Location: Windermere, Windermere
Do Not Show Listings
13106 ORANGE ISLE DR, WINDERMERE, FL 34786
$4,200195 Days on yellowkey MLS ID: O6348003
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 3312 Built: 2022Community: Sanctuary/Lks/WindermereSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: Sunset Park Elem
High School: Windermere High School
Tax Year:
Middle School: Horizon West Middle School
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)
812 EAST BLVD, WINDERMERE, FL 34786
$7,00017 Days on yellowkey MLS ID: O6394559
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1680 Built: 1951Community: WindermereSingle Family
Elementary School: Windermere Elem
High School: Olympia High
Middle School: Gotha Middle
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)
8921 NEWMARKET DR, WINDERMERE, FL 34786
$2,35031 Days on yellowkey MLS ID: O6390585
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1429 Built: 2006Community: Lakes/Windermere-Lk Reams TwhmTownhouse
Elementary School: Bay Lake Elementary
Remarks: Stunning 3-Bed, 2.5-Bath End Unit Townhouse in Lakes of Windermere – Lake Reams! Enjoy a spacious, sun-filled layout, a sleek kitchen with appliances, and a detached 2-car garage. Perfectly located for easy access to Orlando, yet tucked away in a peaceful, welcoming neighborhood. Shopping, dining, and entertainment are just minutes away! Don’t wait—this gorgeous home won’t last long. Schedule your showing today!
Listing is courtesy of: GOLDEN PACIFIC REALTY INC (407-822-4270)
Listing Agent: Shirley Chen (407-822-4270)
7681 FORDSON LN, WINDERMERE, FL 34786
$2,800212 Days on yellowkey MLS ID: O6344027
0 Days Off yellowkey (back on 3/28/2026)
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 1997 Built: 2016Community: Windermere Sound Ph 2Townhouse
Remarks: Experience modern, energy-efficient living with SOLAR PANELS that provide sustainable power and an exceptionally low electric bill! This beautiful townhome for rent is located in the highly desirable community of Windermere Sound. Offering 4 bedrooms and 2.5 bathrooms, this spacious property features ceramic tile flooring in the main areas and carpet in the bedrooms for added comfort. The open floor plan is perfect for entertaining and includes a second master bedroom with a private bath on the first floor, a modern kitchen with stainless steel appliances, and ample storage space throughout. Enjoy the convenience of a spacious two-car garage and a covered patio (lanai) ideal for family gatherings. Additional upgrades include newly installed pavers in the back area, especially around the trash can space, providing a clean and accessible setup even during rainy seasons. The community offers resort-style amenities, including a pool, tennis and basketball courts, a playground, and a cabana. Conveniently located near shopping centers, major highways, Disney, and top dining options, this home is also zoned for Sunset Park Elementary, Horizon West Middle School, and Windermere High School. Don’t miss the opportunity to live in this stunning, energy-efficient home in the heart of Windermere!
