Windermere, FL Homes

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  /17

  $1,064,990

  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
• 

  

  

  /20

  $3,000 Per Month

  • 4 Beds
  • 2 Baths
  • 2,161 Sq Ft
  • House for Rent

  11732 Via Lucerna Cir, Windermere, FL 34786

  This 4 bed single story house ( 1 bedroom better suited as an office ) is located in the gated community of Belmere. The home has laminate flooring added so no carpet in the home at all. The property benefits from a formal sitting and dining area then opens up to kitchen family room overlooking the covered lanai at the rear. The home backs up to the community wall for a private garden. Belmere is

  Wendy Morris WENDY MORRIS REALTY

  11732 Via Lucerna Cir, Windermere, FL 34786
• 

  

  /2

  $966,400

  Sold Oct 17, 2025

  11508 Delwick Dr, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 3,206 Sq Ft
  • Built 2003

  Last Sold Summary

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

  Current Estimated Value $957,067

  Last Listing Agent Ziad El Aryan FLORIDA REALTY INVESTMENTS

  11508 Delwick Dr, Windermere, FL 34786
• 

  

  

  /40

  Est $534,598

  Not Listed For Sale

  12160 Canyon Sun Trail, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 2,184 Sq Ft
  • Built 2015

  12160 Canyon Sun Trail, Windermere, FL 34786

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Pilar Fernandez SIX STAR REALTY GROUP LLC
• 

  

  

  /35

  $420,000

  • 3 Beds
  • 2.5 Baths
  • 1,881 Sq Ft

  11425 Brownstone St, Windermere, FL 34786

  Location, lifestyle, and move-in-ready convenience come together in this beautifully maintained 3-bedroom, 2.5-bath townhome in the highly desirable Windermere/Lake Burden community. Perfectly positioned directly across from the community pool, this home offers the ideal combination of comfort, style, and resort-inspired living. A charming covered front porch welcomes you inside, where you'll

  Nicole Dege REDFIN CORPORATION

  11425 Brownstone St, Windermere, FL 34786
• 

  

  /47

  $2,900 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,231 Sq Ft
  • House for Rent

  13762 Summer Harbor Ct, Windermere, FL 34786

  Welcome to modern comfort and scenic views in this beautifully updated waterfront 3-bedroom, 2.5-bath residence located at 13762?Summer?Harbor?Court in the sought-after Summerport community of Windermere. Enjoy stunning pond views from your front porch and nightly Disney fireworks displays—all from the comfort of home.Step inside to find a fresh, move-in-ready interior featuring tile

  13762 Summer Harbor Ct, Windermere, FL 34786
• 

  /2

  $1,699,000

  Sold Mar 10, 2026

  13120 Zori Ln, Windermere, FL 34786

  • 4 Beds
  • 5 Baths
  • 4,329 Sq Ft
  • Built 2005

  Last Sold Summary

  • $392/SF
  • 2 Days On Market

  Current Estimated Value $1,678,458

  Last Listing Agent Matt Tomaszewski CORCORAN PREMIER REALTY

  13120 Zori Ln, Windermere, FL 34786
• 

  /2

  Est $576,856

  Not Listed For Sale

  11560 Ashlin Park Blvd, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,270 Sq Ft
  • Built 2015

  11560 Ashlin Park Blvd, Windermere, FL 34786

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent Matt Allen MATT ALLEN REAL ESTATE LLC
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  /43

  $1,755,000

  $5K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 4,219 Sq Ft

  1480 Hempel Ave, Windermere, FL 34786

  Welcome to this iconic Arthur Rutenberg custom estate offering 5 bedrooms, 4.5 baths, plus a private executive office with approximately 4,219 sq ft of refined living space on a rare 0.47-acre lot.Crafted with soaring ceilings, elegant tile flooring throughout the public areas, and rich hardwood floors in the bedrooms, custom millwork, plantation shutters, and designer marble and onyx

  Adriana Sanchez AROD PARTNERS REALTY

  1480 Hempel Ave, Windermere, FL 34786
• 

  /2

  $3,800 Per Month

  • 4 Beds
  • 3.5 Baths
  • 2,699 Sq Ft
  • House for Rent

  7332 Colbury Ave, Windermere, FL 34786

  welcome to this beautiful house, perfect for everyday livingBest area in WindermereReady to move in

