Winter Garden/Oakland Homes with Sidewalk Exterior Features

Winter Garden/Oakland Homes with Sidewalk Exterior Features

Welcome to Winter Garden and Oakland, two charming communities nestled in the heart of Central Florida, where picturesque landscapes meet vibrant suburban living. Known for their rich history, these towns offer a delightful blend of small-town charm and modern conveniences. With its lush greenery and scenic lakes, Winter Garden is a haven for outdoor enthusiasts, providing ample opportunities for hiking, biking, and enjoying the great Florida weather. The historic downtown district is a treasure trove of unique shops, delightful eateries, and community events that bring neighbors together.

Just a stone’s throw away, Oakland complements Winter Garden with its serene atmosphere and close-knit community feel. This quaint town is perfect for those seeking a quieter lifestyle while still being within easy reach of the amenities and attractions of the larger city. The area is known for its commitment to preserving nature, with beautiful parks and trails that invite residents to explore the outdoors.

One of the standout features of homes in Winter Garden and Oakland is their inviting sidewalk exteriors. These beautifully designed homes often come with well-maintained sidewalks that encourage leisurely strolls through the neighborhood. Whether you’re taking a morning walk, enjoying an evening jog, or simply connecting with neighbors, the sidewalks enhance the sense of community and make it easy to enjoy the picturesque surroundings.

In Winter Garden and Oakland, you’ll find a diverse selection of homes that cater to various lifestyles, all while fostering a welcoming environment perfect for families, retirees, and everyone in between. Discover your dream home in this idyllic region today!

Newest Winter Garden/Oakland Homes with Sidewalk Exterior Features

$455,000
3 Beds ⋅ 3 Baths ⋅ Osprey Ranch Ph 1 SubDv. ⋅ 34787 Zip Code
Discover an inviting 3-bedroom, 2.5-bath home in Winter Garden, offering a comfortable layout designed for both everyday living and entertaining. The main living areas create an open and welcoming environment, with natural light enhancing the sense of space and connecting the living, dining, and kitchen areas. Upstairs, the bedrooms are thoughtfully separated from the main gathering spaces, providing added privacy and a comfortable retreat at the end of the day. The primary suite offers its own private bath, while the additional bedrooms provide flexibility for family, guests, a home office, or whatever best fits your lifestyle. Beyond the home itself, the location puts you close to everything that makes the Winter Garden area so desirable. Enjoy convenient access to shopping, restaurants, schools, recreation, and major roadways, making it easy to explore Horizon West, greater Orlando, and the many attractions Central Florida has to offer. Whether you're searching for your next home or an investment opportunity in a growing area, this property delivers a combination of location, functionality, and Florida living that is hard to overlook. Schedule your private showing and come see the possibilities for yourself.

15038 Windflower Alley, Winter Garden
$629,000
4 Beds ⋅ 4 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
Welcome to this beautiful 2024 Taylor Morrison home in Harvest at Ovation. Offering 4 bedrooms, 3.5 bathrooms, and 2,332 square feet, this residence features a bright open-concept layout and modern finishes throughout. A standout feature is the covered front porch overlooking a beautiful community green space, with no residence directly in front, providing an open view and added privacy. The kitchen offers quartz countertops, a large island, and contemporary cabinetry. A first-floor bedroom with a full bathroom provides flexible space for guests or a home office. Additional highlights include a covered lanai, laundry room, natural gas, and a two-car garage. Residents enjoy a community pool with cabana, butterfly garden, nature play space, dog park, and walking trails. Conveniently located near shopping, dining, SR 429, and Central Florida attractions. The area also features the newly opened Ovation Elementary and the recently built Water Spring Middle campus. Buyers should independently verify school zoning.

15154 Alder Chase Alley, Winter Garden
$663,065
4 Beds ⋅ 4 Baths ⋅ Osprey Ranch SubDv. ⋅ 34787 Zip Code
Under Construction. .

12331 Silk Mimosa Alley, Winter Garden
$580,000
4 Beds ⋅ 2 Baths ⋅ Covington Park A B D E F G & J SubDv. ⋅ 34787 Zip Code
Welcome to 618 Bainbridge Loop, where thoughtful updates, flexible living space, and the Winter Garden lifestyle come together. This 4-bedroom, 2-bath home PLUS a dedicated office features a desirable split-bedroom floor plan, while maintaining an open-concept layout that’s perfect for entertaining and everyday living. The renovated kitchen serves as the heart of the home, while the updated guest bathroom and renovated patio add even more move-in-ready appeal. The office features brand-new flooring, creating the perfect space for working from home, a playroom, or additional flex space. Major updates have already been taken care of with a 2023 roof, 2022 A/C, 2025 water heater, and 2024 appliances. Step outside to the refreshed patio, ready for morning coffee, weekend gatherings, or unwinding at the end of the day. Located within the Winter Garden golf cart district and near highly regarded local schools, this home offers a location that’s just as appealing as the home itself. With its combination of updates, functional layout, and sought-after Winter Garden lifestyle, 618 Bainbridge Loop is ready to welcome you home.

