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$295,000
3 Beds ⋅ 2 Baths ⋅ Windward Square Sec 3 SubDv. ⋅ 32792 Zip Code
Welcome to Windward Square, a desirable Winter Park community conveniently located near shopping, dining, entertainment and major roadways. This spacious end-unit home offers 2 bedrooms, 2 full bathrooms and approximately 1,544 square feet of living space, plus an enclosed 260-square-foot sunroom, providing nearly 1,800 square feet of usable living area. Originally designed as a 3-bedroom home, the third bedroom has been converted into a versatile flex room—ideal for a home office, den, hobby room or additional living space. The primary suite features a spacious walk-in closet with custom built-ins. Recent updates include a new roof in 2023, new flooring, fresh interior paint and more. As an end unit, the home provides additional privacy and a more open feel than interior units. The enclosed sunroom offers additional space for relaxing, entertaining or enjoying your morning coffee. Windward Square residents enjoy community amenities including a swimming pool and tennis courts. The convenient location provides easy access to Winter Park, Orlando and surrounding areas. Whether you’re looking for a primary residence or an investment opportunity, this move-in-ready home offers space, flexibility and an excellent Winter Park location.

2302 Barbados Drive, Winter Park
$245,000
2 Beds ⋅ 2 Baths ⋅ Mead Garden SubDv. ⋅ 32789 Zip Code
Virtually Staged. Updated two-bedroom, two-bath residence offering 908 square feet and a first-floor, pool-facing location in Mead Garden Condominium. The move-in-ready interior features luxury vinyl plank flooring throughout the living areas and bedrooms, tile flooring in the baths and defined living and dining spaces. The kitchen is appointed with white transitional cabinetry, granite countertops, a white subway tile backsplash and stainless steel appliances, including a refrigerator, range, microwave and dishwasher. A pass-through to the dining area incorporates built-in cabinetry, glass-front display storage and additional counter space. The dining area flows into the living room, where sliding glass doors open to an enclosed sunroom overlooking the community pool and landscaped grounds. The primary bedroom features natural light from a pool-facing window, built-in closet storage and an en-suite bath with a walk-in shower and white tile surround. A second bedroom provides flexible space for a variety of uses, while the second full bath offers a tub and shower combination. Additional features include a newer water heater, updated plumbing fixtures and convenient access to the community laundry room just outside the residence. From 1250 South Denning Drive, Residence 127 offers proximity to Mead Botanical Garden, Rollins College, Park Avenue, Azalea Park, Seven Oaks Park and Winter Park dining and retail.

1250 S Denning Drive Unit 127, Winter Park
$299,990
3 Beds ⋅ 2 Baths ⋅ Windward Square Sec 3 SubDv. ⋅ 32792 Zip Code
Great opportunity in the established Windward Square community of Winter Park! This END-UNIT home offers 3 bedrooms, 2 full bathrooms and approximately 1,467 square feet of living space, with added privacy and plenty of potential. ROOF REPLACED IN 2017! The home is ready for some TLC and personal updates, giving the next owner the opportunity to renovate and make it their own. The spacious living and dining areas gives a functional layout, while the large screened porch provides additional space to relax, entertain, and enjoy Florida living. Being located at the end provides additional privacy and a more open feel compared with interior units. The community offers amenities including a swimming pool and tennis courts. Conveniently located near shopping, dining and major roadways, with easy access to Winter Park, Orlando and surrounding areas. Whether you’re looking for a primary residence or an investment opportunity, this property offers great potential and an excellent opportunity to add value through your own improvements. Bring your vision and make this home your own!

2275 Island Run, Winter Park
$295,000
3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 05 SubDv. ⋅ 32792 Zip Code
Now Available in Eastbrook of Winter Park! Come see this charming Home consisting of 3 bedrooms, 2 bath, 1,363(sqft), -clean residence with a spacious layout and great back yard! This is the perfect home for those looking for space and best of it’s move in ready. Property is being sold “as-is” with right to inspect. New Interior & Exterior paint!! It is the buyers and buyer’s agent responsibility to verify all room measurements, utilities info, lot size, schools zoning, building addition permits, building materials, along with all property information in this listing. All room measurements and dimensions are estimates.

