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Winter Garden, FL Homes for Sale with Pool

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  • /41

    $669,000

    • 4 Beds
    • 3 Baths
    • 2,117 Sq Ft

    9723 Lost Creek Dr, Winter Garden, FL 34787

    Beautiful 4-bedroom, 3 bath water view home in Waterleigh, Horizon West’s Premier Community! Welcome to your next chapter in Waterleigh, where resort-style amenities and thoughtful design come together in one of Horizon West’s most desirable neighborhoods. This impeccably maintained 4-bedroom, 3-bath home offers 2,117 sq. ft. of single-story comfort, ideal for families, first-time buyers, or

    Ping Ma

    CHARLES RUTENBERG REALTY ORLANDO

    (321) 478-2658

    9723 Lost Creek Dr, Winter Garden, FL 34787
  • /76

    $2,950,000

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

    17737 Deer Isle Cir, Winter Garden, FL 34787

    Experience over an acre of elevated direct sunset lakefront luxury living on the naturally spring-fed waters of John’s Lake. Offered publicly for the first time, this fully custom estate represents a rare convergence of beauty, privacy and enduring design. Nearly 5,000 square feet of interior living space unfold effortlessly into an additional 1,000 square feet of exceptionally well-appointed

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    Candace Cassidy

    PREMIER SOTHEBY'S INTL. REALTY

    (321) 241-3937

    17737 Deer Isle Cir, Winter Garden, FL 34787
  • /38

    $290,000

    • 3 Beds
    • 3 Baths
    • 1,544 Sq Ft

    14501 Grove Resort Ave Unit 3642, Winter Garden, FL 34787

    Luxury Condo for Sale at The Grove Resort & Water Park, Just 5 Minutes from Walt Disney World! 3 Bedrooms / 3 Bathrooms | Fully Furnished | Ideal 1031 Exchange Property Discover the height of vacation luxury in Orlando's newest and most exclusive community, The Grove Resort & Water Park. This spacious sixth-floor unit (#3642) features 3 bedrooms and 3 bathrooms, designed for comfort and style,

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    Jose Carnero

    URBAN REAL ESTATE US

    (321) 492-0594

    14501 Grove Resort Ave Unit 3642, Winter Garden, FL 34787
  • /57

    $819,000

    • 4 Beds
    • 3.5 Baths
    • 2,909 Sq Ft

    5211 Citrus Leaf Blvd, Winter Garden, FL 34787

    Welcome to this exceptional Barret floor plan in the exclusive Silverleaf Reserve by Meritage Homes, offering 4 spacious bedrooms, a versatile bonus room, a dedicated office, and an additional flex space currently used as a music room. Positioned on one of the best lots in the community, this home features stunning lake views, unmatched privacy, and a thoughtfully designed layout for both comfort

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    Tiago Fernandez PLLC

    MCO REALTY GROUP LLC

    (321) 677-7036

    5211 Citrus Leaf Blvd, Winter Garden, FL 34787
  • /55

    $1,799,000

    • 5 Beds
    • 4.5 Baths
    • 4,300 Sq Ft

    15606 Shorebird Ln, Winter Garden, FL 34787

    Located in the sought-after Lakeshore Preserve community of Winter Garden, this 5-bedroom, 4.5-bath, 4,300 sq ft luxury lake view home offers refined design and flexibility. The home features two primary suites, one on the main level and one upstairs, ideal for multigenerational living or hosting guests. From the moment you enter, refined finishes and an open layout set the tone, enhanced by a

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    Tiffany Pantozzi

    ALIGN REAL ESTATE LLC

    (321) 486-8329

    15606 Shorebird Ln, Winter Garden, FL 34787
  • /32

    $295,000

    • 3 Beds
    • 2 Baths
    • 1,453 Sq Ft

    330 Southern Pecan Cir Unit 204, Winter Garden, FL 34787

    Spacious 3-bedroom, 2-bath condo with an attractive traditional design and an open floor plan that makes daily living easy. The entry foyer with a closet is on the first floor, while all living spaces are located upstairs for added privacy. Features include built-in accents, a laundry room conveniently off the kitchen, and ceiling fans throughout. The community offers resort-style amenities

