Winter Garden/Oakland Homes with One Story Property Description

Winter Garden/Oakland Homes with One Story Property Description

Welcome to the enchanting region of Winter Garden and Oakland, Florida, where charm meets modern living in a picturesque setting. Nestled just a short drive from the vibrant city of Orlando, this delightful area is known for its lush landscapes, historic downtown, and an abundance of recreational opportunities. With its warm climate and friendly community, Winter Garden and Oakland offer the perfect blend of suburban tranquility and urban convenience.

One of the standout features of this region is its array of beautiful one-story homes. These properties are designed to provide comfort and accessibility, making them ideal for families, retirees, and anyone who values a seamless living experience. Imagine waking up to the gentle Florida sun filtering through your windows, enjoying your morning coffee on a spacious patio, or hosting gatherings in an open-concept living area that flows effortlessly into the kitchen.

The one-story homes in Winter Garden and Oakland often boast modern amenities, spacious layouts, and thoughtfully landscaped yards, creating a serene oasis for residents. Many of these properties are situated in family-friendly neighborhoods that prioritize community connection, featuring parks, playgrounds, and walking trails that encourage an active lifestyle.

With a rich history, vibrant arts scene, and a variety of dining and shopping options, Winter Garden and Oakland are not just places to live; they are places to thrive. Whether you’re exploring the scenic West Orange Trail or savoring the flavors at local eateries, you’ll find that this region offers a lifestyle that is both fulfilling and refreshing. Come discover your dream one-story home in this beautiful corner of Florida!

Newest Winter Garden/Oakland Homes with One Story Property Description

$419,900
4 Beds ⋅ 2 Baths ⋅ Deerfield Place SubDv. ⋅ 34787 Zip Code
Exceptional value in the heart of Winter Garden! This estate sale presents a rare opportunity to own a well-maintained home at an attractive price in one of Central Florida’s most sought-after communities. The open-concept floor plan is highlighted by soaring cathedral ceilings, creating a bright, spacious feel throughout the main living areas. Elegant French doors add charm and architectural character, while fresh exterior paint enhances the home’s curb appeal. Step outside to enjoy the fully fenced backyard, offering privacy and plenty of space for outdoor entertaining, pets, gardening, or play. Conveniently located just minutes from Winter Garden Village and historic Downtown Winter Garden, you'll enjoy easy access to shopping, dining, entertainment, parks, and the West Orange Trail as well as a community playground. A fantastic opportunity to add your personal touches and enjoy all that Winter Garden has to offer. Estate sale pricing makes this one a must-see! You’re home.

445 Spring Leap Circle, Winter Garden
$699,000
4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 1a SubDv. ⋅ 34787 Zip Code
Experience refined Florida living in this impeccably maintained single-story 4BD/3BA residence set on an oversized corner lot in the prestigious Waterleigh community. Thoughtfully designed interiors blend elegance with comfort, highlighted by rich finishes, abundant natural light, and a seamless open layout. The gourmet kitchen showcases espresso cabinetry, granite surfaces, a striking center island, modern lighting, stylish backsplash, and a spacious pantry — all appliances included. The primary suite offers a serene retreat with luxury vinyl plank flooring, tray ceiling, quartz dual vanities, a soaking tub, glass-enclosed shower, and an expansive walk-in closet. Step outside to a private oasis featuring a covered screened lanai, brick patio, and a fully fenced yard ideal for quiet relaxation or elevated entertaining. Additional enhancements include a Ring security system, upgraded blinds, garage storage systems, and specialty garage flooring. Just a short stroll from a resident-exclusive clubhouse with a zero-entry pool, fishing pier, lake views, and sand volleyball. Waterleigh’s resort-style amenities elevate daily living with three pools, two fitness centers, tennis and basketball courts, mini golf, splash pad, dog parks, and scenic trails. HOA includes lawn care, irrigation, and tree maintenance. Located near top-rated schools, a nearby fire station, golf, and evening Disney fireworks views, this smoke-free, pet-free home delivers luxury, convenience, and lifestyle in one of Winter Garden’s most coveted communities.