1484 Viburnum Lane, Winter Park
$285,000
3 Beds ⋅ 2 Baths ⋅ Windward Square Sec 2 SubDv. ⋅ 32792 Zip Code
Freshly remodeled and move-in ready, this 3-bedroom, 2-bath townhome offers comfortable living in a highly desirable Winter Park location. The open-concept living and dining areas create a welcoming space for everyday living and entertaining, while the convenient pass-through window connects the kitchen and dining room for added functionality. The brand-new kitchen remodel features granite countertops and all-new stainless steel appliances. The spacious primary suite includes a walk-in closet and private en suite bath with a walk-in shower. Two additional bedrooms and a full bath offer ample room for everyone. Tile flooring throughout provides easy maintenance and durability. Enjoy time relaxing outdoors on the covered patio in the privacy of the fenced backyard. Additional recent updates include a new roof, all-new Low-E energy-efficient windows, and a new vanity, toilet, and faucets in the guest bath. Residents enjoy access to the community pool and clubhouse, along with a prime location close to shopping, dining, entertainment, and major roadways. EV parking with outlet for your charger. With its combination of recent upgrades, community amenities, and sought-after Winter Park address, this is the perfect place to call home.

2657 Exuma Way, Winter Park
$269,000
2 Beds ⋅ 2 Baths ⋅ Lazy Oaks Condo SubDv. ⋅ 32792 Zip Code
Welcome to 5108 Lazy Oaks Drive, a 2-bedroom, 2-bathroom condo in a desirable Winter Park location. This light-filled home has approximately 1,008 square feet of comfortable living space with a functional floor plan, abundant windows, skylight and sliding glass doors that bring in plenty of natural light. The spacious living room features a beautiful brick fireplace and sliding glass door access to the screened-in back patio. The patio can also be accessed directly from the primary bedroom, creating a wonderful private outdoor space to enjoy your morning coffee, relax, or entertain. The primary suite features an en-suite bathroom with a walk-in shower, spacious two-sink vanity, and plenty of closet space. The guest bedroom is conveniently located just two steps from the second full bathroom, providing an ideal setup for family, guests, or a home office. The well-maintained original kitchen includes an electric range and oven, refrigerator, dishwasher, and two-basin stainless steel sink. Well-maintained tile flooring runs throughout the home, offering durability and easy maintenance. The spacious one-car garage has more than just parking, with a washer and dryer and plenty of additional storage space. The HOA fee is $277 per month and includes lawn maintenance and responsibility for the entire exterior of the condo, including the roof, providing added convenience and peace of mind for the homeowner. With its fresh interior, abundant natural light, brick fireplace, screened-in patio, private primary suite, attached garage, and low-maintenance lifestyle, 5108 Lazy Oaks Drive is a wonderful opportunity to own a comfortable home in Winter Park.

5108 Lazy Oaks Drive Unit 5108, Winter Park
$269,000
2 Beds ⋅ 1 Baths ⋅ Lake Killarney Condo SubDv. ⋅ 32789 Zip Code
Virtually Staged. Experience lakefront living at its finest in this exceptional Winter Park Condominium Community overlooking beautiful Lake Killarney. Hidden gem complete with access to a community dock, private boat ramp, and a fenced lakeside pool perfect for relaxing and entertaining. Ideally located just minutes from the heart of Winter Park, this home offers unparalleled walkability. Stroll to Park Avenue's renowned boutiques, restaurants, and nightlife, catch a movie at Regal Cinemas, or conveniently shop at Publix and Trader Joe's. With countless restaurants, bars, and everyday amenities just steps away, you'll enjoy the perfect blend of tranquil waterfront living and vibrant urban convenience. Whether you're boating on the lake, lounging by the pool, or taking in the spectacular evening sunsets, this is a rare opportunity to enjoy one of Winter Park's most desirable waterfront lifestyles.

151 N Orlando Avenue Unit 242, Winter Park
$279,900
3 Beds ⋅ 2 Baths ⋅ Coronation Add SubDv. ⋅ 32792 Zip Code
Come see this 3 bedroom 2 bath split plan home. All tile throughout home. Granite kitchen countertops. Eat in area in kitchen. Kitchen bar opens to great room. Huge corner lot great for handyman with trailer, boat, RV or truck to park in backyard. Easy access to add on garage in backyard. Cathedral ceilings great room. NO HOA.

