Windermere, FL Homes

• 

  

  

  /13

  $2,200,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 3,994 Sq Ft

  1020 Oakdale St, Windermere, FL 34786

  Under contract-accepting backup offers. Under Construction. Extraordinary new construction estate by renowned builder Davila Homes, nestled in the heart of Downtown Windermere. Meticulously designed and artfully executed, this five-bedroom, four-and-a-half-bathroom residence offers 3,994 square feet of luxurious living space. From the moment you step inside, you're enveloped in elevated elegance,

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  1020 Oakdale St, Windermere, FL 34786
• 

  

  

  /17

  $2,300 per month

  • 3 Beds
  • 2 Baths
  • 1,332 Sq Ft
  • Condo for Rent

  8168 Boat Hook Loop Unit 707, Windermere, FL 34786

  Welcome to this move in ready condo in the desirable Lakeside at Lakes of Windermere. This unscale condo community has everything. This first floor 3 bed 2 bath unit is located just across the street from the community clubhouse and pool. With close proximity to the Lakeside Village for shops, restaurants and grocery store, and only 15 mins to Disney. The unit has only been occupied by one

  Mandy Morgan TEAM DONOVAN

  8168 Boat Hook Loop Unit 707, Windermere, FL 34786
• 

  

  /2

  $1,060,000 Sold Sep 11, 2025

  76 Oakdale St, Windermere, FL 34786

  • 3 Beds
  • 1.5 Baths
  • 2,011 Sq Ft
  • Built 1957

  Last Sold Summary

  • 18% Below List Price
  • $527/SF
  • 82 Days On Market

  Current Estimated Value $1,091,690

  Last Listing Agent Bill Martini BHHS FLORIDA REALTY

  76 Oakdale St, Windermere, FL 34786
• 

  

  /2

  Est $9,587,888 Not Listed For Sale

  • 6 Beds
  • 8 Baths
  • 14,856 Sq Ft

  9306 Blanche Cove Dr, Windermere, FL 34786

  9306 Blanche Cove Dr, Windermere, FL 34786
• 

  

  

  /73

  $5,900,000

  • 5 Beds
  • 6 Baths
  • 7,491 Sq Ft

  9826 Laurel Valley Dr, Windermere, FL 34786

  Tucked within the gates of Isleworth Golf Community and Country Club lies a residence that feels more like a private lakeside retreat than a home. Here, more than 7,000 square feet of elegance unfolds across a premium homesite on the shores of Lake Butler, where the water is clear, the sandy beach is pristine, and the sunsets spill across the horizon in dazzling color every evening.The

  Dianna Desboyaux EXP REALTY LLC

  9826 Laurel Valley Dr, Windermere, FL 34786
• 

  

  /46

  $4,500 per month

  • 6 Beds
  • 5.5 Baths
  • 3,389 Sq Ft
  • House for Rent

  4345 Saltmarsh Sparrow Dr, Windermere, FL 34786

  WELCOME HOME to Summerport! HUGE PRICE REDUCTION!! This stunning 6-bedroom, 5.5-bathroom residence is now available for rent in the highly desirable Summerport neighborhood—zoned for top-rated A+ schools!Step inside and enjoy a thoughtfully designed split two-story floor plan with plenty of room for family and entertaining. The first floor features a versatile office/den with French doors, a

  Silvia Odebrecht ICON REALTY ASSOCIATES INC

  4345 Saltmarsh Sparrow Dr, Windermere, FL 34786
• 

  /2

  $1,000,000 Sold Sep 03, 2025

  1947 Broadleaf Ct, Windermere, FL 34786

  • 5 Beds
  • 3.5 Baths
  • 3,646 Sq Ft
  • Built 1989

  Last Sold Summary

  • 20% Below List Price
  • $274/SF
  • 64 Days On Market

  Current Estimated Value $1,016,686

  Last Listing Agent Kevin Sullivan LAKESIDE REALTY WINDERMERE INC

  1947 Broadleaf Ct, Windermere, FL 34786
• 

  /2

  Est $333,290 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,512 Sq Ft

  14276 Desert Haven St Unit GE, Windermere, FL 34786

  14276 Desert Haven St Unit GE, Windermere, FL 34786
• 

  

  /4

  $395,000

  • 3 Beds
  • 2.5 Baths
  • 1,520 Sq Ft

  8638 Brookvale Dr, Windermere, FL 34786

  Great opportunity to own this wonderful townhouse in the beautiful Lake Reams community near Disney World! This townhouse features 3bedrooms, 2.5 bathrooms, a 2-car garage, and a spacious courtyard for outdoor gatherings, a fully equipped kitchen that opens up into a living room. All bedrooms are located upstairs for privacy. The primary bedroom offers high ceilings and a spacious walk-in

