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Homes for Sale with a Pool in Winter Garden, FL

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Welcome to your dedicated resource for homes for sale with a pool in Winter Garden, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Winter Garden, FL agent, The Nest Group specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the with a pool properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Homes for Sale with a Pool in Winter Garden, FL

$279,900
2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Beautiful 2-bedroom, 2-bathroom condo just under 1,300 sq ft in one of the most desirable areas of Winter Garden. Both bedrooms feature large walk-in closets, and the layout is exceptionally well designed, making the home feel spacious and comfortable. The unit COMES WITH A 1-CAR GARAGE, a rare and valuable feature. All appliances are BRAND NEW, including refrigerator, microwave, stove, and dishwasher. A washer and dryer are also included. The flooring has been completely renovated to elegant wood flooring throughout. The main living area offers a separate flex space that is PERFECT for a home office or a kids’ play area. Conveniently located next to the community car wash, with resort-style amenities that include an amazing clubhouse, pool area with barbecue grills, fully equipped gym, tennis courts, basketball courts, and more.

225 Southern Pecan Circle Unit 208, Winter Garden
$299,900
2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 2 SubDv. ⋅ 34787 Zip Code
PREMIUM BUILDING 3 | RARE 14-FOOT CEILINGS | ELEVATOR-FREE ACCESS | ONSITE RENTAL PROGRAM Step into the largest and most unique 2-bedroom footprint available at The Grove Resort & Water Park. Located on the highly coveted 1st floor of Building 3, Unit 3109 boasts massive 14-foot architectural ceilings exclusive to the ground level, delivering an incredible sense of volume, grandeur, and endless natural light that upper-floor standard units simply cannot match. This fully furnished, turnkey property features the sprawling Cypress Floor Plan (1,434 Sq. Ft.), highlighting a spectacular Dual-Zone Primary Suite complete with its own private attached den. This bonus space acts as a quiet sanctuary, media lounge, or infant nursery entirely separate from the main living room. Why Investors Choose Unit 3109: Zero-Friction Resort Living: Enjoy the luxury of walking straight from the main Building 3 lobby directly into your villa. No elevator wait times, no stairs, and immediate walk-out access to the Surfari Water Park and resort dining. Turnkey Paramount Rental Program: This unit is fully equipped and eligible for immediate enrollment in the world-class, onsite rental program managed by Paramount Hospitality Management. Enjoy completely hands-off ownership with on-site booking, guest check-in, marketing, and property maintenance fully handled for you. Building 3 Dominance: Situated in the newer and most popular phase of the resort, making it highly preferred by incoming vacationers. Luxury Suite Positioning: The added square footage and private owner's lounge elevate this unit into a higher-tier booking bracket on vacation platforms, driving premium guest reviews and repeat bookings. Don't miss the lowest-priced opportunity to own premier Building 3 Cypress luxury! Schedule your showing today.

14501 Grove Resort Avenue Unit 3109, Winter Garden
$565,000
3 Beds ⋅ 3 Baths ⋅ Enclave At Hamlin SubDv. ⋅ 34787 Zip Code
Live in the heart of Hamlin! Welcome to this beautifully upgraded 3 bedroom, 2.5 bath home with a versatile first floor flex room that can easily serve as a fourth bedroom, home office, playroom, or guest space. Built in 2021, this move in ready home offers over 2,100 square feet of thoughtfully designed living space, modern finishes, smart upgrades, and an exceptional location in one of Winter Garden's most sought after communities. Inside, you'll find an open concept floor plan filled with natural light, fresh interior paint, upgraded flooring, and stylish lighting throughout. The kitchen is the centerpiece of the home, featuring Level 5 quartz countertops, a large island wrapped in custom porcelain tile, stainless steel appliances, and abundant cabinet space, making it ideal for everyday living and entertaining. Upstairs, the spacious primary suite features a custom walk in closet and an upgraded en suite bathroom with quartz countertops. Two additional bedrooms, a full bathroom, and an updated laundry room complete the second floor. This home also includes valuable upgrades rarely found at this price point, including a whole home water filtration and softener system, an APCO X Ultra air purification system, five Arlo security cameras that convey, and prewiring for additional smart home connectivity. Outside, enjoy the privacy of a rear entry two car garage and a low maintenance yard, giving you more time to enjoy everything this vibrant community has to offer. Located just minutes from Hamlin Town Center, you'll enjoy waterfront dining, shopping, coffee shops, fitness studios, entertainment, Publix, Cinépolis Luxury Cinemas, top rated schools, and convenient access to State Road 429, making it easy to reach Walt Disney World, downtown Orlando, and Orlando International Airport. Homes offering this combination of flexible living space, thoughtful upgrades, modern finishes, and an unbeatable location are hard to find. Schedule your private showing today and discover why so many buyers are choosing to call this community home.

