Displaying: For Rent
Location: Windermere
Property Type(s): Single Family
Price: $10,000+
Do Not Show Listings
Windermere - 5 properties found
9701 LAKE ISLEWORTH CT, WINDERMERE, FL 34786
$12,500104 Days on yellowkey MLS ID: O6385693
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3535 Built: 2000Community: IsleworthSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: Windermere Elem
High School: Olympia High
Tax Year:
Middle School: Chain of Lakes Middle
Remarks: Within the gates of Isleworth Golf and Country Club on a lovely cul-de-sac, you will discover this Golf Villa, boasting over 3,500 square feet of space. With 3 bedrooms plus an office, which could easily be used as a 4th bedroom, this charming villa has a spacious master suite with a garden view step-down shower, a notable kitchen with breakfast nook, formal dining room, and living room with a gas fireplace. Enjoy the outside grill area and large fenced-in yard. The home has an oversize 2 car garage with a golf cart entrance for those golf enthusiasts.
Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)
Listing Agent: Michelle Corbin (407-491-2690)
10577 DOWN LAKEVIEW CIR, WINDERMERE, FL 34786
$15,00065 Days on yellowkey MLS ID: O6396406
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 5273 Built: 1986Community: LakesSpa: YesSingle Family
Elementary School: Thornebrooke Elem
Middle School: Gotha Middle
Remarks: Lease or Lease Purchase available! Experience true lakefront living on the famed Butler Chain of Lakes in this exceptional custom home offering 137 feet of pristine shoreline on nearly one acre of high, dry land. Enjoy sweeping panoramic water views, refreshing lake breezes, and even nightly Disney fireworks. Arrive via a circular paved drive framed by mature oaks and enter through an impressive solid cedar door with artisan leaded glass. Inside, the great room features soaring 23’ cathedral ceilings and a dramatic Tennessee river rock fireplace. The showstopping formal dining room is wrapped in oversized picture windows that perfectly frame the lake. Designed for comfort and convenience, the majority of the living space including all bedrooms is on the main level. The chef’s kitchen is fully equipped with solid wood cabinetry, granite countertops, Sub-Zero refrigerator, Thermador gas cooktop with exhaust, Bosch double ovens, wet bar, walk-in pantry, and a bright breakfast area with incredible water views. The spacious primary suite is a private retreat with its own screened lanai and a spa-style bath featuring a shower, jetted tub, dual vanities, and three walk-in closets. Secondary bedrooms are generously sized with ample closet space and well-appointed baths, including a steam shower. Outdoor living is unmatched with mature landscaping and colorful gardens, plus a motorized screened lanai with a summer kitchen featuring a pizza oven, prep area, grill, refrigerator, and TV. Relax by the pool, heated spa, and gas firepit, all positioned to take advantage of the desirable southern exposure for comfortable outdoor enjoyment. Boaters will love the rare, partially enclosed grandfathered-in dock with boat lift and side jet-ski lift. Additional features include newer doors and windows, a tile roof, and a custom floor plan maximizing lake views throughout. The Lakes community also offers a boat ramp and tennis courts. Enjoy Windermere living on the Butler Chain without the traffic, just minutes to major roads, top schools, shopping, and dining. This rare, well-built lakefront home is ready to welcome you.
Listing is courtesy of: THE SIMON SIMAAN GROUP (407-558-1396)
Listing Agent: Simon Simaan (407-558-1396)
11051 CONISTON WAY, WINDERMERE, FL 34786
$13,00081 Days on yellowkey MLS ID: O6392514
REDUCED by $500 (3.7%) on 05/11/2026
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 5498 Built: 2005Community: Reserve At Lake Butler SoundSpa: YesSingle Family
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: This exquisite custom residence in the Reserve at Lake Butler Sound community offers unparalleled luxury and sophistication. Striking wrought-iron arched double entry doors open to a seamless, airy floor plan featuring elegant travertine flooring and captivating views of the pool and lanai area.Elegant wrought-iron chandeliers grace the welcoming foyer and generous dining space. This home is filled with premium upgrades, including elite appliances, dual gas fireplaces, and soaring ceilings throughout.The expansive chef’s kitchen seamlessly connects to the casual breakfast nook and family room, highlighted by a bespoke built-in entertainment center and towering 10-foot corner sliding glass doors that fully retract to reveal a spacious screened porch equipped with its own fireplace and fully appointed outdoor kitchen.The kitchen boasts a massive central island, premium Dacor and Sub-Zero appliances—including a six-burner gas cooktop, double ovens, and a wet bar featuring a wine refrigerator and warming drawer—plus an oversized walk-in pantry.On the main level, you'll find a versatile game room with a full bar, a dedicated office, three additional bedrooms, and an impressive primary suite. The primary retreat showcases hand-scraped hardwood floors, a generous en-suite bath with dual vanities, access to a private courtyard, and an expansive walk-in closet.Upstairs, discover an additional bedroom with a full bath, along with a dedicated theater room featuring seating for six, a large screen, and projector setup.Ample parking and storage are provided by the three-car garage, complete with attic access. The fully fenced backyard centers around a grand pool with spa and impressive water features.This exceptional property includes partial designer furnishings as depicted in the listing photos. Enjoy convenient proximity to premier shopping, restaurants, major highways, world-famous attractions, and excellent educational options—such as top-rated public schools and private institutions like Windermere Preparatory School.
