Windermere, FL Homes

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  /33

  $585,000

  • 3 Beds
  • 2 Baths
  • 1,732 Sq Ft

  13430 Hopkinton Ct, Windermere, FL 34786

  ***Charming Windermere Home in Lakes of Windermere – Peachtree! ***Welcome to this beautifully maintained 3-bedroom, 2-bath single-story home located on a quiet cul-de-sac in the desirable Lakes of Windermere – Peachtree community, behind the famous Walt Disney World Magic Kingdom! This home combines comfort, convenience, and style in one of Central Florida’s most sought-after locations. Step

  Lynn London EXP REALTY LLC

  13430 Hopkinton Ct, Windermere, FL 34786
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  /76

  $5,950 per month

  • 4 Beds
  • 3.5 Baths
  • 3,268 Sq Ft
  • House for Rent

  6557 Crestmont Glen Ln, Windermere, FL 34786

  Welcome to your fully furnished dream home! This charming residence offers 4 spacious bedrooms, 3 full bathrooms, and 2 half baths, ideal for family living and entertaining. The open floor plan features a dedicated office and a versatile bonus room to suit your needs. Bright and airy, the home boasts high ceilings and abundant natural light. The expansive kitchen includes 42-inch cabinets, a

  Any Alves WRA BUSINESS & REAL ESTATE

  6557 Crestmont Glen Ln, Windermere, FL 34786
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  /2

  $3,600,000 Sold May 12, 2025

  11306 Bridge House Rd, Windermere, FL 34786

  • 5 Beds
  • 7 Baths
  • 6,742 Sq Ft
  • Built 2007

  Last Sold Summary

  • 10% Below List Price
  • $534/SF
  • 52 Days On Market

  Current Estimated Value $3,634,427

  Last Listing Agent Loren Williams LAKESIDE REALTY WINDERMERE INC

  11306 Bridge House Rd, Windermere, FL 34786
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  /56

  Est $2,580,212 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 5,524 Sq Ft

  13352 Bellaria Cir, Windermere, FL 34786

  13352 Bellaria Cir, Windermere, FL 34786
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  /55

  $2,375,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 4,688 Sq Ft

  409 W 2nd Ave, Windermere, FL 34786

  Under contract-accepting backup offers. Step inside this beautifully updated home where clean lines, soaring ceilings, and two-story windows fill every corner with natural light. A floating staircase makes a stunning first impression, while the spacious family room with its cozy fireplace is the perfect spot to gather with friends and family.The open living and dining room features built-ins

  Amanda Black PA UPSIDE REAL ESTATE INC

  409 W 2nd Ave, Windermere, FL 34786
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  /2

  $2,650 per month

  • 3 Beds
  • 2.5 Baths
  • 1,624 Sq Ft
  • Property for Rent

  11642 Water Run Aly, Windermere, FL 34786

  3 bedroom 2 bathroom townhouse.Ashlin Park is a peaceful community located in the beautiful town of Windermere. This neighborhood offers a community pool and clubhouse for your comfort and convenience. Ashlin Park is an ideal location due to its proximity to the Lakeside Shopping Center, many highly rated K-12 schools and Walt Disney World.1 Year Lease HOA Approval might be required.

  Rafael Izquierdo Lasaracina VS INTERNATIONAL PROPERTIES

  11642 Water Run Aly, Windermere, FL 34786
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  /2

  $742,000 Sold Jun 02, 2025

  12971 Westside Village Loop, Windermere, FL 34786

  • 5 Beds
  • 3.5 Baths
  • 3,694 Sq Ft
  • Built 2018

  Last Sold Summary

  • 1% Below List Price
  • $201/SF
  • 72 Days On Market

  Current Estimated Value $749,083

  Last Listing Agent Eric Jia NUMBER 1 BROKER, LLC

  12971 Westside Village Loop, Windermere, FL 34786
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  /23

  Est $452,419 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,912 Sq Ft

  13736 Bravante Aly, Windermere, FL 34786

  13736 Bravante Aly, Windermere, FL 34786
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  /12

  $1,004,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,783 Sq Ft

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

  The Tuttle is a two-story home offering four bedrooms, two full bathrooms, one half bathroom, and a two-car garage. The first-floor primary suite provides privacy and comfort. The spacious kitchen opens to a covered lanai, ideal for outdoor living and entertaining. Additional features include an oversized laundry room and an optional butler’s pantry to enhance functionality. Modern finishes,

  Ashton Woods Builder

  5432 Winter Garden Vineland Rd Unit 37932784, Windermere, FL 34786
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  /7

  $2,995 per month

  • 4 Beds
  • 2 Baths
  • 2,151 Sq Ft
  • House for Rent

  12921 Cragside Ln, Windermere, FL 34786

  Great rental opportunity in the Lakes of Windermere. 4 bedrooms and 2.5 bathrooms .2 car garage .Solid flooring throughout. Lawn service. Included . Pets allowed.

