Winter Park Homes with Sidewalks Community Features

Winter Park Homes with Sidewalks Community Features

Welcome to Winter Park, Florida – a picturesque city that perfectly blends small-town charm with modern amenities. Nestled just a stone’s throw away from downtown Orlando, Winter Park is renowned for its stunning tree-lined streets, vibrant arts scene, and a rich history that dates back to the late 1800s. With its enchanting parks, beautiful lakes, and a plethora of shopping and dining options, this community offers a lifestyle that is as inviting as it is diverse.

One of the standout features of Winter Park is its commitment to creating a walkable environment. Homes with sidewalks are prevalent throughout the community, encouraging residents to explore their surroundings on foot. Imagine strolling along the scenic paths, greeting neighbors, and enjoying the fresh air as you make your way to the local coffee shop or park. The sidewalks not only enhance the aesthetic appeal of the neighborhood but also foster a sense of community, making it easy to connect with friends and family.

In addition to its charming streets, Winter Park boasts an array of cultural attractions, including the renowned Charles Hosmer Morse Museum of American Art, the beautiful botanical gardens at Mead Botanical Garden, and the lively Winter Park Farmers’ Market. Families will appreciate the excellent schools and recreational facilities, while nature enthusiasts can take advantage of the nearby lakes for boating and fishing.

Whether you’re seeking a cozy bungalow or a spacious family home, Winter Park’s homes with sidewalks provide the perfect backdrop for a vibrant and fulfilling lifestyle. Come and discover the magic of Winter Park – where community, culture, and comfort come together in perfect harmony.

Newest Winter Park Homes with Sidewalks Community Features

6 Beds ⋅ 5 Baths ⋅ O6440381 MLS

Welcome to luxury living in Hawks Crest, Winter Park’s only guard-gated community. This exceptional six-bedroom Del Rio floor plan sits on one of the neighborhood’s most coveted premium lots, featuring a larger lot line, wooded HOA land behind the property, and serene views toward Lake Howell. The thoughtfully designed floor plan offers two primary suites, one on each level, plus a dedicated office, a theater room, a loft, and a three-car tandem garage with built-in shelving and a workbench. Designer finishes include Restoration Hardware and Pottery Barn chandeliers, plantation shutters, crown molding, motorized blinds, app-controlled LED trim lighting, and custom built-ins throughout the home. The resort-style backyard features a saltwater, solar-heated pool, expansive pool deck, motorized Sunpro awnings, landscape lighting, and lanai market lights—perfect for entertaining or relaxing in complete privacy. Additional upgrades include a custom entertainment center with an electric fireplace, a Sony theater system and projector in the media room, a water softener, gutters, and extensive custom storage solutions by Inspired Closets throughout the home. The hot tub, Paradise Grill, and custom workout equipment are also available for negotiation, offering the opportunity to make this already exceptional home truly turnkey for your lifestyle. Hawks Crest residents enjoy an impressive collection of community amenities, including a resort-style pool, splash pad, clubhouse, fitness center, playground, putting green, and a private dock on Lake Howell. With highly regarded private schools nearby—including Park Maitland School, The Geneva School, Trinity Preparatory School, and The Master’s Academy—along with the exceptional shopping and dining of Park Avenue, this coveted Winter Park location truly offers the best of convenience, lifestyle, and luxury. Every box has been checked. From the premium homesite to the designer finishes, custom upgrades, resort-style pool, and thoughtful details throughout, this is a home where everything has already been done—just move in and enjoy.

1257 Wading Waters Circle, Winter Park

2 Beds ⋅ 2 Baths ⋅ O6439897 MLS ⋅ C BLDG.

This is exactly what you are looking for! Adorable 2/2 close to Full Sail and UCF. Tons of shopping and restaurants and convenient to the 417 and the 408. Location makes this perfect for a primary residence or investment property. Split floor plan ideal for roommates. Walk to Full Sail. 15 minutes to downtown Orlando and approximately 30 minutes to most attractions. Exceptionally well taken care of and only needs your personal touches to make it a really cute home. Seller will offer an appliance package and a 1 year home warranty with the right contract. What are you waiting for come and get it!!

