Windermere, FL Homes

• 

  

  /2

  $1,098,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,404 Sq Ft

  7019 Windy Palm Way, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Sample Image The Baldwin is a beautifully designed two-story home offering 4 bedrooms, 3.5 baths, and over 3,400 square feet of living space. The open-concept main level features a spacious great room and dining area that flow seamlessly into the kitchen—perfect for family gatherings or entertaining. The first-floor owner’s suite includes a private

  

  Cindy Sapp

  OLYMPUS EXECUTIVE REALTY INC

  (689) 600-1926

  7019 Windy Palm Way, Windermere, FL 34786
• 

  

  

  /30

  $3,949 per month

  • 5 Beds
  • 4 Baths
  • 3,256 Sq Ft
  • House for Rent

  8931 Lookout Pointe Dr, Windermere, FL 34786

  - $4,100/month for a 1 year lease- $3,999 for an 18 month lease- $3,949 for a 24 month leaseThis 5/4 2 story home with a Bonus room located in Windemere Trails is just over 3200 sq ft. Downstairs is one bedroom and one full bathroom, separate dining and living room, and large eat-in kitchen. The upgraded kitchen has gorgeous granite counters with, lots of counter space, solid

  8931 Lookout Pointe Dr, Windermere, FL 34786
• 

  

  /2

  $1,450,000 Sold Aug 13, 2025

  8430 Woburn Ct, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,319 Sq Ft
  • Built 1999

  Last Sold Summary

  • 3% Below List Price
  • $437/SF
  • 64 Days On Market

  Current Estimated Value $1,432,713

  Last Listing Agent Mauricio Penha VOLKE REAL ESTATE LLC

  8430 Woburn Ct, Windermere, FL 34786
• 

  

  /2

  Est $1,349,579 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 4,908 Sq Ft

  17550 Black Rail St, Windermere, FL 34786

  17550 Black Rail St, Windermere, FL 34786
• 

  

  

  /93

  $2,500,000 Pending

  • 6 Beds
  • 6.5 Baths
  • 6,000 Sq Ft

  1724 Windermeredown Place, Windermere, FL 34786

  Under contract-accepting backup offers. Private Resort Luxury with Butler Chain Access in Windermere Downs Set within one of Windermere’s most sought-after lakefront communities, this extraordinary residence offers exclusive access to the Butler Chain of Lakes. Situated on over an acre, the estate blends handcrafted design, advanced technology, and magazine-featured architecture to deliver a

  Chad Going SERHANT

  1724 Windermeredown Place, Windermere, FL 34786
• 

  

  /68

  $3,500 per month

  • 3 Beds
  • 2.5 Baths
  • 1,980 Sq Ft
  • House for Rent

  6060 Roseate Spoonbill Dr, Windermere, FL 34786

  Welcome to this beautifully maintained 3-bedroom, 2.5-bath home situated on a desirable corner lot in the highly sought-after community of Windermere Landings. Located right off Chase Road, this prime Windermere location offers exceptional walkability—just steps from Sunset Park Elementary, Walgreens, Papa John’s, and other neighborhood conveniences. This is truly an ideal community for families

  Mulcy Tenorio FLORIDA CONNEXION PROPERTIES

  6060 Roseate Spoonbill Dr, Windermere, FL 34786
• 

  /2

  $670,000 Sold Nov 14, 2025

  2015 Woody Dr, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 2,042 Sq Ft
  • Built 1978

  Last Sold Summary

  • 4% Below List Price
  • $328/SF
  • 28 Days On Market

  Last Listing Agent Darrell Nunnelley VINTAGE REALTY GROUP LLC

  2015 Woody Dr, Windermere, FL 34786
• 

  

  /34

  Est $524,970 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,058 Sq Ft

  13335 Overstreet Rd, Windermere, FL 34786

  13335 Overstreet Rd, Windermere, FL 34786
• 

  

  /56

  $615,000

  • 3 Beds
  • 3.5 Baths
  • 2,720 Sq Ft

  6626 Bridgewater Village Rd, Windermere, FL 34786

  --Beautiful Corner-Lot Home in The Vineyards of Horizons West-- Welcome to one of Horizon West’s most desirable neighborhoods — where scenic parks, walkable streets, and friendly neighbors create a true sense of community. This corner-lot home sits across from a peaceful green space and offers the perfect blend of comfort, style, and outdoor living.From the moment you arrive, the inviting

  David Dorman CENTURY 21 CARIOTI

  6626 Bridgewater Village Rd, Windermere, FL 34786
• 

  

