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Newest Homes for Sale in Windermere, FL

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  • /25

    $530,000

    $219K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,151 Sq Ft

    6673 Duncaster St, Windermere, FL 34786

    One or more photo(s) has been virtually staged. Located in the highly sought-after Windermere area, this 3-bedroom, 2-bath residence offers 2,151 heated square feet of functional and versatile living space. The layout includes a formal living room, a spacious great room, and a dedicated den/study, providing flexibility for work, entertaining, or additional living areas. A covered lanai extends

    Lilyan Machuca MY REALTY GROUP, LLC.

    6673 Duncaster St, Windermere, FL 34786
  • /62

    $1,750,000

    $140K PRICE DROP
    • 4 Beds
    • 5 Baths
    • 5,130 Sq Ft

    3013 Seigneury Dr, Windermere, FL 34786

    Stylish and elegant with contemporary touches, welcome home to a magnificent and expansive retreat situated on a 1-acre lot, with full-size lighted sport court with double pickleball courts (or tennis or basketball), set inside the gated enclave of Harbor Isle. This spectacular residence is unduplicated for its secluded setting – yet so close to everything – while offering an abundance of

    Rob Rahter STOCKWORTH REALTY GROUP

    3013 Seigneury Dr, Windermere, FL 34786
  • /71

    $3,195,000

    $300K PRICE DROP
    • 6 Beds
    • 5.5 Baths
    • 6,000 Sq Ft

    5538 W Lake Butler Rd, Windermere, FL 34786

    Welcome to 5538 W Lake Butler Road—an expansive, newly renovated estate set on 1.9 acres of lush, lakefront land in arguably one of Central Florida’s most coveted locations, Kelso on Lake Butler. What distinguishes this property is its remarkable dual lake access. Your own private boat dock provides direct skiable waterfront on Lake Davis, while exclusive community privileges grant you gated

    Julie Bettosini STOCKWORTH REALTY GROUP

    5538 W Lake Butler Rd, Windermere, FL 34786
  • /100

    $3,350,000

    $150K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 5,273 Sq Ft

    10577 Down Lakeview Cir, Windermere, FL 34786

    Experience true lakefront living on the famed Butler Chain of Lakes. This exceptional custom home offers 137 feet of pristine shoreline and sits on nearly one acre of high, dry land with sweeping panoramic water views and nightly Disney fireworks. Arrive via a circular paved drive framed by mature oaks and step onto the covered porch through an impressive 8 inch solid cedar entry door with

    Simon Simaan THE SIMON SIMAAN GROUP

    10577 Down Lakeview Cir, Windermere, FL 34786
  • /22

    $930,000

    $120K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,820 Sq Ft

    6752 Trellis Vine Loop, Windermere, FL 34786

    RARE PRIVACY IN WINDERMERE — 5 BEDROOMS + 2 BONUS ROOMS WITH NO REAR, FRONT-FACING, OR LEFT-SIDE NEIGHBORS Welcome to a rare Windermere opportunity offering the space, privacy, and lifestyle buyers dream about. This expansive 5-bedroom, 4-bath home features two additional bonus rooms, including a large movie/media room, giving you incredible flexibility for work, entertaining, guests, fitness,

    Candice Collins COLDWELL BANKER REALTY

    6752 Trellis Vine Loop, Windermere, FL 34786
  • /24

    $450,000

    $29K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,891 Sq Ft

    12305 Via Derna Place, Windermere, FL 34786

    Welcome to this move-in ready 3-bedroom, 3-bath townhome in Windermere FL located in the desirable Carrington community near Walt Disney World, offering low-maintenance living and a prime Central Florida location. Major updates include a NEW ROOF (2022) for peace of mind and long-term value. From the moment you arrive, you’ll notice the curb appeal, mature landscaping, and covered entry. Inside,