3651 N Goldenrod Road Unit C109, Winter Park

3 Beds ⋅ 3 Baths ⋅ O6440236 MLS ⋅ X BLDG.

Hawk's Crest is a care free resort style master planned community in Winter Park, Florida. With it's Modern style architecture, this 3 bedroom, 2 1/2 bathroom townhome is meticulously maintained with an HOA that covers more than most. While driving through the community you will pass the community pool and recreation area which is conveniently nestled at the end of Bantam Way. The curb appeal of the paver driveway and home design will make you feel you are home. Inside you will be greeted by a foyer before entering the home itself. On the main floor you will find a half bathroom/ guest bathroom, tile flooring throughout, excellent natural light, living room, dinette, and the statement kitchen sure to please. The kitchen boast granite counter tops, shaker style cabinets, a extra large kitchen island with a breakfast bar, ample size walk-in pantry, refrigerator 2026, all other appliances 2021, new and upgraded kitchen hardware, newer faucet, and newer large single basin sink. Upstairs you will find all the bedrooms, inside laundry room and both full bathrooms, The primary suite is an ample 20 x 15 with trey ceiling, en-suite bathroom, and walk in closet with a custom closet organizer. The en-suite bathroom is highlighted by a dual vanity sink, granite countertops, shaker style cabinets, and shower stall. Both additional bedrooms are an impressive 15 x 12 with walk in closets. The inside laundry room has upgraded cabinets. Out back you will find a quiet covered rear patio with space for seating, a grill, and more. Other highlights to mention include the tesla electric charger in the garage and freshly added cabinets and granite countertops in the drop zone just off the inside garage entrance. Community common areas include a resort style pool with covered social gathering area and a community playground. The HOA covers the cable, internet, community pool, exterior building maintenance, common area maintenance and more. Hawk's Crest is just minutes to Park Avenue Winter Park, 417, UCF, shopping, restaurants and much more. Just a short walk to the out-parcel building in the front of the community you will find local favorites like Foxtail coffee, Kelly's Ice cream, and the Park Maitland School. Don't miss this opportunity. These townhomes go quickly.

1521 Bantam Way, Winter Park

3 Beds ⋅ 4 Baths ⋅ O6438596 MLS ⋅ Versailles Of Winter Park BLDG.

Welcome to The Versailles of Winter Park, an extraordinary opportunity to own one of only seven exclusive private residences in one of Winter Park's most coveted luxury communities, nestled just steps from the world-renowned Park Avenue and adjacent to the prestigious Alfond Inn & Spa. This magnificent third-floor residence offers 3,110 square feet of impeccably designed one-level living, oak hardwood floors throughout, elegant crown molding, and an abundance of natural light pouring through French doors set the tone for refined sophistication. Entertain effortlessly in the grand living area with a sprawling balcony adorned with Chicago brick and stone railing. Kitchen includes wood cabinet, granite, Monogram refrigerator, convection oven and microwave. The versatile split-bedroom floor plan ensures ultimate privacy, with the lavish primary suite accessed through double doors, walk-in closet, private balcony access, and an opulent spa bath featuring dual vanities, a soaking tub, walk-in shower. A designated office with wall-to-wall built-ins, a formal dining room accommodating up to twelve guests, a private two-car garage, and meticulously maintained landscaping. The Versailles of Winter Park is the ultimate expression of luxury living offering an unparalleled lifestyle just moments from the finest dining, boutique shopping, art festivals, and cultural events that makes Winter Park one of Florida's most desirable destinations.

200 S Interlachen Avenue Unit 350, Winter Park

2 Beds ⋅ 2 Baths ⋅ O6439854 MLS ⋅ F BLDG.

Virtually Staged. Updated two-bedroom, two-bath residence offering 908 square feet and a first-floor, pool-facing location in Mead Garden Condominium. The move-in-ready interior features luxury vinyl plank flooring throughout the living areas and bedrooms, tile flooring in the baths and defined living and dining spaces. The kitchen is appointed with white transitional cabinetry, granite countertops, a white subway tile backsplash and stainless steel appliances, including a refrigerator, range, microwave and dishwasher. A pass-through to the dining area incorporates built-in cabinetry, glass-front display storage and additional counter space. The dining area flows into the living room, where sliding glass doors open to an enclosed sunroom overlooking the community pool and landscaped grounds. The primary bedroom features natural light from a pool-facing window, built-in closet storage and an en-suite bath with a walk-in shower and white tile surround. A second bedroom provides flexible space for a variety of uses, while the second full bath offers a tub and shower combination. Additional features include a newer water heater, updated plumbing fixtures and convenient access to the community laundry room just outside the residence. From 1250 South Denning Drive, Residence 127 offers proximity to Mead Botanical Garden, Rollins College, Park Avenue, Azalea Park, Seven Oaks Park and Winter Park dining and retail.

