Winter Garden Homes with Sidewalks Community Features

Winter Garden Homes with Sidewalks Community Features

Welcome to Winter Garden, Florida – a charming city that beautifully blends the warmth of small-town living with the vibrancy of modern amenities. Nestled just a short drive from the bustling heart of Orlando, Winter Garden boasts a rich history, picturesque landscapes, and a welcoming community spirit. The historic downtown area is a delightful mix of quaint shops, delicious eateries, and local farmers' markets, all set against a backdrop of stunning oak trees and lush greenery.

One of the standout features of Winter Garden is its commitment to creating a community where families can thrive. Homes with sidewalks dot the neighborhoods, encouraging leisurely strolls and fostering a sense of connection among residents. Imagine walking your dog in the early morning light or enjoying an evening jog while greeting friendly neighbors along the way. The sidewalks not only enhance the aesthetic appeal of the area but also provide safe and accessible routes for families and children to explore their surroundings.

Outdoor enthusiasts will appreciate the abundance of parks and recreational facilities, including the scenic West Orange Trail, perfect for biking, running, or simply enjoying nature. With a variety of community events hosted throughout the year, such as seasonal festivals and outdoor concerts, Winter Garden is a place where you can truly feel at home.

Whether you’re searching for a cozy bungalow or a spacious family residence, Winter Garden’s homes with sidewalks offer an inviting atmosphere that encourages an active and connected lifestyle. Come discover the charm of Winter Garden, where community and comfort meet in perfect harmony!

Newest Winter Garden Homes with Sidewalks Community Features

14501 Grove Resort Avenue Unit 3618, Winter Garden
$430,000
3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code
WELCOME TO THE GROVE RESORT & WATERPARK, WINTER GARDENS, ORLANDO FLORIDA. THIS BEAUTIFUL FULLY FURNISHED SABLE DESIGN CONDO IS IN AN EXCELLENT LOCATION WITH GREAT VIEWS OF WATER PARK AND MUCH MORE. THIS BEAUTIFUL SABLE DESIGN CONDO IS ON THE 6TH FLOOR WITH 3 LUXURY BEDROOMS AND 3 GREAT BATHROOMS. AND GREAT VIEWS FROM SCREENED BALCONY. YOU CAN OWN THIS BEAUTIFUL VACATION CONDO AT THE GROVE RESORT THAT OFFERS PROFESSIONAL ON SITE PROPERTY MANAGEMENT SERVICES TO ALL OWNERS AND THEIR GUESTS. THE GROVE RESORT HAS MANY AMENITIES INCLUDING BUT NOT LIMITED TO A GREAT WATER PARK, LAZY RIVER, SWIMMING POOLS , WATER SLIDES, SPA, INDOOR & OUTDOOR DINING, FITNESS CENTER, LAKE AUSTION FOR FISHING AND PADDLE BOATING, SHOPPING AND MUCH MORE

14501 Grove Resort Avenue Unit 3618, Winter Garden
6123 Flowering Cherry Bend, Winter Garden
$844,073
6 Beds ⋅ 5 Baths ⋅ Avalon Woods SubDv. ⋅ 34787 Zip Code
Under Construction. Discover the Anna Maria with Bonus in Avalon Woods! This two-story home offers 6 bedrooms, 4 full bathrooms, 1 half bathroom, and approximately 3,412 square feet of living space. The main level features a spacious great room, dining area, kitchen, and a private primary suite with a walk-in closet and bath. Upstairs, enjoy a versatile bonus room and additional bedrooms and bathrooms. A two-car garage adds everyday convenience. Community amenities include a park, playground, and trails. Conveniently located near shopping, dining, and major roadways in Winter Garden. Pricing, features, and availability are subject to change; confirm details with the builder.