    Jennifer Wemert WEMERT GROUP REALTY LLC

    12305 Via Derna Place, Windermere, FL 34786
  • /26

    $1,396,000

    $56K PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 3,794 Sq Ft

    13596 Gorgona Isle Dr, Windermere, FL 34786

    Stunning Two-Story Pool Home in Prime Windermere LocationWelcome to this exceptional two-story residence located in the highly desirable Windermere area, offering the perfect blend of luxury, space, and comfort. With 6 generously sized bedrooms and an open, airy design, this home is ideal for families seeking both elegance and functionality.The primary suite is a true retreat, featuring a

    Jennifer Paiano Olmeda WRA BUSINESS & REAL ESTATE

    13596 Gorgona Isle Dr, Windermere, FL 34786
  • /35

    $415,000

    $29K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,589 Sq Ft

    13366 Abuela Aly, Windermere, FL 34786

    Welcome to this beautiful and move-in ready townhome located in the highly desirable Windermere area. Built in 2020, this modern residence offers the perfect combination of style, comfort, and low-maintenance living.This spacious home features 3 bedrooms, 2.5 bathrooms, and an open-concept layout ideal for both everyday living and entertaining. The kitchen showcases quartz countertops,

    Alexandra Mateu BAHIA INTERNATIONAL REALTY

    13366 Abuela Aly, Windermere, FL 34786
  • /70

    $7,250,000

    $345K PRICE DROP
    • 5 Beds
    • 6.5 Baths
    • 7,099 Sq Ft

    5074 Isleworth Country Club Dr, Windermere, FL 34786

    A masterfully reimagined golf-front estate, this residence offers an unparalleled standard of luxury within the acclaimed guard-gated community of Isleworth. Completely reimagined and expanded, the residence offers over 7,000 square feet of refined living space, including a 2,400+ square-foot second-story addition designed by acclaimed architect Mark Nasrallah. Situated on over half an acre, the

    Armaan Memarpouri MEM REALTY GROUP

    5074 Isleworth Country Club Dr, Windermere, FL 34786
  • /40

    $3,390,000

    $585K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 3,365 Sq Ft

    5050 Isleworth Country Club Dr, Windermere, FL 34786

    Situated on the 6th fairway along the course of Isleworth Golf & Country Club, this updated golf front sparkles with new porcelain tile throughout and modern chandeliers. This single-story residence was renovated in 2020 featuring a new tile roof, fresh paint inside and out, all bathrooms updated and a fully renovated kitchen. Spanning over 3,300 square feet, the 4-bedroom, 4.5-bath is nestled in

    Agent Photo

    Toni Marie Cafferty

    COMPASS FLORIDA LLC

    5050 Isleworth Country Club Dr, Windermere, FL 34786
  • /34

    $650,000

    $60K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,511 Sq Ft

    13232 Longacre Dr, Windermere, FL 34786

    Wonderful home in desired Windermere. This two-story home features five large bedrooms and 3 bathrooms and a spacious 2 car garage. Designed with an open floor plan has a large living and dining area and a kitchen with lots of cabinets and pantry.The main floor offers 2 first-floor bedrooms for added convenience and flexibility, for guests or multipurpose room/office plus pantry and storage

    Maria Kronenberg CHARLES RUTENBERG REALTY ORLANDO

    13232 Longacre Dr, Windermere, FL 34786
  • /59

    $680,000

    • 4 Beds
    • 2.5 Baths
    • 2,947 Sq Ft

    13339 Roskin Ln, Windermere, FL 34786

    Welcome to a standout opportunity in WINDERMERE , offering closing cost assistance and positioned for a timely sale. This 4 bedroom, 2.5 bath, two-story home with 2,947 sq ft delivers the space, layout, and location today’s buyers are searching for. The thoughtfully designed floor plan includes a first-floor den/office, expansive upstairs loft, and generously sized bedrooms throughout. The

