-home upgrades, and an unbeatable Winter Park Pines location, this home is truly move-in ready and prepared to welcome its next owner.

2833 Prince John Road, Winter Park

$362,000

3 Beds ⋅ 2 Baths ⋅ Wrenwood Unit 3 2nd Add SubDv. ⋅ 32792 Zip Code

Virtually Staged. Imagine 7026 Hammock Way, recently enhanced with fresh interior paint throughout, establishing a bright and inviting atmosphere. The outdoor space includes a covered patio for outdoor enjoyment, extending to a fully fenced in backyard, providing defined outdoor boundaries. A perfect blend of fresh updates and functional outdoor living awaits.. Included 100-Day Home Warranty with buyer activation

7026 Hammock Way, Winter Park

$365,000

3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 8 SubDv. ⋅ 32792 Zip Code

Don't miss this opportunity to own a beautifully updated home with a sought-after Winter Park address! Priced to sell, this move-in-ready 3-bedroom, 2-bath home offers the perfect combination of comfort, style, and location. Enjoy being just minutes from Park Avenue, Baldwin Park, Cady Way Park and Trail, Winter Pines Golf Club, shopping, restaurants, and major roadways, making it easy to enjoy everything Winter Park and the surrounding area have to offer. Inside, you'll love the open floor plan that's perfect for everyday living and entertaining. The updated kitchen features quartz countertops, stainless steel appliances, a large single-basin sink, beautiful cabinetry, and plenty of counter space. It opens to the spacious dining area and family room, creating a bright and welcoming space where everyone can gather. Tile flooring is featured in the foyer, kitchen, bathrooms, and the large open living area just off the kitchen, while warm wood flooring flows through the formal dining room, family room, hallway, and all three bedrooms for a clean, updated look. The primary suite offers a spacious closet and an oversized walk-in shower designed for comfort and convenience. Step outside to the oversized screened lanai overlooking a fully fenced backyard that's perfect for entertaining, pets, play, or simply relaxing after a long day. A large storage shed provides plenty of room for lawn equipment, tools, bikes, or seasonal storage. Recent updates include a 2021 roof and 2022 HVAC system, giving the next owner added peace of mind. Security bars on the windows provide an extra layer of protection and may qualify for insurance discounts. If you've been looking for an updated home in Winter Park that offers great value, this is one you won't want to miss!

2511 Eastbrook Boulevard, Winter Park

$6,700,000

4 Beds ⋅ 3 Baths ⋅ Osceola Shores Sec 03 SubDv. ⋅ 32789 Zip Code

Stunning Custom Estate on the Shores of Lake Osceola

405 Lakewood Drive, Winter Park

$1,800,000

5 Beds ⋅ 5 Baths ⋅ Osceola Shores Sec 02 SubDv. ⋅ 32789 Zip Code

Short Sale. Welcome to this luxury, home in the heart of Winter Park. Less than a mile away from Park Ave. Winter Park that offers entertainment, restaurants, farmers market and so much more. A beautiful contemporary style home with modern interior finishes. Featuring an open floor plan, 5 bedrooms, 4.5 baths, a loft/flex space, media room, 2 study areas, front porch, back patio, lanai and so much more. Corner lot and privacy. Engineered hard wood floors through out the house and tile in utility rooms. 2 laundry rooms for convenience, located on 1st and 2nd floor of the home. Private backyard setting, a very large pool, an outdoor entertainment area featuring a kitchen and a fireplace and a screened in lanai. Metal Roof with Solar panels. A gas stove with large island and lots of space for entertainment. This home has a lot to offer in the most desirable location. Schedule your showing today.

281 Brewer Avenue, Winter Park

$624,900

4 Beds ⋅ 2 Baths ⋅ Shores Lake Killarney SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Completely updated and move-in ready, this stunning Winter Park home offers the perfect blend of timeless charm and modern comfort! Located in the desirable Shores of Lake Killarney, this 4-bedroom, 2-bath home features 1,933 square feet of thoughtfully updated living space, deeded access to Lake Killarney, and NO HOA! As you step inside, an open layout creates a seamless flow between the kitchen, dining, and living area. The updated kitchen features quartz countertops, stainless steel appliances, generous cabinetry, an island with breakfast bar, and dining area. Sliding doors off the living area open to a private, fully fenced backyard! Whether you're enjoying a quiet morning coffee or hosting outdoor gatherings, this large, inviting space provides the perfect extension of the home's living space! Enjoy peace of mind knowing the major updates have already been completed, including a new roof (2023), new A/C and hot water heater (2025), new windows (2024), complete re-pipe (2021), new electrical panel (2021), and many additional improvements throughout the home. Conveniently located near Winter Park Village, Park Avenue, Rollins College, top-rated dining, shopping, entertainment, and major roadways, this location puts the best of Winter Park and Greater Orlando within easy reach. This is the perfect opportunity to own a move-in-ready Winter Park home that offers the character of an established neighborhood with the peace of mind and convenience of modern updates. Call to set up a private showing today!

216 Blossom Lane, Winter Park

$280,000

3 Beds ⋅ 2 Baths ⋅ Coronation Add SubDv. ⋅ 32792 Zip Code

Turnkey Charm in Winter Park! This beautifully remodeled 3-bedroom, 2-bathroom home offers the perfect blend of style and convenience. Step inside to find durable ceramic tile flooring flowing through a spacious family room, perfect for entertaining. The home features a 1-car garage with a functional laundry area equipped with a washer and dryer tucked neatly in the back, alongside a fantastic outdoor setup. Relax on your open, screened-in patio overlooking a massive, fully fenced backyard. Freshly updated inside and out, this move-in-ready gem is ready for its next owner!

3321 Royal Street, Winter Park

$409,900

3 Beds ⋅ 2 Baths ⋅ Justamere Camp Rep SubDv. ⋅ 32789 Zip Code

Virtually Staged. Conveniently located just minutes from I-4, downtown Orlando, and Winter Park, this versatile home offers the perfect blend of comfort, flexibility, and location. The upper level features two bedrooms and one full bath, while the lower level includes one bedroom and one full bath. Each floor has its own private entrance and full kitchen, making it ideal for multi-generational living, rental income, a guest suite, or added privacy. Situated on a beautiful, tree-lined dead-end street, the property offers a peaceful setting while remaining close to shopping, dining, and entertainment. Inside, you'll find contemporary fixtures, stylish finishes, updated appliances, and an abundance of natural light throughout. The spacious backyard and inviting seating area provide the perfect space to relax or entertain family and friends. Major updates include a recently replaced roof, HVAC system, and electrical panel, offering added peace of mind. Some photos have been virtually staged to help showcase the home's layout and potential.

