34

4-Bedroom Houses for Sale in Winter Garden, FL with Private Pool

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  • /49

    $720,000

    • 4 Beds
    • 2.5 Baths
    • 2,617 Sq Ft

    2454 Black Lake Blvd, Winter Garden, FL 34787

    Elegant Pool Home in Exclusive Stoneybrook West Guard-Gated Golf CommunityEnjoy privacy and tranquility in this spacious 4-bedroom, 2.5-bath home with a 3-car garage, set on a serene pond for ultimate privacy. From the moment you enter, you'll appreciate the formal living and dining spaces, ideal for sophisticated entertaining. The gourmet kitchen opens seamlessly to a spacious family room

    Agent Photo

    Kristi Matthew

    CENTURY 21 CARIOTI

    (321) 336-7340

    2454 Black Lake Blvd, Winter Garden, FL 34787
  • /47

    $1,282,000

    • 4 Beds
    • 3 Baths
    • 2,517 Sq Ft

    11400 Lovers Ln, Winter Garden, FL 34787

    If you've ever dreamed of country living, but don't want to give up your conveniences, then welcome to your DREAM property in desirable Winter Garden! This spacious 2,571 sq ft custom home sits on 4.6 acres and includes a 3 stall horse barn with a tack room, as well as an additional 10x20 garage. The home has so much natural light and views out of every window. The kitchen has been recently

    Agent Photo

    Brad Bolton

    LPT REALTY, LLC

    (321) 353-8727

    11400 Lovers Ln, Winter Garden, FL 34787
  • /51

    $1,689,000

    • 4 Beds
    • 3.5 Baths
    • 4,000 Sq Ft

    15264 Shonan Gold Dr, Winter Garden, FL 34787

    BEAUTIFULLY APPOINTED LAKEVIEW ESTATE HOME! Welcome to this exceptional two-story "Courbet" model located in the highly sought-after Overlook at Hamlin community in Winter Garden. Built in 2017, this expansive residence offers over 4,000 square feet of beautifully designed living space. Featuring four spacious bedrooms, three and a half baths, and two versatile dens—one on each floor—this home is

    Michael Julian JULIAN PROPERTIES, INC.

    15264 Shonan Gold Dr, Winter Garden, FL 34787
  • /31

    $2,195,000

    • 4 Beds
    • 4 Baths
    • 3,616 Sq Ft

    15198 E Oakland Ave, Winter Garden, FL 34787

    Price reduction! Welcome to this stunning farmhouse-style home nestled on a premium corner lot in one of the most sought-after communities near Historic Winter Garden. Thoughtfully designed and beautifully maintained, this home offers modern comfort with timeless charm. This is part of one of only 17 exclusive oversized luxury custom residences. Set in a thriving, close-knit neighborhood the area

    Melody Niederst IAD FLORIDA LLC

    15198 E Oakland Ave, Winter Garden, FL 34787
  • /49

    $1,150,000

    • 4 Beds
    • 3 Baths
    • 2,464 Sq Ft

    14048 Larkspur Lake Dr, Winter Garden, FL 34787

    Welcome to 14048 Larkspur Lake Drive, where lakefront living meets modern design on a sprawling 1.34-acre homesite with 98 feet of private shoreline on Lake Huckleberry. With water rights included, you have the opportunity to build your own dock and fully embrace the waterfront lifestyle. From the moment you arrive, the expansive backyard invites you to relax and unwind. Enjoy tranquil lake views

    Brad Young HOMEVEST REALTY

    14048 Larkspur Lake Dr, Winter Garden, FL 34787
  • /49

    $859,000

    • 4 Beds
    • 3.5 Baths
    • 2,935 Sq Ft

    15079 Guava Bay Dr, Winter Garden, FL 34787

    Introducing a breathtaking Spanish-Mediterranean style pool home, built in 2020 and perfectly situated on a premium corner lot in the highly desirable Watermark community of Horizon West. This thoughtfully designed home blends elegance with functionality, featuring timeless finishes, a bright open-concept layout, and luxury vinyl plank flooring throughout the main living areas. Offering 4

