Winter Park Homes with Sidewalk Exterior Features

5 Beds ⋅ 4 Baths ⋅ Pelican Bay SubDv. ⋅ 32792 Zip Code

Awesome 5 bedroom 3.5 bathroom custom built home on gorgeous 1.2 acre WATERFRONT cul-de-sac lot in lovely Pelican Bay of Winter Park. A True Gem on the Lake on a private dead-end street! Step through the front door and into a welcoming foyer with beautiful wood floors and oversized living and family rooms featuring dual wood-burning fireplaces. 4 BRAND NEW CUSTOM BAY WINDOWS (NOV 2026) installed in living room. The gourmet kitchen features classic oak cabinetry and upgraded granite counters, as well as BRAND NEW STAINLESS STEEL SIDE BY SIDE REFRIGERATOR (NOV 2026). Kitchen bay windows overlook massive screened rear porch, screened pool oasis, and breathtaking backyard waterfront views of Lake Florence. Main bedroom is downstairs and features large ensuite bathroom with dual sinks, garden tub, and walk in shower. Additional 4 bedrooms and 2 full bathrooms as well as bonus room are located upstairs and enjoy wonderful lakefront views. BRAND NEW ROOF INSTALLED NOV 2021. This oversized lot contains a variety of wonderful fruit trees and edible plants located around the property including avocado, purple yam, lychee, chinese chives, jujube, apple cactus, persimmon, mango, and dragon eye. The lake frontage speaks for itself, but as you can imagine the sunsets are truly superb. The Winter Park location is one of the best, close to shopping, schools, major roads, international airport, and amazing restaurants. Bring your buyers so they can make this beautiful custom home their own.

1400 Pelican Bay Trail, Winter Park

$435,000

3 Beds ⋅ 3 Baths ⋅ Trinity Bay Ph 2 SubDv. ⋅ 32792 Zip Code

Welcome to 5415 N Lake Burkett Lane, a beautiful home located in the desirable Trinity Bay community of Winter Park, with a neighborhood boat slip, dock, and lake access! Offering 3 bedrooms, 2.5 bathrooms, and 2,027 square feet of thoughtfully designed living space, this home makes a lasting first impression with its soaring vaulted ceilings and inviting atmosphere. The open, well-designed floorplan creates a natural flow throughout the main living areas, making it perfect for both everyday living and entertaining. The downstairs features spacious living and dining areas, a convenient half bathroom, a dedicated laundry room, and direct access to the attached two-car garage. Upstairs, you'll find all three bedrooms, offering a comfortable separation between the main living spaces and private retreats. The layout provides a wonderful balance of functionality and comfort, with plenty of room to accommodate a variety of lifestyles. Step outside to enjoy the screened-in rear patio, the perfect spot to enjoy your morning coffee or unwind in the evenings while taking in the outdoors. Beyond the patio, you'll find a generously sized backyard with endless possibilities! Whether you envision creating your dream outdoor entertaining space, adding a garden, designing a play area, or simply enjoying the extra room to relax, this backyard is a blank canvas waiting for your personal touch. With its spacious layout, soaring ceilings, and fantastic potential, this Trinity Bay home is an opportunity you won't want to miss!

5415 N Lake Burkett Lane, Winter Park

700 Melrose Avenue Unit B23, Winter Park

$295,000

2 Beds ⋅ 2 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code

Enjoy beautiful pond and garden views from this tastefully updated two-bedroom, two-bath upstairs condominium in Winter Park Gardens. The kitchen features solid-surface countertops and wood cabinetry, while both bathrooms offer updated vanities and elegant finishes. Plantation shutters, laminate and tile flooring complement the inviting interior. A bright Florida room with floor-to-ceiling windows provides the perfect setting to relax and take in the breathtaking pond and garden views. The unit is also plumbed for convenient in-unit washer and dryer installation. Set on more than eight acres of lush, meticulously maintained grounds, Winter Park Gardens features landscaped gardens, a tranquil pond, and a community pool. Located next door to the Winter Park Tennis Center and within walking distance of Rollins College and Park Avenue, this beautifully maintained and managed community places you minutes from Winter Park’s finest restaurants, gardens, and parks.*Click on Virtual Tour for video overview of this exceptional community!

