Maitland Real Estate

Maitland Real Estate

Welcome to Maitland, Florida – a hidden gem nestled in the heart of Central Florida, just a stone’s throw from the bustling city of Orlando. Known for its charming neighborhoods, lush landscapes, and vibrant community spirit, Maitland offers a unique blend of suburban tranquility and urban convenience.

Maitland is steeped in history, with roots dating back to the 19th century. The city boasts a rich cultural heritage, showcased in its historic architecture and numerous museums, including the Maitland Art Center, which is renowned for its stunning Mayan-inspired motifs. Nature lovers will find solace in the city’s picturesque parks and lakes, such as Lake Lily Park, where you can enjoy serene walks, picnics, and seasonal festivals.

The city’s prime location provides easy access to major highways, making commuting to nearby cities a breeze. Residents appreciate the excellent school systems and family-friendly atmosphere, making it an ideal place to raise children. With a diverse array of dining options, boutique shops, and local markets, Maitland’s vibrant downtown area is perfect for those seeking a lively community atmosphere.

Whether you’re exploring the scenic bike trails, indulging in local cuisine, or attending one of the many community events, Maitland is a city that embraces both tradition and modernity. With its charming neighborhoods, friendly faces, and a wealth of amenities, Maitland truly embodies the essence of Florida living. Come discover your new home in this enchanting city, where every day feels like a vacation!

Newest Listings in Maitland

$325,000
3 Beds ⋅ 3 Baths ⋅ Lake Faith Villas Condo SubDv. ⋅ 32751 Zip Code
Welcome to Lake Faith Villas, an established lakefront community in Maitland. This spacious 3-bedroom, 3-bathroom condominium offers 1,860 square feet with an open floor plan, abundant natural light, and views of the community's landscaped grounds. The layout includes a first-floor bedroom and full bathroom, offering flexibility for guests, a home office, or everyday living. Upstairs, the primary suite features a walk-in closet and en-suite bath, while the third bedroom also has its own full bathroom. Recent updates include a new Washer and Dryer (2025), HVAC System (2024), and Hot Water Heater (2022). Enjoy your garden patio or take advantage of the community's lakefront clubhouse, swimming pool, and direct views of Lake Faith. Located just minutes from Winter Park, SunRail, and major highways, the home is also close to Maitland's growing selection of restaurants, shopping, and fitness options, including the newly opened Crunch Fitness. Schedule your private showing today!

283 W Lake Faith Drive Unit 146, Maitland
$259,000
2 Beds ⋅ 3 Baths ⋅ Park Lake Grove Condo Ph C SubDv. ⋅ 32751 Zip Code
Welcome home to this beautifully updated two-story condo nestled in one of Maitland's most established communities, where lush mature landscaping, winding sidewalks, a community pool, lake access and a private dock create a peaceful setting just minutes from some of Central Florida's favorite restaurants, shopping and entertainment. Enjoy easy access to Enzian Theater, Winter Park Village, Trader Joe's, Whole Foods, Park Avenue and countless local dining favorites all within minutes. Inside, you'll immediately notice one of this home's most unique features. The floor plan was thoughtfully reimagined to create an expansive open-concept living space centered around a beautifully enlarged kitchen—offering a layout rarely available within the community. Warm cabinetry, stainless steel appliances, a center island, under cabinet lighting, recessed lighting and abundant workspace make this kitchen equally suited for everyday living and entertaining. Ceramic tile flooring flows throughout the entire first floor, while upstairs features durable laminate wood flooring throughout both bedrooms. Each bedroom serves as its own private primary suite with an ensuite bathroom, providing exceptional flexibility for guests, roommates or multi-generational living. One suite features a tub/shower combination while the other offers a walk-in shower. A third full bathroom downstairs with a walk-in shower adds additional convenience for visitors. Additional highlights include updated energy-efficient double-pane windows and sliding glass door, a dedicated interior laundry room complete with cabinetry and folding counter, attractive 5¼-inch baseboards throughout the main living area, and a private rear courtyard that connects to the garage—perfect for grilling, outdoor dining, container-gardening or additional storage. Combining an exceptional location, a one-of-a-kind floor plan, and low-maintenance living in the heart of Maitland and minutes from Winter Park, this home offers a rare opportunity to enjoy both convenience and comfort in one of Central Florida's most desirable areas.