    Karla Price COLDWELL BANKER REALTY

    13339 Roskin Ln, Windermere, FL 34786
  • /46

    $575,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,139 Sq Ft

    6442 Golden Dewdrop Trail, Windermere, FL 34786

    Short Sale. Come see this beautiful place. This immaculate home features include over 2,100 square feet of living space, a desirable Kitchen with 42" Cabinets and Granite, Stainless Steel Appliances, Beautiful Backsplash, engineered hardwood flooring on the first floor, vinyl on the second floor, ceramic tile in bathrooms and laundry, screened-in patio porch with a ceiling fan, an elegant

    Yindy Reyes EMPIRE NETWORK REALTY

    6442 Golden Dewdrop Trail, Windermere, FL 34786
  • /54

    $717,000

    $32K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,594 Sq Ft

    13519 Bicton Ln, Windermere, FL 34786

    Welcome to one of Windermere's most sought-after gated communities — where luxury living meets unbeatable Central Florida convenience. This impeccably maintained 4-bedroom, 3-bathroom home offers nearly 3,000 square feet of thoughtfully designed living space, a 3-car garage, and a brand-new roof and windows, giving buyers peace of mind and long-term value from day one.DISNEY VIEWS & OUTDOOR

    Agent Photo

    Tiphany Weeks

    DIAMOND REAL ESTATE GROUP

    13519 Bicton Ln, Windermere, FL 34786
  • /91

    $560,000

    • 4 Beds
    • 2.5 Baths
    • 1,840 Sq Ft

    8225 Bryce Canyon Ave, Windermere, FL 34786

    Beautiful 4-Bedroom Home in Windermere, FL – Prime Location and Comfort for the Whole Family! Discover this amazing homelocated in one of Florida’s most desirable neighborhoods – Windermere! Featuring 4 spacious bedrooms, 2 full bathrooms and a half bath, this property offers the ideal space and layout for families seeking comfort and quality of life. The home is vacant and move-in ready,

    Fernando Zucato CHARLES RUTENBERG REALTY ORLANDO

    8225 Bryce Canyon Ave, Windermere, FL 34786
  • /64

    $6,000,000

    $950K PRICE DROP
    • 7 Beds
    • 7 Baths
    • 8,000 Sq Ft

    9725 Chestnut Ridge Dr, Windermere, FL 34786

    Newly renovated, this private Isleworth residence offers a rare balance of architectural authority, thoughtful design, and quiet indulgence.Spanning approximately 8,000 square feet, the home unfolds with intention. Rich walnut cabinetry and wood detailing create warmth and continuity throughout, while the fireplace and wine cellar anchor the living spaces with understated elegance. Every room

    Dianna Desboyaux DOUGLAS ELLIMAN

    9725 Chestnut Ridge Dr, Windermere, FL 34786
  • /26

    $4,395,000

    • Land
    • 1 Acre
    • $4,395,000 per Acre

    12418 Park Ave, Windermere, FL 34786

    WELCOME TO PARK AVENUE. An extraordinary opportunity awaits on 1 acre of prime lakefront with coveted southeastern exposure and sweeping panoramic views. Perfectly positioned along the pristine shoreline of Lake Butler on the renowned Butler Chain of Lakes, this exclusive homesite is located within one of Windermere’s most desirable gated enclaves—Chaine Du Lac. Offering the rare distinction of

    Michael Julian JULIAN PROPERTIES, INC.

    12418 Park Ave, Windermere, FL 34786
  • /82

    $2,175,000

    $110K PRICE DROP
    • 6 Beds
    • 6 Baths
    • 5,031 Sq Ft

    713 Main St, Windermere, FL 34786

    Architecturally refined and thoughtfully designed, this custom built Transitional Craftsman residence blends timeless craftsmanship with modern luxury in the heart of Historic Olde Windermere with excellent walkability. Rich wood detailing, exposed pecky cypress beams, and dramatic stonework create warmth and depth throughout. The chef’s kitchen is both functional and sculptural, featuring a

