Windermere, FL Homes

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  $1,224,000

  • 4 Beds
  • 3.5 Baths
  • 2,791 Sq Ft

  109 E 12th Ave, Windermere, FL 34786

  Modern sophistication and timeless Windermere charm come together in this fully reimagined residence located just steps from Lake Bessie and the heart of Windermere Town. Set on a beautifully landscaped corner lot with no HOA, this home offers a rare blend of luxury comfort and walkable small town living in one of Central Florida’s most desirable communities. Every detail has been thoughtfully

  Robert Larkan THE AGENCY FL

  109 E 12th Ave, Windermere, FL 34786
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  $3,500 per month

  • 4 Beds
  • 2.5 Baths
  • 2,623 Sq Ft
  • House for Rent

  7448 Ella Ln, Windermere, FL 34786

  Experience the perfect mix of elegance, comfort, and versatility in this 4-bedroom, 2.5-bathroom home in the Beautiful Windermere community. Step inside to discover this well maintained property with designed living spaces, open layouts from room to room. The spacious open-concept layout goes from the spacious and well equipped kitchen to the living and dining areas. The kitchen features granite

  Carmela Mazzilli LA ROSA REALTY LLC

  7448 Ella Ln, Windermere, FL 34786
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  $930,000 Sold Nov 10, 2025

  5141 Autumn Ridge Ln, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,390 Sq Ft
  • Built 1990

  Last Sold Summary

  • 2% Below List Price
  • $389/SF
  • 91 Days On Market

  Last Listing Agent Deb Schroeder INFINITY REALTY GROUP LLC

  5141 Autumn Ridge Ln, Windermere, FL 34786
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  /58

  Est $448,384 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,722 Sq Ft

  8668 Wellington Blue Ln, Windermere, FL 34786

  8668 Wellington Blue Ln, Windermere, FL 34786
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  $1,699,900

  • 4 Beds
  • 5 Baths
  • 4,329 Sq Ft

  13120 Zori Ln, Windermere, FL 34786

  Experience refined lakefront living in this exceptional Windermere residence, ideally positioned on Little Lake Sawyer. Set on an oversized homesite, this property offers a rare combination of privacy, natural beauty, and everyday luxury in one of Central Florida’s most desirable communities – Windermere. The home features an open, light-filled floor plan with expansive windows, sleek flooring,

  Matt Tomaszewski CORCORAN PREMIER REALTY

  13120 Zori Ln, Windermere, FL 34786
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  $2,887 per month

  • 4 Beds
  • 2.5 Baths
  • 1,766 Sq Ft
  • Townhouse for Rent

  8320 Iron Mountain Trail, Windermere, FL 34786

  Welcome to this beautifully updated townhouse in the highly sought-after Windermere, FL area, offering serene lake views and a peaceful, picturesque setting. This 4-bedroom, 2.5-bath home has been fully refreshed with new interior paint and modern vinyl flooring, creating a clean, stylish, and low-maintenance living space. The well-designed layout provides comfort and privacy, featuring a

  Jacob Hara TRANSCEND REALTY

  8320 Iron Mountain Trail, Windermere, FL 34786
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  /2

  $518,000 Sold May 14, 2025

  5014 Wise Bird Dr, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,342 Sq Ft
  • Built 2004

  Last Sold Summary

  • 13% Below List Price
  • $221/SF
  • 102 Days On Market

  Current Estimated Value $529,827

  Last Listing Agent Hong Lu CHARLES RUTENBERG REALTY ORLANDO

  5014 Wise Bird Dr, Windermere, FL 34786
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  Est $1,187,845 Not Listed For Sale

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

  5522 Remsen Cay Ln, Windermere, FL 34786

  5522 Remsen Cay Ln, Windermere, FL 34786
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  $1,750,000 Pending

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

  9922 Brentford Ct, Windermere, FL 34786

  Under contract-accepting backup offers. 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

  Shane Croft COLDWELL BANKER RESIDENTIAL RE

  9922 Brentford Ct, Windermere, FL 34786
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  $2,900 per month

  • 4 Beds
  • 2.5 Baths
  • 2,115 Sq Ft
  • House for Rent

  11842 Silverlake Park Dr, Windermere, FL 34786

  Welcome to this stunning 4-bedroom, 2.5-bath home located on a desirable corner lot in one of Windermere’s most sought-after communities. The open living and dining areas flow seamlessly, ideal for both everyday living and entertaining. Enjoy Florida living at its best in the private fenced backyard, featuring an outdoor BBQ area—perfect for weekend gatherings, family meals, or relaxing evenings

  Rosselyn Moux AGENT TRUST REALTY CORPORATION

  11842 Silverlake Park Dr, Windermere, FL 34786
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  $590,000 Sold Feb 27, 2025

