Winter Garden, FL Homes for Sale with Private Pool

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  /44

  $1,345,000

  • 5 Beds
  • 6 Baths
  • 4,340 Sq Ft

  9574 Meadow Hunt Way, Winter Garden, FL 34787

  NEW PRICE | Experience luxury living in this immaculate, semi-custom home within Watermark at Horizon West. Built by Meritage Homes, the Lafayette sits on over a quarter acre combining breathtaking water and preserve views with modern elegance. Nestled in tranquility, this 5-bedroom, 3 full and 3 half-bath masterpiece is designed for those who love to entertain and enjoy life's finest comforts.

  Toni Marie Cafferty COMPASS FLORIDA LLC

  9574 Meadow Hunt Way, Winter Garden, FL 34787
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  $839,900

  • 6 Beds
  • 4.5 Baths
  • 3,775 Sq Ft

  13044 Lakeshore Grove Dr, Winter Garden, FL 34787

  Stunning 6-Bedroom POOL Home on Oversized Lot in Gated Wintermere Harbor! Welcome to this spacious and beautifully updated 6-bedroom, 4.5-bathroom home in the highly desirable gated community of Wintermere Harbor! Situated on a generous 0.38-acre lot, this move-in ready residence offers the perfect blend of elegance, comfort, and functionality—IDEAL FOR LARGE or MULTIGENERATIONAL

  Alena Kolyadchik REALTY HUB

  13044 Lakeshore Grove Dr, Winter Garden, FL 34787
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  $610,000

  • 3 Beds
  • 2 Baths
  • 2,365 Sq Ft

  690 Cascading Creek Ln, Winter Garden, FL 34787

  ***Stunning 3/2 Home with Office in Desirable BLACK LAKE PARK Gated Community with Resort-Style Amenities***Welcome to this beautifully appointed home with an office, located in the highly sought-after Black Lake Park gated community in Winter Garden. Nestled in a prime location, this spacious residence offers the perfect blend of comfort, style, and convenience.Step inside to

  Vicky Koehlke CENTURY 21 CARIOTI

  690 Cascading Creek Ln, Winter Garden, FL 34787
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  /83

  $1,495,000

  • 6 Beds
  • 5 Baths
  • 4,493 Sq Ft

  10139 Austrina Oak Loop, Winter Garden, FL 34787

  Welcome to 10139 Austrina Oak Loop! Featuring SIX BEDROOMS PLUS OFFICE and FIVE FULL BATHS, on a premium one-third acre lot overlooking the Disney preserve with a HEATED SALTWATER POOL AND SPA under a screen enclosure, this beautifully upgraded home is 4,500 square feet of understated elegance. With no front neighbor, step back to take in the impressive façade, paver drive and custom

  Andrew Martin RE/MAX TOWN CENTRE

  10139 Austrina Oak Loop, Winter Garden, FL 34787
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  /28

  $2,500,000

  • 4 Beds
  • 4.5 Baths
  • 4,961 Sq Ft

  13377 Lake Butler Blvd, Winter Garden, FL 34787

  Fantastic opportunity to purchase 12+ acres of private, quiet lake front property in Winter Garden/Windermere area on West Lake Butler Blvd. with 4+ acres high and dry and no HOA. Property currently boasts dock with electricity and boat lift on a skiable lake. There is an existing house that could be remodeled or torn down and start fresh. Home is 4961 square feet and built in 1990 with

  Dawn Briggs BLUE MAGNOLIA REALTY LLC

  13377 Lake Butler Blvd, Winter Garden, FL 34787
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  /21

  $67,000

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  16541 Menorca Dr Unit 1106, Winter Garden, FL 34787

  Welcome to your Florida dream home! This charming and budget-friendly 2-bedroom, 2-bathroom manufactured home is nestled in the beautiful and highly desirable Vista del Lago community in Winter Garden, FL. Priced at just $80,000! The home features a spacious master bedroom with an en suite bathroom, a cozy screened-in Florida room perfect for relaxing year-round, a carport, and a dedicated

  Samantha Rodriguez Sunset Home Sales

  16541 Menorca Dr Unit 1106, Winter Garden, FL 34787
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  /26

  $424,900

  • 3 Beds
  • 3 Baths
  • 1,717 Sq Ft

  10072 Memoir Ave, Winter Garden, FL 34787

  Lovely two-story townhome in the charming Storey Grove neighborhood in Winter Garden! Plenty of space in this 1717 sf home with detached garage. Spacious downstairs living areas with half bath and laundry. Upstairs features 2 full baths and the 3 bedrooms. Enjoy sitting outside in the fenced in patio area that connects the home to the garage. Neighborhood has a community pool, gym, Elementary