1713 Gulfview Drive Unit 435B, Maitland
$745,000
4 Beds ⋅ 3 Baths ⋅ Dommerich Estates 1st Add SubDv. ⋅ 32751 Zip Code
This charming 4-bedroom, 3-bath home is in sought-after Dommerich Estates, one of the area’s most desirable neighborhoods. Designed for comfort, style, and everyday living, the home features a unique open floor plan with vaulted ceilings, a warm wood-burning fireplace, and an updated kitchen with solid wood cabinetry and granite countertops. Fresh interior and exterior paint, an oversized garage with built-in shelves, an extended paver driveway, and paver walkways add to the home’s curb appeal and move-in-ready feel. Step outside to a peaceful, private covered screened porch—your own outdoor retreat for relaxing mornings, quiet evenings, or future entertaining with plumbing and electrical already in place for a summer kitchen. Major updates include a 2025 roof, 2017 AC, and 2014 water heater. Dommerich Estates is known for its welcoming community feel and was thoughtfully designed around A-rated schools, making walking and biking to school safe and convenient. Ideally located just 1 ½ blocks from the elementary and middle school and 1 ½ blocks from the neighborhood lake lot, this home offers easy access to sunsets, fishing, and launching a watercraft for a day on the lake. Enjoy the best of Maitland living—close to Orlando yet rich with small-town charm, walkable neighborhoods, parks, downtown parties, concerts, and community events. With its prime location, thoughtful updates, inviting indoor and outdoor spaces, and access to highly desirable neighborhood amenities, this Dommerich Estates home delivers the lifestyle buyers are looking for.

550 Arapaho Trail, Maitland
$475,000
3 Beds ⋅ 2 Baths ⋅ Greenwood Gardens Sec 01 SubDv. ⋅ 32751 Zip Code
Virtually Staged. Step into sophisticated modern living at 761 Robinhood Drive, a beautifully renovated three-bedroom, two-bathroom Maitland residence with no HOA. Designed for effortless everyday living and entertaining, this home welcomes you with an impressive open-concept floor plan, abundant natural light, dramatic 14-foot vaulted ceilings, contemporary fixtures, and luxury vinyl plank flooring throughout the main living areas. Expansive sliding glass doors create a seamless connection to the enclosed, screened-in concrete patio—an inviting retreat for relaxing, dining, or enjoying Florida’s beautiful weather. Beyond the patio, a spacious, fully fenced backyard provides endless possibilities for entertaining, gardening, or creating your own private outdoor oasis. At the heart of the home is a chef-inspired kitchen that balances bold style with thoughtful functionality. It features elegant waterfall-edge quartz countertops, a striking black tile backsplash, new stainless steel appliances, soft-close cabinetry, matte-black hardware, a pantry, a charming breakfast nook, and a smart digital faucet with temperature display. Every detail has been selected to create a modern and refined gathering space. The spacious primary suite offers private sliding-door access to the patio and a stylish barn-door entrance to the ensuite bathroom. Inside, you’ll find designer tile flooring, an oversized glass-enclosed walk-in shower, a vanity with quartz countertops, modern fixtures, and a generous walk-in closet. Both additional bedrooms have been refreshed and feature built-in closets. The equally impressive guest bathroom includes elegant tilework, a tub with glass shower enclosure, quartz countertops, and a contemporary vanity. This move-in-ready home has been extensively updated with a brand-new water heater, updated plumbing and electrical systems, a 2023 air-conditioning system, a 2018 roof, new LG washer and dryer, and new stainless steel appliances. Surrounded by Maitland’s scenic lakes and ideally positioned near the Maitland SunRail Station, Lake Lily Park, shopping, dining, and cultural attractions, this home offers exceptional Central Florida convenience. Located near Lake Sybelia Elementary School and with easy access to North Orlando Avenue, Maitland Boulevard, and Interstate 4, downtown Orlando, Winter Park, and surrounding destinations are only minutes away. Modern design, extensive upgrades, a prime Maitland location, and no HOA—761 Robinhood Drive is the opportunity you’ve been waiting for.

761 Robinhood Drive, Maitland
$324,900
2 Beds ⋅ 1 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code
Welcome to this beautifully 2 BR remodeled FIRST FLOOR CORNER condominium unit with PRIVATE SCREENED IN PORCH, perfectly situated in the heart of the highly desirable LAKE MAITLAND TERRACE located in the Maitland/Winter Park area. This move-in-ready home has been completely renovated with stylish, modern finishes throughout. The brand-new kitchen features all-new cabinetry, countertops, and appliances, creating the perfect space for cooking and entertaining. The updated bathroom has been tastefully redesigned, while additional upgrades include new lighting, interior doors, a new air conditioning system, and a new hot water heater, providing comfort and peace of mind for years to come. A full-size washer and dryer are conveniently located inside the unit. Enjoy your own private screened enclosure—an ideal spot to relax with your morning coffee or unwind in the evening. As a desirable corner unit on the first floor, this home offers added privacy and easy accessibility including convenient parking. The community offers exceptional amenities, including lake access with a private dock for fishing and enjoying the waterfront, as well as a community pool and clubhouse. Located just minutes from the charming shops, restaurants, parks, and entertainment of downtown Maitland and Winter Park, this home combines modern updates with an unbeatable location. Whether you're searching for a primary residence or seasonal retreat, this beautifully updated condominium is ready to impress.