    Agent Photo

    Kari Fleck

    THE REAL ESTATE COLLECTION LLC

    713 Main St, Windermere, FL 34786
  • /28

    $10,500,000

    $1M PRICE DROP
    • Land
    • 9.03 Acres
    • $1,162,791 per Acre

    4226 Downeast Ln, Windermere, FL 34786

    Dramatic price improvement on this exceptional 5+ acre Lake Down development opportunity, offering 300 feet of pristine shoreline on the coveted Butler Chain of Lakes and positioned on the best side of Windermere with unmatched convenience to SR-408 and downtown Orlando. This rare parcel, zoned R-CE, allows for the creation of up to three luxury lakefront homes or a single premier estate

    Thad Czapka COLDWELL BANKER REALTY

    4226 Downeast Ln, Windermere, FL 34786
  • /69

    $870,000

    $29K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,312 Sq Ft

    13106 Orange Isle Dr, Windermere, FL 34786

    Explore the WINTERSET model from Ryan Homes of the Sanctuary at Lakes of Windermere, a corner unit, this 5- bedroom, 4.5 bathroom in Windermere combines the modern elegance, and a touch of magic with its a DISNEY Fireworks view, offering a lifestyle of unparalleled comfort. Upon entering, you are greeted by those who appreciate a dedicated workspace, the home includes a spacious office and a

    Victor De Oliveira FLORIDA CONNEXION PROPERTIES

    13106 Orange Isle Dr, Windermere, FL 34786
  • /58

    $965,000

    $110K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,743 Sq Ft

    2125 Kane Park Way, Windermere, FL 34786

    Fresh Exterior Updates! This beautifully updated custom home has just been refreshed with new exterior paint and a newly painted pool deck, enhancing its curb appeal and outdoor living spaces. Updated professional photography will be added soon to showcase the refreshed exterior and recent improvements. Rare opportunity to own a custom pool home on .71 acres in the Town of Windermere for under $1

    Deb Schroeder INFINITY REALTY GROUP LLC

    2125 Kane Park Way, Windermere, FL 34786
  • /53

    $3,150,000

    $350K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 4,676 Sq Ft

    6130 Grosvenor Shore Dr, Windermere, FL 34786

    Exceptional Waterview Estate in Keenes Pointe / Resort-Style Outdoor Living. Located on a quiet cul-de-sac in the exclusive guard-gated community of Keenes Pointe, this custom Goehring & Morgan residence offers luxurious main-floor living paired with spectacular outdoor entertaining spaces and tranquil water views. Designed for both comfort and entertaining, the home features a heated saltwater

    Dianna Desboyaux DOUGLAS ELLIMAN

    6130 Grosvenor Shore Dr, Windermere, FL 34786
  • /56

    $815,000

    • 5 Beds
    • 3 Baths
    • 3,211 Sq Ft

    4415 Blue Major Dr, Windermere, FL 34786

    This beautiful MOVE-IN-READY two-story home is located in the highly desired community of Summerport in Windermere! The Wow factor begins the moment the front door opens to a towering cathedral ceiling making for a dramatic and elegant entry into the main living area. The open floor plan creates a seamless flow throughout the home, whereby the family room opens to the kitchen and dinette space,

    Mariana Micheti M2M REALTY

    4415 Blue Major Dr, Windermere, FL 34786
  • /95

    $4,850,000

    $75K PRICE DROP
    • 7 Beds
    • 8 Baths
    • 8,931 Sq Ft

    9575 Westover Roberts Rd, Windermere, FL 34786

    Discover “Bella Olivia”: a grand mediterranean estate perched high above Lake Olivia showcasing sweeping lake views, private gates, and an expansive luxury residence spanning over 8,900 square feet of living space across 7 bedrooms, including two primary suites, two guest apartments, garage space for 6 cars, an enormous screened enclosure with resort-style pool and spa, over 5.4 acres and no HOA.