618 Bainbridge Loop, Winter Garden
$369,500
3 Beds ⋅ 3 Baths ⋅ Stoneybrook West Unit 8 SubDv. ⋅ 34787 Zip Code
Welcome to Westbrook at Stoneybrook West, a well-established townhome community in the heart of Winter Garden! This spacious 3-bedroom, 2.5-bath townhome offers 1,650 square feet of comfortable living space along with an attached 2-car garage. The main level features an open living and dining area, while all three bedrooms are conveniently located upstairs, including a spacious primary suite with a private bath and walk-in closet. A covered outdoor patio provides additional space to relax and enjoy the Florida weather. The home is currently being refreshed with new interior paint and new flooring throughout, allowing the next owner to move in and enjoy a clean, updated space from day one. Westbrook offers residents a community pool, playground, sidewalks, and plenty of guest parking, all in a location that puts everyday conveniences close by. Publix, Walgreens, restaurants, and shopping are just minutes away, with Winter Garden Village and Historic Downtown Winter Garden also within easy reach. Spend the weekend exploring the brick-lined streets of Plant Street, visiting the Saturday Farmers Market, or enjoying miles of biking and walking along the West Orange Trail. With convenient access to SR-429, SR-50, and Florida’s Turnpike, commuting throughout Central Florida, Downtown Orlando, the airport, and the theme parks is a breeze. Enjoy low-maintenance townhome living in one of Winter Garden’s most convenient locations — schedule your private showing today!

1327 Priory Circle Unit 1327, Winter Garden
$419,999
3 Beds ⋅ 3 Baths ⋅ Storey Grove SubDv. ⋅ 34787 Zip Code
Storey Grove ** 2023 built ** Open floorplan **BACKS TO GREENSPACE!!** Beautiful wood ceramic tile entire 1st floor ** Attractive tv wall wood accent inlay in the family room ** White kitchen cabinetry with quartz counters and large cooking island ** All bedrooms are on the 2nd floor ** Nice size +/-16x20 brick paver patio area and 2 car detached garage ** Great RING security system, RING cameras, doorbell and door and window sensors ** Tesla EV power outlet is already in place in the garage ** Overhead storage racks in the garage are included ** Storey Grove community amenities include a huge resort style community pool, fitness center, basketball courts, children's playground and green space area. Room measurements are from builder floor plan. Buyers to verify all room measurements.

10648 Words Drive, Winter Garden
$560,000
4 Beds ⋅ 4 Baths ⋅ Storey Grove Ph 1b-3 SubDv. ⋅ 34787 Zip Code
This beautiful 4 bedroom, 3 1/2 bath home features an open layout with designer finishes that are light and bright throughout. There are 2 master bedroom one on the first floor and in the second floor Perfect for families. Large great room downstairs, bonus room/loft upstairs with vaulted ceiling and a beautiful backyard. Upgraded just like the model. Quartz counter top throughout, upgraded light cabinets, wood plank, tile floor. Upgraded GE Profile appliances and complete Smart Home Package with smart thermostats, smart switches Wireless range extenders built in Alexa smart home controls. Storey Grove is beautiful picturesque community with pool, fitness center, parks, playgrounds and more. It's a perfect location just minutes from Disney, Shopping, Dining, New Hamlin retail and theaters, Easy Access to 429 Expressway, and zoned for A rated schools . Come and check personally .