1140 S Orlando Avenue Unit E1, Maitland
$360,000
2 Beds ⋅ 1 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code
Experience the perfect blend of Mid-Century Modern charm and contemporary living in this beautifully renovated 2-bedroom, 1-bath condominium in the highly sought-after Lake Maitland Terrace community. Nestled on the shores of Lake Maitland with access to the renowned Winter Park Chain of Lakes, this waterfront community offers an exceptional lifestyle in one of Central Florida's most desirable locations. Inside, you'll find a thoughtfully redesigned interior featuring a stunning chef-inspired kitchen with classic shaker cabinetry, quartz countertops, a spacious pantry, and a large center island offering storage on both sides. The open-concept layout creates a bright and inviting living space that's perfect for entertaining or relaxing at home. The generous primary bedroom features a large closet, while the beautifully updated bathroom boasts a spacious walk-in shower and modern finishes. Additional conveniences include an in-unit washer and dryer, a private storage room located behind the unit, and access to the community's updated laundry facilities. Lake Maitland Terrace offers outstanding amenities, including a new lakefront swimming pool, community dock, clubhouse, putting green, and direct access to Lake Maitland and the Winter Park Chain of Lakes. Ideally located just moments from Lake Lily, the Enzian Theater, and the vibrant Independence Lane District, you'll enjoy easy access to local restaurants, breweries, shopping, and the popular farmer’s market. Winter Park Village, Park Avenue, and major roadways are also just minutes away. Located within the highly desirable Dommerich Elementary, Maitland Middle, and Winter Park High School districts, this move-in-ready home offers an unbeatable combination of style, location, and convenience. Don't miss this incredible opportunity. Schedule your private showing today!

1140 S Orlando Avenue Unit B-7, Maitland
$395,000
3 Beds ⋅ 2 Baths ⋅ Winfield SubDv. ⋅ 32751 Zip Code
Welcome to the Winfield community in Maitland, where this 3-bedroom, 2-bathroom home with a 2-car garage offers both comfort and function. The foyer opens into a flexible dining area and flows into the kitchen, which features granite countertops, wood cabinetry, and newer appliances. The spacious living room with vaulted ceilings creates an open and inviting central gathering space. The split-bedroom floor plan provides privacy, with the primary suite located on one side of the home. The primary bedroom includes a walk-in closet and an en-suite bath. Two additional bedrooms and a full bath are located on the opposite side of the home, along with a convenient interior laundry room. French doors lead from the living room to a large screened-in pavered porch overlooking the fully fenced backyard. This versatile outdoor space is ideal for dining, relaxing, or hosting get-togethers in a low-maintenance setting. Reach out to schedule your tour today.

2115 Korat Lane, Maitland
$535,000
4 Beds ⋅ 2 Baths ⋅ Roosevelt Place SubDv. ⋅ 32751 Zip Code
Move-in ready and full of charm, this one-story Maitland home offers 4 bedrooms, 2 bathrooms, and an array of desirable features. Enjoy Florida living with your own in-ground pool, or relax by the cozy wood-burning fireplace in the front living room. The updated kitchen (2019) features granite countertops and modern finishes, while the primary bathroom includes a beautifully tiled walk-in shower. Additional highlights include a spacious Florida room, a two-door, two-car garage, fresh interior paint, and a roof replaced in 2014. Conveniently located just minutes from Altamonte Springs, Winter Park, shopping, dining, and I-4, this home offers both comfort and an ideal location.

112 Roosevelt Place, Maitland
$795,550
3 Beds ⋅ 3 Baths ⋅ Maitland Woods Third Add SubDv. ⋅ 32751 Zip Code
Nestled beneath a canopy of majestic oak trees in the highly sought after Maitland Woods neighborhood, this beautifully updated 3 bedroom, 2.5 bathroom pool home sits on an expansive .45 acre homesite, offering timeless charm, thoughtful updates, and the lifestyle you've been searching for. From the moment you arrive, you'll appreciate the instant curb appeal of this classic brick ranch home, framed by mature landscaping and one of Maitland Woods' picturesque tree lined streets. Inside, you're welcomed by a spacious formal living room that sets the tone for the warm and inviting spaces beyond. The beautifully renovated kitchen serves as the heart of the home, featuring stylish finishes, generous workspace, and an effortless flow into the family room, where a stunning brick fireplace creates the perfect place to gather with family and friends. The spacious primary suite offers a peaceful retreat complete with a custom walk in closet and an updated ensuite bath. Two additional bedrooms provide comfortable accommodations for family, guests, or a home office.' Designed for year round Florida living, the expansive screened lanai overlooks your own private backyard oasis featuring a saltwater pool, newer pergola, outdoor shower, and an oversized fenced backyard with plenty of room to entertain, play, or simply relax beneath the shade of mature oaks. Recent improvements include a new HVAC system (2025), complete replumbing, and updated electrical, offering peace of mind for years to come. Life in Maitland Woods is about more than just the home. Enjoy evening walks around the spring fed waters of Lake Sybelia, where neighbors gather to take in beautiful sunsets beneath the oak canopy. Just minutes away, charming downtown Maitland offers local restaurants, community events, the weekly farmers market, and beloved traditions like Movies in the Park. With Orangewood Christian School within walking distance and easy access to downtown Maitland, downtown Orlando, shopping, dining, and major roadways, this location perfectly blends small town charm with everyday convenience. This is more than a home. This is the sign you've been looking for. It's an opportunity to enjoy the timeless character, community, and lifestyle that have made Maitland Woods one of Central Florida's most cherished neighborhoods.