6123 Flowering Cherry Bend, Winter Garden
6129 Flowering Cherry Bend, Winter Garden
$748,018
4 Beds ⋅ 3 Baths ⋅ Avalon Woods SubDv. ⋅ 34787 Zip Code
Under Construction. Welcome to a home designed for easy everyday living in Avalon Woods. This single-story Anna Maria, Elevation B, offers four bedrooms and three full bathrooms across 2,235 heated square feet. A welcoming covered front porch leads into an open layout where the family room, dining area and Gourmet Kitchen bring everyone together. Prepare a favorite meal at the spacious kitchen island, with a built-in oven, cooktop and range hood close at hand, then settle in for a relaxed evening with room to spread out. The primary suite offers a quiet retreat with a spa-style shower, while three additional bedrooms provide flexibility for guests, work or hobbies. Laminate flooring adds warmth to the main living areas, with carpeted bedrooms and tile in the bathrooms. Open the sliding glass doors to the covered rear lanai and enjoy a morning coffee or an unhurried weekend. A dedicated indoor laundry room and attached two-car garage add everyday convenience. Discover the comfort and possibilities of Avalon Woods in Winter Garden. Schedule a visit to the community model home. Sample Image.

6129 Flowering Cherry Bend, Winter Garden
8900 Sonoma Coast Drive, Winter Garden
$745,000
3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 3b 3c & 3d SubDv. ⋅ 34787 Zip Code
Enjoy resort-style living in Waterleigh, a master-planned community in Horizon West, Winter Garden. This single-story home offers 3 bedrooms, 2 full bathrooms, a half bathroom, and a separate office, complemented by distinctive interior finishes and expansive outdoor living spaces. An inviting foyer features decorative wood slat accents, integrated lighting, and a floating bench. The open-concept living area showcases a tray ceiling, wood-look tile flooring, and a custom TV feature wall with a floating media console. The kitchen features cabinetry, stone countertops, a tile backsplash, pendant lighting, and a stainless steel appliance package, including a refrigerator, built-in oven, microwave, cooktop, and dishwasher. A separate dining area provides additional gathering space. The office features glass French doors, built-in cabinetry, shelving, and work surfaces. The primary suite includes custom closet organizers and an en-suite bathroom with dual sinks, illuminated mirrors, a separate shower, a soaking tub, and a private water closet. The laundry room includes a washer and dryer, while the garage offers extensive storage cabinetry and a coated floor. Step outside to a covered, screened lanai overlooking an expansive paver patio with a fire pit, fenced backyard, and wooded backdrop—an inviting setting for relaxing or entertaining. Waterleigh offers community pools, clubhouses, fitness facilities, playgrounds, and recreational amenities in a scenic setting of lakes and ponds. Enjoy convenient access to shopping and dining at nearby Hamlin, Publix within the community, historic Downtown Winter Garden, and SR-429. Nearby schools include Atwater Bay Elementary, Water Spring Middle, and Horizon High School; buyers should verify current school assignments with Orange County Public Schools. Kitchen appliances, washer, and dryer are included in the sale. Furnishings shown in the photographs are actual furnishings. Select photographs have been digitally enhanced for lighting, and flames have been digitally added to the outdoor fire pit.

