Maitland FL Homes for Sale

3 Beds ⋅ 2 Baths ⋅ Oakland Shores 1st Add SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Seller has received MULTIPLE OFFERS, and are accepting offers until 5pm on Saturday, JULY 11, 2026. Welcome to your own private resort in the heart of Maitland! Perfectly situated on a beautifully landscaped .27-acre lot in the established Oakland Shores neighborhood, this exceptional three-bedroom, two-bathroom home offers close to 1,800 square feet of thoughtfully updated living space designed for both everyday comfort and unforgettable entertaining. The backyard is truly the star of the show, featuring a spectacular saltwater pool and spa completed in 2023. Designed to impress, this outdoor oasis showcases a stunning Tahoe Blue pebble finish, expansive sun shelf, elegant waterfall and scupper features, dramatic integrated fire bowls, and a heater/chiller for year-round enjoyment. The surrounding travertine pool deck, professionally designed landscape lighting, mature landscaping, and fully fenced backyard create an incredibly private setting, while the Paradise Grill summer kitchen(negotiable with the sale) makes outdoor entertaining effortless. The lush, beautifully manicured landscaping is effortlessly maintained by a 10-zone irrigation system with spray heads, back-flow prevention, and convenient Wi-Fi connectivity, allowing you to monitor and control watering schedules from virtually anywhere. Additionally, a comprehensive underground gutter drainage system directs all roof water to the street, minimizing standing water and protecting the home's foundation and landscaping. Inside, the home is equally impressive with an open and inviting layout enhanced by wood laminate flooring installed in 2019, custom white oak interior doors, crown molding, and large picture windows that frame picturesque views of the backyard retreat. The spacious living room, expanded in 2018, features a beautiful wood-burning fireplace added in 2019 along with custom built-in cabinetry and a built-in desk, creating the perfect gathering space. A newly added laundry/utility room(2026) includes the washer and dryer for added convenience. The kitchen is designed for both function and style with custom wood cabinetry, granite countertops, stainless steel appliances, a pantry, and a center island with seating for three, all overlooking the pool through a large picture window. The private primary suite offers custom cabinetry designed for a king-sized bed, custom blackout shades, white oak closet doors, a ceiling fan, and a beautifully remodeled ensuite bathroom completed in 2026 featuring floor-to-ceiling tile, a custom wood vanity, and a spacious frameless glass walk-in shower. Additional highlights include an oversized paver driveway, two-car garage, and an unbeatable location just minutes from Lake Lily Park, the skiable Lake Orienta boat ramp, I-4, and the shopping, dining, and entertainment destinations of Maitland and Winter Park. This is a rare opportunity to own a home where every day feels like a vacation. ROOF - 2016 HVAC - 2018 ELECTRICAL - 2026 WATER HEATER - 2026

623 Woodley Road, Maitland

$769,000

6 Beds ⋅ 3 Baths ⋅ English Estates Unit 3 SubDv. ⋅ 32751 Zip Code

HONEY STOP THE CAR! This Maitland POOL home has EVERYTHING you need and MORE under one roof! Welcome to one of Maitland's most desirable neighborhoods English Estates. This 6 Bedroom, 3 Bathroom estate offers over 2,600 square feet of living space with a Split Bedroom Floor Plan and a Private Pool. This home is Move-In ready and provides comfort with modern style and top of the line updates by offering the perfect combination of luxury and space which is ideal for Large Families, Multi-Generational households, and working professionals seeking a premium residence. Once you step inside, you'll find an Open Concept showcasing the Kitchen, Living Room, and Dining Room with lots of natural light down to the fine details of Wainscoting and Crown Molding. The Kitchen is the Heart of the Home and this Kitchen is surely that! Great space for the whole family to enjoy and gather around the Extra Large Island. The Kitchen comes equipped with Real Wood Cabinets, Granite Countertops, and all major Stainless Steel Appliances including a Gas Stove with Hood Vent, Dishwasher, Fridge, and Microwave. Located off the Kitchen, the Living Room opens up to the Florida Room that leads out to your own Private Pool with Screen Enclosure. The Split Bedroom Floor Plan in this home features 3 Bedrooms on each side of the home, a true even split, giving you a thoughtful layout for everyday living, entertaining, and working from home. The ROOF and AC by Trane with Nest Thermostat are all from 2021. This home comes with Natural Gas at the Stove, Tankless Water Heater, and Dryer. The Extra Long Driveway with Additional Parking on the side provides ample parking for all your vehicles, boats, RV's and toys. Residents enjoy access to A-Rated Schools and a voluntary low-cost HOA. This location is ideal and conveniently located near 1792 which is a short distance to Maitland Community Park and Maitland City Centre where there are local dining spots and recreation activities. This home is also close to Winter Park, Rollins College, AdventHealth, and 10 minutes to Downtown Orlando. Whether you're looking for more space or a new lifestyle, this home delivers! Come enjoy one of Maitland's most established sought-after neighborhoods.

