Winter Garden Homes with Sidewalk Exterior Features

Winter Garden Homes with Sidewalk Exterior Features

Welcome to Winter Garden, a charming city located in the sunshine state of Florida. Known for its historic downtown, beautiful lakes, and family-friendly atmosphere, Winter Garden is a highly sought-after place to call home.

One of the standout features of homes in Winter Garden is the abundance of sidewalks. Perfect for morning strolls, jogging, or walking the dog, these sidewalks not only add to the aesthetic appeal of the neighborhood but also promote a healthy and active lifestyle for residents.

Whether you're looking for a cozy bungalow, a modern townhouse, or a spacious family home, Winter Garden offers a diverse range of real estate options to suit every taste and budget. Imagine coming home to a picturesque sidewalk-lined street, where neighbors wave hello and children play outside.

With top-rated schools, convenient shopping and dining options, and easy access to major highways, Winter Garden truly has it all. Experience the perfect blend of small-town charm and modern convenience in this thriving city.

Discover the magic of Winter Garden and find your dream home with sidewalk exterior features today!

Newest Winter Garden Homes with Sidewalk Exterior Features

no property photo
$640,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West 44/134 SubDv. ⋅ 34787 Zip Code
Enjoy the best of both worlds in this beautiful pool home overlooking the Stoneybrook West Golf Course, where peaceful surroundings, beautiful views, and an abundance of community amenities create the perfect lifestyle. With NO REAR NEIGHBORS and a location OVERLOOKING THE GOLF COURSE on quiet Portmoor Way, you can relax while having plenty of opportunities to stay active, socialize, and connect with neighbors. The curb appeal is welcoming as is the spacious foyer, tall ceilings, and WOOD FLOORS. The well-appointed kitchen features QUARTZ countertops, tile backsplash, stainless steel appliances, and a WALK-IN PANTRY. Enjoy the breakfast nook that opens to the family room, creating a comfortable gathering space with beautiful views of the SCREENED-IN POOL and golf course. The spacious primary suite is conveniently located downstairs and offers a large walk-in closet, an updated vanity with double sinks, a garden tub, separate shower, and linen closet. Upstairs, you'll find AIRY LOFT, laundry room with cabinet storage, three additional bedrooms, and a hall bathroom with double sinks. Additional interior highlights include a formal dining room, a PRIVATE OFFICE with stylish barn doors, and an attractive staircase with iron railing and an accent wall. The home also offers valuable updates, including a NEW ROOF (2022), AC (2019), upgraded light fixtures, tile flooring in the garage, and rain gutters. One of the greatest benefits of living in Stoneybrook West is the incredible lifestyle included with your HOA! SPECTRUM CABLE AND INTERET ARE INCLUDED IN THE HOA DUES. Spend sunny afternoons at the Olympic-sized COMMUNITY POOL and splash pad, meet neighbors at the clubhouse and FITNESS CENTER, or enjoy friendly competition on the BASKETBALL, PICKELBALL, VOLLEYBALL and TENNIS courts. For those who love the water and outdoors, the community also offers a BOAT RAMP, limited BOAT STORAGE, and a FISHING pier. Stoneybrook West is conveniently located near highly regarded schools, restaurants, shopping, major roadways including the 429, Turnpike and 408, historic downtown Winter Garden, and Central Florida's world-famous theme parks.

1414 Portmoor Way, Winter Garden
239 Largovista Drive, Oakland
$670,000
4 Beds ⋅ 3 Baths ⋅ Johns Landing SubDv. ⋅ 34787 Zip Code
Welcome to this well-maintained home in the gated community of John's Landing! With 4 bedrooms, 2.5 baths, a spacious bonus broom, and a separate office that could be converted back to a bedroom, there's plenty of room to make this home fit your needs. The Kitchen features a cozy nook for everyday meals, while the enclosed patio- with its built-in bar and entertaining area- is ready for relaxing or gathering with family and friends.The roof and water heater are approximately 3 years old. Enjoy the space, flexibility, and community amenities John's Landing has to offer. Come see if this homies the right fit for you!

239 Largovista Drive, Oakland
no property photo
$355,000
3 Beds ⋅ 2 Baths ⋅ Daniels Crossing SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this beautifully updated 3-bedroom, 2-bathroom home in the desirable Daniels Crossing community of Winter Garden! Featuring a bright, open floor plan, fresh modern finishes, and a comfortable living and dining area, this home offers the perfect blend of style and functionality. Enjoy peaceful pond views from your backyard, creating a relaxing setting to unwind and enjoy Florida living. The split-bedroom layout provides added privacy, while the attached 2-car garage offers convenience and extra storage. Residents can also enjoy the community pool. Conveniently located near shopping, restaurants, major roadways, and the popular Winter Garden Village, this home offers both comfort and an excellent location. Don't miss the opportunity to make this home yours!

