Windermere, FL Homes

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  $1,074,990 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
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  $2,650 per month

  • 2 Beds
  • 2.5 Baths
  • 1,239 Sq Ft
  • Townhouse for Rent

  12623 Langstaff Dr, Windermere, FL 34786

  ONE OF A KIND, EXECUTIVE WINDERMERE 2 BEDROOM 2.5 BATHROOMS TOWNHOME FURNISHED & DECORATED! This recently renovated home is in the sought-after Lake Reams Community only a minute drive to the backside of Disney! As you open the front door you are drawn to Upscale Interior, filled with Upgrades & a Warm Family Décor. The eating area overlooks an Enclosed Custom-Made Courtyard leading to a Detached

  Ernesto Cisneros ELITE REALTY ENTERPRISES LLC

  12623 Langstaff Dr, 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 $483,660

  Last Listing Agent Elle Walters JASON MITCHELL REAL ESTATE FLO

  5130 Sun Palm Dr, Windermere, FL 34786
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  /26

  Est $325,828 Not Listed For Sale

  11434 Jasper Kay Terrace Unit 208, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft
  • Built 2007

  11434 Jasper Kay Terrace Unit 208, Windermere, FL 34786

  Last Sold Summary

  • 11% Below List Price
  • $253/SF
  • 11 Days On Market

  Last Sold Price $365,000

  Last Listing Agent Jay Stewart SOUTHERN REALTY GROUP LLC
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  $3,200,000

  • Land
  • 6.76 Acres
  • $473,373 per Acre

  934 Roberson Rd, Ocoee, FL 34761

  PROPERTY DESCRIPTION - We are pleased to present a premier investment opportunity at 934 Roberson Road in Ocoee, just west of Orlando. This 6.76-acre parcel of vacant land comes with full site plan approval from the City of Ocoee for a 120-bed assisted living facility, making it an exceptional prospect for those looking to capitalize on the burgeoning demand for senior care services in Central

  Chase Collier Eshenbaugh Land Company

  934 Roberson Rd, Ocoee, FL 34761
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  $5,500 per month

  • 4 Beds
  • 4.5 Baths
  • 3,512 Sq Ft
  • House for Rent

  11560 Claymont Cir, Windermere, FL 34786

  Welcome to this spacious, fully furnished, 4-bedroom, 4.5-bathroom home nestled within a desirable gated golf community of Keene's Pointe. Thoughtfully designed for comfort and functionality, this impressive residence features a first-floor primary suite offering privacy and convenience, complete with a well-appointed ensuite bath. The home boasts generous living areas filled with natural light,

  Rose Sepulveda-Morales WATSON REALTY CORP.

  11560 Claymont Cir, Windermere, FL 34786
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  $1,220,000 Sold Jan 23, 2026

  2828 Ingeborg Ct, Windermere, FL 34786

  • 5 Beds
  • 4.5 Baths
  • 3,190 Sq Ft
  • Built 1990

  Last Sold Summary

  • 8% Below List Price
  • $382/SF
  • 40 Days On Market

  Current Estimated Value $1,172,535

  Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

  2828 Ingeborg Ct, Windermere, FL 34786
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  /53

  Est $1,061,050 Not Listed For Sale

  11708 Hampstead St, Windermere, FL 34786

  • 5 Beds
  • 4 Baths
  • 3,934 Sq Ft
  • Built 2015

  11708 Hampstead St, Windermere, FL 34786

  Last Sold Summary

  • 6% Above List Price
  • $254/SF
  • 22 Days On Market

  Last Sold Price $997,500

  Last Listing Agent Alex Vastardis COLDWELL BANKER REALTY
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  /18

  $425,000

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

  11636 Water Run Aly, Windermere, FL 34786

  This property is a beautifully maintained 3-bedroom, 2.5-bath townhouse located in the desirable Ashlin Park community of Windermere. Built in 2017, this home features an open-concept layout filled with natural light, a modern kitchen with quartz countertops, stainless steel appliances, and espresso cabinetry. The spacious primary suite offers a walk-in closet and an elegant ensuite bath. Enjoy a

