Winter Garden/Oakland Homes with Private Pool type

Winter Garden/Oakland Homes with Private Pool type

Welcome to the enchanting region of Winter Garden and Oakland, Florida—a picturesque blend of small-town charm and modern convenience nestled just a stone's throw from the bustling heart of Orlando. Known for its vibrant downtown area filled with quaint shops, delightful restaurants, and lush parks, Winter Garden offers a unique lifestyle that combines relaxation and recreation. The nearby Oakland community adds to the allure, showcasing beautiful landscapes and serene surroundings, making it an ideal place to call home.

One of the most sought-after features of homes in this area is the private pool. Imagine stepping out into your own backyard oasis, where you can bask in the Florida sunshine or unwind under the stars, all from the comfort of your home. Homes with private pools in Winter Garden and Oakland offer the perfect escape for families and individuals alike. Whether you’re hosting summer barbecues, enjoying a refreshing dip on a warm day, or simply lounging poolside with a good book, a private pool enhances your living experience.

With a variety of architectural styles and spacious layouts, these homes cater to diverse tastes and lifestyles. From charming single-family residences to modern designs, there’s something for everyone. Plus, the proximity to top-rated schools, recreational facilities, and beautiful nature trails makes this area not just a place to live, but a community to thrive in.

Explore the possibilities of life in Winter Garden and Oakland, where your dream home with a private pool awaits! Embrace the Florida lifestyle and make every day feel like a vacation.

Newest Winter Garden/Oakland Homes with Private Pool type

$1,750,000
4 Beds ⋅ 4 Baths ⋅ West Lake Hancock Estates SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to an exceptional lakefront estate on the shores of Lake Hancock, one of Central Florida's premier ski lakes. Situated on an expansive 1.26-acre homesite, this beautifully designed residence offers 4 bedrooms, 3 full bathrooms, 1 half bathroom, and nearly 3,400 square feet of thoughtfully crafted living space with breathtaking water views. The open-concept floor plan is perfect for both everyday living and entertaining, featuring formal living and dining rooms, a spacious family room, and a gourmet kitchen complete with quartz countertops, 42-inch cabinetry, stainless steel gas appliances, a pot filler, farmhouse sink, and a convenient butler's pantry. The split-bedroom layout provides privacy, while the bonus room offers endless possibilities as a media room, game room, home office, or home gym. Step outside to your private Florida oasis featuring a screened-in pool and private boat dock with direct access to Lake Hancock. Spend your days boating, skiing, or simply relaxing while enjoying spectacular sunsets and nightly Disney fireworks from your own backyard. Additional highlights include a 3-car garage, high ceilings, elegant architectural details, and access to outstanding community amenities including a resort-style pool, splash pad, clubhouse, fitness center, and scenic walking and biking trails. Ideally located just minutes from Hamlin Town Center, shopping, dining, top-rated schools, SR 429, and Walt Disney World, this remarkable waterfront home offers the perfect combination of luxury, privacy, and convenience.

7573 Green Mountain Way, Winter Garden
$989,000
4 Beds ⋅ 4 Baths ⋅ Cypress Reserve Ph 2 SubDv. ⋅ 34787 Zip Code
Welcome to 14038 Jomatt Loop, where impressive curb appeal, spacious living, and exceptional outdoor entertaining come together. This home is located just steps from A rated schools, has fresh exterior paint, and a large driveway with 3 car garage. Inside, the spacious open floor plan creates an inviting flow between the main living areas, offering plenty of room for everyday life and entertaining. A dedicated theater room provides the perfect setting for movie nights, sporting events, and unforgettable gatherings. Step outside and discover your own private retreat. The beautiful pool, surrounded by a freshly screened lanai, creates an ideal space for relaxing, entertaining, and enjoying the Florida lifestyle year-round. A durable metal fence adds both privacy and peace of mind while complementing the beautifully landscaped property. For added convenience, the home is equipped with a state-of-the-art security system. From its attractive exterior and expansive lot to its upgraded outdoor living spaces and versatile interior, this exceptional home offers the perfect blend of comfort, style, privacy, and entertainment. Schedule your private showing today!

