Windermere, FL Homes

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  $924,990 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
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  $4,500 per month

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

  8764 Powder Ridge Trail, Windermere, FL 34786

  Beautiful and spacious 4-bedroom home plus a bonus room, perfectly situated in the heart of Windermere. This property offers an unbeatable location just one block away from an A-rated school making it an ideal choice for families seeking both convenience and top-quality education.Featuring three full bathrooms and one half bath, this home provides comfort and functionality for modern

  Gilson Rodrigues KARDOSH REALTY

  8764 Powder Ridge Trail, Windermere, FL 34786
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  /2

  $9,000,000 Sold Oct 06, 2025

  • 11,100 Sq Ft
  • $811/SF
  • 0 Days On Market

  • 6 Beds
  • 10 Baths
  • Built 2004

  9832 Laurel Valley Dr, Windermere, FL 34786

  It’s more than a home, it’s a story waiting to be lived. The light that spills across the kitchen feels like an invitation to linger a little longer. The staircase carries the rhythm of celebrations, and the open spaces invite moments that turn into memories. Long after the boxes are unpacked, you’ll realize it wasn’t just the marble, the quartz, or the soaring ceilings that made you fall in

  Dianna Desboyaux EXP REALTY LLC

  9832 Laurel Valley Dr, Windermere, FL 34786
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  /2

  Est $3,263,685 Not Listed For Sale

  • 6 Beds
  • 9 Baths
  • 7,129 Sq Ft

  4261 Isabella Cir, Windermere, FL 34786

  4261 Isabella Cir, Windermere, FL 34786
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  /10

  $964,990 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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  /57

  $4,500 per month

  • 4 Beds
  • 5 Baths
  • 2,450 Sq Ft
  • House for Rent

  11994 Mckinnon Rd, Windermere, FL 34786

  Welcome home to an elegant and spacious 4 bedroom, 3 full bathroom, 2 half bathroom home located in the highly sought-after town of Windermere, it offers the perfect blend of privacy, comfort, and opportunity all in one of Central Florida?s most desirable communities. Enjoy the outdoor patio and pool with ample space to unwind and entertain. Whether it's a quiet morning coffee or an

  Gloria Alvarez CENTURY 21 CARIOTI

  11994 Mckinnon Rd, Windermere, FL 34786
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  /2

  $740,000 Sold Oct 06, 2025

  • 2,449 Sq Ft
  • $302/SF
  • 4 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2020

  9164 Patrimonio Loop, Windermere, FL 34786

  Live just minutes from the magic of Disney World! This beautiful 4-bedroom, 3-bath home offers nightly views of Disney fireworks from your charming front porch and a resort-style lifestyle right in your own backyard. Sitting on an oversized .27-acre fenced lot, there’s plenty of room for pets to run freely or to add a playground or garden oasis. The backyard is beautifully landscaped with

  Betsy Breton-Garcia KELLER WILLIAMS WINTER PARK

  9164 Patrimonio Loop, Windermere, FL 34786
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  /38

  Est $510,593 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,709 Sq Ft

  7688 Brofield Ave, Windermere, FL 34786

  7688 Brofield Ave, Windermere, FL 34786
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  /11

  $869,990 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
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  /17

  $3,000 per month

  • 4 Beds
  • 2.5 Baths
  • 2,814 Sq Ft
  • House for Rent

  Unlisted Address

  This beautiful 4-bedroom, 2.5-bath home with a 2-car garage is located in the highly desirable Summerport community in Windermere. The property features a serene water view on a conservation lot, offering both privacy and natural beauty. The home is within walking distance to the community clubhouse and Keenes Crossing Elementary School, and just minutes from Windermere Preparatory School,

  Matthew Paul LPT REALTY, LLC

  Unlisted Address
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  /2

  $2,250,000 Sold Oct 06, 2025

  • 4,929 Sq Ft
  • $456/SF
  • 81 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2005