4642 Prairie Creek Street, Winter Garden
$1,625,000
5 Beds ⋅ 5 Baths ⋅ Bronsons Lndgs F & M SubDv. ⋅ 34787 Zip Code
Rare Gated Lakefront Retreat with Grandfathered Boat Access on Lake Luntz Discover resort-style living in this one-of-a-kind gated lakefront home in the heart of Winter Garden. Nestled on a quiet, tree-lined cul-de-sac, this 5-bedroom, 5-bathroom, 4,365 Sq Ft home offers a smart layout designed for both everyday living and entertaining. The first-floor bedroom and full bath are ideal for guests or multi-generational living, while upstairs includes a loft, media room, and three additional bedrooms, including one en-suite and a Jack-and-Jill setup. Enjoy endless lake views from the screened pool with grotto seating and waterfall, or entertain indoors in the Florida Grill/Bar room featuring a refrigerator, freezer, deep fryer, griddle, bar sink, dishwasher, and full pool/guest bath. The primary suite is a true retreat with double walk-in closets, spa-style bath, garden tub, walk-in shower, and dual water closets. Lake enthusiasts will love the boathouse, covered dock, and boat lift, complete with power and water, along with multiple watercraft options including a pontoon slip (~20’), jet ski slip for 2, power lifts, and additional space for non-powered boats. Additional bonus spaces include a garage under air with a separate gym/rec room. Outdoor living abounds with a beachfront-style area, wood-burning fireplace, granite bar-top seating, and spectacular sunset views. This is a rare opportunity to own the only home on Lake Luntz with grandfathered boat access, offering a private lakefront lifestyle you won’t find anywhere else.

2450 Dahlgren Way, Winter Garden
$434,900
3 Beds ⋅ 3 Baths ⋅ Summerlake Pd Ph 2c 2d 2e SubDv. ⋅ 34787 Zip Code
Perfectly positioned in the heartbeat of Horizons West, just 3 miles from Disney’s Magic Kingdom. This impeccably maintained 3-bedroom, 2.5-bath townhome in the highly sought-after Summerlake community offers the rare blend of style, efficiency, and everyday magic - including a spacious two-car garage attached to the largest oversized patio in Summerlake! Enjoy the nightly Disney fireworks and hear the subtle sounds of Magic Kingdom as you begin your day. Move-in ready and thoughtfully upgraded with a newer HVAC system, this home delivers low-maintenance living and an unbeatable location just minutes from Hamlin Town Center, top-rated schools, and world-class attractions. The open, light-filled floor plan showcases tile flooring, spacious living and dining areas, while an upgraded rustic ‘reclaimed wood’ accent wall blends the modern and organic creating your magical oasis. Enjoy your gourmet kitchen with 42" cabinets, granite countertops, an expansive island and stainless-steel appliances. Upstairs, the primary suite offers dual sinks, granite counters, soaking tub, glass-enclosed shower, private water closet, and a large walk-in closet, along with two additional bedrooms, full bath, and convenient upstairs laundry. Summerlake residents enjoy expansively upgraded resort-style amenities, including a new pool, tennis courts, fitness center, community conservation area, playground, dog park, fishing, scenic trails, and more. The new Summerlake HOA has made this community a truly special place to live - all just minutes to SR 429, Florida Turnpike, Hamlin Town Center, Disney, Orange County National Golf Center, and Orlando Health. Schedule your private showing today!

8113 Red Stopper Lane, Winter Garden
$890,000
4 Beds ⋅ 4 Baths ⋅ Watermark Ph 2b SubDv. ⋅ 34787 Zip Code
Delight your clients with this unique opportunity in Watermark, one of the most desirable communities in Winter Garden. This elegant two-story residence combines sophistication, comfort, and impeccable finishes in every detail, featuring over $150,000 in upgrades that elevate the home’s overall quality and value. It offers 4 bedrooms, 3 full bathrooms, and 1 powder room, along with a simply enchanting outdoor area designed to provide unforgettable moments. Upon entering, a spacious and welcoming foyer leads to open-concept living areas, where the living room and dining room connect harmoniously, creating a bright and airy space ideal for entertaining family and friends. The beautiful porcelain tile floors enhance the elegance of the property. The kitchen is a true highlight, equipped with appliances, high-quality wood cabinetry, and ample countertop space, combining functionality and style for everyday living. On the second floor, all bedrooms provide greater privacy and comfort. The bedrooms feature closets and carpeting, creating a cozy atmosphere. The primary suite is a special retreat, featuring two walk-in closets and a spacious bathroom with dual sinks, offering both practicality and sophistication. The laundry room is also located on the upper floor and includes a sink, washer, and dryer, providing added convenience to the family’s routine. Outside, the property impresses with a fully equipped summer kitchen featuring a built-in grill, granite countertops, cabinetry, and a sink — perfect for gatherings and family moments — integrated with a private heated pool, allowing year-round enjoyment with comfort and exclusivity. Living in Watermark means enjoying resort-style amenities, including a community pool, modern fitness center, tennis court, playground, green areas, and tree-lined sidewalks for outdoor walks. The location is another major advantage: just minutes from Hamlin Town Center, with excellent restaurants, cafés, movie theater, and supermarkets; easy access to Walt Disney World Resort; and close to Florida State Road 429, providing convenient access to Orlando and the entire region. Additionally, it is surrounded by highly rated schools and all the conveniences that Winter Garden offers. A complete home, offering leisure, comfort, and a prime location. Don’t miss the opportunity to live or invest in one of the best addresses in the region.

