Location: Windermere , 34786
Do Not Show Listings
12876 CALDERDALE AVE, WINDERMERE, FL 34786
$2,40037 Days on yellowkey MLS ID: O6406093
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1480 Built: 2010Community: Wickham Park 04 05 06 09 10 11 12 01Townhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: Beautiful townhome in desirable Wickham Park. Premium lot with pool view. Townhome features anon floor plan with espresso kitchen cabinets, upgraded backsplash, granite countertops and stainless steel appliances. Private courtyard perfect for grilling and entertaining provides access to two car garage. Upstairs is the Master suite featuring a large window, walk in closet and a master bath with dual sinks. Two additional bedrooms with a full bathroom are also on the second level. Home is walking distance from the community Clubhouse where you will find the pool. Enjoy the community gazebo, walking paths and bike trails. These are some of the many perks of living in Wickham Park. Also, close by are many shops, restaurants and supermarkets. Only a few minutes from Disney.
Listing is courtesy of: DEMAYA REALTY (407-576-6468)
Listing Agent: Victor Jordan (407-576-6468)
11565 MIZZON DR #209, WINDERMERE, FL 34786
$2,300120 Days on yellowkey MLS ID: O6382411
0 Days Off yellowkey (back on 5/7/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1161 Built: 2006Community: Lakeside/Lks/WindermereApartment
Elementary School: Sunset Park Elem
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: Welcome to Lakeside at Windermere! Excellent gated condominium, each building has a elevator. This furniture unit is ready to move in, 2 bedroom and 2 bathroom on a second floor. Excellent location and amenities. Apartment will be available for start contract on March 1st 2026.
Listing is courtesy of: ZARIA REALTY GROUP LLC (407-470-8961)
Listing Agent: Rosa Rodriguez Diaz (787-901-7899)
1243 DINGENS AVE, WINDERMERE, FL 34786
$3,000424 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
High School: Olympia High
Middle School: Gotha Middle
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)
11434 JASPER KAY TER #1101, WINDERMERE, FL 34786
$2,50039 Days on yellowkey MLS ID: O6404802
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1442 Built: 2007Community: Lakeside/Lks/WindermereCondo
Middle School: Horizon West Middle School
Remarks: Beautifully updated 3-bedroom, 2-bathroom ground-floor condo offering 1,442 sq.ft. of thoughtfully designed living space. This unit has been fully renovated and presents in clean, modern condition with brand new interior paint, new laminate flooring throughout, refreshed ceilings, updated lighting fixtures, new ceiling fans, upgraded appliances, new window blinds, and updated hardware. The result is a bright, cohesive, and move-in ready home. The layout is open and functional, with a spacious living area filled with natural light and a well-positioned kitchen that flows comfortably into the main living space. The split-bedroom floor plan provides privacy and flexibility, suitable for a variety of living arrangements. Ground-floor access allows for easy entry with no stairs, adding everyday convenience. Located in a well-maintained community offering a range of amenities including a pool, clubhouse, fitness center, and tennis courts. The property is positioned with convenient access to major roads, shopping, dining, and essential services. Situated within a desirable school zone including Sunset Park Elementary, Horizon West Middle, and Windermere High School. Clean, fully updated, and ready for immediate occupancy, this property stands out as a well-prepared and comfortable rental option in a strong location.
Listing is courtesy of: PINK MIAMI REAL ESTATE (305-605-7465)
Listing Agent: Denis Bochkov (754-248-4417)
12030 SILVERLAKE PARK DR, WINDERMERE, FL 34786
$2,85048 Days on yellowkey MLS ID: S5148671
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2068 Built: 2014Single Family
Elementary School: Bay Lake Elementary
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
$7,500156 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
$1,400130 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
$3,15066 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
Elementary School: Windermere Elem
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)
4326 ISABELLA CIR, WINDERMERE, FL 34786
$14,00066 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)
8414 VIVARO ISLE WAY, WINDERMERE, FL 34786
$5,25067 Days on yellowkey MLS ID: O6397114
0 Days Off yellowkey (back on 4/20/2026)
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3648 Built: 2018Community: Windermere Isle-Ph 2Spa: YesSingle Family
Remarks: Welcome home to your Windermere Isle Mediterranean estate. From the minute you arrive at this move in ready, model like home, you are greeted by a cozy hand cut stone façade & barrel tile roof reminiscent of rich Tuscan architecture. The brick paver driveway leads you to the inviting front porch & through the leaded glass front door to an open floor plan featuring your formal living & dining rooms. The spacious foyer opens up to the great room & gourmet kitchen with breathtaking views of your screened custom pool & covered lanai. Your chef's dream come true gourmet kitchen is well equipped with a large Quartz cooking island with upgraded wainscoting, pendant lights, level 3 kitchen cabinets with crown molding & upgraded handles, dual built-in ovens with a smart convection oven, a natural gas cooktop with a microwave & hood vented to the outside, glass tile backsplash, Whirlpool Gold Series stainless steel appliances and a walk-in pantry. The adjacent breakfast nook & great room open up to the extended 31'x9' covered lanai, making this the ideal area to entertain your guests. Speaking of entertaining, no expense was spared on your privately fenced custom resort style Dreamscapes gas heated, salt water pool & spa, featuring a water fall with 2 cascading bronzed bowls over sparkling Anthracite tile and a sunshelf with bubbler; your ideal lush oasis to escape to as you enjoy your favorite libation after a long day. The spacious rich Travertine pool deck offers plenty of sun bathing options & leads to the bar featuring a stainless