3302 Royal Street, Winter Park
$229,999
1 Beds ⋅ 1 Baths ⋅ Lake Killarney Condo SubDv. ⋅ 32789 Zip Code
HUGE price adjustment, ready for fast sale. Location, location, location! Bring your boat, enjoy lake views and the best of Winter Park from this beautifully updated, move in ready 1 bedroom, 1 bathroom condo in the desirable Lake Killarney community. This top floor beauty features two private entrances and an enclosed patio overlooking Lake Killarney, perfect for morning coffee or relaxing at the end of the day. Inside, you’ll find new flooring, a brand new kitchen, and a beautifully updated bathroom. Lake Killarney Condominiums offers fantastic lakeside amenities including a waterfront pool, private community boat dock and ramp, fitness room, clubhouse, laundry facilities, shuffleboard, picnic areas, and grills. Bring your boat, water ski, jet ski, paddle board, wake board or go fishing on this beautiful lake. The monthly HOA also includes water, sewer, trash, pest control, and exterior and grounds maintenance for easy, low maintenance living. One of the best parts is the incredible walkability! Stroll to Trader Joe’s, Hillstone, and the newly revitalized Winter Park Village with shopping, dining, cafes, and a luxury movie theaters. Park Avenue, the Winter Park Farmers’ Market, and the SunRail station are just minutes away, with convenient access to I 4, downtown Orlando, and Maitland. Whether you are looking for a primary residence, Winter Park getaway, or investment property, this is a rare opportunity to enjoy lake views, fantastic amenities, and an unbeatable location in the heart of Winter Park.

151 N Orlando Avenue Unit 261, Winter Park
$299,000
3 Beds ⋅ 2 Baths ⋅ Ridge High Sub SubDv. ⋅ 32792 Zip Code
Winter Park address with Seminole County taxes, and a new roof already in place from 2023. Three bedrooms, two baths, roughly 1,235 sf of living space in solid concrete block with central air. The 9,000 sf lot is fenced and shaded by mature oaks, and a 550 sf carport with workshop space. Flood Zone X, so no lender-required flood insurance. No HOA. No CDD. For an investor, the basis here pencils from day one and cosmetic updates move the rent meaningfully. For an owner-occupant, this is one of the last ways into a Winter Park address at this price. Please see attached inspection and four points report.

2313 Knoll Street, Winter Park
$299,000
3 Beds ⋅ 1 Baths ⋅ Ridge High 1st Add SubDv. ⋅ 32792 Zip Code
Virtually Staged. Prime Winter Park Opportunity – Original Terrazzo Floors, Solid Block Construction & Endless Potential Discover an exceptional opportunity to own a classic Winter Park home priced at just $299,000. Situated on a generous 0.20-acre lot, this 3-bedroom, 1-bath concrete block home offers 1,208 square feet of living space and the perfect foundation to create your dream home or next investment. Built in 1960, this home showcases beautiful original terrazzo floors, a timeless feature that has become increasingly desirable and can be restored to complement today's popular mid-century modern and contemporary designs. The functional floor plan, abundant natural light, and solid construction provide the ideal canvas for renovation while preserving the home's authentic character. Major improvements have already been completed, including a roof replacement in 2021 and an HVAC system installed in 2018, allowing the next owner to focus on bringing their personal vision to life. To help buyers visualize the possibilities, one of the listing photos features an AI-generated renovation concept illustrating the home's exciting transformation potential. Location is everything, and this home delivers. Nestled in one of Central Florida's most sought-after communities, you'll enjoy convenient access to Downtown Winter Park, Park Avenue, Baldwin Park, Winter Park Village, Rollins College, AdventHealth, top-rated dining, shopping, parks, and major roadways. Whether you're looking to restore a classic mid-century home, renovate for resale, or customize a home that's uniquely your own, opportunities like this under $300k in Winter Park are becoming increasingly rare. Bring your vision and unlock the incredible potential of this Winter Park gem.

2168 Ridge Drive, Winter Park
$245,000
2 Beds ⋅ 2 Baths ⋅ Mead Garden Condominium SubDv. ⋅ 32789 Zip Code
Located just minutes from Winter Park's famed Park Avenue, this charming 2 bed, 2 bathroom corner condominium features a light and bright open floor plan, updated finishes, views of Mead Gardens, and one of Central Florida's most sought after locations! As you enter the front door, you are immediately welcomed by views of Mead Botanical Gardens, Khaki oak wood-look luxury vinyl floors, an open living/dining room combo, a private balcony with garden views and kitchen with freshly painted cabinets and stainless steel appliances. Off of the family room, 2 spacious bedrooms including a master suite with a renovated bathroom, and a second bedroom with private access. Everyday is a vacation when you can start your day off with a coffee on the private balcony, cool off on a warm summer's day in the pool and end it with a walk through the 48 acre natural enclave just next door as the sun sets. Zoned for A rated schools including Audobon Park and Winter Park High school and located just minutes from world class shopping, dining and entertainment in historic downtown Winter Park, Downtown Orlando, and College Park. Schedule your showing Today!