271 Daniels Pointe Drive, Winter Garden
704 Caterpillar Run, Winter Garden
$675,000
4 Beds ⋅ 3 Baths ⋅ Mcallister Lndg SubDv. ⋅ 34787 Zip Code
Don't miss this one-of-a-kind, move-in-ready corner home featuring 4 bedrooms, 3 full baths, a dedicated office, and a 3-car attached garage, all on one level! Built in 2019, this spacious 3,000+ sq. ft. home offers an open, functional floor plan with vinyl flooring throughout, ceramic tile in wet areas, window treatments that convey and high ceilings. The home features separate living and dining areas, a spacious family room, and an open kitchen with granite countertops, center island, stainless steel appliances, and built-in oven and cooktop. The primary suite offers a large walk-in closet, double vanity, walk-in shower, separate soaking tub, and sliding glass door access to the oversized screened lanai. Additional bedrooms include a convenient guest suite with private bath. Enjoy the extended, full-length screened lanai with two ceiling fans, perfect for relaxing or entertaining. The sellers have made numerous improvements, including gutters, exterior paint (2022), epoxy-coated garage floor, built-in workbench, wall storage systems, and four overhead storage racks. The outdoor space features paver walkways and grilling pad, artificial turf with stepping stones, and a variety of fruit trees, including avocado, papaya, grapefruit, orange, and key lime, along with raised garden beds and an underground irrigation system. A transferable termite bond adds peace of mind. This beautifully maintained home offers space, functionality, and numerous upgrades. Schedule your private showing today!

704 Caterpillar Run, Winter Garden
1388 Waverunner Lane, Winter Garden
$515,000
4 Beds ⋅ 3 Baths ⋅ Waterside On Johns Lake - Phase 2c SubDv. ⋅ 34787 Zip Code
1% INTEREST RATE BUYDOWN for the first year, or up to a $6,000 Lender Credit—available through our preferred lender! UPGRADED CORNER LOT HOME IN THE CHARMING WATERSIDE COMMUNITY! Built in 2021, this 4 bedroom, 3 bathroom home features a thoughtfully designed floor plan, spacious fenced-in outdoor patio and backyard, and upgrades throughout. You are greeted by a welcoming covered front porch, the perfect spot to enjoy your morning coffee. Stepping inside, the OPEN-CONCEPT living space features wood-look tile flooring which flows effortlessly into the dining room and kitchen, creating a comfortable gathering place for family time and entertaining. The dining room has an ADDED BUILT-IN BAR area with dual-zone wine fridge, evergreen fog cabinets, butcher block countertop, and stylish backsplash. The kitchen features beautiful Silestone QUARTZ COUNTERTOPS, clean white cabinetry, under-cabinet lighting, and stainless-steel appliances, including an upgraded dishwasher (2024). Accentuating the bright kitchen are updated black pendant lights and handles. A bedroom conveniently located downstairs features a tasteful SHIPLAP accent wall, and adds incredible flexibility, easily serving as a guest room, home office, or playroom. Upstairs, the spacious primary suite offers a huge CUSTOM WALK-IN CLOSET, while the primary bathroom features a double-sink vanity and large WALK-IN TILED SHOWER. There are two spacious guest bedrooms upstairs that share their own separate bathroom, with its own shiplap feature wall, double sink vanity, and separate wet area for maximum convenience. Throughout the home you'll find additional thoughtful upgrades, including built-in desk and cabinets in the upstairs landing area, 9-foot ceilings, and a beautiful wrought-iron stair railing. Situated on a CORNER LOT, the property features a large wrought iron FENCED-IN backyard with plenty of room to play, relax, or gather with friends. The large back paver patio has an added SHADE SAIL, allowing for year-round enjoyment in the wonderful Florida weather. Community of Waterside residents enjoy access to a community clubhouse, pool, fitness center, two playgrounds, park, and a dock on Johns Lake. With seasonal community events and monthly food truck nights, there are plenty of opportunities to get to know your neighbors and enjoy everything the community has to offer. Conveniently located near Downtown Winter Garden, Hamlin, and Walt Disney World, you'll be close to a fantastic selection of restaurants, shops, and entertainment, plus top-rated schools and hospitals. Easy access to FL-429 and the Florida Turnpike makes commuting and exploring Central Florida a breeze. Set up your private showing of this updated home today!

