Location: Windermere
Do Not Show Listings
8278 PROCIDA ISLE LN, WINDERMERE, FL 34786
$5,50033 Days on yellowkey MLS ID: O6403366
Bed: 6 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4176 Built: 2019Community: Windermere Isle-Ph 2Spa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: 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, crown molding, Chef kitchen, backsplash, stainless steel appliances with gas stove, walk-in pantry and Office Nook area. The huge Loft gives you an extra space for a secondary living area. The MASTER SUITE has a large double walk-in closet. Unwind from the day in your GARDEN BATH with soaking tub and semi-frameless glass shower with double shower head with rain showerhead. Another 2 bedrooms have jack and jill bathroom to share, Second floor laundry room with sink. Screen lanai with ceiling fan for enjoying outdoor living. Epoxy garage floor paint. Windermere Isle offers residents a Community Pool, Cabana and Playground. Top rated school, Located close to 429, Disney and Hamlin Shops.
Listing is courtesy of: AGENT GROUP REALTY (843-656-0550)
Listing Agent: Li Xue (407-919-3796)
13231 OVERSTREET RD, WINDERMERE, FL 34786
$2,85073 Days on yellowkey MLS ID: O6392297
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2306 Built: 2013Community: Windermere TerraceSingle Family
Elementary School: Sunset Park Elem
High School: Windermere High School
Middle School: Horizon West Middle School
Remarks: 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 the best place for family and friends' gatherings. You can also enjoy Disney fireworks every night. Downstairs there is a large master bedroom, upstairs has two bedrooms and large play space. Master bathroom has double sink, granite countertop, and a large shower room. Laundry room with a large space for storage. This highly sought-after community features quality built and well-maintained homes. Amenities include walking trails, playgrounds, and a huge community pool. A-rated schools and Shopping Center with Publix Supermarket is just at the corner. Easy commute to most parts of Orlando. Basic tenant requirements: 675+ credit score, no BAD history, no BAD RENTAL history, income 3x monthly rent as a household.
Listing is courtesy of: CINO INTERNATIONAL INC (407-354-3318)
Listing Agent: Daniel Zheng (407-683-1881)
11917 CAMDEN PARK DR, WINDERMERE, FL 34786
$5,50029 Days on yellowkey MLS ID: O6403295
0 Days Off yellowkey (back on 5/18/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3030 Built: 2006Community: Keenes PointeSingle Family
Elementary School: Windermere Elem
Middle School: Bridgewater Middle
Remarks: This stunning single-story home in the guard-gated community of Keene’s Pointe offers 4 bedrooms, 3 bathrooms, and 3,030 square feet of beautifully designed living space. The open-concept floorplan is enhanced by soaring ceilings and an abundance of windows, filling the home with natural light. Upon entry, you’re welcomed by elegant formal spaces—including a foyer, living room, dining room, and private study—featuring rich hardwood flooring, architectural arches, columns, and crown molding. The living room’s French doors open to a spacious screened-in lanai, perfect for indoor-outdoor living. The heart of the home is the expansive kitchen and family room, seamlessly connected for effortless entertaining. The kitchen boasts a large island, breakfast bar, cozy nook, granite countertops, stainless steel appliances, double ovens, a gas cooktop, and a built-in organization desk. The adjoining family room features a vaulted ceiling and French doors leading to the lanai, while the entire area is finished with easy-care ceramic tile. The oversized primary suite is a true retreat, highlighted by a tray ceiling with crown molding and a luxurious en-suite bath complete with dual vanities, a recessed makeup area, garden tub, separate shower, and generous closet space. Three additional bedrooms, two full bathrooms, a dedicated laundry room, and a three-car garage complete the interior. Located in Camden Village, a peaceful enclave within Keene’s Pointe, this home offers convenient access to both the country club and the community’s main entrance.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Brynn Allen (407-617-8963)
5243 W LAKE BUTLER RD, WINDERMERE, FL 34786
$8,999194 Days on yellowkey MLS ID: O6362021
REDUCED by $1,000 (10.0%) on 05/12/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 3255 Built: 1996Community: Summerport BeachSingle Family