  Debi Bennefield ROCKFORD REALTY GROUP INC

  10072 Memoir Ave, Winter Garden, FL 34787
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  /39

  $849,000

  • 4 Beds
  • 3.5 Baths
  • 3,424 Sq Ft

  9870 Summerlake Groves St, Winter Garden, FL 34787

  Huge price improvement! Discover the perfect combination of comfort and convenience in this beautiful 2-story home, ideally situated in Winter Garden, one of Central Florida's most desirable neighborhoods, just a short drive from Orlando's renowned theme parks. Featuring 4 spacious bedrooms, 3.5 bathrooms, plus a game room that can be converted into a fifth bedroom! With an open-concept layout,

  Priscilla Triska FLORIDA CONNEXION PROPERTIES

  9870 Summerlake Groves St, Winter Garden, FL 34787
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  /57

  $2,699,000

  • 5 Beds
  • 6 Baths
  • 6,053 Sq Ft

  17726 Dangler Rd, Winter Garden, FL 34787

  Remarkable opportunity to own a sprawling equestrian-friendly privately gated estate with a newer custom-built 5-bedroom luxury home, detached 5-stall horse barn with studio apartment with kitchen, plus a separate 5-bay RV or car collector’s garage building – all on 5.11 acres within the Lake Avalon Rural Settlement. Escape from the hustle to a country retreat still minutes from Hamlin Town

  Rob Rahter STOCKWORTH REALTY GROUP

  17726 Dangler Rd, Winter Garden, FL 34787
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  /47

  $725,000

  • 5 Beds
  • 3 Baths
  • 3,048 Sq Ft

  563 Copperdale Ave, Winter Garden, FL 34787

  One or more photos have been virtually staged. $25,000 below appraised value! Seller offering an additional $7000 towards rate buy-down or closing costs. This 5-bedroom, 3-bathroom, lovely pool home is ready for a new family to make lasting memories! Upon arriving at this wonderful home, you will be welcomed by the gorgeous pavers in the driveway and tall, pristine palms. When entering the home,

  Michelle Richardson KELLER WILLIAMS CLASSIC

  563 Copperdale Ave, Winter Garden, FL 34787
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  /51

  $775,000

  • 5 Beds
  • 3 Baths
  • 3,082 Sq Ft

  13722 Fox Glove St, Winter Garden, FL 34787

  UPDATED WITH NEW BEAUTIFUL LAMINATE FLOORING IN MAIN AREAS!!! Welcome to this stunning 5 Bed, 3 Bath *POOL* home located on the 14TH HOLE in the esteemed community of Stoneybrook West in Winter Garden! Offering more than 3,000 square feet of living space, this residence combines elegance with functionality. You’ll be greeted by beautiful landscaping with stone accent columns as you walk up the

  NASTASSJA TOOMBS DENIZ REALTY PARTNERS LLC

  13722 Fox Glove St, Winter Garden, FL 34787
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  /60

  $887,000

  • 4 Beds
  • 3.5 Baths
  • 3,427 Sq Ft

  14645 Scott Key Dr, Winter Garden, FL 34787

  PRICE REDUCED...Welcome to Watermark built by Meritage homes, a luxury resort style community which includes a water park-style pool for the family, multiple tennis courts, and an exclusive fitness center. There are two clubhouses with balconies where you can see the nightly fireworks from Disney World. This very well maintained home has 4 bedrooms, 3.5 bathrooms. The living room leads into a

  Arlete Ritt WRA BUSINESS & REAL ESTATE

  14645 Scott Key Dr, Winter Garden, FL 34787
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  /83

  $3,380,000

  • 5 Beds
  • 5.5 Baths
  • 5,116 Sq Ft

  14544 Avenue of the Rushes, Winter Garden, FL 34787

  Welcome to 14544 Ave of the Rushes - A Masterpiece of Waterfront Luxury in Winter Garden’s Premier Community! Being sold Turn-Key and fully furnished!Indulge in the pinnacle of luxury living with this breathtaking lakefront estate, perfectly positioned on the pristine shores of Lake Hancock within the coveted Signature Lakes community. Encompassing 1.18 acres of prime waterfront property,