    Diana Leon LPT REALTY, LLC

    15079 Guava Bay Dr, Winter Garden, FL 34787
  • /13

    $1,200,000

    • 4 Beds
    • 3 Baths
    • 2,986 Sq Ft

    16071 Barkly Ridge Ct, Winter Garden, FL 34787

    Enchanting house newly settled in Avalon Ridge, with a private pool-located in one of Winter Garden's most desired areas.This residence has been carefully designed and has 4 bedrooms with carpet, 3 complete bathrooms and a perfect combination of modern space, functionality and finishes. The living room has sliding doors that open to the outside with a private pool, creating an ideal

    Jennifer Olmeda WRA BUSINESS & REAL ESTATE

    16071 Barkly Ridge Ct, Winter Garden, FL 34787
  • /52

    $895,000

    • 4 Beds
    • 3 Baths
    • 2,933 Sq Ft

    657 Duff Dr, Winter Garden, FL 34787

    Welcome to 657 Duff Dr—a spacious and beautifully upgraded pool home located in Glynwood, one of Winter Garden’s most desirable neighborhoods. With over 2,000 square feet of living space, a split floor plan, and soaring high ceilings, this home offers the perfect blend of comfort, privacy, and modern design.Step inside to find luxury vinyl plank (LVP) flooring throughout, giving the home

    Abby Greenberg COMPASS FLORIDA LLC

    657 Duff Dr, Winter Garden, FL 34787
  • /54

    $895,000

    • 4 Beds
    • 4 Baths
    • 3,940 Sq Ft

    1331 Marble Crest Way, Winter Garden, FL 34787

    Stunning Golf-Front Arthur Rutenberg Semi-Custom Home in Guard-Gated Stoneybrook West.Live the Florida lifestyle in this beautifully appointed luxury pool home overlooking the golf course in the exclusive, guard-gated community of Stoneybrook West. This spacious and light-filled home offers 4 bedrooms, a private office, and a large upstairs bonus room with full bath—ideal for a guest

    Robert Schott TEAMCONNECT REALTY LLC

    1331 Marble Crest Way, Winter Garden, FL 34787
  • /60

    $1,048,900

    • 4 Beds
    • 2.5 Baths
    • 2,442 Sq Ft

    859 Easley Ave, Winter Garden, FL 34787

    Rare opportunity to purchase a gorgeous move-in ready pool home in Winter Garden’s most desired community of Oakland Park. This 4 bedroom, 2 1⁄2 bath home with office/flex room space boasts a custom gourmet kitchen with 48” double oven gas range, custom hood range, brick wall backsplash and huge island for gathering. In the office/flex space which is separated from the living area by glass French

    Debbie Harris OAK AVENUE REAL ESTATE LLC

    859 Easley Ave, Winter Garden, FL 34787
  • /78

    $925,000

    • 4 Beds
    • 4 Baths
    • 3,881 Sq Ft

    724 Duff Dr, Winter Garden, FL 34787

    MODEL PERFECT & MOVE IN READY San Remo V floor plan from MI Homes in Winter Garden’s desirable gated Glynwood neighborhood! The home features 4 beds, 4 baths, an office with built-in shelving and wood floors, formal living and dining rooms, a bonus room, theatre room, plantation shutters, a newer roof (2019), covered patio, screened in saltwater pool & spa in a fenced in yard! You will love the

    Eve Metlis WATSON REALTY CORP

    724 Duff Dr, Winter Garden, FL 34787
  • /46

    $875,000

    • 4 Beds
    • 3 Baths
    • 2,662 Sq Ft

    14711 Winter Stay Dr, Winter Garden, FL 34787

    This stunning 4-bedroom, 3-bathroom home in Panther View offers the perfect blend of comfort and elegance. With an open-concept design, the space is filled with natural light, creating an inviting atmosphere for entertaining guests and making unforgettable family memories.The chef’s kitchen features quartz countertops, a stylish backsplash, stainless steel appliances, and 42-inch cabinets for

