Winter Park Homes with Sidewalks Community Features

Winter Park Homes with Sidewalks Community Features

Welcome to Winter Park, a charming city located in the sunny state of Florida. Known for its picturesque scenery, vibrant community, and rich history, Winter Park offers residents a perfect blend of small-town charm and big-city amenities.

One of the standout features of Winter Park is its Homes with Sidewalks Community. True to its name, this community is designed to promote a pedestrian-friendly lifestyle, where residents can easily walk or bike to nearby parks, shops, and restaurants. The presence of sidewalks not only enhances the aesthetic appeal of the neighborhood but also fosters a sense of community spirit as neighbors come together for leisurely strolls or outdoor gatherings.

Living in a Homes with Sidewalks Community in Winter Park means enjoying a healthy and active lifestyle, with ample opportunities for outdoor activities and social interactions. Whether you're taking a leisurely walk with your furry friend, jogging in the morning sun, or simply enjoying a leisurely stroll with your loved ones, the sidewalks offer a safe and convenient way to explore the beauty of Winter Park.

With its welcoming community, beautiful homes, and convenient amenities, Winter Park's Homes with Sidewalks Community is the perfect place to call home. Come and experience the warmth and charm of Winter Park living – where every sidewalk leads to new adventures and lasting memories.

Newest Winter Park Homes with Sidewalks Community Features

200 St Andrews Boulevard Unit 906, Winter Park
$175,000
1 Beds ⋅ 1 Baths ⋅ Four Seasons Condo SubDv. ⋅ 32792 Zip Code
Your Winter Park Lifestyle Starts Here! Move right into this beautifully updated, modern 1-bedroom, 1-bath condo and enjoy the perfect blend of style, comfort, and convenience. With a desirable first-floor location, no stairs, spacious interiors, and no carpet throughout, this move-in-ready home is ideal for buyers seeking easy, low-maintenance living in one of Winter Park’s most sought-after areas. Whether you’re searching for your own stylish retreat or a smart investment opportunity, this condo delivers exceptional value and a lifestyle you’ll love. The welcoming entryway features a convenient coat closet, while the bright, oversized eat-in kitchen offers plenty of room for a full-size table and chairs, plus abundant countertop space with room for barstools. The massive living room opens through French doors to a screened-in porch, creating the perfect spot to relax and enjoy the Florida lifestyle. The oversized, light-filled bedroom boasts an enormous walk-in closet, and the beautifully updated bathroom features a large step-in shower. Storage is a standout bonus, with a private closet on the screened porch and an additional large storage closet just outside the front door. Enjoy resort-style community amenities, including sparkling swimming pools, a clubhouse, and tennis courts. Just steps from lovely parks and trails, and minutes from Park Avenue’s charming shops, restaurants, and cafés, this prime location also offers convenient access to grocery stores, medical centers, Baldwin Park, and an easy route to Orlando International Airport. Stylish, spacious, and ideally located—this Winter Park gem is ready to welcome you home. Schedule your private showing today!

200 St Andrews Boulevard Unit 906, Winter Park
1552 Little Wren Lane, Winter Park
$440,000
3 Beds ⋅ 3 Baths ⋅ Enclave At Hawks Crest SubDv. ⋅ 32792 Zip Code
Welcome to 1552 Little Wren Lane, a beautifully maintained 3-bedroom, 2.5-bath townhome in the Enclave at Hawks Crest, one of Winter Park's most desirable newer communities. A paver driveway and 2-car garage set the tone before you step inside to a bright, open main floor where tile flows through the living and dining areas into a kitchen made for gathering. Crisp white shaker cabinetry, granite countertops, stainless steel appliances, and a generous island with room to sit and stay awhile. Sliding doors lead to a covered patio overlooking peaceful green space, perfect for morning coffee or winding down at the end of the day. Upstairs, a versatile loft gives you a home office, media room, or play space. The spacious primary suite features a tray ceiling, dual walk-in closets, and a spa-like bath with double granite vanities and a glass-enclosed shower. Two more bedrooms, a full hall bath, and a dedicated laundry room with washer and dryer included round out the second floor, with a powder room downstairs for guests. Residents enjoy a community pool, scenic ponds, and a low-maintenance lifestyle minutes from Park Avenue and Rollins College. Move-in ready — schedule your showing today!