1250 S Denning Dr Unit Unit 233, Winter Park
$299,900
3 Beds ⋅ 1 Baths ⋅ Temple Terrace Annex SubDv. ⋅ 32792 Zip Code
Virtually Staged. This charming 3-bedroom, 1-bathroom Winter Park home offers 1,520 square feet of comfortable living space and plenty of flexibility. The spacious living areas provide room for relaxing and entertaining, while the bedrooms can accommodate a primary suite, guest room, home office, or additional personal space. The outdoor deck and pergola create additional space for dining, entertaining, or relaxing, while the generous yard provides room for outdoor activities and future possibilities. Conveniently located near shopping, dining, parks, major roadways, and everyday amenities, this home offers an opportunity to enjoy the Winter Park area.

1915 Carrigan Avenue, Winter Park
$254,000
2 Beds ⋅ 2 Baths ⋅ Cedarwood Village SubDv. ⋅ 32792 Zip Code
Virtually Staged. LIVE THE WINTER PARK LIFESTYLE! STYLE, SPACE & LOCATION—THIS ONE HAS IT ALL! Welcome to Cedarwood Village, where easy living meets one of Winter Park’s most desirable locations, just minutes from the charm, dining, shopping, and entertainment of Downtown Winter Park and Park Avenue. This beautifully maintained 2-bedroom, 2-bath residence with an enclosed bonus room offers a spacious, light-filled floor plan designed for both comfortable everyday living and entertaining. Vaulted ceilings enhance the open living and dining areas, while the generously sized kitchen features newer appliances, abundant cabinet and counter space, plus room for a cozy breakfast table. Retreat to the oversized primary suite, complete with two large closets and sliding glass doors opening to the bonus room. The renovated primary bath adds a touch of luxury with an updated vanity and impressive custom walk-in shower. The guest bedroom offers its own sliding glass doors leading to the front patio, creating a bright and inviting space for family or overnight guests. The updated guest bath adds convenience with a washer and dryer neatly tucked away in the closet. One of the home's best features is the enclosed bonus room, offering valuable additional living space that's perfect for a home office, den, reading retreat, hobby room, or simply a relaxing place to unwind. Enjoy the Florida lifestyle without leaving the neighborhood! Cedarwood Village offers a sparkling community pool, two tennis courts, and clubhouse for residents to enjoy. And then there’s the LOCATION! Shopping, restaurants, medical facilities, and everyday conveniences are all close by, with easy access to major roadways and the boutiques, sidewalk cafés, restaurants, parks, and unmistakable charm of Park Avenue and Downtown Winter Park just minutes away. More than a home—it’s a Winter Park lifestyle. Come see why Cedarwood Village is such a special place to call home!

2477 Tahoe Circle Unit 2477, Winter Park
$249,900
4 Beds ⋅ 3 Baths ⋅ Whisperwood Condo SubDv. ⋅ 32792 Zip Code
Under contract-accepting backup offers. OWNER FINANCE may be available with down payment. Unique 4 Bedroom 3 bath unit. Perfect for investors looking to rent to college attendees at UCF and surrounding or for larger families needing 4th bedroom. Lots of upgrades including 2 new bathrooms, new laundry room, new flooring and lots of new paint. Brand new AC system installed in 2025 and hot water heater in 2022. Granite counters, stainless appliances, ceiling fans and tons of storage. Rear screened and covered lanai off living room, covered and open rear private yard/ garden off kitchen and private balcony off master bedroom. Minutes to UCF, lots of shopping and all major highways

7487 Canford Court Unit 5, Winter Park
$285,000
2 Beds ⋅ 3 Baths ⋅ Sandlewood Creek Phase 2 SubDv. ⋅ 32789 Zip Code
Virtually Staged. MOVE IN READY in Winter Park with nearly $30,000 in recent upgrades and improvements! This beautifully updated 2 bedroom, 2.5 bathroom condo in Sandlewood Creek offers a bright, open layout, conservation views and a quiet community setting in an incredibly convenient location. The main level features a spacious open living and dining area with plenty of room to create separate gathering and dining spaces while maintaining an easy flow throughout the home. The updated kitchen features white cabinetry, granite countertops, stainless steel appliances and a breakfast bar overlooking the living and dining space. A convenient half bath, interior laundry, washer and dryer included, and an additional downstairs storage closet complete the first floor. Step outside to the screened rear porch overlooking conservation, creating a peaceful outdoor space with added privacy. Upstairs, the primary bedroom features a private en suite bathroom, while the second bedroom is located near the additional full bath. A small landing separates the two bedrooms and includes an additional upstairs storage closet, providing valuable extra space for linens, seasonal items or everyday storage. Nearly $30,000 in recent upgrades and improvements include vinyl flooring and baseboards upstairs completed in September 2023, an updated kitchen with cabinetry, countertops and stainless steel appliances in 2023, AC installed in January 2024, roof is 2021, washing machine replaced in 2024, fresh interior paint and new downstairs baseboards completed in July 2026, plus a 2018 water heater. Sandlewood Creek is an established community with a community pool and one assigned parking space. Maitland Community Park is located directly behind the community and connects to additional park space, offering convenient access to trails and outdoor recreation. Park Avenue and Downtown Winter Park are approximately 10 minutes away, putting shopping, dining and entertainment within easy reach. With its extensive recent improvements, conservation setting, screened porch, multiple storage areas and convenient Winter Park location, this home is truly move in ready.