9218 Holliston Creek Place, Winter Garden
$210,000
3 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code
Exceptional Vacation Investment Opportunity at The Grove Resort & Water Park – Orlando Welcome to this fully furnished 3-bedroom, 2-bath condo-hotel located in the highly sought-after The Grove Resort & Water Park Orlando — one of Central Florida’s premier short-term rental destinations. Featuring the spacious and popular Jasmine floor plan, this residence comfortably accommodates up to eight guests with a private king suite, two queen beds in the secondary bedroom, and a sleeper sofa in the living area. Thoughtfully designed for both durability and guest satisfaction, the unit showcases quartz countertops, stainless steel appliances, in-unit washer and dryer, and a large screened balcony offering peaceful views of the resort and surrounding conservation area. This property operates as a short-term rental, allowing owners up to 179 days of personal use annually while benefiting from full-service, on-site management. The professional management team handles reservations, housekeeping, maintenance, and guest services—making ownership truly hands-off and ideal for out-of-state or international investors seeking passive income. The resort itself delivers a true destination experience, highlighted by the renowned Surfari Water Park featuring a lazy river and FlowRider surf simulator, along with multiple pools, lake access for water activities, fitness center, arcade, glow mini golf, on-site dining, spa services, and 24-hour concierge. Convenient shuttle service to Disney and close proximity to major attractions continue to drive strong occupancy rates year-round. The HOA fee provides exceptional value, covering utilities including electricity, water, cable, WiFi, pest control, and insurance—creating predictable ownership expenses. With continued tourism growth in the Orlando market, strong rental demand, and professional management already in place, this property presents an outstanding opportunity to own a high-performing income-producing asset in one of Florida’s most dynamic vacation corridors. Schedule your showing today and secure your place in this thriving short-term rental market.

14501 Grove Resort Avenue Unit 3611, Winter Garden
$435,000
3 Beds ⋅ 3 Baths ⋅ Hawksmoor-Ph 3 SubDv. ⋅ 34787 Zip Code
Welcome to 16425 Prairie School Drive, a beautifully maintained 2021 townhome located in the highly desirable Hawksmoor community of Winter Garden. This move-in-ready home offers 3 bedrooms, 2.5 bathrooms, a rear-entry two-car garage, and 1,662 square feet of modern living space designed for comfort and convenience. Step inside to an open-concept floor plan featuring tile flooring throughout the main living areas, a spacious living and dining room, and a bright, stylish kitchen complete with a large center island, stainless steel appliances, and ample cabinet space—perfect for entertaining or everyday living. Upstairs, the spacious primary suite features a walk-in closet and private en-suite bathroom, while two additional bedrooms provide flexibility for family, guests, or a home office. Enjoy low-maintenance living and access to Hawksmoor’s resort-style amenities, including a community pool, fitness center, clubhouse, playground, walking trails, and scenic lakes. Conveniently located near Downtown Winter Garden, Flamingo Crossings, major highways, shopping, dining, and Walt Disney World, this home offers an exceptional opportunity to enjoy one of Central Florida’s most sought-after communities. Schedule your private showing today and experience the lifestyle that makes Winter Garden one of the area’s most desirable places to call home.

16425 Prairie School Drive, Winter Garden
$290,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort & Spa Hotel Condo I SubDv. ⋅ 34787 Zip Code
GREAT $10K PRICE REDUCTION: NEW PRICE $290,000.00 MOTIVATED SELLER. WELCOME TO THE GROVE RESORT & WATERPARK, A CONDO HOTEL LOCATED CLOSE TO DISNEY AND ALL THE ORLANDO ATTRACTIONS. THIS BEAUTIFUL LUXURY FULLY FURNISHED 2 BEDROOM/2 BATHROOM BIRCH DESIGN CONDO HAS GREAT COURTYARD VIEWS FROM THE SCREENED BALCONY ON THE 4TH FLOOR. YOU CAN OWN A BEAUTIFUL VACATION CONDO AT THE GROVE RESORT THAT OFFERS PROFESSIONAL ON SITE PROPERTY MANAGEMENT SERVICES TO OWNERS AND THEIR GUESTS. THE GROVE RESORT HAS MANY AMENITIES INCLUDING: WATERPARK, LAZY RIVER, SWIMMING POOLS, WATER SLIDES, SPA, INDOOR & OUTDOOR DINING, FITNESS CENTER, LAKE AUSTIN FOR FISHING AND PADDLE BOATING, SHOPPING AND MUCH MORE.

