Winter Garden/Oakland Homes with Community Pool type

Winter Garden/Oakland Homes with Community Pool type

Welcome to the enchanting region of Winter Garden and Oakland, Florida—a vibrant community nestled in the heart of Orange County. Known for its picturesque landscapes and charming downtown, this area boasts a delightful blend of small-town charm and modern conveniences. With its lush greenery, scenic lakes, and friendly neighborhoods, Winter Garden and Oakland offer a lifestyle that is both relaxed and invigorating.

One of the standout features of this region is the abundance of beautiful homes equipped with community pools. Imagine coming home to a stunning property where you can unwind and socialize with neighbors by the shimmering waters of a shared pool. These community pools are not just a place to cool off; they serve as a gathering spot for families and friends, fostering a sense of camaraderie and community spirit.

In Winter Garden and Oakland, you’ll find a diverse range of homes—from cozy single-family residences to luxurious estates—each designed to cater to various lifestyles. Many of these properties feature modern amenities and spacious layouts, ensuring comfort and convenience for all residents. The neighborhoods are designed with families in mind, often including playgrounds, walking trails, and community events that make it easy to connect with others.

With its prime location just a short drive from the attractions of Orlando, Winter Garden and Oakland provide the perfect balance of tranquility and excitement. Whether you’re looking to dive into a refreshing pool or explore the local farmers' market, this community has something for everyone. Discover your dream home in Winter Garden and Oakland—where community and comfort come together beautifully!

Newest Winter Garden/Oakland Homes with Community Pool type

$219,000
3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo Li SubDv. ⋅ 34787 Zip Code
**Spacious 3-bedroom, 3-bathroom fully-furnished condo located on the fourth floor of the beautiful Grove Resort and Water Park! This condo has a full kitchen, full washer and dryer, large primary bedroom with sitting area, large primary bathroom with dual sinks and separate shower and tub, a second bedroom with its own ensuite bathroom, and a third bedroom and bathroom. The screened-in balcony overlooks the central fountain area, so the location is only a short stroll away from any amenities! You have the Surfari water park with a large heated pool, lazy river, water slides, splash area, and the Flowrider surfing experience! The Longboard Bar and Grill is located inside the water park for delicious meals, snacks and drinks! Or visit the Springs Pools area which has three further pools, and the relaxing hot tub! Located next to the Valencia Restaurant, the outdoor bar is also located there, and the 24/7 gym! Take a stroll down to Lake Austin and try your hand at fishing, kayaking, or paddle a swan boat!! For indoor fun visit Flip Flops, the 6000 sf games arcade with glow-in-the-dark mini golf!! For your convenience for food, gifts and sundries, we have the Marketplace, located at the Front Desk area. A free daily shuttle to the Disney parks is also provided for owners and guests. Enjoy ownership of a vacation condo, while having the onsite management company place bookings in your unit while you are not there! It is a completely hands-free experience! Call now for more details!!**

14501 Grove Resort Avenue Unit 3401, Winter Garden
$581,000
4 Beds ⋅ 3 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Toll Brothers new construction in Winter Garden, Horizon West. Estimated completion in 2027. The Montpelier bungalow offers a thoughtfully designed layout with a covered entry leading to a spacious foyer and a private guest suite. The main living area features an open-concept design with a dining area, breakfast bar, great room, and access to the courtyard, creating a comfortable space for everyday living and entertaining. The second floor includes two secondary bedrooms and a private primary suite featuring a large walk-in closet and a well-appointed bath with dual vanities, separate shower, and private water closet. Additional highlights include the functional bungalow design, inviting courtyard space, and the opportunity to personalize select design features based on the stage of construction

13020 Sunset Garden Lane, Winter Garden
$660,000
4 Beds ⋅ 4 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Toll Brothers new construction. The Autumn townhome offers 2,593 square feet of thoughtfully designed living space with 4 bedrooms and 4 bathrooms. An inviting foyer leads to a first-floor bedroom, ideal for guests, a home office, or flexible living. The open-concept floor plan seamlessly connects the kitchen, casual dining area, and great room, creating an ideal space for everyday living and entertaining. The kitchen features designer cabinetry, upgraded countertops, and a decorative tile backsplash. Upstairs, the private primary suite includes a spacious walk-in closet and en-suite bath, while two secondary bedrooms share a full bathroom. Additional highlights include a private rear courtyard, a detached 2-car garage with a versatile loft above that provides additional flexible living space for a home office, media room, fitness area, or playroom, and professionally selected finishes throughout. Residents enjoy access to resort-style community amenities.

12776 Sunset Walk Drive, Winter Garden
$563,000
3 Beds ⋅ 3 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Welcome to this beautifully designed new construction bungalow by Toll Brothers in the desirable Winter Garden/Horizon West area, with estimated completion in April 2027. A covered front entry welcomes you into a spacious foyer that opens to a versatile flex space, ideal for a home office or additional living area. The open-concept floor plan features a well-appointed kitchen with a breakfast bar overlooking the dining area and a great expansive room, creating the perfect setting for everyday living and entertaining. Enjoy seamless indoor-outdoor living with access to the private courtyard. The spacious primary suite offers a large walk-in closet and a luxurious bath complete with dual vanities, a separate shower, and a private water closet. Experience thoughtfully designed living in one of Central Florida's most sought-after communities.