2462 Carolton Road, Maitland

$995,000

4 Beds ⋅ 4 Baths ⋅ Hidden Estates Unit 3 SubDv. ⋅ 32751 Zip Code

Welcome to Hidden Estates, where luxury, space, and flexibility come together in one of Maitland's most sought-after neighborhoods. Nestled on a quiet cul-de-sac, this rare single-story custom residence offers over 4,000 square feet of thoughtfully designed living space on an expansive three-quarter-acre lot. From the moment you arrive, you'll appreciate the impressive curb appeal, oversized driveway, and exceptional parking with plenty of room for multiple vehicles, boats, RVs, trailers, and recreational equipment. Inside, the home's spacious open layout is designed for both everyday living and entertaining, featuring soaring ceilings, hardwood flooring, crown molding, skylights, custom built-ins, plantation shutters, and a wood-burning fireplace. At the center of the home is a beautifully appointed chef's kitchen with custom mahogany cabinetry, granite countertops, a Thermador refrigerator, six-burner gas cooktop, double ovens, an oversized island with bar seating, and a generous walk-in pantry. The luxurious primary suite serves as a private retreat with its own sitting area, walk-in closet, heated bathroom floors, dual vanities, oversized walk-in shower, and freestanding soaking tub. One of the home's most unique features is its flexible layout, including a private guest suite situated on the opposite side of the home and a separate office overlooking a tranquil atrium, offering endless possibilities for guests, multigenerational living, a home office, or creative space. Step outside to your own private backyard oasis featuring a screened saltwater pool and spa with waterfall, an expansive covered lanai, and abundant outdoor living space designed for year-round Florida enjoyment. The oversized lot provides exceptional privacy while offering ample room to relax, entertain, or personalize the outdoor space. Additional highlights include a metal roof with copper fascia (2018), new septic drain field, and an unbeatable Maitland location convenient to shopping, dining, parks, major roadways, and everyday conveniences. This is a rare opportunity to experience the space, privacy, and versatility that define luxury living in Maitland.

229 Flame Avenue, Maitland

$950,000

3 Beds ⋅ 2 Baths ⋅ Dommerich Woods SubDv. ⋅ 32751 Zip Code

Outstanding Dommerich Woods location on .28 acre lot with serene views of the nature preserve! This immaculate home offers the perfect blend of comfort, style and privacy. Tucked away on a charming tree-lined cul-de-sac, 823 Woods Court welcomes you with exceptional curb appeal. Step inside to a spacious foyer introducing gleaming wood floors, elegant crown molding, and an abundance of natural light. The versatile floor plan offers several inviting living spaces! At the front of the home, the formal living & dining rooms flow seamlessly into the beautifully updated kitchen, complete with a cozy breakfast nook, new cabinetry, quartz countertops, stainless steel appliances and an oversized breakfast bar overlooking bright family room. French doors open to the spectacular 28x11 sunroom with vaulted ceilings and a stunning wall of windows, providing breathtaking views of the manicured backyard, two private patios and the tranquil nature preserve- creating a peaceful retreat you'll enjoy year-round. The spacious primary suite features two closets and a generously sized en-suite bath with dual vanities and built-in storage. Two additional guest bedrooms and a large guest bathroom with built-in closets provide plenty of space for family and visitors. Additional updates and features include fresh interior paint, an inside laundry room, a two-car garage with new garage door, a new Trane HVAC system. new water heater. irrigation system with new well pump, Roof 2018 & NO HOA! Excellent schools: Dommerich Elementary, Maitland Middle & Winter Park High! Residents enjoy access to the Dommerich boat ramp on Lake Minnehaha/Chain of Lakes, as well as a short stroll to the newly refurbished boardwalk leading to Maitland Community Park. This move-in ready home combines an exceptional location, thoughtful updates, and picturesque surroundings ...WELCOME HOME!

823 Woods Court, Maitland

$235,000

4 Beds ⋅ 2 Baths ⋅ Visconti West Condo SubDv. ⋅ 32751 Zip Code

A rare 4 BR condo with A rated High School could be your next home. Visconti is a high end luxury community featuring a huge lakeside pool with beach entry, fitness center that rivals many commercial gyms, tennis courts, walking paths, and a fantastic clubhouse. The 2nd floor condo has an extremely functional layout that separates the master BR from the other 3 bedrooms. The kitchen is stunning with updated cabinets, solid surface counters and a gorgeous back splash. The common areas feature wood laminate floors with carpet in the bedrooms. Conveniently located in Maitland, this homes is just minutes away from restaurants, shops, I4, 414, and the Maitland business center. A fantastic choice for your main home, a 2nd home or an addition to a rental portfolio.

1460 Lake Shadow Circle Unit 7207, Maitland

$199,000

2 Beds ⋅ 2 Baths ⋅ Visconti East SubDv. ⋅ 32751 Zip Code

Experience resort-style living in the heart of Maitland at the highly desirable gated community of Visconti. This beautifully maintained three-story townhome offers 1,280 square feet of thoughtfully designed living space plus an oversized attached garage, providing the perfect combination of comfort, functionality, and low-maintenance living. The open-concept main living level features luxury vinyl flooring, soaring ceilings, abundant natural light, and a spacious kitchen with stainless steel appliances, updated countertops, tile backsplash, breakfast bar seating, and generous cabinet space. The spacious primary suite offers a large walk-in closet and private bath, while the additional bedrooms provide flexibility for guests, a home office, or growing families. A full-size interior laundry room, ample storage, and neutral finishes make this home truly move-in ready. Visconti residents enjoy an impressive collection of amenities including a gated entrance, resort-style swimming pool, a state-of-the-art fitness center, playground, scenic walking paths, car wash station, and beautifully landscaped grounds shaded by mature oak trees. Conveniently located just minutes from I-4, Winter Park, Downtown Orlando, AdventHealth, RDV Sportsplex, shopping, dining, and entertainment, this home offers the perfect blend of convenience, lifestyle, and value.

1952 Legacy Cove Drive Unit 1952, Maitland

$195,900

1 Beds ⋅ 1 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code

LAKE ACCESS LIVING in one of Central Florida's most desirable locations! Welcome to 1140 S. Orlando Ave E11, a move in ready condo ideally located on the Winter Park and Maitland border in the sought after Lake Maitland Terrace community. Enjoy private access to Lake Maitland, part of the prestigious Winter Park Chain of Lakes, where you can spend your days paddle boarding, kayaking, boating, fishing, or simply relaxing by the water. Community amenities include a brand new lakefront pool, clubhouse available for private events, shuffleboard, putting green, community laundry facilities, COMMUNITY DOCK and additional storage. Inside, you'll find a functional floor plan with separate living and dining spaces, abundant natural light, and a well maintained interior that's ready to enjoy or personalize over time. Whether you're looking for a primary residence, seasonal retreat, or investment opportunity, this condo offers exceptional value in an unbeatable location. Just minutes from Park Avenue and walking distance to local favorites including the Enzian Theater, Eden Bar, Luke's Kitchen and Bar, Antonio's, Francesco's, the Shoppes at Maitland, and beautiful Lake Lily Park. With easy access to downtown Winter Park, downtown Orlando, I 4, shopping, dining, and entertainment, this is low maintenance Florida living at its best.