Remarks: 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 breathtaking views from virtually every room, creating the ultimate backdrop for serene living and effortless entertaining. At the water's edge, enjoy a two-story dock complete with a hydraulic boat slip and jet ski lift, plus your own private boat ramp, a rare and coveted feature for lake enthusiasts. After a day on the water, unwind in the solar-heated swimming pool, framed by panoramic lake vistas. Inside, the heart of the home is the expansive luxury kitchen, thoughtfully designed with high-end finishes and an abundance of upgrades, including spice organizers, pull-outs, and generous storage solutions. Multiple flex spaces offer endless possibilities for a home gym, office, or den. The main level master suite is a peaceful sanctuary with sweeping lake and pool views. It connects to a conditioned Florida room, perfect for morning coffee or for unwinding at sunset. Upstairs, a bright loft area leads to two spacious bedrooms, connected by a stylish Jack-and-Jill bathroom. One of the bedrooms opens to a private lakeview deck, offering a stunning vantage point over the water. Additional features elevate this home even further! A well-equipped greenhouse, an air-conditioned shed with a garage door, perfect for storing jet skis, and multiple beautifully finished indoor and outdoor living spaces designed for comfort, elegance, and entertaining. Whether you're boating, lounging by the pool, tending your greenhouse, or simply enjoying the peaceful waterfront scenery, this home offers an unparalleled lifestyle. Must meet resident selection criteria. Renters insurance is required. All residents are automatically enrolled in a master renters insurance policy for $11.95 per month. Residents can opt out of the master policy by providing proof of their own policy that meets minimum requirements.
Listing is courtesy of: 407 PROPERTIES (407-545-2594)
Listing Agent: Steven Simpson (407-545-2594)
307 W 4TH AVE, WINDERMERE, FL 34786
$5,475489 Days on yellowkey MLS ID: O6275058
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3190 Built: 1968Community: Windermere TownSingle Family
Remarks: One or more photo(s) has been virtually staged. Available for lease, this refined single-story pool residence is located in the Town of Windermere, just moments from Main Street and the downtown district’s dining, shopping, and community amenities. Positioned on an oversized corner lot beneath mature oak trees, the property offers a private and well-composed setting with thoughtful indoor and outdoor spaces. The residence features four bedrooms, including two primary suites, and three full bathrooms. The kitchen is designed with both style and functionality in mind, offering stainless steel appliances, dual refrigerators, a professional gas range, granite countertops, a subway tile backsplash, and a breakfast bar that connects seamlessly to the main living area. The adjacent living space is highlighted by Saltillo tile flooring, a wood-accented ceiling, expansive windows, and skylights that fill the home with natural light. One primary suite includes an ensuite bathroom with dual vanities, a soaking tub, and a separate shower, along with a spacious walk-in closet and dressing area. Sliding glass doors provide access to a private patio overlooking the pool. Outdoor living is further enhanced by a screened lagoon-style lap pool with a newer heater, paver decking, and multiple patio areas designed for relaxation and entertaining.
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Rob Gaudreau (407-579-2737)
12761 BIDEFORD AVE, WINDERMERE, FL 34786
$3,40089 Days on yellowkey MLS ID: O6387477
0 Days Off yellowkey (back on 5/16/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3011 Built: 2006Community: Lakes Of WindermereSingle Family
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)
325 MAGNOLIA ST, WINDERMERE, FL 34786
$9,50019 Days on yellowkey MLS ID: O6407418
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3975 Built: 1954Community: Windermere TownSpa: NoSingle Family
High School: Olympia High
Middle School: Gotha Middle
Remarks: 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 your own paradise, complete with a sparkling pool and a private covered dock to use for easy lake access. Whether you enjoy water skiing, fishing, or simply cruising along the tranquil waters, this property is a water enthusiast's dream come true. This gem also boasts the advantage of a walkable downtown area, allowing you to immerse yourself in the charm of the community. Don't miss the vibrant weekly Friday farmers market, 4th Fridays Food Trucks, coffee shop, hometown diner and local brewery - easily walk or bike from your front door. The town offers ten public parks, three public piers, boat ramps, tennis courts, basketball courts and a library. Luxury living, unmatched natural beauty, and a welcoming small town atmosphere await you in this remarkable home. Don't let this opportunity slip away. Schedule your private showing today and start enjoying the lakefront living lifestyle.