2568 Lotafun Avenue, Winter Park

$1,275,000

3 Beds ⋅ 3 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

Virtually Staged. Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just minutes from Park Avenue, Winter Park Village, Rollins College and downtown Orlando, you'll enjoy the perfect balance of lake life, tranquility and accessible convenience. Experience award-winning dining, boutique shopping, entertainment, cultural attractions and everyday conveniences just moments from your future home. Priced to encourage redevelopment, this property is adjacent to 230 Killarney Drive, creating a rare opportunity to purchase one or both parcels. Together, they form an extraordinary double-lot assemblage with expansive views of Lake Killarney and endless possibilities to design a landmark residence. Whether purchased individually or together, opportunities to own on Lake Killarney are exceptionally limited. Build the custom home you've envisioned while enjoying one of Winter Park's most coveted locations from this desirable homesite with private lake access and the ability to build your own dock.

240 Killarney Drive, Winter Park

$1,250,000

4 Beds ⋅ 1 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just minutes from Park Avenue, Winter Park Village, Rollins College and downtown Orlando, you'll enjoy the perfect balance of lake life, tranquility and accessible convenience. Experience award-winning dining, boutique shopping, entertainment, cultural attractions and everyday conveniences just moments from your future home. Priced to encourage redevelopment, this property is adjacent to 240 Killarney Drive, creating a rare opportunity to purchase one or both parcels. Together, they form an extraordinary double-lot assemblage with expansive views of Lake Killarney and endless possibilities to design a landmark residence. Whether purchased individually or together, opportunities to own on Lake Killarney are exceptionally limited. Build the custom home you've envisioned while enjoying one of Winter Park's most coveted locations from this desirable corner homesite with private lake access and the ability to build your own dock.

230 Killarney Drive, Winter Park

$920,000

4 Beds ⋅ 3 Baths ⋅ Lakeside Estates SubDv. ⋅ 32792 Zip Code

Experience refined Florida living in this exceptional single-story residence, ideally situated on a quiet cul-de-sac within an intimate gated community in one of Winter Park's most desirable locations. Impeccably maintained, this elegant home offers over 3,000 square feet of thoughtfully designed living space with 4 bedrooms, 3 full baths, a private office, and a desirable three-way split floor plan that provides both privacy and flexibility. Designed for comfortable everyday living and effortless entertaining, the home features formal living and dining rooms, a spacious family room, and a bright breakfast area. The stunning gourmet kitchen is the heart of the home, showcasing timeless white cabinetry, quartz countertops, abundant prep space, a convenient butler's pantry, and an open flow to the main living areas. The generous primary suite offers a spacious walk-in closet and a luxurious retreat, while quality finishes and meticulous attention to detail are evident throughout. Enjoy year-round outdoor living on the private screened lanai, perfect for relaxing or entertaining. Additional highlights include a three-car garage, a durable tile roof, and a fully paid solar energy system, keeping the average monthly electric bill under $100. Combining elegance, energy efficiency, and an outstanding location, this move-in-ready home offers the perfect balance of luxury, comfort, and convenience.

1492 Via Sangro Pl, Winter Park

$449,000

3 Beds ⋅ 2 Baths ⋅ Hyde Park SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. Tucked away on a peaceful cul-de-sac, this beautifully updated Winter Park gem offers the perfect blend of modern style, functional design, and peace of mind. From the moment you arrive, the quiet setting welcomes you home to 1456 E. Brookshire Court. Step inside to discover a bright and airy interior featuring soaring vaulted ceilings that elevate the main living areas, creating a spacious and grand atmosphere. The thoughtfully designed split floor plan ensures maximum privacy, separating the serene primary suite from the additional bedrooms. Throughout the home, tasteful interior upgrades provide a sleek, move-in-ready aesthetic. Major highlights include brand new roof installed in 2020 for years of low-maintenance ownership. Enjoy the outdoor oasis out back complete with paver patio overlooking an expansive, deep backyard—perfect for weekend barbecues, play, or designing your dream pool. Zoned for highly sought-after Seminole County Public Schools while offering easy access to local dining, shopping, and parks. Don't miss the opportunity to own this turn-key retreat in a prime Winter Park location. Schedule your private showing today

1456 E Brookshire Court, Winter Park

$310,000

2 Beds ⋅ 1 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code

Roof 2018 | HVAC 2020| Set on a deep, tree-canopied lot in one of Winter Park's most desirable established neighborhoods, this charming single-story concrete-block home blends timeless character with everyday convenience. A grand oak shades the front lawn, helping cool the home and lower energy costs, while durable masonry construction, a dimensional-shingle roof, and a full-length driveway leading to a covered carport deliver lasting value and practical, protected parking with an attached workshop & storage room. A generous screened front porch offers a breezy, bug-free spot for morning coffee or evening relaxation before you step inside to a spacious living room featuring gleaming refinished hardwood floors and a wood-burning fireplace framed by a classic white mantel with fluted columns. A large picture window floods the room with natural light, and a graceful curved archway, one of the home's most distinctive architectural details, leads you deeper into the thoughtfully connected floor plan. The kitchen is efficiently designed with cabinetry lining both walls for ample storage, laminate counters, under-cabinet lighting, and a full stainless-steel appliance suite. A double sink offers plenty of room to work and a large window overlooks the lush backyard, with a rear door providing easy access for grilling and entertaining. The adjacent, light-filled dining room offers flexible space that works well for family meals, a home office, or a quiet reading nook. Two comfortable bedrooms feature hardwood floors, ceiling fans with lights, and built-in closets, one with built-in shelving, while the bright corner primary enjoys windows on two walls for excellent light and cross-ventilation. A full bathroom is finished with a tiled tub-and-shower combination, a wood vanity, and a frosted privacy window that brings in daylight while maintaining seclusion. Out back, a large, fully fenced yard framed by mature oaks, palms, and established privacy hedges creates a secluded, park-like retreat with ample room to garden, play, entertain, or add a pool. Just minutes from historic Park Avenue, residents enjoy boutique shopping, award-winning restaurants, sidewalk cafés, museums, and year-round community events, with nearby College Park adding popular dining, breweries, and specialty shops. Outdoor recreation abounds with Dubsdread Golf Course, Mead Botanical Garden, Kraft Azalea Garden, and numerous parks close by, plus easy access to Winter Park's scenic chain of lakes and walking trails, all without requiring waterfront ownership. Commuting is effortless thanks to convenient access to Interstate 4, Fairbanks Avenue, Lee Road, SR 426, and SR 436, providing quick connections throughout Central Florida. Downtown Orlando, the Orlando Health and AdventHealth medical campuses, and major employment centers are all within easy reach. With excellent shopping, grocery stores, entertainment, and cultural attractions nearby, this sought-after location offers the perfect balance of quiet residential living and close proximity to everything Central Florida has to offer. This listing is for a single home and lot at 846 Driver Ave, but the owner would also consider selling the adjacent home next door to the North at 844 Driver Ave. If you are interested in purchasing both homes simultaneously, contact listing agent for more details.

