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$979,000
4 Beds ⋅ 3 Baths ⋅ Wellington SubDv. ⋅ 32751 Zip Code
Welcome to 1281 Wellington Terrace, a beautifully maintained 4-bedroom, 3-bath home offering 2,931 square feet in one of Maitland’s most desirable and established neighborhoods. With spacious interiors, thoughtful updates, and deeded access to Lake of the Woods, this home offers an exceptional combination of comfort, versatility, and location. One of the home’s most distinctive features is its rare split floor plan with two private primary suites positioned on opposite sides of the home. The second primary suite also features its own separate entrance, offering exceptional flexibility for multigenerational living, extended family, guests, a private home office, or an independent retreat—all while maintaining privacy within the main residence. Inside, soaring beamed ceilings and skylights fill the home with natural light, while a beautiful statement fireplace anchors the main living area. The open kitchen flows effortlessly into the gathering spaces and is complemented by a separate butler’s pantry and spacious laundry room, providing the extra storage, functionality, and convenience that make everyday living and entertaining effortless. Recent improvements include new windows throughout and a three year old roof, adding comfort, efficiency, and peace of mind. An expansive Florida room opens the home to the private, low-maintenance backyard, creating a wonderful extension of the living space and an inviting setting for entertaining, morning coffee, or simply relaxing and enjoying Florida living year-round. Ideally located in Maitland’s sought-after Wellington community, residents enjoy deeded lake access, highly rated Seminole County schools, and convenient access to Winter Park’s Park Avenue, with its renowned restaurants, boutiques, museums, and cultural attractions. Nearly 3,000 square feet, two private primary suites, generous living spaces, beautiful architectural character, and an outstanding Maitland location—1281 Wellington Terrace offers the space, privacy, and flexibility to live beautifully at every stage of life.

1281 Wellington Terrace, Maitland
$239,000
2 Beds ⋅ 2 Baths ⋅ Park Lake Villas Condo SubDv. ⋅ 32751 Zip Code
Virtually Staged. Rare updated 2/2 | | Top-Rated Schools Welcome to peaceful Park Lake Villas! This fully updated single-story condo has spacious living, major energy-efficient upgrades, and an unbeatable location zoned for Dommerich Elementary, Maitland Middle, and Edgewater High. Key Features Brand New A/C (2025) & Updated R-38 Insulation Low-E Thermal Pane Windows & Slider Door replaced throughout Remodeled Kitchen with updated cabinets, appliances, paint, and a cozy dinette space Fully Remodeled Bathrooms (2024) including a private primary en-suite Private Outdoor Space: Second bedroom opens via slider to a fenced yard & patio Convenience: Indoor laundry room with washer/dryer included, pull-down attic storage, and designated parking right out front. Community & Location: Enjoy a tranquil, well-maintained neighborhood with a community pool just steps away. Walk or bike to Lake Lily Park & Farmers Market, Downtown Maitland, Enzian Theater, and local dining. Minutes to SunRail, I-4, Winter Park Village, and Park Ave!

1711 Grove Street Unit 519, Maitland
$585,000
4 Beds ⋅ 2 Baths ⋅ English Estates Unit 2 SubDv. ⋅ 32751 Zip Code
Virtually Staged. Welcome to 1241 Manchester Road, a beautifully renovated home nestled in the heart of English Estates, one of Maitland's most sought-after and established neighborhoods. This exceptional 4-bedroom, 2-bath residence seamlessly blends timeless charm with modern updates, offering the perfect balance of comfort, style, and functionality. From the moment you step inside, you'll appreciate the bright open-concept floor plan, thoughtfully designed to maximize natural light and create an effortless flow between the living, dining, and kitchen areas—perfect for both everyday living and entertaining. The beautifully updated kitchen serves as the heart of the home, complemented by tastefully renovated bathrooms and a versatile flex room that can easily function as a home office, fitness room, playroom, or media space. Step outside to enjoy the lanai overlooking a backyard, offering endless possibilities for weekend gatherings, outdoor entertaining, or simply relaxing in the privacy of your own backyard. Perfectly positioned in a quiet, tree-lined neighborhood, this home offers the ideal combination of tranquility and convenience. Just minutes from Winter Park, Downtown Maitland, and Downtown Orlando, you'll enjoy quick access to I-4, US-17/92, SR-436 (Semoran Boulevard), Howell Branch Road, and SR-434, making commuting throughout Central Florida effortless. Everyday conveniences are just around the corner, including Publix, Trader Joe's, Whole Foods Market, Costco, Target, Winter Park Village, Altamonte Mall, and an impressive selection of local favorites and acclaimed restaurants. Whether you're looking for your forever home or simply want to enjoy one of Central Florida's most desirable locations, 1241 Manchester Road offers an exceptional opportunity to experience the very best of Maitland living. Schedule your private showing today and discover why homes in English Estates are always in high demand.

