Maitland Homes with Sidewalks Community Features

Maitland Homes with Sidewalks Community Features

Welcome to Maitland, Florida, a charming city that perfectly blends suburban comfort with urban convenience. Nestled just north of Orlando, Maitland boasts a rich history, vibrant culture, and a welcoming community atmosphere. With its picturesque lakes, lush parks, and tree-lined streets, it’s no wonder that residents are proud to call this city home.

Maitland is known for its exceptional quality of life, offering a range of amenities that cater to families, professionals, and retirees alike. The city features a variety of dining options, from cozy cafés to upscale restaurants, as well as boutique shops and art galleries that showcase local talent. The Maitland Art Center, a historic landmark, is a must-visit for those interested in the arts, while the scenic lakes provide ample opportunities for outdoor recreation, including boating and fishing.

For those seeking a community that prioritizes connectivity and pedestrian-friendly living, Maitland’s homes with sidewalks are a standout feature. These neighborhoods encourage residents to stroll through the streets, engage with their neighbors, and enjoy the fresh Florida air. Whether you’re taking a leisurely walk with your family, biking to the nearby park, or simply enjoying the beauty of your surroundings, the sidewalks create a sense of community and belonging.

In Maitland, every day feels like a getaway, with the convenience of city life just moments away. Explore this delightful city and discover the charm of homes with sidewalks, where community connection and comfort come together in perfect harmony. Your dream home awaits in Maitland!

Newest Maitland Homes with Sidewalks Community Features

448 Banyon Tree Circle Unit 206, Maitland
$120,000
3 Beds ⋅ 2 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code
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
1275 Lake Shadow Circle Unit 13107, Maitland
$164,900
1 Beds ⋅ 1 Baths ⋅ Visconti West SubDv. ⋅ 32751 Zip Code
Welcome to luxury, comfort, and convenience at this beautifully transformed ground-floor 1-bedroom, 1-bath condo in the gated community of Visconti West. Every square foot reflects thoughtful upgrades, quality, and style. The stylish and functional kitchen features $5,500 in brand new appliance upgrades completed in 2024, including a built-in microwave. The laundry room includes a new washer and dryer, added shelving, and cabinetry. The home has also been freshly painted throughout, creating a crisp, modern, move-in-ready feel. Additional 2024 improvements include a $10,000 bathroom remodel featuring a walk-in shower, a $1,500 double-paned bedroom window, $300 in lighted ceiling fans, and $300 in overhead lighting. All-new electrical outlets, a new fire alarm system, and new blinds add even more function and convenience. The tile floors have been professionally deep cleaned and re-grouted, and the air ducts have been cleaned too. For added peace of mind, the air conditioner was updated in August 2026 at a cost of $2,200, providing an important recent improvement to the home. Beyond the condo, enjoy the serene waterfront setting and resort-style amenities Visconti West has to offer, including a clubhouse, fitness center, playground, sparkling pool, tennis courts, sidewalks for leisurely strolls, and a designated pet-walking area. With convenient access to I-4 and close proximity to Winter Park, Altamonte Springs, and the RDV Sportsplex, this home offers an ideal combination of location, lifestyle, and extensive recent improvements. Move in, settle in, and enjoy a home where much of the updating has already been done for you.

1275 Lake Shadow Circle Unit 13107, Maitland
1100 S Orlando Avenue Unit 306, Maitland
$599,900
2 Beds ⋅ 2 Baths ⋅ West Cove SubDv. ⋅ 32751 Zip Code
Exquisitely remodeled, from top to bottom, 2 bdrm 2 bath luxury condo on Lake Maitland, the largest of the Winter Park Chain of Lakes. Enjoy panoramic lake views and unimaginable sunrises and space shuttles from your large balcony or sitting in your living room or kitchen or from your primary bedroom. Home features EVERYTHING NEW, electrical, plumbing, ductwork, fixtures, appliances; beautiful crown moldings, engineered wood floors, built-ins, spacious baths -- while located in the heart of Maitland walking distance to the Enzian, Lake Lilly, and several restaurants. Easy access to I-4 and major roads and a 5 minutes drive to shopping and restaurants on Winter Park's Park Avenue. Community features a clubhouse, fitness center, large pool and spa, kayak racks, patio and grilling area. Fee includes internet/cable; water, sewer, trash and on-site management. Enjoy condo living at its finest.