1552 Little Wren Lane, Winter Park
3027 Aaron Bur Avenue Unit L1, Winter Park
$169,999
2 Beds ⋅ 3 Baths ⋅ Colonies SubDv. ⋅ 32792 Zip Code
STUNNING FULLY REMODELED TWO-STORY CORNER-UNIT CONDO IN THE HEART OF WINTER PARK! GREAT OPPORTUNITY FOR HOMEOWNERS AND INVESTORS! Welcome to this beautifully renovated 2-bedroom, 2.5-bathroom, two-story corner-unit condo featuring modern finishes, gorgeous flooring, a stylish kitchen with stainless steel appliances, a BRAND-NEW A/C UNIT, and beautiful upgrades throughout! The first floor offers a spacious living area, a convenient half bathroom, and an indoor laundry closet with washer and dryer. Upstairs, you'll find two comfortable bedrooms, each with its own full bathroom, offering privacy and functionality. Enjoy the community swimming pool, ample parking, and a desirable location tucked toward the back of the community, away from the main commercial activity. LOCATION, LOCATION, LOCATION! Enjoy the convenience of nearby shopping, restaurants, cafés, and everyday essentials within walking distance! Located just minutes from Winter Park's famous Park Avenue, Rollins College, Winter Park Village, Full Sail University, beautiful parks, and Downtown Orlando, with easy access to major roadways. INVESTORS TAKE NOTICE! This move-in-ready, fully remodeled condo offers an attractive investment opportunity in a convenient Winter Park location, close to universities, employment centers, shopping, dining, and entertainment. Whether you're looking for a primary residence or an investment property, this condo offers modern upgrades, comfort, and convenience! Some photos have been virtually staged to illustrate the property's potential.

3027 Aaron Bur Avenue Unit L1, Winter Park
2352 Sun Valley Circle, Winter Park
$280,000
2 Beds ⋅ 2 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code
Welcome to the established and well-maintained community of Cedarwood Village in highly desirable Winter Park! TREE-LINED STREETS lead to this END UNIT, COMPLETELY REMODELED IN 8/2026 and MOVE-IN READY. This 2-bedroom, 2-bath, BLOCK-CONSTRUCTED condominium offers nearly 1,500 square feet of interior living space and includes a versatile LOFT. As you enter the foyer, you’ll immediately appreciate the attention to detail and pride of ownership, with WOOD FLOORS and fresh neutral paint setting the tone for a stylish and inviting interior. The GREAT ROOM is truly the centerpiece of the home, featuring dramatic 2-story VAULTED CEILINGS that create an exceptionally open, voluminous, and luxurious atmosphere. A magnificent corner focal point showcases a cozy WOOD-BURNING FIREPLACE with raised slate tile hearth, while mantle columns extend the full height of the room and frame a soaring vertical mirror that reflects natural light and visually expands the space. TWO SKYLIGHTS further enhance the natural light. From the living area, enjoy serene views of the lanai and lush GREEN SPACE beyond. A stylish WET BAR is tucked into a recessed alcove and beautifully illuminated by warm integrated accent lighting, featuring a POLISHED GRANIT COUNTERTOP and contemporary shaker-style cabinetry—perfect for entertaining. The second-story LOFT provides an incredible overlook into the Great Room below and serves as a highly desirable FLEX SPACE, complete with BLACK WROUGHT-IRON SPINDLE RAILING, modern neutral carpeting, its own SKYLIGHT, and a convenient STORAGE CLOSET. The kitchen features sleek light-gray SHAKER-STYLE CABINETRY, elegant GRANITE COUNTERTOPS, and premium STAINLESS-STEEL APPLIANCES. An oversized peninsula island with deep undermount sink and gooseneck faucet doubles as a breakfast bar for casual dining and entertaining. A charming EAT-IN NOOK overlooks the PRIVATE COURTYARD and provides access through wide sliding glass doors, creating the perfect spot for morning coffee or outdoor dining. For added convenience, the laundry closet, complete with WASHER AND DRYER, is conveniently located within the kitchen. The PRIMARY SUITE offers a peaceful retreat with both WALK-IN and step-in closets, direct lanai access through sliding glass doors, and a beautifully REMODELED ENSUITE BATH accessed through a stylish modern barn door. The bath features a DUAL-SINK VANITY, large walk-in shower with frameless glass door, and private water closet. The spacious SECOND BEDROOM also features a WALK-IN CLOSET and convenient access to the REMODELED HALL BATH, providing privacy for residents while comfortably serving guests. Additional features include a location directly across from green space, 2 DESIGNATED PARKING spaces in front, and a PRIVATE MAILBOX. With LOW HOA DUES, residents enjoy a sparkling community pool, clubhouse, tennis and basketball courts, pickleball, FENCED DOG RUN, and pet walk with waste stations. Monthly fees also include ROOF AND EXTERIOR BUILDING MAINTENANCE, PEST CONTROL, and LANDSCAPING. This ideal Winter Park location is directly across from Casselberry Commons, offering a variety of major retailers, Publix, and fast-food options. Just minutes from Park Avenue, UCF, Rollins College, Full Sail University, shopping, restaurants, entertainment, and medical facilities, this exceptional home combines sophisticated living with convenience in one of Central Florida’s most desirable locations. See video and virtual tour.