14038 Jomatt Loop, Winter Garden
$1,100,000
3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 2b SubDv. ⋅ 34787 Zip Code
Welcome to your LAKEFRONT dream home and backyard oasis! This popular “Delmar” floor plan with 120’ of DOCKABLE lake frontage on skiable Hickory Nut Lake which expends 403 acres. You will love the lake lifestyle enjoying boating, waterskiing, kayaking, or fishing! This is a great fishing lake known for it’s Largemouth bass, Bluegills, and Spotted Gars. When you’re done boating, you can finish the day in your heated swimming pool or spa. The pool and spa have all the works, including an electric AND solar heater, plus pool lights for night swimming. This home features a sizable covered lanai perfect for dining a la fresca by the pool enjoying the lake views with all the privacy having no rear neighbors. When night time comes, you will enjoy your nightly DISNEY fireworks view. A bonus of this lot is that it is pie shaped, so there is a spacious yard beside the pool that is fenced in for your furry friends. This sprawling 1 story home is located on a small alcove offering privacy from the main access road. You can sit on the covered front porch enjoying sunset views. The interior of this home is perfect for entertaining, featuring an open concept living area complete with family room/kitchen/dining combo. The stunning kitchen features a wall oven and wall microwave, cooktop, and large walk-in pantry. This “emerald series” house has all the upgrades including tile roof, custom built in closets, custom woodwork and wainscoting, 8 ft interior doors, tray ceilings, whole house water softening system, luxury LVP all throughout (no carpets!), trim lights built into the soffit for all of your holiday lighting needs, and a new dishwasher. The exterior was hand painted in August 2026, so this is truly a turn key home! Located in the sought after Horizon West area zoned for “A” schools including Atwater Bay Elementary, Water Spring Middle School, and Horizon West High. Along with its amazing location, the Waterleigh community also offers a beautiful clubhouse with resort style pool, miniature golf course, beach volleyball, grills, picnic areas, water view, walking trails, and "bark parks" for your furry friends; making it a perfect place for the family lifestyle. Don't like mowing the lawn and weeding the shrubs? No problem, the HOA takes care of that for you here. Love the Florida golf cart life? You can take your street legal golf to the community pool, and join the neighbors for lots of fun, holiday golf cart parades!! Within minutes you have loads of shopping and activities including Hamlin center, Flamingo Crossings shopping center, and Disney parks and resorts! All you have to do is move in and start enjoying the lifestyle Waterleigh provides!

10043 Little Alcove Loop, Winter Garden
$1,460,000
5 Beds ⋅ 5 Baths ⋅ Twinwaters SubDv. ⋅ 34787 Zip Code
Welcome to 16548 Raven Rock Place, an exceptional residence located in the highly desirable Twinwaters community of Winter Garden. Built in 2017, this beautifully designed two-story home offers 4,263 square feet of living space with 5 bedrooms, 5 full bathrooms, and a spacious 3-car garage on an 8,402-square-foot homesite. Designed with comfort and functionality in mind, this home features an expansive open-concept floor plan, high ceilings, large windows that fill the home with natural light, a dedicated office, loft, bonus room, mud room, laundry room, spacious walk-in closets, and ensuite bathrooms. The flexible layout provides multiple living and gathering spaces for everyday living, entertaining, remote work, fitness, and recreation. The chef's kitchen is thoughtfully designed with quartz countertops, stainless steel appliances, a large kitchen island, walk-in pantry, butler's pantry, double ovens, abundant cabinetry, and overlooks the main living areas, creating the perfect setting for cooking and entertaining. Step outside to enjoy your own private outdoor retreat featuring a screen-enclosed heated saltwater swimming pool, covered patio, covered lanai, pool bath, outdoor summer kitchen, built-in barbecue, and outdoor fireplace, providing exceptional indoor-outdoor living throughout the year. Additional highlights include smart home features, energy-efficient features, tile roof, paver driveway, a dedicated fitness room, and a spacious 3-car garage. Conveniently located near Hamlin Town Center, Horizon West, Downtown Winter Garden, restaurants, coffee shops, retail shopping, grocery stores, parks, walking trails, golf courses, medical facilities, Walt Disney World Resort, SR-429, and the Florida Turnpike, providing convenient access throughout Central Florida. This property offers an exceptional combination of space, design, premium finishes, and outstanding indoor and outdoor amenities in one of Winter Garden's most sought-after communities. Schedule your private showing today.