  Jose Jimenez EXP REALTY LLC

  11636 Water Run Aly, Windermere, FL 34786
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  /25

  $2,800 per month

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

  7609 Sutherton Ln, Windermere, FL 34786

  Fully Renovated Corner Unit Townhome for Rent in Wickham Park – Windermere Beautiful 3-bedroom, 2.5-bath corner unit townhome, offering extra privacy, more natural light, and an enhanced sense of space, located in the desirable Wickham Park community in Windermere. This home features granite countertops, solid wood cabinets, stainless steel appliances news and a spacious open-concept living and

  Vivian Azuaje 1 ELEVEN REALTY

  7609 Sutherton Ln, 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 $490,749

  Last Listing Agent Erin Legler CHARLES RUTENBERG REALTY ORLANDO

  12285 Joshua Tree Trail, Windermere, FL 34786
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  Est $1,170,495 Not Listed For Sale

  5819 Caymus Loop Unit 1, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,806 Sq Ft
  • Built 2003

  5819 Caymus Loop Unit 1, Windermere, FL 34786

  Last Sold Summary

  • 2% Below List Price
  • $428/SF

  Last Sold Price $1,200,000

  Last Listing Agent Stellar Non-Member Agent FL_MFRMLS
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  $1,200,000

  • 4 Beds
  • 4 Baths
  • 2,787 Sq Ft

  1361 Whitney Isles Dr, Windermere, FL 34786

  Stunning residence with a private fenced backyard, located in the highly sought-after gated community of Belmere in Windermere, just minutes from the town center. Featuring 4 bedrooms, 4 bathrooms, and approximately 2,800 sq. ft. of air-conditioned living space, this home immediately captivates with its elegant Mediterranean architecture and lush tropical landscaping. Fully renovated this year,

  Gabriel Mantovani ALVES AND HOWELL REALTY

  1361 Whitney Isles Dr, Windermere, FL 34786
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  $9,850 per month

  • 4 Beds
  • 4.5 Baths
  • 4,239 Sq Ft
  • House for Rent

  1115 Estancia Woods Loop, Windermere, FL 34786

  Rare Newer Construction (2017) Windermere Pool Home located in close proximity to Downtown Windermere. This is a 2 Story home with tiled roof and so many upgrades and amenities. Beautiful Open floorplan with all of the upgrades. Through the large Sliding Glass doors, you flow into a fully covered Lanai and into the stunning brick paved pool area w/ Jacuzzi and the Scenic Landscaped Lot. This is

  Corey Cannon BHHS FLORIDA REALTY

  1115 Estancia Woods Loop, Windermere, FL 34786
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  $539,900 Sold Nov 20, 2025

  11091 Bagley Aly, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,222 Sq Ft
  • Built 2018

  Last Sold Summary

  • 2% Below List Price
  • $243/SF
  • 123 Days On Market

  Current Estimated Value $533,733

  Last Listing Agent Mariana Cezar Ovalle WRA BUSINESS & REAL ESTATE

  11091 Bagley Aly, Windermere, FL 34786
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  Est $452,899 Not Listed For Sale

  13701 Beckman Dr, Windermere, FL 34786

  • 3 Beds
  • 3 Baths
  • 2,091 Sq Ft
  • Built 2015

  13701 Beckman Dr, Windermere, FL 34786

  Last Sold Summary

  • 2% Below List Price
  • $222/SF

  Last Sold Price $464,000

  Last Listing Agent Lukasz Sokolowski, PA HOST MANAGEMENT GROUP LLC
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  $1,274,000 Pending