8900 Sonoma Coast Drive, Winter Garden
480 W Plant Street, Winter Garden
$785,000
2 Beds ⋅ 3 Baths ⋅ Park Place/Winter Garden SubDv. ⋅ 34787 Zip Code
In the heart of Historic Downtown Winter Garden, this three-story townhome in Park Place offers a rare blend of architectural character, flexible living spaces, and an exceptional walkable lifestyle. Step inside and discover this well-executed floor plan that lives much larger than its square footage suggests. Soaring 20-foot ceilings, expansive windows, open stair railings, and a custom loft create an impressive sense of space and natural light with an airy feel. The second-floor living area is the centerpiece anchoring the home, featuring custom German Schmear limewashed brick, detailed trim work, a built-in entertainment center, and sliding glass doors that open to a Juliet balcony overlooking downtown. The thoughtfully designed kitchen offers an oversized island with dine-in seating, white wood cabinetry with glass insets, stainless steel Samsung appliances, designer lighting, plantation shutters, and a convenient built-in workspace. Only two of these Park Place floor plans exist. One of the home's most unique features is the custom loft overlooking Plant Street and the West Orange Trail. Complete with a built-in ladder and bench seating, it's an inviting space to read, work, or simply enjoy the view. The first floor offers a private guest suite or study with an en-suite bath and walk-in closet. With special-use permits issued for select Park Place Plant St units, commercial zoning on this level lets you add a professional workspace. Upstairs, the third-floor owner's retreat provides privacy, a spacious walk-in closet, walk-in shower, and additional storage. Lovingly maintained by its original owner for seven years, this home offers low-maintenance, lock-and-leave living in one of Downtown Winter Garden's most desirable locations. The location is hard to beat. Step outside and you're in the heart of what makes Downtown Winter Garden special. Walk to the Saturday farmers market, enjoy the restaurants and shops along Plant Street, hop on the West Orange Trail, or meet friends for dinner without ever getting in your car. Rare in character, remarkable in design, and irreplaceable in location, 480 W. Plant Street is more than a beautiful home. It’s an invitation to fall in love with where you live.

480 W Plant Street, Winter Garden
Winter Garden
$530,000
3 Beds ⋅ 4 Baths ⋅ Parkview At Hamlin SubDv. ⋅ 34787 Zip Code
Welcome to modern Hamlin living in this beautiful END-UNIT townhome in highly desirable Winter Garden! Built in 2025 and offering 3 bedrooms, 3.5 bathrooms and over 2,000 square feet across three thoughtfully designed levels, this home combines the space and privacy of a single-family layout with the convenience of low-maintenance townhome living. One of the best features of this floor plan is that ALL THREE BEDROOMS ARE PRIVATE SUITES with their own bathrooms. The first-floor suite is ideal for guests, a home office, multigenerational living or anyone wanting additional separation and privacy. The second floor is the heart of the home, featuring a bright, open-concept kitchen, dining and living area with 42-inch cabinetry, white quartz countertops, stainless steel GE appliances and modern luxury vinyl plank flooring. Step outside to the covered lanai for an additional spot to relax or unwind. Upstairs, the spacious primary suite offers a private retreat along with the home's third bedroom suite. As an END UNIT, this home enjoys additional privacy with no neighbor on one side, plus added natural light. A two-car attached garage provides plenty of storage and everyday convenience, while the abundance of additional parking directly in front of the home makes hosting friends and family refreshingly easy. And then there's the LOCATION. Parkview at Hamlin puts you in the middle of one of Winter Garden's most convenient and sought-after areas, surrounded by restaurants, shopping, groceries, entertainment and everyday essentials. With SR 429 just minutes away, commuting throughout Central Florida is a breeze while still enjoying everything the Hamlin and Horizon West area has to offer. Modern, spacious, exceptionally well located and barely a year old—this is the kind of rental that truly feels like home. Schedule your showing and come see what makes this end-unit Hamlin townhome stand out.

Winter Garden
5567 Cypress Hill Road, Winter Garden
$519,995
3 Beds ⋅ 2 Baths ⋅ Orchard Hills Ph 2 SubDv. ⋅ 34787 Zip Code
Stunning 3-bedroom, 2-bathroom home located in the beautiful and desirable Orchard Hills subdivision of Winter Garden, FL. This home boasts a split bedroom plan, offering privacy and space, with carpeted bedrooms for added comfort. The master suite features a garden tub, perfect for unwinding after a long day. The open floor-plan is ideal for entertaining, with wood look tiled living areas and modern fixtures adding a touch of elegance. The kitchen is equipped with stainless steel appliances, ready for your culinary adventures. The interior has been freshly painted, giving the home a clean and bright feel. Step outside to a manicured lawn and a fence enclosed backyard, perfect for outdoor activities. Not to mention lawn service is included in the rent! The screen enclosed rear patio is a great spot for relaxation, while the front porch offers a scenic pond view, adding to the home's charm. The property also includes a large interior laundry room and a two-car garage for your convenience. As part of a vibrant community, you'll have access to a community pool, fitness center, and clubhouse. This home is not just a place to live, but a lifestyle to enjoy. Come and experience the comfort and convenience this home has for you.

