Winter Park Homes with Sidewalk Exterior Features

Winter Park Homes with Sidewalk Exterior Features

Welcome to Winter Park, Florida – a picturesque city that perfectly blends charming small-town vibes with the vibrancy of contemporary living. Nestled just north of Orlando, Winter Park is renowned for its stunning landscapes, tree-lined streets, and a rich cultural scene that beckons residents and visitors alike. With its historic architecture and beautiful parks, this city offers a unique lifestyle that is both relaxed and invigorating.

One of the standout features of homes in Winter Park is their inviting sidewalk exterior. Imagine strolling along the sidewalks that weave through the neighborhood, where friendly neighbors greet you and children play nearby. These thoughtfully designed homes not only enhance the aesthetic appeal of the area but also foster a sense of community. The sidewalks provide a safe and pleasant way to explore the neighborhood, whether you’re heading to a local café, a nearby park, or one of the many cultural attractions, such as the renowned Charles Hosmer Morse Museum of American Art.

Winter Park’s real estate market is diverse, offering a range of homes that cater to various lifestyles and preferences. From charming bungalows to elegant estates, each property exudes warmth and character, making it easy to find your dream home. The combination of beautiful homes with sidewalk exteriors and the vibrant community spirit makes Winter Park a truly desirable place to live. Come experience the magic of Winter Park, where every stroll along the sidewalk reveals the beauty of this enchanting city!

Newest Winter Park Homes with Sidewalk Exterior Features

$254,000
2 Beds ⋅ 2 Baths ⋅ Cedarwood Village SubDv. ⋅ 32792 Zip Code
Virtually Staged. LIVE THE WINTER PARK LIFESTYLE! STYLE, SPACE & LOCATION—THIS ONE HAS IT ALL! Welcome to Cedarwood Village, where easy living meets one of Winter Park’s most desirable locations, just minutes from the charm, dining, shopping, and entertainment of Downtown Winter Park and Park Avenue. This beautifully maintained 2-bedroom, 2-bath residence with an enclosed bonus room offers a spacious, light-filled floor plan designed for both comfortable everyday living and entertaining. Vaulted ceilings enhance the open living and dining areas, while the generously sized kitchen features newer appliances, abundant cabinet and counter space, plus room for a cozy breakfast table. Retreat to the oversized primary suite, complete with two large closets and sliding glass doors opening to the bonus room. The renovated primary bath adds a touch of luxury with an updated vanity and impressive custom walk-in shower. The guest bedroom offers its own sliding glass doors leading to the front patio, creating a bright and inviting space for family or overnight guests. The updated guest bath adds convenience with a washer and dryer neatly tucked away in the closet. One of the home's best features is the enclosed bonus room, offering valuable additional living space that's perfect for a home office, den, reading retreat, hobby room, or simply a relaxing place to unwind. Enjoy the Florida lifestyle without leaving the neighborhood! Cedarwood Village offers a sparkling community pool, two tennis courts, and clubhouse for residents to enjoy. And then there’s the LOCATION! Shopping, restaurants, medical facilities, and everyday conveniences are all close by, with easy access to major roadways and the boutiques, sidewalk cafés, restaurants, parks, and unmistakable charm of Park Avenue and Downtown Winter Park just minutes away. More than a home—it’s a Winter Park lifestyle. Come see why Cedarwood Village is such a special place to call home!

2477 Tahoe Circle Unit 2477, Winter Park
$420,000
3 Beds ⋅ 2 Baths ⋅ Garden Grove SubDv. ⋅ 32792 Zip Code
Completely renovated 3bed/2bath, split floorplan, single family home in the heart of Winter Park. With brand new roof, updated kitchen and bath, brand new stainless steel appliances, new interior and exterior paint, new porcelain tiling in all wet areas, and new laminate flooring in all bedrooms. Other highlights include a brand new front storm door, tiled screened patio and garage floors, brand new vinyl sidings, and a spacious fenced backyard, suitable for gardening, family gatherings and entertainment. Schedule, and check out this beauty today!