  6518 Sawyer Shores Ln, Windermere, FL 34786

  • Land
  • 0.39 Acre
  • $1,512,821 per Acre

  Last Sold Summary

  • 9% Below List Price
  • 28 Days On Market

  Current Estimated Value $589,343

  Last Listing Agent Jodi Knapp REVEL REALTY LLC

  6518 Sawyer Shores Ln, Windermere, FL 34786
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  /2

  Est $2,599,164 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 5,320 Sq Ft

  9831 Grosvenor Pointe Cir, Windermere, FL 34786

  9831 Grosvenor Pointe Cir, Windermere, FL 34786
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  $1,875,000

  • 5 Beds
  • 4 Baths
  • 4,489 Sq Ft

  13420 Bonica Way, Windermere, FL 34786

  Experience the Florida lifestyle in this stunning FULLY FURNISHED 5-Bed/4-Bath pool home on over 1/2-acre, with a welcoming open floor plan spanning 4,500 square feet, spectacular Theater Room, custom upgrades and designer accents throughout, and new AC system in August 2025. Situated across from the community park and tennis on one of the best waterfront lots in sought-after gated Tildens Grove,

  Frank Ferrell FERRELL REALTY, INC.

  13420 Bonica Way, Windermere, FL 34786
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  /24

  $2,600 per month

  • 3 Beds
  • 2.5 Baths
  • 1,644 Sq Ft
  • Townhouse for Rent

  12958 Vennetta Way, Windermere, FL 34786

  Absolutely stunning 3BD/2.5BTH 1,644 sqft end unit townhome in Berkshire Park subdivision of Windermere! Prime location, centrally located, corner lot. Near Disney attractions and to the Winter Garden Village for shopping and dining. Property features ceramic tile on main floor, SS appliances, granite counter tops, just to name a few of the many upgrades. French doors leading out to private patio

  Fayola Adgar THE LISTING REAL ESTATE MANAGEMENT

  12958 Vennetta Way, Windermere, FL 34786
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  /2

  $745,000 Sold Jul 28, 2025

  9676 Wild Oak Dr, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,856 Sq Ft
  • Built 1977

  Last Sold Summary

  • 21% Below List Price
  • $261/SF
  • 102 Days On Market

  Current Estimated Value $776,050

  Last Listing Agent Hardy Edwards, III BHHS FLORIDA REALTY

  9676 Wild Oak Dr, Windermere, FL 34786
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  Est $3,481,726 Not Listed For Sale

  • 5 Beds
  • 6.5 Baths
  • 7,649 Sq Ft

  12300 Montalcino Cir, Windermere, FL 34786

  12300 Montalcino Cir, Windermere, FL 34786
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  $2,500,000

  • 4 Beds
  • 4.5 Baths
  • 4,961 Sq Ft

  13377 Lake Butler Blvd, Winter Garden, FL 34787

  Fantastic opportunity to purchase 12+ acres of private, quiet lake front property in Winter Garden/Windermere area on West Lake Butler Blvd. with 4+ acres high and dry and no HOA. Property currently boasts dock with electricity and boat lift on a skiable lake. There is an existing house that could be remodeled or torn down and start fresh. Home is 4961 square feet and built in 1990 with

  Dawn Briggs BLUE MAGNOLIA REALTY LLC

  13377 Lake Butler Blvd, Winter Garden, FL 34787
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  $3,700 per month

  • 4 Beds
  • 3.5 Baths
  • 2,931 Sq Ft
  • House for Rent

  8752 Powder Ridge Trail, Windermere, FL 34786

  Beautiful corner lot, Barret model, including 4 bedrooms, 3.5 bathrooms, huge extra room, living room, summer kitchen, and 2-car garage.The functional open floor plan allows for great entertaining.Stainless steel appliances.A-rated schools and the best area to live.Close to restaurants, markets, and major highways.This beautiful home will be available for rent starting January

  Tatiana Felice MS LAND & BUILDING LLC

  8752 Powder Ridge Trail, Windermere, FL 34786
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  $1,600,000 Sold Feb 10, 2025