5567 Cypress Hill Road, Winter Garden
16549 Parable Way, Winter Garden
$545,000
4 Beds ⋅ 4 Baths ⋅ Storey Grove SubDv. ⋅ 34787 Zip Code
Virtually Staged. 2023 build new house! Highly desirable Storey Grove community! NO CDD.Low HOA fee! Beautifully maintained 4-bedroom, 3.5-bath home in the highly desirable Storey Grove community! Featuring a thoughtfully designed floor plan with TWO Primary suites—one conveniently located on the FIRST floor and the other upstairs—this home offers exceptional flexibility for multi-generational living, extended family, or hosting guests. The functional and versatile layout provides comfortable living spaces ideal for both everyday living and entertaining. Enjoy the convenience of living in a family-friendly community with a community swimming pool and the added benefit of having elementary and middle schools right within the neighborhood—making daily school commutes easier for busy families. one of Storey Grove's most attractive features is its convenient location near Walt Disney World, offering easy access to world-famous theme parks, shopping, dining, and entertainment. With convenient access to major highways and everyday essentials, this home combines a desirable location with comfortable Florida living. Easy Access to Major Highways, Shopping, Dining, and Entertainment Don't miss this wonderful opportunity to enjoy comfort, flexibility, and convenience in the sought-after Storey Grove community, just minutes from the magic of Disney!

16549 Parable Way, Winter Garden
14501 Grove Resort Avenue Unit 3239, Winter Garden
$165,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium SubDv. ⋅ 34787 Zip Code
***Amazing opportunity to own a vacation condo at the beautiful Grove Resort and Water Park in Orlando! Ideal for SNOWBIRDS, you can stay in your unit up to 179 nights per year! Onsite rental management company rents out your unit on your behalf when you are not using it, yet when you stay you have full access to all the wonderful amenities at The Grove Resort! This 2-bedroom, 2-bathroom fully-furnished condo has a full kitchen, full washer and dryer, spacious living room with sleeper sofa, and screened-in balcony, with a pleasant view over the gardens. A short walk takes you to the Springs Pools area, with three heated pools, hot tub, the 24/7 gym, and the Valencia Restaurant. Just a few minutes stroll also takes you to the Surfari Water Park, with heated large pool and lazy river, water slides, splash area, the Flowrider surfing experience, and the Longboard Bar and Grill!! For further entertainment you have the 6000sf Flip Flops games arcade, with 9-hole mini-golf! A free shuttle goes daily to the Disney these parks, right outside the Marketplace convenience store and gift shop! Call now for more details!!***

14501 Grove Resort Avenue Unit 3239, Winter Garden
14503 Avenue Of The Rushes, Winter Garden
$850,000
4 Beds ⋅ 4 Baths ⋅ Signature Lakes SubDv. ⋅ 34787 Zip Code
Pro Pics Coming Soon - 1st time on the market * Welcome to this beautiful and incredibly maintained home offering 4 bedrooms, 3.5 bathrooms, and approximately 3,315 square feet of living space in the desirable Signature Lakes community of Independence * Built in 2007, this spacious two-story home offers an inviting blend of comfort, style, and room to entertain * Attractive curb appeal, a welcoming covered entry, paver driveway, and tropical landscaping create a memorable first impression * Inside, the generous floor plan provides flexibility for everyday living, entertaining guests, and enjoying the Florida lifestyle * Step outside to the private screened pool area and create your own backyard retreat, perfect for relaxing and enjoying the sunshine year-round * Conveniently located near shopping, dining, major roadways, and the many amenities of Winter Garden, this property offers an excellent opportunity to enjoy the Central Florida lifestyle, with community recreation and outdoor activities. Community amenities include a clubhouse, 2 resort-style swimming pools, fitness facilities, tennis and basketball courts, playgrounds, parks, and community boat ramps and docks providing access to Lake Hancock.