16548 Raven Rock Place, Winter Garden
$468,000
3 Beds ⋅ 2 Baths ⋅ Oak Park At Winter Garden SubDv. ⋅ 34787 Zip Code
Located in the desirable charming golf cart community of Oak Park within a couple blocks of walking distance (or golf cart) to historical Winter Garden vibrant downtown with dining, boutique shopping and entertainment featuring a theatre and an award-winning farmers market. This well built cement block Maronda home offers a blend of charm and convenience with low HOA dues, and can be easily updated. Step out of this home into a wonderful screened heated pool and covered lanai for year-round enjoyment. The almost third acre lot is fenced on 3 sides and easily fenced and gated on each side for privacy. Within the wooded area in the back of the lot is an attractive storage shed. Veterans Memorial Park borders on the rear of the property featuring several acres of a variety of sports, including ten pickleball courts, picnic areas and playgrounds for families and pets. Hop on the scenic West Orange Trail just minutes from this home for a walk, run or bike ride. Commuting via the 429 and the Florida Turnpike gives easy access to all of Central Florida and its theme parks.

665 Stevelynn Circle, Winter Garden
$775,995
5 Beds ⋅ 3 Baths ⋅ Winter Oaks SubDv. ⋅ 34787 Zip Code
Nestled in the sought-after golf cart district just minutes from Historic Downtown Winter Garden, this spacious 5-bedroom, 3-bath smart home in Winter Oaks offers the perfect blend of comfort, style, and convenience. A rear-entry garage enhances the home's exceptional curb appeal, while the thoughtfully designed floor plan is ideal for both everyday living and entertaining. The first floor features formal living and dining rooms, a bedroom that also makes an ideal home office, a full bath, a separate laundry room, and a beautifully appointed kitchen with 42-inch cabinetry, granite countertops, stainless steel appliances, and a sunny breakfast area. Upstairs, the private primary suite provides a peaceful retreat with tray ceilings, a private balcony, an oversized walk-in closet, dual vanities, a garden tub, and a separate walk-in shower. Three additional bedrooms complete the second floor. Step outside to enjoy the fenced backyard featuring an expansive screened outdoor living area and a private plunge pool/spa, creating your own backyard oasis. Additional highlights include a new roof, tankless water heater, 16-camera security system, landscape lighting, and optional furnishings, including a baby grand piano. Residents of Winter Oaks enjoy exceptional community amenities, including a resort-style pool, playground, scenic walking trail, tranquil ponds with fountains, and a charming entrance highlighted by a restored historic water tower. Just one mile from the award-winning Winter Garden Farmers Market, Plant Street's popular shops and restaurants, the West Orange Trail, and convenient SR-429 access, this home offers an exceptional opportunity to enjoy one of Central Florida's most desirable lifestyles.