Listing is courtesy of: REILE REALTY CORP (321-299-5123)
Listing Agent: Reina Mendez (321-299-5123)
12225 JOSHUA TREE TRL, WINDERMERE, FL 34786
$2,85026 Days on yellowkey MLS ID: O6392136
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1833 Built: 2016Community: Windermere TrailsSingle Family
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 Agent: Marcelo Lopes Santana (407-963-2139)
14415 CREST PALM AVE, WINDERMERE, FL 34786
$4,475228 Days on yellowkey MLS ID: O6338743
Bed: 6 Bath: 3.5 Liv Area Sq Ft: 3764 Built: 2025Community: Palms At WindermereSingle Family
Elementary School: None
High School: None
Middle School: None
Remarks: Be the First to Call This Home Yours! Brand New Luxurious 2025! Move-In Ready! Pet Friendly! 2-Car Garage! Smart Home! Stunning 6 Bedrooms, Loft, Bonus Room, Stylish Upgrades! Internet & WiFi Included! Step into luxurious, modern living in this expansive 6-bedroom, 3.5-bath, two-story smart home featuring a bright, open-concept layout that seamlessly connects the gourmet kitchen, family room, and dining area. The chef-inspired kitchen boasts a large island, quartz countertops, stainless steel appliances—including a gas cooktop, built-in microwave and oven, bottom-freezer refrigerator, and sleek range hood—plus a spacious walk-in pantry and recessed lighting for a polished, contemporary look. The first-floor master suite is a private retreat with double doors opening to a spa-inspired ensuite featuring a soaking tub, oversized walk-in shower, and dual-sink vanity with ample cabinet space. Upstairs, a versatile loft and bonus room offer endless possibilities for a game room, home office, or media space. Additional bedrooms are generously sized, and all baths reflect the home’s sophisticated style. Additional highlights include a striking metal-frame staircase, durable first-floor vinyl, plush second-floor carpet, a thoughtfully designed laundry with cabinets, sink, and washer/dryer, a 2-car garage, and smart home features including wired ceilings with built-in speakers for seamless entertainment. Enjoy vibrant community amenities including pickleball courts and a playground, all in the highly desirable Windermere area. Move-in ready, luxurious, smart, and perfect for modern family living—schedule your tour today!
Listing is courtesy of: RENT A FLORIDA HOME (863-232-6262)
Listing Agent: Katrina Anarumo (863-232-6262)
12863 HOLDENBURY LN, WINDERMERE, FL 34786
$2,85020 Days on yellowkey MLS ID: O6393800
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2148 Built: 2006Community: Lakes Of WindermereSingle Family
Remarks: 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 the living room and dining room areas with Luxury-vinyl, wood-patterned floors throughout all the house, custom paint, split plan, Updated bathroom, Large Primary Suite with large storage/walking closet room, beautifully stone counters tops, Garden tub, separate shower, Beautiful Kitchen! Brand new Quartz Counter Tops, island & breakfast bar, upgraded stainless appliances, large pantry, with breakfast nook plus a Large adjoining Family room! An extended, covered Lanai/porch with no neighbors in the back. Plus 2-car garage too! Windermere public and private schools are just one to three miles away, convenient to shopping. Living in the Lakes of Windermere means access to top-notch amenities, including a community pool, tennis and basketball courts, and several playgrounds. Plus, you’re zoned for **A-rated schools** and just a short drive from **Disney Parks**, world-class dining, and upscale shopping. Don’t miss your chance to own this exceptional property, Great opportunity!!!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Maria Castro Aversano, Pa (201-694-3982)
7403 FAIRGROVE AVE, WINDERMERE, FL 34786
$4,27555 Days on yellowkey MLS ID: O6383636
Bed: 6 Bath: 3.5 Liv Area Sq Ft: 3841 Built: 2015Community: Windermere SoundSingle Family
Remarks: Spacious 6-bedroom, 3.5-bath unfurnished home offering 3,841 sq ft in the desirable Windermere Sound community. This well-designed floor plan features a downstairs primary bedroom, a large upstairs loft, generously sized bedrooms with walk-in closets, an office area and an expansive kitchen complete with a walk-in butler pantry and ample cabinet space—perfect for entertaining and everyday living. The home features a screened in lanai, fenced in backyard and 3-car garage. Conveniently located near shopping, dining, and major attractions. Move-in ready and available now!
Listing is courtesy of: PABLA PROPERTIES (407-967-2757)
Listing Agent: Sunny Pabla (407-967-2757)
12803 HOLDENBURY LN, WINDERMERE, FL 34786
$3,20021 Days on yellowkey MLS ID: O6389377
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 2439 Built: 2006Community: Lakes/Windermere Ph 02ASingle Family
Remarks: AVAILABLE MAY 2026! Spacious 4-bedroom, 2.5-bath home in the desirable Lakes of Windermere community. This well-designed floor plan features all bedrooms upstairs, with the main floor offering a large living room, formal dining room, office/reading room, and a convenient half bath for guests. The primary suite includes dual vanities, a garden tub, and two large walk-in closets. The kitchen is perfect for cooking and entertaining with ample cabinet and counter space, plus an island with bar seating, and it opens to the living room for a comfortable open feel. Enjoy relaxing evenings on the paved, screened patio overlooking a peaceful pond. Community amenities include pool, tennis and basketball courts, playgrounds, Lake Sawyer pier, Pine Trees Park gazebo, and nearby outdoor recreation areas.
