Maitland Homes for Sale

Maitland Homes for Sale

Welcome to Maitland, Florida – a charming city that perfectly blends suburban tranquility with vibrant urban amenities. Nestled in the heart of Orange County, Maitland is renowned for its picturesque lakes, lush parks, and a strong sense of community. With a rich history dating back to the 19th century, this city boasts a unique character that appeals to families, professionals, and retirees alike.

Maitland is home to an array of cultural attractions, including the Maitland Art Center, which showcases beautiful murals and sculptures, and the Enzian Theater, a beloved independent cinema that hosts film festivals and community events. The city’s beautiful parks, such as Lake Lily Park and the scenic trails along the Chain of Lakes, offer ample opportunities for outdoor recreation, from picnicking to kayaking.

For those considering a move to this delightful area, Maitland offers a diverse selection of homes for sale. Whether you’re looking for a charming bungalow, a modern townhouse, or a spacious family home, you’ll find options that cater to every lifestyle and budget. The real estate market here is thriving, with properties often featuring stunning architectural designs, manicured lawns, and proximity to top-rated schools and amenities.

Living in Maitland means enjoying a peaceful suburban lifestyle while being just a short drive away from the bustling attractions of Orlando. With its friendly neighborhoods, excellent dining options, and abundant recreational activities, Maitland is not just a place to live; it’s a place to thrive. Explore the homes for sale in this enchanting city and discover your perfect sanctuary in Maitland, Florida!

Newest Maitland Homes for Sale

2607 Derbyshire Road, Maitland
$519,900
3 Beds ⋅ 2 Baths ⋅ Indian Hills Unit 1 Rep SubDv. ⋅ 32751 Zip Code
Welcome to this beautifully updated, single-story pool home in the established, non-HOA Indian Hills neighborhood of Maitland! The updated kitchen features Carrara quartz countertops, an undermount sink with a pull-down faucet, and a new stainless steel appliance package. Both bathrooms have been tastefully renovated with shaker-style vanities topped with quartz, dual undermount sinks, framed mirrors, new toilets, and modern fixtures. Additional interior updates include new luxury vinyl plank flooring, new carpet, and fresh two-tone interior paint. Outside, enjoy fresh exterior paint and a private in-ground pool with a newly sealed and painted pool deck. The rear porch also features new carriage-style lighting. Conveniently located near SR-436 and US-17/92, this home offers easy access to Maitland, Winter Park, Altamonte Springs, and downtown Orlando.

2607 Derbyshire Road, Maitland
1553 Glastonberry Road, Maitland
$369,999
3 Beds ⋅ 2 Baths ⋅ Northgate SubDv. ⋅ 32751 Zip Code
A private Maitland retreat with nearly half an acre of possibilities! Set on a lush, fully fenced 0.46-ACRE-LOT with mature landscaping and exceptional privacy, this unique 3-bedroom, 2-bath home offers expansive indoor and outdoor spaces designed for relaxing and entertaining. Inside, recessed halogen lighting is featured throughout, along with a separate flex/game room approximately the size of a bedroom. The flex room includes a television and foosball table. A large garage provides generous parking and bonus storage cabinets. The backyard is the true showpiece. A 500-square-foot covered and screened porch features a built-in 14-foot slate bar with cabinets plus a full wet bar behind it. Lighted paved walkways lead to a 400-square-foot wood deck with a roof covering, built-in stainless-steel grilling area, and extra-large hot tub. A built-in firepit and three-tiered garden area complete this private outdoor oasis. With no neighboring homes visible from the backyard, the property offers a rare sense of seclusion. Gated access provides space to park multiple boats, trailers, or other recreational vehicles. The expansive yard may also offer room for a swimming pool and potential additional residential development, subject to county approval. Featuring a long driveway, generous outdoor space, and a private setting that is increasingly difficult to find, this Maitland property presents an exciting opportunity to create something special. Bring your vision and make this remarkable backyard retreat your own!