  Fausto Correa AGENT TRUST REALTY CORPORATION

  7332 Colbury Ave, Windermere, FL 34786
• 

  /2

  $1,650,000

  Sold Feb 17, 2026

  9922 Brentford Ct, Windermere, FL 34786

  • 6 Beds
  • 4 Baths
  • 3,894 Sq Ft
  • Built 2000

  Last Sold Summary

  • 13% Below List Price
  • $424/SF
  • 164 Days On Market

  Current Estimated Value $1,675,682

  Last Listing Agent Shane Croft COLDWELL BANKER REALTY

  9922 Brentford Ct, Windermere, FL 34786
• 

  /2

  Est $782,771

  Not Listed For Sale

  13302 Roskin Ln, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,424 Sq Ft
  • Built 2011

  13302 Roskin Ln, Windermere, FL 34786

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Bruna Sereno SELECTA REALTY LLC
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  /14

  $1,097,990

  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
• 

  

  /21

  $2,800 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,552 Sq Ft
  • Townhouse for Rent

  8674 Wellington Blue Ln, Windermere, FL 34786

  Welcome to this beautiful and well-maintained 3-bedroom, 2.5-bathroom townhome, located in one of Windermere's most desirable communities. Offering the perfect blend of comfort, style, and convenience, this home is ideal for families and professionals alike. The spacious open floor plan features a bright living and dining area that flows seamlessly into a stunning gourmet kitchen with

  8674 Wellington Blue Ln, Windermere, FL 34786
• 

  

  /34

  $370,000

  Sold Jul 01, 2026

  14215 Desert Haven St, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,028 Sq Ft
  • Built 2012

  Last Sold Summary

  • 5% Below List Price
  • $182/SF
  • 24 Days On Market

  Last Listing Agent Brandi Crain Iron Valley R.E.Osceola

  14215 Desert Haven St, Windermere, FL 34786
• 

  

  /67

  Est $1,578,598

  Not Listed For Sale

  1220 Estancia Woods Loop, Windermere, FL 34786

  • 4 Beds
  • 5 Baths
  • 4,007 Sq Ft
  • Built 2018

  1220 Estancia Woods Loop, Windermere, FL 34786

  Last Sold Summary

  • 72 Days On Market

  Last Listing Agent Angela Rodriguez DREAM FINDERS REALTY GROUP CORP
• 

  

  /39

  $560,000

  Under Contract

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

  5125 Sun Palm Dr, Windermere, FL 34786

  Under contract-accepting backup offers. Virtually Staged. Welcome to this beautifully updated 3-bedroom, 2-bath home situated on an oversized lot in the established Silver Woods community of Windermere. The heart of the home is the spacious kitchen featuring solid wood cabinetry, stainless steel appliances, marble countertops, and an impressive center island offering plenty of workspace and

  Ashley Palata THE SIMON SIMAAN GROUP

  5125 Sun Palm Dr, Windermere, FL 34786
• 

  

  /30

  $2,300 Per Month

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

  11565 Mizzon Dr Unit 308, Windermere, FL 34786

  Location, Location!!!! Beautiful sought after condo in Windermere (Lakeside at Lakes of Windermere) minutes from Disney, shopping, golfing, great restaurants, excellent schools and so much more.Unit has been freshly painted, new carpets in bedroom and wood floors in main area. Screened porch. Split bedrooms and great size closets. Fantastic amenities include swimming pool, beach volleyball

  Lidya Gongage SPRING REALTY ORLANDO

  11565 Mizzon Dr Unit 308, Windermere, FL 34786
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  /65

  $1,100,000

  Sold Sep 09, 2026

  6443 Swanson St, Windermere, FL 34786

  • 5 Beds
  • 4 Baths
  • 3,971 Sq Ft
  • Built 2015

  Last Sold Summary

  • 11% Below List Price
  • $277/SF
  • 19 Days On Market

  Current Estimated Value $1,162,610

  Last Listing Agent Carlinhos Fregonezi TALENT REALTY SOLUTIONS

  6443 Swanson St, Windermere, FL 34786
• 

  

  /17

  Est $657,500

  Not Listed For Sale

  1348 Lake Olivia Ln, Windermere, FL 34786

  • Built 2018

  1348 Lake Olivia Ln, Windermere, FL 34786

  Last Sold Summary

  • 530 Days On Market

  Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC
• 

  Price To Be Determined

  New Construction

  • 6 Beds
  • 6.5 Baths
  • 6,996 Sq Ft

  Montech Plan at Saddlecrest at Windermere, Windermere, FL

  The Montech's impressive two-story covered entry flows into the two-story main indoor and outdoor living areas, revealing the lovely foyer, dining room, living room with coffered ceiling, and desirable lanai. The well-appointed kitchen overlooks a bright casual dining area, and is enhanced by a large center island with breakfast bar, ample counter and cabinet space, and huge walk-in pantry. The

  Toll Brothers, Inc. Builder

  1841 Windermere Rd Unit 41281965, Windermere, FL
• 

  