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    Kristi Matthew

    CENTURY 21 CARIOTI

    (321) 529-3491

    330 Southern Pecan Cir Unit 204, Winter Garden, FL 34787
  • /33

    $710,000

    • 5 Beds
    • 3.5 Baths
    • 2,868 Sq Ft

    4918 Wildwood Pointe Rd, Winter Garden, FL 34787

    Located in the highly sought-after community of Orchard Hills, this stunning home offers the epitome of Central Florida living. Orchard Hills is a community that attracts buyers from all walks of life, making it an ideal investment. This spacious, single-story residence boasts 5 bedrooms, 3 full bathrooms, and one half-bath, ready for you to move in. From the moment you step inside, you'll be

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    Carlos Hernandez Franquet

    AGENT TRUST REALTY CORPORATION

    (321) 328-4515

    4918 Wildwood Pointe Rd, Winter Garden, FL 34787
  • /37

    $224,000

    • 3 Beds
    • 2 Baths
    • 1,396 Sq Ft

    14501 Grove Resort Ave Unit 2438, Winter Garden, FL 34787

    AGENTS - PLEASE VIEW REALTOR REMARKS IN THE MLS. Perfect as a family getaway or a high-performing investment property, this beautifully designed fully furnished 3-bedroom, 2-bath condo is located in the luxurious Grove Resort & Water Park in Winter Garden, FL. Thoughtfully outfitted with every comfort, this turn-key home welcomes you with style and convenience. Enjoy resort-style living with

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    Rick Brown

    KELLER WILLIAMS ADVANTAGE 2 REALTY

    (321) 382-2706

    14501 Grove Resort Ave Unit 2438, Winter Garden, FL 34787
  • /45

    $425,000

    • 2 Beds
    • 2.5 Baths
    • 1,813 Sq Ft

    7231 Duxbury Ln, Winter Garden, FL 34787

    One or more photo(s) has been virtually staged. Live in the heart of Horizon West’s vibrant Hamlin area, just minutes from Disney, shopping, dining, and everyday conveniences, in this beautifully maintained 2016 townhome offering the perfect blend of location, layout, and lifestyle. Enjoy the Magic of Disney right from home with views of the Nightly Fireworks lighting up the sky. With 1,813

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    Denise Gregorie

    CLOCK TOWER REALTY

    (321) 392-6184

    7231 Duxbury Ln, Winter Garden, FL 34787
  • /53

    $1,075,000

    • 5 Beds
    • 6 Baths
    • 4,025 Sq Ft

    10472 Petrillo Way, Winter Garden, FL 34787

    Welcome to 10472 Petrillo Way in Winding Bay Preserve, one of Winter Garden’s most desirable communities in Horizon West. Built in 2022, this stunning K. Hovnanian Grayson Model sits on a premium corner lot with DISNEY FIREWORK VIEWS and the rare opportunity to watch Space Coast ROCKET LAUNCHES right from your front porch. This home offers 5 bedrooms, 6 bathrooms, a private office, loft, and

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    Alexis Bress

    EXP REALTY LLC

    (321) 346-4225

    10472 Petrillo Way, Winter Garden, FL 34787
  • /60

    $585,000

    • 3 Beds
    • 2.5 Baths
    • 2,119 Sq Ft

    15813 Sweet Lemon Way, Winter Garden, FL 34787

    Imagine saying, “we live on Sweet Lemon Way in the Highlands at Summer Lake Groves”! Just sounds happy! So much in a name, with over 240 days of sunshine per year in our beautiful state! Thanks to Disney, that includes 365 nights of fireworks too! This community, located in the center of Horizon West, has convenient access to “A” rated schools, restaurants, shops and a never-ending schedule of