700 Melrose Avenue Unit B23, Winter Park

$650,000

3 Beds ⋅ 3 Baths ⋅ Park Shore SubDv. ⋅ 32789 Zip Code

Exceptional Winter Park Living! Discover this newer, two-story SMART corner townhome, ideally situated in a highly desirable Winter Park location. Showcasing attractive architectural details, a welcoming covered entry, and meticulously maintained tropical landscaping, this residence offers the perfect blend of modern sophistication, comfort, and convenience. Step inside to a spacious, light-filled open-concept living and dining area highlighted by soaring ceilings, attractive wood-look flooring, contemporary finishes, and an effortless transition into the stunning kitchen. Designed for both everyday living and entertaining, the kitchen showcases crisp white cabinetry, stainless steel appliances, an expansive quartz waterfall island with seating for four, designer pendant lighting, and sliding glass doors opening to the private courtyard. A versatile built-in serving area, ideal for a coffee bar or dry bar, adds both style and functionality. The inviting courtyard provides a seamless extension of the interior living space, creating an intimate setting for alfresco dining, entertaining, or simply unwinding. Accented by elegant travertine flooring, this charming outdoor retreat also offers covered access to the detached two-car garage. Upstairs, you will find three generously sized bedrooms, two tastefully updated baths, and a spacious laundry room. The serene primary suite offers a relaxing escape with sophisticated accent walls, oversized windows, and elegant trim details. The luxurious en-suite bath features dual vanities, sleek quartz countertops, modern lighting, and an oversized walk-in shower with a frameless glass enclosure and exquisite floor-to-ceiling tile. Two additional bedrooms are filled with natural light and offer flexible living arrangements, including the possibility of a home office or study. Connecting these bedrooms is a beautifully designed Jack-and-Jill bath featuring a double-sink vanity, quartz countertops, stylish lighting, and a tub/shower combination enhanced by floor-to-ceiling tile. Remote-controlled window shades throughout provide added privacy and convenience, while a central vacuum system offers another thoughtful feature. Completing the second floor is an oversized laundry room equipped with a full-size washer and dryer, extensive custom cabinetry, ample countertop space, and attractive wood-look flooring. Perfectly positioned near the exciting new Minnesota Row development, this residence enjoys convenient access to shopping, dining, and major roadways. Just minutes from the heart of downtown Winter Park and its renowned Park Avenue shopping district, residents can enjoy an exceptional selection of sidewalk cafés, fine dining, upscale boutiques, museums, and the picturesque beauty of Central Park. Combining sophisticated finishes, thoughtfully designed interiors, exceptional outdoor living, and the convenience of SMART home technology, this impressive corner townhome offers an outstanding opportunity to enjoy the very best of the Winter Park lifestyle. A must-see residence! Call today to schedule your private showing!