    GLAUCO POCHINE THE FLORIDA LOUNGE REALTY LLC

    14711 Winter Stay Dr, Winter Garden, FL 34787
  • /39

    $890,000

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

    9870 Summerlake Groves St, Winter Garden, FL 34787

    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, this home provides the

    Priscilla Triska FLORIDA CONNEXION PROPERTIES

    9870 Summerlake Groves St, Winter Garden, FL 34787
  • /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
  • /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
  • /70

    $999,000

    • 4 Beds
    • 2.5 Baths
    • 2,751 Sq Ft

    526 First Cape Coral Dr, Winter Garden, FL 34787

    Welcome to your dream home—a stunningly renovated property that perfectly blends luxury, comfort, and modern design. Located in the highly desirable Cape Coral area, this exceptional residence offers an unparalleled lifestyle, with thoughtfully designed indoor and outdoor spaces to meet the needs of the most discerning buyer.Property DetailsBedrooms: 4 generously sized bedrooms,

    Daniel Vilela JOHN SILVA REALTY & ASSOCIATES

    526 First Cape Coral Dr, Winter Garden, FL 34787
  • /92

    $2,750,000

    • 4 Beds
    • 4.5 Baths
    • 4,886 Sq Ft

    9201 Tower Pine Dr, Winter Garden, FL 34787

    Fabulous private location with 5 beautiful acres and gated entry - Bring your horses! ** 2538sf horse barn with 4 stalls, tack room and 2nd room that could also be used as a tack room ** Nelson automatic horse waterers included ** Horse corral and 1 pasture/paddock that could be divided into 2 ** Additional 1800sf pole barn ** Home, barn and 1800sf pole barn and casita all 2019 BUILT ** 1800sf

    Andrew Philippone INDEPENDENCE REALTY GROUP LLC

    9201 Tower Pine Dr, Winter Garden, FL 34787
  • /55

    $780,000

    • 4 Beds
    • 3 Baths
    • 3,346 Sq Ft

    2223 Wintermere Pointe Dr, Winter Garden, FL 34787

    Spacious Corner Lot Home in Gated Community with Pool and Bonus Rooms!Welcome to your dream home! This beautifully maintained 4-bedroom, 3-bathroom residence offers plenty of space and flexibility, including 3 additional bonus rooms perfect for a home office, gym, media room, or guest space.Located on a desirable corner lot in a secure gated community, this home combines privacy,

    Maria Franco EPIC REALTY

    2223 Wintermere Pointe Dr, Winter Garden, FL 34787
  • /47

    $635,000

    • 4 Beds
    • 3 Baths
    • 2,070 Sq Ft

    3227 Buoy Cir, Winter Garden, FL 34787

    Welcome to this MOVE-IN READY one-story 4 bed/3 Bath home in Winter Garden, Florida. This Pulte built, Canopy Model, completed in 2020, has an ideal OPEN FLOOR PLAN you've been searching for! Uponentering you are welcomed with RECENTLY UPDATED marble tile flooring and FRESHLY PAINTED walls in the main living areas. The first of your FOUR bedrooms, also a Wheelchair Accessible room, is located

    Tara Pintor CLOCK TOWER REALTY

    3227 Buoy Cir, Winter Garden, FL 34787
  • /68

    $699,999

    • 4 Beds
    • 3 Baths
    • 2,072 Sq Ft

    15071 Guava Bay Dr, Winter Garden, FL 34787

    Immaculate 4/3 POOL HOME on a premium lot in highly sought after Horizon West. Beautifully cared-for one story is being offered by its original owners. Situated in the desirable community of Watermark, this home offers the perfect blend of luxury, comfort, and convenience. Enter through the inviting front porch to your Concrete Block One-Story home with 10-FT Ceilings. The gourmet kitchen is a