  • 5 Beds
  • 3.5 Baths
  • 3,689 Sq Ft

  12779 Westside Village Loop, Windermere, FL 34786

  Under contract-accepting backup offers. This exceptional residence offers a rare combination of contemporary design, smart technology, functionality, and lifestyle. Fully renovated and thoughtfully planned with meticulous attention to detail, the home showcases a high level of craftsmanship and a cohesive modern aesthetic throughout. Luxury vinyl flooring extends throughout the entire home,

  Ramon Brandão WEBB FLORIDA REALTY LLC

  12779 Westside Village Loop, Windermere, FL 34786
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  /22

  $2,300 per month

  • 2 Beds
  • 2 Baths
  • 1,161 Sq Ft
  • Apartment for Rent

  11565 Mizzon Dr Unit 209, Windermere, FL 34786

  Welcome to Lakeside at Windermere! Excellent gated condominium, each building has a elevator. This furniture unit is ready to move in, 2 bedroom and 2 bathroom on a second floor. Excellent location and amenities. Apartment will be available for start contract on March 1st 2026.

  Rosa Rodriguez Diaz ZARIA REALTY GROUP LLC

  11565 Mizzon Dr Unit 209, Windermere, FL 34786
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  $560,000 Sold Aug 13, 2025

  6539 Chagford Ln, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,265 Sq Ft
  • Built 2007

  Last Sold Summary

  • 2% Below List Price
  • $247/SF
  • 19 Days On Market

  Current Estimated Value $554,933

  Last Listing Agent Lori Lucente-Nelson RE/MAX PRIME PROPERTIES

  6539 Chagford Ln, Windermere, FL 34786
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  Est $2,528,862 Not Listed For Sale

  12624 Park Ave, Windermere, FL 34786

  12624 Park Ave, Windermere, FL 34786

  Last Sold Summary

  • 1% Above List Price
  • 215 Days On Market

  Last Sold Price $2,500,000

  Last Listing Agent Michael Julian JULIAN PROPERTIES, INC.
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  $1,590,000

  • 4 Beds
  • 4.5 Baths
  • 3,288 Sq Ft

  1703 Roberts Landing Rd, Windermere, FL 34786

  This elegant and fully renovated lakefront home on Lake Olivia in Windermere offers the ultimate blend of luxury, comfort, and Florida lifestyle. Featuring three master suites plus a guest bedroom and bathroom, the spacious layout is designed for both entertaining and everyday living. Large windows fill the home with natural light and frame breathtaking views of the water, while recent

  Wui Keong Goh INTERNATIONAL NETWORK REALTY

  1703 Roberts Landing Rd, Windermere, FL 34786
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  $2,850 per month

  • 3 Beds
  • 2.5 Baths
  • 1,742 Sq Ft
  • House for Rent

  7612 Fairgrove Ave, Windermere, FL 34786

  Beautiful two-story townhome in the desirable Windermere Sound community! This stunning residence offers 3 bedrooms, 2.5 bathrooms, and a spacious 2-car garage, spanning 1,742 sq. ft. of elegant living space. The home features stainless steel appliances, granite countertops, and modern finishes throughout. Windermere Sound provides residents with resort-style amenities, including a swimming pool,

  Maribel Minarro FLORIDA FANTASY REAL ESTATE INC

  7612 Fairgrove Ave, Windermere, FL 34786
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  $590,000 Sold Aug 06, 2025

  5263 Beach River Rd, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,432 Sq Ft
  • Built 2004

  Last Sold Summary

  • 1% Below List Price
  • $243/SF
  • 26 Days On Market

  Current Estimated Value $583,186

  Last Listing Agent Ariel Vargas EXP REALTY LLC

  5263 Beach River Rd, Windermere, FL 34786
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  Est $423,751 Not Listed For Sale

  8668 Wellington Blue Ln, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,722 Sq Ft
  • Built 2016

  8668 Wellington Blue Ln, Windermere, FL 34786

  Last Sold Summary

  • 3% Below List Price
  • $253/SF
  • 3 Days On Market

  Last Sold Price $435,000

  Last Listing Agent Vlad Kizlo KELLER WILLIAMS REALTY AT THE LAKES
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  $1,299,000 Pending

