Windermere Single Family Homes For Rent - 40 homes

Remarks: Beautiful 4-bedroom 2.5 bath home located in the desirable Lakes of Windermere community. This two-story corner lot home has everything you can ask for, formal living and dining rooms, kitchen with granite countertops, stainless steel appliances, and a breakfast bar that opens to a large family room, on the first floor you also have a massive master bedroom suite, with a large closet and the bathroom with double sinks, garden tub, and separate shower. On the second floor, you have 3 bedrooms and a shared bathroom. Afterwork you can relax on the front porch or on the screened back lanai. The community has lots of amenities pool, a tennis court, walking trails, and a dock. A-rated schools. Close to shopping, amusement parks, and an easy commute. +++++++ Evaluation criteria for prospective tenants: - No Evictions - No Sex Offenders - Credit score minimum 630 - Income to rent 3 times minimum - One small pet may be considered, nonaggressive breeds only. ***Some photos are virtually staged.

Listing is courtesy of: SHINING OAK REALTY (407-399-2298)

Listing Agent: Paul Moscoso (321-210-2456)

Remarks: Welcome home to this beautifully maintained property in Windermere’s sought-after Summerport community. Enjoy a chef-inspired kitchen complete with solid countertops, updated stainless steel appliances, and a gas range—perfect for everyday living and entertaining. New interior paint, stylish flooring throughout, and upgraded lighting and bathroom fixtures make this home the perfect rental! Conveniently zoned for Windermere High School

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: Alex Sadowski (407-405-1079)

Remarks: Live in one of the most sought after locations of Windermere! Welcome to 9313 Palm Tree Drive, located just minutes from Disney, Dr. Phillips, and Restaurant Row without the traffic and chaos. Located in the Silver Woods community off Apopka Vineland Rd, this 3 bedroom, 2 bath recently updated home is the perfect spot as your new home! Inside, you’ll find updated quartz countertops, newer appliances, wood look plank tile flooring throughout the bedrooms, and spacious closets in every room. Both bathrooms have been recently updated with new countertops and sinks for a clean, modern feel. Step outside to a fully fenced backyard with plenty of space to relax, entertain, or enjoy the outdoors! Rent includes Pest Control and Lawn Maintenance! Homes in this location don’t come up often for rent. If you’re looking for convenience, location, and a clean well kept home, this is it. Inquire today!

Listing is courtesy of: FHG REALTY, LLC (407-505-7600)

Listing Agent: Jeff Inman (407-505-7600)

Remarks: 3 Bed 2 Bath Pool home 1 block from Windermere Elementary School * Private Boat Ramp to Lake Butler & Chain of Lakes * Friendly Pets Welcome - Completely Resurfaced Pool & Spa * Rear Porch has been enclosed to create a nice Sunroom with A/C * Fenced Yard * Storage Building * Carport with Extra Storage Room * Washer & Dryer Included * Available May 1, 2026

Listing is courtesy of: VINTAGE REALTY GROUP LLC (407-217-5458)

Listing Agent: Darrell Nunnelley (407-467-8069)

Remarks: 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)

Remarks: This beautifully POND view and well maintained 4-bedroom, 2.5-bath Corner home in the desirable Lakes of Windermere community?Featuring a brand-NEW roof installed in 2025, this home offers both peace of mind and long-term value. Situated on a premium corner lot, the home enjoys serene pond views from the front porch—perfect for relaxing evenings, watching sunsets, and even Disney fireworks. Newer exterior paint and updated landscaping Inside, you’re welcomed by a bright, airy feel with Newer interior paint and light ceramic tile throughout the main living areas. 2025 luxury vinyl floor, NO carpet at whole house!! The open-concept kitchen features solid surface countertops, ample cabinetry, a breakfast bar, and a walk-in pantry, flowing seamlessly into the dinette and family room. The split floor plan provides privacy, with the owner’s suite tucked away at the rear of the home, while three additional bedrooms are located at the front. A screened rear porch and rear-entry 2-car garage add both functionality and charm. Additional upgrades include crown molding, garage storage shelving. Great school zone! Residents of Lakes of Windermere enjoy resort-style amenities including a community pool, playground, tennis courts, beach volleyball, open green spaces, and a fishing pier on Lake Sawyer. Conveniently located near shopping and dining at Winter Garden Village, just 2 miles from Windermere Preparatory School, 9.7 miles to Disney, and 26 miles to Orlando International Airport. Don’t miss this exceptional opportunity—schedule your private showing today.