283 Sandlewood Trail Unit 3, Winter Park
$214,900
3 Beds ⋅ 3 Baths ⋅ Hidden Oaks Condo Ph 01 SubDv. ⋅ 32792 Zip Code
MOTIVATED SELLER...Welcome To This Beautifully 3 Bedroom, 2.5 Bathroom Condominium Located in the Desirable Hidden Oaks Community. Offering Updated Living Space, This Home Combines Comfort, Style, and an Unbeatable Location. Step Inside to a Spacious and Inviting Family Room Featuring Beautiful Laminate Flooring, Abundant Natural Light, and an Open, Welcoming Atmosphere. The Updated Kitchen Is Sure to Impress with Quartz Countertops, Stainless Steel Appliances, and A Sliding Glass Door That Opens to a Private Patio—Perfect for Relaxing or Entertaining. Upstairs, You'll Find All Three Bedrooms and Two Full Bathrooms, including a Generously Sized Primary Suite with a Walk-In Closet and Large Front-Facing Windows That Fill the Room with Natural Light. Residents of Hidden Oaks Enjoy a Peaceful Setting with Access to a Community Swimming Pool, Assigned Parking, And Plenty of Guest Parking. Ideally Located Just Minutes from Major Highways 408 And 417, This Home Is Only 4 Minutes from Full Sail University, Minutes from the University of Central Florida (UCF), Downtown Orlando, and Conveniently Close to Valencia College, Rollins College, Winter Park Shopping and Dining, Restaurants, and Everyday Conveniences. The Property Is Also Zoned for Highly Desirable Winter Park Schools, Making It an Excellent Choice for Homeowners and Investors Alike. Don't Miss This Move-In-Ready Opportunity in One of the Area's Most Convenient Locations!

7413 Belle River Court Unit 3, Winter Park
$284,900
2 Beds ⋅ 3 Baths ⋅ Lazy Oaks Condo SubDv. ⋅ 32792 Zip Code
Virtually Staged. DISCOVER THE SERENE BEAUTY OF THIS WINTER PARK TWO-STORY TOWNHOME! Located in the SOUGHT-AFTER Lazy Oaks community. Blending contemporary style with everyday convenience, GORGEOUS 2-BEDROOM, 2.5-BATHROOM, 1-CAR GARAGE HOME. From the moment you step inside, you’ll be greeted by an OPEN-CONCEPT LIVING AREA filled with NATURAL LIGHT, creating a warm and inviting atmosphere. Cook like a pro in the BRAND NEW KITCHEN featuring NEW QUARTZ COUNTERTOPS and SLEEK STAINLESS STEEL APPLIANCES—perfect for culinary enthusiasts. This home is LOADED WITH UPGRADES, including: Newer Roof with 30-Year Shingles, New Laminate Flooring Throughout, Renovated Bathrooms with New vanities, Fresh Interior & Exterior Paint, New Light Fixtures, Faucets, Toilets, Water Heater from 2020, HVAC System from 2015. With affordable condo fees, this home offers both comfort and peace of mind. Located in a wonderful community, you'll enjoy easy access to shopping, major roads, and just minutes away from the vibrant Park Avenue. This move-in-ready home truly has it all! All measurements are approximate and should be verified by the buyer. Virtual Staging was added to some of the pictures.

5210 Lazy Oaks Drive, Winter Park
$249,000
Winter Park SubDv. ⋅ 32789 Zip Code
A rare piece of land in the heart of Winter Park. Short distance to Park Ave. Approved permits for 2000 sqft under AC housing project.