    Alin Zdroba PROPERTIO

    15071 Guava Bay Dr, Winter Garden, FL 34787
  • /51

    $620,000

    • 4 Beds
    • 2.5 Baths
    • 2,348 Sq Ft

    600 Egret Place Dr, Winter Garden, FL 34787

    **This property qualifies for a closing cost credit up to $9,300 through the Seller’s preferred lender.**Welcome to a beautifully maintained single-family home located in the heart of Winter Garden. This spacious 4-bedroom, 2.5-bath residence features a private screened-in pool, oversized 2-car garage, new Roof in 2025, new AC in 2022, with elegant design details throughout. From the moment you

    Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

    600 Egret Place Dr, Winter Garden, FL 34787
  • /41

    $750,000

    • 4 Beds
    • 3 Baths
    • 2,634 Sq Ft

    14117 Larkspur Lake Dr, Winter Garden, FL 34787

    Welcome to 14117 Larkspur Lake Drive, located at Lakeview Pointe. Closed to the Orange County National Golf Center, Winter Garden Village, restaurants, Closed to Disney a major road. Upgraded Scale residence, that perfectly combines modern comfort, energy efficiency, and resort-style living. This spacious 4-bedroom, 3-bathroom home is located in a sought-after neighborhood and offers

    Elizabeth Szalus COLDWELL BANKER RESIDENTIAL RE

    14117 Larkspur Lake Dr, Winter Garden, FL 34787
  • /71

    $1,500,000

    • 4 Beds
    • 4 Baths
    • 4,212 Sq Ft

    108 Stanton Estates Cir, Winter Garden, FL 34787

    Welcome to 108 Stanton Estates Circle, a beautifully crafted 4-bedroom, 4-bath pool home offering over 4,200 square feet of refined living in the heart of one of Winter Garden’s most charming communities. Located in Stanton Estates, a quiet neighborhood of fewer than 50 homes, this property sits just one block from the West Orange Trail and within Winter Garden’s golf cart district, offering

    Silvia Kinkela SERHANT

    108 Stanton Estates Cir, Winter Garden, FL 34787
  • /50

    $1,275,000

    • 4 Beds
    • 3.5 Baths
    • 4,000 Sq Ft

    5365 Bowman Dr, Winter Garden, FL 34787

    Nestled in the sought-after Overlook II at Hamlin community, this meticulously upgraded 4-bedroom, 3.5-bathroom Taylor Morrison home offers luxurious living space. Built in 2015, it has been thoughtfully enhanced with high-end finishes and modern conveniences. Step into your private oasis featuring a heated, screened-in pool with a swim-up table, perfect for relaxation and entertaining. The

    Will Skinner FORTERA REALTY LLC

    5365 Bowman Dr, Winter Garden, FL 34787
  • /46

    $725,000

    • 4 Beds
    • 3.5 Baths
    • 2,557 Sq Ft

    8256 Bayview Crossing Dr, Winter Garden, FL 34787

    WATERLEIGH POOL HOME! One of Winter Garden's most desirable communities with AWARD WINNING LUXURY AMENITIES. This Corner Lot Home is nestled on a quiet tree-lined street with no through traffic providing a safe space for children. Remarkable Renovation offers over 2550 Square Feet of living area with 4 bedrooms, 3 full bathrooms plus one Half Bathroom. Well thought out floor plan with a Large

    Thad Czapka COLDWELL BANKER RESIDENTIAL RE

    8256 Bayview Crossing Dr, Winter Garden, FL 34787
  • /50

    $525,000

    • 4 Beds
    • 2 Baths
    • 1,992 Sq Ft

    714 Home Grove Dr, Winter Garden, FL 34787

    ***MAJOR PRICE IMPROVEMENT-LOCATION, LOCATION ***This home offers unparalleled comfort and style. The property is part of the desirable Regency Oaks Community, where residents enjoy access to resort-style living that owns a generous resort-style pool, tennis courts, a serene pond, a private park, a playground, and sidewalks just steps from the home. The main living room includes an open and

