Windermere, FL Homes

• 

  

  

  /35

  $849,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,771 Sq Ft

  1735 Maple Leaf Dr, Windermere, FL 34786

  Under contract-accepting backup offers. Located in the peaceful setting of oak-lined streets of the sought after Windermere Downs community, this well-maintained home offers recent upgrades, generous living spaces, and access to the renowned Butler Chain of Lakes. The home features a fully fenced, large backyard with privacy fencing and a large 35’+ pool with expansive deck area—ideal for outdoor

  Frank Del Toro REVEL REALTY LLC

  1735 Maple Leaf Dr, Windermere, FL 34786
• 

  

  

  /14

  $3,100 per month

  • 3 Beds
  • 2.5 Baths
  • 2,043 Sq Ft
  • House for Rent

  7241 Sunny Meadow Aly, Windermere, FL 34786

  This beautiful single-family residence FOR RENT offers the perfect combination of modern comfort and resort-style living. Great floorpan featuring 3 Bedrooms, 2-1/2 Bathroons and a great office. From the moment you arrive, you'll be captivated by the inviting atmosphere and community amenities, including a sparkling, resort-style pool—ideal for relaxing weekends. The heart of the home is the

  Daniela de Rodriguez B LIVE COMMERCIAL AND RESIDENT

  7241 Sunny Meadow Aly, 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

  Current Estimated Value $827,833

  Last Listing Agent Clementine Costantini KELLER WILLIAMS REALTY AT THE LAKES

  4509 Indian Deer Rd, Windermere, FL 34786
• 

  

  

  /97

  Est $2,435,497 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 5,500 Sq Ft

  Unlisted Address

  Unlisted Address
• 

  

  

  /42

  $799,900

  • 5 Beds
  • 3.5 Baths
  • 3,390 Sq Ft

  6615 Helmsley Cir, Windermere, FL 34786

  Beautifully remodeled and impeccably maintained, this spacious 3,390 sq. ft. two-story home offers 5 bedrooms, 3.5 bathrooms, an office, and an attached 2-car garage in the highly desirable community of Preston Square in Windermere. Perfectly situated on a premium lot with no rear neighbors, the home features a charming front porch and covered balcony overlooking the serene, tree-lined

  Angela Gann KELLER WILLIAMS ELITE PARTNERS III REALTY

  6615 Helmsley Cir, Windermere, FL 34786
• 

  

  /24

  $2,475 per month

  • 3 Beds
  • 2.5 Baths
  • 1,545 Sq Ft
  • Townhouse for Rent

  12910 Calderdale Ave, Windermere, FL 34786

  Townhome located in Wickham Park a desirable Windermere Community. Freshly painted and brand new carpet in all bedrooms and pergo laminate flooring in the living/dining area. End unit with Three Bedrooms, Two and one half baths. Kitchen has 42" wood cabinets, all Appliances, Granite Counter Tops and opens to the Living/Dinning area. All bedrooms are on the second floor, Master suite has a walk in

  Jane Sims SIMS REALTY LLC

  12910 Calderdale Ave, 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 RESIDENT

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

  

  /36

  Est $345,494 Not Listed For Sale

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

  14335 Oasis Cove Blvd Unit 2004, Windermere, FL 34786

  14335 Oasis Cove Blvd Unit 2004, Windermere, FL 34786
• 

  

  /30

  $3,200,000

  • 5 Beds
  • 5 Baths
  • 4,500 Sq Ft

  13161 Lake Butler Blvd, Windermere, FL 34786

  Extraordinary lake front opportunity in Windermere on 1.75 acres! PRIVATE GATES! NO HOA! SPECTACULAR LAKE VIEWS, PRIVACY, SPORTS COURT, AND GAZEBO ON LAKE ROPER - A WATER SKI FRIENDLY LAKE! A grand entryway leads you to magnificent two story ceilings and welcomes you into a separate living and family room. Beautiful 5-bedroom, 3/2-bathroom Mediterranean-style home with inlaid marble medallion

  Karolina Taylor EPIQUE REALTY, INC.