1140 S Orlando Avenue Unit E11, Maitland

$140,000

2 Beds ⋅ 2 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code

Welcome to Carrington Park — one of Maitland’s most conveniently located communities! This ground-floor 2-bedroom, 2-bathroom condo offers 1,200+ square feet of comfortable living space at an unbeatable price point, making it an ideal primary residence or a smart addition to any investment portfolio.The open living and dining area flows naturally to a private screened patio perfect for enjoying Florida’s year-round weather without the bugs. Both bedrooms are generously sized, and the split-style layout offers privacy for owners and guests alike.Residents enjoy access to community amenities including a sparkling pool, fitness center, and more, all just steps from your front door. Situated at the corner of Howell Branch and SR-436, you’re minutes from shopping, dining, and major employers, with easy access to UCF, Full Sail, and Downtown Orlando.Whether you’re looking for a place to call home or a turnkey rental opportunity in a high-demand corridor, this one checks all the boxes. Priced at $140,000, schedule your showing before it’s gone.

2329 Coawood Unit 103, Maitland

$849,900

3 Beds ⋅ 3 Baths ⋅ Dixie Terrace SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Perfectly positioned between Maitland and Winter Park, this beautifully maintained 3-bedroom, 2.5-bath pool home offers an exceptional combination of charm, character, and an unbeatable location just minutes from the shops and restaurants of Park Avenue. Warm hardwood floors flow throughout the home, while the impressive two-story family room showcases soaring ceilings and a wood-burning fireplace that creates a welcoming gathering space. Separate living and dining rooms provide flexibility for both everyday living and effortless entertaining. The kitchen is thoughtfully designed with newer stainless-steel appliances and opens to the family room. French doors invite you outside to a private backyard retreat, while the adjacent sunroom is the perfect place to enjoy morning coffee with peaceful views of the pool and lush landscaping. Upstairs, you'll find three spacious bedrooms and two beautifully renovated baths. The primary suite is filled with natural light from a charming bay window and features a spa-inspired bath with marble floors, quartz countertops, dual vanities, and timeless subway tile. Step outside to your own backyard oasis. The covered lanai, complete with a summer kitchen, overlooks a newer saltwater pool and an expansive brick patio, creating the ideal setting for year-round outdoor living, entertaining, or simply unwinding in a private, tranquil setting. Adding to its appeal, the home is located just one house from the Winter Park city limits and is zoned for highly acclaimed Dommerich Elementary, Maitland Middle, and Winter Park High School. Enjoy the convenience of nearby Lake Lily, Enzian Theater, Maitland City Centre, and the boutiques, dining, and vibrant lifestyle of Winter Park's famed Park Avenue. This home offers the rare opportunity to enjoy a peaceful neighborhood setting with the very best of Maitland and Winter Park just moments away.

1783 Sunnyside Drive, Maitland

$1,150,000

5 Beds ⋅ 4 Baths ⋅ Maitland Club Rep SubDv. ⋅ 32751 Zip Code

Welcome to the Premier community of Maitland Club. The paver walkway and covered front patio lead you into the spacious foyer, featuring the elegant formal living and dining rooms with hardwood floors, crown molding and plantation shutters. The Kitchen features Granite countertops, 42” cabinets and lots of natural light. The warm and inviting family room area offers a woodburning fireplace with built-in shelving and an open floor plan. The 1st Floor Master has a Large Walk-in closet and master bathroom. Separate shower and Granite countertops. Upstairs boasts a Bonus Room, ample built-in storage, and a 5th Bedroom with a large Walk-in closet. Vaulted Ceilings throughout. The Screened Pool, Covered Lanai, and Large Fenced yard are great for entertaining. The community offers tennis and basketball courts and a 24-hour guard gated community. New roof in 2024 ($80,000 value). The carpet in the home was replaced in 2020.New A/C replacement in 2024.Termite bond which is transferable. TV's convey with the home in the living room. Pool has been resurfaced. The master bath and kitchen have been updated. Move-In Ready. This home is located within minutes of downtown Winter Park, Maitland Town Center, shopping, restaurants, hospitals, Genesis Health Club and easy access to I-4.

900 Brightwater Circle, Maitland

$559,900

3 Beds ⋅ 2 Baths ⋅ Forest Brook 5th Sec SubDv. ⋅ 32751 Zip Code

This beautifully redesigned and renovated move in ready pool home sits on a quiet cul-de-sac in desirable Maitland. Inside, the open floor plan features a brand-new kitchen with quartz countertops, shaker cabinetry, waterfall island, and stainless-steel appliances. Luxury flooring, remodeled baths, and modern finishes run throughout. Major updates include a new roof, newer HVAC, newer water heater, and French doors that open to a large backyard oasis. A bonus room with a mini split AC offers flexibility for an office or gym. Enjoy the private pool, patio, and proximity to top schools, shopping, and dining.

726 Forest Glen Court, Maitland

$375,000

3 Beds ⋅ 2 Baths ⋅ Lakewood Shores SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Sensational ALL-Block Home in Maitland with NO HOA and Deeded Private Lake Access! Nestled within Lakewood Shores, a charming and welcoming enclave of 42 homes, this 3BR/2BA residence offers a leisurely lifestyle with deeded access to Lake of the Woods via private neighborhood boat ramp. Venture inside to discover an openly flowing traditional layout, soft natural light, well-equipped kitchen w/skylights, separate dining area, and a cozy living room with a wood-burning fireplace. Each bedroom is generously-sized, while the primary bedroom has an en suite w/step-in shower. Enjoy the entertaining possibilities of the screened-in lanai, as well as the fenced-in backyard boasting a shed with electricity connected. Other features: attached carport w/newly epoxy floors, indoor laundry area, new electrical service panel, updated windows/plumbing/water heater, cost-savings well sourced irrigation system, near Maitland Art Center, Lake Lily Park, and the Enzian Theater, close to Downtown Maitland, Park Avenue, Winter Park Village, I-4, and much more! Call and schedule your private showing today!

