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

$365,000
2 Beds ⋅ 3 Baths ⋅ Orchard A1-A26 B1 B2 C D1-D4 SubDv. ⋅ 34787 Zip Code
Welcome to this beautiful Winter Garden townhome located in a desirable gated community with a community pool. This bright 2-bedroom, 2.5-bath end-unit townhome features a dedicated office that could easily be converted into a third bedroom, offering added flexibility for guests or a home workspace. An upstairs loft provides additional living space, perfect for a second living area, media room, playroom, or flex space. Interior features include tile flooring, tray ceilings, granite countertops, stainless steel appliances, plantation shutters, and newer wood-look laminate flooring upstairs. A new energy-efficient A/C system with warranty provides added comfort, efficiency, and peace of mind, while the newer roof adds even more value. The townhome also features a two-car rear-entry garage and is ideally located close to top-rated schools, shopping, dining, and Central Florida's world-famous attractions. With its desirable Winter Garden location, gated setting, community amenities, and versatile floor plan, this townhome is a must-see!

13855 Golden Russet Drive, Winter Garden
$479,900
3 Beds ⋅ 2 Baths ⋅ Crown Point Spgs SubDv. ⋅ 34787 Zip Code
New photos coming soon. Seller offering up to $20,395 toward buyer closing costs, prepaid expenses, and/or an interest rate buydown. Conditions apply. Move-in ready 3-bedroom, 2-bath POOL home in Winter Garden's established Crown Point Springs community with the big-ticket items already handled: new HVAC (2026), new water heater (2026), and a brand new roof already approved, with materials on site for installation. A just-completed professional refresh adds a renovated kitchen with new white shaker cabinetry, quartz countertops, and stainless steel appliances including a Whirlpool glass-top range and dishwasher, along with updated hardware, lighting, and a new Moen pull-out faucet. Both bathrooms feature updated vanities, quartz countertops, and new faucets, mirrors, and fixtures. Additional improvements include fresh interior paint throughout, new LED lighting and fixtures, updated interior doors and hardware, a new front entry door, a freshly painted garage, and refreshed landscaping with fresh mulch. The functional floor plan offers spacious living and dining areas with a fireplace, a primary suite with a walk-in closet, two additional bedrooms, and an attached 2-car garage. Out back, the screen-enclosed private pool and patio provide year-round Florida living. Low $150 semi-annual HOA and no CDD. Conveniently located near Historic Downtown Winter Garden, Plant Street, the West Orange Trail, shopping, dining, parks, and major roadways. Buyer credit available with use of Seller's preferred lender. Schedule your showing today.

1097 Depot Court, Winter Garden
$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
$689,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West D SubDv. ⋅ 34787 Zip Code
Welcome to Stoneybrook West—a one-of-a-kind community in Winter Garden! This premier neighborhood offers 24-hour guarded entry, a massive town center, and resort-style amenities including an Olympic-sized pool with a splash zone, state-of-the-art fitness center, playground, tennis, basketball, and pickleball courts. Enjoy lakeside living with a fishing/viewing pier and private boat ramp, plus a full calendar of community events. Best of all, your HOA fees cover both internet and cable! Set on a tranquil pond with no rear neighbors, this home boasts irresistible curb appeal from the moment you arrive. Inside, the thoughtfully designed floor plan balances elegance and ease. The front of the home features formal living and dining areas—perfect for hosting—while the rear opens to a bright, open-concept kitchen and family room ideal for everyday living. The kitchen is a chef's delight with ample counter space, a walk-in pantry, stainless steel appliances, stylish tile backsplash, and a breakfast bar. Step through the sliding doors to a screened patio and fully fenced backyard—a private oasis for pets, play, or peaceful pond gazing. Need space for guests or extended family? A main-floor bedroom with a full bath offers flexibility and privacy. Upstairs, a generous loft awaits—use it as a media room, playroom, or second living area. Both the loft and the primary suite open to a screened balcony with serene views. The primary retreat itself is a showstopper, featuring a garden tub, separate walk-in shower, dual vanities with a makeup station, and an enormous walk-in closet. Convenience continues with an upstairs laundry room equipped with cabinets and a utility sink. Fresh new flooring has been installed throughout the entire upper level, and the home has been treated to a brand-new coat of paint, giving it a clean, modern feel throughout. Recent upgrades also include a new roof (2023), new water heater (2023), and AC (2019). You'll also appreciate surround sound pre-wiring in the family room and loft, ceiling fans throughout, and abundant storage. Located just steps from the resident gate, Balforn Tower Way places you minutes from the community town center, golf clubhouse, top-rated schools, dining, shopping, medical facilities, and entertainment. This is more than a home—it's a lifestyle.

2549 Balforn Tower Way, 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
$230,000
2 Beds ⋅ 2 Baths ⋅ Windtree Gardens Condo Ph 01 SubDv. ⋅ 34787 Zip Code
Welcome home to this bright, beautifully maintained and thoughtfully updated first-floor condo in the heart of Winter Garden. This 2-bedroom, 2-bath residence offers 918 square feet of comfortable living space with tasteful improvements and smart use of space throughout. Step inside to an inviting, open living and dining area featuring wood-look luxury vinyl flooring throughout, recessed lighting and an abundance of natural light. Recently replaced windows are an especially valuable improvement, enhancing the home’s fresh, updated feel while offering an upgrade buyers will appreciate for years to come. The kitchen has been tastefully refreshed with granite countertops, a stylish tile backsplash, breakfast bar and thoughtful cabinetry updates, creating a functional space that opens naturally to the dining and living areas. A standout feature is the custom reconfigured laundry and pantry area, thoughtfully redesigned to make the most of the available space. The stackable washer and dryer provides convenient laundry access while allowing for additional organized pantry and cabinet storage—an incredibly functional upgrade that you won’t find in every unit. Both bedrooms are comfortably sized, and the continuous wood-look flooring creates a clean, cohesive feel throughout the home. Additional improvements include a tankless water heater, updated lighting and numerous thoughtful touches throughout. Enjoy your own large covered and screened front porch, offering additional space to relax and enjoy the Florida weather. Combined with convenient first-floor living and a well-maintained community setting, this home offers an easy, comfortable lifestyle in a desirable Winter Garden location. Bright, clean, thoughtfully updated and truly move-in ready—this is a condo that stands out from the rest.

27 Windtree Lane Unit 102, 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
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