Displaying: For Rent
Location: Windermere
Property Type(s): Single Family
Price: $3,500 to $4,999
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Windermere - 10 properties found
6621 HELMSLEY CIR, WINDERMERE, FL 34786
$3,7496 Days on yellowkey MLS ID: O6405961
0 Days Off yellowkey (back on 6/5/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2897 Built: 2011Community: Preston SquareSingle 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: Welcome home! This 4-bedroom, 3.5-bath home is available for immediate move-in! This property features a comfortable layout with well-apportioned bedrooms and bathrooms, a lovely kitchen with lots of counter and cabinet space, and many desirable features. Enjoy the large back yard and a screened-in patio!! Upstairs features a large loft area and a lovely porch to relax! You will also have access to the gorgeous community swimming pool, playground, and basketball court which are all located just steps from the house. Act now! This one won't last long! All applicants are required to do a credit and background check.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. Lawn care is included with rent!
Listing is courtesy of: 407 PROPERTIES (407-545-2594)
Listing Agent: Steven Simpson (407-545-2594)
11813 VIA LUCERNA CIR, WINDERMERE, FL 34786
$3,50034 Days on yellowkey MLS ID: O6404774
0 Days Off yellowkey (back on 6/4/2026)
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2521 Built: 2005Community: Belmere Village G5Single Family
Elementary School: Lake Whitney Elem
High School: West Orange High
Middle School: SunRidge Middle
Remarks: This stunning and well-maintained single-family home is located in the gated Belmere of Windermere community, just steps from top-tier amenities including the pool, tennis courts, and fitness center, as well as nearby elementary, middle, and high schools, Zoned for A-rated schools. The spacious two-story layout features 5 bedrooms, 3 full bathrooms plus a half bath, a 2-car garage, high ceilings, and an abundance of natural light throughout. The primary suite located at the first floor offers a generous walk-in closet and a large, well-appointed bathroom and one suite upstairs. Conveniently situated near Publix, CVS, 7-Eleven, and a variety of other shops and services nearby, and just 5 minutes from Winter Garden Village. No smoking allowed.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Cristiane Carneiro Spindola Rocha Lima (407-766-9333)
11848 GRAY ROCK TRL, WINDERMERE, FL 34786
$3,8006 Days on yellowkey MLS ID: S5151219
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3662 Built: 2014Community: Windermere TrailsSingle Family
Elementary School: Bay Lake Elementary
Remarks: PLENTY OF SPACE in this beautiful 5-bedroom/4-bath with fully fenced backyard located in desirable Windermere Trails. The home has tile and luxury vinyl throughout (NO CARPET) with plenty of room for families or individuals. Large open floor plan; kitchen with granite countertops, stainless appliances and walk-in pantry; as well as downstairs guest bedroom with ensuite/Jack & Jill bathroom. The master bedroom with large ensuite is on the second floor along with 3 other bedrooms, 2 full bathrooms, laundry room and spacious bonus room. Community includes large 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)
17514 BLACK RAIL ST, WINDERMERE, FL 34786
$3,99515 Days on yellowkey MLS ID: O6410722
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2373 Built: 2014Community: EnclaveSingle Family
Remarks: Luxury one-level Mediterranean Style home located in the highly desirable Enclave community at WINDERMERE. This elegant home is Energy Star Certified and also come with Solar Panels, monthly electric bill is only around $33! Step into the grand entryway with extensive natural light throughout, this 4 bedrooms, 2 baths with an office home deliver a bright open atmosphere. Open floor open, well maintained with ceramic tile on living area and laminate floor on all bedrooms. The master bedroom, the living room and the eating area overlook the tranquil pond at the back, not only creating a beautiful water view, but also providing a peaceful backdrop and exceptional Privacy. Relax in the screened patio or the back yard to enjoy the peaceful water scenery. The chef inspired gourmet kitchen features granite countertops, 42" cabinetry and SS Appliances. The Master Bedroom features elegant tray ceiling. Master bathroom has a garden tub, spacious shower, dual vanities and a large walk-in Closet. All bedrooms have walk-in closets with custom built-in shelving. Great school district! Just a few minutes to Windermere High School and Windermere Preparatory School. Walking distance to Sunset Park Elementary. Enclave is a beautiful community features all roof tile luxury houses. It is located on Chase Road next to Keene’s Point and Gold Bear Golf and Country Club. Easy access to SR 429, Turnpike and 408. Close to Disney Theme Parks. Shopping, dining and attractions are all within a vibrant area. Windermere ranked number one as the best place to live for suburbanites in Florida. Must see! Call now to schedule a showing!