  Carolina Mariano Da Silva PREMIER SOTHEBYS INT'L REALTY

  14544 Avenue of the Rushes, Winter Garden, FL 34787
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  /46

  $869,000

  • 4 Beds
  • 3.5 Baths
  • 2,799 Sq Ft

  15672 Shorebird Ln, Winter Garden, FL 34787

  Great New Price!!! Come enjoy the Lakeshore Lifestyle! This beautiful Toll Brothers Pool Home on a premium corner lot has great curb appeal with its Tuscan elevation, stonework, barrel tile roof and quality doors. From the moment you enter this 4-bedroom, 3.5-bath home with oversized 2-car garage, you notice the 9-10' ceiling height, crown moulding, and luxury features throughout. A perfect

  Karen Ledet EXP REALTY LLC

  15672 Shorebird Ln, Winter Garden, FL 34787
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  /43

  $1,199,999 Open Sun 12PM - 3PM

  • 5 Beds
  • 4.5 Baths
  • 3,881 Sq Ft

  15732 Shorebird Ln, Winter Garden, FL 34787

  YOUR FLORIDA DREAM HOME AWAITS! ANOTHER PRICE IMPROVEMENT! LUXURY POOL HOME WITH ALL THE UPGRADES AND MORE! LIKE-NEW CONDITION! This fabulous Madeira model by Toll Brothers has all the builder upgrades and many, many more added by the seller. Situated on a larger, corner lot and beautifully landscaped, the curb appeal alone is worth a visit. With just under 3900 sf, the home provides 5 bedrooms

  Karen Ledet EXP REALTY LLC

  15732 Shorebird Ln, Winter Garden, FL 34787
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  /54

  $1,200,000

  • 5 Beds
  • 3.5 Baths
  • 3,911 Sq Ft

  10219 Atwater Bay Dr, Winter Garden, FL 34787

  Welcome to this stunning lakefront pool home in the highly sought after Waterleigh community of Winter Garden. Overlooking Hickorynut Lake, this home is designed for both comfort and luxury. Boasting five bedrooms and three and a half baths, it offers an exceptional blend of modern elegance and functional living space. With an open concept layout, high ceilings, and plantation shutters

  Chris Creegan CREEGAN GROUP

  10219 Atwater Bay Dr, Winter Garden, FL 34787
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  /50

  $2,950,000

  • 9 Beds
  • 6 Baths
  • 7,505 Sq Ft

  4230 Rex Dr, Winter Garden, FL 34787

  **A RARE OPPORTUNITY YOU WON’T WANT TO MISS!!** 9.75 PRIME ACRES IN THE HEART OF WINTER GARDEN ~ MAIN HOME CUSTOM BUILT BY HANNIGAN HOMES 5BD/4BA/3-CAR- 5,423 SQFT, INCLUDING AN ABOVE GARAGE APARTMENT WITH 1/BD/1/BA/+KITCHENETTE ~ SECOND HOME ON PROPERTY INCLUDES 4BD/2BA/2-CAR - 2,082SQFT ~ 10-STALL + TACKROOM HORSE BARN - 2,592 SQFT, 3 PASTURES ~ FENCED IN RIDING RING AND MUCH MORE! This

  Jennifer Wemert WEMERT GROUP REALTY LLC

  4230 Rex Dr, Winter Garden, FL 34787
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  /30

  $85,000

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft

  935 Hyde Park Cir Unit 129, Winter Garden, FL 34787

  Welcome home to 935 Hyde Park Cir. #129 located in Winter Garden's 55+ Hyde Park Village near shopping, restaurants and Downtown Winter Garden. This adorable residence features an oversized Primary bedroom with updated ensuite bathroom offering a new tiled walk-in shower and gorgeous new vanity. This well designed home has an open layout with updated LVP flooring throughout the home, with the

  Rachel Rivera Re/max Premier Realty

  935 Hyde Park Cir Unit 129, Winter Garden, FL 34787
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  /33

  $709,000

  • 4 Beds
  • 2.5 Baths
  • 1,579 Sq Ft

  322 Apopka St, Winter Garden, FL 34787

  ***OPPORTUNITY KNOCKS*** Come see this STUNNING 4-bedroom 2.5-bathroom POOL HOME nestled in the heart of the HISTORIC DISTRICT of Winter Garden, Florida. With sleek lines, large windows and minimalist design, the home embodies CLASSIC MID-CENTURY ARCHITECHTURE while offering all of the modern conveniences. The open floor plan connects the kitchen to living room with an amazing dining area

