Windermere, FL Homes

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  /36

  $635,000

  • 4 Beds
  • 3 Baths
  • 2,501 Sq Ft

  5624 Remsen Cay Ln, Windermere, FL 34786

  Welcome to 5624 Remsen Cay—a stunning 4-bedroom, 3-bathroom POOL home located in the highly sought-after Summerport community. Originally built as the model home, this property showcases all the prime features you’d expect. From the charming front porch, enjoy a peaceful view of the community pond. Step inside and you’re greeted by soaring ceilings and natural light flowing from the foyer all the

  Shelby Serrao COMPASS FLORIDA LLC

  5624 Remsen Cay Ln, Windermere, FL 34786
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  /11

  $2,300 per month

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft
  • Condo for Rent

  8180 Boat Hook Loop Unit 310, Windermere, FL 34786

  Great apartment for rent in the beautiful City of Windermere Orlando FL, 3 bedrooms 2 full Baths, corner unit on the first floor of the building, screened private patio, new paint throughout, spacious dining and living room area, large kitchen, moder tile and laminate flooring, fans in all bedrooms and living room, 2 parking spaces, water included. Community offers clubhouse with pool, fitness

  Kristine Puente TOP TEAM REALTY, LLC.

  8180 Boat Hook Loop Unit 310, Windermere, FL 34786
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  /2

  $685,000 Sold Aug 01, 2025

  • 3,268 Sq Ft
  • $210/SF
  • 0 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2005

  1444 Whitney Isles Dr, Windermere, FL 34786

  FLORIDA living at its finest. Windermere gated community of Whitney Isles?Belmere. This 4 bedroom, 3 full baths and a half bath will give your family a perfect blend of comfort and convenience. The new roof is only 3 years old! Master bedroom is on the first floor with two Walkin closets, a large bathroom with a large walk-in shower and garden tub. Sliding glass door opens to your private

  Kimberly Cook ENGEL & VOLKERS CLERMONT

  1444 Whitney Isles Dr, Windermere, FL 34786
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  /53

  Est $1,107,626 Not Listed For Sale

  • 6 Beds
  • 4.5 Baths
  • 4,502 Sq Ft

  8799 Crescendo Ave, Windermere, FL 34786

  8799 Crescendo Ave, Windermere, FL 34786
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  /34

  $569,000

  • 3 Beds
  • 2 Baths
  • 1,819 Sq Ft

  9150 Palm Tree Dr, Windermere, FL 34786

  Freshly renovated and move in ready, this Silver Woods 3 bed 2 bath home offers 1,819 square feet of bright, open living. Big ticket items are done for you: roof 2022, HVAC 2023, water heater 2022, and a new septic tank in 2024. The 2024 kitchen showcases quartz counters, shaker cabinetry, stainless appliances, and recessed lighting, all paired with 2024 luxury vinyl plank flooring and a fresh

  Steven Koleno BEYCOME OF FLORIDA LLC

  9150 Palm Tree Dr, Windermere, FL 34786
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  /3

  $3,400 per month

  • 4 Beds
  • 3 Baths
  • 2,551 Sq Ft
  • House for Rent

  11032 Belmere Isles Ct, Windermere, FL 34786

  Beautiful 4 bedroom, 3 bath home located within guard gated community of the Reserves of Belmere. Screened in pool overlooking pond. Eat in kitchen. Two car garage. Located on cud-a-sac. Come see!

  Barbara Schafer Holland CLASSIC INTERNATIONAL REALTY LLC

  11032 Belmere Isles Ct, Windermere, FL 34786
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  /2

  $498,000 Sold Aug 01, 2025

  • 2,085 Sq Ft
  • $239/SF
  • 55 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2006

  4813 River Gem Ave, Windermere, FL 34786

  PRICED TO SELL...Seller is motivated! Fall in Love with this Windermere Charmer! From the shaded front porch swing nestled beneath mature trees to the extended paver patio overlooking tranquil water views, this beautifully maintained 3-bedroom, 2-bath home is the picture of comfort and charm. Located in highly desirable Summerport, this home features a thoughtful split-bedroom