14503 Avenue Of The Rushes, Winter Garden
13055 Sandcastle Drive, Winter Garden
$874,990
3 Beds ⋅ 4 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code
Step into the Renown, a new construction, single-story home situated within walking distance of the amenity center offering 3 spacious bedrooms, 3 beautifully appointed full bathrooms, a powder room, and an enclosed flex room. The open-concept layout seamlessly connects the gourmet kitchen, café, and gathering room, creating an airy atmosphere. The many windows and sliding glass door leading to the covered lanai bathe the entire space in natural light, elevating the overall feeling of openness. The heart of the home is the chef-inspired kitchen, where soft-close cabinetry with clear glass uppers meets luxurious quartz countertops and a decorative tile backsplash. Thoughtfully designed features like easy-reach corner cabinets, double roll-out trays, and a waste basket drawer make the kitchen as functional as it is beautiful. Whirlpool stainless steel appliances—including double ovens and a built-in natural gas cooktop—ensure you have everything you need for both everyday meals and special occasions. The kitchen flows effortlessly into the café and gathering room, where a sliding glass door leads to the covered lanai, making this home ideal for seamless indoor-outdoor living. Retreat to the luxurious owner’s suite, a serene sanctuary with two spacious walk-in closets and a spa-like en suite bathroom. Dual vanity sinks, a walk-in shower with a built-in bench and rain shower head, an enclosed toilet, and a linen closet complete the tranquil space. For added convenience, one of the walk-in closets connects to the laundry room which is outfitted with built-in cabinetry, a utility sink trimmed in quartz, and a storage closet. The two additional spare bedrooms, each with their own attached bathroom and walk-in closets, along with the open flex room and powder room, provide ample space for family and guests. Designer-curated finishes elevate every corner of this home, including pendant pre-wire and under cabinet lighting in the kitchen, matte black hardware and plumbing fixtures, and 8’ Cheyenne style interior doors. Enjoy the convenience of modern living with a smart thermostat and doorbell, and LED downlighting. Schedule a tour today!

13055 Sandcastle Drive, Winter Garden
14026 Frasier Street, Winter Garden
$464,900
3 Beds ⋅ 3 Baths ⋅ Highland Ridge SubDv. ⋅ 34787 Zip Code
SELLER OFFERING $10,000 TOWARDS BUYER CLOSING COST WITH AN ACCEPTABLE OFFER!! Welcome to this beautiful 2023-built home in the desirable Highland Ridge community of Winter Garden! Featuring 3 bedrooms, 2.5 bathrooms, and 1,985 square feet of thoughtfully designed living space, this home offers the perfect combination of modern comfort, functionality, and energy efficiency. Step inside and discover a bright, spacious open-concept main floor, ideal for everyday living and entertaining. The inviting covered front porch adds charm and provides a wonderful place to relax and enjoy the Florida lifestyle. Upstairs, you’ll find a versatile loft perfect for gathering and relaxation, along with a private primary suite offering comfort and privacy. The additional bedrooms provide flexibility for family members or guests. Built by Meritage Homes, known for its innovative energy-efficient features, this property is designed with comfort and potential energy savings in mind. Additional highlights include a two-car garage and access to the community pool. Location is another outstanding feature! Just a short walk from the new Ovation Elementary School and the Flamingo Crossings shopping center, offering a variety of restaurants, fast-casual dining options, grocery stores, a fitness center, and convenience stores, making everyday living exceptionally convenient. The property also provides easy access to major roadways and Orlando’s world-famous attractions. Don’t miss your chance to own a nearly new home in one of the Orlando area’s most desirable locations. Schedule your private showing today!

14026 Frasier Street, Winter Garden
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