    Rob Rahter STOCKWORTH REALTY GROUP

    9575 Westover Roberts Rd, Windermere, FL 34786
  • /75

    $10,900,000

    $901K PRICE INCREASE
    • 6 Beds
    • 8 Baths
    • 6,783 Sq Ft

    6149 Grosvenor Shore Dr, Windermere, FL 34786

    Keene's Pointe - Stunning lakefront home on Lake Tibet of the famed Butler Chain of Lakes. No detail was spared in this completely renovated home boasting formal living and dining rooms, family and media room, 2 offices, 6 full/2 half baths and 6 bedrooms - one of which could serve as a in-law suite with separate entrance from the outside. From the moment you enter this impeccably designed home

    Teresa Stewart SOUTHERN REALTY GROUP LLC

    6149 Grosvenor Shore Dr, Windermere, FL 34786
  • /32

    $1,855,000

    $245K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 4,716 Sq Ft

    2958 Marquesas Ct, Windermere, FL 34786

    PRICE IMPROVEMENT! Recently appraised - Pricing adjusted to reflect current appraised value. This beautiful and elegant courtyard-style estate, complete with a PRIVATE GUEST HOUSE/IN-LAW SUITE, offers the ideal retreat for multi-generational living within one of the most exclusive gated communities in the Town of Windermere. Designed for comfort, refinement, and privacy, this home embodies

    Dianna Desboyaux DOUGLAS ELLIMAN

    2958 Marquesas Ct, Windermere, FL 34786
  • /56

    $925,000

    $50K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,636 Sq Ft

    3328 Wax Berry Ct, Windermere, FL 34786

    One or more photo(s) has been virtually staged. Located within Lake Butler Estates, one of Windermere’s most private and established communities, this 4-bedroom, 4-bath pool home is situated on a one-acre cul-de-sac lot surrounded by mature oak trees and only 11 neighboring homes. Originally constructed in 1984 and renovated in 2022, this single-story home offers an open, split floor plan that

    Ferris Kassar PREFERRED REAL ESTATE BROKERS

    3328 Wax Berry Ct, Windermere, FL 34786
  • /49

    $1,200,000

    • 4 Beds
    • 4 Baths
    • 2,787 Sq Ft

    1361 Whitney Isles Dr, Windermere, FL 34786

    Stunning residence with a private fenced backyard, located in the highly sought-after gated community of Belmere in Windermere, just minutes from the town center. Featuring 4 bedrooms, 4 bathrooms, and approximately 2,800 sq. ft. of air-conditioned living space, this home immediately captivates with its elegant Mediterranean architecture and lush tropical landscaping. Fully renovated this year,

    Gabriel Mantovani ALVES AND HOWELL REALTY

    1361 Whitney Isles Dr, Windermere, FL 34786
  • /55

    $995,000

    $50K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,248 Sq Ft

    11162 Ledgement Ln, Windermere, FL 34786

    NEW TILE ROOF INSTALLED PRIOR TO CLOSING! Located in Glenmuir, one of Windermere's most sought-after gated communities, this beautifully maintained pool home offers 4 bedrooms, 3 full baths, 2 half baths, a private office, bonus room, and a desirable mostly single-story floor plan. Backing to peaceful greenspace with NO REAR NEIGHBORS, this home combines privacy, functionality, and resort-style

    Deb Schroeder INFINITY REALTY GROUP LLC

    11162 Ledgement Ln, Windermere, FL 34786
  • /50

    $680,000

    $15K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 2,976 Sq Ft

    6712 Thornhill Cir, Windermere, FL 34786

    With timeless curb appeal and a front porch built for slow mornings, this Windermere home blends classic charm with the upgrades that make everyday life easier. Step inside and the ceilings rise, sunlight floods through, and hardwood floors (2021) lead you through open living and dining spaces that flow seamlessly into a remodeled kitchen with quartz countertops, updated cabinetry, and dual