  Suzanne Hosmer RE/MAX SELECT GROUP

  4813 River Gem Ave, Windermere, FL 34786
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  /42

  Est $895,663 Not Listed For Sale

  • 6 Beds
  • 4 Baths
  • 3,804 Sq Ft

  11859 Gold Creek Trail, Windermere, FL 34786

  11859 Gold Creek Trail, Windermere, FL 34786
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  /86

  $1,590,000

  • 5 Beds
  • 4.5 Baths
  • 4,226 Sq Ft

  9649 Weatherstone Ct, Windermere, FL 34786

  Welcome to Weatherstone on Lake Olivia, one of Windermere’s most sought-after gated communities. With only 13 custom executive homes, each set on expansive one-acre homesites, this neighborhood offers a rare blend of exclusivity, privacy, and charm.From the moment you arrive, you’ll be greeted by beautiful curb appeal and a sweeping semi-circle driveway. Step inside this thoughtfully designed

  Newton Hieda SUMMERHILL REALTY GROUP LLC

  9649 Weatherstone Ct, Windermere, FL 34786
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  /39

  $12,000 per month

  • 5 Beds
  • 4.5 Baths
  • 4,417 Sq Ft
  • House for Rent

  5001 Latrobe Dr, Windermere, FL 34786

  Available for immediate occupancy. This beautiful, traditional five-bedroom pool home is on a quiet cul-de-sac in Isleworth, Windermere. The traditional brick exterior, grand French doors, and warm mahogany wood floors invite friends and family home. Enjoy views of majestic oaks, the 7th fairway, and Lake Bessie on this half-acre lot. This two-story home is perfect for entertaining and easy to

  Laura Diss Q BOUTIQUE SPECIALTY REALTY INC

  5001 Latrobe Dr, Windermere, FL 34786
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  /2

  $345,000 Sold Jul 31, 2025

  • 1,520 Sq Ft
  • $227/SF
  • 11 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2013

  12359 Langstaff Dr, Windermere, FL 34786

  Beautiful Townhome with Disney Firework Views in Sought-After WindermereAC FIVE YEAR OLD, OVEN 1 YEAR OLD, NEW MASTER BATHROOM SHOWER DOORThis charming end-unit townhome offers stunning Disney firework views and is ideally located in one of Windermere’s most desirable communities. With no front neighbors, the master bedroom enjoys tranquil views of a dry pond and mature trees,

  Jing Yue INTEREALTY SERVICE

  12359 Langstaff Dr, Windermere, FL 34786
• 

  

  /23

  Est $442,895 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,676 Sq Ft

  8655 Coventry Park Way, Windermere, FL 34786

  8655 Coventry Park Way, Windermere, FL 34786
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  /81

  $5,489,000

  • 6 Beds
  • 9 Baths
  • 8,305 Sq Ft

  9721 Carillon Park Dr, Windermere, FL 34786

  Welcome to a stunning, fully furnished, professionally designed home nestled within the guard gates of Keenes Pointe in Windermere. This exceptional residence boasts 8,305 sq ft of luxurious living space, meticulously crafted with top finishes and elegant wood beams throughout. This home offers ample space and privacy for everyone with three rooms on the first floor, an additional bedroom

  Dianna Desboyaux SOUTHERN REALTY GROUP LLC

  9721 Carillon Park Dr, Windermere, FL 34786
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  /50

  $5,800 per month

  • 3 Beds
  • 2 Baths
  • 1,725 Sq Ft
  • House for Rent

  12860 Lake Sawyer Ln, Windermere, FL 34786

  Private LAKEFRONT estate home on that sits on almost 2 acres of land, gated for extreme privacy! Fully furnished with an open floorplan great for families and entertaining. This home features 3 cozy bedrooms with a king, queen, and full bed to accommodate all guests comfortably. Enjoy the convenience of 2 bathrooms, one with a relaxing jetted bathtub. Kitchen features butcher block countertops,

  Aleem Kanji CROWN REALTY COMPANY

  12860 Lake Sawyer Ln, Windermere, FL 34786
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  /2

  $1,468,000 Sold Jul 31, 2025

  • 5,247 Sq Ft
  • $280/SF
  • 42 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2007

  9032 Tavolini Terrace, Windermere, FL 34786

  Luxury Meets Lifestyle at 9032 Tavolini Terrace, Windermere, FL!Welcome to an exceptional blend of refined design and resort-style living nestled in the heart of Windermere. This stunning 5-bedroom, 4.5-bath estate spans just over 5200 square feet of meticulously upgraded interiors and masterfully redesigned outdoor spaces — all curated for the most discerning homeowner.Step