  /16

  $2,900 Per Month

  • 3 Beds
  • 3 Baths
  • 1,891 Sq Ft
  • Townhouse for Rent

  8615 Via Trieste Dr, Windermere, FL 34786

  Luxury townhouse in desired upscale Carrington community in Windermere. Lots of upgrades. Modern living. Features: tile thru out first floor, granite counter tops, 42" kitchen cabinets with molding, open floor plan, bedroom downstairs with full bathroom, access to beautiful balcony thru master bedroom, loft upstairs, Court yard between 2 car garage. Community features Cabana house and Pool. RATED

  8615 Via Trieste Dr, Windermere, FL 34786
• 

  /2

  $330,000

  Sold Oct 22, 2025

  11565 Mizzon Dr Unit 208, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft
  • Built 2006

  Last Sold Summary

  • 6% Below List Price
  • $229/SF
  • 10 Days On Market

  Current Estimated Value $329,156

  Last Listing Agent Gisele Abrantes Trautman LARTOK LLC

  11565 Mizzon Dr Unit 208, Windermere, FL 34786
• 

  /2

  Est $522,762

  Not Listed For Sale

  6315 Golden Dewdrop Trail, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,984 Sq Ft
  • Built 2012

  6315 Golden Dewdrop Trail, Windermere, FL 34786

  Last Sold Summary

  • 46 Days On Market

  Last Listing Agent Sandy Jones CLOCK TOWER REALTY
• 

  

  /38

  $699,900

  $50K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,665 Sq Ft

  6363 Sedona Leaf Ct, Windermere, FL 34786

  Virtually Staged. Welcome to this beautifully maintained 4-bedroom, 3-bathroom home tucked away on a quiet cul-de-sac in the highly desirable Eden Isle community of Windermere. Offering 2,665 square feet of thoughtfully designed living space on an oversized .32-acre lot, this home combines comfort, functionality, and an unbeatable location.Step inside to discover a light and inviting

  Abby Nelson RE/MAX 200 REALTY

  6363 Sedona Leaf Ct, Windermere, FL 34786
• 

  

  /15

  $2,800 Per Month

  • 3 Beds
  • 3 Baths
  • 1,584 Sq Ft
  • Townhouse for Rent

  13483 Gorgona Isle Dr, Windermere, FL 34786

  ?? Townhome for Rent in Windermere, FL? Legado Community – WindermereGreat opportunity to live in one of the most desirable areas in Central Florida! ? The rent includes HOA, property taxes, and lawn maintenance.Beautiful community with an excellent location, close to Winter Garden, Disney, restaurants, shopping, and top-rated schools in the area.Perfect for families looking for

  Eduardo Angulo IAD REAL ESTATE

  13483 Gorgona Isle Dr, Windermere, FL 34786
• 

  /2

  $2,335,000

  Sold Jun 10, 2026

  105 Pine St, Windermere, FL 34786

  • 5 Beds
  • 5.5 Baths
  • 5,696 Sq Ft
  • Built 2015

  Last Sold Summary

  • 7% Below List Price
  • $410/SF
  • 9 Days On Market

  Current Estimated Value $2,366,463

  Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

  105 Pine St, Windermere, FL 34786
• 

  /2

  Est $3,113,683

  Not Listed For Sale

  4124 Isabella Cir, Windermere, FL 34786

  • 6 Beds
  • 8 Baths
  • 6,842 Sq Ft
  • Built 2016

  4124 Isabella Cir, Windermere, FL 34786

  Last Sold Summary

  • 59 Days On Market

  Last Listing Agent Sean Flatley KELLER WILLIAMS REALTY AT THE PARKS
• 

  

  /22

  $399,900

  $20K PRICE DROP Pending

  • 3 Beds
  • 2.5 Baths
  • 1,468 Sq Ft

  7361 Brightland St, Windermere, FL 34786

  Under contract-accepting backup offers. New Price! Nestled in the heart of Windermere, this two-story townhome is a perfect blend of charm, comfort, and modern living. As you approach, the cute front porch entrance welcomes you, hinting at the warmth that lies within. The exterior is adorned with stone columns and crowned with a stylish barrel-tiled roof, adding character to this inviting abode.