5588 Garden Grove Circle, Winter Park
$419,900
3 Beds ⋅ 3 Baths ⋅ Enclave At Hawks Crest SubDv. ⋅ 32792 Zip Code
This exceptional 3-bedroom, 2.5-bathroom end unit townhome is in pristine, move-in ready condition, combining low-maintenance living with the privacy of an end unit and the convenience of an attached 2-car garage. At the heart of the home, the impressive kitchen comes fully outfitted with elegant granite countertops and a sleek suite of stainless steel appliances, offering a stylish, high-performing hub for daily cooking and entertaining. Designed with comfort and quiet transition in mind, soft carpets on the stairs and second floor bring warmth and noise reduction to the private upstairs sleeping quarters. Spotlessly prepared and meticulously maintained from top to bottom, this turnkey residence is completely ready for a stress-free transition into a comfortable lifestyle.

1427 Broad Wing Lane, Winter Park
$148,000
1 Beds ⋅ 1 Baths ⋅ Parkview Village SubDv. ⋅ 32792 Zip Code
Great location! Light and bright, MOVE -IN READY! 1 bedroom, 1 bathroom on the 2nd floor in Parkview Village Condo community. Spacious living area with vaulted ceiling that allows natural light throughout the day. Tile flooring throughout, laundry closet with washer and dryer! Screened patio with relaxing views of green space. The community is centrally located near Full Sail University, UCF, Rollins College, and Valencia College, and great restaurants near by. The community offers a pool, jacuzzi, clubhouse, Dog park, and open green space to enjoy. did I mention, IT'S CENTRALLY LOCATED AND MOVE IN READY?? You won't want to miss this great condo, schedule your showing today!

3014 Antique Oaks Circle Unit 120, Winter Park
$164,900
2 Beds ⋅ 2 Baths ⋅ Lancelot/Winter Park SubDv. ⋅ 32792 Zip Code
Perfect for Investor or Owner Occupied. Why pay rent when you can own. This beautifully maintained 2-bedroom, 2-bathroom first-floor unit boasts an open floor plan with the kitchen being open to the living room/dining area and features a breakfast bar. Includes a full suite of Whirlpool stainless steel appliances, including Refrigerator, Microwave, Flat top Range/oven, Dishwasher. Additionally a washer and Dryer in Laundry Closet. Community features a pool/clubhouse. Excellent school zone which includes desirable Winter Park School High School, Glenridge Middle School. An ideal location that makes a Great Rental Investment property or owner occupied. Location, Location, Location... with only a few minutes to downtown Orlando, UCF, Valencia, Full Sail, Rollins College, theme parks, beaches, airport, highways 417 & 408, entertainment, dining & shopping. Whether you're looking for a primary residence or a long-term investment opportunity, this property combines location, functionality, and value in one of Orlando's most connected areas. Call now for your private showing, will not last.

3651 N Goldenrod Road Unit A103, Winter Park
$415,000
3 Beds ⋅ 2 Baths ⋅ Autumn Glen Ph 3 SubDv. ⋅ 32792 Zip Code
Welcome to this inviting 3-bedroom, 2-bathroom pool home in the Autumn Glen neighborhood of Winter Park, offering over 1,100 square feet of comfortable living space. As you step through the front door, you are immediately greeted by the bright, open-concept design, with natural light flowing throughout the home and creating a warm and welcoming atmosphere. To your left, the kitchen takes center stage with beautiful marble countertops, stainless steel appliances, an abundance of cabinetry and storage, and a charming farmhouse sink. The kitchen seamlessly opens to the dining area and living room, creating one connected space that is perfect for entertaining, relaxing, and making memories. Just off the entryway to your right, French doors open to one of the bedrooms, currently being used as an office, offering flexibility for a home office, guest room, or additional space to fit your lifestyle. Continuing into the living room, you'll find the primary bedroom tucked just beyond, offering a comfortable retreat filled with natural light. The primary suite features a closet and a private bathroom complete with a walk-in shower and stylish gold accents throughout. From the living room, follow the hallway to the third bedroom, which features its own closet, with the guest bathroom conveniently located nearby for easy access from both the bedrooms and main living areas. As you make your way outside, the home truly comes to life with a fully fenced backyard designed for enjoying the Florida lifestyle. The pool and hot tub combination creates the perfect place to cool off, unwind, or entertain, while the spacious patio provides plenty of room for soaking up the sun, gathering with friends, or enjoying late-night fires under the stars. Whether you're enjoying your morning coffee in the bright kitchen, relaxing in the living room, or spending summer evenings by the pool, this home offers a comfortable and inviting space to create memories. Conveniently located near shopping, dining, major highways, and Seminole County schools, this home offers the perfect blend of comfort, lifestyle, and convenience in Winter Park.