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    Autumn Makin

    LAKEFIELD REALTY GROUP LLC

    (689) 329-1680

    15813 Sweet Lemon Way, Winter Garden, FL 34787
  • /61

    $525,000

    • 3 Beds
    • 2.5 Baths
    • 1,688 Sq Ft

    648 Orange Belt Loop, Winter Garden, FL 34787

    Welcome to your opportunity to own in one of the most desirable locations near downtown Winter Garden—just off iconic Plant Street. This beautiful 3-bedroom, 2.5-bath home offers nearly 1,700 square feet of thoughtfully designed living space in an unbeatable setting. Step inside to an expansive great room featuring stylish wood-look tile and an open-concept layout that seamlessly connects the

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    Milinda Knollinger

    CORCORAN CONNECT LLC

    (321) 381-3214

    648 Orange Belt Loop, Winter Garden, FL 34787
  • /44

    $517,500

    • 3 Beds
    • 2.5 Baths
    • 2,052 Sq Ft

    8915 Fountain Palm Aly, Winter Garden, FL 34787

    Welcome to effortless luxury living in highly sought-after Lakeshore Preserve, where resort-style amenities, natural gas convenience, and true maintenance-free living come together in one exceptional townhome. This beautifully designed 3-bedroom, 2.5-bath residence offers approximately 2,000 square feet of thoughtfully curated space that lives large, bright, and inviting. From the moment you step

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    Micaela Navarra

    M2M REALTY

    (689) 354-0542

    8915 Fountain Palm Aly, Winter Garden, FL 34787
  • /62

    $465,000

    • 3 Beds
    • 2.5 Baths
    • 1,725 Sq Ft

    8113 Red Stopper Ln, Winter Garden, FL 34787

    Perfectly positioned in the heart of Horizon West, 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 two car garage with an attached oversized patio to enjoy nightly views of the Disney fireworks. Move-in ready and thoughtfully upgraded with a newer HVAC system, this

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    Kassandra Lopez

    EXP REALTY LLC

    (321) 475-7518

    8113 Red Stopper Ln, Winter Garden, FL 34787
  • /40

    $289,500

    • 3 Beds
    • 2 Baths
    • 1,396 Sq Ft

    14501 Grove Resort Ave Unit 2334, Winter Garden, FL 34787

    Escape to your own luxurious, fully furnished condo-hotel residence at the prestigious Grove Resort & Water Park—just minutes from Walt Disney World. Designed for both personal enjoyment and investment, this exceptional unit offers the perfect combination of a turnkey vacation retreat and high-performing income asset. Located on the third floor of Condominium II, the sought-after Jasmine floor

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    Amy Moline

    EXP REALTY LLC

    (321) 343-3008

    14501 Grove Resort Ave Unit 2334, Winter Garden, FL 34787
  • /14

    $3,380,000

    • 5 Beds
    • 5 Baths
    • 5,290 Sq Ft

    14511 Isleview Dr, Winter Garden, FL 34787

    Get ready to be impressed by this exceptional lakefront residence at 14511 Isleview Dr in Winter Garden, fully renovated by the renowned Davila Homes. Set directly on the pristine shores of Lake Hancock, this luxury property offers breathtaking water views and a private dock, perfect for boating, sunset lounging, or embracing the ultimate Florida lifestyle. This thoughtfully designed home

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    Fernanda Negromonte

    NOVA REAL ESTATE SERVICES INC

    (321) 850-4161

    14511 Isleview Dr, Winter Garden, FL 34787
  • /36

    $270,000

    • 3 Beds
    • 3 Baths
    • 1,544 Sq Ft

    14501 Grove Resort Ave Unit 2527, Winter Garden, FL 34787

    Short Sale. Short Sale Opportunity – Fully Furnished 3BR/3BA Condo at The Grove Resort – Vacation Rental Only / No Full-Time ResidencyInvestor Alert! Rare opportunity to own a FULLY FURNISHED and equipped 3-bedroom, 3-bath condo in the sought-after The Grove Resort, one of Orlando’s top vacation-only condo-hotel communities, just minutes from Disney. Turnkey for immediate rental. Large