1100 S Orlando Avenue Unit 306, Maitland
1140 S Orlando Avenue Unit H-16, Maitland
$625,000
2 Beds ⋅ 1 Baths ⋅ Lake Maitland Terrace SubDv. ⋅ 32751 Zip Code
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
1161 Charming Street, Maitland
$585,000
4 Beds ⋅ 4 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code
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
1931 Michael Tiago Circle, Maitland
$445,000
3 Beds ⋅ 3 Baths ⋅ Maitland Village SubDv. ⋅ 32751 Zip Code
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
200 Seneca Trail, Maitland
$550,000
3 Beds ⋅ 2 Baths ⋅ Dommerich Estates 1st Add SubDv. ⋅ 32751 Zip Code
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
508 Banyon Tree Circle Unit 200, Maitland
$149,900
2 Beds ⋅ 2 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code
MUST SEE! Well-maintained and move-in-ready 2-bedroom, 2-bath second-floor condo in the desirable Carrington Park community of Maitland. Offering 1,200+ square feet, this spacious split-bedroom floor plan features generously sized bedrooms, an open living/dining area, and a private screened balcony—perfect for enjoying the Florida lifestyle. The unit also includes a private washer/dryer hookup for added convenience. Enjoy an exceptional location near the intersection of Howell Branch Road and SR-436, with Publix, Starbucks, shopping, dining, and everyday conveniences just minutes away. Full Sail University is approximately 10 minutes away, UCF is nearby, and Orlando’s major attractions are easily accessible. Carrington Park offers two swimming pools, a large fitness center, playground, and beautifully maintained green spaces. The HOA provides excellent value by including water, sewer, trash, building insurance, roof, grounds maintenance, and community pool maintenance. Currently leased through December 31, 2026 at $1,700/month, providing immediate rental income for an investor while preserving future flexibility for an owner occupant. Seller financing may be available with $50,000 down and acceptable terms. A great opportunity for an owner occupant or investor looking for space, location, amenities, and value in a desirable Maitland area. Come see it in person—this is one you won’t want to overlook. Schedule your showing today and bring your offer!

508 Banyon Tree Circle Unit 200, Maitland
559 Flemming Way Unit 203, Maitland
$108,000
1 Beds ⋅ 1 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code
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
1225 Lake Shadow Circle Unit 14102, Maitland
$205,900
2 Beds ⋅ 2 Baths ⋅ Building 14 Visconti West SubDv. ⋅ 32751 Zip Code
Auction Property. Auction Property. AUCTION/OCCUPIED. Buyers will be required to sign a occupancy declaration. 2-bedroom 2-bathroom condominium in gated community of Visconti West situated off Lake Shadow. Quick access to interstate 4 and Florida turnpike. Property is sold “as is” with NO property disclosures, NO inspection reports, NO interior photos, NO lease in place, NO access- The seller does not represent or guarantee occupancy status. NO VIEWINGS of this property. Please DO NOT DISTURB the occupant. Buyer is responsible for obtaining possession of the property upon closing.

1225 Lake Shadow Circle Unit 14102, Maitland
2308 Haywood Court Unit 100, Maitland
$215,000
3 Beds ⋅ 2 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code
Need Room! Welcome home to this spacious 1612 S.F. first-floor condominium featuring three bedrooms and two full baths in a well-maintained community conveniently located near shopping, dining, and Full Sail University. Step inside to find brand-new luxury plank flooring throughout the living and bedroom areas, ceramic tile in the kitchen and bathrooms, and absolutely no carpet! Blinds on all windows and ceiling fans add to the comfort and convenience of this inviting home. The kitchen comes complete with refrigerator, range, microwave, and dishwasher, while a brand-new washer and dryer are also included. Relax and enjoy Florida's beautiful weather year-round from your private screened-in lanai, with the community pool and playground conveniently located nearby. The HOA offers exceptional value by covering water, sewer, trash, building insurance, roof, grounds maintenance, and the community pool. With its desirable first-floor location, fresh updates, generous three-bedroom floor plan, and convenient location, this condo offers easy Florida living and is ready for you to make it home!

2308 Haywood Court Unit 100, Maitland
2637 Legacy Villas Drive Unit 2637, Maitland
$200,000
2 Beds ⋅ 2 Baths ⋅ Visconti East SubDv. ⋅ 32751 Zip Code
Welcome to 2637 Legacy Villas Drive, a spacious 2-bedroom, 2-bath residence located in the gated Visconti community in Maitland. Offering 1,280 square feet of living space, this home features a comfortable and functional floor plan along with the added convenience of a private 2-car garage. Enjoy everything the Visconti community has to give, including a resort-style swimming pool, clubhouse, fitness center, tennis courts, basketball courts, playground, and gated entry. The community's recreational spaces and amenities provide plenty of opportunities to enjoy the Central Florida lifestyle. Conveniently located in Maitland with easy access to I-4 and major roadways, the property offers a short commute to Downtown Orlando and convenient access to shopping, dining, entertainment, and employment centers throughout the Orlando area. Whether you're looking for a primary residence or an investment opportunity, this 2-bedroom, 2-bath home combines generous living space, a private 2-car garage, desirable community amenities, and a convenient Maitland location.

2637 Legacy Villas Drive Unit 2637, Maitland
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