Maitland Homes with Sidewalks Community Features

Maitland Homes with Sidewalks Community Features

Welcome to Maitland, Florida – a hidden gem nestled in the heart of Orange County! Known for its rich history, picturesque lakes, and vibrant community, Maitland offers a unique blend of suburban charm and urban convenience. With its lush greenery and scenic landscapes, this city is perfect for those who appreciate the beauty of nature while still enjoying a close-knit community atmosphere.

Maitland is not just a beautiful place to live; it’s also a hub of cultural activities. With a variety of art galleries, theaters, and annual festivals, residents are never short of entertainment options. The city’s commitment to preserving its historical roots is evident in its charming architecture and well-maintained parks, making every stroll through the neighborhood a delightful experience.

One of the standout features of homes in Maitland is the community-focused design, particularly in neighborhoods with sidewalks. These homes promote an active lifestyle, encouraging residents to take leisurely walks, jog, or bike around the area while fostering connections with neighbors. Sidewalks create a safe and inviting environment for families, allowing kids to play outside and meet new friends.

In addition to the beautiful homes, residents enjoy easy access to top-rated schools, shopping centers, and dining options, making Maitland not just a place to live, but a place to thrive. Whether you’re looking for a cozy bungalow or a spacious family home, Maitland’s homes with sidewalks provide the perfect foundation for a vibrant, fulfilling lifestyle. Discover the charm of Maitland, where community and convenience come together in perfect harmony!

Newest Maitland Homes with Sidewalks Community Features

$219,900
2 Beds ⋅ 2 Baths ⋅ Visconti East SubDv. ⋅ 32751 Zip Code
Impressive - 2 bedroom 2 bath condo on first floor in resort style community of Visconti Maitland. This recently remodeled unit features designer paint throughout, berber carpet, new ceramic tile, a gourmet kitchen with contemporary light grey cabinets, stainless steel appliances and laundry room with w/d hook ups. Community offers its residents 2 tropical pools overlooking Lake Shadow, a fitness center, tennis - and basket ball court and car wash area. Located within minutes to major shopping, entertainment and I-4.

1475 Lake Shadow Circle Unit 6105, 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
$179,990
2 Beds ⋅ 2 Baths ⋅ Cherrywood Gardens SubDv. ⋅ 32751 Zip Code
Don't miss this fantastic opportunity to own this cozy 2 bedroom 1.5 bath condo in the heart of Maitland. The owner's suite is well equipped with a walk-in closet and ensuite. This unit includes all appliances, spacious living room, covered front porch, screened-in back porch overlooking the courtyard, and 2 reserved parking spaces right in front. Additional guest parking is also available. This quiet, small, and well- maintained community is surrounded with mature trees and pathways. Association fees cover community pool, water, sewer, trash, exterior maintenance, and ground maintenance making for worry-free living. Very convenient and close to shopping, dining, and major roadways. Whether you’re a first-time buyer, downsizing, or looking for an investment, this condo is a great opportunity to own in the desirable Maitland area.

336 Cherrywood Gardens Drive Unit 336, Maitland
$315,000
2 Beds ⋅ 2 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code
Completely renovated and move-in ready, a desired first-floor unit in the sought-after Lake Maitland Terrace! This impeccably updated two-bedroom, 1.5-bath condominium blends modern style with an unbeatable lakeside location in the heart of the Maitland/Winter Park area. Thoughtfully redesigned throughout, the home showcases a new kitchen with fresh cabinetry, granite countertops and stainless steel appliances. The baths have been tastefully reimagined with contemporary finishes, and stylish updates continue across the entire unit, delivering a turnkey home you can move into with confidence. The comfortable two-bedroom layout features a full bath in the hall plus a convenient half bath tucked within one of the bedrooms. Sunlight pours through large windows, and the easy first-floor accessibility makes everyday living a breeze. A space-saving washer/dryer combo is conveniently inside the unit, and a dedicated parking space adds day-to-day ease. Set within Lake Maitland Terrace, residents enjoy an amenity-rich community on the shores of Lake Maitland within the famed Winter Park Chain of Lakes. Take in the sparkling community pool with beautiful lake views, gather at the clubhouse with a full kitchen, and enjoy lake access from the private dock and fishing pier, plus kayak racks and tree-lined sidewalks throughout. Ideally just minutes from the charming shops, restaurants, and entertainment of downtown Maitland and Winter Park, you can walk to Lake Lily Park's popular events and the Enzian Theater, and reach Winter Park Village and Park Avenue in no time. Zoned for top-rated schools Dommerich Elementary, Maitland Middle and Winter Park High, this beautifully updated home is ready to impress. Whether you're seeking a primary residence or a seasonal retreat, don't miss your chance to claim this exceptional lakeside gem as your own.

