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 small-town warmth with modern conveniences. Nestled just a short drive from the vibrant attractions of Orlando, Winter Garden boasts a rich history, a thriving downtown area, and a community spirit that is palpable in every corner. With its picturesque landscapes and lush greenery, this city is a haven for those who appreciate nature and outdoor activities.

One of the standout features of homes in Winter Garden is the community-centric design, particularly the presence of homes with sidewalks. These inviting pathways not only enhance the aesthetic appeal of the neighborhoods but also encourage a friendly and active lifestyle. Imagine taking leisurely strolls with your family or enjoying a morning jog while greeting your neighbors along the way. Sidewalks foster a sense of connection and community, making it easy to explore the charming shops, delightful cafes, and local parks that Winter Garden has to offer.

In addition to its beautiful homes, Winter Garden is known for its commitment to preserving green spaces, with numerous parks and recreational areas perfect for picnicking, playing, or simply unwinding. The West Orange Trail runs through the city, providing miles of scenic pathways for walking, biking, and enjoying the great outdoors.

With a vibrant community atmosphere, excellent schools, and a variety of events throughout the year, Winter Garden is not just a place to live; it’s a place to thrive. Come discover the charm of Winter Garden, where your dream home awaits amidst a welcoming community!

Newest Winter Garden Homes with Sidewalks Community Features

3 Beds ⋅ 3 Baths ⋅ Stone Crk Un #4 SubDv. ⋅ 34787 Zip Code

Virtually Staged. Welcome to this charming two-story home in the desirable Stone Creek community of Winter Garden! All bedrooms are conveniently located upstairs, offering a functional split from the main living space below. The kitchen boasts stainless steel appliances and a breakfast bar that opens up to the dining area and living room, creating a bright, open-concept layout perfect for everyday living and entertaining. Ideally located near Johns Lake, with easy access to nearby shopping, dining, and parks including the West Orange Trail, this home offers the perfect blend of comfort and convenience in one of Winter Garden's sought-after communities. Don't miss this move-in ready opportunity!

2036 Portcastle Circle, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Sanctuary/Twin Waters SubDv. ⋅ 34787 Zip Code

Located in The Sanctuary at Twin Waters, and ideally positioned on the community’s largest homesite at the end of a quiet cul-de-sac with no rear neighbors and water views. A long driveway, three-car garage, an oversized, and a fully fenced backyard. Inside, the open-concept layout features 4 bedrooms and 3 full baths, with updated flooring throughout the main living areas and primary suite. The kitchen is complete with stainless steel appliances, an oversized island, quartz countertops, upgraded backsplash, and 42-inch cabinetry. The living room is complete with a stone electric fireplace and custom built-ins. Sliding glass doors open to a screened and covered lanai, creating an easy transition to outdoor living and entertaining. A whole-home solar system, FULLY PAID-OFF, adds energy efficiency, and eliminates the electricity bill. Residents of The Sanctuary at Twin Waters enjoy access to a community pool, playground, walking trails, and private pier. Just minutes from Winter Garden’s Historic Downtown, shopping, dining, Cinepolis Luxury Cinema, Horizon West, the West Orange Trail, major highways, and Orlando’s world-famous theme parks. Call today to schedule a private tour.

16668 Sanctuary Drive, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Signature Lakes Ph 02 A B H I J SubDv. ⋅ 34787 Zip Code

Welcome to 6158 Meriwether Crescent in Winter Garden! This spacious 4-bedroom home offers a flexible floor plan with plenty of room to spread out, plus a private screened-in pool that makes Florida living easy. The main living areas feature an open layout with wood and tile flooring, while the kitchen offers granite countertops, stainless steel appliances, ample cabinetry and breakfast-bar seating. Large windows throughout bring in plenty of natural light, and multiple living and dining spaces provide flexibility for everyday living, entertaining or working from home. Step outside to the screened pool and patio overlooking a peaceful green setting, creating a great place to relax or entertain year-round. A detached garage with a brick-paver driveway adds even more functionality, while the covered front porch and mature landscaping give the home welcoming curb appeal. The surrounding community offers beautiful green space, walking paths, ponds and a neighborhood gazebo just steps from the home. Conveniently located in Winter Garden with easy access to shopping, dining, schools and everything the area has to offer, this home combines space, privacy and outdoor living in a great location.