14501 Grove Resort Avenue Unit 1443, Winter Garden
$340,000
3 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium SubDv. ⋅ 34787 Zip Code
GREAT $10K PRICE REDUCTION: NEW PRICE $340,000.00 MOTIVATED SELLER. WELCOME TO THE GROVE RESORT & WATERPARK, A CONDO HOTEL LOCATED CLOSE TO DISNEY AND ALL THE ORLANDO ATTRACTIONS. THIS BEAUTIFUL LUXURY FULLY FURNISHED 3 BEDROOM/2 BATHROOM JASMINE DESIGN CONDO HAS GREAT WATER VIEWS FROM THE SCREENED BALCONY ON THE 2ND FLOOR. YOU CAN OWN A BEAUTIFUL VACATION CONDO AT THE GROVE RESORT THAT OFFERS PROFESSIONAL ON SITE PROPERTY MANAGEMENT SERVICES TO OWNERS AND THEIR GUESTS. THE GROVE RESORT HAS MANY AMENITIES INCLUDING: WATERPARK, LAZY RIVER, SWIMMING POOLS, WATER SLIDES, SPA, INDOOR & OUTDOOR DINING, FITNESS CENTER, LAKE AUSTIN FOR FISHING AND PADDLE BOATING, SHOPPING AND MUCH MORE.

14501 Grove Resort Avenue Unit 1203, Winter Garden
$1,775,000
6 Beds ⋅ 4 Baths ⋅ Lake Avalon Groves Rep SubDv. ⋅ 34787 Zip Code
Priced to sell and ready to fall in love with. Welcome home to 17224 Old Country Lane. Tucked behind a private gate on over 2.3 sprawling acres, this completely renovated farmhouse-style retreat delivers the rare combination of space, privacy, and location that rarely comes together like this. With 6 bedrooms, 3.5 bathrooms, and 3,629 square feet of thoughtfully designed open-concept living all on one level this home was made for gathering, entertaining, and simply living well. Step outside to your own private oasis: a sparkling pool and spa framed by a screened-in patio, perfect for lazy Florida mornings and unforgettable evenings under the stars. A separate garage offers flexible storage for a boat or additional vehicles, while new septic systems, a private well, and a new electric fence add peace of mind to the property's undeniable charm. All of this just minutes from the shops, dining, and energy of Hamlin, and zoned for sought-after A-rated schools. Homes like this with this much land, this much privacy, and this much heart don't come around often. Schedule your private showing today before it's gone.

17224 Old Country Lane, Winter Garden
$873,000
5 Beds ⋅ 3 Baths ⋅ Winter Grove SubDv. ⋅ 34787 Zip Code
QUICK MOVE IN!!! NEWLY BUILT Highly Desirable Community and Location!! Welcome to Winter Grove in the charming city of Winter Garden. Located 1 mile from Winter Garden Village and 3 miles from Historic Downtown Winter Garden. This Gated New Community features single-family homes on large homesites without a CDD. Step into the Coral Grand by Pulte Homes, where Luxury and Convenience seamlessly combine to create a Truly Elevated Living Experience. This Remarkable 4-Bedroom 3-Bathroom 1-Flex Room Home, Offers an Oversized Driveway and Corner Lot. The Chef-Inspired Kitchen Features Upgraded Dana White Cabinetry (Soft Close), Oversized Quarts Countertops, Undercabinet Lighting, and Whirlpool Stainless Steel Appliances with Exhaust Fan Exterior, Making Cooking a True Pleasure. The Kitchen seamlessly connects to the Café and Extended Gathering room, where a Sliding Glass Door opens to the Covered Lanai, Enhancing the flow of Indoor-Outdoor Living. The Loft area provides the perfect space to unwind, with two additional bedrooms and one bathroom complete the upper level. This Elegant Home is Equipped with a Smart Nest Thermostat, Smart Google Doorbell, ensuring your home is as connected as it is Beautiful. This home offers the perfect combination of Luxury, Convenience, and Modern Design—an ideal place to live and relax. This Split Floorplan Design of the Home and Laundry Room maximizes Privacy, Useful Space, and Peace. Residents also enjoy all the proximity to Shopping Plazas, Restaurants, Parks, and Entertainment this area is known for. Call NOW and Schedule a tour today!

276 Summer Pine Street, Winter Garden
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