846 Driver Avenue, Winter Park

$1,150,000

4 Beds ⋅ 3 Baths ⋅ Lake Knowles Terrace 2nd Add SubDv. ⋅ 32789 Zip Code

Located on one of Winter Park's picturesque brick streets in the highly desirable “Tree Streets”, this beautifully updated home offers incredible curb appeal with a circular driveway, charming front porch with brick flooring, and mature landscaping. Inside, a spacious foyer with soaring ceilings welcomes you, while engineered hardwood flooring runs throughout the main living areas. The recently renovated kitchen is the heart of the home, featuring quartz countertops, custom oak cabinetry with gold hardware, a center island with seating, stylish backsplash, and stainless steel appliances, including a gas range. The kitchen opens to the spacious dining room and inviting family room with built-ins, high ceilings, and French doors that fill the space with natural light. One of the home's most unique features is its thoughtfully designed layout. The original 1951 portion of the home offers two bedrooms, including the original primary suite with a large walk-in closet and private bath, plus a beautifully renovated hall bathroom. An addition completed in the early 2000s created an impressive owner's retreat on the opposite side of the home, complete with vaulted ceilings, French doors to the backyard, an oversized walk-in closet with custom organization, and a spacious bathroom with double vanities, soaking tub, separate shower, and private water closet. A fourth bedroom, tucked away in its own wing off the dining room, features built-ins, a large walk-in closet, and is conveniently located near the indoor laundry room. Situated on a generous .24-acre lot, the backyard offers plenty of room to add a pool while still leaving space to enjoy the yard. A long driveway leads to the rear one-car carport and an oversized storage room. Major updates include a 2020 roof and 2021 AC. All of this is just minutes from Park Avenue's renowned shopping, dining, and events, with easy access to top-rated Winter Park schools, parks, and everything that makes this neighborhood one of Central Florida's most sought-after places to call home.

1351 Oneco Avenue, Winter Park

$779,000

3 Beds ⋅ 3 Baths ⋅ South Lakemont Shores SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Rare Winter Park gem, nestled between Lake Baldwin and the heart of Winter Park. This fully refreshed, single-story home features brand-new interior and exterior paint, complemented by newly refreshed landscaping. Offering 3 bedrooms and 3 full bathrooms, the highly desirable split floor plan includes two primary suites. The main primary suite boasts an updated shower, vanity, and a spacious walk-in closet. The second suite features a garden tub with shower and its own walk-in closet. The updated kitchen is equipped with floor-to-ceiling cabinets for ample storage and a custom built-in kitchen nook with bench seating. Additional highlights include a cozy fireplace, laminate flooring, plantation shutters, an air-conditioned laundry room, and an incredible oversized 3-car garage. Enjoy Florida’s outdoor living year-round with a screened porch and a spacious, fully fenced backyard. Superb location under a half-mile to Baldwin Park, 2.5 miles to Park Avenue, and 3 miles to Rollins College. Zoned for highly rated Winter Park schools and situated just moments from the Lake Baldwin dog park.

1871 Barker Drive, Winter Park

$820,000

4 Beds ⋅ 3 Baths ⋅ Golfside Sec 2 SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. **Due to the interest in the property, offers need to be in by Monday evening (7/20). ** Perfectly positioned on the 6th tee and 8th hole of the Winter Park Pines Golf Course, this home sits on an oversized quarter-acre lot and offers a rare opportunity to create your dream home while enjoying breathtaking golf course views. **The current floor plan features three bedrooms, as the original fourth bedroom has been converted into an expansive walk-in closet for the primary suite, and the flexible layout also offers the potential for a fifth bedroom.** While the interior offers an exciting opportunity to update, the sellers have already completed nearly $190,000 in major infrastructure and system improvements. One of the home's most valuable features is the fully paid-off solar panel system, which generates excess electricity that is returned to the utility company, resulting in an average monthly electric bill over 12 months is approximately $90. Additional capital improvements include a newer roof (2021), a new high-efficiency, variable-speed Lennox HVAC system (2025), a new energy-efficient, heat-pump water heater (2025), complete home repipe (2020), restoration of the cast-iron sewer system (2022) and plumbing stacks, upgraded attic insulation for enhanced energy efficiency (2023), a newer pool heater and pump (2024), added French drains (2025), new gutters with leaf guards, a deep irrigation well, an expanded circular paver driveway for ample parking space, and much more. Inside, the flexible floor plan offers endless possibilities. Beyond the spacious, front-facing living/dining room, the kitchen opens to a comfortable family room with a wood-burning fireplace. The kitchen window and pocket sliding glass doors frame beautiful views of the expansive covered lanai, screened pool, and rolling fairways beyond. The current 3-bedroom/2-bath layout on the left side can easily be reconfigured to restore the original 4th bedroom, which now serves as an oversized walk-in closet for the primary suite. The corner bedroom functions as both a guest room and home office, featuring a custom Murphy bed concealed behind a built-in bookcase, providing exceptional flexibility. On the opposite side of the home, an enormous bonus room with a full bath, offers direct pool access, and sweeping golf course views. Whether envisioned as a private guest suite or 5th bedroom, recreation room, home office, fitness studio, media room, or multigenerational living space, the bonus room has endless possibilities. Located just a few doors from the Cady Way Trail on one of the neighborhood's most picturesque oak-canopied streets, the setting is truly exceptional. This is a rare opportunity to purchase a home set directly on one of Winter Park's premier golf courses, where major mechanical system upgrades and costly infrastructure improvements have already been completed, creating the perfect opportunity to transform the interior into your own custom vision. Move in today, enjoy the exceptional location, and renovate at your own pace! Be sure to request a complete list of improvements, along with the floor plan, to fully appreciate the incredible potential this home presents.