  13161 Lake Butler Blvd, Windermere, FL 34786
• 

  

  /61

  $4,500 per month

  • 6 Beds
  • 3.5 Baths
  • 3,764 Sq Ft
  • House for Rent

  14415 Crest Palm Ave, Windermere, FL 34786

  Be the First to Call This Home Yours! Brand New Luxurious 2025! Move-In Ready! Pet Friendly! 2-Car Garage! Smart Home! Stunning 6 Bedrooms, Loft, Bonus Room, Stylish Upgrades! Internet & WiFi Included! Step into luxurious, modern living in this expansive 6-bedroom, 3.5-bath, two-story smart home featuring a bright, open-concept layout that seamlessly connects the gourmet kitchen, family room, and

  Katrina Anarumo RENT A FLORIDA HOME

  14415 Crest Palm Ave, 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 $569,871

  Last Listing Agent Daniel Waldron MAINFRAME REAL ESTATE

  5140 Honeynut Ln, Windermere, FL 34786
• 

  

  /37

  Est $539,851 Not Listed For Sale

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

  11607 Black Rail St, Windermere, FL 34786

  11607 Black Rail St, Windermere, FL 34786
• 

  

  /52

  $900,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 3,102 Sq Ft

  9792 Wild Oak Dr, Windermere, FL 34786

  Seller says SELL! Listed $20,000 BELOW APPRAISED value!!! Discover this exquisite 3-bedroom, 3.5-bathroom pool home nestled on a lush 1/3-acre lot in the prestigious Windermere Downs community. Spanning 3,100 square feet, this property combines sophisticated design, functionality, and beautiful indoor-outdoor living spaces. Upon entry, you’re greeted by luxury vinyl flooring that flows through a

  Suzette Berkhalter KELLER WILLIAMS ADVANTAGE III

  9792 Wild Oak Dr, Windermere, FL 34786
• 

  

  /17

  $2,000 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

  $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 $340,237

  Last Listing Agent Vicente Virgilio ALTIS REALTY

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

  

  /41

  Est $325,985 Not Listed For Sale

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

  Unlisted Address

  Unlisted Address
• 

  

  /16

  $759,500

  • 4 Beds
  • 3.5 Baths
  • 2,820 Sq Ft

  6832 Thornhill Cir, Windermere, FL 34786

  4 bed, 3.5 bath, 2,827 SF home in desirable Windermere Florida, minutes from Disney - see the fireworks from home !!! Oversized corner lot (8,850 sq ft) in cul-de-sac, 22’ ceiling in family room with high tinted windows giving lots of natural light, Kitchen with plenty of counter space as well as a walk in pantry and 41” cabinets, 39x39 center island with cabinets, 100” bar/counter, Butler’s

  Jonathan Minerick HOMECOIN.COM

  6832 Thornhill Cir, Windermere, FL 34786
• 

  

  /7

  $1,275 per month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • House for Rent

  2156 Merrybells Dr, Kissimmee, FL 34746

  Welcome to this beautifully appointed mother-in-law suite featuring a spacious bedroom with ample natural light, a full bathroom, and a separate living area ideal for relaxing or entertaining. The suite also includes a kitchenette with modern cabinetry, a dedicated entrance for added privacy, and direct access to the main home when desired. Thoughtfully designed with neutral finishes and tile

  Mayling Marrero KELLER WILLIAMS ADVANTAGE III

  2156 Merrybells Dr, Kissimmee, FL 34746
• 

  /2

  $370,000 Sold Feb 03, 2026

  5235 Keenes Pheasant Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,462 Sq Ft
  • Built 2004

  Last Sold Summary

  • 14% Below List Price
  • $253/SF
  • 186 Days On Market

  Last Listing Agent Ronda Shively COMPASS FLORIDA LLC

  5235 Keenes Pheasant Dr, Windermere, FL 34786
• 

  /2

  Est $9,530,625 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
• 

  

  /34

  $860,000

  • 6 Beds
  • 4 Baths
  • 3,667 Sq Ft

  12676 Salomon Cove Dr, Windermere, FL 34786

  Discover luxury, space, and style in this beautiful 6-bedroom, 4-bath home nestled in the heart of Windermere’s highly desirable Westside Village! Built in 2018, this modern residence offers nearly 3,700 sq. ft. of elegant living space designed for both comfort and entertainment. Step inside to an open-concept floor plan with high ceilings, abundant natural light, and a seamless flow between the

  Anna Shi LPT REALTY, LLC

  12676 Salomon Cove 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

  $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 $417,901

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

  11746 Water Run Aly, Windermere, FL 34786
• 

  /2

  Est $328,168 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
• 

  