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Juan Delgado (407-744-4469)
3999 ISABELLA CIR, WINDERMERE, FL 34786
$15,950354 Days on yellowkey MLS ID: O6320216
Bed: 6 Bath: 7.0 Gar: 3 Liv Area Sq Ft: 6881 Built: 2018Community: Casabella Ph 2Spa: NoSingle Family
Remarks: 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 acre lot, this remarkable home presents an unparalleled opportunity to experience the epitome of high-end living. As you step inside, you'll be greeted by an aura of sophistication that permeates every corner of this lavish residence. With 6 generously appointed bedrooms and 6 full bathrooms accompanied by 2 half baths, there is no shortage of space for both family and guests. The residence boasts a thoughtfully designed layout that effortlessly combines practicality with aesthetics. The heart of this home is its modern kitchen, complete with top-of-the-line appliances and an oversized kitchen island, perfect for culinary enthusiasts and those who love to entertain. Seamlessly flowing from the kitchen is a spacious living area adorned with luxurious finishes, creating an inviting atmosphere for relaxation and social gatherings. A standout feature of this home is the bonus room, offering versatile space for a home office, entertainment center, or a personal gym - the possibilities are endless. The 3-car garage provides ample storage for vehicles and more. Step outside to your own private oasis, where a meticulously landscaped backyard awaits. The summer kitchen offers an ideal setting for outdoor dining and entertaining, while the lush greenery and serene surroundings provide a sense of tranquility. The oversized pool takes center stage, beckoning you to indulge in a refreshing dip or bask in the sun-kissed luxury. This residence is being offered fully furnished, allowing you to move in seamlessly and immediately begin enjoying the luxurious lifestyle it provides. Every detail, from the grand entrance to the intricate finishes, has been carefully curated to create an atmosphere of luxury and sophistication. Don't miss your chance to live in this unparalleled piece of Windermere's real estate. Schedule a private showing today to experience the grandeur and elegance of 3999 Isabella Cir firsthand.
Listing is courtesy of: DELUCA REAL ESTATE SERVICES CORP (407-690-9941)
Listing Agent: Lucas Desouza (407-690-9941)
4326 ISABELLA CIR, WINDERMERE, FL 34786
$14,00062 Days on yellowkey MLS ID: O6397512
REDUCED by $1,500 (9.7%) on 04/24/2026
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 5507 Built: 2014Community: CasabellaSingle Family
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to your private luxury retreat in the exclusive gated community of Casabella in Windermere. This exceptional fully furnished estate offers over 5,400 square feet of thoughtfully designed living space, featuring 5 bedrooms, 5.5 bathrooms, and a 3-car garage—perfectly blending elegance, comfort, and functionality. From the moment you arrive, the circular driveway and lush, manicured landscaping set the tone for what awaits inside. Step through the doors to discover a light-filled interior with refined finishes, expansive living areas, and designer furnishings curated for both everyday living and effortless entertaining. The home flows seamlessly from indoors to out, where your private backyard oasis takes center stage. Enjoy a resort-style pool and spa overlooking a tranquil pond, surrounded by tropical palms and Florida-native landscaping. Whether you’re hosting under the stars, relaxing in the spa, or gathering around the fire pit by the water, this space was designed for unforgettable moments. The fully fenced backyard provides both privacy and beauty, creating a peaceful retreat that feels worlds away—yet is just minutes from everything. Located in the highly sought-after town of Windermere, you’ll enjoy a rare combination of privacy, prestige, and convenience, with close proximity to top-rated schools, upscale dining, shopping, and Central Florida’s premier attractions. For added ease, lawn care and pool maintenance are included, allowing you to focus on enjoying the lifestyle this home offers—without the upkeep. This is a rare opportunity to lease a turnkey luxury home in one of Central Florida’s most desirable communities. Schedule your private showing today and experience elevated living at its finest. Pet Policy --One Dog of 35lb or less (full grown size) - NO AGGRESSIVE BREEDS! Pet insurance is required as well as current vet records. A non-refundable pet fee and additional rent is required for an approve pet . Failure to report any animal intended for residency will invalidate your application and immediately terminate your lease if you are selected. YOU MUST TOUR THE PROPERTY PRIOR TO SUBMITTING AN APPLICATION. Application Process: You will be required to submit the following when you fill out your application: Driver's License/State ID, Income Verification, and pictures, if any, of your pet. This must be done when you apply in order to proceed with your application. APPLICATION FEES ARE NON-REFUNDABLE AND APPLY TO EVERYONE 18+ YEARS OR OLDER. We check: Credit (rental collections and utility collections are red flags) Rental history Employment Background (extent determined by HOA requirements) Gross income must meet or exceed 3 times the monthly rent to qualify for the property you are interested in. Example-Applicant must be able to prove $3000 gross income (verifiable) in order to qualify for home that rents for $1000 a month. What is provable income? A copy of your last pay stub or a letter from your employer will help in determining your income. Sometimes copies of your bank statement or your tax return, W2 forms or 1099 forms are necessary as well. Types of income include, Child Support, Spousal Support, SSI, Retirement and/or Disability, Wages, Parental Support and Student Financial Aid. ALL APPLICATIONS ARE SUBJECT TO OWNER APPROVAL!
Listing is courtesy of: RIGHTHOUSE REALTY LLC (407-216-8788)
Listing Agent: Tim Schmidt (407-216-8788)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.