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

$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
$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
$875,000
5 Beds ⋅ 4 Baths ⋅ Dommerich/Maitland Highlands SubDv. ⋅ 32751 Zip Code
Located on quiet cul-de-sac, this one-story 5 bedroom/4 bath, 3,136 sq ft ranch-style home is a short walk to A-rated Dommerich Elementary and Maitland Middle schools. This home sits on .29 of an acre that backs up to the preserved conservation. Functional floor plan with separate formal living and dining rooms, perfect for entertaining. Eat-in kitchen opens to the cozy family room anchored by the wood-burning fireplace. Expanded in 2008, the attached 900 sq ft in-law suite has a bedroom, living room, kitchenette and bath - ideal for an elderly parent or returning college grad. This flex space would also be ideal as an exercise room or home office. Primary bedroom has screened patio access and a walk-in closet. Three secondary bedrooms with access to two additional baths. Living areas have wood and tile flooring and the bedrooms have luxury vinyl plank. Out back is a sparkling screened pool overlooking the wooded back yard. Recent improvements include all new interior paint throughout (7/26) and roof ('22). Conveniently located near I-4, several parks, and excellent neighborhood restaurants. Charming library with books to share. No HOA. Welcome home!

2051 Dyan Way, Maitland
$549,000
4 Beds ⋅ 2 Baths ⋅ Forest Brook Sec 2-A SubDv. ⋅ 32751 Zip Code
Virtually Staged. Welcome home to this spacious 4-bedroom, 2-bath pool home in Maitland. From the moment you arrive, you'll appreciate the attractive brick exterior and inviting curb appeal. Inside, a welcoming foyer is flanked by a large formal living room with parquet flooring and abundant natural light, while the formal dining room features classic wainscoting and connects directly to the updated kitchen. The kitchen offers granite countertops, wood cabinetry, stainless steel appliances, a breakfast bar, and overlooks the generous family room with French doors leading to the backyard. The split-bedroom floor plan provides plenty of privacy. Two spacious secondary bedrooms with engineered hardwood flooring are located on one side of the home and share a hall bath. The primary suite is tucked away on the opposite side and features engineered hardwood floors, a walk-in closet and an ensuite bath with a walk-in shower. A fourth bedroom is centrally located, making it an ideal guest room, nursery, or home office. Just off the kitchen, you'll also find a large laundry room with built-in cabinetry for extra storage and access to the oversized two-car garage, which offers additional storage space. Step outside to a fully fenced backyard with an updated vinyl fence, a large pool ready for your personal finishing touches, and plenty of yard space for entertaining, pets, or play. Whether you choose to resurface the pool right away or customize it over time, this backyard offers great potential to create your own private outdoor retreat. Conveniently located just off Howell Branch Road, you're only minutes from I-4, Downtown Maitland, Winter Park, shopping, dining, and everyday conveniences. Call today to schedule your private showing!

564 Brookside Circle, Maitland
$399,000
3 Beds ⋅ 2 Baths ⋅ English Estates Unit 2 SubDv. ⋅ 32751 Zip Code
Offered for the first time in 42 years, this 3-bedroom, 2-bath home is located in the highly desirable English Estates community in Seminole County. With spacious living areas, quality construction, and timeless character, this home offers a wonderful opportunity to make it your own. A circular driveway provides ample parking with plenty of room for multiple vehicles, including an RV or boat. Inside, the home features a formal living room with a wood-burning fireplace and traditional mantle. The kitchen includes a cozy eat-in dining area centered around a second wood-burning brick fireplace, while the adjacent family room is filled with natural light from a wall of windows overlooking the backyard. All three bedrooms are generously sized, including an oversized primary suite with a walk-in closet. Recent updates include a new roof (2020) and a whole-house generator (2018). Additional features include a well solely for the sprinkler system, a walk-in attic, attic fan, backyard fruit trees, and flood lights. English Estates is one of Maitland's most established neighborhoods, offering Seminole County schools and convenient access to shopping, dining, parks, major roadways, and Downtown Orlando. From this location you are less than 10 minutes to the I-4 Express lanes to get to downtown in 20 minutes total, you are 15 minutes to the hustle and bustle of Winter Park Village and all surrounding shops and restaurants. This is a rare opportunity to own a home that has been lovingly cared for and is ready for its next owner.

2340 Derbyshire Road, Maitland
$699,000
3 Beds ⋅ 2 Baths ⋅ Dommerich Estates 1st Add Maitland SubDv. ⋅ 32751 Zip Code
**BOATING/LAKE ACCESS** Welcome to 553 Arapaho Trail, where timeless MID-CENTURY CHARM meets thoughtful modern living in the highly sought-after DOMMERICH ESTATES community of Maitland. Offering OVER 1,500 SQUARE FEET of beautifully maintained living space, this 3-BEDROOM, 2-BATHROOM HOME features a desirable SPLIT FLOOR PLAN designed for both privacy and everyday comfort. From the moment you arrive, you'll appreciate the exceptional curb appeal with LUSH, MATURE LANDSCAPING, a NEWLY PAINTED EXTERIOR, and an EXTRA-WIDE, EXTRA-LONG BRICK PAVER DRIVEWAY with room for up to SIX VEHICLES. Inside, the home's original character has been carefully preserved while incorporating today's most important updates, including a NEW ROOF (2025), NEW GUTTERS, WHOLE-HOUSE REPIPE, ELECTRICAL UPGRADES, HARDWOOD FLOORING THROUGHOUT, NEW KITCHEN APPLIANCES, an UPGRADED PRIMARY EN-SUITE, stylish UPDATED LIGHTING FIXTURES, an EXTENDED ATTIC WITH ABUNDANT STORAGE, and a PAINTED GARAGE FLOOR. One of the neighborhood's rare homes with BURIED ELECTRICAL SERVICE, the property also offers a cleaner streetscape and added peace of mind. Step outside and discover your own private backyard retreat featuring an INCREDIBLE SCREENED-IN POOL, an expansive BRICK PAVER POOL DECK, and a charming BRICK PAVER GARDEN WALKWAY winding through beautifully landscaped grounds—perfect for entertaining or relaxing year-round. Beyond the home, DOMMERICH ESTATES continues to impress with its welcoming sense of community and location within one of Central Florida's most desirable school districts, originally designed around A-RATED SCHOOLS to make walking and biking to class safe and convenient. Residents also enjoy access to a VOLUNTARY, LOW-COST HOA that includes a PRIVATE BOAT RAMP to the WINTER PARK CHAIN OF LAKES, opening the door to BOATING, PADDLEBOARDING, FISHING, and unforgettable days on the water. The CITY OF MAITLAND offers the perfect balance of convenience and charm with its WALKABLE NEIGHBORHOODS, beautiful parks, local festivals, downtown concerts, and community events, while world-renowned PARK AVENUE in Winter Park is just minutes away for AWARD-WINNING DINING, BOUTIQUE SHOPPING, ART GALLERIES, and weekend brunch. This is more than just a home—it's an opportunity to experience one of CENTRAL FLORIDA'S MOST BELOVED NEIGHBORHOODS and lifestyles.

553 Arapaho Trail, Maitland
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