Maitland Homes for Sale

Maitland Homes for Sale

Welcome to Maitland, a charming city located in the heart of Florida. Known for its picturesque neighborhoods, lush green spaces, and friendly community, Maitland offers the perfect blend of suburban tranquility and urban convenience.

If you are looking for homes for sale in Maitland, you are in for a treat. The real estate market in Maitland is thriving, with a diverse range of properties to suit every taste and budget. From cozy bungalows to spacious family homes, Maitland has something for everyone. Whether you are a first-time homebuyer, a growing family, or a retiree looking for a peaceful retreat, Maitland has the perfect home for you.

Living in Maitland means enjoying a high quality of life, with top-rated schools, excellent healthcare facilities, and a wide range of recreational activities right at your doorstep. Explore the beautiful parks and nature trails, discover the vibrant arts and culture scene, or simply relax and unwind in this idyllic setting.

With its convenient location in the Sunshine State, Maitland offers easy access to all that Florida has to offer. From world-class beaches to exciting theme parks, the best of Florida is just a short drive away.

Come and discover the magic of Maitland. Find your dream home in this welcoming city and start living the Florida lifestyle you've always dreamed of.

Newest Maitland Homes for Sale

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
$925,000
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 large 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
2141 Falkner Road, Maitland
$515,000
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
$795,000
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
623 Green Meadow Avenue, Maitland
$525,000
3 Beds ⋅ 2 Baths ⋅ Forest Brook SubDv. ⋅ 32751 Zip Code
Welcome Home! Check out this beautiful 3 bedroom 2 bathroom single family home with a beautiful pool in a NO HOA neighborhood! Take full advantage of the morning sunrise directly in your backyard facing due east. This home features a gorgeous backyard with a beautiful pergola and screened in porch overlooking your spacious backyard oasis private pool. This property backs up to a conservation lot so no rear neighbors! As soon as you walk up you'll notice the archway that is covered in beautiful flowers when in season! As soon as you walk into the foyer you'll notice the massive open living area with a great Kitchen, Living Room & Dining room combo! The kitchen is sure to bring out your inner chef! Featuring plenty of lighting, a massive kitchen island and ample countertop & cabinet space! This home is perfect for entertaining, with the French doors out to your beautiful screened in patio and backyard steps away! The master bedroom features updated flooring, a spacious walk in closet and private master bathroom. This home is an amazing canvas for you to come in and make it your own! Reach out to the listing agent today to schedule your showing! Roof, HVAC & Water Heater 2021.

623 Green Meadow Avenue, Maitland
1010 Winderley Place Unit 100, Maitland
$349,000
2 Beds ⋅ 3 Baths ⋅ Villas Lake Destiny SubDv. ⋅ 32751 Zip Code
Discover the best of Maitland living in this light and bright end-unit townhome in the gated, lakefront community of Lake Destiny. Offering 2 bedrooms, 2.5 bathrooms, and 1,640 square feet, this inviting home features vaulted ceilings, a versatile loft perfect for a home office, media room, or additional living space, and plenty of valuable upgrades. The updated kitchen showcases crisp white cabinetry and contemporary quartz countertops as well as a dining area for special gatherings. Low-maintenance ceramic tile and laminate flooring flow throughout the first floor, drawing you into the two-story living room. This space is enhanced with transom windows, adding even more natural light creating an airy feel. Upstairs, the loft and two spacious bedrooms offer comfortable retreats, with brand-new carpet adding a fresh touch. The primary features a walk-in closet and plenty of storage in the ensuite bathroom. You also have a beautiful water view further adding to the tranquilty of the space. For added convenience, there’s an interior laundry room and a one-car garage. Step outside and take in the serene water feature view from your private patio or walk over to the community pool for a relaxing afternoon soaking up the sunshine. When you’re heading off to work or play, I-4 and 414 are just minutes away and one of Orlando’s most popular fitness facilities, Genesis Health Club, is just 1.5 miles away. Costco, Target, Home Depot, along with a variety of shopping and dining options are a short 10 minute drive and Winter Park and downtown Orlando are less than 20 minutes from the home as well. Recent improvements include new upstairs carpeting, a Kinetico whole-home water softener and filtration system with reverse osmosis filtration at the kitchen sink, a roof replaced in 2023, a 2020 water heater, and an AC system updated in 2018/2019. **The home is available to be sold unfurnished or fully furnished for a complete turnkey experience!**