13056 Sunset Garden Lane, Winter Garden
$605,000
3 Beds ⋅ 4 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Welcome to the Crowley townhome by Toll Brothers, located in the desirable Winter Garden/Horizon West area. This thoughtfully designed new construction home features a covered front entry that opens to a spacious, open-concept living area, seamlessly connecting the great room, kitchen, and dining space. Enjoy outdoor living in the private courtyard with convenient access to the detached 2-car garage. Above the garage, a finished loft with a full bathroom adds approximately 550 square feet of flexible living space, perfect for a guest suite, home office, fitness room, media room, or hobby space. The spacious primary suite offers a large walk-in closet and a well-appointed bath featuring dual vanities and a separate shower. Experience low-maintenance living with exceptional design in one of Central Florida's most sought-after communities.

12800 Sunset Walk Drive, Winter Garden
$537,000
3 Beds ⋅ 3 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Welcome to this stunning new construction home by Toll Brothers in the highly sought-after Winter Garden/Horizon West area, with estimated completion in April 2027. Designed with both everyday living and entertainment in mind, this thoughtfully crafted floor plan offers an open-concept great room, kitchen, and dining area that seamlessly flow together. A covered front entry welcomes you inside, while the covered lanai and spacious private courtyard create the perfect outdoor retreat with convenient access to the detached 2-car garage. The luxurious primary suite features a generous walk-in closet and a spa-inspired bath with dual vanities, a separate shower, and a private water closet. Don't miss this opportunity to own a beautifully designed new home in one of Central Florida's most desirable communities.

13038 Sunset Garden Lane, Winter Garden
$270,000
2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Welcome to this newly updated 2 bedroom / 2 bathroom first floor condo in Winter Garden, where low-maintenance living meets comfort and convenience. This beautifully updated first-floor condo features fresh interior paint and new flooring, creating a bright, modern, and move-in-ready space. The open-concept floor plan offers comfortable living and dining areas, making it perfect for everyday living or entertaining. The well-designed layout provides a seamless flow, while large windows bring in an abundance of natural light. This condo hasa detached garage for easy parking near your home. Residents enjoy the outstanding amenities of this sought-after community, including a resort-style swimming pool, fitness center, clubhouse, playground, walking paths, and beautifully maintained green spaces. The HOA also provides low-maintenance living, allowing you more time to enjoy everything Winter Garden has to offer. Ideally located just minutes from Historic Downtown Winter Garden, the West Orange Trail, Winter Garden Village, shopping, dining, entertainment, major highways, and Orlando's world-famous attractions, this home offers an unbeatable combination of location and lifestyle. Whether you're a first-time homebuyer, seasonal resident, downsizing, or looking for an investment opportunity, this move-in-ready condo delivers exceptional value in one of Central Florida's most desirable communities.

130 Southern Pecan Circle Unit 103, Winter Garden
$470,782
3 Beds ⋅ 3 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Welcome to The Regina II in Northlake at Ovation, where modern design meets everyday convenience. This thoughtfully crafted home offers spacious living areas perfect for both relaxing and entertaining. Nestled in the highly sought-after Winter Garden area, this home is conveniently located to top rated schools, shopping, grocery stores, Horizon West restaurants, and Walt Disney World. This low maintenance townhome includes a detached two car garage with private fenced courtyard space. The open kitchen boasts plenty of modern upgrades from the AW Collection Coastal such as beautiful 42 inch cabinets, tiled backsplash, and stainless steel appliances. Large island with upgraded quartz countertops perfect for gatherings. The main living areas feature wood look luxury vinyl plank flooring and the bedrooms include upgraded carpet for comfort, plus find upgraded 8' doors throughout the home. Enjoy the neighborhood amenities including a community pool, clubhouse, shaded playground, and dog park. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.

17398 Sweet Moro Drive, Winter Garden
$1,495,000
4 Beds ⋅ 5 Baths ⋅ Winter Garden Shores 2nd Add SubDv. ⋅ 34787 Zip Code
Discover elevated living and the Winter Garden lifestyle in downtown's newest custom residence! Ideally positioned off the shores of Lake Apopka and within the beloved golf cart district, this exceptional home offers effortless access to Plant Street’s charming shops, restaurants, Farmers Market, Brewery and West Orange Trail. Thoughtfully designed by locals with a deep appreciation for the character of this historic city, this exquisite 4 bedroom, 4.5-bath home blends timeless charm with refined modern finishes throughout. Majestic oaks beautifully frame the home’s craftsman-inspired architecture, while the expansive front porch invites relaxation. Inside, an open-concept design and modern kitchen are curated for both everyday comfort and endless entertaining. Inviting living spaces are complemented by elevated finishes, a wine bar, custom built-ins, a butler’s pantry & outdoor kitchen. Creatively designed to include a drop zone with a one-of-a-kind dog wash station. All bedrooms feature ensuites and custom closets. Don't miss this one-of-a-kind opportunity. Schedule your private showing today!