644 Autumn Oaks Loop, Winter Garden
$1,499,997
6 Beds ⋅ 4 Baths ⋅ Brdford Crk Ph 2 SubDv. ⋅ 34787 Zip Code
WELCOME TO YOUR PRIVATE RESORT IN THE HEART OF WINTER GARDEN! Located behind the gates of the desirable Bradford Creek community, this exceptional 6-bedroom, 4-bath residence offers the space, flexibility, luxury, and unforgettable outdoor lifestyle today’s buyers are searching for. From the oversized driveway and 3-car garage to the breathtaking resort-style backyard overlooking the pond, this home was designed for elevated everyday living and exceptional entertaining. Step inside to a bright, expansive open floor plan featuring a formal dining room, private office or den, spacious living areas, and a highly desirable first-floor bedroom with a full bathroom—ideal for guests, multigenerational living, or a private work-from-home space. The impressive kitchen is the heart of the home and features stainless steel appliances, abundant cabinetry, a large pantry, a convenient butler’s pantry, and a seamless connection to the main living area. The first-floor laundry room adds everyday convenience, while the spacious second-floor loft offers flexible space for a media room, game room, fitness area, home office, or additional family lounge. The expansive primary suite provides a peaceful retreat with generous space and a large walk-in closet. Step outside and experience what truly sets this property apart. The fully fenced backyard has been transformed into a private resort-inspired oasis featuring a spectacular luxury pool with decorative fire features, a swim-up pool bar, and a relaxing spa. Entertain year-round from the summer kitchen and covered gazebo, unwind beside the Zen-inspired pond, gather around the dedicated fire-pit area with four loungers, or enjoy the beauty of the thoughtfully designed butterfly gardens. Low-maintenance artificial turf creates a polished outdoor setting, while peaceful pond views provide a beautiful backdrop for relaxing mornings and memorable evenings. FEATURES INCLUDE: Gated community; 6 bedrooms and 4 bathrooms; 3-car garage; oversized driveway; first-floor bedroom and full bathroom; private office or den; formal dining room; open-concept living; stainless steel appliances; large pantry; butler’s pantry; first-floor laundry; spacious loft; expansive primary suite with a large walk-in closet; resort-style pool; decorative fire features; swim-up pool bar; spa; summer kitchen; covered gazebo; pond views; Zen-inspired pond; fully fenced backyard; artificial turf; butterfly gardens; and a dedicated fire-pit lounge. Enjoy the highly sought-after Winter Garden lifestyle with convenient access to Historic Downtown Winter Garden, local restaurants, coffee shops, boutique shopping, entertainment, community events, and the popular farmers market. Explore the nearby West Orange Trail, area parks, lakes, fitness facilities, shopping centers, grocery stores, and everyday conveniences. The home also offers convenient access to major roadways, Central Florida attractions, employment centers, and the extensive shopping and dining options surrounding Winter Garden Village. This exceptional property combines the privacy of a gated community, the versatility of a 6-bedroom floor plan, and the lifestyle of a private resort in one of Central Florida’s most desirable locations. Homes offering this level of indoor space, outdoor luxury, pond views, and entertaining potential are rarely available. Schedule your private showing today and experience this extraordinary Winter Garden residence for yourself!

14384 Sunbridge Circle, Winter Garden
$2,860,000
6 Beds ⋅ 6 Baths ⋅ Signature Lks-Pcl 01d Ph 02 - Independence SubDv. ⋅ 34787 Zip Code
Virtually Staged. The photo showing Disney fireworks is the only pic that is virtually staged. This beautiful Hancock Lake family friendly home is custom built for maximum lakefront enjoyment including a private covered dock protecting a 20’ +/- boat and 2 jet skis. Motor boat or pontoon around the lake, drop a line in or ski on one of the best skiing lakes in the area. The cul-de-sac lot is 1.29 acres with a BIG fenced yard, manicured gardening beds for your green thumb and plenty of room for outdoor games and pets. The extended screened patio has a sleek outdoor Kitchen with durable Weatherstrong cabinetry, cabana bath and a custom salt pool showcasing a water slide, Fiber optic lighting, solar heated and whimsical Disney characters embedded in the rock’s facade. Relax to lake views, or pull down the projector screen for a movie then watch the Disney’s fireworks nightly over the lake. The home has a freshly painted exterior and interior with crown trim throughout. The Kitchen space is designed for multiple chefs with newer appliances, walk-in pantry, island and informal seating. The first level’s primary suite with patio access was previously a media room complete with surround sound that remains intact. The loft with a balcony overlooking the patio and lake is prepped for entertaining. Two additional ensuites, 3 more bedrooms and a laundry room are also on the upper level. Both A/C Systems, all patio doors, reinforced exterior balcony railings and LR/DR bamboo engineered hardwood flooring are updated. The community offers a wide selection of amenities from boat ramp to pools for residents to enjoy.