1010 Winderley Place Unit 100, Maitland
1310 Winston Road, Maitland
$635,000
4 Beds ⋅ 3 Baths ⋅ English Estates Unit 2 SubDv. ⋅ 32751 Zip Code
Welcome to this exceptional four-bedroom, two-and-a-half-bathroom pool home in the heart of Maitland, offering an ideal blend of comfort, privacy, and Florida-style living. Situated in an established neighborhood near Kewannee Park, this beautifully maintained residence welcomes you with a long driveway, side-entry two-car garage, manicured landscaping, and a charming paver walkway leading to an elegant double-door entry. Step inside to a light, bright, and spacious open-concept floor plan featuring tile flooring throughout the main living areas. The well-appointed kitchen is designed for both everyday living and entertaining, showcasing granite countertops, rich cherry wood cabinetry, stainless-steel appliances, a center island with cooktop, and a stylish vent hood. The adjacent dining area provides an inviting space for gatherings, while the expansive living room features an impressive 72-inch ceiling fan and abundant natural light. A comfortable family room creates the perfect gathering space and features a wood-burning fireplace, adding warmth and character to the home. French doors open to your private outdoor oasis—an impressive screened-in lanai featuring a sparkling swimming pool, spacious sundeck, relaxing spa, and attractive water feature. Whether you’re enjoying your morning coffee, soaking up the Florida sunshine, or entertaining family and friends, this exceptional outdoor living space is designed to be enjoyed year-round. Beyond the pool area, the property offers a peaceful conservation view with no rear neighbors, creating an enhanced sense of privacy and a serene natural backdrop rarely found in such a convenient location. The spacious primary suite provides a private retreat with a generous walk-in closet and an ensuite bathroom featuring dual vanities, granite countertops, and a beautifully tiled walk-in shower. Three additional generously sized bedrooms offer flexibility for family, guests, a home office, or a hobby room. A secondary bathroom features a granite vanity and convenient shower/tub combination. Additional highlights include a roof replaced in 2019, ceiling fans throughout, spacious living areas, a side-load two-car garage, and a desirable established-community setting. Location is another standout feature. Enjoy easy access to SR 17-92, SR 436, and I-4, providing convenient connectivity throughout Central Florida. You’re just a short drive from Orlando, Winter Park, Casselberry, and Altamonte Springs, as well as shopping, dining, fitness centers, banks, supermarkets, Lowe’s, Home Depot, parks, and everyday conveniences. With its private pool, screened lanai, conservation setting, no rear neighbors, spacious open floor plan, updated kitchen features, primary suite, and highly convenient Maitland location, this home offers the perfect opportunity to enjoy the best of the Central Florida lifestyle.

1310 Winston Road, Maitland
1519 Glastonberry Road, Maitland
$525,000
4 Beds ⋅ 2 Baths ⋅ Northgate SubDv. ⋅ 32751 Zip Code
Virtually Staged. This mid-century ranch block home is ideally located in the heart of Maitland and features extensive improvements for a truly move-in-ready opportunity. The 2026 remodeled kitchen takes center stage with wood cabinetry, quartz countertops, and stainless steel appliances, complemented by beautifully updated bathrooms, tile plank flooring throughout the main living areas, recessed lighting, and a cozy wood-burning brick fireplace. Major improvements include a 2022 AC, 2019 roof by Rhyne Restoration, 2019 blown-in insulation by All Florida Insulation, 2017 AC ductwork, 2016 water heater, and 2015 electrical panel and PVC plumbing. The kitchen drop-down was removed to create a more open, modern feel. Outside, enjoy a fully fenced backyard with St. Augustine sod and an irrigation system added in 2020. Conveniently located in Maitland with easy access to shopping, dining, major roadways, and the greater Orlando area. With an extensive list of completed upgrades, this home offers the opportunity to enjoy a thoughtfully updated property without the hassle of major projects. Schedule your showing today!