412 N Boyd Street, Winter Garden
$265,000
2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained 2-bedroom, 2-bath first-floor unit with a 1-car garage, located in the highly desirable gated community of Southern Pines in the heart of Winter Garden. Offering the perfect combination of comfort, convenience, and resort-style living, this home is ideal for first-time buyers, downsizers, investors, or anyone seeking a low-maintenance lifestyle. The thoughtfully designed floor plan features spacious living areas, two generously sized bedrooms, and two full bathrooms, all conveniently situated on the first floor for easy access. Enjoy the added value of water, internet, and cable included in the monthly Condo fee, making everyday living both simple and budget-friendly. Southern Pines is known for its outstanding amenities, offering residents a true resort-style experience. Spend your days relaxing by the sparkling pool and hot tub, entertain friends at the BBQ grills and outdoor kitchen, or enjoy the beautifully appointed clubhouse featuring a movie theater, business center, and billiards room. Stay active with the fully equipped fitness center, indoor basketball and racquetball courts, tennis courts, beach volleyball court, and a covered outdoor playground. Additional conveniences include a car wash station and beautifully maintained grounds throughout the community. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, major highways including SR-429 and the Florida Turnpike, shopping, dining, entertainment, and world-renowned theme parks, this condo offers an unbeatable location with exceptional amenities. Don't miss your opportunity to own a piece of one of Central Florida's most sought-after communities!

405 Southern Pecan Circle Unit 108, Winter Garden
$319,000
2 Beds ⋅ 3 Baths ⋅ Daniels Lndg A-J SubDv. ⋅ 34787 Zip Code
LISTED AT APPRAISED VALUE! Welcome to this beautifully updated townhome in the highly desirable gated community of Daniels Landing in Winter Garden. Combining modern upgrades with an ideal location, this move-in-ready residence offers the perfect blend of style, comfort, and convenience. Step inside to discover an inviting open-concept main level featuring a spacious living room, a well-appointed kitchen with granite countertops, ample cabinetry, a dining area, and a convenient half bath for guests. Luxury wood plank flooring flows throughout the living room and both bedrooms, creating a warm and cohesive feel. Upstairs, you'll find two generously sized primary suites, each complete with walk-in closets and private en-suite bathrooms. The bathrooms were fully renovated in 2025 with designer tile flooring, new vanities, LED mirrors, beautifully tiled showers, new toilets, and contemporary fixtures, creating spa-inspired spaces you'll love. A conveniently located upstairs laundry area adds to the home's thoughtful layout. Extensive recent improvements provide exceptional peace of mind, including a complete HVAC system replacement (2022), new garage door and garage door opener (2025), professionally cleaned air ducts with a UV air purification system (2025), new ceiling fans throughout (2025), and a full suite of brand-new LG stainless steel appliances including the refrigerator, dishwasher, microwave, washer, and dryer (2025). Enjoy Florida living in your private courtyard, accessible from the rear-entry garage, offering a quiet outdoor retreat for relaxing or entertaining. Residents of Daniels Landing enjoy an array of community amenities, including a resort-style pool, fitness center, clubhouse, playground, and gated entry. Ideally situated just minutes from the award-winning Downtown Winter Garden, the West Orange Trail, shopping, dining, major highways, and approximately 20 minutes from Walt Disney World, this exceptional home offers the perfect combination of low-maintenance living and an unbeatable location.

241 Deepcove Road, Winter Garden
$908,142
5 Beds ⋅ 5 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Discover elevated living in this thoughtfully designed home at Northlake at Ovation, offering flexible spaces and curated finishes to fit your everyday lifestyle. From the inviting covered lanai to the spacious loft and soaring ceilings, this floor plan provides room to relax, work, and entertain with ease. Inside, you’ll find a balance of bold and neutral finishes from the AW Collection Rosemary. Design upgrades include 8' interior doors, quartz countertops, tiled backsplash, stainless steel appliances and more. Whether you’re hosting gatherings or enjoying quiet evenings at home, the open layout and versatile rooms adapt to your needs. Perfectly located in Winter Garden near some of Central Florida’s most beloved destinations, this home is just 35 minutes from Orlando International Airport, 15 minutes from world-famous Disney theme parks, and 30minutes from charming Celebration. Residents can also enjoy the charm and rich local history of nearby downtown Winter Garden, known for its vibrant shops, and eateries. Paired with great local schools and a peaceful community setting, this home delivers the ideal blend of comfort, convenience, and Central Florida living. Residents also enjoy a clubhouse, community pool, playground areas and dog park. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.

17625 Lake Star Road, Winter Garden
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