8711 Eden Cove Drive, Winter Garden
$849,988
4 Beds ⋅ 3 Baths ⋅ Lake Cove Pointe 46/58 SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this beautifully maintained custom home located in the gated community of Lake Cove Pointe, within the Winter Garden Golf Cart District. Conveniently located just minutes from Historic Downtown Winter Garden, this home offers easy access to dining, shopping, theater, entertainment, and local avente. A paver driveway and path lead to the charming front porch and welcoming entry. Inside, this nearly 2, 400-square-foot home features 4 bedrooms, 3 full baths, and a spacious three-way split floor plan designed for comfort and privacy. The main living areas feature attractive wood-look ceramic tile, with carpet in the family room and bedrooms. The well-appointed kitchen offers white cabinetry, beautiful countertops, and glass-pane display cabinets for added character and storage. The spacious Owner's Suite includes custom closets, a comfortable sitting area, and French doors leading to the screened-in patio. The Owner's Bath features a large shower and freestanding soaking tub. Enjoy Florida outdoor living from the screened-in patio, complete with a convenient wet bar and sink, making it an ideal space for entertaining or relaxing. The property also offers an immaculate two-car garage with new epoxy flooring, plus a separate third golf cart garage/workshop combination, providing excellent flexibility for golf cart storage, hobbies, or additional workspace. Recent updates include a 2019 roof, 2019 A/C, a Rheem 60-gallon hybrid water heater installed approximately nine months ago, and lifetime garage door springs! installed last summer. Located in a desirable gated community and close to Historic Downtown Winter Garden, this well-maintained home combines a thoughtful floor plan, attractive updates, excellent garage space, and convenient access to all that Winter Garden has to offer.

427 Tierra Verde Lane, Winter Garden
$545,000
3 Beds ⋅ 2 Baths ⋅ Vinings Add Winter Garden SubDv. ⋅ 34787 Zip Code
Discover this beautifully maintained 4-bedroom, 2-bath home nestled in the heart of historic Winter Garden. Featuring a spacious open floor plan with approximately 1,774 square feet of living space, this home offers generous living and dining areas ideal for everyday living and entertaining. The kitchen provides ample cabinet and counter space and opens seamlessly to the main living area. The split-bedroom layout offers privacy for the primary suite, while the additional bedrooms provide flexibility for family, guests, or a home office. Enjoy the convenience of an attached two-car garage, central air conditioning, and a large fenced backyard with plenty of room for outdoor entertaining, gardening, or pets. Located just minutes from Historic Downtown Winter Garden, you'll enjoy easy access to award-winning restaurants, boutique shopping, the West Orange Trail, the Winter Garden Farmers Market, and numerous community events throughout the year. Conveniently located near SR-429, the Florida Turnpike, Downtown Orlando, major employers, and world-renowned theme parks. No HOA makes this an outstanding opportunity for homeowners and investors alike.

300 S Woodland Street, Winter Garden
$275,000
4 Beds ⋅ 1 Baths ⋅ Joe Louis Park SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome home to this quaint WINTER GARDEN gem, offering thoughtful updates throughout the property! It is freshly painted inside and out, and this inviting 4-bedroom, 1-bath home is move-in ready and waiting for its next homeowner. Updated vinyl flooring is installed throughout the home for creating a modern feel and easy maintenance. The bright kitchen features updated white cabinets, granite countertops, and new stainless appliances, creating a stylish but functional space. Additional updates include a newer water heater, updated HVAC, and new washer and dryer in the laundry closet. Utilize one of the four bedrooms as a a home office, home gym or hobby space. Conveniently located in desirable Winter Garden a historic citrus community located west of Orlando featuring brick-lined streets, unique local dining spots, and access to a variety of ecotourism and recreation. Call today to schedule your tour of this affordable opportunity to live in Central Florida. All information within the listing is intended to be correct and should be independently verified by buyer and buyer's agent(s).