  /47

  $950,000

  • 5 Beds
  • 3.5 Baths
  • 3,717 Sq Ft

  12941 Westside Village Loop, Windermere, FL 34786

  Experience the elegance of Westside Village in Windermere, where timeless design meets modern luxury. This five-bedroom, four-bath residence spans 3,717 square feet of thoughtfully designed living space, built in 2018. The foyer welcomes you with porcelain tile floors, vaulted ceilings, and chandelier lighting that set a tone of quiet sophistication. French doors open to a versatile home office,

  Keren Reyes CENTURY 21 CARIOTI

  12941 Westside Village Loop, Windermere, FL 34786
• 

  

  /28

  $2,100 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

  $405,000 Sold Dec 22, 2025

  12838 Strode Ln, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,748 Sq Ft
  • Built 2015

  Last Sold Summary

  • 6% Below List Price
  • $232/SF
  • 58 Days On Market

  Last Listing Agent Luis Leon Medina LA ROSA REALTY LLC

  12838 Strode Ln, Windermere, FL 34786
• 

  /2

  Est $831,103 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
• 

  

  /21

  $3,200,000 Pending

  • Land
  • 2.21 Acres
  • $1,447,964 per Acre

  9151 Tibet Pointe Cir, Windermere, FL 34786

  Under contract-accepting backup offers. Positioned on over two acres with an impressive 136 feet of pristine shoreline on the Butler Chain of Lakes, this exceptional homesite offers an increasingly rare chance to craft a custom lakefront estate in one of Windermere’s most exclusive gated communities. Set within a distinguished enclave of Keene’s Pointe—surrounded by multi-million-dollar

  Janet Allen PREMIER SOTHEBYS INT'L REALTY

  9151 Tibet Pointe Cir, 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

  $1,094,508 Sold Apr 22, 2025

  14256 Crest Palm Ave, Windermere, FL 34786

  • 5 Beds
  • 3.5 Baths
  • 3,764 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Below List Price
  • $291/SF
  • 128 Days On Market

  Current Estimated Value $1,101,959

  Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  14256 Crest Palm Ave, Windermere, FL 34786
• 

  

  /57

  Est $1,005,058 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
• 

  

  /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
• 

  

  /98

  $35,900 per month

  • 7 Beds
  • 10 Baths
  • 8,362 Sq Ft
  • House for Rent

  9343 Tibet Pointe Cir, Windermere, FL 34786

  Perfectly sited on pristine Lake Tibet in Keene's Pointe Country Club, this stunning lakefront Stonebridge custom home has been completely updated. The modern exterior color brightens the façade and creates a unique transitional style. The wrought iron and glass doors add a refined entry. Opening to the two-story formal areas featuring timeless elements of stone flooring, elegant ceiling details,

  Juan Delgado LA ROSA REALTY LLC

  9343 Tibet Pointe Cir, Windermere, FL 34786
• 

  /2

  $390,000 Sold Aug 25, 2025

  12884 Calderdale Ave, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,565 Sq Ft
  • Built 2010

  Last Sold Summary

  • 2% Below List Price
  • $249/SF
  • 26 Days On Market

  Current Estimated Value $388,270

  Last Listing Agent Shirley Botansky RE/MAX PRIME PROPERTIES

  12884 Calderdale Ave, Windermere, FL 34786
• 

  

  /52

  Est $1,178,701 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
• 

  

  /44

  $384,900

  • 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
• 

  

  /80

  $3,100 per month

  • 4 Beds
  • 3.5 Baths
  • 2,600 Sq Ft
  • House for Rent

  13426 Chariho Ln, Windermere, FL 34786

  Welcome to this beautifully maintained 4-bedroom, 3-bath home with a loft and office located in a highly sought-after gated community in Windermere. This spacious residence offers a fresh, move-in-ready feel with fairly new carpeting throughout the stairs and second floor. The thoughtfully designed floor plan features a first-floor master suite, providing privacy and convenience, along with a

  Courtney James LA ROSA REALTY ORLANDO LLC

  13426 Chariho Ln, Windermere, FL 34786
• 

  /2

  $1,085,000 Sold Dec 03, 2025

  14389 Crest Palm Ave, Windermere, FL 34786

  • 6 Beds
  • 4.5 Baths
  • 4,443 Sq Ft
  • Built 2024

  Last Sold Summary

  • 10% Below List Price
  • $244/SF
  • 10 Days On Market

  Last Listing Agent Cindy Sapp OLYMPUS EXECUTIVE REALTY INC

  14389 Crest Palm Ave, Windermere, FL 34786
• 

  /2

  Est $397,806 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

Showing Results 321 - 360, Page 9 of 18