  Peter Luu REAL BROKER, LLC

  7361 Brightland St, Windermere, FL 34786
• 

  

  /12

  $3,500 Per Month

  • 4 Beds
  • 3.5 Baths
  • 2,650 Sq Ft
  • House for Rent

  12928 Westside Vlg Lp, Windermere, FL 34786

  Located in the highly desirable heart of Windermere, Westside Village is only minutes from access to multiple lakes, dining, shopping, and A-rated schools. Westside Village will also have fantastic community amenities including a resort-style pool, clubhouse, and playground. energy-efficient home feature open floor plan. The main floor features an open kitchen island work area overlooking

  12928 Westside Vlg Lp, Windermere, FL 34786
• 

  /2

  $280,000

  Sold Jul 17, 2026

  8179 Maritime Flag St Unit 206, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,332 Sq Ft
  • Built 2006

  Last Sold Summary

  • 1% Below List Price
  • $210/SF
  • 3 Days On Market

  Current Estimated Value $289,030

  Last Listing Agent Diana Perez PROFESSIONAL REAL ESTATE TEAM

  8179 Maritime Flag St Unit 206, Windermere, FL 34786
• 

  

  /43

  Est $544,628

  Not Listed For Sale

  11650 Black Rail St, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,139 Sq Ft
  • Built 2012

  11650 Black Rail St, Windermere, FL 34786

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Julie Fernandez OAK AVENUE REAL ESTATE LLC
• 

  

  /15

  $1,001,990

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,226 Sq Ft

  Plant at Lake Cawood Cove - Traditional, Windermere, FL 34786

  The Plant is a one-story home offering three bedrooms, two full bathrooms, one half bathroom, and a two-car garage. The spacious kitchen features a large island and flows seamlessly into the dining and family rooms. A private primary suite includes a walk-in closet, while a generously sized den and covered lanai provide versatile living spaces for work, relaxation, and outdoor enjoyment. Modern

  Ashton Woods Builder

  5432 Winter Garden Vineland Rd Unit 37932781, Windermere, FL 34786
• 

  

  /22

  $2,950 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,476 Sq Ft
  • House for Rent

  14205 Bridgewater Crossings Blvd, Windermere, FL 34786

  Enjoy the tranquility of the Summerport community surrounded by lakes and beautiful landscaping, located near attractions and main access roads in desirable Windermere. This Community offers a pool, lakes, playgrounds, tennis courts, a fitness center, and trails. This is a 4 bedrooms 2.5 bathrooms, two-story home with a rear 2- car garage, stainless steel appliances, Corian countertops, and new

  Lisa Ingram INGRAM REALTY SERVICES LLC

  14205 Bridgewater Crossings Blvd, Windermere, FL 34786
• 

  /2

  $835,000

  Sold Aug 19, 2026

  9225 Mcdavid Ct, Windermere, FL 34786

  • 4 Beds
  • 2 Baths
  • 2,713 Sq Ft
  • Built 1984

  Last Sold Summary

  • 4% Above List Price
  • $308/SF
  • 3 Days On Market

  Current Estimated Value $804,238

  Last Listing Agent Milton James COLDWELL BANKER REALTY

  9225 Mcdavid Ct, Windermere, FL 34786
• 

  

  /59

  Est $2,713,589

  Not Listed For Sale

  13340 Bellaria Cir, Windermere, FL 34786

  • 6 Beds
  • 8 Baths
  • 6,803 Sq Ft
  • Built 2015

  13340 Bellaria Cir, Windermere, FL 34786

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Matt Tomaszewski CORCORAN PREMIER REALTY
• 

  $545,490

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,699 Sq Ft

  Cawood Plan at Lake Cawood Cove - Townhomes, Windermere, FL 34786

  Ashton Woods Builder

  5432 Winter Garden Vineland Rd Unit 37932780, Windermere, FL 34786
• 

  

  /15

  $2,950 Per Month

  • 4 Beds
  • 2 Baths
  • 2,074 Sq Ft
  • House for Rent

  12986 Holdenbury Ln, Windermere, FL 34786

  Discover this stunning 4-bedroom, 2-bathroom home nestled in the desirable Windermere Terrace neighborhood. The open-concept layout is flooded with natural light thanks to expansive windows, highlighting the beautiful tile flooring throughout. The modern kitchen features elegant granite countertops, all-black appliances, and ample cabinet and counter space, making it perfect for cooking and

  12986 Holdenbury Ln, Windermere, FL 34786
• 

  /2

  $485,000

  Sold Sep 24, 2025

  7837 Berkshire Oak Aly, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,904 Sq Ft
  • Built 2018

  Last Sold Summary

  • 1% Below List Price
  • $255/SF
  • 3 Days On Market

  Current Estimated Value $496,979

  Last Listing Agent Cara Edwards ALL REAL ESTATE & INVESTMENTS

  7837 Berkshire Oak Aly, Windermere, FL 34786
• 

  

  /64

  Est $793,549

  Not Listed For Sale

  12851 Westside Village Loop, Windermere, FL 34786

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

  12851 Westside Village Loop, Windermere, FL 34786

  Last Sold Summary

  • 94 Days On Market

  Last Listing Agent Torey Eisenman BENCHMARK REAL ESTATE GRP INC

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