Listing is courtesy of: REVEL REALTY LLC (407-876-6448)
Listing Agent: Rebekkah Boskovich (321-438-3307)
13544 RIGGS WAY, WINDERMERE, FL 34786
$3,90025 Days on yellowkey MLS ID: O6404050
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2696 Built: 2007Community: Enclave/Berkshire Park B G H ISingle Family
Elementary School: Sunrise Elem
Remarks: 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 3-car garage. Upon entering, you're welcomed by an inviting formal living and dining area filled with natural light, highlighted by elegant arched entryways and a flexible layout ideal for both everyday living and entertaining. Toward the rear of the home, the open-concept kitchen and family room create a warm gathering space with ample cabinetry, generous counter space, and direct access to the large screened-in patio, perfect for relaxing outdoors or enjoying Florida evenings with added privacy. Upstairs, you'll find four generously sized bedrooms, including an expansive primary suite featuring tray ceilings, arched architectural details, dual vanities, a soaking garden tub, separate shower, and two walk-in closets. One of the guest bedrooms also features its own private ensuite bathroom, making it ideal for guests, multigenerational living, or a private home office setup. A second-floor laundry room and multiple linen closets add everyday convenience. Located in a sought-after Windermere community known for its proximity to top-rated schools, shopping, dining, major roadways, and nearby attractions, this move-in ready home offers exceptional value in one of Central Florida’s most desirable areas. Schedule your private showing today.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Evan Caulfield (407-432-9767)
11051 CONISTON WAY, WINDERMERE, FL 34786
$13,00073 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
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)
12706 WESTSIDE VILLAGE LOOP, WINDERMERE, FL 34786
$3,27538 Days on yellowkey MLS ID: O6402155
0 Days Off yellowkey (back on 5/11/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2665 Built: 2018Community: Westside VillageSpa: NoSingle Family
Elementary School: Bay Lake Elementary
Remarks: Great House, Great Location! 4 beds and 3.5 baths just a few years old around the corner from the Lakeside Village Center in Windermere. This home is right across the street from the playground and pool center. With decorative pavers for the driveway, huge covered front porch. Choose to run across the street to take a dip in the gorgeous community pool, or sit on the front porch watching your friends and neighbors go by. For more privacy, enjoy the huge covered and screened-in lanai in the back with a back yard having partial block privacy wall on back and one side. Inside the home has a first floor bedroom and full bath, open den/office/formal dining, back study room or office with separate glass door to the back lanai and half bath powder room. The main great room is open living, kitchen, and dinette with French doors and side lights to outside. The kitchen has huge island with sink and breakfast bar, darker cabinets with black granite and crown molding. All stainless steel appliances. The master bedroom upstairs has a walk-in closet, large master bath with Separate vanities. One on each side of the garden tub and a separate walk in shower and a separate toilet room. Bedrooms 3 and 4 are separated by the hall bath, and laundry room with washer and dryer are near the stairs. The garage has a speckled painted floor. The Westside Village community has a nice playground next to the resort style pool and plenty of walking trails around the ponds next to the forest. A great location near the heart of Windermere with A-rated schools and shopping around the corner. You will love calling this place home. Please Email for more info or set up showing. information deemed reliable but not guaranteed. please verify
Listing is courtesy of: SPRING REALTY ONE LLC (407-340-1754)
Listing Agent: Bryce Rysewyk (407-340-1754)
3999 ISABELLA CIR, WINDERMERE, FL 34786
$15,950346 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)