  Karina Aumaitre AK GLOBAL REALTY LLC

  8638 Brookvale Dr, Windermere, FL 34786
• 

  

  /12

  $2,695 per month

  • 3 Beds
  • 2 Baths
  • 2,023 Sq Ft
  • House for Rent

  13645 Riggs Way, Windermere, FL 34786

  Beautiful 3 bedroom one story beautiful home. This split plan home has a spacious great room which connects to the gourmet kitchen featuring beautiful granite countertops, a pantry with custom wood shelves, a breakfast bar and dinette area and provides the perfect space to spend time with family and friends. A set of French doors takes you out to your lanai and fenced backyard which extends your

  Jeff Li CINO INTERNATIONAL INC

  13645 Riggs Way, Windermere, FL 34786
• 

  /2

  $840,000 Sold Oct 17, 2025

  4509 Indian Deer Rd, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,412 Sq Ft
  • Built 2006

  Last Sold Summary

  • 1% Below List Price
  • $348/SF
  • 10 Days On Market

  Last Listing Agent Clementine Costantini KELLER WILLIAMS REALTY AT THE LAKES

  4509 Indian Deer Rd, Windermere, FL 34786
• 

  /2

  Est $831,127 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,092 Sq Ft

  11737 Sprawling Oak Dr, Windermere, FL 34786

  11737 Sprawling Oak Dr, Windermere, FL 34786
• 

  

  /44

  $389,900

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft

  7711 Fairgrove Ave, Windermere, FL 34786

  Walk On In and Call It Home! Welcome to this move in ready gem of a townhome in the sought-after Lake Sawyer South community in Windermere! This spacious home offers: 3 Bedrooms | 2.5 Bathrooms Over 1,600 Sq. Ft. of Living Space and a 2-Car Garage—big enough to store your boat! Fresh interior paint, Beautiful tile and wood flooring throughout. Located in the desirable Horizon West area of Orange

  Lindsay Kaye Voss VOSS REALTY INC

  7711 Fairgrove Ave, Windermere, FL 34786
• 

  

  /9

  $2,500 per month

  • 3 Beds
  • 2.5 Baths
  • 1,910 Sq Ft
  • Townhouse for Rent

  7452 Leighside Dr, Windermere, FL 34786

  Fantastic Location! Well Maintained Windermere townhome located in Lake Burden. Conveniently, Located to some of the Orlandos finest dinning and shopping areas. Also a quick drive to Winter Garden village, Disney World, Golf Courses and the up and coming Hamlin at Independence parkway. Home with 3 bedrooms and 2.5 baths, master bedroom is located downstairs with a walk in closet. OPEN floor plan

  Erik Lynch LJL REAL ESTATE, INC.

  7452 Leighside Dr, Windermere, FL 34786
• 

  /2

  $765,000 Sold Jan 10, 2025

  7336 Penkridge Ln, Windermere, FL 34786

  • 6 Beds
  • 3.5 Baths
  • 3,773 Sq Ft
  • Built 2015

  Last Sold Summary

  • 8% Below List Price
  • $203/SF
  • 86 Days On Market

  Current Estimated Value $777,042

  Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

  7336 Penkridge Ln, Windermere, FL 34786
• 

  

  /57

  Est $1,055,996 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 4,502 Sq Ft

  9245 Outlook Rock Trail, Windermere, FL 34786

  9245 Outlook Rock Trail, Windermere, FL 34786
• 

  

  /30

  $560,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,460 Sq Ft

  7011 Nobleton Dr, Windermere, FL 34786

  Under contract-accepting backup offers. Don't miss an Opportunity to own this Great Craftsman Home overlooking a serene Wooded View, located in the community of Lakes of Windermere. Impeccably maintained and Move-in ready, this 4-bedroom, 2.5-bath home offers numerous Upgrades and Touches throughout. Such as all new kitchen appliances, newly painted interior, new A/C, Hardwood flooring, Water

  Sean Flatley KELLER WILLIAMS REALTY AT THE PARKS

  7011 Nobleton Dr, Windermere, FL 34786
• 

  

  /28

  $4,150 per month

  • 4 Beds
  • 4 Baths
  • 3,144 Sq Ft
  • House for Rent

  11445 Vicolo Loop, Windermere, FL 34786

  Gorgeous pool home ready for tenant in desirable gated Belmere community with private pool and spa. Solid flooring throughout. Primary bedroom and additional bedrooms on first floor. Bonus room/bedroom and bath on second floor. 3 car garage; tile roof; paver driveway. Community has tennis, playground amenities and very walkable. Pool and lawncare included in rent. Bike ride to downtown Windermere