669 W Comstock Avenue, Winter Park
$278,000
2 Beds ⋅ 2 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code
Turnkey Living in the Heart of Winter Park! Welcome to this beautifully maintained 2-bedroom, 2-bath townhome offering the perfect blend of comfort, convenience, and low-maintenance living. Vacant and move-in ready, this home has been freshly painted and features a recently replaced air conditioning system, providing peace of mind for its next owner. Inside, you'll find a thoughtfully designed floor plan with spacious living and dining areas, a well-appointed kitchen, and two generously sized bedrooms and bathrooms designed for comfort and functionality. Whether you're relaxing at home or entertaining friends and family, this inviting layout makes everyday living effortless. Step outside and enjoy the exceptional community amenities, including a sparkling swimming pool and tennis courts, perfect for enjoying Florida's year-round sunshine. Whether you're a first-time homebuyer, downsizing, seeking a second home, or looking for an investment opportunity, this property offers incredible versatility. Ideally located in desirable Winter Park, you'll be just minutes from shopping, dining, entertainment, major highways, UCF, Full Sail University, Downtown Winter Park, and Downtown Orlando, making commuting and enjoying Central Florida's best attractions a breeze. Don't miss your opportunity to own this beautifully updated, turnkey home in one of Central Florida's most sought-after communities! All room measurements, HOA information, square footage, and property details are deemed reliable but not guaranteed and should be independently verified by the buyer and buyer's agent.

2475 Tahoe Circle, Winter Park
$230,000
2 Beds ⋅ 2 Baths ⋅ Four Seasons Condo SubDv. ⋅ 32792 Zip Code
Under contract-accepting backup offers. ATTENTION ** SELLER OFFERING A $5,000 CREDIT TOWARDS BUYER'S CLOSING COSTS OR INTEREST RATE BUY DOWN!! A GEM! Tucked away in a private, sought after community and so conveniently located in breathtaking Winter Park. Here’s a beautifully maintained, upgraded and move-in ready home. With 2 large bedrooms and 1.5 bathrooms, this unit spans 1,219 square feet, providing an ideal space for cozy living. Enjoy the benefits of a peaceful and friendly community, with well-manicured grounds and a welcoming atmosphere. This charming home has been tastefully updated with upgraded laminate flooring, a renovated kitchen with granite countertops, newer cabinets and a stylish backsplash. The floor plan offers a dining & family room open combination which looks out on the porch and brings in plenty of natural light. Both nicely sized bedroom suites are on the second floor and have a shared & updated bathroom. Ample storage on the back patio for your bike and all your extra toys allowing you to enjoy your weekends. This is an extremely well managed community with an onsite manager taking pride in the community and care for their residents. Four Seasons community provides super amenities including a cubhouse with library, a renovated fitness center, 3 swimming pools, tennis courts, a laundry facility steps away and shuffleboard. Walk to Cady Way Park with tennis courts, baseball and soccer fields, playgrounds, community pool and Cady Way Trail. Minutes to Advent Health Winter Park Hospital, shopping on Park Avenue, Rollins College, Valencia, Full Sail and UCF. This pet friendly community and charming condo has everything you need! Great opportunity to own in FOUR SEASONS condominiums where LOCATION, LOCATION, LOCATION is prime!

200 Saint Andrews Boulevard Unit 2904, Winter Park
$270,000
3 Beds ⋅ 3 Baths ⋅ Windward Square Sec 1 SubDv. ⋅ 32792 Zip Code
Welcome to 2487 Harbour Way, a spacious single-story townhome offering 3 bedrooms, 3 full bathrooms, and 1,803 square feet of comfortable living space. The practical layout features inviting living and dining areas, a well-equipped kitchen, central air, and a walk-in closet. Outside, garden space, lighting, and sidewalks add to the home's appeal. Enjoy a low-maintenance lifestyle in Windward Square, where residents have access to a community pool and playground, with the pool included in the low monthly HOA fee. Conveniently located near schools, parks, shopping, dining, and everyday essentials, this Winter Park property offers space, convenience, and community amenities in one appealing package. Schedule your private showing today!