  6761 Valhalla Way, Windermere, FL 34786

  “New Price Improvement” Beautiful & unique Home in one of the most charming streets of Keene's pointe "Valhalla Way". Offering stunning views of the 17th hole of the Golden Bear Club golf course, designed by Jack Nicklaus. Great floor plan and breathtaking surroundings. Upon entering through its elegant wooden double doors, you are greeted by a welcoming foyer and formal dining room, followed by

  Oscar Rodriguez B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE

  6761 Valhalla Way, Windermere, FL 34786
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  /58

  Est $621,549 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,610 Sq Ft

  7610 Brofield Ave, Windermere, FL 34786

  7610 Brofield Ave, Windermere, FL 34786
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  /32

  $2,100,000

  • 5 Beds
  • 4.5 Baths
  • 4,716 Sq Ft

  2958 Marquesas Ct, Windermere, FL 34786

  This beautiful and elegant courtyard-style estate, complete with a private guest house/in-law suite, offers the ideal retreat for multi-generational living within one of the most exclusive gated communities in the Town of Windermere. Designed for comfort, refinement, and privacy, this home embodies Florida luxury living at its finest, where indoor grace meets outdoor serenity. The split floor

  Dianna Desboyaux EXP REALTY LLC

  2958 Marquesas Ct, Windermere, FL 34786
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  /16

  $2,600 per month

  • 4 Beds
  • 2.5 Baths
  • 2,067 Sq Ft
  • Townhouse for Rent

  8210 Mystic View Way Unit 2803, Windermere, FL 34786

  Move right in! This spacious home features brand-new laminate flooring, fresh interior paint, and water included in rent!Located in the highly desired gated community of Oasis Cove, just minutes from Disney World, and surrounded by top-rated schools, shopping, and restaurants — including Windermere High School.? Home Highlights:* Rare 4-bedroom layout with downstairs master suite*

  Lucia Wu GOLDEN SUN REALTY INC

  8210 Mystic View Way Unit 2803, Windermere, FL 34786
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  /2

  $680,000 Sold Oct 03, 2025

  • 2,610 Sq Ft
  • $261/SF
  • 8 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2010

  7628 Brofield Ave, Windermere, FL 34786

  For Sale – Make This Stunning Home Yours in Lake Sawyer SouthThis exquisite 4-bedroom, 3.5-bathroom home is located in the highly desirable Lake Sawyer South community and is ready for you to make it your own.The open-concept layout seamlessly connects the kitchen, dining, and living areas, creating a bright and spacious atmosphere perfect for family living and entertaining. The

  Mariana Rondon LPT REALTY, LLC

  7628 Brofield Ave, Windermere, FL 34786
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  /51

  Est $807,128 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,345 Sq Ft

  4240 Blue Major Dr, Windermere, FL 34786

  4240 Blue Major Dr, Windermere, FL 34786
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  /52

  $2,390,000

  • 5 Beds
  • 4 Baths
  • 4,287 Sq Ft

  6252 Blakeford Dr, Windermere, FL 34786

  Now it’s your turn to live on the 18th hole of the Golden Bear Club golf course in a fully updated custom home, located on one of the most desirable streets in Keene’s Pointe. This house with a timeless design inside and out, has five bedrooms (two down and three up), four full bathrooms, three car garage, and incredible outdoor living with renovated pool and brand new pool enclosure. Upstairs

  Shane Croft COLDWELL BANKER RESIDENTIAL RE

  6252 Blakeford Dr, Windermere, FL 34786
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  $4,950 per month

  • 6 Beds
  • 4 Baths
  • 4,344 Sq Ft
  • House for Rent

  8298 Lookout Pointe Dr, Windermere, FL 34786

  Stunning home in the beautiful Windermere Trails Community sitting on a Special Conservation View Lot, 500ft walking distance from the Clubhouse. This fully upgraded Magnificent 6 bedroom 4 Full Bathroom open floor concept plan has Builders Structural and Design upgrades, plus many aftermarket upgrades to make it a Dream Home.Other features includes large closets in all of six bedrooms, huge

  Jacob Hara TRANSCEND REALTY

  8298 Lookout Pointe Dr, Windermere, FL 34786
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  /2

  $1,300,000 Sold Oct 03, 2025

  • 3,049 Sq Ft
  • $426/SF
  • 76 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2013