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    Nayane Seabra

    WRA BUSINESS & REAL ESTATE

    (321) 341-5486

    14501 Grove Resort Ave Unit 2527, Winter Garden, FL 34787
  • /37

    $499,000

    • 3 Beds
    • 2 Baths
    • 1,864 Sq Ft

    8118 Surf Bird St, Winter Garden, FL 34787

    One or more photo(s) has been virtually staged. Welcome to 8118 Surf Bird Street, a stunning spec home with premium upgrades, located in the highly desirable Summerlake community of Winter Garden. This beautifully maintained, move-in-ready single-family residence offers 3 spacious bedrooms, 2 bathrooms, a standout feature is the flex room, which provides versatile space that can easily serve as a

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    Juliana Garcia Moraes

    PRISTINE INTERNATIONAL REALTY LLC

    (321) 346-5222

    8118 Surf Bird St, Winter Garden, FL 34787
  • /25

    $332,500

    • 2 Beds
    • 2 Baths
    • 1,265 Sq Ft

    14501 Grove Resort Ave Unit 3205, Winter Garden, FL 34787

    Luxury vacation rental within The Grove Resort and Spa. Beautifully furnished with modern furniture and fixtures that make for a one-of-a-kind vacation property, this fully furnished 2-bedroom, 2-bath unit can sleep up to 8 people (room with1 king bed, room with 2 full beds and queen sleeper sofa) and has a gourmet kitchen with stainless steel appliances and quartz counters. The Grove Resort and

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    Jamie Ampel

    ALL SELLERS & BUYERS REALTY INC

    (321) 710-1042

    14501 Grove Resort Ave Unit 3205, Winter Garden, FL 34787
  • /30

    $519,000

    • 4 Beds
    • 3 Baths
    • 2,042 Sq Ft

    16105 Water Spring Blvd, Winter Garden, FL 34787

    Discover this immaculate 4-bedroom, 3-bath home in the beautiful Storey Grove community. Designed for family living, it offers bright and spacious interiors that flow seamlessly from the open-concept kitchen to the main living area. The master suite features a private bathroom and generous storage space, while the additional bedrooms are perfect for guests, or a home office. Outside, enjoy a

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    Yesenia Barrios

    URBAN-O REAL ESTATE SOLUTIONS

    (321) 346-5456

    16105 Water Spring Blvd, Winter Garden, FL 34787
  • /68

    $2,100,000

    • 5 Beds
    • 5 Baths
    • 4,365 Sq Ft

    2450 Dahlgren Way, Winter Garden, FL 34787

    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

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    Keegan Siegfried

    LPT REALTY, LLC

    (321) 252-6500

    2450 Dahlgren Way, Winter Garden, FL 34787
  • /9

    $299,000

    • 2 Beds
    • 2 Baths
    • 1,265 Sq Ft

    Unlisted Address

    Come One, Come All! This is perfect for a family or anyone looking to use as an investment home. This beautiful home comes with really thought-out details to make you feel right at home. The Community also offers TONS of recreational items to choose from: You can choose from relaxing at the spa, working out in one or both of the two fitness centers provided. 3 swimming pools with food and drink

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    Consuelo Vilar

    WELCOME HOME REALTY GROUP LLC

    (321) 386-1360

    Unlisted Address
  • /59

    $2,100,000

    • 4 Beds
    • 4.5 Baths
    • 3,185 Sq Ft

    1021 Temple Grove Place, Winter Garden, FL 34787

    LUXURY Lakefront Estate – Minutes from Historic Downtown Winter Garden! Experience elevated waterfront living in this beautiful 4-bedroom, 4.5-bath lakefront residence, ideally located just minutes from the heart of Winter Garden and the charm of Plant Street. Situated within the coveted golf cart zone near Historic Downtown, this property offers the rare combination of private lakefront serenity