1250 S Denning Drive Unit 127, Winter Park

3 Beds ⋅ 3 Baths ⋅ O6439222 MLS

Welcome to the Enclave at Hawks Crest, where this modern 3-bedroom, 2.5-bath townhome gives you 1,755 square feet of space without a long list of things to maintain. A paver driveway, two-car garage, and clean exterior make a great first impression, and inside, high ceilings and plenty of natural light keep the main level feeling open and bright. The kitchen sits right in the middle of it all with a large island, stainless steel appliances, and a walk-in pantry, opening naturally to the dining and living areas. Out back, sliding doors lead to a covered, screened patio overlooking greenspace, giving you a little breathing room without a backyard to take care of. Upstairs, the primary suite is spacious with a tray ceiling, large walk-in closet, and ensuite bath with dual sinks and a tiled shower. Two additional bedrooms sit at the opposite end of the hall, along with a second full bath and, thankfully, the laundry room is upstairs too. This home has been meticulously maintained by its original owner since 2021. The HOA handles the exterior and landscaping, and the gated community includes a resort-style pool, playground, and dog park. Zoned for A-rated Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High, and you're just minutes from Park Avenue, with Kelly's Ice Cream and Foxtail Coffee a short walk from your front door. Low maintenance, high convenience, and Winter Park right outside your door. Call today for your private showing!

2349 Shadowland Loop, Winter Park

2 Beds ⋅ 1 Baths ⋅ G5117377 MLS ⋅ Village Condominiums Of Winter BLDG.

Virtually Staged. **Rare opportunity to own in the highly desired Downtown of Winter Park for under $350,000!** Enjoy the highly desired downtown Winter Park lifestyle with Park Avenue’s boutiques, restaurants, cafés, arts and culture, Rollins College, the Winter Park Train station, Casa Feliz, seasonal festivals and community events all just a short walk from your front door. This charming 2-bedroom, 1-bath condo offers an inviting open-concept living and dining area, along with a kitchen featuring granite countertops and convenient counter seating. Condo is highlighted with beautiful plantation shutters. Located within a charming, intimate condominium community, it offers a wonderful combination of comfort, location and low-maintenance living, all within an area known for its highly regarded Winter Park-area schools. Whether you’re searching for a primary residence, a second home, a great option for downsizing, or an investment property, this is your opportunity to own a piece of one of Central Florida’s most desirable cities. Imagine strolling to dinner on Park Avenue, meeting friends for coffee, walking to Rollins College, enjoying the beauty and history of Casa Feliz, browsing the shops, attending an art festival or catching the train — all without worrying about finding a parking space. Simply walk out your front door and enjoy the incredible lifestyle that makes Winter Park such a special place to call home. **Opportunities to own downtown Winter Park real estate at this price point are rare. Don’t miss your chance — schedule your private showing today before this one is sold. A location and lifestyle like this won’t last long!**

500 N Pennsylvania Avenue Unit G, Winter Park

3 Beds ⋅ 3 Baths ⋅ S5156844 MLS ⋅ 7506 BLDG.

Beautiful, move in ready townhouse located in the highly desirable area of Winter Park. This well-maintained home provides confort, convenience and a versatile layout perfect for modern living. Featuring a spacious 2 car garage and a flexible 4th room on the first floor, ideal for a home an office, guest bedroom or additional living space. Enjoy being just minutes from shopping, dining and everyday essentials, all while living in a quiet and attractive community. This home is the perfect blend of style, functionality and location. Ready for its next owner.