1519 Glastonberry Road, Maitland
200 Seneca Trail, Maitland
$550,000
3 Beds ⋅ 2 Baths ⋅ Dommerich Estates 1st Add SubDv. ⋅ 32751 Zip Code
Located in sought-after Dommerich Estates, this single-story, 3-bedroom, 2-bathroom, block home offers 1,605 square feet of living space and an attached 2-car garage. A walkway leads to a covered front porch, where the character of the original construction is immediately apparent in the columns and detailed millwork surrounding the front door and sidelights. Inside, the main living spaces flow easily from one to another and include dining and living areas and a Florida room overlooking the backyard, with wood flooring, crown molding and a wood-burning fireplace adding warmth and character. Floor-to-ceiling windows fill the Florida room with natural light and open to a concrete patio for easy indoor-outdoor living. To the left of the entry, the kitchen and adjoining eat-in nook retain much of the home’s charm, with white wood cabinetry, a neutral tile backsplash, a window above the stainless double-bowl sink overlooking the backyard, stainless dishwasher, glass cooktop and built-in wall oven. Conveniently located just inside the garage entry, the kitchen makes unloading groceries easy, while the adjoining eat-in nook features decorative millwork, a large window and the continuation of the wood flooring. All three bedrooms are comfortably sized and feature custom interior shutters. The primary bedroom is positioned at the rear of the home with an en-suite bath featuring a glass-enclosed tiled shower and pedestal sink, while the two alternate bedrooms share a hall bath with a tiled tub/shower combination, newer vanity, undermount sink, granite countertop and linen closet. The .20-acre, 79’ by 111” lot offers room to enjoy the outdoors. Important improvements have already been completed, including a new architectural shingle roof in 2025, PEX repipe in 2011, interior electrical panel replacement and a 2017 HVAC system. Residents also have the option to join the Dommerich Beach Civic Association, with annual membership options currently beginning at $100. Membership provides access to the association’s private lake lot on the east shore of Lake Minnehaha, including a picnic area and canoe and kayak storage, with a separate membership option offering boat-ramp access. The location is compelling, with Dommerich Elementary and Maitland Middle within walking distance and zoning for Winter Park High. Minnehaha Park, also within walking distance, offers tennis courts, a playground and green space. Downtown Maitland, Lake Lily and its Sunday Farmers Market, the Art & History Museums of Maitland, restaurants, grocery stores and everyday shopping are all nearby, while Enzian Theater and additional recreation and conveniences are just a short drive away. With single-story block construction, an attached two-car garage, meaningful system improvements already completed and a location that puts schools, parks and the best of Maitland close at hand, this is a wonderful opportunity to put down roots in Dommerich Estates.

200 Seneca Trail, Maitland
1060 Gregory Drive, Maitland
$529,000
3 Beds ⋅ 2 Baths ⋅ Druid Hills Estates 1st Add SubDv. ⋅ 32751 Zip Code
Some homes have a character that simply cannot be recreated—and 1060 Gregory Drive is one of them. Built in 1962 and tucked beneath mature oaks draped in Spanish moss, this three-bedroom, two-bath Maitland home celebrates its original charm while offering the updates today’s buyers appreciate. Warm hardwood floors flow through the home, while a dramatic brick feature wall separates the living and family rooms, with a fireplace facing each space. It is a memorable architectural detail that makes both rooms feel welcoming and distinct. The updated kitchen pairs shaker-style cabinetry with granite countertops and stainless steel appliances, while plantation shutters and ceiling fans add comfort and classic style throughout. The primary bedroom features dual closets. The guest bathroom also benefits from a new vanity. Step outside to an expansive backyard deck with plenty of room for dining, entertaining and lingering beneath the trees on beautiful Florida evenings. Major improvements include an ELECTRICAL UPDATE 2026, ALL NEW DUCTWORK 2026, HVAC and REROOF 2020, WATER HEATER 2022, a NEW FENCE installed in 2023 and REPIPED 2009. Set in an established Maitland neighborhood with quick access to Winter Park, Maitland and Interstate 4, this is a home with a story, a setting and a style all its own. Come experience the character, comfort and tree-lined charm that make 1060 Gregory Drive feel like home from the moment you arrive.

