Maitland / Eatonville Homes with HOA

Maitland / Eatonville Homes with HOA

Welcome to the enchanting region of Maitland and Eatonville, nestled in the heart of Central Florida! Known for its rich history, vibrant culture, and stunning natural beauty, this area offers a unique blend of suburban charm and urban convenience. Just a stone's throw from downtown Orlando, Maitland is a peaceful oasis that boasts picturesque lakes, lush parks, and a welcoming community spirit.

Maitland is renowned for its beautiful homes, many of which are part of well-maintained neighborhoods with Homeowners Associations (HOA). These communities provide residents with a sense of security and a commitment to maintaining property values, ensuring that the area remains not only beautiful but also desirable. The HOA amenities often include access to sparkling swimming pools, tennis courts, and community events that foster connections among neighbors, making it an ideal place for families and individuals alike.

Eatonville, one of the oldest African American municipalities in the United States, is just a short drive away and adds a rich cultural tapestry to the region. With its historical significance and vibrant arts scene, residents can enjoy local festivals, art galleries, and delicious dining options that celebrate the area's heritage.

Whether you are looking for a cozy family home or a modern retreat, Maitland and Eatonville offer a diverse range of properties that cater to various lifestyles. Explore the charm of this delightful region and discover the perfect place to call home, where community spirit and natural beauty come together in perfect harmony.

Newest Maitland / Eatonville Homes with HOA

1233 Wellington Terrace, Maitland
$1,139,500
4 Beds ⋅ 4 Baths ⋅ O6453544 MLS
Nestled beneath a canopy of majestic oak trees in Maitland’s sought-after Wellington community, this beautifully maintained 4-bedroom, 3.5-bath residence offers 2,988 square feet of timeless architectural character, inviting living spaces, and glimpses of spring fed Lake of the Woods from both inside and outside the home. A sweeping circular driveway, manicured landscaping, and striking arched windows create an unforgettable first impression. Inside, a grand two-story foyer welcomes you with an elegant staircase and rich hardwood flooring, leading into thoughtfully designed spaces filled with natural light. The stunning living room is the architectural centerpiece of the home, featuring soaring vaulted ceilings with exposed wood detailing, a dramatic stone fireplace, custom built-ins, and an expansive arched window overlooking the beautifully landscaped grounds. A formal dining room with elegant millwork and built-in cabinetry provides a lovely setting for entertaining, while an adjoining open workspace offers flexibility for a home office or creative retreat. The spacious kitchen features white cabinetry, exotic natural stone countertops, generous preparation space, and a charming breakfast nook surrounded by windows. An additional living area opens directly to the pool and backyard, creating a natural extension of the home's gathering spaces. Currently enjoyed as a playroom, this versatile space can easily evolve with your family's changing needs, from a children's retreat to a game room, media lounge, or relaxed gathering space for years to come. Conveniently located on the main floor, the primary suite offers a peaceful retreat with abundant natural light, warm hardwood flooring, and an ensuite bathroom featuring dual vanities and a spacious walk-in shower. Three additional bedrooms upstairs provide comfortable accommodations and flexibility for family and guests. Step outside to discover a private backyard oasis featuring a sparkling pool, expansive lawn, mature landscaping, and multiple areas for outdoor dining, entertaining, or simply enjoying the Florida sunshine. A fully fenced backyard and two-car garage add everyday convenience, while the generous indoor and outdoor spaces create an inviting setting for everything from quiet afternoons to lively family gatherings. Residents of Wellington enjoy deeded access to Lake of the Woods, along with an exceptional location near highly regarded Seminole County schools, Winter Park’s charming Park Avenue, boutique shopping, and renowned restaurants. From peaceful mornings beneath the majestic oaks to beautiful sunsets over the neighborhood lake, this distinctive Maitland residence offers a wonderful balance of architectural charm, everyday comfort, and a place to grow and make memories for years to come.

1233 Wellington Terrace, Maitland
1325 Lake Shadow Circle Unit 12103, Maitland
$199,000
2 Beds ⋅ 2 Baths ⋅ O6452783 MLS ⋅ 12 BLDG.
Virtually Staged. Enjoy convenient first-floor living in the gated lakeside community of Visconti West! This two-bedroom, two-bath condominium offers an open living and dining area, high ceilings, and a split-bedroom layout. Each bedroom features an en-suite bathroom and walk-in closet, providing comfort and privacy. The kitchen includes a breakfast bar and closet pantry, while an interior laundry room accommodates the washer and dryer. A screened, covered patio offers space to relax outdoors, with an additional storage closet for everyday convenience. Community amenities include two lakeside pools, a fitness center, clubhouse, tennis and basketball courts, and a car wash area. The monthly association fee includes water, sewer, trash service, and exterior and grounds maintenance. Located near Maitland Boulevard and I-4, Visconti West offers convenient access to downtown Orlando, Winter Park, shopping, dining, and entertainment. Discover a comfortable home with first-floor convenience and an array of community amenities.