2352 Sun Valley Circle, Winter Park
4786 Tangerine Avenue Unit 4786, Winter Park
$220,000
2 Beds ⋅ 2 Baths ⋅ Wrenwood Condo SubDv. ⋅ 32792 Zip Code
Discover comfort, style, and convenience in the heart of Winter Park! This beautifully updated 2-bedroom, 1.5-bathroom, two-story condominium offers approximately 1,281 square feet of living space with a spacious, functional layout designed for everyday living and entertaining. Step inside to find ceramic tile flooring, an inviting living and dining area, and a beautifully appointed kitchen featuring granite countertops, attractive cabinetry, a stylish backsplash, and stainless steel appliances. Upstairs, you'll find two generously sized bedrooms, including a primary bedroom with a walk-in closet. Enjoy your morning coffee or unwind in the evening on the private screened-in porch overlooking a peaceful green space, complete with an additional storage closet. Interior laundry adds everyday convenience. Located in the established Wrenwood condominium community, residents enjoy access to a community swimming pool and clubhouse. The property also offers two assigned parking spaces and convenient access to major roads, shopping, restaurants, and entertainment. LOCATION, LOCATION, LOCATION! Just minutes from Full Sail University, UCF, Rollins College, Downtown Winter Park, and the popular Park Avenue shopping and dining district. Whether you're searching for your primary residence or an investment opportunity, this property offers an appealing combination of location, space, and convenience. Don't miss this opportunity to own a condominium in desirable Winter Park! Schedule your private showing today!

4786 Tangerine Avenue Unit 4786, Winter Park
1458 Lone Feather Trail, Winter Park
$650,000
4 Beds ⋅ 3 Baths ⋅ Landings At Hawks Crest SubDv. ⋅ 32792 Zip Code
Virtually Staged. Set within the guard-gated community of Hawk’s Crest, this inviting single-story residence offers a beautifully maintained open floor plan with more than 1,700 square feet of comfortable living space and approximately $15,000 in luxurious recent upgrades. Fresh interior paint and neutral finishes create a bright, welcoming atmosphere, complemented by ceramic tile flooring throughout the main living areas and new carpeting in the bedrooms. At the heart of the home, the spacious kitchen features gray cabinetry, a new range and oven, stainless steel appliances, generous counter space, an expansive center island and a large pantry, opening seamlessly to the dining and living areas. The primary suite offers a spacious retreat with a walk-in closet and an en-suite bath featuring dual vanities and a walk-in shower, while additional bedrooms provide flexibility for family, guests or a home office. Sliding glass doors extend the living space to the screened lanai, enhanced with updated decking and an inviting setting for outdoor relaxation. Beyond the lanai, the fully fenced backyard, featuring newly installed fencing and landscaping, offers additional privacy and ample space for outdoor enjoyment. Residents of Hawk’s Crest enjoy resort-style amenities, including a community pool, clubhouse, fitness center, splash pad, playgrounds, dog park and private access to Lake Howell, along with the convenience of Park Maitland Preschool, Kelly’s Ice Cream and Foxtail Coffee at the community entrance. Ideally positioned near Winter Park’s renowned shopping, dining and everyday conveniences, this home offers an exceptional opportunity to enjoy the Hawk’s Crest lifestyle.