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    Nicole Rader

    MAINFRAME REAL ESTATE

    (321) 486-8407

    1021 Temple Grove Place, Winter Garden, FL 34787
  • /58

    $786,000

    • 4 Beds
    • 3.5 Baths
    • 3,272 Sq Ft

    8901 Lakeshore Pointe Dr, Winter Garden, FL 34787

    Stunning ENZO model townhome by Toll Brothers designed living space in the highly sought after Lakeshore Preserve community, where elegance meets convenience. Located among luxury homes and premium surroundings, this executive style residence delivers an exceptional combination of location, floor plan, and upgrades. Built in 2017, this spacious townhome features 4 bedrooms and four full

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    Carmelo Nuccio

    RE/MAX EXCLUSIVE COLLECTION

    (321) 382-3371

    8901 Lakeshore Pointe Dr, Winter Garden, FL 34787
  • /44

    $425,000

    • 3 Beds
    • 3 Baths
    • 1,813 Sq Ft

    7333 Duxbury Ln, Winter Garden, FL 34787

    One or more photo(s) has been virtually staged. Welcome to upscale townhome living in the highly sought-after Lakeview Pointe community, located in the heart of Horizon West’s exciting Hamlin entertainment district just minutes from Disney, shopping, dining, and everyday conveniences. This impeccably maintained 3-bedroom, 3-full bath, move-in-ready 2017 townhome offers over 1,800 square feet of

    Ann Wargo UPSIDE REAL ESTATE INC

    7333 Duxbury Ln, Winter Garden, FL 34787
  • /11

    $513,990 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,803+ Sq Ft

    Baldwin Plan at Lake Star at Ovation - Avenue Collection, Winter Garden, FL 34787

    It’s love at first sight with this 1,602 square foot plan, offering 3 bedrooms, 2 1⁄2 baths, and an alley-loaded garage. Best of all this home is 100% Energy Star 3.1 certifies which means it will save you on the recurring utility costs of owning a home. Some of the energy saving features include Core Fill insulation in the block walls, R-38 ceiling insulation, Radiant Roof Barrier, Low-E double

    M/I Homes Builder
    12025 Encore at Ovation Way Unit 36481413, Winter Garden, FL 34787
  • /79

    $869,900

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

    15672 Shorebird Ln, Winter Garden, FL 34787

    One or more photo(s) has been virtually staged. Experience refined Florida living in this elegant Toll Brothers built residence, perfectly located on a premium corner homesite in the sought-after Lakeshore Preserve community. Distinguished by its Tuscan elevation, stone accents, and barrel tile roof, this 4-bedroom, 3.5-bath pool home offers timeless curb appeal and thoughtfully designed living

    Helen Thompson RE/MAX SELECT GROUP

    15672 Shorebird Ln, Winter Garden, FL 34787
  • /34

    $583,990 New Construction

    • 3 - 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft

    Suncrest II Plan at Osprey Ranch - 32'/40' Single Family, Winter Garden, FL 34787

    Open-concept kitchen with center island and oversized pantry. Spacious great room with access to covered lanai. Private home office or optional Extra Suite off foyer. Lavish primarysuite with tray ceiling and walk-in closet. Relaxing primary bath with dual sinks and seated shower. Convenient second story laundry in proximity to bedrooms. Optional bonus room over garage.

    K. Hovnanian Homes Builder
    15221 Blue Peacock Ln Unit 36494326, Winter Garden, FL 34787
  • /29

    $747,999 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,833 Sq Ft

    Pallazio II Plan at Esplanade at McKinnon Groves - 60' Lot, Winter Garden, FL 34787

    From breezy open spaces to private retreats, the Pallazio II floor plan is designed for effortless luxury. This 1-story home features 3 bedrooms, 3.5 bathrooms, a 3-car garage and 2,833 square feet. Head through the courtyard that leads to the front porch and into a sweeping foyer to find beautiful open-concept living spaces. A great room flows into formal and casual dining areas, a modern

