Maitland Homes with HOA

Maitland Homes with HOA

Welcome to Maitland, Florida – a charming city that blends suburban tranquility with vibrant community life. Nestled just north of Orlando, Maitland is renowned for its picturesque lakes, lush parks, and a rich cultural scene that makes it a desirable place to call home. With a population that values community spirit and an array of amenities, Maitland offers residents a perfect balance of comfort and convenience.

One of the standout features of living in Maitland is the availability of homes within Homeowners Associations (HOA). These communities not only provide a sense of security but also foster a strong sense of belonging among residents. With well-maintained landscapes, shared recreational facilities, and organized social events, HOA communities in Maitland enhance the living experience, ensuring that your neighborhood remains beautiful and inviting.

Maitland boasts a diverse real estate market, with options ranging from charming single-family homes to modern townhouses, many of which are part of these well-managed HOA communities. Homeowners can enjoy amenities such as swimming pools, tennis courts, and community parks, making it easy to connect with neighbors and enjoy an active lifestyle.

In addition to its residential appeal, Maitland is conveniently located near major highways, making commuting to Orlando and beyond a breeze. With top-rated schools, delightful dining options, and a variety of shopping experiences, Maitland stands out as a wonderful place to settle down and grow.

Experience the warmth and charm of Maitland – where your dream home awaits within a welcoming community!

Newest Maitland Homes with HOA

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 first 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
1161 Charming Street, Maitland
$585,000
4 Beds ⋅ 4 Baths ⋅ O6446305 MLS ⋅ 1161 BLDG.
Sunrises over Lake Charity, two primary suites, and a kitchen made for serious cooking — this Montacino townhouse isn’t like anything else on the market. With 4 bedrooms, 3.5 baths, and new luxury vinyl flooring throughout, it’s effortlessly modern and move-in ready. The first-floor primary suite offers single-level living with a spa-inspired bathroom with two vanities, a tub and shower and generous closet space. The second-floor primary provides a private retreat for guests or family — a rare and highly sought-after layout. The brand new LG induction oven with air fryer and Café double dishwasher make cooking and cleaning a breeze, and the private back patio is perfect for morning coffee, entertaining or evening relaxation. An extra-large two-car garage adds plenty of storage for bikes, tools, or hobbies. Nestled in a gated community with a pool, this home blends comfort, security, and lifestyle convenience. With minutes to I-4, Winter Park, Downtown Orlando, and all of Maitland’s best dining and shopping are within easy reach. A rare floor plan, thoughtful updates, and flexible living spaces — this Montacino gem truly stands apart.

1161 Charming Street, Maitland
1010 Winderley Place Unit 100, Maitland
$349,000
2 Beds ⋅ 3 Baths ⋅ O6444498 MLS
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
1931 Michael Tiago Circle, Maitland
$445,000
3 Beds ⋅ 3 Baths ⋅ O6445127 MLS ⋅ 1931 BLDG.
Welcome to this beautiful 3-bedroom, 2.5-bath townhome offering approximately 2,100 square feet of comfortable living space in the gated community of Maitland Village. The open floor plan features spacious living and dining areas with abundant natural light, creating an inviting setting for everyday living and entertaining. The kitchen flows seamlessly into the main living areas, while all three bedrooms are located upstairs for added privacy. The generous primary suite provides a relaxing retreat with an en-suite bathroom and ample closet space. Additional features include an interior laundry area, a private outdoor patio, and an attached two-car garage. Maitland Village offers gated access, a community pool, clubhouse, sidewalks, and beautifully maintained surroundings, also includes water, Cable & internet . Conveniently located near I-4, Maitland Center, Winter Park, Downtown Orlando, shopping, dining, and entertainment. Schedule your private showing and discover the space, convenience, and lifestyle this Maitland townhome has to offer!

1931 Michael Tiago Circle, Maitland
1519 Glastonberry Road, Maitland
$525,000
4 Beds ⋅ 2 Baths ⋅ O6446901 MLS
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 ⋅ O6445899 MLS
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
559 Flemming Way Unit 203, Maitland
$108,000
1 Beds ⋅ 1 Baths ⋅ O6441148 MLS ⋅ 559 BLDG.
Virtually Staged. Welcome to this well-maintained and move-in-ready second-floor condo, offering comfort, convenience, and a great location! This charming 1-bedroom, 1-bathroom unit features a spacious layout, a large walk-in closet, and a private outdoor patio where you can enjoy your morning coffee or relax after a long day. The property is currently vacant and ready to show, making it an excellent opportunity for a first-time homebuyer, seasonal resident, or investor looking for a low-maintenance property. The community offers a variety of desirable amenities, including a beautiful swimming pool, playground, and green spaces, and a great fitness/exercise room for residents to enjoy. The low HOA fee makes this property even more attractive for those looking for an affordable and convenient lifestyle. Laundry facilities are conveniently located outside across from the building. Located in a convenient area close to public transportation, stores, shops, restaurants, and everyday necessities, this condo provides easy access to everything you need. Whether you are looking for a comfortable place to call home or a great investment opportunity, this property offers an excellent combination of location, amenities, affordability, and convenience. Don't miss the opportunity to see this beautiful second-floor condo. The unit is vacant, in good condition, and ready for its new owner. Schedule your showing today!

559 Flemming Way Unit 203, Maitland
2520 Caper Lane Unit 204, Maitland
$130,000
1 Beds ⋅ 1 Baths ⋅ O6437762 MLS ⋅ 2520 BLDG.
**LOCATION, LOCATION!** Welcome to this charming and cozy 1-bedroom, 1-bathroom condo, ideally located in a convenient and desirable area near Semoran Blvd and Howell Branch Rd. This move-in-ready second-floor unit offers comfort, convenience, and easy access to everything you need. Enjoy being just walking distance from shopping, restaurants, supermarkets, and everyday essentials. The community offers a refreshing swimming pool, perfect for relaxing or enjoying quality time with family and friends, as well as ample parking for residents and guests. The property is also conveniently located near schools and educational institutions, including Rollins College, making it an excellent opportunity for professionals, or anyone looking for a convenient Central Florida location. HOA includes water, adding even more value and convenience. Whether you're looking for your next home, a low-maintenance place to live, or an investment opportunity, this condo is one you won't want to miss! Schedule your showing today and come see all this property has to provide.

2520 Caper Lane Unit 204, Maitland
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