1458 Lone Feather Trail, Winter Park
1600 Legion Drive, Winter Park
$3,495,000
5 Beds ⋅ 6 Baths ⋅ Green Oaks Rep SubDv. ⋅ 32789 Zip Code
Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Keith D. Field. Conceived as the opposite of a production home, it was crafted with a builder’s eye for structural integrity, thoughtful flow, and a seamless connection between indoors and out. Set on a generous 91-foot wide lot, this custom residence offers 5 bedrooms and a floor plan that feels both substantial and inviting. A wide front veranda sets a timeless tone from the moment you arrive. Dark-framed windows and doors create a striking contrast, while manicured hedges and brick-paved drives enhance the classic curb appeal and highlight the home’s architectural details. Step inside and you immediately sense that this is more than just a beautiful house—it’s a home with a story. At its heart is the reclaimed pine flooring, sourced from a Florida bridge. Rich with character, worn in all the right ways, these floors bring a warmth and authenticity you simply cannot replicate with something new. A long, gracious foyer introduces the main living spaces. To your left, a handsome study/office with a brick fireplace offers an intimate retreat for working. To your right, a formal dining room with garden views comfortably accommodates twelve. A discreet swing door leads to a well-appointed wet bar and large walk-in pantry, which then opens into the expansive kitchen. The kitchen is the true hub of the home, anchored by coffered ceilings, an oversized island, a full suite of high-end appliances, abundant cabinetry, and extensive counter space. A light-filled dinette offers the perfect spot for casual meals. At the center of the home, an oversized great room draws everyone together with its tall brick fireplace, built-in display/bookshelves, and high ceilings that add volume without sacrificing warmth. Two bedrooms are thoughtfully located on the main level, including the primary suite, privately positioned in one of the quietest corners of the home. Filled with soft natural light, accentuating the detailed millwork that runs from floor to ceiling. The primary bath is a retreat in itself, featuring slate flooring, double vanity, claw-foot soaking tub, water closet, walk-in shower with rain head, and a massive custom walk-in closet. The second main-level bedroom functions beautifully as a guest suite or flexible space, with an en-suite bath that also serves as a pool bath, a built-in Murphy bed with integrated cabinetry. A back facing staircase leads to two additional en-suite bedrooms on the second level. At the top of the landing, a large built-in workstation creates an ideal homework or creative zone, and both bedrooms enjoy access to a full-length front balcony. At the back of the home, a separate staircase leads to the fifth bedroom—a wonderfully private suite with dormer windows, angled ceilings with beams, and its own en-suite bath. In addition to a walk-in closet, cleverly designed built-in storage along the walls ensures a place for everything. Off the great room, a covered lanai with tongue-and-groove wood ceiling and brick built-in grilling station creates a comfortable space for year-round relaxation. A 45-foot lap pool is anchored by a striking cabana with fireplace, evoking a resort-inspired setting for long afternoons, evening gatherings, and memorable celebrations. This is a rare opportunity to own a thoughtfully crafted estate where history, craftsmanship, and everyday comfort come together in perfect balance.

1600 Legion Drive, Winter Park
1445 Via Sangro Place, Winter Park
$1,249,000
6 Beds ⋅ 6 Baths ⋅ Lakeside Estates SubDv. ⋅ 32792 Zip Code
Virtually Staged. Welcome to your dream estate inside the highly sought-after, gated enclave of Lakeside Estates in Winter Park! This magnificent 2-story residence, built by Meritage Homes, spans an impressive 5,021 square feet of luxurious living space and features a commanding tile roof. Boasting a versatile layout of 6 bedrooms, 5 full bathrooms, and 1 half bath, this home showcases 2 separate primary suites one on each level providing an ideal setup for multi-generational living or an expansive guest retreat. Step through the entrance to be captivated by soaring high ceilings, fresh custom interior paint, premium engineered hardwood and tile flooring, and an open-concept flow flooded with natural light. The chef-inspired gourmet kitchen is an entertainer's masterpiece, equipped with brand-new quartz countertops, high-end stainless steel appliances, a generous island, and a seamless connection to the family room and sunny kitchen nook. Upstairs, a versatile bonus loft opens up endless possibilities for a media room or play space, supported by 2 dedicated indoor laundry rooms for ultimate convenience. Step outside to your private backyard paradise, complete with a covered lanai and a fully screened-in, sparkling custom pool and spa. Complete with an immaculate 3-car garage featuring a fresh protective floor coating, this property delivers executive comfort with easy access to top-rated schools, boutique shopping, fine dining, and all the historic charm of Winter Park. Schedule your private tour today!