  Hans Welbergen WINDERMERE INTERNATIONAL REALTY

  12921 Cragside Ln, Windermere, FL 34786
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  /2

  $1,050,000 Sold Oct 31, 2025

  65 Oakdale St, Windermere, FL 34786

  • 4 Beds
  • 2 Baths
  • 2,191 Sq Ft
  • Built 1959

  Last Sold Summary

  • 12% Below List Price
  • $479/SF
  • 34 Days On Market

  Current Estimated Value $1,098,474

  Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

  65 Oakdale St, Windermere, FL 34786
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  /31

  Est $917,833 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,224 Sq Ft

  13542 Gorgona Isle Dr, Windermere, FL 34786

  13542 Gorgona Isle Dr, Windermere, FL 34786
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  /18

  $1,014,990 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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  /19

  $2,475 per month

  • 3 Beds
  • 2.5 Baths
  • 1,625 Sq Ft
  • Townhouse for Rent

  13075 Calderdale Ave, Windermere, FL 34786

  This beautiful 3-bedroom townhome is available for rent! The kitchen features granite countertops and stainless steel appliances, making it both functional and stylish. The first floor includes a spacious family room, dining area, convenient half bathroom, and a laundry room with a full-size washer and dryer. Upstairs, the primary suite offers dual sinks and a walk-in shower. Enjoy outdoor living

  Bekah Burke BELLA TRAE REALTY

  13075 Calderdale Ave, Windermere, FL 34786
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  /2

  $1,295,922 Sold Mar 31, 2025

  14207 Crest Palm Ave, Windermere, FL 34786

  • 6 Beds
  • 4 Baths
  • 4,222 Sq Ft
  • Built 2024

  Last Sold Summary

  • $307/SF
  • 0 Days On Market

  Current Estimated Value $1,277,000

  Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  14207 Crest Palm Ave, Windermere, FL 34786
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  Est $1,597,599 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,374 Sq Ft

  1146 Estancia Woods Loop, Windermere, FL 34786

  1146 Estancia Woods Loop, Windermere, FL 34786
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  /2

  $3,200,000

  • Land
  • 6.76 Acres
  • $473,373 per Acre

  934 Roberson Rd, Ocoee, FL 34761

  PROPERTY DESCRIPTION - We are pleased to present a premier investment opportunity at 934 Roberson Road in Ocoee, just west of Orlando. This 6.76-acre parcel of vacant land comes with full site plan approval from the City of Ocoee for a 120-bed assisted living facility, making it an exceptional prospect for those looking to capitalize on the burgeoning demand for senior care services in Central

  Chase Collier Eshenbaugh Land Company

  934 Roberson Rd, Ocoee, FL 34761
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  /45

  $2,900 per month

  • 3 Beds
  • 2.5 Baths
  • 2,203 Sq Ft
  • House for Rent

  13040 Overstreet Rd, Windermere, FL 34786

  Welcome to this gorgeous 3-bedroom, 2.5-bath single-family home located in the highly desirable Windermere area. Situated within top-rated school zones, this home offers both comfort and convenience. The kitchen features granite countertops and opens to a functional living space perfect for everyday living and entertaining. Lawn maintenance is included through the HOA, making maintenance

  Sherry Gao CHARLES RUTENBERG REALTY ORLANDO

  13040 Overstreet Rd, Windermere, FL 34786
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  /2

  $890,000 Sold Jul 31, 2025

  235 Oakdale St, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 2,562 Sq Ft
  • Built 1971

  Last Sold Summary

  • 11% Below List Price
  • $347/SF
  • 274 Days On Market

  Current Estimated Value $991,728

  Last Listing Agent Simon Simaan THE SIMON SIMAAN GROUP

  235 Oakdale St, Windermere, FL 34786
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  /26

  Est $327,874 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft

  11434 Jasper Kay Terrace Unit 208, Windermere, FL 34786

  11434 Jasper Kay Terrace Unit 208, Windermere, FL 34786
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  /18

  $428,000

  • 3 Beds
  • 2.5 Baths
  • 1,584 Sq Ft

  11636 Water Run Aly, Windermere, FL 34786

  This property is a beautifully maintained 3-bedroom, 2.5-bath townhouse located in the desirable Ashlin Park community of Windermere. Built in 2017, this home features an open-concept layout filled with natural light, a modern kitchen with quartz countertops, stainless steel appliances, and espresso cabinetry. The spacious primary suite offers a walk-in closet and an elegant ensuite bath. Enjoy a