1422 Basin Street, Winter Garden
$194,900
3 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo Il SubDv. ⋅ 34787 Zip Code
Welcome to a turnkey resort ownership opportunity at The Grove Resort & Water Park, one of Central Florida’s most amenity-rich vacation destinations. Designed exclusively for short-term resort use, this fully furnished condo offers a spacious, comfortable layout with an open living and dining area, full kitchen with stainless steel appliances, generous cabinetry and ample counter space. The primary suite features a beautifully appointed bath with dual sinks, soaking tub and separate glass-enclosed shower, while modern finishes, updated flooring and neutral tones create a clean, inviting atmosphere throughout. Beyond the unit, The Grove delivers the kind of resort experience Orlando visitors are looking for. Amenities include Surfari Water Park with a lazy river, water slides, zero-entry pool and FlowRider surf simulator, additional resort pools, Lake Austin recreation, fitness facilities, family activities and multiple on-site dining options. Guests can spend the day enjoying the resort or take advantage of convenient access to Central Florida’s world-famous attractions. With the unit offered fully furnished and positioned within an established vacation resort, this property offers an easy way to own a piece of the Orlando vacation market without the responsibilities of a traditional second home.

14501 Grove Resort Avenue Unit 3438, Winter Garden
$1,400,000
4 Beds ⋅ 4 Baths ⋅ Hull Island At Oakland SubDv. ⋅ 34787 Zip Code
Welcome to this extraordinary custom lakefront estate offering breathtaking views of Lake Apopka and the ultimate Florida waterfront lifestyle. Designed with luxury and functionality in mind, this one-of-a-kind home showcases premium upgrades, exceptional craftsmanship, and direct lake access. The heart of the home is a chef-inspired kitchen featuring a natural gas cooktop, double ovens, expansive center island, abundant counter space, separate breakfast dinette, and a custom walk-in pantry with floor-to-ceiling shelving. The kitchen opens seamlessly to the spacious family room with soaring 12-foot ceilings and triple sliding glass doors that frame spectacular lake views and fill the home with natural light. Step outside to your private waterfront oasis where a covered, screened lanai overlooks professionally landscaped grounds and unforgettable sunsets. The impressive 20' x 60' brick paver patio leads to a private dock with an electric covered boat lift, providing direct access to Lake Apopka. Enjoy fishing from your dock, boating the scenic Harris Chain of Lakes via the Apopka-Beauclair Canal, or spending the day exploring the waterfront restaurants, shops, and attractions of historic downtown Mount Dora and Tavares. The thoughtfully designed floor plan includes a formal dining room with soaring ceilings and a private office with double doors, ideal for working from home. The luxurious primary suite is a true retreat with panoramic lake views, spa-inspired bath featuring a frameless floor-to-ceiling tiled double shower with dual shower heads and built-in bench, soaking tub, dual vanities, and custom walk-in closets. A hidden Murphy door provides private access to two secondary bedrooms and a full bath, creating the perfect guest or family wing. The oversized fourth bedroom offers an ensuite bath and walk-in closet, ideal for guests or multigenerational living. Additional premium features include a 24kW natural gas whole-house generator, electric vehicle charging station, water softener, security system, surround sound, insulated garage doors and ceiling, garage utility sink, overhead storage, and a spacious laundry room with built-in cabinetry, extensive counter space, and utility sink. The oversized three-car garage and expansive six-car brick paver driveway provide ample parking and storage. Located in the sought-after gated community of Hull Island, residents enjoy resort-style amenities including a community pool, gazebo, playground, bark park, and exclusive private access to the 150-acre Oakland Nature Preserve with miles of scenic trails. Nestled in the charming Town of Oakland, this exceptional home is just minutes from Winter Garden Village, historic Downtown Winter Garden, the award-winning Winter Garden Farmers Market, the West Orange Trail, Downtown Clermont, shopping, dining, major hospitals, Orlando's world-famous attractions, Orlando International Airport, and major highways. Florida's beautiful east and west coast beaches are approximately one hour away.