110 N Lakewood Circle, Maitland

$945,000

5 Beds ⋅ 3 Baths ⋅ Dommerich Hills SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Welcome to this impressive 5-bedroom, 3-bath split-level POOL home in desirable Dommerich Hills, perfectly nestled on a generous 0.34-acre lot backing to a quiet creek and scenic green space.. Enjoy exceptional privacy and natural beauty with no rear neighbors, creating a peaceful backyard retreat. This remarkable residence offers almost 3400 square feet of living space, providing plenty of room for family living and entertaining. Thoughtfully designed, the home features expansive gathering areas, comfortable bedrooms, and inviting indoor-outdoor living spaces that take full advantage of the beautiful backyard setting. The stunning living room showcases cathedral ceilings with beautiful tongue-and-groove wood detailing, wood burning fireplace creating a warm and inviting atmosphere. French doors open to an expansive outdoor deck overlooking the large backyard and sparkling pool, seamlessly blending indoor and outdoor living. The well-equipped, efficient kitchen is designed for both everyday living and entertaining; appointed with custom shaker cabinetry, granite surfaces, and premium stainless steel appliances serves as the heart of the home. The kitchen boasts a separate breakfast room, with a large picture window capturing beautiful views of the backyard and pool, filling the space with natural light. The oversized primary suite serves as a private retreat, featuring French doors that open to the outdoor deck, an updated en-suite bath, and a large walk-in closet. The secondary bedrooms and guest bath on this level are generously sized and offer ample closet space, providing comfort and flexibility for family members or guests. Downstairs features a spacious family room with a cozy fireplace, two bedrooms, a full guest bath, and a convenient laundry room PLUS wonderful storage room. French doors open to a charming brick terrace overlooking a beautifully manicured backyard that backs onto a peaceful creek. The outdoor space also includes a large swimming pool and a life-size chess/checkerboard area, creating an ideal setting for relaxation and family fun! Recent improvements include windows replaced (2008, 2009), travertine and wood flooring, roof replaced in 2020, A/C' dates2022/2007, freshly painted exterior, and a new sewer connection completed in 2025. A detached two-car garage and long driveway provide abundant parking space, easily accommodating multiple vehicles and making it ideal for guests, recreational vehicles, or a growing family. Ideally located just a short bike ride from highly regarded Dommerich Elementary and Maitland Middle School. Conveniently located just minutes from downtown Maitland, Winter Park, premier shopping, dining, and major roadways, providing easy access to everything Central Florida has to offer. This one-of-a-kind property combines space, privacy, character, and convenience in one remarkable package. Schedule your private showing today and experience all this exceptional home has to offer.

624 Tuscarora Trail, Maitland

$570,000

4 Beds ⋅ 2 Baths ⋅ English Woods SubDv. ⋅ 32751 Zip Code

Welcome to 2494 Castlewood Road, a beautifully updated pool home situated on a spacious corner lot in one of Maitland's most established neighborhoods. This move-in-ready residence offers peace of mind with a newer roof, solar panels, updated HVAC, and extensive interior renovations throughout. Inside, you'll find an open and inviting floor plan featuring luxury vinyl flooring, updated bathrooms, modern fixtures, quartz countertops, and custom cabinetry. The spacious primary suite includes a walk-in closet and renovated en-suite bath, while the additional bedrooms provide flexibility for family, guests, or a home office. A large screened Florida room overlooks the backyard and creates the perfect space for year-round entertaining. Outside, enjoy the oversized swimming pool, expansive patio deck, fully fenced yard, and storage shed, offering plenty of room for recreation and outdoor living. Conveniently located just minutes from Downtown Maitland, Winter Park, Park Avenue, AdventHealth, shopping, dining, and major roadways including I-4, this home combines modern updates, energy-efficient features, and an exceptional location in the heart of Central Florida.

2494 Castlewood Road, Maitland

$1,360,000

4 Beds ⋅ 3 Baths ⋅ Kings Row SubDv. ⋅ 32751 Zip Code

New Price!! Beautifully updated pool home in the sought-after King's Row, Maitland community. This home blends timeless character with modern finishes. The corner lot residence features a three wide driveway, freshly updated landscaping and a commercial grade in ground basketball goal. Exterior paint (2026) creates warm curb appeal. Inside, new wood floors throughout lead to an open living space anchored by an updated kitchen and a classic painted brick wall. The renovated kitchen features quartz countertops, custom cabinetry, pendent lighting, stainless appliances and an updated Fisher Paykel refrigerator. A large island provides seating for four makes entertaining quick and simple. An updated hall pool bath provides easy access for guests both inside and out. Steps away the multi tasked laundry/utility drop/zone is conveniently located off the rear double garage entrance. A commercial grade Speed Queen washer in the laundry/utility room assures your clothes will be clean. Also, an adjacent wall of cabinetry increases the incredible storage in the home. Not only in the front but in the back the corner lot offers an ample spaced backyard retreat. Added is a screened and covered lanai perfect for outdoor parties and gatherings as does the oversized in-ground pool. Zoysia grass/lush landscaping and lighting continue the resort feel. A newer, horizontal stained wood fence adds privacy while maintaining charm. Back inside the living room, a rattan light fixture adds to the ambiance of this bright natural light space. Next to the living space, an office that features a set of French doors lends a place for quiet conversation. The generously sized family room with the afore mentioned painted brick wall is complete with large windows overlooking the sparkling pool and views of three whimsical palms. Down the hallway the newly installed designer wood flooring continues to all bedrooms. Every bedroom just received fresh paint, as well as the newly installed wood floors. All closets feature custom built-ins that add to the level of sophistication/quality in this home. The primary bedroom features another custom painted brick wall with updated sconce lighting. Still another set of French doors lead out to the pool and lanai. The owner's bath features a double vanity with stone counter-tops and updated lighting and faucets. A Mitered frameless glass shower is a great addition to the richness of the space. Zoned for Dommerich Elementary, Maitland Middle, Ninth Grade Center and Winter Park High the schools are highly desirable. A quick and easy close can be the start of your next chapter. This Move-in ready home awaits......