  11754 Waterstone Loop Dr, Windermere, FL 34786

  Exceptional single-story Silliman-built home in the 24-hour guard-gated community of Waterstone, adjacent to Windermere Prep. Boasting 4 bedrooms, 3 bathrooms, and an open-concept floorplan with luxury details throughout, this residence is truly designed to impress. Glass sliders in the Great Room reveal a spectacular resort-style oasis beyond with infinity saltwater pool and spa with lighting,

  Rob Rahter STOCKWORTH REALTY GROUP

  11754 Waterstone Loop Dr, Windermere, FL 34786
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  /16

  Est $327,411 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,455 Sq Ft

  11564 Mizzon Dr Unit 904, Windermere, FL 34786

  11564 Mizzon Dr Unit 904, Windermere, FL 34786
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  /41

  $1,950,000

  • 5 Beds
  • 5.5 Baths
  • 4,044 Sq Ft

  13036 Lake Roper Ct, Windermere, FL 34786

  Prepare to be dazzled by this exquisitely remodeled waterfront estate in a gated Windermere community. On over a one-acre private lot, the home sits on the shores of the pristine 38-acre Lake Roper. Massive double doors greet you as you enter into impeccable craftsmanship and high-end finishes that sparkle amongst the lakefront backdrop. Soaring ceilings and natural light highlight the scale and

  Leslie Heimer PREMIER SOTHEBYS INT'L REALTY

  13036 Lake Roper Ct, Windermere, FL 34786
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  /26

  $6,500 per month

  • 4 Beds
  • 3 Baths
  • 2,398 Sq Ft
  • House for Rent

  8507 Bowden Way, Windermere, FL 34786

  One or more photo(s) has been virtually staged. This charming home is nestled on a quiet, tree-lined street inside the highly sought-after gated community of Keene’s Pointe.This single-story residence is equipped with full-home solar power, offering energy efficiency and reduced electric bills!Featuring a split floor plan with 4 spacious bedrooms and 3 full baths across 2,398 square feet,

  Jessica Dessire Cueva PA CHARLES RUTENBERG REALTY ORLANDO

  8507 Bowden Way, Windermere, FL 34786
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  /2

  $292,000 Sold Oct 03, 2025

  • 1,455 Sq Ft
  • $201/SF
  • 348 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2007

  11434 Jasper Kay Terrace Unit 306, Windermere, FL 34786

  Beautiful Lakeside at Lakes of Windermere condominium - Third floor corner unit with screened balcony. This unit features an open floor plan that combines kitchen, living room, and dining room. The kitchen feature 42 inch wood cabinets and a breakfast bar. Spacious primary bedroom. The A/C was replaced in October 2020. Tons of storage throughout the unit! The community features Clubhouse, Pool,

  Jay Stewart SOUTHERN REALTY GROUP LLC

  11434 Jasper Kay Terrace Unit 306, Windermere, FL 34786
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  /46

  Est $1,226,982 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,818 Sq Ft

  7219 Sangalla Dr, Windermere, FL 34786

  7219 Sangalla Dr, Windermere, FL 34786
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  /33

  $1,979,000

  • 4 Beds
  • 4 Baths
  • 4,156 Sq Ft

  6047 Blakeford Dr, Windermere, FL 34786

  Stunning Golf-Front Luxury in Keene’s Pointe! Welcome to 6047 Blakeford Drive—an impeccably remodeled 4-bedroom, 4-bath residence offering 4,156 sq. ft. of A/C living space and 6,230 sq. ft. under roof. Perfectly situated along the renowned Jack Nicklaus Signature Golf Course, this home blends timeless elegance with modern comfort in one of Windermere’s most sought-after communities. Step inside