938 Golfside Drive, Winter Park

$775,000

4 Beds ⋅ 3 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code

Welcome to 1562 Arbor Park Drive, a beautifully maintained four-bedroom, two-and-a-half-bath residence tucked along a charming brick street in the heart of Winter Park. This move-in-ready home combines elevated finishes, abundant natural light, a flexible split-bedroom floor plan, and an exceptional location near the shopping, dining, and cultural attractions that make Winter Park one of Central Florida’s most desirable communities. At the center of the home is a completely redesigned kitchen that is both stylish and highly functional. New cabinetry, quartz countertops, stainless steel appliances, generous storage, and an oversized island with bar seating create an inviting setting for everyday meals and entertaining. A beautiful picture window frames views of the lush backyard and fills the kitchen with natural light. The open living spaces flow seamlessly together over wood-look tile flooring, while fresh interior paint, updated fixtures, and an electric fireplace add warmth and a polished contemporary feel. Privately positioned on one side of the home, the expansive primary suite feels like a retreat of its own. The suite includes a custom designed walk-in closet and a beautifully designed bathroom with separate vanities, a freestanding soaking tub, an oversized walk-in shower, and a private water closet. Three additional bedrooms are located on the opposite side of the home, providing separation and flexibility for family members or overnight guests. The outdoor setting is equally impressive. The enormous, fully fenced backyard has been lovingly maintained and features mature greenery, privacy, and plenty of room for entertaining, recreation, gardening, pets, or a future outdoor living retreat. Bonus: there is additional parking on the west side of the home that is accessible from the backyard - perfect for hosting or entertaining! A cobblestone driveway enhances the home’s curb appeal, while notable improvements include replacement of the HVAC system and ductwork in 2016, numerous plumbing updates, and extensive interior renovations. Enjoy a location that places the best of Winter Park within easy reach. The home is conveniently located near the Winter Park YMCA, Lakemont Elementary School, Phelps Park, Rollins College, and the Winter Park Chain of Lakes - not to mention all of the boutiques, restaurants, museums, & cafés, and community events of historic Park Avenue. Baldwin Park, Winter Park Village, and Audubon Park are also just minutes away, offering even more options for dining, shopping, entertainment, and outdoor recreation. This is an exceptional opportunity to enjoy a gorgeous, fully updated home in the highly desirable in-town Winter Park address. Schedule your private showing and experience the lifestyle, location, and thoughtful design of 1562 Arbor Park Drive.

1562 Arbor Park Drive, Winter Park

$630,000

3 Beds ⋅ 2 Baths ⋅ Brookshire Heights 2nd Add SubDv. ⋅ 32792 Zip Code

RARE TWO-OWNER MID-CENTURY MODERN HOME IN WINTER PARK PROPER!! You will fall in love as the canopy of trees along Forfarshire Drive leads you to the door of this desirable Winter Park address. A fresh exterior re-envisioning brings a modern curb appeal, complete with a beautifully tiled covered front porch, glass entry door, Zen fountain and low architectural awnings provide an immediate sense of style and anticipation of what awaits inside the home. Upon entry, a large open living area with over-sized picture window and a stylish dining area, adorned with Brazilian hardwood flooring create a relaxed living experience. Updated kitchen includes white cabinetry (undermount counter lighting), Sile Stone countertops with undermount sink, stainless fridge & dishwasher and brush nickel hardware finishes. A large rear bonus room with storage closet space (designer built-ins) and oversized slider door leads to fenced and private backyard, the perfect retreat to relax and unwind. This wide-shoulder split floorplan offers a left-side primary bedroom with hardwood flooring and a large en suite office with access door to backyard, all wrapped windows with sophisticated Plantation shutters. The right side guest wing includes two large bedrooms flanking a remodeled full guest bathroom. KEY UPDATES INCLUDE: Architectural Shingle Roof (2016), Double Pane Windows (throughout), Knockdown Ceilings, Recessed LED Lighting & Touch Control Switches, PEX Plumbing, Interior Panel Box, Garage Opener. Walking distance from the finest amenities in the area: Cady Way Walking Trail, Ward Park, Winter Park Pines Golf Club and the area’s finest Winter Park School District (Brookshire Elementary, Glenridge Middle, Winter Park High). This home combines prestige and affordability in one irreplaceable address. See it before the opportunity has passed you by!!

2504 Forfarshire Drive, Winter Park

$2,100,000

3 Beds ⋅ 2 Baths ⋅ 32792 Zip Code

A rare opportunity to own nearly 7 acres on the pristine shores of Private Lake Howell! This exceptional lakefront property offers the perfect setting to build your custom dream home while enjoying the privacy and tranquility of one of Central Florida's premier waterfront locations. Spanning nearly 400 acres, Lake Howell is a skiable lake ideal for boating, water skiing, fishing, kayaking, canoeing, paddleboarding, and endless outdoor recreation. With expansive acreage, breathtaking water views, and ample space to create your own private estate, the possibilities are endless. The value is in the land, making this an incredible opportunity for those seeking a premier homesite in a highly desirable location. Don't miss your chance to own one of the area's rare large-acreage lakefront parcels.

1133 Bella Lago Cove, Winter Park

$429,900

4 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 3 SubDv. ⋅ 32792 Zip Code

Oversized corner lot in quiet neighborhood with highly desired Seminole County schools. Well-built block on slab four bedroom home with split floor plan. Enclosed large Florida room. Shed. Existing irrigation well (but pump not working--no warranty on well). Double gate to back yard for parking RV/toys (back left). Roof 2018; water heater 2018; HVAC 2017; CPVC plumbing.

1401 Aster Court, Winter Park

$925,000

4 Beds ⋅ 3 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

Welcome home to this stunningly renovated 4-bedroom, 2.5-bath with TWO additional rooms that can be used as an office space, playroom etc single-family residence located in the heart of Winter Park! This home offers an abundance of space, comfort, and modern convenience in one of Central Florida’s most desirable areas. Step inside to find a bright and open kitchen overlooking a spacious living area—perfect for entertaining family and friends. The additional office space provides a quiet spot for work or study, while the split floor plan ensures privacy and comfort for everyone. Each bedroom features ample closet space, and the home’s thoughtful layout makes daily living a breeze. Enjoy outdoor relaxation on the large backyard and covered porch, ideal for gatherings or peaceful evenings at home. The property also includes an exterior laundry room with washer and dryer for added convenience.

1310 Fairview Avenue, Winter Park

$1,600,000

4 Beds ⋅ 4 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

This home is an adorable 4 Bed 3.5 Bath Home in the heart of Winter Park. You will feel right at home the moment you step in. lovely kitchen showcases gorgeous cabinets, stainless steel appliances, ample amount of cabinetry and counter space, and a breakfast bar, great for entertaining family and friends. Open floor plan. Home features a separate dining area off the kitchen. Spacious living space and bedrooms. Spend your evenings and weekends relaxing on the beautiful lakefront of Lake Killarney, enjoying the incredible sunsets under the shade of huge cypress trees OR poolside in the private fenced in backyard.