  6550 Cartmel Ln, Windermere, FL 34786

  • 4 Beds
  • 4.5 Baths
  • 4,257 Sq Ft
  • Built 2004

  Last Sold Summary

  • 20% Below List Price
  • $376/SF
  • 10 Days On Market

  Current Estimated Value $1,900,190

  Last Listing Agent Leonardo Pereira CHARLES RUTENBERG REALTY ORLANDO

  6550 Cartmel Ln, Windermere, FL 34786
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  /23

  Est $334,090 Not Listed For Sale

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

  8264 Maritime Flag St Unit 1420, Windermere, FL 34786

  8264 Maritime Flag St Unit 1420, Windermere, FL 34786
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  $1,200,000

  • 7 Beds
  • 5 Baths
  • 4,751 Sq Ft

  6146 Golden Dewdrop Trail, Windermere, FL 34786

  MOVE-IN READY and thoughtfully upgraded, this spacious residence is located in the established Windermere Landing community and offers serene pond views, energy-efficient construction, and a flexible layout designed for modern living. From the moment you arrive, recent improvements are immediately apparent, including a FULL INTERIOR REPAINT, NEW LUXURY VINYL PLANK FLOORING throughout the main

  Simi Lakhani KELLER WILLIAMS CLASSIC

  6146 Golden Dewdrop Trail, Windermere, FL 34786
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  $4,332 per month

  • 4 Beds
  • 3 Baths
  • 2,738 Sq Ft
  • House for Rent

  2533 Ridgewind Way, Windermere, FL 34786

  4 Bedroom Home For Rent In Windermere3-Car Garage, Pool View, Screened-in Pool, Screened-in Patio, Master Bedrm Downstairs, Huge Master Suite, Huge Family Room, Hardwood Flooring, Tile in Wet Areas, Additional $150 charge for Pool Maintenance. The deposit amount is based upon the application results. Pets: OK - Medium 50lbs (Dangerous Pets are not permitted, Pit Bulls, etc.) Priced $3,999.00

  Jay Myers ORLANDO REALTY & PROPERTY MGNT

  2533 Ridgewind Way, Windermere, FL 34786
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  $585,000 Sold Aug 19, 2025

  8359 Lookout Pointe Dr, Windermere, FL 34786

  • 4 Beds
  • 4 Baths
  • 2,604 Sq Ft
  • Built 2016

  Last Sold Summary

  • 1% Below List Price
  • $225/SF
  • 3 Days On Market

  Current Estimated Value $550,035

  Last Listing Agent Pilar Fernandez SIX STAR REALTY GROUP LLC

  8359 Lookout Pointe Dr, Windermere, FL 34786
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  Est $353,468 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,371 Sq Ft

  8110 Enchantment Dr Unit 1704, Windermere, FL 34786

  8110 Enchantment Dr Unit 1704, Windermere, FL 34786
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  $1,176,990 Open Sat 1PM - 4PM

  • 6 Beds
  • 4 Baths
  • 3,550 Sq Ft

  14383 Crest Palm Ave, Windermere, FL 34786

  One or more photo(s) has been virtually staged. *Images shown are for illustrative purposes only* ELLINGTON II - Our beautiful huge 2 story home, with 6 Bedrooms and 4 Baths. This great floor plan boasts an open concept family/dining/kitchen area along with a formal dining room, gourmet kitchen, extended 42" cabinets and an extended island. Primary Suite on 1st floor along with an additional

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  14383 Crest Palm Ave, Windermere, FL 34786
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  /11

  $2,300 per month

  • 3 Beds
  • 2 Baths
  • 1,335 Sq Ft
  • Townhouse for Rent

  7708 Bexton Ln, Windermere, FL 34786

  Beautiful 3 bedroom 2.5 bath townhome located in Windermere! The home features an open kitchen with stainless steel appliances and beautiful 42" cabinets . Just off the dining area step out to the cozy fenced in courtyard. Upstairs there is a large master bedroom with walk in closet. The master bath features dual sinks and tiled walk in shower. There are 2 additional bedrooms on the second floor

  Reynaldo Izaguirre ALTIS REALTY

  7708 Bexton Ln, Windermere, FL 34786
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  /2

  $380,000 Sold Nov 13, 2025

  5219 Keenes Pheasant Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,461 Sq Ft
  • Built 2004

  Last Sold Summary

  • 1% Below List Price
  • $260/SF
  • 6 Days On Market

  Last Listing Agent Roland Cotardo THE SIMON SIMAAN GROUP

  5219 Keenes Pheasant Dr, Windermere, FL 34786
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  /31

  Est $375,929 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,786 Sq Ft

  8167 Enchantment Dr Unit 1501, Windermere, FL 34786

  8167 Enchantment Dr Unit 1501, Windermere, FL 34786
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  $1,174,935 Pending

  • 4 Beds
  • 3 Baths
  • 3,100 Sq Ft

  14250 Crest Palm Ave, Horizon West, FL 34786

  One or more photo(s) has been virtually staged. Under Construction. Sample Image Experience the perfect blend of elegance, comfort, and practicality with this beautifully crafted new home in Windermere. Every element of this residence has been thoughtfully designed to create a space that feels both luxurious and inviting. With soaring ceilings—up to 10 feet on the first floor and 9 feet on the

  Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  14250 Crest Palm Ave, Horizon West, FL 34786
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  $5,500 per month

  • 3 Beds
  • 2 Baths
  • 2,056 Sq Ft
  • House for Rent

  8447 Bowden Way, Windermere, FL 34786

  Welcome to Keenes Point - Windermere, a stunning 3-bedroom, 2-bathroom home located in the desirable Windermere, FL. This property is nestled within a secure gated community, offering an added layer of peace and security. The home boasts a private pool, perfect for cooling off during those hot Florida summers. The private backyard provides ample space for outdoor activities or simply enjoying the

  Julien Silva JOHN SILVA REALTY & ASSOCIATES

  8447 Bowden Way, Windermere, FL 34786
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  $475,000 Sold Sep 23, 2025

  5130 Sun Palm Dr, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,723 Sq Ft
  • Built 1987

  Last Sold Summary

  • 16% Below List Price
  • $276/SF
  • 23 Days On Market

  Current Estimated Value $492,104

  Last Listing Agent Elle Walters JASON MITCHELL REAL ESTATE FLO

  5130 Sun Palm Dr, Windermere, FL 34786
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  Est $2,885,377 Not Listed For Sale

  • 5 Beds
  • 6.5 Baths
  • 5,353 Sq Ft

  5054 Sawyer Cove Way, Windermere, FL 34786

  5054 Sawyer Cove Way, Windermere, FL 34786
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  $1,452,000

  • 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 Olmeda WRA BUSINESS & REAL ESTATE

  13596 Gorgona Isle Dr, Windermere, FL 34786
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  $3,950 per month

  • 5 Beds
  • 4 Baths
  • 2,800 Sq Ft
  • House for Rent

  9088 Outlook Rock Trail, Windermere, FL 34786

  One or more photo(s) has been virtually staged. The moment you step inside this 5-bedroom, 4-bath luxury home in the heart of Windermere—a rare opportunity for anyone relocating to the Orlando - is the moment you may change your mind about living anywhere else in Central Florida. This residence offers top-rated schools, tree-lined walking trails with sparkling lake views, a resort-style community

  Maria Serrano Whitehead EPIQUE REALTY, INC.

  9088 Outlook Rock Trail, Windermere, FL 34786
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  $484,000 Sold Jun 16, 2025

  12285 Joshua Tree Trail, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,149 Sq Ft
  • Built 2015

  Last Sold Summary

  • 15% Below List Price
  • $225/SF
  • 161 Days On Market

  Current Estimated Value $495,603

  Last Listing Agent Erin Legler CHARLES RUTENBERG REALTY ORLANDO

  12285 Joshua Tree Trail, Windermere, FL 34786
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  Est $346,759 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,534 Sq Ft

  14438 Desert Haven St Unit 4304, Windermere, FL 34786

  14438 Desert Haven St Unit 4304, Windermere, FL 34786
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  $1,298,000

  • 5 Beds
  • 4.5 Baths
  • 3,449 Sq Ft

  11333 Camden Park Dr Unit 7, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Nestled within highly sought after guard gated community, this exceptionally maintained two-story residence combines timeless elegance offering the ideal blend of style, comfort, and functionality. The home features 5 spacious bedrooms, 4.5 bathrooms, dinning room, separate living room from family room and a generously sized loft—ideal for a

  Cynthia Noto KARDOSH REALTY

  11333 Camden Park Dr Unit 7, Windermere, FL 34786
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  /16

  $3,550 per month

  • 4 Beds
  • 3.5 Baths
  • 2,770 Sq Ft
  • House for Rent

  13638 Ancilla Blvd, Windermere, FL 34786

  Discover this beautifully maintained two-story single-family home in the heart of Windermere, offering 4 spacious bedrooms, 2 full bathrooms, and a 2-car garage. With 2,770 sq/ft of living space and a total of 3,513 sq/ft, this property provides comfort, space, and functionality for today’s lifestyle. Enjoy Florida living at its best with your own private in-ground pool, perfect for relaxing or

  Jose Solano FUSION FLORIDA REALTY LLC

  13638 Ancilla Blvd, Windermere, FL 34786
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  /2

  $1,080,813 Sold Feb 28, 2025

  14291 Crest Palm Ave, Windermere, FL 34786

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

  Last Sold Summary

  • 1% Below List Price
  • $256/SF
  • 0 Days On Market

  Current Estimated Value $1,098,432

  Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  14291 Crest Palm Ave, Windermere, FL 34786
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  Est $1,450,420 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,493 Sq Ft

  1121 Estancia Woods Loop, Windermere, FL 34786

  1121 Estancia Woods Loop, Windermere, FL 34786

Showing Results 201 - 240, Page 6 of 18