    Arturo Castillo PREFERRED REAL ESTATE BROKERS

    714 Home Grove Dr, Winter Garden, FL 34787
  • /29

    $824,000

    • 4 Beds
    • 3.5 Baths
    • 2,935 Sq Ft

    9917 Summerlake Groves St, Winter Garden, FL 34787

    Beautiful 2-story home in desirable Winter Garden, featuring 4 bedrooms, 3.5 bathrooms, a bonus room, and a private pool. The flexible bonus room can easily be converted into a 5th bedroom or used as a game/media room. Enjoy an open-concept layout with a spacious kitchen, ample counter space, and a cozy breakfast nook flowing into the bright family room.The expansive primary suite offers

    Eduardo Pavone ON ME REALTY

    9917 Summerlake Groves St, Winter Garden, FL 34787
  • /48

    $725,000

    • 4 Beds
    • 3 Baths
    • 3,571 Sq Ft

    12411 Scarlett Sage Ct, Winter Garden, FL 34787

    **WINTER GARDEN DREAM HOME ALERT** **GATED COMMUNITY** **OVER 3,500 SQFT** **1/4 ACRE LOT + CUL-DE-SAC** **PAID OFF WHOLE HOME SOLAR SYSTEM -- NO LOAN OR LEASE TO ASSUME -- $35 PER MONTH ELECTRIC BILL** **PRIVATE SCREENED POOL & SPA** **FOUR BEDROOMS + THREE FULL BATHS + TWO LARGE OFFICE/DEN SPACES + HUGE 2ND STORY LOFT** **600+ SQFT THREE-CAR GARAGE (21x29)** **WOOD BURNING FIREPLACE**

    Tara Moore TARA MOORE REAL ESTATE

    12411 Scarlett Sage Ct, Winter Garden, FL 34787
  • /50

    $597,900

    • 4 Beds
    • 3 Baths
    • 2,455 Sq Ft

    2019 Wintermere Pointe Dr, Winter Garden, FL 34787

    Open for offers on website. Welcome home to Winter Garden's gated Wintermere Pointe. This 4 Bedroom 3 bath home boasts a generous lot and ample setbacks from neighbors that is less common in sought after Winter Garden. Spacious split plan with well appointed screen enclosed pool & spa as a focal point. No rear neighbors and a tree shaded rear yard make this screen enclosed pool and spa a private

    Patrick D'Agostino GLORY INTL. REAL ESTATE CO

    2019 Wintermere Pointe Dr, Winter Garden, FL 34787
  • /48

    $699,999

    • 4 Beds
    • 2.5 Baths
    • 2,873 Sq Ft

    459 Millwood Place, Winter Garden, FL 34787

    One or more photo(s) has been virtually staged. Just in Time for Summer – A Self-Sustaining Paradise with Solar, Pool, Garden & More!Step into a home that offers not just warmth and comfort, but a lifestyle of sustainability and serenity. This impeccable four-bedroom, two-and-a-half-bath, and 3 car garage residence is nestled in a lush oasis bursting with fruit trees and designed for

    Erica Diaz HOMEVEST REALTY

    459 Millwood Place, Winter Garden, FL 34787
  • /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
  • /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
  • /40

    $709,800

    • 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
  • /29

    $595,000

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

    1134 Harbor Hill St, Winter Garden, FL 34787

    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 & natural light and an open feel. The formal living/dining

    Bobby Christiano COLDWELL BANKER RESIDENTIAL RE

    1134 Harbor Hill St, Winter Garden, FL 34787

Home Trends in Winter Garden, FL

Housing Trends

Median Sale Price
$550,000
Median Single Family Sale Price
$638,405
Median Townhouse Sale Price
$430,000
Median 2 Bedroom Sale Price
$220,000
Average Price Per Sq Ft
$267
Number of Homes for Sale
222
Last 12 months Home Sales
1,830
Months of Supply
1.50
Median List Price
$575,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
-7%
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