6158 Meriwether Crescent, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code

Welcome to this modern 3-bedroom, 2 and 1/2-bath residence, 1650 square feet located in McKinnon Square at Oakland Park, nestled within Winter Garden's coveted golf cart district. This Home has a nice welcoming front porch and showcases timeless architecture, upscale designer finishes. Step inside to discover soaring ceilings, beautiful luxury vinyl plank flooring throughout the main living areas. At the heart of the home on the 2nd Story, the gourmet chef's kitchen features custom cabinetry with upgraded hardware, quartz countertops, an oversized island, a gas cooktop, custom vent hood, built-in wall oven, decorative tile backsplash, and abundant storage. The open-concept design flows effortlessly into the spacious family room with a Balcony to have coffee in the morning or tea in the evening. Upstairs, an expansive loft offers nice living space. Cathedral ceilings, walk-in closet. One of Winter Garden's most desirable lifestyles. This award-winning, master-planned community of Oakland Park features tree-lined streets, scenic parks, resort-style pools, playgrounds, and miles of walking and biking trails, including direct access to the renowned West Orange Trail. Residents enjoy a true neighborhood atmosphere just a golf cart ride from Historic Downtown Winter Garden, where you'll find award-winning restaurants, boutique shopping, breweries, coffee shops, live entertainment, and the nationally recognized Winter Garden Farmers Market close to Winter Garden Village at Fowler Groves the outdoor Mall and the Orlando International Airport. With convenient access to Florida's Turnpike, SR-429, 408, to downtown Orlando, and Central Florida's world-famous attractions and Themed Parks, this exceptional residence offers the perfect blend of luxury, convenience, community, and lifestyle.

910 Trowman Aly, Winter Garden

2 Beds ⋅ 3 Baths ⋅ Signature Lakes Ph 02 A B H I J SubDv. ⋅ 34787 Zip Code

Well-maintained and thoughtfully updated, this New Independence townhome offers the perfect combination of style, comfort, and low-maintenance Florida living, all while located in a highly desirable community. Step inside to find updated flooring throughout, plantation shutters, and a bright, inviting layout designed for effortless everyday living. The renovated primary suite adds a modern, elevated touch, while the home’s thoughtful design provides the perfect setting for both relaxing and entertaining. Outside, discover a beautifully organized backyard oasis—a private space to enjoy your morning coffee, host friends, or simply take advantage of the Florida sunshine. And the lifestyle extends well beyond the property. New Independence offers an impressive collection of amenities, including two resident clubhouses, two resort-style pools with cabanas and grills, a whirlpool spa, two fitness centers, tennis and basketball courts, parks, playgrounds, and more than 6 miles of walking, running, and biking trails. Residents also have private lake access with boat ramps and on-lake ski ramps serving the lakes between Lake Hancock and Lake Speer. The community also features two dedicated dog parks, including separate areas for large and small dogs. Additionally, the HOA also includes basic high-speed internet and cable TV service, adding even more value to the community’s amenities package. Location is a major advantage; this home is only minutes from the popular Hamlin shopping and dining district, as well as the Winter Garden Village, downtown Winter Garden, and major roadways. Enjoy convenient access to some of the area’s best restaurants, shopping, and everyday necessities while still coming home to a peaceful, established community. Updated. Turnkey. Ideally located. And ready for its next owner.