  • 5 Beds
  • 4 Baths
  • 3,557 Sq Ft

  11021 Hawkshead Ct Unit 2, Windermere, FL 34786

  Under contract-accepting backup offers. Welcome to this exquisite 5-bedroom, 4-bathroom residence nestled on a premium corner lot in one of Windermere’s most beautiful, gated communities. Boasting 3,557 square feet of thoughtfully designed living space, this Spanish Colonial-style home blends timeless elegance with modern comfort. Step inside to discover spacious living areas, rich architectural

  Kara Manuchia ALL REAL ESTATE & INVESTMENTS

  11021 Hawkshead Ct Unit 2, Windermere, FL 34786
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  $3,049 per month

  • 4 Beds
  • 2.5 Baths
  • 2,214 Sq Ft
  • House for Rent

  11507 Charnock Dr, Windermere, FL 34786

  Brand New Windermere 4 Bedroom Home For RentPriced Low, Call Now!, 2 Car Garage, BRAND NEW HOME, Upstairs Bonus Area Too!, Corner Lot, Granite Countertops, 42” Cabinets, Tile Flooring, Carpeted Bedrooms, COMMUNITY Pool, COMMUNITY Clubhouse, COMMUNITY Playground, JUST 30 MINUTES To: Downtown Orlando, CONVENIENT To: 429, JUST MINUTES To: Walt Disney World, CONVENIENT To: Major Roads, Shopping,

  Jay Myers ORLANDO REALTY & PROPERTY MGNT

  11507 Charnock Dr, Windermere, FL 34786
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  $975,000 Sold Oct 20, 2025

  635 Butler St, Windermere, FL 34786

  • 3 Beds
  • 3 Baths
  • 2,353 Sq Ft
  • Built 1924

  Last Sold Summary

  • 2% Below List Price
  • $414/SF
  • 0 Days On Market

  Current Estimated Value $966,978

  Last Listing Agent Scott Arthur KELLER WILLIAMS REALTY AT THE LAKES

  635 Butler St, Windermere, FL 34786
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  Est $1,143,582 Not Listed For Sale

  5522 Remsen Cay Ln, Windermere, FL 34786

  • 5 Beds
  • 4 Baths
  • 3,881 Sq Ft
  • Built 2016

  5522 Remsen Cay Ln, Windermere, FL 34786

  Last Sold Summary

  • 3% Below List Price
  • $303/SF
  • 5 Days On Market

  Last Sold Price $1,175,000

  Last Listing Agent Alfredo Karam COLDWELL BANKER REALTY
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  $1,548,900

  • 4 Beds
  • 4.5 Baths
  • 3,447 Sq Ft

  11821 Waterstone Loop Dr, Windermere, FL 34786

  WWaterstone is guard-gated, well-established, and home to something most neighborhoods can't match: a private pedestrian gate with direct access to Windermere Preparatory School, ranked the #1 private K–12 in Orange County. For families, that detail alone tends to end the search.The home itself is a custom Silliman Homes courtyard design, single-story, built with the kind of attention to

  Mauricio Penha VOLKE REAL ESTATE LLC

  11821 Waterstone Loop Dr, Windermere, FL 34786
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  $2,600 per month

  • 3 Beds
  • 2.5 Baths
  • 1,547 Sq Ft
  • Townhouse for Rent

  13285 Gorgona Isle Dr, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Available now! Beautiful 3 bedroom, 2.5 bathroom townhome for rent in the desirable Windermere area. Built in 2020, this home offers 1,547 sq ft of modern living space with an open concept layout, stainless steel appliances, granite countertops, and a two car garage. Pets allowed. Conveniently located near major roads, shopping, and dining. Monthly

  Rodrigo Andrade REALTY HUB

  13285 Gorgona Isle Dr, Windermere, FL 34786
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  $635,000 Sold Sep 05, 2025