    Taylor Morrison Builder
    17705 Sedona St Unit 39548786, Winter Garden, FL 34787
  • /19

    $735,990 New Construction

    • 3 - 5 Beds
    • 2.5 - 4.5 Baths
    • 2,791 Sq Ft

    Moseley II Plan at Northlake at Ovation - Traditional, Winter Garden, FL 34787

    The Moseley II is a thoughtfully designed two-story home with three bedrooms, two full bathrooms, one half bathroom, and a two-car garage. This plan features a dramatic two-story family room that creates a bright and open living space. The second-floor primary suite offers privacy and comfort, while additional flexible living areas provide room to relax or entertain. High ceilings, abundant

    Ashton Woods Builder
    17551 Lake Star Rd Unit 36476723, Winter Garden, FL 34787
  • /17

    $399,900

    • 2 Beds
    • 2 Baths
    • 1,265 Sq Ft

    14501 Grove Resort Ave Unit 1318, Winter Garden, FL 34787

    OWN this full POOL-VIEW condominium in the MAIN building!!! As you enter this 3rd floor two bedroom, two bathroom unit, an unobstructed view to the Springs Pool welcomes you in the Premier Tower or Building One. What an amazing view!!! In the evenings, you may enjoy Disney's fireworks from your balcony or bedrooms!!! The unit is located in Tower One, where you find the lobby, concierge,

    Carlos Selmo PORTAL ORLANDO REALTY, LLC

    14501 Grove Resort Ave Unit 1318, Winter Garden, FL 34787
  • /2

    $895,990 New Construction

    • 4 - 6 Beds
    • 3.5 Baths
    • 3,458 Sq Ft

    Superior Plan at Northlake at Ovation - Estate, Winter Garden, FL 34787

    The Superior is a two-story home offering four bedrooms, three full bathrooms, one half bathroom, and a three-car garage. This spacious plan features an open-concept kitchen and family room perfect for gatherings. The private second-floor primary suite includes a walk-in closet and luxurious bath, complemented by additional bedrooms, a versatile loft, and convenient laundry room. Modern finishes,

    Ashton Woods Builder
    17551 Lake Star Rd Unit 36646269, Winter Garden, FL 34787
  • /7

    $456,990 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,675 Sq Ft

    Walden II Plan at Northlake at Ovation - Townhomes, Winter Garden, FL 34787

    The Walden II is a two-story townhome offering three bedrooms, two full bathrooms, one half bathroom, and a two-car garage. The open-concept main floor connects the kitchen, dining, and family rooms, creating a bright and functional space. Upstairs, the private primary suite offers comfort and privacy, accompanied by two additional bedrooms and a conveniently located laundry room. Thoughtful

    Ashton Woods Builder
    17551 Lake Star Rd Unit 36470489, Winter Garden, FL 34787
  • /5

    $818,990 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,542 Sq Ft

    Erie Plan at Northlake at Ovation - Estate, Winter Garden, FL 34787

    The Erie is a one-story home offering four bedrooms, two full bathrooms, one half bathroom, and a two-car garage. The open-concept design connects the kitchen, dining, and family rooms, creating a spacious and inviting living area. A private primary suite provides comfort and privacy, while the efficient layout supports easy living and entertaining. Modern finishes, abundant natural light, and

    Ashton Woods Builder
    17551 Lake Star Rd Unit 36646144, Winter Garden, FL 34787
  • /21

    $416,000

    • 3 Beds
    • 2.5 Baths
    • 1,868 Sq Ft

    15663 Kinnow Mandarin Ln, Winter Garden, FL 34787

    Look no further, this meticulously maintained townhouse checks all the boxes. Brand NEW ROOF (2025) and NEW CARPET with a 10-year WARRANTY makes this home feel brand new. Stainless steel kitchen appliances complete with a BOSCH DISHWASHER. the OPEN CONCEPT is inviting and there is a BONUS ROOM downstairs that could be used as an office, playroom, formal dining room, or sitting room. Enjoy the