1553 Glastonberry Road, Maitland
389 Sultana Lane, Maitland
$769,000
3 Beds ⋅ 2 Baths ⋅ Druid Hills Park SubDv. ⋅ 32751 Zip Code
Welcome to this beautifully renovated 3-bedroom Maitland pool home, featuring a spacious additional room ideal for a large 4th bedroom, home office, or bonus room, along with an expansive backyard perfect for outdoor living and entertaining. Blending timeless charm with modern sophistication, this thoughtfully updated, move-in-ready residence showcases designer finishes and the perfect balance of character, comfort, and contemporary style. Step inside to discover stunning original hardwood floors that have been meticulously refinished, complemented by updated flooring, interior doors, baseboards, and modern hardware. The beautifully renovated kitchen showcases a hand-assembled Italian luxury gas range with custom plaster hood, stylish finishes, and thoughtful upgrades, while the remodeled primary bathroom offers a fresh, elevated design. Extensive improvements provide both style and peace of mind, including new windows (2025), fresh exterior paint (2026), new gutters (2026), and updated plumbing, electrical, and much more. The exterior has been equally transformed with refreshed landscaping, new sod (2026), a newly installed driveway and walkway, and a new storage shed. The expansive backyard offers an inviting setting for entertaining, relaxing by the pool, gardening, or creating your own private outdoor retreat. With its extensive renovations, designer details, flexible living spaces, and exceptional outdoor setting, this Maitland property offers a rare opportunity to enjoy the charm of an established home with the convenience of modern updates. Schedule your private showing today!

389 Sultana Lane, Maitland
1951 Mohican Trail, Maitland
$925,000
5 Beds ⋅ 3 Baths ⋅ Windsor Park SubDv. ⋅ 32751 Zip Code
Welcome to this charming five-bedroom, three-bath home on an oversized corner lot in the desirable Dommerich community! Featuring a versatile split-bedroom floor plan, an attached in-law suite with private entrance/own bath, and a private pool with a spacious backyard, this home combines comfortable living spaces with a location that makes everyday life convenient. Inside, engineered wood floors, wood blinds and crown molding add warmth and character throughout. The living room features a wood-burning brick fireplace, while the kitchen offers white cabinetry, granite countertops, stainless steel appliances and a farmhouse sink. The open kitchen and family room create a welcoming space for gathering and entertaining. The split-bedroom layout provides added privacy, while the attached in-law suite offers flexibility for multigenerational living, guests or a private retreat. Go outside to enjoy the fenced backyard and in-ground pool, ideal for relaxing and entertaining year-round. Updates include a 2023-roof, 2023 renovation (added third bath and in-law suite/flex space), 2026 new interior doors, 2026 new ceiling and insulation in garage, and 2026 updated landscaping. A rare feature in Dommerich, this home has natural gas service powering the water heater and furnace with additional opportunities to connect a gas range, dryer, outdoor grill, pool heater and more. Location is another standout feature. Directly across from a recreational and biking path providing access to Dommerich Elementary School and Maitland Middle School, this home offers a wonderful opportunity to enjoy the surrounding community and outdoor lifestyle. With easy access to downtown Maitland, Interstate 4, Maitland Community Park, Dommerich Elementary and Maitland Middle Schools, this home is must-see.

1951 Mohican Trail, Maitland
1741 Lyndale Boulevard, Maitland
$699,000
3 Beds ⋅ 2 Baths ⋅ Dixie Terrace Ut No 2 SubDv. ⋅ 32751 Zip Code
Virtually Staged. Less than a ten-minute drive from downtown Winter Park, Park Avenue’s shops and restaurants, and Rollins College, this completely renovated home has updates well beyond the finishes. Built in 1943 with solid block construction, it features new electrical, plumbing, central air conditioning, Jeld-Wen windows, and a tankless water heater. A wood-burning fireplace anchors the cozy living room, and the spacious renovated kitchen features white cabinetry, quartz countertops, stainless steel appliances, and a large island with seating for casual dining. The converted garage provides additional living space for a formal dining room or extra family room. Two secondary bedrooms share a renovated hall bathroom with a walk-in shower and rain showerhead. The spacious primary suite includes a custom walk-in closet and a renovated bathroom with double sinks, quartz countertops, and a walk-in shower with a rain showerhead. Sliding glass doors open from the suite to the back patio and fire pit area, with a huge backyard offering plenty of space for outdoor dining, entertaining, and play, plus room to explore adding a pool or expanding the home in the future. Zoned for Dommerich Elementary, Maitland Middle, and Winter Park High School, this home puts some of the area’s favorite destinations close to home, including Lake Lily Park, Maitland’s cultural attractions, and the shops and dining along Park Avenue. Call today to schedule a private showing!

1741 Lyndale Boulevard, Maitland
356 Croton Drive, Maitland
$515,000
4 Beds ⋅ 2 Baths ⋅ Druid Hills Park SubDv. ⋅ 32751 Zip Code
This residence exemplifies pride of ownership, boasting a beautifully appointed kitchen with high-quality, updated cabinetry and granite countertops, complemented by upper-end stainless steel appliances, Upon arrival, the exceptional workmanship evident in the pavers driveway is immediately apparent, and this attention to detail extends to the nicely landscaped backyard. complete with a paver patio. Home has fresh paint inside and out. New carpet in the bedrooms. The roof was installed in September 2020. Prospective buyers may be interested in assuming the seller's 2.76% interest loan.