Listing is courtesy of: RC GROUP REALTY LLC (407-492-6778)

Listing Agent: Erika Gao (407-808-6966)

Remarks: This 4BR/4 FULL Bath PLUS BONUS ROOM home located right next to a beautiful park in Keene’s Pointe is calling your name! Enjoy the serenity of this guard gated, golf course and country club community. This flexible split floor plan features all 4 bedrooms downstairs with the primary suite on one side of the house and on the other side you will find a deluxe, Jack and Jill bedroom layout with double vanities, and the 4th bedroom with full bath located at the rear of the house with a private entrance door that leads out to a large serene backyard. Upstairs you will find a generously sized bonus room with a privacy door and FULL bathroom across the hall. The bonus room could make a great 5th bedroom, home office, or playroom. This home has a very flexible floor plan and plus you can see Disney fireworks every night from your own front door! Located near to the recently enlarged County Road 535 entrance to Keene’s Pointe, it is convenient to all major highways, just minutes from Disney and a wide variety of shopping opportunities and essential service providers right nearby. As a resident, you have the option of joining the Golden Bear Country Club as either a golf or social member in order to use the fitness center, tennis courts, pool, restaurant, and golf facilities. Initiation Fee and monthly dues would be required.

Listing is courtesy of: B LIVE COMMERCIAL AND RESIDENT (407-217-7573)

Listing Agent: Oscar Rodriguez (321-297-7264)

Remarks: This stunning waterfront home with a pool in the desirable 24-guard gated neighborhood of Keene’s Pointe is available for immediate occupancy! Welcome home to your exquisite single-story remodeled home spanning 2,851 sq ft with an open-concept design, featuring wood floors with contemporary style throughout. Highlights include spacious bedrooms, a separate study, living room, dining room, and a family room with expansive pond views. Your fully equipped kitchen includes stainless appliances, wood cabinets, marble backsplash, quartz counters, and a farmhouse sink. The primary bedroom is spacious with a spa-like bathroom including dual floating vanities, soaking tub, glass shower, and a walk-in closet. Secondary bedrooms have an adjacent bathroom with a separate loft area perfect a game room or gym. Enjoy the beautiful Florida weather in your screened in pool with a summer kitchen, and covered lanai overlooking the pond. The home also includes plenty of storage space with a three-car garage. Additionally, Keene’s Pointe is a 24-hour guard gated community, including plenty of parks, playgrounds, with access to The Butler Chain of Lakes, The Golden Bear Country Club with amenities that include a gym, pool, golf, tennis courts, and neighborhood boat/RV storage. Close to Orlando’s best attractions including Walt Disney World, shopping, and “A” schools including Windermere Elementary, Bridgewater Middle, and the newer Windermere High School. Don’t miss out on this extraordinary rental property.

Listing is courtesy of: THE SIMON SIMAAN GROUP (407-558-1396)

Listing Agent: Simon Simaan (407-558-1396)