5751 New Independence Parkway, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Summerlake Pd Phase 2a And 2b SubDv. ⋅ 34787 Zip Code

SUMMERLAKE | WINTER GARDEN | HORIZON WEST | MOVE-IN READY Beautifully maintained one-story 3-bedroom, 2-bath home in the highly desirable Summerlake community, ideally located just minutes from Hamlin Town Center. Enjoy convenient access to shopping, dining, entertainment, top-rated schools, and major highways. The bright open-concept floor plan seamlessly connects the living, dining, and kitchen areas, with large windows providing abundant natural light. The kitchen features ample cabinetry, modern appliances, a breakfast bar, and NEW DISHWASHER & MICROWAVE. The spacious primary suite offers a walk-in closet and private bath with dual sinks, soaking tub, and separate shower. Two additional bedrooms share a full bathroom. TILE FLOORING THROUGHOUT provides a clean, durable, and low-maintenance finish. ROOF REPLACED IN 2026 and INTERIOR & EXTERIOR PAINT COMPLETED IN 2026, offering valuable peace of mind to the new owner. The attached garage includes a SPLIT A/C UNIT, creating a flexible space for storage, hobbies, recreation, or other personal use. The covered SCREENED-IN LANAI is perfect for relaxing and enjoying the Florida lifestyle. Located JUST ONE BLOCK FROM THE COMMUNITY CLUBHOUSE, this home offers exceptional convenience to Summerlake’s resort-style amenities, including a community pool, fitness center, tennis courts, playgrounds, walking trails, and clubhouse. HOA INCLUDES LAWN CARE, providing added convenience and low-maintenance living. Prime location near Hamlin Town Center, DISNEY, Publix, Walmart, restaurants, cafés, boutique shopping, Cinépolis Luxury Cinemas, PopStroke, Urban Air, Adventure Park, SR-429, and nearby schools including Summerlake Elementary, Hamlin Middle, and Horizon High School. Move-in ready with a new roof, fresh 2026 interior/exterior paint, new kitchen appliances, tile flooring throughout, screened lanai, and an unbeatable Winter Garden location. Schedule your private showing today!

14931 Porter Rd, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Summerlake Pd Ph 2c 2d 2e SubDv. ⋅ 34787 Zip Code

LAKEFRONT LUXURY IN SUMMERLAKE! Stunning 4BR/3BA townhome with bonus room, open concept living, brand new roof, state of the art appliances & decorative lighting included! Enjoy breathtaking lake views, nightly Disney fireworks, and a private fenced brick paver courtyard perfect for morning coffee or relaxing. Spacious 2-car garage. Resort-style amenities include clubhouse, gym, pool, soccer field, walking trails & fishing dock. Minutes to Disney, Downtown Winter Garden & endless dining! A MUST-SEE! Buyer to verify room sizes and all measurements. Public records reflect 3BR/2BA; actual configuration is 4BR/3BA plus bonus room

8174 Bluejack Oak Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Orchard Hills Phase 2 SubDv. ⋅ 34787 Zip Code

Welcome to this bright and airy 4-bedroom, 2.5-bath home offering a comfortable and inviting layout. The spacious kitchen opens directly to the living room, creating a great flow for everyday living and entertaining, and features a large island with plenty of room for meal prep or gathering with family and friends. The open feel continues throughout the main living areas, with plenty of natural light adding to the welcoming atmosphere. The primary bedroom offers a private retreat with its own door leading to the balcony, providing a nice spot to step outside and enjoy the fresh air.

14354 Orchard Hills Boulevard, Winter Garden

4 Beds ⋅ 2 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code

Welcome to the highly sought-after Brentwood model in the guard-gated golf community of Stoneybrook West! This 4-bedroom home offers a flexible floor plan with the option to use the fourth bedroom as a private home office, making it ideal for today’s lifestyle. The spacious kitchen opens to the family room, creating a comfortable gathering space highlighted by a cozy gas fireplace. Recent updates include a NEW HVAC system (2026), water heater (2023), roof (2018), new garbage disposal, gutters, and more. The primary suite features beautiful bay windows and a large walk-in closet. Enjoy Florida living year-round from the added covered and screened patio with tile flooring overlooking the fenced backyard. Additional highlights include attic storage with plywood flooring, providing valuable extra storage space. Located in the desirable Stoneybrook West community, residents enjoy an impressive array of amenities, including golf, clubhouse, pools, fitness facilities, tennis, pickleball, playgrounds, walking trails, and more. The community also offers lake access and boating for residents, including a private community boat launch. All of this is located in Winter Garden, one of Central Florida’s most sought-after and vibrant markets, offering convenient access to shopping, dining, entertainment, top-rated schools, major roadways, and everything the area has to offer. A flexible floor plan, important major-system updates, outdoor living space, and an exceptional guard-gated community make this Brentwood model a home worth seeing!