1112 Hull Island Drive, Oakland
$239,000
2 Beds ⋅ 2 Baths ⋅ Townhomes Winter Garden SubDv. ⋅ 34787 Zip Code
Welcome to low-maintenance living in the heart of Winter Garden! This charming 2-bedroom, 2-bathroom condominium offers approximately 840 sq ft of comfortable living space in the established Townhomes of Winter Garden community. Enjoy an open floor plan with a bright living and dining area, functional kitchen, and two well-appointed bedrooms, including a primary suite with its own bathroom. In-unit laundry (washer and dryer) adds everyday convenience. The community features a sparkling pool, exterior maintenance, and landscaping included in the HOA, making this an easy, lock-and-leave lifestyle. Prime location just minutes from Historic Downtown Winter Garden’s shops, restaurants, farmers market, and the West Orange Trail. Quick access to Highway 50, Winter Garden Village (shopping, dining, and more), and major roadways for easy commuting throughout Central Florida. Ideal for first-time buyers, downsizers, or investors seeking a solid rental property in a desirable Winter Garden location. Pets are typically allowed (buyer to verify HOA rules). Schedule your private showing today!

300 Eron Way Unit 1, Winter Garden
$910,000
3 Beds ⋅ 3 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code
Built to Impress. Upgraded to Perfection. Welcome to Del Webb Oasis. From the moment you step through the craftsman-style entry onto hardwood floors that run seamlessly through every living space, it becomes clear that every decision in this home was made with intention — and that intention was excellence. Through French glass doors, a private den with tray ceiling offers the quiet focus space today's buyer genuinely needs. Then the kitchen stops you cold. A dramatic galley-style gourmet space with rich wood cabinetry stacked to the ceiling, quartz countertops, gas cooktop with vented hood, built-in wall oven, stainless appliances and a scalloped tile backsplash that earns its own admiration. It connects directly to the side bar — wine refrigerator, diamond-lattice wine rack, quartz countertops and matching backsplash — making the entertaining potential here truly exceptional. The great room beneath soaring double tray ceilings flows naturally through wall-to-wall sliding glass doors to the screened lanai, where a full summer kitchen with granite countertops, built-in grill, stainless hood, refrigerator and sink overlooks a lush conservation backdrop and an oversized fenced yard that is genuinely rare in this community. The primary suite is a proper sanctuary — tray ceiling, dual closets and a spa-caliber ensuite with a dual-sink charcoal vanity, quartz countertops and a floor-to-ceiling tiled walk-in shower with dual shower heads, built-in bench, decorative accent and mosaic tile floor. Two well-proportioned additional bedrooms, a full bath, a polished powder room and a laundry room with cabinetry, utility sink, and full-size washer and dryer complete the picture. Smart home technology, custom water filtration and just off the garage entry, a custom built-in drop zone with beadboard detail, bench, hooks, and shelving creates the perfect transition from the garage into the home — organized, intentional, and exactly where it should be. Now — the address. Del Webb Oasis is not just a community; it's a destination. A boutique, gated 55+ enclave in the heart of Winter Garden, just 2 miles from Disney — close enough that on some evenings, the fireworks are yours to watch from the neighborhood. The 12,000-square-foot clubhouse features a coffee bar, wine lockers, lounge, fitness center, yoga and aerobics studio, arts and crafts room, billiards room, and an indoor-outdoor bar and tavern. Outside: a zero-entry resort pool with lap lanes, spa, cabanas, pickleball and tennis courts, bocce ball, community garden, fire pit, and walking paths. The HOA covers exterior maintenance,and internet — because the only thing on your schedule here is living well. Winter Garden itself offers award-winning Saturday farmers markets, boutique dining on Plant Street, West Orange Trail access, and a charming downtown that genuinely feels like a small town despite being minutes from every major Central Florida corridor.

15084 Canopy Cover Drive, Winter Garden
$834,990
4 Beds ⋅ 3 Baths ⋅ Osprey Ranch SubDv. ⋅ 34787 Zip Code
Under Construction. .

12523 Gold Honeysuckle Street, Winter Garden
$479,900
3 Beds ⋅ 2 Baths ⋅ Crown Point Spgs SubDv. ⋅ 34787 Zip Code
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
$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
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