1325 Lake Shadow Circle Unit 12103, Maitland
989 Hamlet Court, Maitland
$299,999
3 Beds ⋅ 2 Baths ⋅ O6452476 MLS
An Inviting Retreat in a Prime Maitland Location!! Discover a home where comfort, charm, and convenience come together beautifully. This inviting 3-bedroom, 2-bathroom residence offers a welcoming atmosphere, thoughtfully designed spaces, and an exceptional location just 1.5 miles from Winter Park Village. Step inside to discover ceramic tile flooring throughout, creating a cohesive, timeless look while offering easy maintenance. Vaulted ceilings enhance the sense of openness, allowing the living spaces to feel bright and airy. Natural light fills the kitchen, where a charming dining area provides the perfect setting for leisurely breakfasts, morning coffee, or intimate gatherings with family and friends. Sliding glass doors extend the living space outdoors, offering easy access to the yard and creating a seamless connection between indoor comfort and outdoor enjoyment. The bedrooms are designed with everyday functionality in mind, with both the primary and secondary bedrooms featuring spacious walk-in closets for added storage. The primary suite offers a relaxing escape, complete with a private bathroom featuring a soothing garden tub and a separate walk-in shower—the perfect place to unwind and recharge. A convenient one-car garage adds another practical touch to this inviting home. A Location That Makes Every Day More Enjoyable One of this home's standout features is its desirable location. Just 1.5 miles from Winter Park Village, you'll be moments away from an exciting selection of boutiques, popular retailers, restaurants, cafés, and entertainment options. Whether you're planning a dinner out, browsing your favorite shops, or enjoying a casual afternoon close to home, this location puts the best of the surrounding area within easy reach. Combining comfortable living spaces, inviting natural light, and convenient access to local favorites, this property offers a wonderful opportunity to enjoy a lifestyle defined by both comfort and accessibility. Additional highlights include a 9-year-old roof and a low HOA fee, adding to the home's overall appeal. Comfortable living. A sought-after location. Everyday convenience.

989 Hamlet Court, Maitland
1507 Grove Street, Maitland
$230,000
3 Beds ⋅ 2 Baths ⋅ O6452309 MLS ⋅ Park Lake Villas BLDG.
Welcome home to this beautifully maintained 3 bedroom, 2 bath, one-story condo offering 1,256 square feet of comfortable living space in one of Central Florida's most sought-after school districts, zoned for Dommerich Elementary and Maitland Middle School. This move-in-ready home features significant recent upgrades, including a brand-new roof (2024) , new HVAC system (2024), and new Electrical panel (2026), providing peace of mind and energy efficiency for years to come. Inside, you'll find a functional floor plan with spacious living and dining areas, generous bedrooms, and abundant natural light throughout. Step outside to your large, private, fully fenced back patio, ideal for entertaining, relaxing, or enjoying outdoor living. The patio offers direct access to the community pool, making it easy to enjoy Florida's year-round sunshine. Ideally located near shopping, dining, and major roadways, this home combines low-maintenance living with top-rated schools and outstanding community amenities.

1507 Grove Street, Maitland
1475 Lake Shadow Circle Unit 6205, Maitland
$199,900
2 Beds ⋅ 2 Baths ⋅ O6450405 MLS ⋅ 6 BLDG.
Step into easy, resort-style living in this beautifully updated 2-bedroom, 2-bathroom second-floor condo offering 1,048 square feet of thoughtfully designed space in the gated community of Visconti. With an open, light-filled floor plan and two spacious primary suites each with its own full bathroom this home delivers a flexible layout for everyday living. Luxury vinyl plank flooring runs throughout the entire home, giving every room a cohesive, modern look that's as durable as it is easy to maintain. The kitchen and living areas flow together seamlessly, creating a natural gathering space that keeps everyone connected, whether you're cooking dinner, watching a game, or settling in for the evening. Both suites are generously sized with ample closet space, and the split layout gives residents privacy when they want it. The bathrooms have been partially updated, offering a refreshed feel while leaving room to add your own finishing touches. Step outside to the large screened-in balcony a true extension of the living space, perfect for morning coffee, evening unwinding, or dining al fresco while overlooking the community's lush surroundings. The balcony also includes a dedicated storage area, keeping bikes, seasonal items, and outdoor gear neatly out of the way. A brand-new 2025 air conditioner adds comfort and peace of mind for years to come. The well-maintained, gated grounds feature mature landscaping and walking paths, along with a welcoming clubhouse for gatherings, two swimming pools for warm Florida afternoons, a fitness center for your daily workout, and tennis and basketball courts for friendly competition. HOA services cover water, sewer, pest control, and valet trash. Centrally located near shopping, dining, entertainment, and I-4, this condo offers easy access to Maitland, downtown Orlando, and area attractions. A great opportunity for low-maintenance living in a desirable Maitland location.

