Windermere, FL Houses for Rent with Community Pool

Welcome to this beautifully updated home in the highly desirable Enclave at Berkshire Park in Windermere. Situated on an oversized corner lot of approximately .25 acres, this spacious residence offers the perfect combination of comfort, functionality, and curb appeal. Recently refreshed with brand-new interior paint and new carpet throughout, the home also features a newer roof and a spacious

Evan Caulfield STOCKWORTH REALTY GROUP

Experience Lakefront Luxury Living - where every day feels like a vacation. Prepare to be captivated by this fully renovated three-bedroom, three-bath lakefront home on the highly sought-after Lake Butler. Part of the Butler Chain of Lakes, featuring 13 connected lakes. A true retreat that blends resort-style amenities with refined design. Nestled on pristine waterfront, this property offers

Steve Simpson 407 PROPERTIES

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

Lucas DeSouza DELUCA REAL ESTATE SERVICES CORP

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

Timothy Schmidt RIGHTHOUSE REALTY LLC

Beautiful 3-Bedroom Home in Windermere Sound – Prime Location with Top-Rated Schools. Owner spent more than 10K to upgrade and add a screened porch! Welcome to this gorgeous 3-bedroom single-family home located in the highly desirable Windermere Sound community, known for its top-rated schools and exceptional lifestyle. This home offers the perfect blend of comfort, convenience, and community

Amanda Yuan MULTI CHOICE REALTY LLC

Stunning Beautiful Upgraded home in the desirable Wickham Park community in heart of Windermere. NO carpet. Perfect location. Top rated schools. Rent includes hoa fee and lawncare. Well-maintained 4 bedroom & 2.5 bath & 1 loft/retreat upstairs & 2 car garage on front. Sizable back yard with extended pave. Open floor plan with lots of upgrades. Great natural light in the whole house. Master

Jacky Liu YORK MILLS REALTY LLC

Stunning upgraded house in Windermere Isle in Gas community, Fully Fenced, NO Carpet in the house. Rent includes full lawn services and spectrum cable and internet service, save a lot bill. Two downstairs bedrooms are perfect for a guest bedroom and a home office. Tankless water heater. Beautiful engineer wood flooring and Ceiling fan with remote control in all rooms. Popular Designer paint,

Li Xue AGENT GROUP REALTY

Located in the highly sought-after Summerport community in Windermere, this move-in ready home offers the perfect combination of location, comfort, and everyday convenience. Zoned for highly rated schools and just minutes from Horizon West, Disney, downtown Winter Garden, shopping, dining, and major roadways including SR-429 and the Florida Turnpike, the location is hard to beat. Inside, you’ll

Evan Caulfield STOCKWORTH REALTY GROUP

LOCATION, LOCATION, LOCATION. Beautiful 4/bed 2.5/bath home in desirable Windermere Trails. Watch Disney fireworks nightly fromspacious front porch! The home has tile and luxury vinyl throughout (NO CARPET) with plenty of room for families or individuals. Family room and dining room are downstairs along with a kitchen that features stainless steel appliances and granite counters. Master

Carolyn Hunt TOPSKY REALTY INC

Looking for Luxurious home in a prime location? Look no further! Located in the Isleworth Country Club, this stunning single-family home at 6131 Payne Stewart Drive is now available for rent. Situated in a fantastic waterfront location on Lake Chase, which is part of the Butler Chain of Lakes, this home is a short walk away from the world-renowned Isleworth Golf and Country Club. With breath

Jill Irwin IRWIN REALTY GROUP LLC

Beautiful house for rent in Windermere!! location, location and location. 3 bedrooms, 2 baths, 2 car garages. Beautiful large backyard and screen porch. Great school system. House is in highly desirable Lakes of Windermere! NO CARPETS!! The interior is FRESHLY Painted in alabaster tones, 3 Bedrooms, 2-baths, property is loaded with upgrades and has purposeful utility and functionality. Enter into

Maria Castro-Aversano LPT REALTY, LLC

One or more photo(s) has been virtually staged. Tucked within the gated enclave of Eden Isle in Windermere's Summerport, this beautiful canal-front, three-car garage and pool home has an ideal layout for multigenerational living. It offers an abundance of amenities with the canal leading directly to skiable Lake Speer and a rare combination of privacy, flexibility and outdoor living, and features