1533 Springtime Loop, Winter Park
$3,500,000
5 Beds ⋅ 6 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32792 Zip Code
Under Construction. Situated on a prominent corner lot in one of Winter Park's most desirable neighborhoods, this exceptional new construction residence makes an unforgettable first impression with its commanding architecture, refined craftsmanship, and remarkable attention to detail. Every element of the home has been designed to deliver a level of luxury rarely found at this price point, creating a residence that is both visually striking and exceptionally functional. A dramatic entry sets the tone from the moment you step inside, where a custom paneled feature wall and ceiling with integrated lighting create an architectural statement. Beyond the foyer, the expansive great room unfolds beneath soaring ceilings, anchored by a stunning entertainment wall featuring custom millwork, integrated LED lighting, and a sleek electric fireplace that serves as the centerpiece of the home's main gathering space. Oversized glass doors invite natural light throughout while seamlessly connecting the interior to the outdoor living areas. Designed for both everyday living and effortless entertaining, the chef's kitchen is as beautiful as it is functional. Custom cabinetry provides an abundance of storage, complemented by quartz countertops, an oversized center island, and a complete suite of premium Thermador appliances, including a built-in coffee system and paneled refrigerator. Just beyond, a spacious walk-in pantry offers extensive additional cabinetry, generous prep space, and a second dishwasher, making hosting on any scale effortless. The first-floor primary suite offers a private retreat with direct access to the backyard and resort-style pool. Its spa-inspired bath features dual vanities, an expansive walk-in shower, and a freestanding soaking tub, while the extraordinary custom closet by Hommes Design elevates everyday living with integrated LED lighting, a center island, and meticulously designed storage. A second downstairs bedroom, a highly sought-after feature rarely found in Winter Park, provides exceptional flexibility for guests, extended family, or a private home office. Upstairs, a spacious bonus room creates an additional living space complete with its own custom entertainment center, integrated LED lighting, and electric fireplace. A second primary suite, two additional generously sized bedrooms, and a private balcony complete the upper level, offering an ideal layout for large families and guests alike. The outdoor living experience is equally impressive. A covered lanai with a full summer kitchen overlooks a striking L-shaped pool with a raised spillover spa, while the oversized backyard and expansive side yard provide an exceptional amount of green space. The home also features a dedicated pool bath for functionality. Located just minutes from Cady Way Park, the Winter Park YMCA, and the boutiques and restaurants of Park Avenue, this residence also benefits from one of Winter Park's fastest-transforming corridors, where significant investment and redevelopment continue to enhance the area's long-term appeal. Combining exceptional architecture, thoughtful design, and an outstanding package of upgrades, this is a rare opportunity to own one of the most impressive new homes available in Winter Park today.

1901 Loch Berry Road, Winter Park
$675,000
4 Beds ⋅ 3 Baths ⋅ Meadows At Hawks Crest SubDv. ⋅ 32792 Zip Code
Welcome to a premier opportunity in the the coveted Winter Park. This beautifully maintained 4-bedroom, 2.5-bathroom home is located in The Meadows – an alcove in the gated Hawks Crest community – and offers buyers a turn-key opportunity to crack into the Winter Park market. With 1,770 square feet of thoughtfully designed living space, this home strikes the perfect balance between functionality and flow, featuring a living/dining combination anchored by the kitchen in the heart of the home. The central dining configuration is equally suited for quiet evenings or effortless entertaining, while the living room offers versatility as a spacious indoor retreat, or an indoor-outdoor oasis, complimented by the glass sliders. Before entering the primary suite, find three secondary rooms - two guest bedrooms and an office - along with a full guest bathroom and a powder bath, making every day living hassle-free and providing ample privacy. In the primary en-suite, unwind and enjoy the pleasures of a spacious retreat featuring an over-sized walk-in shower. This home is only 4 years young, so newer appliances and core components provide peace of mind, and an upgraded Tesla level 2 charger makes it fully equipped to suit every homeowner's needs. This home is just a short walk to the community amenities which include a clubhouse, pool, fitness center, turf lawn with a putting green, playground, dog park, and a private community dock on to Lake Howell. The 24-hour gated community provides peace of mind, all within easy reach of A-rated Seminole County schools (Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High), major employment corridors, the Orlando International Airport, and everything that Orlando has to offer. This is the kind of opportunity that doesn't come along often. Contact us to schedule your private tour today!