  Jay Martin CORCORAN PREMIER REALTY

  6047 Blakeford Dr, Windermere, FL 34786
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  /20

  $18,000 per month

  • 7 Beds
  • 6 Baths
  • 4,834 Sq Ft
  • House for Rent

  4303 Isabella Cir, Windermere, FL 34786

  Best Value in Casabella — Fully Furnished & Move-In Ready!Step into effortless luxury in this beautifully furnished residence, where elegant design meets everyday comfort. Soaring windows fill the space with natural light, highlighting stylish interiors and thoughtfully curated furnishings throughout.The open-concept layout is perfect for both relaxing and entertaining, with a chef’s

  Elisa Mroz WRA BUSINESS & REAL ESTATE

  4303 Isabella Cir, Windermere, FL 34786
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  /2

  $1,070,000 Sold Sep 30, 2025

  • 3,924 Sq Ft
  • $273/SF
  • 2 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 2001

  9641 Crown Prince Ln, Windermere, FL 34786

  Spacious living for the discerning requirements of the active household with 5 bedrooms all in one floor, large bonus/entertainment room, 3 car garage with deep parking bays, consistent wood and travertine flooring, separate formal living and dining rooms, an expansive rear porch/pool area with covered spaces for seating plus summer kitchen, and a huge 1 acre lot--in Windermere with easy access

  Anderson Tiu REIKI REALTY LLC

  9641 Crown Prince Ln, Windermere, FL 34786
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  /43

  Est $2,863,570 Not Listed For Sale

  • 6 Beds
  • 6.5 Baths
  • 6,011 Sq Ft

  13100 Bellaria Cir, Windermere, FL 34786

  13100 Bellaria Cir, Windermere, FL 34786
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  /75

  $1,279,000

  • 4 Beds
  • 3 Baths
  • 2,523 Sq Ft

  11318 Fenimore Ct, Windermere, FL 34786

  Welcome to 11318 Fenimore Ct, where a beautiful home awaits. This fully upgraded residence boasts four spacious bedrooms and three luxurious bathrooms, nestled on an expansive cul-de-sac lot overlooking a serene pond in Keene’s Pointe. Experience the joy of luxury living within a 24-hour, man-gated community nestled in the renowned Windermere.Oversized cul-de-sac lot for relaxation and

  Simone Esteves FSM REALTY INVESTMENTS

  11318 Fenimore Ct, Windermere, FL 34786
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  /59

  $15,000 per month

  • 5 Beds
  • 5.5 Baths
  • 5,339 Sq Ft
  • House for Rent

  6844 Valhalla Way, Windermere, FL 34786

  Beautiful and fully furnished home in Keene's Pointe golf community. Guard gated community. A Tuscan style luxury home with a large covered back patio with fireplace and large pool overlooking the 14th green Bear Club. Master and extra suite on first floor and three more suites upstairs. This house has a very big loft, perfect for entertaining.

  Marilene Auge CHARLES RUTENBERG REALTY ORLANDO

  6844 Valhalla Way, Windermere, FL 34786
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  /2

  $655,000 Sold Sep 30, 2025

  • 2,184 Sq Ft
  • $300/SF
  • 3 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2002

  11457 Arborside Bend Way, Windermere, FL 34786

  Pond Views | Single-Story | Windermere Gated Community | Set on a cul-de-sac in the gated community of Glenmuir, this single-story home set on over 1/4 acre lot, offering pond views with no rear neighbors. The split floor plan includes 4 bedrooms, 3 baths, and 2,184 square feet. Features include formal living and dining rooms, vaulted ceilings, tile flooring, and an eat-in kitchen with 42"

  Jeffrey Funk EXP REALTY LLC

  11457 Arborside Bend Way, Windermere, FL 34786
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  /37

  Est $357,389 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,601 Sq Ft

  8259 Maritime Flag St Unit 1, Windermere, FL 34786

  8259 Maritime Flag St Unit 1, Windermere, FL 34786
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  /29

  $352,995

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

  11564 Mizzon Dr Unit 210/913, Windermere, FL 34786

  One or more photo(s) has been virtually staged. $3000 CREDIT OFFERED FOR BUYERS PREPAIDS AND CLOSING COSTS.Step into this beautifully maintained Second Corner unit -floor unit in the sought-after Lakeside at Lakes of Windermere community. Ideally located Directly across from the community pool and clubhouse. Offering 1,442 square feet, this 3-bedroom, 2-bathroom home is designed for