  /20

  $2,860 per month

  • 4 Beds
  • 2 Baths
  • 2,022 Sq Ft
  • House for Rent

  1314 Glenwick Dr, Windermere, FL 34786

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $3004.90. That covers your base rent, $2860.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  1314 Glenwick Dr, Windermere, FL 34786
• 

  /2

  $550,000 Sold Sep 30, 2025

  5238 Beach River Rd, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,414 Sq Ft
  • Built 2004

  Last Sold Summary

  • $228/SF
  • 3 Days On Market

  Last Listing Agent Liza Farzati SERHANT

  5238 Beach River Rd, Windermere, FL 34786
• 

  

  /30

  Est $546,288 Not Listed For Sale

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

  6442 Golden Dewdrop Trail, Windermere, FL 34786

  6442 Golden Dewdrop Trail, Windermere, FL 34786
• 

  

  /63

  $1,075,000

  • 4 Beds
  • 3 Baths
  • 2,743 Sq Ft

  2125 Kane Park Way, Windermere, FL 34786

  Welcome to this beautifully updated residence on one of the largest lots in the highly sought-after Willows at Lake Rhea in Windermere. Set on a 0.71-acre cul-de-sac lot surrounded by lush landscaping, the home offers exceptional privacy and a tranquil setting. Custom built by renowned local builder Richard Watson, known for his craftsmanship, thoughtful design, and quality construction, this

  Deb Schroeder INFINITY REALTY GROUP LLC

  2125 Kane Park Way, Windermere, FL 34786
• 

  

  /21

  $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
• 

  /2

  $2,625,000 Sold Feb 07, 2025

  5379 Isleworth Country Club Dr, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,872 Sq Ft
  • Built 1989

  Last Sold Summary

  • 12% Below List Price
  • $678/SF
  • 363 Days On Market

  Current Estimated Value $2,614,869

  Last Listing Agent Andrew Burgard CHARLES RUTENBERG REALTY ORLANDO

  5379 Isleworth Country Club Dr, Windermere, FL 34786
• 

  

  /22

  Est $1,062,424 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,117 Sq Ft

  12525 Montalcino Cir, Windermere, FL 34786

  12525 Montalcino Cir, Windermere, FL 34786
• 

  

  /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
• 

  

  /10

  $3,595 per month

  • 4 Beds
  • 3 Baths
  • 3,058 Sq Ft
  • House for Rent

  11530 Vicolo Loop, Windermere, FL 34786

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $3739.90. That covers your base rent, $3595.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  11530 Vicolo Loop, Windermere, FL 34786
• 

  /2

  $1,655,000 Sold Aug 15, 2025

  1424 Kelso Blvd, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 3,104 Sq Ft
  • Built 1975

  Last Sold Summary

  • 12% Below List Price
  • $533/SF
  • 112 Days On Market

  Current Estimated Value $1,717,308

  Last Listing Agent Carmen Aridas RE/MAX PRIME PROPERTIES

  1424 Kelso Blvd, Windermere, FL 34786
• 

  

  /40

  Est $553,065 Not Listed For Sale

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

  12160 Canyon Sun Trail, Windermere, FL 34786

  12160 Canyon Sun Trail, Windermere, FL 34786
• 

  

  /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
• 

  

  /16

  $3,990 per month

  • 3 Beds
  • 2 Baths
  • 1,784 Sq Ft
  • House for Rent

  415 E 6th Ave, Windermere, FL 34786

  Welcome to Windermere Living at Its Finest!Experience comfort, style, and true Florida living in this beautifully updated 3-bedroom, 2-bath home located at 415 E 6th Ave in the heart of Windermere. This inviting residence offers luxury vinyl flooring throughout, stylish tile in the bathrooms, and an open, airy layout designed for both relaxation and entertaining. Step outside to your own

  Irene Fort PREFERRED REAL ESTATE BROKERS

  415 E 6th Ave, Windermere, FL 34786
• 

  /2

  $718,000 Sold Oct 20, 2025

  12755 Westside Village Loop, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,064 Sq Ft
  • Built 2018

  Last Sold Summary

  • 12% Below List Price
  • $234/SF
  • 142 Days On Market

  Last Listing Agent Eric Jia NUMBER 1 BROKER, LLC

  12755 Westside Village Loop, Windermere, FL 34786
• 

  

  /40

  Est $649,220 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,208 Sq Ft

  7230 Rambling Water Way, Windermere, FL 34786

  7230 Rambling Water Way, Windermere, FL 34786
• 

  

  /9

  $944,990 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
• 

  