250 Killarney, Winter Park

$1,995,000

4 Beds ⋅ 4 Baths ⋅ Tantum Add SubDv. ⋅ 32789 Zip Code

Truly a rare Winter Park offering. Perfectly positioned along the dogleg of the fourth fairway of the historic Winter Park 9-Hole Golf Course, this beautifully renovated four-bedroom, four-bath Mediterranean residence seamlessly blends timeless architectural character with sophisticated modern living. Rich in charm and thoughtfully updated throughout, the home welcomes you with an elegant living room featuring a gas fireplace, classic built-in shelving and abundant natural light. At the heart of the home is a stunning chef's kitchen, complete with custom floor-to-ceiling cabinetry, premium Thermador appliances, a charming breakfast nook and an inviting bar with wine refrigeration that flows effortlessly into the formal dining room, ideal for entertaining. A distinguished first-floor office offers an exceptional work-from-home environment, showcasing a breathtaking custom wall of built-in shelving, cabinetry and an integrated desk. This versatile space also serves beautifully as a library or den. Upstairs, all four bedrooms provide privacy and comfort. The luxurious primary suite features two separate closets, a spacious spa-inspired bath with a soaking tub overlooking the golf course and a private covered balcony perfect for enjoying peaceful morning coffee or evening sunsets. A generously sized secondary suite offers exceptional flexibility with its own custom walk-in closet, en suite bath and private rear staircase, making it ideal for guests, multigenerational living or a secluded retreat. Two additional bedrooms and a well-appointed full bath complete the second level. Updated features include smart house lighting, cabinet and shelving accent lighting, custom built-ins and much more. Designed to embrace Florida's indoor-outdoor lifestyle, the home offers a screened porch accessible from both the dining room and breakfast nook, creating an inviting space for year-round entertaining. Two additional open patios provide the perfect setting to relax while enjoying picturesque golf course views and the tranquil surroundings. Perhaps the home's greatest luxury is its exceptional location. Just steps from the boutiques, acclaimed restaurants, sidewalk cafés and vibrant atmosphere of Park Avenue, this residence offers an unmatched Winter Park lifestyle. Convenient access to downtown Orlando, major hospitals, world-renowned attractions and both Orlando International and Orlando Executive airports makes everyday living as effortless as it is elegant. This is a rare opportunity to own a beautifully updated Mediterranean home in one of Winter Park's most coveted and locations.

922 N Pennsylvania Avenue, Winter Park

$750,000

4 Beds ⋅ 3 Baths ⋅ Landings At Hawks Crest SubDv. ⋅ 32792 Zip Code

Nestled within the gated community of Hawks Crest, this meticulously maintained two-story residence showcases over $70,000 in luxurious builder upgrades, blending timeless design, modern comfort, and effortless Florida Living. This stunning home presents an exceptional opportunity to enjoy one of Winter Park's most desirable lifestyle communities. A welcoming entry opens to light-filled interiors where soaring ceilings, elegant finishes and a thoughtfully designed open-concept floor plan create a seamless flow throughout the home. Luxurious white ceramic tile spans the entire first floor, enhancing the home's bright and airy feel while providing both beauty and durability. The gourmet kitchen serves as the centerpiece of the home, featuring upgraded cabinetry, quartz countertops, stainless steel appliances, abundant storage and an expansive peninsula with bar seating. Spacious living areas and generously sized bedrooms provide comfort and flexibility for a variety of lifestyles. Upstairs, plush carpeting creates a warm and inviting retreat, while the primary suite offers a private sanctuary complete with a large walk-in closet and a spa-inspired bath. Additional bedrooms provide ample space for family, guests, a home office or a fitness room. Sliding glass doors extend the living space to a covered lanai, creating an inviting setting for outdoor dining, morning coffee or relaxed evenings enjoying Florida's year-round climate. Residents of Hawks Crest enjoy an exceptional collection of resort-style amenities, including a clubhouse, state-of-the-art fitness center, community pool, playgrounds, dog park, scenic trails and private access to Lake Howell. The community is also conveniently located near local favorites, including Kelly's Ice Cream, Foxtail Coffee and Park Maitland Preschool. Ideally situated just minutes from Park Avenue, downtown Maitland, major highways, and top-rated schools, this exceptional home offers effortless access to Central Florida's finest shopping, dining and cultural attractions. Despite its convenient location, the community maintains a sense of privacy and tranquility.

1418 Lone Feather Trail, Winter Park

$1,595,000

3 Beds ⋅ 3 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code

In the heart of Winter Park's vibrant Hannibal Square, this exceptional one-story residence, completed in 2022, offers the ideal blend of contemporary design, refined finishes and an unbeatable accessible lifestyle. Thoughtfully designed with three bedrooms, two and one-half baths, and an open-concept floor plan, the home showcases clean architectural lines, soaring ceilings and walls of glass that fill the interior with natural light while framing views of the beautifully landscaped grounds. The chef's kitchen serves as the centerpiece of the home, featuring premium Wolf and Sub-Zero appliances, custom cabinetry, a center island with seating, and workspace for everyday living and entertaining. The adjoining dining area flows seamlessly into the spacious great room, where custom-built library shelving creates a striking focal point and adds warmth and character to the modern design. Beautiful polished concrete floors extend throughout the residence, providing a cohesive and sophisticated aesthetic. Designed with privacy in mind, the split-bedroom floor plan places the primary suite in its own secluded wing. This spacious retreat offers direct access to the covered rear patio and features a beautiful bath with dual vanities, an oversized walk-in shower, private water closet, and an impressive custom walk-in closet measuring approximately 11 by 9 feet. Conveniently accessible from the primary bath and laundry room, the thoughtfully designed closet enhances everyday functionality. On opposite side of the home, two additional guest bedrooms are connected by a well-appointed Jack-and-Jill bath, while a stylish powder bath is ideally located for visitors. Outdoor living is equally inviting with a covered patio with a privacy bamboo hedge that creates a peaceful backdrop for relaxing or entertaining. An attached two-car garage completes this beautifully appointed residence. Ideally near the acclaimed restaurants, wine bars, coffee shops, and boutiques of Hannibal Square, this home offers one of Winter Park's desirable lifestyles. Visit the renowned shopping, dining, galleries and sidewalk cafés of Park Avenue, enjoy nearby Central Park and community events, or take advantage of the proximity to Rollins College, the Winter Park Farmers' Market and major roadways providing convenient access throughout Central Florida. This is a rare opportunity to enjoy nearly new construction in one of Winter Park's sought-after neighborhoods, where modern luxury and exceptional accessibility come together.