7301 Wild Blackberry Trail, Winter Garden
$890,000
5 Beds ⋅ 5 Baths ⋅ Hawksmoor Ph 4 SubDv. ⋅ 34787 Zip Code
Stunning two-story house with a permanent lake view. Be enchanted by this magnificent lakefront residence, which combines sophistication, comfort, and a privileged location. It features 5 bedrooms, 4 full bathrooms, and 1 powder room, distributed in a smart and functional layout. The social area impresses with high ceilings in the living room and sliding doors that open onto a large covered veranda, integrated with a heated pool with a safety net, ideal for leisure and entertainment throughout the year. The living room is integrated with the dining room and the spacious and elegant gourmet kitchen, equipped with a generous central island, appliances, and wooden cabinets, perfect for those who enjoy entertaining. The master suite on the ground floor offers complete privacy, as well as relaxing views of the lake and green area, and a full bathroom on the same level. On the second floor, the house also features a versatile loft, ideal for an office, TV room, or social space. The space originally intended for a garage has been carefully adapted into a private gym, and can easily be converted back to suit the new owner's needs. Located in the desirable Hawksmoor community, the property offers complete infrastructure, including a community pool, gym, clubhouse, and walking paths. All this in a strategic location, close to markets, restaurants, shops, a theater, major highways, and Disney parks. A unique opportunity to live or invest. Schedule your visit and be amazed!

16394 Taliesin Street, Winter Garden
$425,000
3 Beds ⋅ 3 Baths ⋅ Suburban Shores Rep Pt Blk 03 SubDv. ⋅ 34787 Zip Code
Virtually Staged. Discover the potential of this spacious 3-bedroom, 3-bathroom home in Winter Garden, offering a flexible layout and plenty of room to make it your own. With 3 full bathrooms and a large flex room, this home provides endless possibilities for a home office, media room, hobby space, game room, or additional living area. The pool bathroom was added in 2018 with wheelchair-accessible features, including a zero-threshold shower and exterior ramp for ease of access. Major improvements include a metal roof (2018), whole-house generator (2017), flex room windows (2018), A/C (2013), and water heater (1999). Enjoy access to Johns Lake with a public boat ramp conveniently located at the front of the neighborhood, making it easy to spend the day boating, fishing, kayaking, or enjoying one of Winter Garden's most popular lakes. Situated with convenient access to Florida's Turnpike, Highway 50, shopping, dining, and everyday conveniences, this home offers a great opportunity for buyers looking for space, versatility, and a desirable Winter Garden location.

17531 N Sunset Terrace, Winter Garden
$1,095,000
5 Beds ⋅ 4 Baths ⋅ Westfield Lakes SubDv. ⋅ 34787 Zip Code
Welcome Home! Meticulously maintained home boasting with upgrades on an oversized conservation lot with peaceful pond views. Designed for both everyday living and entertaining, features a completely remodeled kitchen with quartz countertops, premium Café appliances, designer backsplash, a massive island with sitting space, upgraded lighting and a custom walk-in pantry. The first floor includes a private office, spacious family room, guest suite with a full bath, laundry room, formal living, and dining room. Porcelain tile flows throughout the main living areas, French doors lead to your private backyard retreat with a fully screened lanai overlooking the saltwater pool and spa, complete with new tile. Upstairs you'll find a stunning media room complete with theater seating and a granite wet bar, 4 bedrooms and a full bath. The primary suite features tray ceiling, plantation shutters, dual walk-in closets, and remodel ensuite bath. Updates include dual vanities, walk-in glass shower, clawfoot tub, and stunning upgraded tile throughout. Two car garage with an upgraded paver driveway. Located in a highly sought-after community of Westfield Lakes. Excellent public schools and convenient access to shopping, dining, and major highways, this exceptional home offers the perfect combination of luxury, comfort, and location. Schedule a private showing today!

626 English Lake Drive, Winter Garden
$650,000
3 Beds ⋅ 2 Baths ⋅ Lakeview Pointe/Horizon West P SubDv. ⋅ 34787 Zip Code
Great house fronting the park, gym, and community pool. Tons of upgrades inside and out. Beautiful screened pool with motorized shade for privacy on patio. Saltwater pool. Luxury Vinyl Plank throughout the house. NO Carpet! Kitchen has lots of upgrades as well. KitchenAid appliances. Wall oven and cooktop. Samsung refrigerator included. Washer and Dryer also stay! 5 mounted TV's will convey as well! Ring alarm system with cameras as well. Plantation shutters throughout.

14048 Lake Abbotts Drive, Winter Garden
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