  Dawn Briggs BLUE MAGNOLIA REALTY LLC

  11445 Vicolo Loop, Windermere, FL 34786
• 

  /2

  $315,000 Sold Nov 14, 2025

  8271 Maritime Flag St Unit 109, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,363 Sq Ft
  • Built 2011

  Last Sold Summary

  • 12% Below List Price
  • $231/SF
  • 155 Days On Market

  Last Listing Agent Daniela de Rodriguez B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE

  8271 Maritime Flag St Unit 109, Windermere, FL 34786
• 

  

  /52

  Est $1,180,983 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,502 Sq Ft

  12169 Montalcino Cir, Windermere, FL 34786

  12169 Montalcino Cir, Windermere, FL 34786
• 

  

  /35

  $5,860,000

  • 4 Beds
  • 7 Baths
  • 7,872 Sq Ft

  12264 Montalcino Cir, Windermere, FL 34786

  Lakefront, Luxurious, Fully Furnished Home with Private Pool in Windermere.A True Paradise!Discover this rare gem in the heart of Windermere, located in the gated community of Casa Del Lago — a spectacular residence that combines sophistication, comfort, and stunning lake views. Fully furnished, with over eight expertly designed rooms, this home was carefully customized by the builder

  Jennifer Olmeda WRA BUSINESS & REAL ESTATE

  12264 Montalcino Cir, Windermere, FL 34786
• 

  

  /22

  $2,800 per month

  • 3 Beds
  • 2.5 Baths
  • 1,768 Sq Ft
  • Townhouse for Rent

  8620 Wellington Blue Ln, Windermere, FL 34786

  Beautiful townhome in Windermere Trails with first floor master bedroom. Excellent location - walking distance to Bay Lake Elementary, as well as shopping and dining. This well maintained unit offers 3 bedrooms (master down with 2 closets) and two bedrooms with full bath, bonus/loft area and laundry located on the second floor. Tastefully decorated throughout with gray and white accents. Kitchen

  Teresa Stewart SOUTHERN REALTY GROUP LLC

  8620 Wellington Blue Ln, Windermere, FL 34786
• 

  

  /32

  $575,000 Sold May 15, 2025

  5140 Honeynut Ln, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,819 Sq Ft
  • Built 1987

  Last Sold Summary

  • 4% Below List Price
  • $316/SF
  • 35 Days On Market

  Current Estimated Value $575,713

  Last Listing Agent Daniel Waldron MAINFRAME REAL ESTATE

  5140 Honeynut Ln, Windermere, FL 34786
• 

  /2

  Est $422,756 Not Listed For Sale

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

  11722 Water Run Aly, Windermere, FL 34786

  11722 Water Run Aly, Windermere, FL 34786
• 

  

  /20

  $410,000

  • 3 Beds
  • 2.5 Baths
  • 1,369 Sq Ft

  12744 Langstaff Dr, Windermere, FL 34786

  Beautiful townhouse located in Windermere, 3 br, 2.5 baths, full of natural lighting and unparalleled tranquility, featuring a private and fenced courtyard. Nice modern upgraded flooring and color scheme, new kitchen with quartz counter top, new hight in appliances, new AC. Beautiful Community pool and kiddie park. This home is so conveniently located close to Disney, mayor shopping & dining

  Ana Fermin PROPERTY WAREHOUSES OF AMERICA

  12744 Langstaff Dr, Windermere, FL 34786
• 

  

  /37

  $2,950 per month

  • 4 Beds
  • 2.5 Baths
  • 2,028 Sq Ft
  • Condo for Rent

  Unlisted Address

  Townhouse in gated community near Disney. furnished, 4 bed/2.5 bathroom 2 cars garage.Water, basic cable included.

  Adriana Amorim INT'L PROFESSIONAL REALTY INC

  Unlisted Address
• 

  /2

  $330,000 Sold Jul 16, 2025

  14320 Desert Haven St Unit 3906, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,840 Sq Ft
  • Built 2012

  Last Sold Summary

  • 3% Below List Price
  • $179/SF
  • 94 Days On Market

  Current Estimated Value $334,464

  Last Listing Agent Vicente Virgilio ALTIS REALTY

  14320 Desert Haven St Unit 3906, Windermere, FL 34786
• 

  

  /35

  Est $427,269 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,629 Sq Ft

  11716 Water Run Aly, Windermere, FL 34786

  11716 Water Run Aly, Windermere, FL 34786
• 

  