462 W Lyman Avenue, Winter Park

$525,000

3 Beds ⋅ 2 Baths ⋅ Glenmoor SubDv. ⋅ 32792 Zip Code

Beautiful meticulously maintained 3-bedroom, 2-bath split floor plan home situated on a desirable corner lot in the established Glenmoor community. Move-in ready, this home features vaulted ceilings with exposed wood beams, a floor-to-ceiling brick fireplace, carpet, and fresh interior paint. The kitchen offers contemporary cabinetry, Silestone countertops, a skylight, stainless steel range, microwave, and refrigerator, and opens to the spacious eating area. A formal dining room provides additional entertaining space. The private primary suite features a walk-in closet, en-suite bath with double vanities and a walk-in shower. The Flex room is currently being used as a 4th bedroom/office with high ceilings and lots of natural light. Leading out you will find a fully fenced backyard retreat with a brick paver patio, tropical landscaping and a gazebo—ideal for outdoor entertaining. Additional features include a two-car garage, inside laundry room with washer and dryer, 12' x 20' storage shed, and a secondary driveway with parking for up to four additional vehicles, boat, or RV. No HOA! Conveniently located near SR 417, Full Sail University, Rollins College, UCF, shopping, dining, parks, and top-rated Winter Park schools. New roof 2024, new gutters 2024, fresh exterior paint 2025, new exterior lighting 2025.

4437 Glenmoor Court, Winter Park

$435,000

3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 16 SubDv. ⋅ 32792 Zip Code

Virtually Staged. Welcome to 2223 Conifer Ave, recently enhanced with a new roof, fresh interior paint, and fresh exterior paint. The kitchen features all stainless steel appliances and an accent backsplash. A walk in closet is included in the primary bedroom, complemented by double sinks in the primary bathroom. Outside, an in ground pool and a covered patio in the back yard, all within a fenced in backyard. Perfectly updated and designed for comfort and enjoyment, this home awaits.. Included 100-Day Home Warranty with buyer activation

2223 Conifer Avenue, Winter Park

$435,000

3 Beds ⋅ 3 Baths ⋅ Wrenwood Unit 3 3rd Add SubDv. ⋅ 32792 Zip Code

Move-in-ready Winter Park gem in top-rated Seminole County schools! This 3BR/2BA home features a private split-bedroom layout. The home features laminated wood flooring in all the bedrooms and beutiful tile in the kitchen and bathrooms. Both bathrooms feature newly updated toilets. The expansive eat-in kitchen is a chef's delight, boasting premium granite countertops, solid light maple cabinets with elegant glass upper doors, and a breakfast bar opening to the large family room. Enjoy total peace of mind with extensive 2023 upgrades, including a BRAND NEW ROOF, new electrical panel, new energy-efficient windows, new French doors, and a new garage door for the 2-car garage.The HVAC system was manufactured in 2019 and installed in 2020 Step outside to a massive, fully fenced backyard featuring a large covered lanai with a brand-new aluminum frame and fresh screens—perfect for outdoor entertaining. Truly a turnkey property optimized for insurance savings and modern comfort. Schedule your tour today!

5225 Albert Drive, Winter Park

$4,250,000

4 Beds ⋅ 6 Baths ⋅ Alexander Place SubDv. ⋅ 32789 Zip Code

Envisioned by acclaimed architect Phil Kean and originally commissioned as the International Showcase Home for the National Association of Home Builders, this award-winning contemporary estate is a masterclass in modern design. Tucked away on a prestigious cul-de-sac between Lake Osceola and the iconic Alfond Inn, the residence offers unparalleled privacy just two blocks from Park Avenue's world-class amenities. A striking entryway with 10-foot mahogany doors reveals a secluded courtyard oasis, featuring a sparkling pool framed by lush Signature landscaping. Inside, expansive living spaces with soaring 14-foot ceilings and a dramatic 40-foot gallery wall flow seamlessly to the outdoors, creating an effortless connection between interior elegance and open-air entertaining. The sleek, state-of-the-art kitchen is curated with premium Monogram, JennAir, and Gaggenau appliances, complemented by a sophisticated wet bar and an intimate media lounge. Ascend the floating staircase or private elevator to the primary sanctuary, which exclusively commands the entire second level. This lavish retreat features a spa-inspired bath with a smart-controlled shower, an oversized marble vanity, and three private terraces. The estate is further elevated by a first-floor guest suite, an executive office, a fitness studio with an en-suite steam shower, and a versatile poolside casita. Integrated smart home technology, automatic Lutron shades, whole-house generator and a three car garage provide ultimate modern convenience. Every element of this residence reflects intentional design, innovation, and timeless elegance, embodying the pinnacle of world-class Winter Park living.

229 Alexander Place, Winter Park

$385,000

4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub SubDv. ⋅ 32792 Zip Code

Beautifully updated 4-bedroom, 2-bath pool home in Winter Park offering modern upgrades and flexible living space. The home features new tile flooring throughout, a fully renovated kitchen with a stunning waterfall quartz island, and two beautifully remodeled bathrooms. The garage has been updated with new flooring and a new garage door. Major improvements include a new roof (2024), new A/C (2023), complete home repipe (2022), updated electrical panel, and pavers in both the front and back of the home. The swimming pool was resurfaced with new tile in 2023 and is approximately 12 feet deep, creating the perfect backyard retreat.