1615 King Arthur Circle, Maitland

$615,000

4 Beds ⋅ 2 Baths ⋅ Forest Brook 5th Sec SubDv. ⋅ 32751 Zip Code

Welcome to 741 Brookside Road in the heart of Maitland! This beautifully updated 4-bedroom, 2-bath pool home offers the perfect blend of modern upgrades, spacious living, and an unbeatable location. No expense was spared during the home's extensive renovations, creating a truly move-in-ready property that combines quality craftsmanship with timeless style. The recently remodeled kitchen is a true showpiece, featuring solid wood cabinetry, elegant Taj Majal granite countertops, upgraded appliances, and abundant workspace for cooking and entertaining. Recent improvements throughout the home include fresh interior paint, a newly renovated guest bathroom, updated plumbing, and a new roof installed in 2024, providing peace of mind for years to come. At the heart of the home is an enormous Florida Room, offering exceptional space for gathering with family and friends while overlooking the tropical backyard retreat. Step outside to your private oasis, complete with a sparkling pool and fountain surrounded by lush landscaping that creates a serene, resort-style atmosphere. Situated on a large fenced corner lot with no HOA, this property offers both privacy and freedom. Its fantastic Maitland location places you just minutes from shopping, dining, parks, and major roadways, making everyday living both convenient and enjoyable. You will be hard-pressed to find another property in this location and price range that offers this level of attention to detail, quality of construction, and thoughtful upgrades throughout. Every improvement has been carefully selected to create a home that is as functional as it is beautiful. Move-in ready and loaded with updates, this rare opportunity combines comfort, style, and outdoor living in one exceptional package. Schedule your private showing today and discover everything this beautiful Maitland home has to offer! Square footage includes Florida Room of 336 square feet not included on tax records.

741 Brookside Road, Maitland

$429,900

3 Beds ⋅ 2 Baths ⋅ Villas Lake Destiny SubDv. ⋅ 32751 Zip Code

This beautifully positioned residence offers an open and inviting layout designed for easy living and entertaining. Enjoy peaceful water views of Lake Destiny with no rear neighbors, creating a private backdrop and a rare sense of space and tranquility. Whether relaxing indoors or stepping outside, the serene setting delivers a true sense of comfort and escape. The home also features a spacious 2-car garage, providing convenience and additional storage. Thoughtfully updated and move-in ready, this home offers valuable recent improvements including a new A/C unit (2022), water heater (2022), tile roof replacement (2022), updated paint and modern light fixtures (2023), and both bathrooms beautifully renovated in 2021. The kitchen is complemented by newer appliances, adding both style and functionality. Step outside and enjoy even more value with the outdoor deck currently being replaced, creating an enhanced outdoor living space to take in the beautiful lake setting. Residents enjoy access to exceptional community amenities including a pool, tennis courts, and access to Lake Destiny, all within a dog-friendly community designed to support an active and enjoyable lifestyle. Ideally located with quick access to major highways, dining, shopping, business centers, and everything Maitland and the greater Orlando area have to offer, this property delivers the perfect blend of lifestyle and accessibility. Whether enjoying your morning coffee overlooking Lake Destiny or coming home after a busy day, this residence offers the privacy, views, updates, and location today’s buyers are searching for.

1010 Winderley Place Unit 149, Maitland

$419,900

2 Beds ⋅ 2 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code

Virtually Staged. RARE LAKEFRONT opportunity to Live right on LAKE MAITLAND! Sip your morning coffee with one of the most premier views in the entire community! BONUS: It's on the main FIRST floor, so NO STAIRS! Just a pure unencumbered view of Lake Maitland right from your living room! And only a few steps to the dock or community pool!! This unit has the EXTRA HALF BATHROOM and has been tastefully updated to accentuate it's incredible mid century modern original features, that are in immaculate condition! There may never be another unit quite like this one! The high end plantation shutters offer privacy when needed, but can stay wide open for that view! Enjoy the remodeled Community POOL & Clubhouse all on the stunning water front of Lake Maitland which is also connected to the Winter Park Chain of Lakes. Plenty of fishing, fun and relaxing to be had on the community dock, shuffleboard and putting green! So many amenities nestled amongst the towering shade trees and mature landscaping. The Mid Century Modern architecture is about as timeless of a look that you can find that fits the Maitland/Winter Park lifestyle. You couldn't ask for a better location at just minutes from downtown Winter Park, Park Ave, SunRail station and all the restaurants surrounding the 17/92 Maitland/Winter Park Corridor. All Units recently had metal roof replacement in 2025 and were just freshly painted as well. It's completely move in ready with all New Luxury Vinyl Plank Flooring, Kitchen and bathroom updates,. This unit has not been available for many years, so don't miss out on this view!

1140 S Orlando Avenue Unit H3, Maitland

$800,000

3 Beds ⋅ 3 Baths ⋅ Lakewood Shores 1st Add SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Nestled on the shores of skiable Lake of the Woods, this beautifully maintained 3-bedroom, 2 and a half bath waterfront residence offers over 105 feet of private lake frontage with breathtaking open-water views. Designed for those who embrace the lake lifestyle, the property features a private boat launch, two docks, and a solar-powered boat lift, providing effortless access to one of Central Florida's most desirable private lakes. Inside, vaulted ceilings and abundant natural light create an inviting atmosphere, while the updated kitchen opens seamlessly to the living and dining spaces, making everyday living and entertaining a pleasure. The primary suite enjoys peaceful water views, and the home's coastal-inspired finishes enhance the relaxed lakefront setting. A spacious rear deck overlooks the water and serves as the perfect place to enjoy sunrise coffee, sunset gatherings, and weekends on the lake. Additional highlights include a durable metal roof, wood floors, mature landscaping, generous outdoor living spaces, and a prime Maitland location convenient to shopping, dining, top-rated schools, Winter Park, and Downtown Orlando. Rarely does an opportunity arise to own a move-in ready waterfront home with this combination of frontage, amenities, and direct access to skiable waters.