  /20

  $2,700 per month

  • 3 Beds
  • 2.5 Baths
  • 1,920 Sq Ft
  • Townhouse for Rent

  11320 Jasper Kay Terrace, Windermere, FL 34786

  Property Id: 2261362MOVE IN READY!!Welcome to this beautiful end-unit townhome in the desirable Lake Burden community of Windermere. Featuring 3 bedrooms plus an office, 2.5 baths, and a 1.5-car garage, this home offers abundant natural light and a clean, modern layout perfect for today's lifestyle.Key Features- End-unit with tons of natural light- 3 bedrooms +

  11320 Jasper Kay Terrace, Windermere, FL 34786
• 

  /2

  $3,100,000 Sold Apr 01, 2025

  2812 Marquesas Ct, Windermere, FL 34786

  • 4 Beds
  • 5 Baths
  • 5,624 Sq Ft
  • Built 1984

  Last Sold Summary

  • 2% Below List Price
  • $551/SF
  • 55 Days On Market

  Current Estimated Value $2,920,764

  Last Listing Agent Kari Fleck THE REAL ESTATE COLLECTION LLC

  2812 Marquesas Ct, Windermere, FL 34786
• 

  

  /49

  Est $1,377,982 Not Listed For Sale

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

  1152 Estancia Woods Loop, Windermere, FL 34786

  1152 Estancia Woods Loop, Windermere, FL 34786
• 

  

  /16

  $954,990 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
• 

  

  /30

  $2,700 per month

  • 3 Beds
  • 2.5 Baths
  • 1,881 Sq Ft
  • Townhouse for Rent

  7601 Ripplepointe Way, Windermere, FL 34786

  Live in one of Windermere’s most desirable communities! You cannot miss this lovely and beautifully maintained townhome in Windermere, Lake Burden. Spacious 3 bedroom, 3 1/2 bath with modern paint color at the walls, and ceramic flooring downstairs. Extra space at the first floor that could be used as office, TV room or play area. Amazing storage spaces, and all windows with blinds. Large open

  Ana Paula Teixeira ANA TEIXEIRA REALTY

  7601 Ripplepointe Way, Windermere, FL 34786
• 

  

  /64

  $600,000 Sold Mar 07, 2025

  426 E 6th Ave, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,698 Sq Ft
  • Built 1976

  Last Sold Summary

  • 22% Below List Price
  • $353/SF
  • 124 Days On Market

  Current Estimated Value $580,927

  Last Listing Agent Jaime Leizan EXP REALTY LLC

  426 E 6th Ave, Windermere, FL 34786
• 

  /2

  Est $755,091 Not Listed For Sale

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

  13302 Roskin Ln, Windermere, FL 34786

  13302 Roskin Ln, Windermere, FL 34786
• 

  

  /50

  $695,000

  • 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
• 

  

  /18

  $2,500 per month

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

  12974 Vennetta Way, Windermere, FL 34786

  Property Id: 2161517NO Carpet!! Well-maintained 3b/2.5b Townhome in Windermere with brand new luxury vinyl floor! Spacious bedrooms with walk-in closet. Two car garage. Private courtyard. Granite countertop. Quiet and friendly neighborhood features tennis court, community pool and playground. Zoned for great schools. Lawn maintenance is included.

  12974 Vennetta Way, 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

  Last Listing Agent Ziad El Aryan FLORIDA REALTY INVESTMENTS

  11508 Delwick Dr, Windermere, FL 34786
• 

  

  /67

  Est $1,545,455 Not Listed For Sale

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

  1220 Estancia Woods Loop, Windermere, FL 34786

  1220 Estancia Woods Loop, Windermere, FL 34786
• 

  

  /50

  $885,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 2,115 Sq Ft

  416 Magnolia St, Windermere, FL 34786

  Under contract-accepting backup offers. Step into a storybook cottage tucked in the heart of Windermere, where history whispers through every room and morning light dances across original 1915 details. Part of the early homestead still remains, giving this home a charm that simply can’t be recreated.The family room feels like a cozy tale come to life with its high ceilings, original wood

  Judy Black UPSIDE REAL ESTATE INC

  416 Magnolia St, Windermere, FL 34786
• 

  

  /39

  $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
• 

  /2

  $1,320,000 Sold May 20, 2025

  9178 Panzani Place, Windermere, FL 34786

  • 5 Beds
  • 5.5 Baths
  • 5,080 Sq Ft
  • Built 2004

  Last Sold Summary

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

  Current Estimated Value $1,334,050

  Last Listing Agent Melanie Miller PREMIUM PROPERTIES R.E SERVICE

  9178 Panzani Place, Windermere, FL 34786
• 

  

  /17

  Est $777,221 Not Listed For Sale

  1348 Lake Olivia Ln, Windermere, FL 34786

  1348 Lake Olivia Ln, Windermere, FL 34786

Showing Results 81 - 120, Page 3 of 18