    Brad Young HOMEVEST REALTY

    6712 Thornhill Cir, Windermere, FL 34786
  • /65

    $5,100,000

    $225K PRICE DROP
    • 4 Beds
    • 5.5 Baths
    • 6,424 Sq Ft

    5243 Isleworth Country Club Dr, Windermere, FL 34786

    Presenting a magnificent Isleworth golf front estate with sweeping lake views, perched above holes #2 and #9 and Lake Chase, combining a completely reimagined interior with designer elegance and modern grand style. With no neighbors on three sides, this stunning home offers a unique combination of privacy mixed with rare golf and water vistas. Home recently underwent a major “spare no expense”

    Rob Rahter STOCKWORTH REALTY GROUP

    5243 Isleworth Country Club Dr, Windermere, FL 34786
  • /30

    $2,175,000

    New Construction $250K PRICE DROP
    • 4 Beds
    • 5 Baths
    • 3,136 Sq Ft

    436 E 7th Ave, Windermere, FL 34786

    Seller is Motivated and open to negotiate! Luxury new construction lakefront home in Windermere, newly completed. Situated on Lake Bessie, this modern custom residence delivers architectural elegance, premium finishes, and a prime location just steps from the Town Center. The home offers 3,136 sq ft of air-conditioned space, featuring 4 en-suite bedrooms, a dedicated office at the entry, 5 full

    DENILEY VALDES TALENT REALTY SOLUTIONS

    436 E 7th Ave, Windermere, FL 34786
  • /32

    $1,390,000

    Open Sat 12PM - 3PM $110K PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 4,999 Sq Ft

    17538 Black Rail St, Windermere, FL 34786

    Spacious 6-bedroom, 4-bath Windermere home with dual master suites, pond views, and a fenced yard. Built in 2014, this residence features an open layout with a gourmet kitchen, granite counters, stainless steel appliances, and 42” cabinets. Upstairs includes a loft/media room and generously sized bedrooms. Enjoy serene water views, a private backyard, and a 3-car garage. Located in a desirable

    Agent Photo

    Elaine Garcia

    GARCIA REALTY GROUP

    17538 Black Rail St, Windermere, FL 34786
  • /2

    $575,000

    $25K PRICE INCREASE
    • Land
    • 20,473 Sq Ft
    • $1,223,404 per Acre

    9802 6th St, Windermere, FL 34786

    Vacant lot on the corner of 6th and Hempel. Prime investment property.

    Judy Plett UPSIDE REAL ESTATE INC

    9802 6th St, Windermere, FL 34786
  • /14

    $1,085,990

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,074 Sq Ft

    Griffin Plan at Lake Cawood Cove - Traditional, Windermere, FL 34786

    The Griffin is a two-story home offering four bedrooms, three full bathrooms, one half bathroom, and a two-car garage. The kitchen opens to a dramatic two-story family room, creating a bright and inviting living space. The second-floor primary suite offers privacy and comfort, while a conveniently located laundry room and optional butler’s pantry enhance everyday functionality. Additional

    Ashton Woods Builder
    5432 Winter Garden Vineland Rd Unit 37932783, Windermere, FL 34786
  • /13

    $1,146,990

    New Construction
    • 5 Beds
    • 4.5 Baths
    • 3,542 Sq Ft

    Duval Plan at Lake Cawood Cove - Traditional, Windermere, FL 34786

    The Duval is a two‐story home offering five bedrooms, four full bathrooms, one half bathroom, and a two‐car garage. A bright kitchen with breakfast nook anchors the open main floor, while a second‐floor loft overlooks the family room below. The private second‐floor primary suite, optional butler’s pantry, and centrally located laundry room add convenience and luxury to this spacious plan.

    Ashton Woods Builder
    5432 Winter Garden Vineland Rd Unit 37932788, Windermere, FL 34786
  • /17

    $1,052,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,791 Sq Ft

    Moseley Plan at Lake Cawood Cove - Traditional, Windermere, FL 34786

    The Moseley 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. Modern finishes, abundant

    Ashton Woods Builder
    5432 Winter Garden Vineland Rd Unit 37932785, Windermere, FL 34786

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