Listing is courtesy of: SUNSHINE REALTY & PROP. MGNT (407-341-8754)
Listing Agent: Man Ching Wong (407-341-8754)
12936 DROXFORD RD, WINDERMERE, FL 34786
$3,60019 Days on yellowkey MLS ID: O6409803
0 Days Off yellowkey (back on 5/23/2026)
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3038 Built: 2006Community: Lakes/Windermere Ph 02ASingle Family
Remarks: Lakes of Windermere STUNNER! This Ashton Woods Kensington floorplan w/ bonus room welcomes you home from the time you drive the gorgeous tree lined streets! Watch the Disney fireworks steps outside of the home! An inviting front porch leads you into the luxuriously upgraded home! As you enter, you are greeted by the formal living/dining area with tons of windows for natural light, HIGH CEILINGS, upgraded CERAMIC WOODGRAIN TILE FLOORING, CROWN MOLDING, and recessed lighting. A 3-WAY SPLIT & OPEN FLOOR PLAN yields the privacy a large family desires. Arched walkways lead you to 3 bedrooms with spacious closets, BRAND NEW Laminate flooring and a fully upgraded bathroom complete with dual sinks. Ceiling fan packages throughout entire home. An entertainer's DREAM KITCHEN awaits you. Truly the heart of the home, this STUNNING two-toned kitchen renovation includes an oversized island with thick cut granite, inlay sink, breakfast bar and additional storage. Stainless steel appliances, 42-inch cabinets, soft close cabinets and pull out drawers, recessed lighting, and a sleek cabinet pantry. Dedicated coffee/beverage bar area leads you to the eating space in kitchen and the spacious Family room, which continues out to a 2018 addition of a SCREENED and COVERED lanai perfect for year-round enjoyment. A double door package leads you into the tasteful primary bedroom and ensuite bathroom where the upgrade continue! Dual Shower heads including a RAIN shower, luxury flooring, makeup vanity and Dual Sinks all tastefully tie into the kitchen upgrades on color palette and natural light. Walk past a guest bathroom and let your imagination wander with the large upstairs bonus/flex room complete with a closet and a full bathroom package (currently used as 5th bedroom). Additionally, a dual A/C system completely replaced 2017, SOLAR PANELS and REVERSE HEAT PUMP WATER HEATER (that cools the garage!) in 2018. SO much flexibility in this floor plan! Lakes of Windermere is an established neighborhood with mature landscaping that offers a pool, tennis, volleyball and basketball courts, dock, parks and playgrounds! MAKE YOUR APPOINTMENT TO VIEW TODAY!
Listing is courtesy of: WEST ORLANDO PROPERTY MANAGEMENT REALTY, LLC (407-922-9169)
Listing Agent: Ricardo Diaz (407-922-6196)
5610 W LAKE BUTLER RD, WINDERMERE, FL 34786
$3,60030 Days on yellowkey MLS ID: O6406597
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3212 Built: 1977Community: Kelso On Lake Butler 5/48 Lot 59Single Family
Elementary School: Windermere Elem
Middle School: Bridgewater Middle
Remarks: Exceptional opportunity to rent a lovely home in Windermere with easy access to Lake Butler Rd, top schools, and everyday conveniences. Enjoy comfort, privacy, and a welcoming neighborhood atmosphere.
Listing Agent: Priscila Lima (321-442-7790)
13272 PENSHURST LN, WINDERMERE, FL 34786
$4,00021 Days on yellowkey MLS ID: S5150230
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3472 Built: 2015Community: Windermere SoundSingle Family
Elementary School: None
High School: None
Middle School: None
Remarks: 5 bedroom, 3 bath home nestled in the community of Windermere Sound. Located near schools, parks, shopping and more, this home is waiting for you! A Large house like this, is sure not to last long.
Listing is courtesy of: BLUEHOUSE REALTY GROUP LLC (929-391-3985)
Listing Agent: Donny Hang Fung (929-391-3985)
13544 RIGGS WAY, WINDERMERE, FL 34786
$3,90033 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)
7401 ELLA LN, WINDERMERE, FL 34786
$3,70042 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)
3636 LAKE BUYNAK RD, WINDERMERE, FL 34786
$3,50040 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)
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