  Jose Jimenez EXP REALTY LLC

  11636 Water Run Aly, Windermere, FL 34786
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  /23

  $2,095 per month

  • 2 Beds
  • 2 Baths
  • 1,161 Sq Ft
  • Condo for Rent

  8264 Maritime Flag St Unit 1419, Windermere, FL 34786

  Beautiful Lakeside at Lakes of Windermere 2nd floor 2 bedroom condo with an open floor open, 42" cabinets, under cabinet lighting, breakfast bar and crown molding. Master bedroom has a large walk in closet and the master bath comes with a large vanity and walk in shower. All appliances including washer and dryer are included, along with water, sewer and valet trash. World class amenities include

  Amanda Beckman RED DOOR INVESTMENT GRP LLC

  8264 Maritime Flag St Unit 1419, Windermere, FL 34786
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  /2

  $520,000 Sold Jun 26, 2025

  12880 Holdenbury Ln, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 3,103 Sq Ft
  • Built 2006

  Last Sold Summary

  • 13% Below List Price
  • $168/SF
  • 67 Days On Market

  Last Listing Agent Jacquie Sosa EXP REALTY LLC

  12880 Holdenbury Ln, Windermere, FL 34786
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  /53

  Est $1,092,089 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,934 Sq Ft

  11708 Hampstead St, Windermere, FL 34786

  11708 Hampstead St, Windermere, FL 34786
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  /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
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  /24

  $1,775 per month

  • 2 Beds
  • 2 Baths
  • 1,161 Sq Ft
  • Condo for Rent

  8168 Boat Hook Loop Unit 202, Windermere, FL 34786

  2/2 Windermere condo walking distance to the pool with resort style amenities. Kitchen has granite counter tops, 42" cabinets. Main suite has huge walk-in closet and bath has decorative tile, lighted shower and double sinks. Community features pavilion on the lake, screened patios, barbecue area and fitness center. Valet trash included. HOA app fee per person-15 day approval process.AS PER

  Andrea Thurman HAMPTON & HAMPTON MGMT LEASING

  8168 Boat Hook Loop Unit 202, Windermere, FL 34786
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  /2

  $650,000 Sold May 05, 2025

  4801 Breezy Palms Ct, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 1,996 Sq Ft
  • Built 1986

  Last Sold Summary

  • $326/SF
  • 1 Day On Market

  Current Estimated Value $644,648

  Last Listing Agent Luana Oliveira ORANGE SLICE PROPERTIES

  4801 Breezy Palms Ct, Windermere, FL 34786
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  /4

  Est $1,214,057 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,806 Sq Ft

  5819 Caymus Loop Unit 1, Windermere, FL 34786

  5819 Caymus Loop Unit 1, Windermere, FL 34786
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  /88

  $1,274,000 Pending

  • 5 Beds
  • 3.5 Baths
  • 3,689 Sq Ft

  12779 Westside Village Loop, Windermere, FL 34786

  Under contract-accepting backup offers. This exceptional residence offers a rare combination of contemporary design, smart technology, functionality, and lifestyle. Fully renovated and thoughtfully planned with meticulous attention to detail, the home showcases a high level of craftsmanship and a cohesive modern aesthetic throughout. Luxury vinyl flooring extends throughout the entire home,

  Ramon Brandão WEBB FLORIDA REALTY LLC

  12779 Westside Village Loop, Windermere, FL 34786
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  /18

  $4,500 per month

  • 5 Beds
  • 4 Baths
  • 3,536 Sq Ft
  • House for Rent

  1351 Glenwick Dr, Windermere, FL 34786

  POOL HOME!!! WITH MOTHER IN LAW SUIT!!! 5 BEDROOMS 4 FULL BATHS!!! MAN-GATED COMMUNITY IN WINDERMERE!!! Stunning Windermere home at 1351 Glenwick Dr! Spacious open floor plan, modern kitchen, and elegant finishes throughout. Perfect for entertaining or relaxing in the private backyard. Close to top schools, shopping, and dining. A must-see blend of luxury, comfort, and location!