7506 Cranes Creek Court Unit 30, Winter Park

4 Beds ⋅ 3 Baths ⋅ O6437839 MLS

A truly special property in Winter Park’s 32789 zip code, this renovated 1925 Craftsman is filled with character and charm. Set on an oversized 0.36-acre lot just one home from Lake Killarney, the property is 2803sf, with a 3/2 main residence (approximately 2200sf) plus a detached 1/1 guest cottage (approximately 600sf). Beautiful curb appeal and a glass-enclosed front porch with beadboard ceiling welcome you into the home. The original piano, which has been in the house since it was built, adds to its rich history and charm. Great layout for entertaining, with multiple sitting areas and an open floor plan with a dining room that flows to the family room and kitchen, all flooded with natural light and numerous windows and French doors. The kitchen offers bar seating, granite countertops, custom cabinetry and storage, stainless steel appliances, a natural-gas cooktop, glass tile backsplash, and tall ceilings. Glass French doors open to a brick patio and a walkway leading to the guest cottage. The two back bedrooms share a Jack-and-Jill bathroom, and the front bedroom with an adjacent hall bath connects to the enclosed sunroom, perfect for a nursery, office, or den. Additional details include original oak floors, crown molding, glass doorknobs, designer lighting, interior laundry with a new washer and dryer, and an upgraded security system. The expansive backyard features mature landscaping and ample space for outdoor enjoyment, with potential for a future pool. The metal-roofed carport includes a ceiling fan and string lights, and Lake Killarney is visible from several areas of the property. The guest cottage includes one bedroom, one bathroom, a living room, and a full kitchen—ideal for guests, extended family, a home office, or as a potential income-producing property. Recent improvements include the main-house roof in 2020; guest-cottage roof in 2022; two new guest-cottage A/C units installed in March 2023; security system in 2023; PVC water line and irrigation pump in 2024; main-house washer and dryer in June 2026; and exterior paint in August 2026. Additional updates include kitchen appliances, lighting and hardware, landscaping and irrigation system with well, interior paint, and a transferable termite bond. Conveniently located within easy walking distance of Hillstone, Trader Joe’s, numerous shops and restaurants, and quick access to I-4. All room dimensions, home & guest cottage square footage, and land square footage are approximate. Buyer to verify.

443 Broadview Avenue, Winter Park

3 Beds ⋅ 3 Baths ⋅ O6436269 MLS ⋅ 7530 BLDG.

Welcome home to this inviting 3-bedroom, 2.5-bath townhome offering a comfortable floor plan and several recent updates. All three bedrooms are conveniently located on the second floor and feature newly installed carpet, providing a fresh and comfortable feel. The main living areas feature easy-care ceramic tile throughout the living room and dining room, as well as in the bathrooms. The kitchen is equipped with new appliances, including a range/oven, dishwasher and microwave, making it ready for its next owner. An interior laundry area conveniently located near the kitchen helps make everyday chores a little easier. The interior has also been recently painted, giving the home a clean, refreshed appearance. Sliding glass doors from the dining room lead directly to the patio, providing a great spot for morning coffee, outdoor dining or simply enjoying some fresh Florida air. An attached one-car garage provides the added convenience of covered parking and additional storage. With new carpet, fresh interior paint, new kitchen appliances and a functional 3-bedroom layout, this townhome is ready for you to make it your own. Schedule your showing today!

7530 Cranes Creek Court, Winter Park

6 Beds ⋅ 6 Baths ⋅ O6433883 MLS

Virtually Staged. Welcome to your dream home in the highly sought-after Lakeside Estates neighborhood in Winter Park! This elegant 6-bedroom, 5-bathroom, 2 laundry rooms residence offers a perfect blend of modern comfort and timeless sophistication for the whole family. From the moment you enter, you will be captivated by the open concept design, high ceilings, an abundance of natural light. The gourmet kitchen features new quartz countertops, stainless steel appliances, and a spacious island that opens to the family and kitchen nook rooms for entertaining. New paint throughout. New garage coating on the floor. There are 2 primary suites, one on each level, that offers a peaceful retreat with a spa-inspired bath and walk in closets. After a long day, step outside to your private oasis complete with a covered lanai and fully screened-in sparkling pool and spa for hosting gatherings. With its beautifully design and prime location, this home is situated in a gated community, with easy access to top rated schools, boutique shopping, restaurants, and all the charm of Winter Park. Ready to call home!!

1445 Via Sangro Place, Winter Park

2 Beds ⋅ 1 Baths ⋅ O6437574 MLS ⋅ Lake Killarney Condominiums BLDG.

Virtually Staged. Experience lakefront living at its finest in this exceptional Winter Park Condominium Community overlooking beautiful Lake Killarney. Hidden gem complete with access to a community dock, private boat ramp, and a fenced lakeside pool perfect for relaxing and entertaining. Ideally located just minutes from the heart of Winter Park, this home offers unparalleled walkability. Stroll to Park Avenue's renowned boutiques, restaurants, and nightlife, catch a movie at Regal Cinemas, or conveniently shop at Publix and Trader Joe's. With countless restaurants, bars, and everyday amenities just steps away, you'll enjoy the perfect blend of tranquil waterfront living and vibrant urban convenience. Whether you're boating on the lake, lounging by the pool, or taking in the spectacular evening sunsets, this is a rare opportunity to enjoy one of Winter Park's most desirable waterfront lifestyles.

151 N Orlando Avenue Unit 242, Winter Park

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