2487 Harbour Way, Winter Park
$250,000
3 Beds ⋅ 2 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code
Rare end units like this don't come around often! Welcome to 2450 Grand Teton Circle, tucked away in the well-maintained, established community of Cedarwood Village in Winter Park. This 3-bedroom, 2-bath home is filled with natural light thanks to its end-unit location, and the open layout makes it easy to relax, entertain and enjoy everyday living. The spacious living and dining areas flow together nicely, while the kitchen offers plenty of room to cook, gather, and stay connected with family and friends. Over the past several years, this home has been thoughtfully updated, giving the next owner peace of mind. Major improvements include a new roof, skylights, HVAC system, water heater, kitchen appliances, washer and dryer, updated LED lighting, and fresh interior paint. Both bathrooms have been beautifully remodeled, the home has been replumbed by the HOA, and the primary closet has been enhanced with custom shelving. Additional updates include new flooring in the secondary bedrooms, updated window blinds, and thoughtful finishing touches throughout. The private screened lanai has been transformed into a cozy outdoor retreat with fresh paint, a ceiling fan, new screens and screen door, string lighting, and decorative greenery—making it the perfect place to enjoy your morning coffee or unwind after a long day. Life here is easy. Cedarwood Village is a beautifully maintained, established community featuring a community pool and Clubhouse for your special events, tennis courts, and pickleball courts. The HOA has also recently repainted the exterior of the buildings, helping keep the neighborhood looking fresh and inviting. Best of all, this home is value priced, giving you an incredible opportunity to own in desirable Winter Park without the premium price tag. You're just minutes from Winter Park's shopping and dining, Full Sail University, UCF, major employers, and convenient access to SR-417 and downtown Orlando. If you've been looking for a move-in-ready home in a fantastic location with years of thoughtful updates already completed, this rare end unit is definitely worth a look!

2450 Grand Teton Circle Unit 2450, Winter Park
$300,000
2 Beds ⋅ 2 Baths ⋅ Aloma Park SubDv. ⋅ 32792 Zip Code
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 5781 Shale Court in Winter Park, a 2-bedroom, 2-bath home designed for comfortable everyday living. This one-story residence offers a practical layout with space for relaxing, dining, and hosting guests. The two-bedroom configuration provides flexibility for residents, visitors, a home office, or a hobby room, while two full bathrooms add convenience for daily routines. Outdoor living includes a covered and screened patio, creating a comfortable space to enjoy fresh air, outdoor dining, or quiet downtime while staying shaded and protected from the elements. Located in Winter Park, the home is close to shopping, dining, parks, schools, and everyday conveniences. The area offers access to nearby destinations such as Winter Park Village, Park Avenue, local recreation, and major roadways connecting to Maitland, Orlando, and surrounding Central Florida communities.

5781 Shale Court, Winter Park
$275,000
2 Beds ⋅ 2 Baths ⋅ Lazy Oaks Condo SubDv. ⋅ 32792 Zip Code
Charming two-bedroom, two-bath condominium available in Winter Park. The reserve is fully funded, and monthly condominium fees are low. A comfortable foyer welcomes you inside, leading down the hallway to the second bedroom at the front of the home, where a large window overlooks the front green space. The kitchen opens to a bright, inviting space with skylights that bring natural light into the combined living and dining area. A fireplace adds warmth to the room, while sliding glass doors lead to a private screened enclosure overlooking additional green space at the rear of the property. Ideally positioned within the home, the kitchen features all-new appliances and an oversized pantry with spice shelving for easy organization. The primary bedroom offers an inviting entrance with closet space upon entry. Sliding glass doors fill the room with soft natural light, creating a calm and peaceful atmosphere. The primary bath includes a double vanity and additional deep closet space. From the bedroom, step out to the screened enclosure and enjoy quiet moments in the Florida breeze. Lazy Oaks Condominium is a charming, peaceful community in Winter Park. Conveniently located near shopping, restaurants, schools, and universities, it offers an inviting place to relax and call home.

5184 Lazy Oaks Drive, Winter Park
$279,900
2 Beds ⋅ 2 Baths ⋅ Cedarwood Village SubDv. ⋅ 32792 Zip Code
Beautifully renovated 2 bedroom, 2 bathroom condo at 2305 Sun Valley in Winter Park, offering a fresh modern design and thoughtful updates throughout. The fully redesigned kitchen features sleek cabinetry, quartz countertops, GE stainless steel appliances, a marble tile backsplash, abundant storage, recessed lighting, and a clean open feel that connects seamlessly to the main living areas. Wood-look porcelain tile flooring runs throughout the home, creating a cohesive, attractive, and low-maintenance finish. The spacious living area features vaulted ceilings, skylights, updated ceiling fans, and sliding glass doors that fill the space with natural light and lead to a covered screened patio overlooking green space. The primary suite includes an updated double vanity and a beautifully redesigned bathroom with a separate tub and newly installed shower. The second bathroom also offers an updated vanity and clean neutral finishes. Additional highlights include a 2021 AC, 2021 water heater, updated fixtures, generous natural light, and a screened outdoor living space ideal for relaxing and enjoying Florida’s indoor-outdoor lifestyle. This move-in ready Winter Park condo combines modern style, comfort, and everyday functionality. Residents enjoy access to a sparkling community pool, clubhouse, tennis and pickleball, and a pet walk with waste stations. Monthly fees also include roof and exterior building maintenance, exterior pest control, and landscaping, adding convenience and long-term value.The location is hard to beat, just minutes from Park Avenue, UCF, Rollins College, Full Sail University, shopping, dining, entertainment, and nearby medical facilities.