1261 Michigan Avenue, Winter Park

$5,950,000

5 Beds ⋅ 6 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code

Under Construction. Exceptional waterfront living meets European-inspired design in this new Vimaro Homes residence on Lake Sylvan. Positioned on an oversized Winter Park lot with 130 feet of water frontage, the home pairs timeless architecture, richly detailed interiors, and expansive outdoor living. Led by a husband-and-wife team originally from Europe, Vimaro Homes brings together her expertise in interior design and his in construction. Their hands-on approach brings a personal commitment to every selection and detail, prioritizing lasting quality, thoughtful design, and craftsmanship over the cost-driven formulas common in investment-built spec homes. A striking façade and tile roof establish an elegant arrival, complemented by a dual-entry driveway featuring a diamond-patterned composition of turf and concrete. An underground three-car garage preserves the architectural approach, while an elevator connects all three levels. Inside, a marble mosaic entry introduces intricate trim work and classic reeded crown molding, establishing the home’s enduring character. The spacious living room features a marble-wrapped fireplace, custom built-ins with LED up-lighting, and expansive sliding doors framing views of the pool and lake. The kitchen pairs marble countertops and custom inset cabinetry with Perrin & Rowe fixtures and Thermador appliances, including a paneled refrigerator. A substantial scullery with a prep kitchen and pantry supports entertaining, while the nearby dining room overlooks the water. The downstairs primary suite offers a private retreat with its own fireplace and an expansive, custom-fitted walk-in closet with a center island. The primary bath features Casablanca marble tile, dual vanities, Perrin & Rowe fixtures, and a spacious walk-in shower. Upstairs, four additional bedrooms each offer an ensuite bath and walk-in closet, alongside a bonus room, laundry room, and terrace. Throughout the home, natural stone, finely crafted cabinetry, and classic architectural details reflect the team’s European influences. Outdoors, a generous lanai with retractable screens and a full summer kitchen extends the living spaces toward Lake Sylvan. A three-tiered deck brings together a pool, spa, and sweeping water views, while expansive green space and a dock complete the waterfront setting. Set on a brick street moments from Park Avenue’s restaurants, boutiques, and cafés, this residence combines Winter Park’s distinctive character with an exceptional lakefront setting. Shaped by the personal vision and craftsmanship of Vimaro Homes, it offers a refined expression of waterfront living.

1441 Grove Terrace, Winter Park

4940 Tangerine Avenue Unit 4940, Winter Park

$249,000

3 Beds ⋅ 2 Baths ⋅ Wrenwood Condo SubDv. ⋅ 32792 Zip Code

Spacious living, valuable updates, and easy condo ownership come together at 4940 Tangerine Avenue in Winter Park’s established Wrenwood community! This generously sized three-bedroom condominium offers room to spread out, with flexible space for guests, a home office, or everyday living. Major improvements include a replaced air-conditioning and heating system, water heater, and electrical panel, adding comfort and value where it matters most. The community has also recently completed roof replacements on all buildings, all building where completely repainted and the driveway and parking throughout the condo complex have been completed—another standout benefit for your next home. Enjoy a refreshing swim in the community pool, gather with neighbors at the clubhouse, and spend more time enjoying life with the convenience of low-maintenance condominium living and affordable association fees. Conveniently located near shopping, dining, and major roadways, Wrenwood offers easy access to Winter Park’s many attractions and Park Ave. Whether you’re looking for a primary residence or a Florida getaway, this spacious three-bedroom condo deserves a place at the top of your list!

4940 Tangerine Avenue Unit 4940, Winter Park

$415,000

3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 8 SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully updated 3-bedroom, 2-bath home with a 2-car garage, nestled in the highly desirable Eastbrook neighborhood of Winter Park! Light, bright, and inviting, this home offers an abundance of natural light through its numerous windows, creating a warm and welcoming atmosphere throughout. The updated kitchen features crisp white cabinetry, beautiful quartz countertops, and stainless steel appliances. Luxury vinyl plank flooring extends throughout most of the home, offering both style and easy maintenance. Both bathrooms have been tastefully updated, adding to the home's fresh, modern appeal. Step outside to the screened and covered patio, the perfect spot for morning coffee, outdoor dining, or simply relaxing while overlooking the generously sized, fully fenced backyard. There's plenty of room to entertain, garden, or enjoy the Florida sunshine! Major improvements provide added peace of mind, including a new roof (2019), replumbing (2022), new HVAC system (2022), and new double-pane windows and sliding glass door (2023). Both the interior and exterior were freshly painted in 2023, completing the home's move-in-ready appeal. Ideally situated in the established Eastbrook community, this home offers the charm of Winter Park living with convenient access to shopping, dining, parks, and major roadways. With its thoughtful updates, inviting living spaces, and wonderful outdoor setting, this is a home you won't want to miss!