  /54

  $869,000

  • 4 Beds
  • 3.5 Baths
  • 3,270 Sq Ft

  8752 Lookout Pointe Dr, Windermere, FL 34786

  Experience the enchantment of a luxurious lifestyle with a home that offers elegance, comfort, and a touch of magic. Welcome to this breathtaking home where every day feels like a getaway, offering a serene water view right in your own backyard. This beautifully appointed Spanish style home boasts impressive curb appeal with its barrel tile roof, paver driveway, and a two car garage. As you

  Noor Masri LA ROSA REALTY PREMIER LLC

  8752 Lookout Pointe Dr, Windermere, FL 34786
• 

  

  /42

  $17,950 per month

  • 6 Beds
  • 8 Baths
  • 6,881 Sq Ft
  • House for Rent

  3999 Isabella Cir, Windermere, FL 34786

  AVAILABLE IN December - Exquisite Luxury Retreat in Prime Windermere Location Welcome to 3999 Isabella Cir, an architectural masterpiece nestled within the prestigious community of Casabella at Windermere, FL. This opulent estate is a true embodiment of refined living, offering a harmonious blend of elegant design, impeccable craftsmanship, and unparalleled comfort. Situated on an expansive half

  Lucas DeSouza DELUCA REAL ESTATE SERVICES CORP

  3999 Isabella Cir, Windermere, FL 34786
• 

  /2

  $320,000 Sold Jan 06, 2025

  8277 Maritime Flag St Unit 303, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,332 Sq Ft
  • Built 2007

  Last Sold Summary

  • 6% Below List Price
  • $240/SF
  • 167 Days On Market

  Current Estimated Value $321,413

  Last Listing Agent Beatriz Dominguez BROKERS REAL ESTATE GROUP INC

  8277 Maritime Flag St Unit 303, Windermere, FL 34786
• 

  /2

  Est $500,993 Not Listed For Sale

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

  6352 Golden Dewdrop Trail, Windermere, FL 34786

  6352 Golden Dewdrop Trail, Windermere, FL 34786
• 

  

  /27

  $401,990 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,554 Sq Ft

  8625 Coventry Park Way, Windermere, FL 34786

  Under contract-accepting backup offers. Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome located in the highly desirable Windermere Trails community! This spacious two-story home features a bright open floor plan and fresh interior paint throughout.The kitchen offers a chef kitchen, granite countertops, stainless steel appliances, and a large center island ideal for both

  Alexandra Mateu BAHIA INTERNATIONAL REALTY

  8625 Coventry Park Way, Windermere, FL 34786
• 

  

  /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
• 

  /2

  $845,000 Sold Jan 02, 2025

  13303 Fernow St, Windermere, FL 34786

  • 5 Beds
  • 5.5 Baths
  • 3,598 Sq Ft
  • Built 2007

  Last Sold Summary

  • 1% Below List Price
  • $235/SF
  • 14 Days On Market

  Current Estimated Value $828,770

  Last Listing Agent Li Xue AGENT GROUP REALTY

  13303 Fernow St, Windermere, FL 34786
• 

  

  /33

  Est $528,725 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,841 Sq Ft

  8553 Crescendo Ave, Windermere, FL 34786

  8553 Crescendo Ave, Windermere, FL 34786
• 

  

  /75

  $9,999,000

  • 6 Beds
  • 8 Baths
  • 6,783 Sq Ft

  6149 Grosvenor Shore Dr, Windermere, FL 34786

  Keene's Pointe - Stunning lakefront home on Lake Tibet of the famed Butler Chain of Lakes. No detail was spared in this completely renovated home boasting formal living and dining rooms, family and media room, 2 offices, 6 full/2 half baths and 6 bedrooms - one of which could serve as a in-law suite with separate entrance from the outside. From the moment you enter this impeccably designed home

  Teresa Stewart SOUTHERN REALTY GROUP LLC

  6149 Grosvenor Shore Dr, Windermere, FL 34786
• 

  

  /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
• 

  /2

  $418,000 Sold Jun 18, 2025

  11746 Water Run Aly, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,588 Sq Ft
  • Built 2016

  Last Sold Summary

  • 4% Below List Price
  • $263/SF
  • 10 Days On Market

  Current Estimated Value $417,017

  Last Listing Agent Kris Ibrahim HOME WISE REALTY GROUP, INC.

  11746 Water Run Aly, Windermere, FL 34786
• 

  /2

  Est $524,924 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,065 Sq Ft

  8308 Bryce Canyon Ave, Windermere, FL 34786

  8308 Bryce Canyon Ave, Windermere, FL 34786

Showing Results 321 - 360, Page 9 of 18