2305 Sun Valley Cir, Winter Park, Fl 32792, Winter Park
$285,000
2 Beds ⋅ 2 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully updated condo, ideally nestled between Winter Park and Maitland. This inviting home features a versatile upstairs loft overlooking the living and dining areas—perfect for a home office, fitness space, craft room, or additional guest accommodations. The bright, cheerful eat-in kitchen is both stylish and functional, showcasing quartz countertops, a glass tile backsplash, abundant cabinetry, a pull-out spice rack, trash/recycling cabinet, and a built-in storage unit. Sliding glass doors open to the private front courtyard, filling the space with natural light. Conveniently located laundry area, complete with washer and dryer, is tucked within the kitchen. The spacious living room features a cozy wood-burning fireplace and flows seamlessly into the dining area beneath soaring vaulted ceilings accented by skylights. Sliding glass doors lead to a screened lanai with a slate tile floor and a storage closet—an ideal spot to relax and enjoy Florida living. The primary suite also opens directly to the lanai and offers a beautifully renovated en-suite bath with a luxurious walk-in shower, updated vanity, linen cabinet, and a custom walk-in closet with built-in organizers. The front bedroom also includes a generous walk-in closet. Enjoy added privacy with a picturesque, tree-lined green space across the street rather than neighboring condos directly in front. Two dedicated parking spaces are conveniently located just outside your door. Cedarwood Village offers an exceptional location directly across from Casselberry Commons Shopping Plaza and is just minutes from Full Sail University, UCF, and Rollins College. Residents enjoy a community swimming pool, tennis courts with pickleball lines, and designated dog-walking areas. Additional highlights include a new roof and skylights installed in 2020. Monthly HOA fees cover exterior maintenance, lawn care, and community amenities, making this the perfect opportunity to enjoy carefree living in one of the area's most desirable communities.

2372 Sun Valley Circle Unit 2372, Winter Park
$235,000
2 Beds ⋅ 1 Baths ⋅ Slovak Village SubDv. ⋅ 32792 Zip Code
Why Rent WHEN you can own this 2 bedroom 1 bath single car garage on this 1/2 duplex with NO HOA. Located conveniently to all major roads, shopping, schools and restaurants. New roof installed 2025. Don't hesitate to come view!

2712 Tortoise Cv, Winter Park
$296,500
3 Beds ⋅ 2 Baths ⋅ Windward Square Sec 3 SubDv. ⋅ 32792 Zip Code
Enjoy abundant natural light throughout this beautifully maintained one-story, 3-bedroom, 2-bath home, enhanced by soaring vaulted ceilings and an inviting open layout. The kitchen features natural wood cabinetry, stainless steel appliances, and a charming breakfast nook with access to the front patio. The spacious primary suite offers a walk-in closet and private access to the patio. A desirable split-bedroom floor plan provides added privacy, with two guest bedrooms and a full guest bath situated at the front of the home. The bright and versatile patio can be accessed from both the living room and primary suite, creating the perfect space to relax, entertain, or enjoy year-round Florida living. Roof 2023, A/C 2020, Water Heater 2020, pex piping upgrades include pavered driveway, bathrooms updated, patio doors updated, and vinyl fencing in backyard.

2339 Inagua Way, Winter Park
$235,000
2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code
NEW PRICE/Seller Motivated! WINTER PARK LOCATION ALERT with AMAZING WALKABILITY to SO MANY shopping and dining options! Across from the newly renovated WP Shopping Village that includes top-rated restaurants, a movie theater, boutiques, grocery store and more! This 2bedroom/2 bathroom attractive second-story unit offers an updated kitchen and bathrooms with solid countertops. All solid flooring throughout - tile and laminate for easy care...no carpet. Enjoy the dining space that opens to the large great room and balcony where you'll love sitting in the evenings to relax. SPACIOUS BEDROOMS - Primary bedroom has an attached full bathroom and bedroom 2 has a LARGE walk-in closet. The 2nd Full Bathroom is accessed via a common hallway. The Chateaux Du Luc LAKEFRONT COMMUNITY offers FABULOUS AMENITIES that include an oversized heated pool, clubhouse, community deck, BBQ grill, 2 on-site saunas, updated on-site laundry facilities, and a resident-only boat ramp on skiable Lake Killarney. There's even storage for your Kayak or paddleboard! Roof 2025. Reach out today for your personal showing!!

1500 Gay Road Unit 3C, Winter Park