  Jim Kernohan SOUTHERN HERITAGE REALTY, INC

  322 Apopka St, Winter Garden, FL 34787
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  /40

  $699,800

  • 4 Beds
  • 3 Baths
  • 3,359 Sq Ft

  15543 Pebble Ridge St, Winter Garden, FL 34787

  Popular Stoneybrook West Subdivision - A gated golf community with 2255 homes. 2 Story, 4 Bedrooms, 3 Full Baths. Master is upstairs, huge bedroom, with walk in closet and master bath. A large 27x24 Bonus room over 3 Car Garage. One bedroom with guest bath downstairs also LR, DR, FR, Kitchen and Laundry. Off the master bedroom is a 12x22 Deck overlooking the screened pool and golf course. Nice

  Paul McGarigal RE/MAX SELECT GROUP

  15543 Pebble Ridge St, Winter Garden, FL 34787
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  /40

  $950,000

  • 5 Beds
  • 4 Baths
  • 3,152 Sq Ft

  515 N Boyd St, Winter Garden, FL 34787

  One or more photo(s) has been virtually staged. Discover the charm and convenience of luxurious living in this stunning 5-bedroom, 3-bathroom home, perfectly located in the heart of downtown Winter Garden. With a spacious and thoughtfully designed layout, this residence offers a blend of elegance and comfort ideal for families and guests alike. Here’s what makes this home exceptional:As you

  Erica Diaz HOMEVEST REALTY

  515 N Boyd St, Winter Garden, FL 34787
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  /29

  $570,000

  • 4 Beds
  • 2.5 Baths
  • 2,754 Sq Ft

  1134 Harbor Hill St, Winter Garden, FL 34787

  Seller offering $10,000 towards the buyers closing costs. For a complete REAL walk through of this home find the Video or Virtual Tour button somewhere on this page! Welcome to this magnificent two-story, four four-bedroom, two-and-a-half-bath pool Home located in the highly sought-after guard gate golf community of Stoneybrook West. As you enter the Home, you will be greeted with high ceilings &

  Bobby Christiano COLDWELL BANKER RESIDENTIAL RE

  1134 Harbor Hill St, Winter Garden, FL 34787
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  /88

  $2,000,000

  • 5 Beds
  • 6 Baths
  • 4,329 Sq Ft

  15680 Panther Lake Dr, Winter Garden, FL 34787

  Prepare to be awed by this stunning estate from the Toll Brothers executive collection in the renowned community of Lakeshore Preserve. This home presents an ultra modern layout bringing you an environment that caters to both entertaining and every day life. The first floor is open and has 2 sets of triple pane sliding glass doors that fully open to your personal oasis. Beyond the covered lanai

  Christina Cannon KELLER WILLIAMS CLASSIC

  15680 Panther Lake Dr, Winter Garden, FL 34787
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  /28

  $850,000

  • 3 Beds
  • 2.5 Baths
  • 2,163 Sq Ft

  430 Courtlea Oaks Blvd, Winter Garden, FL 34787

  Nestled at the rear of Courtlea Oaks, discover this hidden gem positioned on a corner lot in the Golf Cart District of Winter Garden, just blocks away from all the downtown activities. This residence boasts 3 bedrooms, 2.5 bathrooms, a spacious grand foyer entrance, a den, a fireplace, and a screened-in pool! In the Florida heat, having a pool is almost a necessity, and look no further—this home

  Haleigh Clark OPTIMA ONE REALTY, INC.

  430 Courtlea Oaks Blvd, Winter Garden, FL 34787
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  /98

  $845,000

  • 7 Beds
  • 4 Baths
  • 4,704 Sq Ft

  17987 Gourd Neck Loop, Winter Garden, FL 34787

  Price Reduced to Sell!!! Welcome to the Verde Park, a stunning home nestled in the heart of Winter Garden, FL. This home is a perfect blend of style, comfort, and convenience, offering a spacious kitchen complete with a walk-in pantry, granite countertops, custom tile backsplash, and stainless steel appliances. The extensive counter space and cozy breakfast nook open up to a warm and inviting