2038 Ponderosa Avenue, Winter Park

$550,000

3 Beds ⋅ 2 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code

Welcome to 257 Lincolnshire Road, a 3-bedroom, 2-bath home offering 1,610 square feet of living space in the established Winter Park Pines neighborhood. Situated at the end of a cul-de-sac street, this single-story home sits on an expansive 0.58-acre lot, providing an inviting setting with room to bring your vision to life. Inside, a spacious living and dining layout features multiple gathering areas, large windows that welcome natural light, and a distinctive brick fireplace with wood-paneled detailing. The kitchen offers generous cabinet storage, a breakfast bar, and an open connection to the main living area. An attached two-car garage adds everyday convenience. Sliding glass doors open to a covered, screened-in patio overlooking the oversized backyard. With over 200 feet of rear property line, this expansive outdoor space offers remarkable flexibility for entertaining, gardening, recreation, or designing your own outdoor retreat. Mature trees and natural greenery create a welcoming backdrop with plenty of room to enjoy. Whether you envision renovating and personalizing the existing home or starting fresh by removing the current structure and building a new residence, this expansive property offers the flexibility to explore a variety of possibilities. Enjoy the appeal of an established neighborhood with the golf course just down the street and convenient access to Aloma Avenue. With its generous lot, cul-de-sac setting, and Winter Park location, this property is ready for your ideas.

257 Lincolnshire Road, Winter Park

$450,000

5 Beds ⋅ 3 Baths ⋅ Eastbrook Sub Unit 05 SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully renovated pool home featuring a rare and versatile double primary suite layout! Completely renovated in 2024, this 5-bedroom, 3-bathroom home offers 1,636 square feet of stylish, thoughtfully designed living space with modern finishes throughout. Light gray wood-look plank tile flooring and recessed lighting create a bright, cohesive feel. The contemporary kitchen showcases gray shaker-style cabinetry, sleek black granite countertops, a marble-look tile backsplash with black mosaic accents, stainless steel appliances, and a breakfast bar with seating for four. The first primary suite is privately positioned away from the additional bedrooms and features an ensuite bathroom with a marble-look tiled shower, decorative mosaic accents, multiple shower heads including a rain shower, a frameless glass enclosure, and a gray vanity topped with black granite. The second primary suite provides added flexibility for multigenerational living, extended guests, or a private retreat. Step outside to enjoy your own backyard oasis, complete with an in-ground pool, screened lanai, and fully fenced, spacious backyard with plenty of green space for relaxing, entertaining, and outdoor activities. Ideally located approximately 10 minutes from the restaurants and boutiques of Park Avenue, with convenient access to UCF, Full Sail University, Rollins College, major transportation routes, shopping, and dining. Orlando International Airport is approximately 25 minutes away. With its modern renovations, dual primary suites, and inviting outdoor living space, this home offers a unique combination of comfort, flexibility, and convenience! ROOF - 2024 HVAC - 2025 PLUMBING - 2026 ELECTRICAL - 2024

1825 Chilean 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

$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

$375,000

3 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 1 SubDv. ⋅ 32792 Zip Code

Welcome to 1830 Gladiolas Drive, a beautiful 3 bedroom, 2 bathroom home in Winter Park’s Garden Lake Estates community. This move-in ready home features a 2023 AC, a 2022 water heater, a 2020 roof, and a brand new freshly painted interior. Inside, the spacious open living and kitchen area is the heart of the home. The thoughtful layout keeps everyone connected, whether you’re cooking, hosting friends, or settling in for a quiet evening. Natural flow between the spaces makes the home feel open and welcoming. The primary suite is a private retreat. It’s generously sized and has a large walk-in closet, so you have plenty of room for your wardrobe and a calm place to start and end your day. Outside, the expansive rear patio extends your living space into the Florida outdoors. It’s ready for morning coffee, weekend barbecues, or dinner under the stars. Beyond it, the big backyard gives you room to play, garden, or add the features you’ve been dreaming of. Functional, inviting, and close to everything in Winter Park, this home is ready for its next chapter with several major updates already completed. This home is a great opportunity for someone looking to add their own personal touch.

1830 Gladiolas Drive, Winter Park

Winter Park Homes with Sidewalk Exterior Features

Newest Winter Park Homes with Sidewalk Exterior Features

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