195 Cedarwood Drive, Maitland

$295,000

2 Beds ⋅ 2 Baths ⋅ Sun Bay Club Condo Ut 1 SubDv. ⋅ 32751 Zip Code

Ground-floor 2BR/2BA in the gated, lake-access community of Sun Bay Club in Maitland, FL — updated and move-in ready! The kitchen was renovated in 2023 with new cabinets, quartz countertops, and updated appliances (microwave 2024, dishwasher 2025). Both bathrooms were updated in 2026: the primary with a new double-sink vanity, modern lighting, and a pocket door for privacy, and the hall bath with a new vanity, mirror, and lighting. Durable wood-look tile and wood flooring throughout — no carpet. This is a two-story building, which falls outside Florida's SIRS and milestone inspection requirements that apply to condos three stories and taller. The open-concept living space extends through sliding glass doors to an enclosed sunroom overlooking the pond, ideal as a home office or morning coffee spot, and each bedroom opens to its own private screened patio. The primary suite adds a walk-in closet with built-in shelving; the second bedroom offers double closets with built-in shelving as well. HOA fee includes cable/internet, lake access for boats and jet skis, a large lakefront pool, a tennis court, and all exterior maintenance, including the roof. Minutes to Maitland and Winter Park shopping and dining, and easy access to highway I-4. Great option for low maintenance living as a primary residence or an investment opportunity. Schedule a viewing today!

1000 Winderley Place Unit 141, Maitland

$638,900

3 Beds ⋅ 3 Baths ⋅ Enclave At Maitland A-F SubDv. ⋅ 32751 Zip Code

"PRICE IMPROVEMENT" ON THIS MOVE-IN READY 3-BED, 2.5-BATH SINGLE FAMILY HOME IN THE "EXCLUSIVE GATED COMMUNITY OF ENCLAVE AT MAITLAND", FL 32751. Nestled within the highly sought-after & gated community of Enclave at Maitland, Single Family Homes rarely come on the market and this home offers a Luxury Interior Footprint that's a perfect balance of privacy, elegance, and convenience. Fully updated & loaded with high-end finishes, the triple split-plan layout features separate Formal Dining & Family Rooms that maximize both entertaining and day-to-day privacy. Enter through a HUGE 21' Long Foyer into the Large Family Room which boasts a 14' High Tray Ceiling and the Centerpiece of the home. Just off the Family Room is the Formal Dining room, perfect for entertaining & family dinners. The Kitchen is perfectly designed for the Serious Chef, boasting Level 3, 42" Maple Cabinetry with Upper Crown Molding, Premium Granite, Center Island with a (3) Person Breakfast Bar, Stainless Appliance Package including Double Built-In Ovens, French Style Refrigerator, Flat-Top Range, Tons of Counter & Storage Space, Dual Stainless Sink, Custom Tile Backsplash, Pendant & Recessed Lighting, Closet Pantry and an adjoining Sunlit Dinette that provides the perfect spot for casual morning coffee. The Primary Suite is the Perfect Couples Retreat! The Bedroom is generous in size and will accommodate all of your oversized furniture & features a HUGE Tray Ceiling, Crown Molding, Laminate flooring, and Dual Walk-In Closets outfitted w/Custom Storage Organizers. The En-Suite Bathroom offers His-and-Her Maple Vanities w/Undermount Sinks, Granite Counters, Deep Garden Soaking Tub wrapped in Custom Tile, Large Walk-In Shower engineered with Dual Shower heads at opposite ends, Under-Cabinet Accent Lighting and a Glass Block Window for lots of natural lighting. On the opposite side of the residence, Two Additional Bedrooms share a beautifully appointed Full Bathroom, offering an ideal setup for Children & Guests. If you work from home or just looking for a quiet space, you'll enjoy the Private Office/Den located just off the Family Room. The Interior Laundry Room is highly functional and included Front-Load Washer & Dryer, Integrated Wash Tub/Sink & Upper Storage Cabinets. Your living space effortlessly expands outdoors through a Triple-Slider to the 12'x16' Covered Back Porch w/Premium Slate Tile flooring. Here, you can unwind against the peaceful backdrop of an unobstructed Lake View & Conservation Area. Additional Features: Prestigious Maitland Lifestyle, Low-Maintenance Luxury, Directly Across from the Pool, Block & Stucco, Barrell Tile Roof, Freshly Painted Inside & Out, High Ceilings Throughout, Carrier HVAC (2021), Vacuflo Central Vac System, GE Hybrid 50 Gal Water Heater (2016), Double-Paned Windows, 18x18 Tile Flooring Flowing Diagonally, Premium 8" Crown Molding, Elegant Custom Arches, Tray Ceilings, 8’ High Doors, Upgraded 6" Baseboards, Surround Sound Speaker & Prewire, Security System, Ceiling Fans/Light, Pre Plumbing for Summer Kitchen, Epoxy Coated Garage Floor and (2) Garage Door Openers, Custom Garage Storage, Paver Driveway, Beautiful Palms, Magnolias & Ivy, Private Mailbox, Irrigation System and more. Incredible location close to I-4, Downtown Maitland, Altamonte & Orlando, Shopping, Dining, Theme Parks, Turnpike, Beaches and all Central Florida has to offer. Call today for more info or schedule a private showing. This is Move-In Ready Perfection!