1122 Wildmeadow Run, Winter Park
$354,999
3 Beds ⋅ 2 Baths ⋅ Fairview Heights Rep SubDv. ⋅ 32789 Zip Code
Opportunity awaits in this 3-bedroom, 2-bath concrete block home located in the established Fairview Heights area of Winter Park. Offering 1,344 square feet of living space on a 6,460-square-foot lot, this single-story residence features a functional floor plan with tile flooring throughout the main living and dining areas. A covered rear entry leads to a brick paver patio and a fully fenced backyard with mature trees, providing space for entertaining, pets, or outdoor enjoyment. According to the seller, the roof was replaced approximately 10 years ago and the HVAC system approximately 6 years ago. Buyers are encouraged to verify all information and permits. The property is currently tenant-occupied on a month-to-month lease and may be delivered vacant at closing with a minimum of 30 days' notice, or continue as an investment opportunity. No HOA. Conveniently located near shopping, dining, parks, major roadways.

310 Granada Drive, Winter Park
$229,900
3 Beds ⋅ 3 Baths ⋅ Hidden Oaks Condo Ph 01 SubDv. ⋅ 32792 Zip Code
Welcome To This Beautifully 3 Bedroom, 2.5 Bathroom Condominium Located in the Desirable Hidden Oaks Community. Offering Updated Living Space, This Home Combines Comfort, Style, and an Unbeatable Location. Step Inside to a Spacious and Inviting Family Room Featuring Beautiful Laminate Flooring, Abundant Natural Light, and an Open, Welcoming Atmosphere. The Updated Kitchen Is Sure to Impress with Quartz Countertops, Stainless Steel Appliances, and A Sliding Glass Door That Opens to a Private Patio—Perfect for Relaxing or Entertaining. Upstairs, You'll Find All Three Bedrooms and Two Full Bathrooms, including a Generously Sized Primary Suite with a Walk-In Closet and Large Front-Facing Windows That Fill the Room with Natural Light. Residents of Hidden Oaks Enjoy a Peaceful Setting with Access to a Community Swimming Pool, Assigned Parking, And Plenty of Guest Parking. Ideally Located Just Minutes from Major Highways 408 And 417, This Home Is Only 4 Minutes from Full Sail University, Minutes from the University of Central Florida (UCF), Downtown Orlando, and Conveniently Close to Valencia College, Rollins College, Winter Park Shopping and Dining, Restaurants, and Everyday Conveniences. The Property Is Also Zoned for Highly Desirable Winter Park Schools, Making It an Excellent Choice for Homeowners and Investors Alike. Don't Miss This Move-In-Ready Opportunity in One of the Area's Most Convenient Locations!