Listing is courtesy of: ICON REALTY ASSOCIATES INC (321-303-5851)
Listing Agent: Silvia Odebrecht (917-374-9711)
12458 LANGSTAFF DR, WINDERMERE, FL 34786
$2,45071 Days on yellowkey MLS ID: O6377797
0 Days Off yellowkey (back on 3/24/2026)
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1560 Built: 2013Community: Lakes/Windermere Lake Reams TwnhTownhouse
Remarks: SPACIOUS TOWNHOME NESTLED IN THE HEART OF WINDERMERE, WHERE THE FINEST SCHOOLS, SHOPPING CENTERS, AND RESTAURANTS ARE PARAMOUNT. FANTASTIC VIEW OF THE WELL-PRESERVED CONSERVATION AREA NESTLED BEHIND THE PROPERTY, PERFECT FOR NATURE LOVERS. TWO CAR GARAGE. CONDO FEATURES AN OPEN FLOOR PLAN, A SPACIOUS LIVING AND DINING ROOM. KITCHEN HAS GRANITE COUNTERS, ISLAND AND FULL SIZE UTILITY ROOM. GOOD SIZED BEDROOMS WITH GARDEN TUBS IN BOTH BATHROOMS AND WALK IN CLOSETS WITH PLENTY OFROOM FOR PERSONAL STORAGE. RESORT STYLE LIVING. MUST SEE!!!
Listing is courtesy of: SUNNY 365 REALTY GROUP (407-574-7048)
Listing Agent: Isabel Sirizzotti (407-361-8236)
8636 POWDER RIDGE TRL, WINDERMERE, FL 34786
$2,90061 Days on yellowkey MLS ID: O6381991
0 Days Off yellowkey (back on 3/21/2026)
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 2086 Built: 2014Community: Windermere Trls Ph 1CSingle Family
Remarks: Come live in this beautiful 4/2.5 home in the Windermere Trails community. The kitchen has stainless steel appliances, 42" cabinets and granite countertops, a good size living room and separate dining room. Upstairs you'll find a large master bedroom with a walk-in closet and en-suite bath; a loft and three more bedrooms that share one bathroom. Laundry room on the second floor. Community amenities include walking trails, playground, dog park, plus a great community pool. The area has great services, a new shopping plaza, and great A-rated schools. ++++ 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 a nonaggressive breed only
Listing is courtesy of: SHINING OAK REALTY (407-399-2298)
Listing Agent: Paul Moscoso (321-210-2456)
13231 OVERSTREET RD, WINDERMERE, FL 34786
$2,85025 Days on yellowkey MLS ID: O6392297
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2306 Built: 2013Community: Windermere TerraceSingle Family
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)
311 E 8TH AVE, WINDERMERE, FL 34786
$6,000 MLS ID: O6364016
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 3805 Built: 1913Community: Windermere TownSingle Family
Remarks: One or more photo(s) has been virtually staged. Luxury Lakefront Executive Rental in Downtown Windermere on Lake Bessie. Now offered at a newly adjusted price, this rare 5-bedroom lakefront home presents one of the most compelling rental opportunities in Windermere.Set on Lake Bessie, this renovated residence offers panoramic water views, flexible living spaces, and true indoor-outdoor Florida living, a feature not commonly found in the current rental inventory. Many competing properties offer limited outdoor space or no water access; this home provides a lakefront setting with room to relax and entertain. The open-concept floor plan features a chef’s kitchen with gas range, custom cabinetry, and premium finishes, flowing into spacious living and dining areas. Two first-floor ensuite bedrooms offer ideal flexibility for guests, home office, or multigenerational living. The second-floor primary suite provides a private retreat with elevated lake views. Outdoor features include a screened porch, landscaped yard, fire-pit area, and koi pond, creating a peaceful setting for everyday living or entertaining. Located in Downtown Windermere, this home offers golf-cart-friendly access to local shops, weekly farmers markets, and community events, with convenient proximity to Orlando’s major employment centers, top-rated schools, and world-class attractions including Disney and Universal. Rarely available as a rental, this lakeview property combines location, space, and lifestyle in one of Central Florida’s most sought-after communities. Schedule your private showing today.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Karen O'Neil (407-789-5565)