1475 Lake Shadow Circle Unit 6205, Maitland
1140 S Orlando Avenue Unit K15, Maitland
$420,000
2 Beds ⋅ 2 Baths ⋅ O6450713 MLS ⋅ K15 BLDG.
Winter Park Chain of Lakes Boat Slip Lease Included – Enjoy Boating Access with a Lease Paid in Full Through July 31, 2027, Transferable to the New Owner and Renewable! Experience the best of waterfront living at Lake Maitland Terrace with this beautifully renovated 2-bedroom, 1.5-bath condominium offering picturesque lake views, exceptional upgrades, and access to the renowned Winter Park Chain of Lakes. Imagine spending your weekends cruising the lakes, entertaining friends, or simply enjoying the waterfront lifestyle right outside your door. Inside, a sophisticated renovation brings modern elegance and functionality together. The beautifully updated kitchen features premium finishes, generous workspace, and a party-size ice maker, perfect for entertaining. The adjoining dining area offers abundant built-in storage, creating a seamless blend of style and practicality. Both bedrooms enjoy picturesque lake views, while the spacious primary suite features a walk-in closet and beautifully updated half bath. Step onto your screened front porch and take in the peaceful surroundings of this expansive lakefront community, featuring a sparkling swimming pool, fishing dock, putting green, and shuffleboard courts. Whether you're seeking a full-time residence or a seasonal retreat, this move-in-ready condominium delivers an exceptional combination of sophisticated interiors, waterfront amenities, and convenient access to one of Central Florida's most celebrated boating destinations. Your opportunity to embrace the Chain of Lakes lifestyle awaits!

1140 S Orlando Avenue Unit K15, Maitland
2122 Korat Lane, Maitland
$385,000
4 Beds ⋅ 2 Baths ⋅ O6450101 MLS
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
448 Banyon Tree Circle Unit 206, Maitland
$120,000
3 Beds ⋅ 2 Baths ⋅ O6448873 MLS ⋅ 448 BLDG.
Excellent investment opportunity in Carrington Park! This 3-bedroom, 2-bathroom condominium is located on the second floor and offers a convenient location in Maitland, with easy access to shopping, dining, major roadways, and nearby employment and educational centers. The property is currently rented for $1,650 monthly through August 31, 2027, providing rental income for the new owner from day one. The community is centrally located near the shopping and commercial areas along Howell Branch Road and SR 436, with convenient access to Full Sail University, Winter Park, and surrounding areas. The HOA covers water, sewer, and exterior maintenance, offering additional convenience for property owners. Whether you are expanding your investment portfolio or looking for a property in a desirable Central Florida location, this condo presents an excellent opportunity. Don't miss the chance to own an income-producing property in a convenient and well-connected area of Maitland!

448 Banyon Tree Circle Unit 206, Maitland
2141 Falkner Road, Maitland
$515,000
4 Beds ⋅ 3 Baths ⋅ S5159176 MLS
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
219 Quayside Circle Unit B9, Maitland
$799,000
2 Beds ⋅ 3 Baths ⋅ O6448045 MLS ⋅ Na BLDG.
Tucked inside The Moorings, one of Maitland's most charming lakeside enclaves, 219 Quayside Circle sets a new standard for the community, and it comes with its own DEEDED BOAT SLIP on Lake Maitland, your gateway to the Winter Park Chain of Lakes. This two-story townhome-style condo has been completely reworked around an open, light-filled floor plan. The kitchen takes center stage with a 13-foot island wrapped in waterfall quartz. The same quartz runs across the counters and climbs the walls as a dramatic full-height backsplash, paired with GE Monogram and Café appliances and solid wood soft-close cabinetry. In the living room, soaring ceilings frame a wood-burning fireplace, and a sunroom/den just off the dining area makes an easy spot for morning coffee, a home office or a reading nook. Upstairs, two en-suite bedrooms each offer their own private retreat. The primary features a vertical wood-slat accent wall with sconce lighting, a generous walk-in closet, and a spa-inspired bath with an oversized walk-in shower that encloses a soaking tub. Throughout the home you'll find exquisite tile work, new PGT insulated windows and Andersen French doors that pour in natural light, recessed lighting, iron stair railings, and all-new baseboards and trim. A 2023 HVAC system and water heater add peace of mind, and the attached one-car garage includes a laundry room. Residents enjoy a community pool, recreation hall and dock, with Lake Lily Park and its year-round events right nearby. Park Avenue's boutiques and restaurants are about five minutes away. Move-in ready with true lock-and-leave convenience, this is lake living without the upkeep.