885 Carnation Drive, Winter Park

$849,949

5 Beds ⋅ 4 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code

LIGHTING FAST RESPONSE - FULLY RENOVATED 5-BEDROOM, 4-BATH WINTER PARK ESTATE Welcome to 724 Monmouth Way, a beautifully reimagined five-bedroom, four-bath estate designed for comfortable family living, elegant entertaining, and everyday luxury. Renovated in 2026, this spacious home features thoughtfully separated bedroom wings, impressive living areas, abundant natural light, and designer finishes throughout. The expansive 13-by-22-foot primary suite offers enough space for a private sitting area, reading retreat, or lounge within the bedroom. The luxurious primary bathroom features a double vanity, an oversized shower with dual showerheads, a heated smart toilet, and a six-foot freestanding soaking tub positioned beneath a built-in skylight. Marble fluted accent walls surrounding the tub and shower create a dramatic, spa-like atmosphere. A generous 7-by-8-foot walk-in closet provides abundant storage. At the heart of the home is a newly designed, chef-inspired kitchen featuring a striking 9-by-5-foot double-waterfall island, extensive cabinetry, exceptional storage, a custom range hood surround, and an elegant cabinet column that gives the kitchen a truly distinctive designer look. Two large skylights above the kitchen and adjoining casual dining area fill the space with natural light, creating a bright, open, and inviting atmosphere throughout the day. The adjoining butler’s pantry functions as a second kitchen and includes its own sink and faucet, full-size refrigerator space, extensive cabinetry, and additional countertop space. Prepare meals, store small appliances, and keep entertaining messes neatly tucked away from the main kitchen. A guest bedroom located near the primary suite includes its own private ensuite bathroom. This flexible left-wing space is ideal for overnight guests, a nursery, private office, fitness room, or multigenerational living arrangement. On the opposite side of the home, the right bedroom wing offers added privacy and separation from the primary suite. This hallway includes three additional spacious bedrooms, a full bathroom, and a convenient half bathroom. The large formal living room is filled with natural light from its front-facing windows. A separate 22-foot family room creates an impressive gathering space and features a dramatic 10-foot linear fireplace, making it the perfect setting for holidays, celebrations, movie nights, and everyday relaxation. Outside, the large, thoughtfully designed backyard features newly installed Zoysia grass, a private putting green, and naturally shaded areas perfect for relaxing, entertaining, or enjoying the Florida lifestyle. Major improvements include a new roof, electrical system, plumbing, and water heater completed in 2026, along with an HVAC system installed in 2019. This exceptional Winter Park home combines generous living space, modern luxury, flexible accommodations, dramatic natural light, and extensive renovations in one remarkable property.

724 Monmouth Way, Winter Park

$1,500,000

5 Beds ⋅ 5 Baths ⋅ Park Manor First Add SubDv. ⋅ 32792 Zip Code

Virtually Staged. Built in 2021 by David Weekley Homes, this thoughtfully designed 5-bedroom, 4.5-bath residence delivers 3,109 square feet of refined, light-filled living in one of Central Florida's most desirable locations. The sought-after Easterley floorplan opens into a bright, open-concept layout where soaring ceilings and abundant natural light set an effortlessly elegant tone, with generous room to gather, work, and unwind. At the heart of the home, a gourmet kitchen anchors the space with quartz countertops, a gas range, premium GE appliances, and a walk-in pantry—equally suited to weeknight dinners and lively entertaining. The first-floor primary suite offers a private retreat with a spa-inspired bath featuring a walk-in shower and a separate soaking tub, while four additional bedrooms provide flexible space for guests, a home office, or a playroom. Already plumbed and wired for a pool, the backyard is primed to become your own private oasis—simply add the design you've always envisioned. The location is exceptional. The home is zoned for top-rated schools, is just a short walk to the Winter Park YMCA, moments from Interlachen Country Club, and less than a mile from AdventHealth Winter Park—an unbeatable commute for those in the medical field. Park Avenue's upscale shopping and dining is just two miles away, with Baldwin Park's shops, restaurants, and lakeside trails only three miles from your door. Best of all: NO HOA. Modern construction, an unmatched address, and true Winter Park living—all in one.

777 Halifax Avenue, Winter Park

$2,195,000

4 Beds ⋅ 5 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code

Positioned in one of Winter Park's most desirable neighborhoods, this exceptional French Mediterranean residence is just moments from Phelps Park, the Winter Park YMCA, Lakemont Elementary, and Interlachen Country Club. Built by MichaelCharles Homes with interiors by Wolfe-Rizor Interiors, the home pairs timeless architecture with refined contemporary design, abundant natural light, and exceptional craftsmanship. The thoughtfully designed floor plan offers 4 bedrooms, 4 full bathrooms, and 1 half bathroom. The first-floor primary suite features a spa-inspired bathroom and an expansive custom walk-in closet with dedicated his-and-her wardrobe areas. A flexible adjoining room is ideal as a private office, nursery, fitness room, or optional fifth bedroom. On the opposite wing of the home, the private guest suite includes a full bathroom and walk-in closet. At the heart of the home, the chef's kitchen showcases a large center island, custom cabinetry, and premium finishes. Oversized glass doors open to a covered lanai with outdoor dining, grilling space, and a resort-style pool. Framed by mature Japanese maple trees, the backyard offers exceptional privacy and a spacious lawn for recreation or entertaining. Situated on a quiet, oak-lined street, this custom-built home reflects the quality in every detail, presenting a rare opportunity to own an exceptional residence in the heart of Winter Park.

1750 Walnut Avenue, Winter Park

$569,000

3 Beds ⋅ 3 Baths ⋅ Fairshores Place SubDv. ⋅ 32789 Zip Code

Life in Winter Park is about more than just where you live—it's about how you live. At 2803 Riddle Drive, that lifestyle comes together with an inviting open floor plan, a private full fenced backyard with a pool designed for year-round enjoyment, and a location that's just minutes from everything that makes Winter Park one of Central Florida's most desirable communities. The heart of the home is a bright, open living space where the kitchen, dining, and living areas flow effortlessly together around a wood-burning fireplace. Filled with natural light and designed for connection, it's a space that feels equally suited for lively gatherings, holiday celebrations, or quiet evenings at home. Step outside and discover what truly sets this property apart. A sparkling private pool and a fully fenced quarter-acre yard that creates an outdoor retreat that's increasingly hard to find. Whether you're entertaining friends, watching children or pets play, or simply enjoying a peaceful morning by the pool, this backyard offers the space and privacy to enjoy Florida living the way it was meant to be. Thoughtful updates—including a new roof (2022), HVAC system (2022), fresh interior paint, and updated lighting—provide peace of mind while leaving opportunities for the next owner to make the home uniquely their own. Ideally located just minutes from Park Avenue's dining and boutiques, Lake Killarney, Hillstone, College Park and major commuter routes, this home offers exceptional convenience without sacrificing the character and charm that make Winter Park so special. With a private pool, two-car garage, generous outdoor space, and an open floor plan that truly lives for entertaining, 2803 Riddle Drive offers a rare opportunity to enjoy the Winter Park lifestyle at an exceptional value.