11434 JASPER KAY TER #206, WINDERMERE, FL 34786
$2,350 MLS ID: O6390889
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1455 Built: 2007Community: Lakeside/Lks/WindermereCondo
Remarks: Spacious 3-bedroom, 2-bath condominium located on the 2nd floor of a well-maintained community in highly desirable Windermere, FL. This 1,455 sq ft unit offers an open and functional floor plan featuring a large living/dining area, generous natural light, and a well-appointed kitchen with ample cabinetry and counter space. The primary suite includes a walk-in closet and a private bath. Secondary bedrooms are well-sized and ideal for family, guests, or office use. A private balcony provides additional outdoor living space. Washer/dryer included. Centrally located near major attractions, including Walt Disney World; Minutes from Winter Garden Village, dining, shopping, and everyday conveniences; Easy access to SR-429, CR-535, I-4, and major commuter routes; Close to local lakes, parks, and recreational amenities. Secure, well-maintained community environment. The Community offers a resort-style swimming pool. Fitness centre, Clubhouse, Walking paths and landscaped common areas Zoned for top-rated Orange County Public Schools, known for strong academic performance and community engagement.
Listing is courtesy of: MNT INTERNATIONAL (844-668-7589)
Listing Agent: Rizwan Rashid (407-729-7277)
13243 OVERSTREET RD, WINDERMERE, FL 34786
$3,200 MLS ID: S5143317
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2058 Built: 2013Community: Windermere TerraceSingle Family
Remarks: If you choose to rent this beautiful, well-maintained home in a clean, quiet, and safe neighborhood, you’ll love its convenient access to all of Orlando’s attractions. This 3-bedroom, 2-bath home is located near excellent schools, shopping, restaurants, and major roadways, with Disney just 11 minutes away. Situated on a corner lot, the property features a large yard and a screened patio—perfect for families and pets. There is a two-car garage with an automatic opener located at the rear of the home. The spacious master suite is filled with natural light and includes a dual vanity, walk-in closet, and a glass-enclosed walk-in shower. A versatile flex room across from the master suite can be used as an office, playroom, or easily converted into a fourth bedroom if needed. The additional two bedrooms are generously sized. The open living area features wood flooring that continues throughout the home. The kitchen is equipped with large dark cabinets, stainless steel appliances, granite countertops, a tile backsplash, and a convenient breakfast bar. The backyard includes a citrus tree, artificial turf on the patio, and tall bamboo for added privacy. The surrounding flowers and palm trees create a peaceful and relaxing outdoor space. Make your appointment as soon as possible, as the property will be ready for move-in on MAY 1ST.
Listing is courtesy of: LA ROSA REALTY LLC (877-366-2213)
Listing Agent: Rosalina Martinez (321-443-5116)
7307 PENKRIDGE LN, WINDERMERE, FL 34786
$2,900 MLS ID: O6384396
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 1997 Built: 2015Community: Windermere SoundTownhouse
Remarks: Beautiful 4-bedroom, 2.5-bath townhome located in the highly desirable Windermere Sound community in Horizon West. Built in 2015, this home offers approximately 1,997 sq ft of living space with an open floor plan ideal for everyday living and entertaining. The main level features a spacious living and dining area connected to the kitchen, while the primary bedroom provides comfort and privacy. Community amenities include a pool, clubhouse and playground. Conveniently located near shopping, dining, major roadways, and area attractions, and zoned for top-rated Windermere area schools.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Ana Cunha (407-406-0903)
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