  Gilbert Rivera GR REALTY EXPERTS

  17987 Gourd Neck Loop, Winter Garden, FL 34787
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  /65

  $1,949,000 Open Sat 1AM - 4PM

  • 5 Beds
  • 4.5 Baths
  • 4,274 Sq Ft

  1020 Tildenville School Rd, Winter Garden, FL 34787

  Step into luxury with this brand-new, custom-built J&J home! Featuring 5 spacious bedrooms, 4.5 baths, plus a loft and flex space, this home is designed for both comfort and style. GREEN certified home. The primary bedroom and two additional bedrooms are conveniently located on the main floor, offering easy living. Chef's kitchen with monogram appliances and a scullery kitchen complete with

  Kara Manuchia ALL REAL ESTATE & INVESTMENTS

  1020 Tildenville School Rd, Winter Garden, FL 34787
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  /46

  $1,895,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 4,088 Sq Ft

  958 Tildenville School Rd, Winter Garden, FL 34787

  Exquisite New Construction in the Heart of Winter Garden’s Golf Cart District – Over 4,000 Sq Ft of Craftsman Charm!Step into timeless style and modern luxury with this brand new Craftsman-style masterpiece, perfectly situated on a charming cobblestone one-way street in the highly sought-after Golf Cart District of historic Winter Garden. Boasting over 4,000 square feet of beautifully

  Amy Miller ALL REAL ESTATE & INVESTMENTS

  958 Tildenville School Rd, Winter Garden, FL 34787
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  /45

  $1,825,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,425 Sq Ft

  502 Winter Garden Vineland Rd Unit R, Winter Garden, FL 34787

  Fantastic New Construction Custom Home in Winter Garden, one of Central Florida’s most sought-after locations. Step into a world of excellence in this single story modern masterpiece. With soaring ceilings and high-end finishes throughout this home is sure to appeal to a wide range of buyers. With over 4420 square feet of conditioned living space on a half-acre lot there is ample room for

  Paul Hickey FLORIDA GOLD REAL ESTATE LLC

  502 Winter Garden Vineland Rd Unit R, Winter Garden, FL 34787
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  /9

  $5,995,000 New Construction

  • 5 Beds
  • 6 Baths
  • 6,000 Sq Ft

  13377 Lake Butler Blvd, Winter Garden, FL 34787

  Pre-Construction. To be built. To be Built, Rendering provided by master custom home builder, David Konkol of Konkol Custom Homes. However, buyer can work with builder to build any design buyer prefers (pricing to adjust accordingly). The property is spectacular waterfront acreage with boat dock on boatable, skiable Lake Roper. Acreage is 12.4 +/- with some conservation. Zoned A-1 (agricultural

  Dawn Briggs BLUE MAGNOLIA REALTY LLC

  13377 Lake Butler Blvd, Winter Garden, FL 34787
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  /15

  $2,295,000 New Construction

  • 6 Beds
  • 5.5 Baths
  • 4,859 Sq Ft

  1244 Water Maple Dr, Oakland, FL 34787

  Pre-Construction. To be built. Introducing the Hamlin model by Element Home Builders—a stunning 4,859 square-foot residence designed for luxurious living and modern comfort. With 6 spacious bedrooms and 5.5 beautifully appointed bathrooms, this home offers ample space for families of all sizes and lifestyles.Step inside and experience an open-concept layout that combines elegance with

  Alexis Anderson REGENCY REAL ESTATE LLC

  1244 Water Maple Dr, Oakland, FL 34787
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  /15

  $2,175,000 New Construction

  • 5 Beds
  • 8 Baths
  • 4,433 Sq Ft

  1232 Water Maple Dr, Oakland, FL 34787

  Pre-Construction. To be built. Presenting the Citrus plan by Element Home Builders—a spacious home designed for modern living. With 5 bedrooms and 5 bathrooms, and 3 powder bathrooms, this expansive layout provides the perfect combination of comfort, style, and functionality. Every inch of this home is thoughtfully designed to create ample space for both private retreats and vibrant social

  Alexis Anderson REGENCY REAL ESTATE LLC

  1232 Water Maple Dr, Oakland, FL 34787
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  /15

  $2,150,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,388 Sq Ft

  1238 Water Maple Dr, Oakland, FL 34787

  Pre-Construction. To be built. Welcome to the Blossom home plan by Element Home Builders, where elegance meets functionality in a spacious, open layout. Boasting soaring ceilings and an expansive 12-foot kitchen island with abundant storage, this home is designed for both family living and entertaining. Enjoy seamless transitions between the gourmet kitchen, dining, and living areas, perfect for

  Heather Spirazza REGENCY REAL ESTATE LLC

  1238 Water Maple Dr, Oakland, FL 34787

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