  Jacky Herrera COMPASS FLORIDA LLC

  9032 Tavolini Terrace, Windermere, FL 34786
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  /2

  Est $3,545,329 Not Listed For Sale

  • 4 Beds
  • 7 Baths
  • 5,727 Sq Ft

  5006 Sawyer Cove Way, Windermere, FL 34786

  5006 Sawyer Cove Way, Windermere, FL 34786
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  /49

  $1,890,000

  • 6 Beds
  • 4 Baths
  • 3,894 Sq Ft

  9922 Brentford Ct, Windermere, FL 34786

  If you want something turn-key in Keene’s Pointe, sitting in one of the most desirable locations in the community, then look no further. This is a home you can move into today, sit down and live, without touching a single thing. This home has not only been renovated from end to end, but also has a three year old new tile roof!! Every square inch of the house feels brand new as you walk thru. It

  Shane Croft COLDWELL BANKER RESIDENTIAL RE

  9922 Brentford Ct, Windermere, FL 34786
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  /46

  $5,500 per month

  • 4 Beds
  • 3 Baths
  • 2,830 Sq Ft
  • House for Rent

  2113 Grove Point Ln, Windermere, FL 34786

  Discover this stunning rental home located in the Waterford Pointe community on Lake Roberts. Enjoy exclusive access to a private community boat ramp in a serene, gated neighborhood.This beautifully furnished residence features new bamboo flooring, high-end appliances, and elegant decor throughout. Designed for year-round Florida living, the home includes a private in-ground pool, spa,

  Alexandra Costa Thomas THE FLORIDA LOUNGE REALTY LLC

  2113 Grove Point Ln, Windermere, FL 34786
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  /2

  $890,000 Sold Jul 31, 2025

  • 2,562 Sq Ft
  • $347/SF
  • 274 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1971

  235 Oakdale St, Windermere, FL 34786

  Best priced home within the town! Here is your opportunity to own a single-story fully remodeled pool home on a corner lot in the desirable downtown Windermere with NO HOA on county water! At first glance you will immediately appreciate the charming curb appeal your home has to offer. It is constructed with masonry block and Hardie board siding on a concrete slab. The main living areas of your

  Simon Simaan THE SIMON SIMAAN GROUP

  235 Oakdale St, Windermere, FL 34786
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  /21

  Est $800,546 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,775 Sq Ft

  8736 Peachtree Park Ct, Windermere, FL 34786

  8736 Peachtree Park Ct, Windermere, FL 34786
• 

  

  /47

  $759,900

  • 4 Beds
  • 4 Baths
  • 3,129 Sq Ft

  13649 Zori Ln, Windermere, FL 34786

  Welcome to 13649 Zori Lane, a conveniently located home in the highly sought-after Providence Community and within the top-rated Windermere school district! This beautiful move-in-ready, four-bedroom, four-bathroom property radiates luxury and comfort, features light-filled spaces with 10-foot high ceilings, creating an open and airy feeling. Upon entrance, you will be greeted with a charming

  Deon Paul VYLLA HOME

  13649 Zori Ln, Windermere, FL 34786
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  /20

  $2,450 per month

  • 3 Beds
  • 2.5 Baths
  • 1,512 Sq Ft
  • Townhouse for Rent

  8867 Herencia Alley, Windermere, FL 34786

  This beautifully designed 3-bedroom townhome boasts an open-concept floor plan that seamlessly integrates the living, dining, and kitchen spaces. Enjoy cooking in the modern kitchen featuring stainless steel appliances, granite countertops, and abundant cabinetry. The spacious master suite is a serene retreat, complete with a walk-in closet and en-suite bathroom, and large size Patio. while two

  Jiu Feng Wei AAA GLOBAL VENTURES PA

  8867 Herencia Alley, Windermere, FL 34786
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  /2

  $615,000 Sold Jul 30, 2025

  • 2,460 Sq Ft
  • $250/SF
  • 7 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2003

  12524 Aldershot Ln, Windermere, FL 34786

  **LOCATION -- LOCATION -- LOCATION** **BRAND NEW ROOF -- APRIL 2025** **FRESHLY PAINTED EXTERIOR -- APRIL 2025** **4 BEDROOMS + 2.5 BATHROOMS -- ALL ON ONE LEVEL** **LARGE FULLY RENOVATED KITCHEN -- 2022** **UPDATED WOOD-LOOK TILE FLOORING** **AVAILABLE FOR QUICK CLOSE & MOVE-IN** **A+ SCHOOLS** **LOW HOA** Welcome to the highly desired Lakes of Windermere neighborhood -- with lovely

  Tara Moore TARA MOORE REAL ESTATE

  12524 Aldershot Ln, Windermere, FL 34786
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  /2

  Est $585,984 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,322 Sq Ft

  8014 Jailene Dr, Windermere, FL 34786

  8014 Jailene Dr, Windermere, FL 34786
• 

  

  /57

  $3,400,000

  • 4 Beds
  • 4 Baths
  • 4,877 Sq Ft

  9731 Chestnut Ridge Dr, Windermere, FL 34786

  Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers and framed by oversized windows that capture elevated views of the resort-style pool and spa below.