15163 Book Club Road, Winter Garden
$450,000
3 Beds ⋅ 2 Baths ⋅ Corsino Place SubDv. ⋅ 34787 Zip Code
Set on a quiet cul-de-sac near the heart of Winter Garden, this updated single-story home pairs an easy, open layout with an unusually spacious backyard. Inside, 3 bedrooms and 2 bathrooms are arranged across 1,307 square feet, with vaulted ceilings and ceramic tile connecting the kitchen, dining area, and living room. The refreshed kitchen features white cabinetry, quartz countertops, a glossy subway-style backsplash, a deep undermount sink with a pull-down faucet, modern lighting, and a peninsula with breakfast-bar seating. Sliding glass doors extend the living space directly to the backyard. The primary suite offers tile flooring, a feature wall, private patio access, an en-suite bath, and a true walk-in closet. Two additional bedrooms and a second full bath provide flexible space for guests, an office, or everyday living. Fresh interior paint, updated light fixtures, ceiling fans, and a functional split-bedroom design complete the interior. Outside, the fully fenced 0.23-acre lot is a standout. A roofed pergola creates a generous shaded patio and room for outdoor dining and lounging. Beyond it, the broad lawn leads to a defined circular firepit area and a 10-by-20 storage shed, with ample open space for recreation, gardening, and outdoor hobbies. Aerial views highlight the depth and usability of the yard, while the attached two-car garage adds everyday storage and convenience. With no HOA and no CDD, the property offers flexibility in an established neighborhood close to the West Orange Trail, local parks, Lake Apopka, and the shops, dining, Plant Street Market, and brewery district of downtown Winter Garden. Enjoy an evening downtown, a weekend bike ride, or a relaxed night around the backyard firepit, all from a well-located home with room to make it your own.

1312 Corsino St, Winter Garden
$635,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this beautifully renovated golf-front home in the gated community of Stoneybrook West. Offering over 2,800 square feet of living space, this home combines a spacious and flexible floor plan with a fantastic setting overlooking the 6th hole and no rear neighbors. Recent improvements include a newer roof and A/C, fresh exterior and interior paint, renovated kitchen, bathrooms, and flooring. The main level offers multiple living and dining spaces, while the kitchen features stone countertops, stainless steel appliances and abundant cabinetry. Upstairs, the spacious primary suite includes a tray ceiling, walk-in closet and private bath with dual vanities and a beautifully remodeled walk-in shower. The oversized loft provides plenty of flexibility for a second living area, media room, playroom or home office. Step outside to a large backyard with expansive golf course views and plenty of room to enjoy the outdoor living. Stoneybrook West offers an impressive collection of amenities, including a community pool, golf, clubhouse, tennis and basketball courts, playgrounds and walking paths. Ideally located near Winter Garden Village, historic Downtown Winter Garden, shopping, dining and major roadways, this home offers a great combination of space, improvements, amenities and community.

15081 Masthead Landing Circle, Winter Garden
$464,990
3 Beds ⋅ 3 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code
Under Construction. Waterleigh presents the Sandhill. This spacious townhome features 3 bedrooms and 2.5 baths. As you enter the foyer you are welcomed with powder room, spacious kitchen with bar seating, dining area and a living room overlooking a covered patio. This popular townhome features a single car garage at the rear of the home. This community has upgraded stainless steel appliances and quartz countertops making cooking and cleaning a breeze. As we head upstairs, you are greeted with a loft area. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity. The second floor is complete with two guest bedrooms, an additional bathroom, along with laundry room. Like all homes in Waterleigh, the Sandhill includes a Smart home technology package which allows you to control your home with your smart device while near or away. Your new townhome will always have fantastic curb appeal while allowing you time to do the activities your family enjoys most. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

16534 Barbours Creek Way, Winter Garden
$199,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort SubDv. ⋅ 34787 Zip Code
Located on the second floor of Building 3, closest to the Safari Water Park, this fully furnished, two-bedroom, two-bathroom condo offers fantastic pond views and excellent proximity to resort amenities. This property is perfect for vacation home buyers seeking a true resort experience. Owners will enjoy resort-style living with access to multiple pools, a water park, a full-service spa, on-site restaurants, a state-of-the-art fitness center, and a large game room. For investors, this unit presents a compelling opportunity in Central Florida's booming tourism market. Located just minutes from Walt Disney World, Universal Studios, SeaWorld, upscale shopping, and diverse dining, this property promises strong rental potential and the flexibility to generate income while serving as a personal escape.

14501 Grove Resort Avenue Unit 3215, Winter Garden
$424,990
3 Beds ⋅ 3 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code
Under Construction. Waterleigh presents the Ibis. This spacious townhome features 3 bedrooms and 2.5 baths. As you enter the foyer you are welcomed with an open concept a spacious kitchen with bar seating, dining area and a living room overlooking a covered patio. This popular townhome features a single car garage and powder room at the rear of the home. This community has upgraded stainless steel appliances and quartz countertops making cooking and cleaning a breeze. As you head up to the second floor you are greeted with all 3 bedrooms and 2 bathrooms. The bedroom one suite impresses with double bowl vanity, walk in closet and spacious shower space. The second floor is complete with two guest bedrooms, an additional bathroom, along with laundry room. Like all homes in Waterleigh, the Ibis includes a Smart home technology package which allows you to control your home with your smart device while near or away. Your new townhome will always have fantastic curb appeal while allowing you time to do the activities your family enjoys most. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

16546 Barbours Creek Way, Winter Garden
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