  Corey Cannon BHHS FLORIDA REALTY

  11564 Mizzon Dr Unit 210/913, Windermere, FL 34786
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  $5,000 per month

  • 5 Beds
  • 4.5 Baths
  • 3,312 Sq Ft
  • House for Rent

  13106 Orange Isle Dr, Windermere, FL 34786

  Explore the WINTERSET model from Ryan Homes of the Sanctuary at Lakes of Windermere, a corner unit, this 5- bedroom, 4.5 bathroom in Windermere combines the modern elegance, and a touch of magic with its a DISNEY Fireworks view, offering a lifestyle of unparalleled comfort. Upon entering, you are greeted by those who appreciate a dedicated workspace, the home includes a spacious office and a

  Gladys Bezerra FLORIDA CONNEXION PROPERTIES

  13106 Orange Isle Dr, Windermere, FL 34786
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  /2

  $750,000 Sold Sep 30, 2025

  • 2,701 Sq Ft
  • $278/SF
  • 7 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1988

  1906 Maple Leaf Dr, Windermere, FL 34786

  Welcome to your dream home in the sought-after lakefront community of Windermere Downs, nestled along the tranquil shores of Lake Down! This custom residence sits on a small cul-de-sac. Boasting 4 bedrooms and 3 full baths, this lovely home features a huge screened-in pool overlooking the water—your best summer weekend destination for relaxing or entertaining.Enjoy cozy evenings by the

  Michelle Richardson KELLER WILLIAMS CLASSIC

  1906 Maple Leaf Dr, Windermere, FL 34786
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  /43

  Est $682,685 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 2,924 Sq Ft

  Unlisted Address

  Unlisted Address
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  /27

  $1,300,000

  • 4 Beds
  • 3.5 Baths
  • 2,658 Sq Ft

  11325 Fenimore Ct, Windermere, FL 34786

  Come home to a golf enthusiast’s dream set along the 6th Hole of the renowned Jack Nicklaus Signature 18-Hole golf course, The Golden Bear Club (est. 1999). The community of Keene's Pointe features 24-hr guards at both entrances (Main Entrance off Chase Rd (Residents/Guests); Second Entrance off SR535 (Vendor/Resident/Guest). Built in 2002, the home spans 2,658 square feet and is

  Toni Marie Cafferty COMPASS FLORIDA LLC

  11325 Fenimore Ct, Windermere, FL 34786
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  $5,000 per month

  • 5 Beds
  • 4.5 Baths
  • 3,483 Sq Ft
  • House for Rent

  11905 Camden Park Dr, Windermere, FL 34786

  This rare opportunity for a lovely two-story rental home in Keene's Pointe is now available to show and move in ready today - October 1, 2025. Terrific floor plan boasts 4BR/4.5 Baths + office + bonus room and a 3 Car Garage. Primary Suite is located on the man floor with all other bedrooms on the second floor along with the bonus room. Enjoy the great privacy this location offers as well as a

  Angela Durruthy KEENE'S POINTE REALTY

  11905 Camden Park Dr, Windermere, FL 34786
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  /2

  $550,000 Sold Sep 30, 2025

  • 2,414 Sq Ft
  • $228/SF
  • 3 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2004

  5238 Beach River Rd, Windermere, FL 34786

  Located in the desirable community of Windermere, this beautifully maintained home offers a blend of comfort, style, and privacy. A new roof installed in 2022 provides peace of mind, while thoughtful updates enhance everyday living. The spacious primary suite features a huge walk-in closet, and an oversized upstairs suite with a full bath offers versatility for guests or a private retreat. The

  Liza Farzati SERHANT

  5238 Beach River Rd, Windermere, FL 34786
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  /2

  Est $1,168,980 Not Listed For Sale

  • 8 Beds
  • 5 Baths
  • 4,751 Sq Ft

  6228 Roseate Spoonbill Dr, Windermere, FL 34786

  6228 Roseate Spoonbill Dr, Windermere, FL 34786

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