8363 BOWDEN WAY, WINDERMERE, FL 34786
$6,50035 Days on yellowkey MLS ID: O6402777
0 Days Off yellowkey (back on 5/6/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2666 Built: 1999Community: Keenes PointeSpa: YesSingle Family
Remarks: Welcome to Keene’s Pointe in Windermere! Stunning 4-bedroom, 3-bath, one-story pool home in a guard-gated golf community. This move-in ready residence features a spacious open floor plan, formal living & dining rooms, and a gourmet kitchen with granite countertops, stainless steel appliances, and abundant cabinetry. The family room with dual-sided stone fireplace flows into a private sitting area, perfect for relaxing or entertaining. The oversized primary suite offers two walk-in closets and a fully renovated spa-style bathroom. Three additional bedrooms provide flexibility for guests, a home office, or family living. Step outside to your private backyard oasis with a resurfaced pool, new travertine deck, and a fully equipped outdoor kitchen—ideal for Florida outdoor living and entertaining. Landscape and exterior lighting enhance curb appeal and ambiance. Located in Keene’s Pointe, enjoy 24-hour guard-gated security, a Jack Nicklaus-designed golf course, clubhouse amenities, and scenic walking trails. Zoned for top-rated Windermere schools and just minutes from shopping, dining, and major Orlando attractions. Pool maintenance included. Schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Sharon Brandt (407-310-3623)
7401 ELLA LN, WINDERMERE, FL 34786
$3,70034 Days on yellowkey MLS ID: O6402770
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2350 Built: 2015Community: Windermere Sound Ph 2Single Family
Remarks: 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 entertaining. The kitchen is well equipped with granite countertops, stainless steel appliances, and a large island. The main-floor master suite provides convenience and privacy, complete with a spa-like en suite and double vanity. Upstairs includes three spacious bedrooms, a versatile loft suitable for a home office or secondary living area, and a conveniently located laundry room. Residents can also enjoy views of nearby Magic Kingdom fireworks just a few miles away. The Windermere Sound community offers resort-style amenities, including a pool, tennis courts, basketball courts, and more, with shopping, dining, and top-rated schools nearby. Important: The in-law suite located above the garage is NOT included in the lease and is not available for tenant use. It is occupied by the owner only occasionally (approximately once or twice a year). The suite has a completely separate entrance, maintaining privacy for the main residence. The garage is fully available for tenant use.
Listing is courtesy of: AUTHENTIC REAL ESTATE TEAM (407-440-1010)
Listing Agent: Fernanda Berretta (561-229-6717)
1243 DINGENS AVE, WINDERMERE, FL 34786
$3,000412 Days on yellowkey MLS ID: O6300024
REDUCED by $1,000 (25.0%) on 05/02/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1928 Built: 1969Community: Gotha TownSingle Family
Elementary School: Thornebrooke Elem
Remarks: WONDERFUL WELCOME HOME IN WINDERMERE. READY TO MOVE IN. TOP RATED SCHOOLS IN A FAMILY COMMUNITY, NEAR DISNEY, DINING AND ENTERTAINMENT, MAY BE RENTED FULL FURNISHED, FEELS LIKE COUNTRY LIVING, BUT CLOSE TO EVERYTHING, so bring your boat, camper, or build the Gotha Park is just a short walk away, offering tennis courts, a pavilion, and a tot lot for the little ones. LOCATION, LOCATION, LOCATION! Zoned for Thornebrooke Elementary, a top-rated school. Hungry but don’t feel like cooking? Take a leisurely stroll to Yellow Dog Eats—your four-legged friend will love the walk, too! At the end of the day, this isn’t just a house—it’s your own personal retreat. Whether you’re relaxing, entertaining, or making memories, this is where everyone will want to gather. Listing rent monthly front house 3 bedroom and 2 bathroom living area, dinning area, Family room. Also the in law in the backyard one bedroom or loft with kitchenette and living area just for $1K add to the lease. Schedule your private tour today!