steel Paradise Grill ready to cook up your culinary creations. A guest bedroom is conveniently located on the first floor with a walk-in closet & adjacent en-suite bath with tub and shower. The stairs feature an upgraded wrought iron railing and lead you to the 2nd floor bonus room featuring a built in library bookshelf & desk with rolling ladder; the ideal room that can easily accommodate a home theatre, a fitness or yoga studio, home office, game room or your desired flex space. The serene master retreat is privately located in a split floor plan configuration and features Cortec luxury vinyl planking, 2 walk-in closets & a spacious master bath with dual Viatera Quartz vanities with upgraded tile motif wall accents, separate shower & bathroom stalls & a garden tub. The Disney fireworks are just a glimpse away through your master bedroom window. The remaining bedrooms all feature durable Cortec luxury vinyl planking and walk-in closets with the 4th and 5th bedroom sharing a Jack and Jill bath. Peace of mind & energy efficient living at its best with 2 Ring doorbells, 2 Nest smart thermostats, iAquaLink pool automation with mood lighting, upgraded wood plank look ceramic tile floors, barrel tile roof, double pane low E windows throughout, tankless water heater, Tesla car charger in the 3 car garage, and R-38 blown insulation & rigid foam filled concrete block walls; leading to an HERS 60 energy efficiency rating for this Beazer built Sequoia II home. Windermere Isle also features a community pool and cabana, play ground, pond front park with bbq grills with the HOA taking care of the lawn care & fertilization. All this in a great location with excellent schools & just minutes from Disney, Historic Winter Garden, major highways, the Cinepolis Luxury Cinema, shopping at Hamlin Town Center or Winter Garden Village or to visit one of the many close by restaurants that are sure to curb any craving that you may have.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: T.J. O'Donnell (317-246-8190)
12623 LANGSTAFF DR, WINDERMERE, FL 34786
$2,650117 Days on yellowkey MLS ID: O6383047
INCREASED by $150 (6.0%) on 04/04/2026
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1239 Built: 2003Community: Lakes/Windermere-Lk Reams TwnhTownhouse
Remarks: ONE OF A KIND, EXECUTIVE WINDERMERE 2 BEDROOM 2.5 BATHROOMS TOWNHOME FURNISHED & DECORATED! This recently renovated home is in the sought-after Lake Reams Community only a minute drive to the backside of Disney! As you open the front door you are drawn to Upscale Interior, filled with Upgrades & a Warm Family Décor. The eating area overlooks an Enclosed Custom-Made Courtyard leading to a Detached 2 Car Garage with Rear Entry Alleyway that backs up to a Conservation Area. The Appealing Floorplan Features Living Room/Office upfront, Beautiful Open Kitchen with 42-inch Cabinets, Granite Counter Tops & Stainless-Steel Appliances! Special fixtures throughout include Ceiling Lamps & Fans, Crown Moldings, Plenty of storage & Large adjoining Family Room. Light floods the space creating a warm welcoming place to call home. Upstairs features a Large Master Suite with Walk-In Closet overlooking the conservation area, a Master Bathroom with a Large Walk-In Shower, a Separate Garden Tub & Double Vanity with Granite Counters. The Second Bedroom has its own Private Bathroom. The Laundry Closet is also conveniently located upstairs. The Courtyard offers a Private Cozy with Outdoor Furnishings perfect for Entertaining family and friends. The community has a Pristine Pool, Biking/Walking Trails, and a Beautiful Landscape. This Prime Location offers Shopping, Dining, Entertainment and Great Schools, all within minutes. Easy Access to Main Highways. Townhome is partially furnished. Select furniture pieces have been added or staged for marketing and illustration purposes. Not all items shown are included with the property. It is a Fantastic Home in a Great Location! Text for an appointment before is gone!
Listing is courtesy of: ELITE REALTY ENTERPRISES LLC (407-683-4515)
Listing Agent: Ernesto Cisneros (407-683-4515)
8532 BOWDEN WAY, WINDERMERE, FL 34786
$9,800100 Days on yellowkey MLS ID: O6380872
0 Days Off yellowkey (back on 3/18/2026)
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 3885 Built: 1999Community: Keenes PointeSingle Family
Remarks: A stunning fully renovated 4 bedroom, 5 bath plus office ready for you! Features the perfect blend of textures and clean finishes with modern warmth and undeniable sleekness. CArefully thought-out living allows for the overall feel of spaciousness. It has a open layout with height ceilling to welcome you, followed by a chef's kitchen, dinning room and living room. Complete with covered summer kitchen and spacious pool deck.
Listing Agent: Marilene Auge (407-415-7030)
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)
5589 REMSEN CAY LN, WINDERMERE, FL 34786
$2,3401978 Days on yellowkey MLS ID: O5916546
0 Days Off yellowkey (back on 2/13/2021)
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 2600 Built: 2006 Tax: $5,134 (2020)Community: Edens HammockSingle Family
Taxes:$5,134
Tax Year: 2020
Remarks: You're going to love this home! The spacious kitchen is exquisite with gorgeous cabinetry, contemporary counters, and stainless steel appliances. The open floor plan is full of natural light, making this home perfect for entertaining. The primary bath is stunning with designer touches, a separate shower, and a garden tub. The Summerport Residential neighborhood offers amenities such as a tot lot, community pool, and much more! Apply online today. See the floorplan in the photo gallery to picture yourself in this home. Live in a tech-friendly home. Smart Home is a monthly service that helps you manage access to your home and save on your energy bill. With our Smart Home features, you can remotely lock and unlock your front door, control your thermostat, and receive notifications about your home - all through the convenience of your mobile device or computer. Learn more about this service at https://www.invitationhomes.com/smarthomes.
Listing is courtesy of: INVITATION HOMES (954-745-2500)
Listing Agent: Tiffany Baker (407-243-7993)
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