1060 Gregory Drive, Maitland
120 Minnehaha Road, Maitland
$1,299,000
3 Beds ⋅ 3 Baths ⋅ Packwood Sub SubDv. ⋅ 32751 Zip Code
Virtually Staged. CAR ENTHUSIAST’S DREAM! Welcome to 120 Minnehaha Road, a truly unique Maitland property offering beautiful interior finishes, exceptional energy efficiency, incredible versatility, and plenty of room to spread out on nearly half an acre. Even better, you’re just one block from shopping, offering incredible convenience while still enjoying the space and flexibility of this impressive property. Step inside to a bright and inviting interior filled with thoughtful architectural details. The gorgeous kitchen serves as the heart of the home, featuring generous cabinetry and counter space with an open layout perfect for everyday living and entertaining. Beautiful coffered ceilings add character and dimension to the living spaces and give the home an elevated, custom feel. The spacious primary suite is a retreat of its own, featuring an impressively large walk-in closet and a stunning primary bathroom designed with both style and function in mind. Generously sized secondary bedrooms and flexible living areas provide plenty of room for family, guests, or working from home. The home was also designed with energy efficiency in mind, helping create a comfortable and efficient living environment. The property features an approximately 10-year-old metal roof, along with a lightning avoidance/protection system. Another major benefit for car enthusiasts and EV owners is the 400-amp electrical service, which, per the seller, provides capacity to support multiple EV chargers or other similar high-demand electrical uses. And then there’s the detached workshop/guest house—a standout feature with incredible possibilities. Per the seller, the City of Maitland has designated the outbuilding as a “Guest House” for zoning purposes, adding even more potential for its future use. The sellers have also brought a sewer line to the building in preparation for future plumbing. Imagine the possibilities for a future in-law apartment, guest house, detached home office, studio, or multigenerational living space, or continue using it as an incredible workshop for your cars, projects, and hobbies. The existing guest-house designation may be advantageous for a future kitchen/bath addition or ADU-style use; buyers should independently verify permitted uses, zoning, and requirements with the City of Maitland. Enjoy a fantastic Maitland location just one block from shopping and convenient to Winter Park, Downtown Orlando, dining, entertainment, and major roadways. With its gorgeous interior, energy-efficient design, 400-amp electrical service, spacious primary suite, nearly half-acre setting, impressive detached workshop/guest house, and incredible future possibilities, 120 Minnehaha Road is anything but ordinary. Schedule your private showing and come experience everything this special property has to offer!

120 Minnehaha Road, Maitland
514 Wigman Drive, Maitland
$335,900
3 Beds ⋅ 2 Baths ⋅ Eaton Estates SubDv. ⋅ 32751 Zip Code
This beautifully renovated three-bedroom, two-bathroom home offers a bright, comfortable layout with stylish modern finishes throughout. Enjoy a spacious enclosed Florida room, a large fenced backyard perfect for entertaining, pets or outdoor activities, and a covered two-car carport with additional driveway parking. Major improvements include an updated exterior A/C unit, new refrigerator, stove, dishwasher and microwave. Conveniently located in Eatonville with no HOA, this move-in-ready home is an excellent opportunity for homeowners and comes fully furnished. Near Wholefoods, LA Fitness, with many restaurants and shopping blocks away.

514 Wigman Drive, Maitland
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