1140 S Orlando Avenue Unit G-3, Maitland
$219,900
2 Beds ⋅ 2 Baths ⋅ Visconti East SubDv. ⋅ 32751 Zip Code
Exceptional - 2 bed 2 bath condo on 1st floor in resort style community of Visconti. Featuring designer paint throughout, plush carpeting, a gourmet kitchen with newer appliances, laundry room with full size washer/dryer hook ups and screened in patio with outside storage. Community offers its residents 2 tropical pools overlooking Lake Shadow, Gym, Tennis - and basketball court, play ground and clubhouse. Located within minutes to major shopping, entertainment and Interstate 4. Call and schedule your private showing today !

1100 Lake Shadow Circle Unit 2103, Maitland
$259,000
2 Beds ⋅ 3 Baths ⋅ Park Lake Grove Condo Ph C SubDv. ⋅ 32751 Zip Code
Welcome home to this beautifully updated two-story condo nestled in one of Maitland's most established communities, where lush mature landscaping, winding sidewalks, a community pool, lake access and a private dock create a peaceful setting just minutes from some of Central Florida's favorite restaurants, shopping and entertainment. Enjoy easy access to Enzian Theater, Winter Park Village, Trader Joe's, Whole Foods, Park Avenue and countless local dining favorites all within minutes. Inside, you'll immediately notice one of this home's most unique features. The floor plan was thoughtfully reimagined to create an expansive open-concept living space centered around a beautifully enlarged kitchen—offering a layout rarely available within the community. Warm cabinetry, stainless steel appliances, a center island, under cabinet lighting, recessed lighting and abundant workspace make this kitchen equally suited for everyday living and entertaining. Ceramic tile flooring flows throughout the entire first floor, while upstairs features durable laminate wood flooring throughout both bedrooms. Each bedroom serves as its own private primary suite with an ensuite bathroom, providing exceptional flexibility for guests, roommates or multi-generational living. One suite features a tub/shower combination while the other offers a walk-in shower. A third full bathroom downstairs with a walk-in shower adds additional convenience for visitors. Additional highlights include a re-roof (2021), energy-efficient double-pane windows and sliding glass door (updated 2023), a dedicated interior laundry room complete with cabinetry and folding counter, attractive 5¼-inch baseboards throughout the main living area, and a private rear courtyard that connects to the garage—perfect for grilling, outdoor dining, container-gardening or additional storage. Combining an exceptional location, a one-of-a-kind floor plan, and low-maintenance living in the heart of Maitland and minutes from Winter Park, this home offers a rare opportunity to enjoy both convenience and comfort in one of Central Florida's most desirable areas.

1713 Gulfview Drive Unit 435B, 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
$259,000
3 Beds ⋅ 3 Baths ⋅ Park Lake Grove Condo SubDv. ⋅ 32751 Zip Code
Welcome home to this spacious 3-bedroom, 2.5-bath condo in the desirable Park Lake Grove community. Enjoy peaceful lake views from your living room, and the convenience of an attached 1-car garage. The thoughtfully designed floor plan offers generous living space, 2 primary bedrooms with en suites upstairs, natural light, and plenty of storage. Community amenities include a pool and lake access. Conveniently located near shopping, dining, major highways, and downtown Orlando.

603 Waverly Lane Unit 405B, Maitland
$189,900
2 Beds ⋅ 2 Baths ⋅ Visconti West SubDv. ⋅ 32751 Zip Code
Welcome home to this beautifully updated and maintained 2-bedroom, 2-bath corner unit condo at Visconti West in Maitland! Located on the third floor, this light filled home features vaulted ceilings and an open, airy floor plan designed for comfortable living. The spacious primary suite includes an en-suite bathroom, while both bedrooms offer generous walk-in closets. The kitchen and bathrooms feature upgraded granite countertops and luxury vinyl plank flooring throughout the entryway, kitchen and bathrooms. Enjoy your morning coffee or unwind in the evening on the screened balcony. Additional highlights include an in-unit laundry room with washer and dryer, AC unit (2023), and hot water heater (2025). Residents enjoy gated access and resort style amenities including a pool, fitness center, clubhouse, tennis court, basketball court, valet trash pickup Monday through Friday, and a scenic pond and lake. Conveniently located just minutes from I-4, shopping, dining and entertainment, this home offers the perfect blend of style, comfort, and an unbeatable location.