1241 Manchester Road, 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 etair conditioning system, and a newer 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 SPACE. 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
$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
$435,000
3 Beds ⋅ 2 Baths ⋅ Winfield SubDv. ⋅ 32751 Zip Code
Welcome to this beautiful 3-bedroom, 2-bathroom home featuring a sparkling pool and exceptional curb appeal! Nestled among lush landscaping, the backyard is a true private oasis—perfect for relaxing or entertaining. Inside, you'll be greeted by vaulted ceilings, abundant natural light, upgraded flooring, high-end countertops, and a beautifully designed kitchen that's both stylish and functional. The thoughtfully designed split floor plan offers privacy, with the spacious primary suite situated in its own wing and two additional bedrooms on the opposite side of the home. Additional highlights include a charming breakfast nook, a large living room, a dedicated office area, and a convenient indoor laundry room with the washer and dryer included. The attached garage provides ample storage and parking. Currently has a tenant with a lease ending on Nov 19th. Ideally located near the thriving Maitland business district, this home is just minutes from shopping, dining, Altamonte Mall, Winter Park, and offers easy access to I-4 and SR 414, making commuting throughout Central Florida a breeze. Don't miss the opportunity to make this exceptional home your own—schedule your private showing today!

2180 Tortoise Shell Drive, Maitland
$1,075,000
4 Beds ⋅ 4 Baths ⋅ Oakleigh Third Add SubDv. ⋅ 32751 Zip Code
Come see 51 Oakleigh Ln, a functional residence arranged for everyday practicality. A comfortable living space features a fireplace. The kitchen includes an accent backsplash and all stainless steel appliances. The primary bedroom has a walk in closet, and its bathroom features double sinks and a separate tub and shower. Outside, a patio connects to an in ground pool within a fenced in backyard. This property is a must-see for comfort and outdoor living. Included 100-Day Home Warranty with buyer activation

51 Oakleigh Lane, Maitland
$850,000
2 Beds ⋅ 3 Baths ⋅ Moorings On Lake Maitland Condo Bldg 05 SubDv. ⋅ 32751 Zip Code
Every so often, a property comes along that redefines what lake living can be, and this is that home. Thoughtfully reimagined from top to bottom, this two-bedroom, two-and-a-half-bath residence blends refined design with the effortless lifestyle of the Winter Park Chain of Lakes. Go inside to discover a fully renovated interior anchored by a showstopping 14-foot Cambria quartz waterfall island, the heart of a kitchen designed for entertaining and everyday luxury. The GE Monogram and Café appliance suite, paired with custom solid wood, soft-close cabinetry, makes every detail feel bespoke. Natural light fills the living spaces through PGT double-pane insulated windows and Andersen French doors, framing tranquil garden views that create a sense of calm and privacy. Upstairs, two spacious bedroom suites offer comfort and style, each crafted with high-end finishes and thoughtful touches throughout. Beyond the walls, enjoy the rare privilege of a dedicated boat slip on Lake Maitland, Winter Park’s largest and sought-after body of water. Cruise the connected lakes, explore the historic canals or simply unwind at sunset, all just near home. Built in 1985 and completely transformed with modern systems, including a 2023 HVAC and water heater, this residence offers peace of mind to match its beauty. A one-car garage adds convenience, while every finish reflects care, quality and craftsmanship. Here, luxury isn’t just found inside, it’s a way of life, lived by the water.

219 Quayside Circle, Maitland