1404 Caring Court, Maitland

$1,095,000

4 Beds ⋅ 4 Baths ⋅ Maitland Club Rep SubDv. ⋅ 32751 Zip Code

This elegant Mediterranean-inspired one-story residence is in the gated community of Maitland Club overlooking a tranquil pond. A well maintained 4 bedroom, 4 bath Plus home office with recent updates that include a new roof, hot water heater, pool heater, and a re-pipe. The home features a soft neutral interior palette throughout with an elegant formal living room filled with natural light featuring soaring ceilings and a dramatic wall of arched windows and French doors overlooking the outdoor living area. The dining room and home office are just off the entry foyer. The home office offers a warm workspace with hard wood flooring, custom bookcases and cabinetry. This room could be a temporary guest room it features a closet and is adjacent to the pool bath. The kitchen offers generous workspaces with extensive cabinetry, solid surface countertops, a center island, and a breakfast bar overlooking the family room. The open concept includes a planning desk and a casual dining space overlooking the pool. The spacious family room is designed for comfortable everyday living and effortless entertaining, featuring high ceilings, recessed lighting, and a fireplace framed by custom built-in audio-visual cabinetry. An oversized primary suite with a dramatic tray ceiling and expansive sitting area creates a true retreat-like atmosphere with an en-suite attached that features a large double vanity with dressing table, a relaxing garden tub and a large walk-in shower. On the opposite side of the home find three generous sized guest rooms and two full baths, laundry and hall to three car garage. The sparkling pool with tiered entry steps is surrounded by an expansive covered patio offering multiple seating and dining areas, all overlooking a lovely pond. Roof, Garage Floor and Pool heater warranties are available upon request.

1911 Belford Court, Maitland

$184,900

2 Beds ⋅ 2 Baths ⋅ Visconti West Condo SubDv. ⋅ 32751 Zip Code

If you are looking for a terrific property, look no further! You or your tenant can live the lifestyle deserved in this RESORT-STYLE, video-monitored GATED COMMUNITY located on beautiful Lake Shadow in the heart of Maitland Center. This two-bed/two-bath, 2nd-story, CORNER UNIT features an OPEN floor plan with a LIVING/DINING COMBO and 9-FOOT CEILINGS. The KITCHEN includes a breakfast bar, closet pantry, INSIDE UTILITY CLOSET with washer and dryer, and neutral tile. All appliances convey at closing. DOUBLE MASTERS each offer an en-suite bath and a walk-in closet. The 20 X 20 living area provides lots of sunlight and features a built-in nook with glass shelving you can use as you choose. In 2024, the interior was painted, and carpet was installed. Through sliders, you can unwind at the end of a busy day on the SCREEN-ENCLOSED tiled LANAI and enjoy a TRUE ESCAPE. If extra storage is needed, a patio closet awaits! This GORGEOUSLY LANDSCAPED and PET-FRIENDLY community offers two LAKESIDE POOLS with Wi-Fi access, a club-quality FITNESS CENTER, grand CLUB ROOM with CATERING KITCHEN, fully-equipped BUSINESS CENTER, lighted TENNIS courts, BASKETBALL court, car wash area, two laundry facilities, 24-HOUR MAINTENANCE, WATER, SEWER, and a Monday-Friday VALET WASTE REMOVAL SERVICE. The condo community boasts a newer tile roof, reflecting ongoing care and investment in the property. Located minutes away from SR 414, I-4, 429, Routes 434 and 436; it is a quick drive to downtown Orlando, Cranes Roost Park, and to the upscale shopping and dining at Altamonte Mall, Altamonte Towne Center, Winter Park Village, and Winter Park’s quaint Park Avenue. Enjoy Florida living at its best! This property may be under audio & visual surveillance.

1440 Lake Shadow Circle Unit 8201, Maitland

$1,499,000

5 Beds ⋅ 4 Baths ⋅ Replat Blk B Poors Add SubDv. ⋅ 32751 Zip Code

A premier street offering an accessible lifestyle to Maitland’s vibrant downtown corridor, known for its community events, restaurants, Lake Lily Park, the beloved independent Enzian Theater and within view of Lake Sybelia. This custom home was completely rebuilt in 2007, adding significant square footage and incorporating a timeless transitional design. Five bedrooms, four baths, stretching across 4,814 square feet with bonus space, there are many ways to make it your own. Inspired by classic Charleston architecture with Florida influences, the exterior features French doors across the front and rear elevations, lantern-style lighting and a metal roof that enhance the home's charm while filling the interiors with natural light. Shutters and upper-level balconies at both sides of home complete the design. Enter inside to a sweeping staircase with elegant iron details, with neutral travertine flooring that flows throughout the main level and finished with volume ceilings. The kitchen, living and dining spaces blend seamlessly together, complemented by an additional sitting room with privacy doors that provide flexible living options. The kitchen features 42-inch custom cabinetry with glass-paneled doors, granite countertops, a farmhouse sink and high-end stainless-steel appliances. Generous laundry and pantry storage are bonus. The dining area showcases rich hardwood flooring, plantation shutters, built-in surround-sound speakers and direct access to outdoor living spaces. The first floor includes two bedrooms with a shared bath, along with an additional hallway guest bath. Upstairs, beautiful wood floors anchor the rooms, and the spacious primary retreat opens to a private balcony spanning across the back of home and with pool views. An expansive walk-in closet provides exceptional organization, while the primary bath features dual vanities, a rain shower with bench seating and a classic clawfoot tub. Additional upstairs laundry stack for convenience. Secondary bedrooms are spacious and full of light, and great closet storage and additional loft are a bonus. Outdoor living centers around a covered porch overlooking the pool, complete with travertine decking and dramatic fountain features. An additional pool house enhances the backyard and offers endless possibilities for guests, entertaining or a private workspace. Outdoor speaker system adds to the ambience. Additional improvements and features include a newer metal roof (2020), two HVACs (2021), water heater (tankless Rinnai installed by Maitland/Winter Park plumbing), plantation shutters throughout, a freshly painted interior, an extensive interior and exterior lighting package, and thoughtfully designed low-maintenance landscaping featuring front-yard turf, mature plantings and clean rock-bed borders. Exterior ceramic paint has a lifetime warranty. Main floor and primary suite have ceiling-installed concert speakers and outdoor speakers. Lower-floor speakers have individual room controls and are served by a pantry stereo system. This exceptional home offers a desirable location with convenient access to major roadways. Zoned for sought-after schools including Lake Sybelia Elementary, Maitland Middle School and Edgewater High School, a designated magnet school, Park Maitland elementary school, and JCC community center and school. A rare opportunity, this home is a standout in one of Maitland’s special neighborhoods.