  Monica Lochmandy ISLEWORTH REALTY LLC

  9731 Chestnut Ridge Dr, Windermere, FL 34786
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  /35

  $3,600 per month

  • 3 Beds
  • 2 Baths
  • 1,928 Sq Ft
  • House for Rent

  1243 Dingens Ave, Windermere, FL 34786

  WONDERFUL WELCOME HOME IN WINDERMERE. READY TO MOVE IN. TOP RATED SCHOOLS IN A FAMILY COMMUNITY, NEAR DISNEY, DINING AND ENTERTAINMENT, MAY BE RENTED FULL FURNISHED, FEELS LIKE COUNTRY LIVING, BUT CLOSE TO EVERYTHING,so bring your boat, camper, or build the Gotha Park is just a short walk away, offering tennis courts, a pavilion, and a tot lot for the little ones. LOCATION, LOCATION,

  Peter Useche REALMULTIPROPERTY LLC

  1243 Dingens Ave, Windermere, FL 34786
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  /2

  $670,000 Sold Jul 30, 2025

  • 2,755 Sq Ft
  • $243/SF
  • 3 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2003

  13943 Caywood Pond Dr, Windermere, FL 34786

  Welcome Home, one of the best floorplans in all of Summerport, this 4 bedroom plus office, 3 full bath plus 3 car garage home is all one story. With a large screened in patio that overlooks your immense, fully fenced yard right next to one of the several community maintained ponds. Featuring newer roof (2018), Newer HVAC (2023), fresh interior repaint, new carpet, this home is ready to me moved

  Greg Traub COMPLETE FLORIDA REALTY LLC

  13943 Caywood Pond Dr, Windermere, FL 34786
• 

  

  /18

  Est $422,517 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,617 Sq Ft

  13179 Kegan St, Windermere, FL 34786

  13179 Kegan St, Windermere, FL 34786
• 

  

  /41

  $974,900

  • 4 Beds
  • 3.5 Baths
  • 3,938 Sq Ft

  1451 Whitney Isles Dr, Windermere, FL 34786

  Welcome to your luxury oasis in the exclusive, gated community of Belmere. This beautifully landscaped, Mediterranean-style residence is the perfect blend of elegance and comfort, offering four bedrooms, three and a half baths, and a three-car garage. Step inside through grand double glass doors into a two-story foyer with soaring ceilings. The open-concept layout is perfect for entertaining,

  Odel Ximinies COLDWELL BANKER RESIDENTIAL RE

  1451 Whitney Isles Dr, Windermere, FL 34786
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  /80

  $3,099 per month

  • 4 Beds
  • 3.5 Baths
  • 2,600 Sq Ft
  • House for Rent

  13426 Chariho Ln, Windermere, FL 34786

  Welcome to this beautifully maintained 4-bedroom, 3-bath home with a loft and office located in a highly sought-after gated community in Windermere. This spacious residence offers a fresh, move-in-ready feel with fairly new carpeting throughout the stairs and second floor. The thoughtfully designed floor plan features a first-floor master suite, providing privacy and convenience, along with a

  Courtney James LA ROSA REALTY ORLANDO LLC

  13426 Chariho Ln, Windermere, FL 34786
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  /2

  $2,700,000 Sold Jul 30, 2025

  • 3,469 Sq Ft
  • $778/SF
  • 12 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1959

  606 Butler St, Windermere, FL 34786

  Amazing opportunity having over 125 feet of shoreline on Lake Butler of the famed Butler Chain of Lakes - Over 1 acre of dry land having over 342 feet - Huge 45 x 31 - 4 Car Garage that can double as a detached Inlaw Apartment with a private entrance - Main 1 Story Home is over 3,400 sq ft - Very Rare Fully Enclosed Boathouse that is grandfathered in - Seawall - Crystal Clear Water - White Sand

  Darrell Nunnelley VINTAGE REALTY GROUP LLC

  606 Butler St, Windermere, FL 34786
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  /12

  Est $496,879 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,047 Sq Ft

  8320 Bryce Canyon Ave, Windermere, FL 34786

  8320 Bryce Canyon Ave, Windermere, FL 34786
• 

  