Remarks: One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Discover this newly updated 4 bed/2.5 bath single house located in the highly sought-after Windermere Trail community at Windermere. This cute house has a very spacious front porch for rocking chairs and morning coffee. Inside this airy and high-ceiling home, the newer luxury vinyl flooring on the stairs and the whole 2nd floor boasts upscale appearance and easy cleaning. Upon the entry a huge living room with flooding natural light through multiple windows welcomes family and friends. The living room opens to a gourmet kitchen with granite counter top, 42” maple cabinetry and stainless steel appliances. Next to the kitchen, a separate dining room with abundant light is perfect for gatherings formal or casual. Ascending the elegant and newer vinyl stairs you reach the 2nd floor bedrooms and the loft. The loft is perfect as a great room for TV, games or even study. The master bedroom is separated from other 3 bedrooms. The spacious master bedroom has an over-sized walking closet room with its own window. You will love the huge master bath with double vanity/sink, linen closet and glass door shower. On the other end of the hallway there are three bedrooms sharing another full bath with double vanity/sink. A laundry room conveniently sits next to the bedrooms with large capacity washer/dryer and plenty of room for racks and tables. This house has a two-car garage and two-zone irrigation system. The Windermere Trail club house is one block away from this home. A beautiful pool, two huge pavilions, and a playground are right next to the tranquil Lake Reams decorated with lush greenery and palm trees. A close-by Lakeside Village Park is little one's paradise with many slides, climbers and craw-through tubes. Located in Windermere, the upscale, finest and safest area of central Florida, zoned for top-rated schools, conveniently situated for quick access to supermarkets and additional shopping/dining, and with close proximity to great towns of Winter Garden, Horizon West and Dr Phillips, this gorgeous home won’t last long. Don’t wait, call today!

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Sherry Wang (484-744-4586)

Remarks: 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 living in one of Central Florida’s most sought-after areas. The home features a well-designed layout with a kitchen equipped with granite countertops, providing both style and functionality for everyday living and entertaining. The inviting living spaces create a warm and comfortable atmosphere throughout. Enjoy the added benefit of lawn maintenance included in the HOA, allowing for a low-maintenance lifestyle. Community Features & Amenities Residents of Windermere Sound enjoy access to a variety of well-maintained amenities, including: Resort-style community swimming pool Tennis courts Basketball court Playground / tot lot Walking paths and green spaces Beautifully landscaped surroundings and a welcoming neighborhood atmosphere Perfectly located near restaurants, grocery stores, movie theaters, and hospitals, this home also offers a unique bonus — the opportunity to enjoy Disney fireworks nightly from within the community. This property presents a wonderful opportunity to enjoy modern living, excellent schools, and outstanding community amenities in Windermere. Please call our office for showing now!

Listing is courtesy of: MULTI CHOICE REALTY LLC (352-404-6542)

Listing Agent: Amanda Yuan (407-353-2867)

Remarks: Located in a highly sought-after top-rated school zone, this beautifully designed two-story home offers the perfect blend of space, privacy, and functionality. Featuring four spacious bedrooms and 2.5 bathrooms, the home is thoughtfully laid out to accommodate modern living. The showpiece of the home is the oversized gourmet kitchen, complete with abundant cabinet and counter space and two large islands—ideal for casual dining, entertaining, and everyday meal prep. A generous walk-in pantry provides additional storage and organization. The open-concept design allows natural light to flow throughout the main living areas, creating a bright and inviting atmosphere. The first floor includes a convenient bedroom that can serve as a guest suite, office, or flex space. Upstairs, a large loft offers versatile space for a media room, play area, or secondary living space. The upstairs laundry room is enhanced with a utility sink for added practicality. Step outside to enjoy overlooking a private backyard with no rear neighbors, offering peaceful views and added privacy—perfect for relaxing or entertaining. With its functional layout, desirable school zoning, and rare privacy setting, this home presents an exceptional opportunity in today’s market.

Listing is courtesy of: INTEREALTY SERVICE (626-328-8535)

Listing Agent: Emma Yue (626-328-8535)

Remarks: 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 an Entertainer's Dream Home. Equipped with Outdoor speakers, Outdoor Grill, Exhaust, Refrigerator, Stove, pool Bath and Lanai. The Kitchen layout adds to this with a large Island to gather and entertain guest. The Wine Cooler addition is a plus. Additional Classy Spiral staircase adds additional access to the upstairs Loft style Family Areas. This home was built with an exceptionally large Master bedroom extension as well as an oversized laundry room. More than adequate closet space. Three Car Garage. The front offers a covered patio for sitting during the cool Florida evenings. Located in Close Proximity to all local Public and Private schools and Shopping and Restaurants, Publix etc. Pets are Negotiable and a multi-year lease is considered. Tenants will handle Lawn and Maintenance, or it can be added as a convenience. This estate style subdivision is like no other with beautiful grounds, Huge fully fenced back yard. High ceilings show off the cutting-edge architecture of the floorplan. This one should lease very quickly.

Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)

Listing Agent: Corey Cannon (407-615-0215)

Remarks: Beautiful home located in the highly desirable Vineyards community in Windermere, offering a perfect blend of comfort, convenience, and lifestyle. This well-maintained property features an open and bright floor plan, spacious living areas, and modern finishes throughout. The kitchen is designed for both functionality and entertaining, with ample cabinetry, quality countertops, and a welcoming dining space. The bedrooms are generously sized, including a primary suite with walk-in closet and a well-appointed bathroom. Residents of the Vineyards enjoy resort-style amenities, including a community pool, playground, scenic ponds, and walking areas, creating a family-friendly and relaxed environment. The community is known for its clean layout, open spaces, and modern development. Ideally located just minutes from top-rated schools, shopping, dining, and major highways, with easy access to Walt Disney World and Orlando attractions, making it a prime location for both homeowners and investors.

Listing is courtesy of: INTERNATIONAL REAL ESTATE LLC (407-760-5150)

Listing Agent: Delia Lugo (407-760-5150)

Remarks: **AVALAIBLE NOW ***Welcome home to this stunning and well maintained home in the highly sought after Lakes of Windermere. **4th room has closet and can be used as office or 4th bedroom.** House has totally been remodeled with 42" kitchen cabinets, granite countertops, stainless steel appliances, double vanity in master bath with soaking tub and separate shower, wood flooring in main areas, NEW carpet in the 2nd and 3rd bedroom. Fenced back yard, House is wired for cable, internet and home security. 220 volt charging station in 2 car Garage. Just 5 minutes to downtown Windermere, 10 minutes to Disney & 15 minutes to major shopping, hospitals and expressways. Lots of community amenities, such as swimming pool, playground, tennis/basketball courts, and community dock on big lake.

Listing is courtesy of: FRONTLINE FLORIDA REALTY, INC. (407-832-4888)

Listing Agent: Alan Martin (407-832-4888)

Remarks: 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 serene atmosphere, allowing for maximum productivity while working from home. The expansive living room boasts soaring ceilings, allowing natural light to cascade through the large windows, creating an airy and inviting ambiance. The gourmet kitchen is a chef's dream, featuring stainless steel appliances, a large cabinetry, and a spacious island with granite countertops. The adjacent formal dining room is perfect for hosting intimate gatherings or grand dinner parties. The master suite is offering a sanctuary of tranquility, a enormous shower, and dual vanities. Each of the remaining four bedrooms is generously sized, providing comfort and privacy for family and guests. The highlight of the outdoor space is the breathtaking view of the nightly Disney fireworks display, visible from the comfort of your own home. This feature creates a magical atmosphere and makes every evening a celebration.

Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)

Listing Agent: Victor De Oliveira (321-393-2772)

Remarks: Magnificent 4 bedroom 2.5 bathroom home! Move in ready with new lush carpet and fresh 2-tone paint. Beautiful tiled flooring leads you into the spacious kitchen with a long breakfast bar and a spacious island. The kitchen also showcases a custom backsplash, stainless steel appliances, large cabinets, and plenty of counter space. The open floor plan gives this home the perfect space for entertaining that you have been looking for. Enjoy the master suite with vaulted ceilings and 3 large windows letting in the natural light. The master bathroom has a spacious walk-in shower, his and her vanities with granite tops, and huge garden tub. There is so much to adore about this home, you do not want to miss out on this one. Come and see today!