255 W George Avenue, Maitland

$210,000

2 Beds ⋅ 2 Baths ⋅ Visconti East Bldg 27 SubDv. ⋅ 32751 Zip Code

Visconti Condo - Gated Community with lots of amenities only 8 miles from Downtown Orlando. This community situated on the north shore of Lake Shadow offers swimming pool, fitness center, clubhouse, tennis and basketball courts. Conveniently located close to I-4 and Maitland Blvd. Multi level home features an open floor plan with kitchen living/dining and office on main 2nd floor and 2 bedrooms 2 bathrooms on the 3rd floor. This home also features an attached 2 car garage with plenty of room for your vehicles or extra storage. HOA includes exterior maintenance, landscaping, valet trash, water, sewer and pest control.

2847 Shadow View Circle Unit 2847, Maitland

$440,000

3 Beds ⋅ 2 Baths ⋅ Pindar Sub SubDv. ⋅ 32751 Zip Code

Inside, the home opens into a bright and airy open-concept living space highlighted by high tray ceilings, recessed lighting, oversized glossy tile flooring, and an abundance of natural light. The seamless flow between the living, dining, and kitchen areas creates the perfect setting for both entertaining and everyday luxury living.

206 Moseley Avenue, Maitland

$590,000

4 Beds ⋅ 4 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code

The Enclave at Maitland (Montacino), Beautifully Updated, First Floor Primary Bedroom, Oversized 20' x 26' Garage, Gated Community Living in the Enclave at Maitland which is highly sought-after, offering the perfect blend of style, comfort, and maintenance-free living. This fully updated Spanish-style townhome features 4 bedrooms, 3.5 bathrooms, a private paver courtyard, and an oversized attached two-car garage measuring approximately 20' x 26'—providing valuable extra space for storage, hobbies, a workshop area, or larger vehicles. One of the home's most desirable features is the spacious first-floor Primary Suite, offering privacy and convenience along with a beautifully updated en-suite bath featuring dual vanities, a soaking tub, separate shower, and walk-in closet. The thoughtfully designed floor plan is enhanced by soaring 9'8" ceilings on the main level, extensive crown molding, ceiling fans, and abundant natural light throughout. At the heart of the home is a stunning remodeled kitchen featuring 42-inch cabinetry with crown molding, granite countertops, stainless steel appliances, breakfast bar seating, and a cozy breakfast nook overlooking the private courtyard. The kitchen, all bathrooms, and even the laundry room have been tastefully updated, providing a move-in-ready experience for the next owner. You've got to see it! Upstairs you'll find a second private suite with its own updated bathroom, two additional bedrooms, another full bath, and a conveniently located laundry room. Closet organizer systems throughout the home provide exceptional storage and functionality. Residents enjoy access to a resort-style community pool overlooking picturesque Lake Charity, all within the security and convenience of a gated neighborhood. Ideally located near Maitland Boulevard and I-4, this exceptional location provides easy access to Downtowns of Orlando, Maitland and Winter Park, with premier shopping, dining, entertainment, and major employment centers. Offering a rare combination of updated finishes, flexible living space, oversized garage storage, and an unbeatable location, this exceptional townhome is ready to impress even the most discerning buyers.

1149 Charming Street, Maitland

$119,900

Coffins SubDv. ⋅ 32751 Zip Code

Vacant parcel likely and ideally suitable for RV, Boat and other residential storage uses. Recorded 14' access easement to Ridgewood Avenue. Partially fenced parcel. Sign on property visible from Ridgewood Avenue. MOTIVATED SELLER WILL PROVIDE FINANCING TO QUALIFIED BUYER. LOW TAXES (Legal Description to be revised to reflect recent sale.)

Ridgewood Avenue, Maitland

$129,000

2 Beds ⋅ 1 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Bright and well maintained 2 bedroom, 1 bath condo located in a desirable shopping and dining area! This inviting home features abundant natural light, a spacious walk-in closet in the primary bedroom, and a relaxing enclosed patio perfect for additional living space or entertaining. The HOA includes water for added convenience. Residents also enjoy access to a community pool and low-maintenance living close to everything you need. Great opportunity for homeowners or investors alike!

550 Flemming Way Unit 100, Maitland

$489,900

3 Beds ⋅ 2 Baths ⋅ Winfield SubDv. ⋅ 32751 Zip Code

Welcome to 2155 Fennell Street, a beautifully renovated pool home nestled in the desirable Maitland community. This move-in ready residence has undergone an extensive transformation, offering the perfect blend of modern elegance, functionality, and Florida lifestyle living. From the moment you arrive, you'll appreciate the brand-new roof, new driveway, fresh exterior paint, and impressive curb appeal. Inside, soaring vaulted ceilings and abundant natural light create a bright and inviting atmosphere. The open-concept floor plan features luxury vinyl plank flooring throughout, designer lighting, and fresh interior paint. The fully remodeled kitchen is the heart of the home, showcasing quartz countertops, custom cabinetry, stainless steel appliances, and a spacious breakfast bar overlooking the main living areas. The primary suite offers a private retreat with a beautifully updated ensuite bath featuring dual vanities, designer finishes, and a stunning walk-in shower. Additional bathrooms have been tastefully renovated with modern fixtures and custom tile work. Step outside to your private backyard oasis complete with a resurfaced swimming pool, screened lanai, and fully fenced yard—perfect for entertaining, relaxing, and enjoying year-round Florida sunshine. Conveniently located near shopping, dining, parks, major highways, and top area amenities, this exceptional property offers the rare opportunity to own a truly turnkey home in one of Maitland's most sought-after locations. Schedule your private showing today and experience this stunning home.

2155 Fennell Street, Maitland

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