  13978 Darchance Rd, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 2,884 Sq Ft
  • Built 2007

  Last Sold Summary

  • 4% Below List Price
  • $220/SF
  • 43 Days On Market

  Current Estimated Value $631,285

  Last Listing Agent Sean Popat BUYER REBATES REALTY

  13978 Darchance Rd, Windermere, FL 34786
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  Est $2,623,030 Not Listed For Sale

  9831 Grosvenor Pointe Cir, Windermere, FL 34786

  • 5 Beds
  • 5.5 Baths
  • 5,320 Sq Ft
  • Built 2012

  9831 Grosvenor Pointe Cir, Windermere, FL 34786

  Last Sold Summary

  • 2% Above List Price
  • $485/SF
  • 62 Days On Market

  Last Sold Price $2,577,550

  Last Listing Agent Angela Durruthy KEENE'S POINTE REALTY
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  $1,170,000

  • 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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  $1,400 per month

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

  8347 Lookout Pointe Dr, Windermere, FL 34786

  Luxury 1 Bedroom / 1 Bathroom Condo for RentExperience elevated living in this private, studio-style condo located above the garage. Designed for comfort and style, this beautifully maintained residence features in-unit washer and dryer, central A/C and heating, and private driveway parking.Set within a highly desirable A-rated school zone, the home is just minutes from upscale shopping,

  Jackie Yuan JHY REALTY INVESTMENTS, LLC

  8347 Lookout Pointe Dr, Windermere, FL 34786
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  $710,000 Sold Feb 19, 2026

  415 E 6th Ave, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,784 Sq Ft
  • Built 1986

  Last Sold Summary

  • 1% Above List Price
  • $398/SF
  • 8 Days On Market

  Current Estimated Value $745,298

  Last Listing Agent Omar Sousan LPT REALTY, LLC

  415 E 6th Ave, Windermere, FL 34786
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  Est $4,430,376 Not Listed For Sale

  12300 Montalcino Cir, Windermere, FL 34786

  • 5 Beds
  • 6.5 Baths
  • 7,649 Sq Ft
  • Built 2023

  12300 Montalcino Cir, Windermere, FL 34786

  Last Sold Summary

  • 6% Below List Price
  • $618/SF
  • 73 Days On Market

  Last Sold Price $4,725,000

  Last Listing Agent David Alvarez Aserraf ROI AVE LLC
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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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  $16,000 per month

  • 5 Beds
  • 5.5 Baths
  • 5,507 Sq Ft
  • House for Rent

  4326 Isabella Cir, Windermere, FL 34786

  Welcome to Windermere! The designer-decorated Villa Milano model home presents the utmost in luxury at the exclusive and gated Casabella Community. This corner lot, spacious residence is full with high-end features throughout the home, including solar panels, custom built-ins in the family room, wet bar and private study. Stone and wood flooring, soaring windows with custom window treatments.

  Robert Arnold SAND DOLLAR REALTY GROUP INC

  4326 Isabella Cir, Windermere, FL 34786
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  $1,370,000 Sold Apr 15, 2025

  5518 Oxford Moor Blvd, Windermere, FL 34786

  • 4 Beds
  • 4.5 Baths
  • 5,260 Sq Ft
  • Built 2003

  Last Sold Summary

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

  Current Estimated Value $1,435,933

  Last Listing Agent Sean Flatley KELLER WILLIAMS REALTY AT THE PARKS

  5518 Oxford Moor Blvd, Windermere, FL 34786
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  Est $321,808 Not Listed For Sale

  8110 Enchantment Dr Unit 1704, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,371 Sq Ft
  • Built 2011

  8110 Enchantment Dr Unit 1704, Windermere, FL 34786

  Last Sold Summary

  • 11% Below List Price
  • $263/SF
  • 19 Days On Market

  Last Sold Price $360,000

  Last Listing Agent Homes Orlando MAGIC KEY REALTY

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