356 Croton Drive, Maitland
2122 Korat Lane, Maitland
$385,000
4 Beds ⋅ 2 Baths ⋅ Winfield Ut 2 SubDv. ⋅ 32751 Zip Code
Welcome to Winfield! This inviting home offers a thoughtful layout with comfortable spaces for relaxing, gathering, and entertaining. Step into a separate front living room, perfect for greeting guests or enjoying a quiet moment. The home flows into a beautiful kitchen featuring a breakfast bar and cozy dining area, with views into the family room to keep everyone connected. The split-bedroom floor plan provides a private primary suite on one side and two additional bedrooms on the other. The primary suite features an en-suite bathroom with a separate tub and shower. A versatile bonus room offers space for a home office, hobby room, or creative retreat. Step outside to a screened patio, ideal for shaded relaxation, overlooking a spacious backyard ready for weekend grilling and outdoor gatherings. Located in the desirable Winfield community, where HOA fees contribute to community exterior maintenance. This home offers convenient access to major roadways, including SR 434, SR 414, SR 429 and I-4 making commuting to Maitland, Altamonte Springs, Winter Park, and downtown Orlando more accessible. Enjoy convenient access to nearby destinations, including RDV Sportsplex, Maitland Business Center, Altamonte Mall, Wekiwa Springs State Park, and Trotters Park. With shopping, recreation, dining, and major commuter routes nearby, this Winfield home offers a convenient Central Florida lifestyle.

2122 Korat Lane, Maitland
616 Lake Howell Road, Maitland
$550,000
4 Beds ⋅ 2 Baths ⋅ Forest Brook 2nd Sec SubDv. ⋅ 32751 Zip Code
Welcome to modern elegance in the heart of Maitland! This beautifully renovated home offers the perfect blend of timeless charm, contemporary finishes, and inviting living spaces. From the moment you arrive, you’ll be welcomed by a charming covered entryway featuring warm wood ceiling accents, and a beautiful sage green front door. Step inside to discover a bright, open atmosphere with gorgeous light wood flooring, fresh neutral tones, recessed lighting, and thoughtfully selected designer finishes throughout. The beautifully updated kitchen is a true showstopper, featuring warm wood cabinetry, Taj Mahal quartz countertops, elegant brass hardware, stainless steel appliances, a custom range hood, and a spacious peninsula with bar seating. Designed with both style and functionality in mind, this kitchen is perfect for entertaining and everyday living. The inviting living area features a stunning brick fireplace that adds warmth and character, while the beautifully updated bathrooms showcase modern vanities, stylish tile work, and sophisticated fixtures. The spacious bedrooms offer comfort and natural light, creating peaceful retreats throughout the home. Outside, enjoy a welcoming exterior, a spacious front yard, and an attached two car garage. Location, Location, Location! Ideally situated in the highly desirable Maitland area, this home offers convenient access to Winter Park, Downtown Orlando, shopping, dining, parks, and major roadways. With its beautiful renovations, modern finishes, and prime Central Florida location, this home is truly a must-see! Schedule your private showing today and experience everything this Maitland gem has to offer!

616 Lake Howell Road, Maitland
140 Windglow Trail, Maitland
$899,000
4 Beds ⋅ 3 Baths ⋅ Windgrove SubDv. ⋅ 32751 Zip Code
Virtually Staged. New to the market, this amazing 2 story 4 bedroom and 3 bath Maitland home has just finished a full remodel! This home has an open floor plan which features classic elegant design style synonymous with Quarter Circle TO designs. Walking into the home, you will immediately notice the elegance. The whole home features luxurious wood style flooring, custom brick, and accent walls. All bathrooms feature waterfall showerheads and glass doors with gold finishes. The spacious and decked out kitchen features: White shaker cabinets, Quartz countertops, an island with a waterfall quartz counter top, double oven, modern cook top with stylish custom designed hood, farmhouse sink, touch screen WIFI refrigerator, wine rack, and gold hardware throughout. The spacious living room/dining room is great for hosting formal dinner parties or informal movie nights. The second living room is perfect for entertaining with a sliding glass door to the back yard and the bistro with 2 wine coolers nearby. The back yard boasts an oversized patio and a fire pit, which is fully fenced for privacy. There is an additional living room and space for an office on the second floor. This home showcases a beautiful staircase with tempered glass railings, motion sensor LED lighting up the stairs, and a 6 tier crystal chandelier. The Primary Suite features a walk-in closet and spa-like bathroom, highlights a modern bath tub, luxury shower containing waterfall and body shower heads. The fourth bedroom has French doors and its own entry to the incredible backyard. Easy access to lakes, restaurants, and shopping nearby. This home contains features of a million dollar home at this amazing price. This is a must see!