1445 Via Sangro Place, Winter Park
216 Lewfield Cir Unit 216, Winter Park
$230,000
3 Beds ⋅ 2 Baths ⋅ Stratford A Winter Park Condominium SubDv. ⋅ 32792 Zip Code
Rare Find - 3 BR/2 BA - 2nd Floor CONDO at The Stratford a Winter Park Condominium! Spacious Living Room accesses 2nd Floor Balcony with a gorgeous view of one (1) of the sparkling community pools. Balcony features additional outside storage room. Dining/Breakfast Nook adjacent to Living Room & Kitchen. Kitchen features refrigerator, electric range, dishwasher, microwave, garbage disposal, pantry, and laundry closet with stackable washer/dryer. Nice sized bedrooms, see attached floor plan. Primary Suite features walk in closet, walk in shower and tile flooring. Guest Bath features tub & shower and tile flooring. Unit conveniently located at back of community by both community pools and tennis courts. Lovely shady, treed community with sidewalks, Clubhouse, two (2) Pools, BBQ areas, and Tennis Court. HOA Fees Cover: trash removal, water, internet only, amenities maintenance, landscaping, and roof. Community Docs and 2026 Budget available for review. Conveniently located to shopping, parks, restaurants, and major transportation routes. Property sold "AS IS", it won't last long!

216 Lewfield Cir Unit 216, Winter Park
1399 Aloma Avenue, Winter Park
$575,000
3 Beds ⋅ 2 Baths ⋅ Galloway Place Rep SubDv. ⋅ 32789 Zip Code
Charming 1948 home with Winter Park Chain of Lakes access offers a great opportunity for buyers looking to renovate or explore new construction in an established Winter Park location. Conveniently located near Rollins College, Park Avenue, and Winter Park Hospital, with access to Lake Osceola just a short walk away to launch a paddleboard or canoe. The 3-bedroom, 2-bath character home offers a split floor plan with original hardwood floors, arched doorways, plantation shutters, and a formal living room with a gas fireplace and built-ins. The updated kitchen features Carrara quartz countertops, stainless appliances, and wood cabinetry, and opens to the dining and sunrooms. French doors from the sunroom lead to a covered patio and backyard with mature landscaping, paver walkways, and a tranquil cabana perfect for relaxing. Additional features include an attached one-car garage with washer/dryer, walk-in closets, and a circular driveway for additional parking. Improvements include new PEX water supply lines (2025) and partial drain-line replacement, recent interior painting, and updated bathrooms with a 2019 renovation featuring marble shower and floors. With its original character, thoughtful improvements, and convenient Winter Park location, this home offers an opportunity for its next owner to make it their own.

1399 Aloma Avenue, Winter Park
1407 Broad Wing Lane, Winter Park
$491,000
3 Beds ⋅ 3 Baths ⋅ Enclave At Hawks Crest SubDv. ⋅ 32792 Zip Code
Welcome to The Enclave at Hawks Crest! This 2019-built townhome offers 3 bedrooms, 2.5 baths, and 2,308 sqft of modern, open-concept living. The main level flows from the foyer into a bright living/dining area and an island kitchen with granite-look counters, subway tile backsplash, and a full stainless appliance suite. Wood-look vinyl plank flooring throughout the living areas; carpeted bedrooms upstairs including a primary suite with tray ceiling, dual vanity, and glass-door walk-in shower with large-format tile. A versatile loft adds flexible living space. Step out to the covered lanai with ceiling fan overlooking a wooded view. 2-car garage plus a laundry room with sink and cabinetry. Enjoy resort-style community amenities — clubhouse, pool, playground, and park — minutes from Winter Park shopping and dining. HOA $333/mo. Call and schedule your showing today!

1407 Broad Wing Lane, Winter Park
700 Melrose Avenue Unit M23, Winter Park
$354,000
2 Beds ⋅ 2 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code
Virtually Staged. Winter Park living, with a view you’ll actually want to come home to! This spacious 2-bedroom, 2-bath condo at Winter Park Gardens is clean and puts you in the middle of it all while giving you a peaceful place to escape. Set on the second floor with elevator access, the home overlooks the community pool and lush mature gardens, giving the living spaces a beautiful green backdrop. Step inside, to your open living area, flooded with natural light. The Florida room adds an extra spot to relax with a good book, work from home, or enjoy your morning coffee, with updated windows bringing in plenty of natural light while helping to keep cooling costs low. Fresh interior paint gives the home a clean, updated feel and an easy canvas for your own style. Just outside your door, Winter Park Gardens offers beautifully landscaped grounds, a community pool, pond, and lighted walking paths. Then there's the location. Walk or bike ride to Park Avenue's restaurants, shopping, and boutiques, the Winter Park Tennis Center, Rollins College, and Mead Botanical Garden. This is a great opportunity to enjoy the lock and go Winter Park lifestyle without giving up space, convenience, or a little peace and quiet. Call to schedule your showing today!

700 Melrose Avenue Unit M23, Winter Park
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