  Adriana Montes MBA FLORIDA DREAMS REALTY GRP INC

  1351 Glenwick Dr, Windermere, FL 34786
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  /2

  $8,500,000 Sold Sep 05, 2025

  5271 Isleworth Country Club Dr, Windermere, FL 34786

  • 7 Beds
  • 13 Baths
  • 11,403 Sq Ft
  • Built 2013

  Last Sold Summary

  • 3% Below List Price
  • $745/SF
  • 206 Days On Market

  Current Estimated Value $8,275,956

  Last Listing Agent Monica Lochmandy ISLEWORTH REALTY LLC

  5271 Isleworth Country Club Dr, Windermere, FL 34786
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  /98

  Est $2,689,591 Not Listed For Sale

  • 5 Beds
  • 6.5 Baths
  • 5,390 Sq Ft

  13509 Bellaria Cir, Windermere, FL 34786

  13509 Bellaria Cir, Windermere, FL 34786
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  /63

  $1,650,000

  • 4 Beds
  • 4.5 Baths
  • 3,288 Sq Ft

  1703 Roberts Landing Rd, Windermere, FL 34786

  This elegant and fully renovated lakefront home on Lake Olivia in Windermere offers the ultimate blend of luxury, comfort, and Florida lifestyle. Featuring three master suites plus a guest bedroom and bathroom, the spacious layout is designed for both entertaining and everyday living. Large windows fill the home with natural light and frame breathtaking views of the water, while recent

  Wui Keong Goh INTERNATIONAL NETWORK REALTY

  1703 Roberts Landing Rd, Windermere, FL 34786
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  /53

  $3,800 per month

  • 3 Beds
  • 2.5 Baths
  • 1,988 Sq Ft
  • House for Rent

  7307 Ella Ln, Windermere, FL 34786

  Welcome to your new home!! Conveniently situated within the charming Windermere area, you'll find this gem House, fully furnished, 1-Master Suite, 2-bedrooms, 2 and 1/2 bathrooms, nestled within the Windermere Sound community. Opening the entry door (with a digital code locker), you will find a beautiful spacious living room, well decorated and plenty of natural light coming trough the double

  Sergio Figueiredo NOVA REAL ESTATE SERVICES INC

  7307 Ella Ln, Windermere, FL 34786
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  /2

  $480,000 Sold Sep 26, 2025

  13715 Bressler Aly, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,139 Sq Ft
  • Built 2019

  Last Sold Summary

  • 9% Below List Price
  • $224/SF
  • 215 Days On Market

  Current Estimated Value $481,189

  Last Listing Agent Irene Fort PREFERRED REAL ESTATE BROKERS

  13715 Bressler Aly, Windermere, FL 34786
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  /2

  Est $475,308 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,091 Sq Ft

  13701 Beckman Dr, Windermere, FL 34786

  13701 Beckman Dr, Windermere, FL 34786
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  /18

  $1,299,000

  • 5 Beds
  • 4 Baths
  • 3,557 Sq Ft

  11021 Hawkshead Ct Unit 2, Windermere, FL 34786

  Welcome to this exquisite 5-bedroom, 4-bathroom residence nestled on a premium corner lot in one of Windermere’s most beautiful, gated communities. Boasting 3,557 square feet of thoughtfully designed living space, this Spanish Colonial-style home blends timeless elegance with modern comfort. Step inside to discover spacious living areas, rich architectural details, and a seamless flow ideal for

  Kara Manuchia ALL REAL ESTATE & INVESTMENTS

  11021 Hawkshead Ct Unit 2, Windermere, FL 34786
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  /23

  $2,780 per month

  • 4 Beds
  • 3.5 Baths
  • 1,936 Sq Ft
  • Townhouse for Rent

  12337 Via Derna Place, Windermere, FL 34786

  Available now for quick move-in! This beautifully updated corner townhome offers 4 bedrooms, 3.5 bathrooms, and a versatile loft area, combining comfort, style, and an exceptional location. Freshly painted and featuring brand-new carpet throughout, the home welcomes you with an open-concept living space and a stunning kitchen equipped with granite countertops, stainless steel appliances, and a

  Sam Fernandes FLORIDA CONNEXION PROPERTIES

  12337 Via Derna Place, Windermere, FL 34786
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  /2

  $1,500,000 Sold Mar 03, 2025

  11769 Hampstead St, Windermere, FL 34786

  • 5 Beds
  • 4 Baths
  • 4,979 Sq Ft
  • Built 2016

  Last Sold Summary

  • 3% Below List Price
  • $301/SF
  • 12 Days On Market

  Current Estimated Value $1,489,301

  Last Listing Agent John Cunningham KELLER WILLIAMS CLASSIC

  11769 Hampstead St, Windermere, FL 34786
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  /30

  Est $2,518,161 Not Listed For Sale

  12624 Park Ave, Windermere, FL 34786

  12624 Park Ave, Windermere, FL 34786

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