219 Quayside Circle Unit B9, Maitland
1140 S Orlando Avenue Unit H-16, Maitland
$625,000
2 Beds ⋅ 1 Baths ⋅ O6438189 MLS ⋅ Hawthorne House BLDG.
EXQUISITE CONDO WITH BOAT SLIP AND DOCK ON THE WINTER PARK CHAIN OF LAKES! This stunningly reimagined corner unit boasting extra windows for light/space and a limestone porcelain zero entry threshold which extends inside-out opening out to a singular plane patio, showcasing a long lake view of Lake Maitland and extraordinary view of the morning sunrise over the lake, which is nestled on the Winter Park Chain of Lakes bordering Winter Park-and less than a mile to Park Avenue. This is penthouse style living, with a fully extensive elevated remodel by W DESIGNS LTD leaving nothing spared.As you enter the home, it features an exquisite wall of natural limestone spanning floor to ceiling which meets a beautiful and coffer ceiling of meticulously crafted millwork. An electric fireplace adds to the ambiance and is flanked by two custom bookcases. The dining area, also carries the refined custom millwork paneling throughout, with a built in banquette for seating which also provides ample storage. Aloft the solid wood dining table with custom French feather & down daybed cushions, there is a sophisticated sculpted artisanal chandelier by Cynara lined with gold leaf, lighting the area with prisms. The daybeds allow a comfortable and cozy area to watch TV. The open concept galley kitchen is completely built-in with custom paneling and cabinetry, adorned with brass cabinet pulls, and a fully integrated Fisher & Paykel paneled refrigerator . All appliances are 3 years of age with little use. Master bedroom, also features beautiful millwork throughout including a custom built-in wall unit for extra storage and custom-made bookshelves. New solid wood paneled doors are embellished with polished nickel and lucite knobs. All extra wide louvered shutters throughout, are custom hand milled shutters by Lloyd’s Shutter Shoppe. Bathroom has been redesigned with commercial grade, for longevity, seagrass wallpaper, a lacquered Italian floating vanity, marble wainscoting with architecture detail, marble shower with soaking tub, Contemporary Signature Hardware waterfall faucets offer the jewelry for the bathroom. This masterfully done jewel box, Pied-à-Terre, is the epitome of simple luxury perfectly situated in this cozy community on Lake Maitland.

1140 S Orlando Avenue Unit H-16, Maitland
223 Quayside Circle Unit C11, Maitland
$537,000
3 Beds ⋅ 3 Baths ⋅ O6447408 MLS ⋅ 223 BLDG.
Enjoy the charm of The Moorings on Lake Maitland in this inviting three-bedroom, two-and-a-half-bath townhome with an attached one-car garage. High ceilings, natural light, and warm wood flooring complement the living spaces, while a wood-burning fireplace gives the living room a welcoming focal point. The kitchen features white cabinetry with glass-front accents, stainless steel appliances, and a breakfast nook framed by a bay window. A separate dining area provides space for gathering, and French doors open to a screened porch overlooking the community’s green space and mature trees. All three bedrooms are upstairs, including the primary suite with a walk-in closet and an updated bathroom featuring a double vanity and walk-in shower. Two additional bedrooms share a full bathroom, with a convenient half bath downstairs. Plantation shutters in most rooms add character and privacy. Residents enjoy a community pool, clubhouse, and community dock on Lake Maitland. Walk over to Lake Lily Park for the Sunday morning farmers’ market or enjoy Luke’s Kitchen + Bar and Antonio’s restaurant + Italian market just across the street! Nearby Maitland Plaza and Maitland Social offer additional shopping and dining, with pharmacies, medical offices, and fitness studios also close by. Publix, Whole Foods, Nordstrom Rack, and Sephora are within a few blocks, while the hopping Winter Park Village and Park Avenue’s boutiques, restaurants, and cultural attractions are just minutes away. Convenient access to I-4 and excellent nearby public and private schools further enhance this central Maitland location.

223 Quayside Circle Unit C11, Maitland
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