140 Windglow Trail, Maitland
2514 Tuscarora Trail, Maitland
$879,000
4 Beds ⋅ 3 Baths ⋅ Dommerich Hills Second Add SubDv. ⋅ 32751 Zip Code
$5000! CLOSING-COSTS CREDIT AVAILABLE! Qualified buyers who finance through our preferred lender will receive a $5,000 lender credit toward closing costs. Buyer must qualify restrictions apply. Welcome to 2514 Tuscarora Trail, a beautiful, fully renovated lakeview pool home nestled in the heart of Maitland, Florida! This spacious single-story residence offers 4 bedrooms, plus a bonus/flex room, 3 bathrooms, and approximately 3,000 square feet of living space on a generous 0.43-acre lot. Step inside to discover an inviting open floor plan featuring spacious living and dining areas, a brand new gourmet kitchen, and plenty of natural light. The thoughtfully designed layout provides comfortable spaces for everyday living and entertaining. This home features a brand new HVAC unit, 2024 roof, the home has been fully repiped, including the all sewer lines. Step outside to your own private retreat, featuring a sparkling swimming pool, covered patio, expansive backyard, and peaceful lake views. Whether relaxing poolside or hosting outdoor gatherings, this property offers an exceptional Florida lifestyle. Additional highlights include a complete paid for solar panel system, ample parking, and convenient access to Winter Park's popular shopping, dining, entertainment, and recreational destinations. Enjoy the perfect combination of space, comfort, outdoor living, and a convenient Central Florida location. Schedule your private showing and discover everything this Maitland property has to provide.

2514 Tuscarora Trail, Maitland
2141 Falkner Road, Maitland
$510,000
4 Beds ⋅ 3 Baths ⋅ Winfield SubDv. ⋅ 32751 Zip Code
Discover the charm and convenience of Maitland living in this four-bedroom home featuring two full bathrooms and one half bathroom. A large, beautiful patio creates an inviting setting for outdoor dining, entertaining, or simply relaxing, while the fenced yard adds privacy and space to enjoy the outdoors. Newer roof, brand new flooring throughout. New Bathroom cabinetry. Interior and exterior new paint. Located at 2141 Falkner Road, this home offers the added convenience of I-4 just around the corner, making travel throughout Central Florida easy. Everyday essentials and local attractions are within approximately a seven-mile radius, including Publix at Gateway Crossing, nearby gas stations, and the restaurants and cafés of downtown Maitland’s Independence Lane and City Centre. Enjoy nearby Fennell Park, scenic Lake Lily Park, fitness and recreation at Genesis Orlando Sportsplex, and movies and dining at Enzian Theater and Eden Bar. AdventHealth Altamonte Springs also provides nearby access to hospital care. Sent from my iPhone

2141 Falkner Road, Maitland
2050 Thunderbird Trail, Maitland
$749,000
4 Beds ⋅ 3 Baths ⋅ Highland Park Estates SubDv. ⋅ 32751 Zip Code
Timeless Florida Charm in the Heart of Dommerich this classic ranch is ideally situated in Maitland's highly sought-after neighborhood. Combining the character of an established home with thoughtful updates and room to make it your own, this property offers an exceptional opportunity in a location that continues to be in high demand. The renovated kitchen provides a fresh, inviting space for everyday living, while improvements including a roof (2018), windows (2019), A/C (2020), and water heater (2020) add to the home's appeal. A spacious addition with vaulted ceilings and a fourth bedroom featuring a private ensuite bath creates a desirable split-bedroom floor plan, offering flexibility and privacy for family and guests. Situated on a generous 9,600-square-foot lot, the property offers plenty of room to bring your vision to life. Whether that includes a resort-style pool and cabana, an expanded primary suite, or a beautifully designed outdoor entertaining area, there is exciting potential to create a home tailored to your lifestyle. Zoned for Dommerich Elementary, Maitland Middle, and Winter Park High School, this home is ideally positioned to enjoy the lifestyle that makes Maitland so desirable. Spend your Sunday mornings exploring the Maitland Farmers' Market and enjoy the charm, local shops, dining, and sense of community that define this established neighborhood. With its timeless Florida appeal, generous lot, and possibilities for the future, this is a wonderful opportunity to put down roots in Dommerich and make it your own.

2050 Thunderbird Trail, Maitland
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