1118 Maidenmoor Road, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Hamlin Meadows SubDv. ⋅ 34787 Zip Code

Virtually Staged. Under Construction. The Harbor floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath, alongside two additional bedrooms. Downstairs, the open-concept layout connects the great room to the dining area, making it perfect for entertaining or family gatherings. The covered lanai offers a cozy outdoor retreat, ideal for relaxing at the end of the day. Completing the home is a detached two-car garage, ensuring ample parking and storage. The Harbor floor plan offers modern living tailored to meet everyday needs with style and functionality. Sample Image

17732 Porter Road, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Hamlin Meadows SubDv. ⋅ 34787 Zip Code

Virtually Staged. Under Construction. The Porter floorplan is an inviting two-story townhome designed with thoughtful spaces throughout. Featuring three bedrooms and two full bathrooms, the layout offers a smooth flow between living spaces. The first floor boasts a bright great room that opens into the dining area and lanai, perfect for entertaining or relaxation. Upstairs, all three bedrooms are thoughtfully arranged alongside a versatile loft, providing additional living space or an ideal work-from-home area. With a two-car garage and laundry room conveniently located on the second floor, the Porter combines functionality with comfort, making it a standout home choice. Sample Image!!

17728 Porter Road, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Oakland Trls Ph 2 SubDv. ⋅ 34787 Zip Code

Location, location, location!! Incredible opportunity to own a popular Whitman II model in the desirable Oakland Trails community with direct walkable access to the West Orange Trail! Imagine walking or biking to dinner in downtown Winter Garden just minutes away! You're also just minutes from the Florida Turnpike and all the new shopping in Clermont, including Costco just down the road. The location of this home is incredible! From the moment you step through the glass-paneled front door, you are greeted by a bright and airy two story foyer featuring warm luxury vinyl flooring and a contemporary staircase accented with sleek, industrial cable railings. The main level effortlessly transitions into a sun-drenched living space, anchored by large sliding glass doors that open up to an outdoor patio and frame views of the surrounding neighborhood. A neutral color palette and recessed lighting throughout enhance the sophisticated, move-in-ready aesthetic of the home. At the heart of the home is a chef-inspired gourmet kitchen designed for effortless entertaining. The massive central island takes center stage, featuring gleaming white quartz countertops, a deep undermount sink, and comfortable breakfast bar seating for four beneath stylish pendant lighting. Striking dark espresso cabinetry provides an abundance of storage space and beautifully contrasts the modern herringbone tile backsplash. Equipped with premium stainless steel appliances—including a built-in wall oven and microwave combo, a cooktop, and a French-door refrigerator—this kitchen is as functional as it is beautiful, complete with a spacious walk-in pantry nearby. Opposite the main living area, a formal dining space is defined by its soaring high-volume ceiling and a dramatic, modern halo chandelier that casts a warm glow over your dinner parties. Upstairs you'll love the oversized loft area that's open to below - perfect for cozier gatherings with the family. The secondary bedrooms are generously sized and each have their own walk in closets. The primary suite features a grand entrance with french doors leading to the large bedroom with two massive walk in closets, a tray ceiling, and more french doors leading to the spa inspired primary bath. The upstairs laundry room is conveniently placed to complete the home. With major shopping, dining, and entertainment options located within 15 minutes of this community, you have no shortage of lifestyle at your fingertips! You can get to Disney parks in about 20-25 minutes! You're also zoned to A rated schools, and have a very popular charter school - Oakland Avenue Charter School just minutes away. Come tour this home today!

2273 Standing Rock Circle, Oakland

Start Your Search