1475 Lake Shadow Circle Unit 6307, Maitland
$420,000
2 Beds ⋅ 2 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code
Welcome to Lake Maitland Terrace, where this beautifully renovated condominium offers a rare opportunity to enjoy Chain of Lakes living. Included with the property is a leased boat dock on the Winter Park Chain of Lakes, paid through 7/31/2027, with the lease transferable to the new owner and renewable. This stunning 2-bedroom, 1.5-bath residence features picturesque lake views from both bedrooms as well as the screened front porch. The screened-in front porch is the perfect place to relax while overlooking the expansive lakefront campus, complete with a sparkling pool, fishing dock, putting green, and shuffleboard courts. From the moment you step inside, you'll appreciate the exceptional quality of the modern renovation, thoughtfully designed with both style and function in mind. The beautifully updated kitchen is ideal for entertaining, featuring premium finishes, generous workspace, and a party-size ice maker. It flows seamlessly into the dining area, where abundant built-in storage provides both convenience and organization. The spacious primary suite serves as a private retreat, complete with a walk-in closet, an updated half bath, and tranquil lake views to wake up to each morning. Whether you're looking for a full-time residence or a weekend escape, this move-in-ready home offers an exceptional lifestyle in one of Winter Park's most desirable waterfront communities. This is a rare opportunity you won't want to miss.

1140 S Orlando Avenue Unit K15, Maitland
$195,900
1 Beds ⋅ 1 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code
LAKE ACCESS LIVING in one of Central Florida's most desirable locations! Welcome to 1140 S. Orlando Ave E11, a move in ready condo ideally located on the Winter Park and Maitland border in the sought after Lake Maitland Terrace community. Enjoy private access to Lake Maitland, part of the prestigious Winter Park Chain of Lakes, where you can spend your days paddle boarding, kayaking, boating, fishing, or simply relaxing by the water. Community amenities include a brand new lakefront pool, clubhouse available for private events, shuffleboard, putting green, community laundry facilities, COMMUNITY DOCK and additional storage. Inside, you'll find a functional floor plan with separate living and dining spaces, abundant natural light, and a well maintained interior that's ready to enjoy or personalize over time. Whether you're looking for a primary residence, seasonal retreat, or investment opportunity, this condo offers exceptional value in an unbeatable location. Just minutes from Park Avenue and walking distance to local favorites including the Enzian Theater, Eden Bar, Luke's Kitchen and Bar, Antonio's, Francesco's, the Shoppes at Maitland, and beautiful Lake Lily Park. With easy access to downtown Winter Park, downtown Orlando, I 4, shopping, dining, and entertainment, this is low maintenance Florida living at its best.

1140 S Orlando Avenue Unit E11, Maitland
$1,150,000
5 Beds ⋅ 4 Baths ⋅ Maitland Club Rep SubDv. ⋅ 32751 Zip Code
Move-In Ready. Welcome to the Premier community of Maitland Club. The paver walkway and covered front patio lead you into the spacious foyer, featuring the elegant formal living and dining rooms with hardwood floors, crown molding and plantation shutters. The Kitchen features Granite countertops, 42” cabinets and lots of natural light. The warm and inviting family room area offers a woodburning fireplace with built-in shelving and an open floor plan. The 1st Floor Master has a Large Walk-in closet and master bathroom. Separate shower and Granite countertops. Upstairs boasts a Bonus Room, ample built-in storage, and a 5th Bedroom with a large Walk-in closet. Vaulted Ceilings throughout. The Screened Pool, Covered Lanai, and Large Fenced yard are great for entertaining. The community offers tennis and basketball courts and a 24-hour guard gated community. New roof in 2024 ($80,000 value). The carpet in the home was replaced in 2020.New A/C replacement in 2024.Termite bond which is transferable. TV's convey with the home in the living room. Pool has been resurfaced. The master bath and kitchen have been updated. Move-In Ready. This home is located within minutes of downtown Winter Park, Maitland Town Center, shopping, restaurants, hospitals, Genesis Health Club and easy access to I-4.

900 Brightwater Circle, Maitland
Start Your Search