2803 Riddle Drive, Winter Park

$575,000

3 Beds ⋅ 2 Baths ⋅ Kenilworth Shores Sec 07 SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully maintained and thoughtfully updated home in the desirable City of Winter Park, offering an exceptional blend of comfort, space, and convenience. From the moment you arrive, the freshly installed, vibrant green front lawn and attractive landscaping create an inviting first impression. Inside, the cathedral ceiling enhances the spacious feel of the open floor plan, complemented by luxury vinyl flooring and ceramic tile throughout. The well-appointed kitchen features white cabinetry, granite countertops, and a new stainless steel appliance package that adds a modern touch. The home's versatile layout offers plenty of room for everyday living and entertaining, including a separate family room, a bright Florida Room, and a dedicated office or exercise room equipped with an energy-efficient mini-split system and convenient access to the carport. The inside utility room includes a full-size washer and dryer, as well as a second side-by-side refrigerator for added storage and convenience. The spacious primary bedroom provides a comfortable retreat with a private bath featuring maple cabinetry, ample vanity storage, and a roomy walk-in shower. The guest bath offers a tub/shower combination. Step outside to enjoy the spacious, fully fenced backyard—perfect for relaxing, entertaining, gardening, or enjoying the Florida sunshine. Additional features include a storage shed, sprinkler system supplied by a separate well, and a one-car carport with parking for up to three additional vehicles. Major updates include an AC system replaced in 2017, a new roof and electrical panel in 2019, and replumbing completed in 2019. Best of all, you are walking distance to Winter Park High School and just minutes from local dining, shopping, and everyday conveniences. With its spacious floor plan, flexible living areas, attractive updates, generous outdoor space, and prime Winter Park location, this home is a must-see. Schedule your private showing today! Buyer/buyer's agent to verify all schools and room measurements. Appliances convey as is. Brio Management LLC, Seller, is owned by 2 Florida Licensed Real Estate Brokers.

2010 Summerfield Road, Winter Park

$375,000

4 Beds ⋅ 3 Baths ⋅ Winter Woods Unit 01 SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. **MULTIPLE OFFERS - SUBMIT YOUR HIGHEST AND BEST BY 5PM ON MONDAY 7/13** Bank-owned opportunity in Winter Park near Interlachen Country Club, Park Avenue, Full Sail, Rollins, and UCF. Set in Winter Woods, one of the area’s established neighborhoods, this 4/2.5 two-story home sits on a fenced lot w/pool and offers 1,776 sqft, block and brick construction, a 2-car garage, and a primary bedroom with a walk-in closet and private balcony overlooking the pool. The home needs a full renovation, including a new roof. Flooring, kitchen, and HVAC, and the property is priced accordingly. Optional HOA and flood zone X help keep carrying costs simple. Sold As-Is by the REO seller. Cash or renovation financing only.

2189 Sussex Road, Winter Park

$379,900

4 Beds ⋅ 2 Baths ⋅ Suburban Homes First Add SubDv. ⋅ 32792 Zip Code

Updated Winter Park home with major improvements already completed and no HOA! Located at 4965 Orange Ave., this move-in ready property offers a desirable Central Florida location with convenient access to shopping, dining, parks, major roadways, and everything the Winter Park area has to offer. Recent updates include a NEW Roof, Dual-pane, Energy-efficient Windows, 2 NEW A/C systems, fresh interior and exterior paint, upgraded baseboards, Beautifully Remodeled Bathrooms, and terrazzo & ceramic tile flooring throughout (no carpet!!). The galley-style kitchen features stainless steel appliances, a decorative backsplash, and an efficient layout designed for everyday functionality. Both bathrooms have been beautifully refreshed, while the durable flooring and fresh finishes create a clean, cohesive feel throughout the home. Outside, the large fenced yard provides excellent outdoor space for entertaining, gardening, pets, or future possibilities. The attached carport includes a convenient storage and laundry room for added practicality. With no HOA, updated major systems, energy-efficient windows, and a centrally located Winter Park address, this home is an excellent opportunity for buyers searching for an updated home in Winter Park, FL with modern improvements, low-maintenance features, and easy access to the Greater Orlando area.

4965 Orange Avenue, Winter Park

$1,690,000

4 Beds ⋅ 3 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code

A rare elevated corner lot in the heart of Winter Park — walkable to Park Avenue's boutique shops and restaurants, and set on one of the area's most desirable streets. Substantial homesite, prime location, endless potential. Coming soon. Reach out to the listing agent if you would like more information about the property.

708 Balmoral Road, Winter Park

$639,000

4 Beds ⋅ 3 Baths ⋅ Kawilla Crest SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. Welcome to this gorgeous 4-bedroom, 3-bathroom WINTER PARK home that perfectly blends elegance, comfort, and functionality. From the moment you step inside, you'll be impressed by the soaring 12–14-foot ceilings, beautiful CROWN MOLDINGS, and classic PLANTATION SHUTTERS that add timeless charm throughout. Designed with an exceptional flow, this home features formal living and dining rooms, along with a spacious family room centered around a charming fireplace, creating a warm and inviting space for relaxing or gathering with family and friends. The family room seamlessly connects to the heart of the home—a stunning CUSTOM chef's kitchen equipped with high-end appliances, thoughtfully designed cabinet organizers, and abundant workspace, making it a dream for cooking and entertaining. The desirable split floor plan offers both privacy and flexibility, with two bedrooms located in the right wing and two in the left, including a spacious primary suite. Every detail has been carefully considered to create a warm, inviting atmosphere that's ideal for everyday living and hosting guests. Step outside to your private backyard oasis, where a large swimming pool and spacious outdoor living area create the perfect setting for entertaining, weekend gatherings, or simply relaxing. The fully fenced yard provides both privacy and plenty of room to enjoy Florida living year-round. Additional highlights include a **NEW ROOF**installed in 2021**,** NEW LUXURY VYNIL PLANKS FLOORING** in 4 rooms, brand NEW interior painting offering added value and peace of mind for the next owner. This exceptional Winter Park home is a true showstopper that offers luxury, comfort, and timeless appeal. Don't miss the opportunity to make it yours!

1908 Cyril Court, Winter Park

$600,000

2 Beds ⋅ 2 Baths ⋅ Orangewood Park SubDv. ⋅ 32789 Zip Code

Location, location, location. Wonderful home located in Winter Park besides Baldwin Park. Live in this home now - or purchase for the property and build your custom home! The yard is large. Large shed in the yard to store all of your yard essentials. You will love the area and the convenience to what makes this area special...steps from East End Market, lots of amazing restaurants, shopping, Leu Gardens, and so much more. Updates to the home include: Roof: 2020, HVAC 2019, Elecrical - new utility box, Plumbing: re-plumbed Kitchen and both bathrooms. Welcome Home.

2824 Woodside Avenue, Winter Park

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