Courtney Bass PREMIER SOTHEBY'S INTL. REALTY

Spectacular Windermere home offering elegance, comfort, and a highly functional layout. Freshly painted with brand-new luxury vinyl flooring throughout, this 4-bedroom, 3.5-bathroom residence is located in the desirable Windermere Sound community. The home features bright, open living spaces with a seamless flow between the kitchen, dining, and living areas, ideal for daily living and

Fernanda Berretta AUTHENTIC REAL ESTATE TEAM

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

Juan Delgado LA ROSA REALTY LLC

Vacant! Great Location! Great House!! Must See!!! Move into this home inside the lovely Berkshire Park community in the very desirable town of Windermere. This house is full of upgrades and is an Energy Star certified home. Downstairs has tiled floors, and a private study room. It oversees the front porch. Kitchen has all appliances and granite countertop. It opens to the Great Room and provides

Daniel Zheng CINO INTERNATIONAL INC

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

Simon Simaan THE SIMON SIMAAN GROUP

POOL HOME!!! WITH MOTHER IN LAW SUIT!!! 5 BEDROOMS 4 FULL BATHS!!! MAN-GATED COMMUNITY IN WINDERMERE!!! Stunning Windermere home at 1351 Glenwick Dr! Spacious open floor plan, modern kitchen, and elegant finishes throughout. Perfect for entertaining or relaxing in the private backyard. Close to top schools, shopping, and dining. A must-see blend of luxury, comfort, and location!

Adriana Montes MBA FLORIDA DREAMS REALTY GRP INC

This stunning and well-maintained single-family home is located in the gated Belmere of Windermere community, just steps from top-tier amenities including the pool, tennis courts, and fitness center, as well as nearby elementary, middle, and high schools, Zoned for A-rated schools. The spacious two-story layout features 5 bedrooms, 3 full bathrooms plus a half bath, a 2-car garage, high ceilings,

Cristiane Carneiro Spfndola Rocha L WRA BUSINESS & REAL ESTATE

Available starting on AUGUST 1, 2026. LAWN CARE & POOL MAINTENANCE INCLUDED — Move in and enjoy from day one. Live the Florida luxury lifestyle without the hassle. Nestled behind the exclusive 24-hour guard-gated gates of The Reserve at Belmere — one of Windermere's most prestigious communities — this stunning Mediterranean-style estate offers over 4,000 square feet of refined living with every

Yana Ogor CHARLES RUTENBERG REALTY ORLANDO

GOLF FRONT!! Beautiful 4-Bed, 3-Bath Home for Rent in the Exclusive Keene’s Pointe Golf Community Nestled in the sought-after and secure gated community of Keene’s Pointe, this stunning single-story home offers a rare opportunity to live in a neighborhood renowned for its strong sense of community and premium amenities. Community Features: • Gated with 24/7 Manned Security: Peace of mind and

Hans Welbergen WINDERMERE INTERNATIONAL REALTY

Experience luxury living in this beautifully updated 4-bedroom, 2.5-bathroom single-story home located in the 24/7 gated camera surveillance Belmere community in Windermere. This home has been completely and tastefully remodeled with luxury finishes throughout, transforming it into a modern sanctuary of comfort and elegance. Every detail has been upgraded with intention, blending sophistication,

Margaret Marambio LPT REALTY, LLC

Welcome to this beautiful 3 bedroom, 2.5 bathroom home for rent in the highly desirable Windermere Trails community! This spacious two-story home features all bedrooms conveniently located upstairs along with a loft area, perfect for a second living space, office, or playroom. The upstairs laundry room includes a washer and dryer for added convenience. Enjoy a functional layout, a 2-car garage,

Vlad Kizlo KELLER WILLIAMS REALTY AT THE LAKES

Welcome to the famed Butler Chain of Lakes waterfront lifestyle! Experience luxury living with small town charm in this Town of Windermere residence boasting breathtaking water views with access to 12 connected lakes. Three of the four bedrooms offer lake views, two with sitting areas and one with access to the patio. You will enjoy the mesmerizing lake vistas from every angle. Step outside into

Rebekkah Boskovich REVEL REALTY LLC