Listing is courtesy of: CINO INTERNATIONAL INC (407-354-3318)

Listing Agent: Ya Lan Chien (321-960-1245)

Remarks: Ready for immediate occupancy. No HOA. Welcome to Sunrise on The Lake, an exceptional, fully remodeled one-story retreat in the heart of downtown Windermere with stunning views over Lake Bessie. Wake up to breathtaking sunrises and, on clear evenings, enjoy the rare treat of watching rocket launches from Cape Canaveral right your home. Inside, every detail feels elevated, solid wood floors, level 5 finished walls and ceilings, and a cozy gas fireplace create a refined, inviting atmosphere. The elegant dining room features a marble top credenza, perfect for hosting. The chef’s kitchen is fully equipped with leathered stone countertops, Samsung stainless steel appliances, a Bosch dishwasher, gas range, and a beautiful porcelain farmhouse sink. The Florida room opens to a private half-acre backyard oasis. The primary suite offers three closets, dual vanities, and a sleek glass shower. A secondary bedroom overlooks the lake and sits next to a full adjacent bath, ideal for guests or a home office with a view. Step outside and prepare to be impressed, an inground heated saltwater pool and spa with massaging jets, two gas fire bowls, water features, a louvered pergola for outdoor dining and entertaining, plus an outdoor shower. The property also includes a four-car garage for a workshop/storage/car collection, fenced backyard, whole-house generator, and newer major systems (including plumbing, AC, and ductwork). Just a short distance to the Windermere business district’s restaurants and shops. Enjoy easy access to the Lake Bessie and Lake Butler boat ramps, weekly farmers market, monthly food truck night, top-rated schools, and you’re only about 15 minutes from the major theme parks. Make this home yours and be sure to click the virtual tour links!

Listing is courtesy of: THE SIMON SIMAAN GROUP (407-558-1396)

Listing Agent: Simon Simaan (407-558-1396)

Remarks: Live in one of the most sought after locations of Windermere! Welcome to 9322 Palm Tree Drive, located just minutes from Disney, Dr. Phillips, and Restaurant Row without the traffic and chaos. Located in the Silver Woods community off Apopka Vineland Rd, this 3 bedroom, 2 bath pool home is the perfect spot as your new home. This home features an open layout with comfortable living spaces and a private pool. Rent includes pest control, pool maintenance, and lawn care, offering true low-maintenance living. Homes in this location don’t come up often for rent. If you’re looking for convenience, location, and a clean well kept home, this is it. Inquire today! INTERIOR PICS COMING SOON..

Listing is courtesy of: FHG REALTY, LLC (407-505-7600)

Listing Agent: Jeff Inman (407-505-7600)

Remarks: Recently Refreshed & Energy Efficient House in Windermere! This 3-bedroom, 2.5-bathroom home with a versatile bonus loft is move-in ready. The interior has been upgraded with brand-new carpet and fresh neutral paint throughout. Experience utility savings with a high-efficiency solar panel system and Energy Star certified insulation. The home features an open floor plan, an attached 2-car garage, and includes a washer and dryer for tenant convenience. Community Features: community pool, splash pad, dog park, playground, and scenic walking trails. Minutes from Lakeside Village Shopping Center and Publix. ---Application Fee $75.00 Per Adult (18 & Older) [Submit 1 application for each adult, complete all fields applicable, upload picture id and proof of income.] --- Association approval not required. --- No short-term lease or AirBnB (12 months lease only). --- Renters Insurance required. --- Washer and Dryer included. --- Utilities and Lawn-Care is not included. --- Zoned for Bay Lake (Elementary), Horizon West (Middle School) and Windermere (High School).

Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)

Listing Agent: Marcelo Lopes Santana (407-963-2139)

Remarks: Luxury 1 Bedroom / 1 Bathroom Condo for Rent Experience 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, dining, and entertainment. As a rare and special highlight, enjoy breathtaking Disney fireworks views from home??. Residents also enjoy access to a resort-style community pool, creating a relaxed, vacation-like atmosphere year-round.

Listing is courtesy of: JHY REALTY INVESTMENTS, LLC (407-435-0482)

Listing Agent: Haicui Yuan (407-435-0482)