  /35

  $299,000

  • 2 Beds
  • 2 Baths
  • 1,161 Sq Ft

  11446 Jasper Kay Terrace Unit 309, Windermere, FL 34786

  Welcome to Lakeside! This well maintained 2 bedroom/2 bath unit is located on the third floor with no upstairs neighbors! You'll be impressed by the size of the living area in this light and bright unit which includes a good size living room with separate dining area and a spacious kitchen with a breakfast bar and a tiled backsplash. All of the bedrooms are great sizes, the primary bedroom having

  Amanda Volence CHARLES RUTENBERG REALTY ORLANDO

  11446 Jasper Kay Terrace Unit 309, Windermere, FL 34786
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  /11

  $4,500 per month

  • 4 Beds
  • 2.5 Baths
  • 2,588 Sq Ft
  • House for Rent

  12025 Lake Butler Blvd, Windermere, FL 34786

  Welcome to your 4-bedroom, 3-bathroom, three car garage sanctuary! As you open your beautiful door, expect to be wowed at your perfect masterpiece. You are greeted by your huge family room leading into the living room with a wood burning fireplace. Your living room boasts lighting through your rear doors leading to your gorgeous, screen enclosed patio. This home has a layout picture-perfect for

  Camille Simon MCO REALTY

  12025 Lake Butler Blvd, Windermere, FL 34786
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  /2

  $2,000,000 Sold Jul 30, 2025

  • 1,124 Sq Ft
  • $1,779/SF
  • 137 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1966

  10433 Trout Rd, Orlando, FL 32836

  Don't miss this amazing lakefront lot with 100 feet of frontage on LAKE TIBET, part of the sought-after Butler Chain of Lakes. With direct access to 12 connected lakes, this is a dream spot for boating, fishing, and water sports.Sitting right next to Butler - Tibet Preserve Park, this 3.31-acre property offers breathtaking views, privacy, serenity and tons of potential. There’s a small house

  Ursula Garcia Moraes PRISTINE INTERNATIONAL REALTY LLC

  10433 Trout Rd, Orlando, FL 32836
• 

  /2

  Est $1,896,728 Not Listed For Sale

  • 6 Beds
  • 5.5 Baths
  • 5,497 Sq Ft

  12408 Corso Ct, Windermere, FL 34786

  12408 Corso Ct, Windermere, FL 34786
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  /63

  $3,400,000

  • 5 Beds
  • 5.5 Baths
  • 4,701 Sq Ft

  2012 Bellamere Ct, Windermere, FL 34786

  Exquisitely appointed and elegantly packaged former model home, showcasing the pinnacle of perfection, from luxury home builder Element Homes. This masterpiece stands supreme for its high-quality fit and finish and a highly desirable floorplan – featuring a great room combination of family room, dining room, and kitchen – masterfully crafted to exhibit transitional style and function. A wall of

  Rob Rahter STOCKWORTH REALTY GROUP

  2012 Bellamere Ct, Windermere, FL 34786
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  /49

  $6,450 per month

  • 4 Beds
  • 3 Baths
  • 3,190 Sq Ft
  • House for Rent

  307 W 4th Ave, Windermere, FL 34786

  Executive rental pool home located in the charming town of Windermere! The location is just two block from Main st and all that downtown Windermere has to offer! This single-story, 4-bedroom (2 primary bedrooms), 3-bathroom home, sits on an oversized corner lot in the shade of majestic oak trees. Enjoy a gourmet kitchen featuring stainless steel appliances, two brand new refrigerators, a

  Katie Bray MAINFRAME REAL ESTATE

  307 W 4th Ave, Windermere, FL 34786
• 

  /2

  $370,000 Sold Jul 29, 2025

  • 1,840 Sq Ft
  • $201/SF
  • 23 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2013

  14344 Desert Haven St, Windermere, FL 34786

  Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome in the highly sought-after Oasis Cove community in Windermere, Florida. Boasting 1,840 square feet of spacious living, this home offers a perfect blend of comfort and style. The open-concept layout features a bright and airy living area, a modern kitchen with ample cabinetry and counter space, and a cozy dining area—ideal for

  Gonzalo Senior IRM INVEST., REAL EST.& MGMT.

  14344 Desert Haven St, Windermere, FL 34786
• 

  

  /36

  Est $894,656 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,051 Sq Ft

  7242 Rambling Water Way, Windermere, FL 34786

  7242 Rambling Water Way, Windermere, FL 34786

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