211 Talmeda Trail, Maitland
$345,000
4 Beds ⋅ 2 Baths ⋅ Eaton Estates SubDv. ⋅ 32751 Zip Code
Welcome to 501 Fitzgerald Drive, where modern updates meet an unbeatable location. Situated on a desirable corner lot, this beautifully renovated 4-bedroom, 2-bathroom home offers the perfect combination of style, functionality, and convenience. Inside, you'll find an open and inviting layout featuring luxury vinyl plank flooring, quartz countertops, a designer backsplash, stainless steel appliances, fresh interior finishes, and abundant natural light throughout. Major improvements—including the roof and HVAC system—provide added peace of mind, making this home truly move-in ready. Step outside to enjoy the spacious screened-in porch, the perfect place to relax, entertain, or enjoy Florida evenings without the bugs. The oversized driveway and covered carport provide plenty of parking for family and guests. Conveniently located just minutes from top-rated schools, Winter Park Village, shopping, dining, and entertainment, you'll also appreciate easy access to I-4 for commuting throughout Central Florida. Fitness enthusiasts will love being just around the corner from the new Life Time athletic country club, offering world-class fitness, pools, pickleball, and wellness amenities. Whether you're a first-time homebuyer, growing family, or simply looking for a beautifully updated home in a prime location, 501 Fitzgerald Drive is ready to welcome you home. Schedule your private showing today!

501 Fitzgerald Drive, Maitland
$969,000
4 Beds ⋅ 3 Baths ⋅ Druid Isle SubDv. ⋅ 32751 Zip Code
Welcome to your private lakefront retreat on one of Maitland's most coveted streets—Druid Isle. Tucked away on a quiet peninsula surrounded by water on every side, this exclusive one-way-in, one-way-out street offers an unmatched sense of privacy and tranquility. Situated at the end of the cul-de-sac, this beautifully updated 4-bedroom, 3-bathroom pool home combines modern finishes with an incredible waterfront lifestyle. Inside, you'll find a bright, open floor plan featuring brand-new luxury vinyl flooring throughout, fresh interior paint, and thoughtfully updated spaces designed for both everyday living and entertaining. Every detail has been carefully refreshed, making this home completely move-in ready. Step outside to your own private oasis where a sparkling pool overlooks the water, creating the perfect setting for relaxing or hosting family and friends. The exterior has been transformed with all-new professional landscaping, a brand-new paver driveway, and a newly paved walkway leading to a dedicated fire pit area—an ideal place to gather and enjoy breathtaking sunsets over the lake. Whether you're looking for peaceful waterfront living, exceptional privacy, or a home that's been completely updated from top to bottom, this Druid Isle gem offers a rare opportunity to own one of Maitland's most desirable lakefront properties. Experience the beauty, serenity, and lifestyle that only Druid Isle can provide. ROOF - 2017 HOT WATER HEATER - 2026 AC - 2012 PLUMBING - Updated 2018 ELECTRICAL - Updated 2018

1301 Druid Isle Road, Maitland
$990,000
4 Beds ⋅ 4 Baths ⋅ Sybelia Place SubDv. ⋅ 32751 Zip Code
Beautiful two-story home nestled on a quiet cul-de-sac in desirable Maitland, FL right off of Lake Sybelia. Featuring a private pool, spacious layout, luxury kitchen, high ceilings and an ideal location. Sub-Zero Pro refrigerator, Wolf duel-fuel range, quartzite counter tops, custom cabinetry, gas tankless water heater. Walking distance from Lake Sybelia, Maitland farmer's market, library and restaurants. This 4 bedroom, 3 1/2 bathroom home offers the perfect blend of comfort and privacy in this perfect neighborhood!

313 Macarthur Place, Maitland
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