    Steven Tsukamoto REAL LIVING R E SOLUTIONS

    15663 Kinnow Mandarin Ln, Winter Garden, FL 34787
  • /29

    $596,990 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,743 Sq Ft

    Tessa II Plan at Osprey Ranch - 32'/40' Single Family, Winter Garden, FL 34787

    Elegant primary suite with walk-in closet off foyer. Beautiful primary bath with dual sinks and seated shower. Striking kitchen with expansive breakfast bar island. Open dining area and great room with access to lanai. Versatile loft space for relaxing or entertaining. Rear load 2-car garage for parking or storage.

    K. Hovnanian Homes Builder
    15221 Blue Peacock Ln Unit 36473174, Winter Garden, FL 34787
  • /82

    $765,000

    • 4 Beds
    • 3 Baths
    • 2,970 Sq Ft

    14046 Fox Glove St, Winter Garden, FL 34787

    Stunning golf course frontage home in the highly desirable Stoneybrook West gated community of Winter Garden! This spacious residence over looks the 15th hole of the golf course and features 4 bedrooms, 3 full baths, and a screen enclosed pool with spa overlooking serene golf course views, with direct access to Black Lake — perfect for Florida living and entertaining. Recent 2026 updates include

    Laura Senzamici ENGEL & VOELKERS LAKELAND

    14046 Fox Glove St, Winter Garden, FL 34787
  • /61

    $1,450,000

    • 4 Beds
    • 3 Baths
    • 4,370 Sq Ft

    11714 Flynn Ct, Winter Garden, FL 34787

    For a champion equestrian, home is more than four walls, it’s land that performs, space that protects your horses, and a setting that allows you to train, restore, and win.Tucked away in a quiet corner of Winter Garden, yet located in Lake County for lower taxes, this rare brick estate delivers exactly that balance. Privacy when you need it. Convenience when you want it. Properties like this

    Veronica Cole THE REAL ESTATE COLLECTION LLC

    11714 Flynn Ct, Winter Garden, FL 34787
  • /49

    $719,000

    • 4 Beds
    • 3.5 Baths
    • 2,839 Sq Ft

    5966 Cypress Hill Rd, Winter Garden, FL 34787

    Welcome to 5966 Cypress Hill Rd, nestled in the highly sought-after Independence community of Winter Garden. This beautifully cared-for home offers a rare blend of privacy, space, and lifestyle amenities that truly make it stand out. One of the biggest highlights is the fully paid-off solar system, giving the next owner the benefit of extremely low electric bills—around $35 per month. It’s a huge

    Mahmoud Mango DALTON WADE INC

    5966 Cypress Hill Rd, Winter Garden, FL 34787
  • /43

    $489,000

    • 3 Beds
    • 2 Baths
    • 1,765 Sq Ft

    8216 Gray Kingbird Dr, Winter Garden, FL 34787

    !!SIGNIFICANT PRICE REDUCTION!! Come see this perfect GEM, nestled in the desirable Summerlake community in Winter Garden. This corner lot home features over 1700 sq ft, 3 bedrooms - 2 bathrooms- plus Bonus Den/Office, large kitchen that opens up to the family room and a rear load 2 car garage. The kitchen features 42"upper cabinets, spacious island, granite countertops, Stainless steel

    Lindsy Holland NEXTHOME SUNSHINE REALTY

    8216 Gray Kingbird Dr, Winter Garden, FL 34787

Showing Results 1 - 40, Page 1 of 13

Home Trends in Winter Garden, FL

Housing Trends

Median Sale Price
$570,011
Median Single Family Sale Price
$625,000
Median Townhouse Sale Price
$449,945
Median 2 Bedroom Sale Price
$230,000
Median 1 Bedroom Sale Price
$225,000
Average Price Per Sq Ft
$269
Number of Homes for Sale
672
Last 12 months Home Sales
1,848
Months of Supply
4.40
Median List Price
$599,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-1%
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