7413 Belle River Court Unit 3, Winter Park
$1,775,000
4 Beds ⋅ 5 Baths ⋅ Osceola Or Lakeview Deed SubDv. ⋅ 32789 Zip Code
Charming and Sophisticated, this single-story home combines the old with the new in such a seamless manner, you will walk through the etched glass front door and immediately have the desire to sit down with a glass of wine, listen the player piano, and you will never want to leave. Welcome to this Completely Renovated Custom Home in the highly coveted area of Winter Park, just a few blocks from Phelps Park, the YMCA, and a beautiful walk to the Park Avenue shops and restaurants. Walking up the paver drive, over the travertine front patio and stepping into this gorgeous home, you are greeted with the formal living room featuring a player piano, a beautiful marble wood burning fireplace, and hardwood floors that flow throughout the home. Turning to your right you will find 3 large bedrooms, 2 full bathrooms and 1 half bath. You will note one of these secondary bedrooms presents as an en-suite with a full bathroom. The other 2 bedrooms share a full bathroom, along with an auxiliary half bath. Moving forward through the living room you step into the stunning oversized dining room, complete with a wall-bar custom made in Italy along with a wine dispensing machine (picture the Wine Room) which conveys with the sale. From the dining room we step down into a chef's kitchen like no other. Stunning 42"white wood cabinets, quartz countertops, white subway tile backsplash, a 6-burner natural GAS RANGE, double oven, and the largest center island with a microwave and beverage cooler on either end. This magnificent kitchen opens up to a large family room with French doors, surround sound speakers and large sunlit windows. Walking through the family room you will find the primary suite tucked away in the back of the house for the ultimate private sanctuary. Along with the generously sized bedroom with French doors giving access to the backyard and pool, you will be in absolute awe of the incredible primary bathroom, featuring his and hers sinks, a standalone tub, and a double-sided walk-in shower with 2 showerheads and storage benches. The on-demand hot water heater servicing this bathroom means you will never run out of hot water! Oversized His and Hers closets are the proverbial icing on the cake to this primary retreat ("Hers" is the size of a bedroom!). Stepping outside to the cozy covered patio, you will be drawn to the heated, saltwater pool built new in 2023, along with a summer kitchen, electric fireplace, and outdoor TV entertainment, also featuring the cutest pool half bath (no more dripping wet indoor bathroom trips!). Complementing the pool area is a fully fenced backyard for the 2-legged and/or 4-legged kiddos, large privacy hedges, and NO REAR NEIGHBORS. This home comes complete with a whole house Sonos system and speakers playing music throughout the house, even on the back patio, along with a whole house security system including 2 cameras and a Ring doorbell through Vivint. The 2-car garage easily fits both of your vehicles and has amble overhead storage along with attic access. Freshly painted exterior in 2026! Roof is 2018, AC's are 2018, hot water heater is 2026, and an updated irrigation system supported by a private well. Zoned for the BEST SCHOOLS, you can walk to Lakemont Elementary! Middle school is Maitland Middle, and of course, Winter Park High School. Only one lucky family will be able to call this turn-key custom Winter Park home theirs. Make an appt today so that lucky family is yours!

890 N Phelps Avenue, Winter Park
$495,000
3 Beds ⋅ 2 Baths ⋅ Woodcrest Unit 5 SubDv. ⋅ 32792 Zip Code
Welcome to 5316 Halyard Court, a beautifully updated pool home nestled in the heart of Winter Park. This move-in-ready residence offers the perfect blend of modern finishes, comfortable living spaces, and an incredible backyard designed for enjoying the Florida lifestyle. From the moment you arrive, you'll appreciate the inviting curb appeal, updated front entry, and thoughtfully maintained interior. Inside, the home features an open and functional layout accented by luxury wood-look flooring throughout, neutral designer colors, crown molding, recessed lighting, and abundant natural light. The spacious living areas flow seamlessly together, creating an ideal setting for both everyday living and entertaining. The generously sized bedrooms provide flexibility for families, guests, or a home office, while the updated bathrooms offer clean, contemporary finishes. The primary suite serves as a comfortable retreat with its own private en-suite bath. Step outside to your own private oasis featuring a sparkling in-ground pool surrounded by an expansive travertine paver deck, a screened lanai perfect for year-round relaxation, and a fully fenced backyard shaded by mature trees. Whether you're hosting weekend barbecues, enjoying a quiet evening by the pool, or letting pets and family play, this outdoor space offers endless possibilities. Additional upgrades include owned solar panels for enhanced energy efficiency and long-term savings, an attached two-car garage, and a spacious lot that provides both privacy and room to enjoy the outdoors. Ideally located, this home is just minutes from Downtown Winter Park and the renowned Park Avenue shopping and dining district, Rollins College, Full Sail University, AdventHealth Winter Park, UCF, Valencia College, and numerous parks, golf courses, and recreational amenities. Convenient access to SR-417, SR-436, University Boulevard, and Aloma Avenue makes commuting throughout Central Florida simple and efficient. Combining an exceptional location with modern updates and resort-style outdoor living, 5316 Halyard Court is a rare opportunity you won't want to miss.

5316 Halyard Court, Winter Park
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