1388 Waverunner Lane, Winter Garden
12818 Sunset Walk, Winter Garden
$659,008
4 Beds ⋅ 3 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. New Construction by Toll Brothers in Winter Garden’s Horizon West! Estimated completion in early 2027. Don't miss the opportunity to show your clients this beautiful corner-unit townhome! A welcoming covered entry leads into a thoughtfully designed, spacious living area featuring a dedicated dining space, gourmet kitchen with breakfast bar, and inviting great room with access to a private courtyard, perfect for relaxing or entertaining. The spacious primary suite offers a generous walk-in closet and a private ensuite bathroom featuring dual vanities, a separate shower, and a private water closet. Experience the quality, style, and thoughtful design of Toll Brothers in one of Winter Garden's desirable locations!

12818 Sunset Walk, Winter Garden
17984 Adrift Road, Winter Garden
$899,000
5 Beds ⋅ 5 Baths ⋅ Waterleigh Ph 4b & 4c SubDv. ⋅ 34787 Zip Code
Virtually Staged. Stunning lake views set the tone for this upgraded 5-bedroom, 4.5-bath home in Waterleigh, one of Horizon West’s most sought-after communities. Offering 3,225 square feet of living space, this home goes well beyond the standard build. Upgraded cabinetry, countertops, appliances, and flooring create a refined, cohesive look, while custom office cabinetry delivers a polished, built-in workspace. Custom closets add smart, organized storage. Location makes it even better, with Water Spring Elementary and Water Spring Middle within walking distance. Waterleigh offers a resort-style lifestyle with two clubhouses, multiple pools, fitness centers, tennis, pickleball, beach volleyball, mini golf, dog parks, and walking trails. All of this comes with a lake view you’ll never get tired of. Schedule your private showing today.

17984 Adrift Road, Winter Garden
557 Lake Cove Pointe Circle, Winter Garden
$2,249,999
5 Beds ⋅ 5 Baths ⋅ Lake Cove Pointe Ph 02 SubDv. ⋅ 34787 Zip Code
Virtually Staged. Some homes are updated. Other are completely reimagined. Welcome to an extraordinary lakefront retreat in the highly sought-after golf cart district of historic Downtown Winter Garden where an extensive, designer-led transformation has brought fresh style, thoughtful functionality and an entirely new feel to this exceptional property. Offering 5 bedrooms, 4.5 bathrooms, a dedicated office, and a theater/loft area, this home delivers the space and flexibility to fit the way you live. The interior has been gutted and beautifully redesigned with light, bright airy living spaces and curated finishes that make an impression from the moment you walk through the door. The stunning kitchen is a true centerpiece: open, inviting and designed to bring everyone together, whether it's a relaxed weeknight dinner or a house full of guests. Beautifully renovated bathrooms carry the designer aesthetic throughout, creating a cohesive balance of comfort and sophistication. Every gathering space feels connected, yet the layout still provides plenty of places to find a little privacy. Two primary suites give this floor plan rare versatility for multigenerational living, visiting family or simply having room to spread out. The first-floor primary suite offers privacy and convenience, while the upstairs primary retreat features its own balcony overlooking the lake. Imagine starting the day with coffee and a waterfront views or watching the sunset from your private escape. the upstairs suite also has its own laundry and a separate custom laundry room with double washers and dryers keeps busy households running smoothly. Outside is where this home truly becomes a lifestyle. Your private waterfront setting features a swimming pool, poolside cabana, boathouse, dock and direct access to the lake. Spend your afternoons boating or fishing, host unforgettable gatherings by the pool and end the day relaxing by the water. Newly added electric service at the dock adds convenience for evenings spent enjoying the lakefront atmosphere. Whether you love being on the water or simply love looking out over it, the outdoor spaces invite you to slow down and enjoy where you live. There's room here for quiet mornings, lively weekends, and all the moments in between. The improvements extend well beyond the finishes. An upgraded 400-amp electrical service supports modern living, while the whole-home generator and solar panels offer added practicality and peace of mind. This thoughtful combination of beauty and meaningful infrastructure upgrades makes the renovation as functional as it is striking. And the location? It's one of Winter Garden's most loved. Hop in the golf cart and head downtown, then come home to your own peaceful lakefront haven. Few settings offer this kind of everyday convenience while still feeling like a private getaway. Extensively transformed, exceptionally located and ready for its next chapter, this is a rare chance to have the designer finished home you've been dreaming of without giving up the waterfront lifestyle that makes Winter Garden so special. From mornings on the balcony to evenings on the dock, every day here offers another reason to stay a little longer.