Listing is courtesy of: REALMULTIPROPERTY LLC (407-412-8598)
Listing Agent: Peter Useche (407-412-8598)
12030 SILVERLAKE PARK DR, WINDERMERE, FL 34786
$2,85036 Days on yellowkey MLS ID: S5148671
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2068 Built: 2014Single Family
Remarks: LOCATION, LOCATION, LOCATION. Beautiful 4/bed 2.5/bath home in desirable Windermere Trails. Watch Disney fireworks nightly from spacious 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 bedroom is upstairs along with three other bedrooms, laundry room and loft area perfect for an office. In walking distance to Bay Lake Elementary. Community includes clubhouse with large swimming pool, playground, cabanas, greenspace and fitness parks, walking trails and dock access. Conveniently located close to highly-rated schools, shopping and restaurants including Lakeside Village Center, Westside Shoppes and Winter Garden Village, as well as Disney, FL-429, FL-408, and I-4. -- No short-term, AirBnB or roommates. Renter’s insurance required.
Listing is courtesy of: TOPSKY REALTY INC (407-476-6189)
Listing Agent: Carolyn Hunt (407-257-0937)
2844 MIDSUMMER DR, WINDERMERE, FL 34786
$7,500144 Days on yellowkey MLS ID: O6371115
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3328 Built: 1979Community: Lake Down Shores RepSingle Family
Remarks: Fabulous gated one acre Windermere Chain of Lakes Estate with Private tennis court is currently available for lease, This 5 bedroom 3 1/2 bath includes in-law suite with private entrance. New boat dock for the avid boater along with sandy beach for ultimate waterfront entertainment. Enjoy the beautiful west facing sunsets from your large covered patio or dine beside your double sided wood burning fireplace.
Listing is courtesy of: WINDERMERE COCOA BEACH CENTER (407-876-1032)
Listing Agent: Dennis Conklin (407-876-1032)
8347 LOOKOUT POINTE DR, WINDERMERE, FL 34786
$1,400118 Days on yellowkey MLS ID: O6378814
0 Days Off yellowkey (back on 5/3/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 500 Built: 2016Community: Windemere Trls Ph 3BSingle Family
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)
8520 GREENBANK BLVD, WINDERMERE, FL 34786
$3,15054 Days on yellowkey MLS ID: O6396741
0 Days Off yellowkey (back on 4/29/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1726 Built: 2004Community: Lakes/Windermere-PeachtreeSingle Family
Remarks: Beautiful and inviting home located in the heart of Windermere, nestled within a charming gated community. Enjoy the rare opportunity to watch Disney fireworks right from your own backyard. Designed for modern living, this home features an open-concept floor plan that flows seamlessly, perfect for both everyday comfort and entertaining. The fully fenced backyard offers privacy and the ideal space for family gatherings, barbecues, and outdoor enjoyment. Additional highlights include solar panels for enhanced energy efficiency, a spacious two-car garage, and a welcoming front porch perfect for relaxing. Residents enjoy access to community amenities including a sparkling swimming pool, playground, and beautifully maintained green spaces. Ideally located near top-rated A+ schools, as well as shopping, dining, and everyday conveniences, this home offers the perfect blend of comfort, efficiency, and location in one of Central Florida’s most desirable areas.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Umberto Da Cunha Neto (407-690-3539)
3636 LAKE BUYNAK RD, WINDERMERE, FL 34786
$3,50032 Days on yellowkey MLS ID: O6403466
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1855 Built: 1977Community: Lake Buynak EstatesSingle Family
Remarks: Looking for seclusion? One plus acre waterfront. No HOA. Adorable, clean available June 1st. Bring your boat, RV, pets. Quiet treed drive located near the Town of Windermere. Complete with stainless appliances, washer, dryer. Large screened porch. Tile floors throughout. Decorative fireplace in family room. Room to Breathe!! Check it out today. For Application: https://apply.link/rhwVwSc
Listing is courtesy of: UPSIDE REAL ESTATE INC (407-308-5750)
Listing Agent: Judy Black (407-810-1803)
4326 ISABELLA CIR, WINDERMERE, FL 34786
$14,00054 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
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)
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