557 Lake Cove Pointe Circle, Winter Garden
17906 Hither Hills Circle, Winter Garden
$560,000
4 Beds ⋅ 4 Baths ⋅ Lake Apopka Sound SubDv. ⋅ 34787 Zip Code
3.99 ASSUMABLE MORTGAGE OPPORTUNITY! Built in 2022, this four-bedroom home in Lake Apopka Sound offers single-story living, a three-car garage, and an open layout perfect for entertaining. The spacious kitchen features an oversized island, granite countertops, stainless steel appliances, and ample storage overlooking the inviting great room. A split-bedroom design provides privacy, while the primary suite includes dual vanities, a soaking tub, separate shower, and walk-in closet. Enjoy nearby outdoor adventures at the West Orange Trail and Oakland Nature Preserve, plus dining, boutiques, Plant Street Market, and the Saturday farmers market in historic Downtown Winter Garden. Shopping at Winter Garden Village and access to Florida’s Turnpike, SR 429, and Highway 50 add everyday convenience. Schedule your private showing today! Mortgage assumption subject to lender approval, buyer qualification, and applicable loan terms.

17906 Hither Hills Circle, Winter Garden
373 Eron Way Unit 47, Winter Garden
$163,000
2 Beds ⋅ 2 Baths ⋅ Townhomes Winter Garden SubDv. ⋅ 34787 Zip Code
Charming single-story townhome in Townhomes of Winter Garden featuring 2 bedrooms and 2 full baths. Interior features low-maintenance laminate flooring throughout the main living areas and bedrooms, paired with an efficient open floor plan. Conveniently located just minutes from historic downtown Winter Garden, Plant Street dining, shopping, and major commuter routes including SR-429 and the Florida Turnpike. Easy to show—schedule through Showing Time today!

373 Eron Way Unit 47, Winter Garden
10503 Spring Arbor Lane, Winter Garden
$459,000
4 Beds ⋅ 3 Baths ⋅ Winding Bay Preserve SubDv. ⋅ 34787 Zip Code
INVESTOR ALERT! Currently tenant-occupied, this beautiful 4-bedroom, 3-bath townhome offers over 2,200 sq. ft. of thoughtfully designed living space in Horizon West’s Winding Bay Preserve. The open kitchen features 42-inch white cabinets, a walk-in pantry, and a large island overlooking the spacious dining and great room. French doors lead to a screened, fenced courtyard with access to the 2-car garage. A first-floor bedroom with peaceful conservation views and an adjacent full bathroom provides added flexibility. Upstairs, the spacious primary suite features a dual-sink vanity, walk-in shower, private water closet, and a generous walk-in closet with built-ins. Two additional bedrooms overlook the conservation area and share a full bathroom, while a versatile loft and conveniently located laundry room complete the second floor. Winding Bay Preserve offers a resort-style community pool, playground, and parks amid beautiful conservation surroundings. Conveniently located near shopping, dining, schools, and Central Florida’s world-renowned attractions. An excellent opportunity to add a tenant-occupied property to your investment portfolio! Contact us for lease details and showing availability.

10503 Spring Arbor Lane, Winter Garden
15823 Shorebird Lane, Winter Garden
$924,900
4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 5 SubDv. ⋅ 34787 Zip Code
Discover an exceptional opportunity to enjoy the Florida lifestyle in this beautiful Toll Brothers home in the sought-after Lakeshore Preserve community of Winter Garden. Offering 4 bedrooms, 4 full bathrooms, and 2,768 square feet, this thoughtfully designed residence combines elegant interior spaces with an outdoor living experience designed for entertaining. The heart of the home is its impressive kitchen, featuring an oversized 12-foot island, gas cooktop, convection oven, and stylish finishes. Multiple living spaces and abundant natural light create an inviting atmosphere throughout. The flexible floor plan includes a first-floor bedroom and full bathroom, additional upstairs bedrooms, a private junior suite, and a spacious primary retreat featuring tray ceilings, dual walk-in closets, two vanities, a soaking tub, and a separate walk-in shower. But the real highlight is outside. Enjoy your own private saltwater pool, beautifully appointed paver deck, and summer kitchen with natural gas. Whether hosting friends, enjoying a quiet afternoon by the pool, or making the most of Florida's beautiful weather, this outdoor space makes every day feel like a getaway. Lakeshore Preserve adds even more to the experience with its lakefront clubhouse, resort-style community pool, fitness center, barbecue area, and recreational amenities. Located in Winter Garden, this home offers an appealing combination of space, thoughtful design, outdoor entertaining, and community amenities. Come experience the home and the lifestyle for yourself.

15823 Shorebird Lane, Winter Garden
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