Windermere Homes with HOA

Windermere Homes with HOA

Welcome to Windermere, Florida—a picturesque gem nestled in Orange County, known for its stunning lakes, lush landscapes, and a strong sense of community. This charming town, just a stone's throw from the bustling heart of Orlando, offers residents a perfect blend of tranquility and convenience. With its beautiful tree-lined streets and scenic views, Windermere is a haven for those seeking a serene lifestyle without sacrificing proximity to urban amenities.

One of the defining features of Windermere is its commitment to maintaining a high quality of life through well-managed Homeowners Associations (HOA). Many of the homes in this delightful region come with HOA membership, ensuring that the neighborhood remains pristine and inviting. These associations not only help maintain property values but also foster a sense of community among residents. From organizing neighborhood events to overseeing common areas, HOAs in Windermere play a pivotal role in enhancing the overall living experience.

The real estate market in Windermere boasts a variety of options, from elegant single-family homes to luxurious estates, each designed to cater to diverse lifestyles. Many properties feature stunning architectural designs, spacious layouts, and modern amenities, making them perfect for families, retirees, or anyone looking to enjoy the Florida sunshine.

Living in Windermere means embracing a lifestyle filled with outdoor activities, including boating, fishing, and hiking, thanks to its proximity to beautiful lakes and parks. With a rich history, vibrant community spirit, and a wealth of recreational opportunities, Windermere truly embodies the essence of Florida living. Come explore this enchanting town and discover your dream home in a community that feels like family!

Newest Windermere Homes with HOA

7413 Lake Albert Drive, Windermere
$1,799,000
6 Beds ⋅ 6 Baths ⋅ O6451030 MLS
Lakefront living at its finest! This spectacular former model home on beautiful Lake Burden offers breathtaking waterfront views and an exceptional Florida lifestyle. Enjoy boating, water skiing, and fishing right from your own backyard, with a private boat dock and a beautiful swimming pool creating the ultimate outdoor retreat. This impressive 6-bedroom, 6-bathroom residence features a desirable double primary suite layout, oversized bedrooms, beautiful hardwood floors, upgrades throughout, and an oversized private office. The spacious second-floor loft provides additional flexible living space, while two second-floor balconies showcase premier lake views and offers the perfect setting to relax and take in the scenery. Entertain in style with a well-appointed outdoor kitchen and inviting pool area, ideal for gatherings and enjoying the Florida sunshine. Conveniently located near popular restaurants, shopping, and world-famous Disney attractions, this remarkable lakefront property combines space, comfort, and an unbeatable lifestyle. Experience the best of waterfront living in this extraordinary home!

7413 Lake Albert Drive, Windermere
6850 Valhalla Way, Windermere
$2,790,000
5 Beds ⋅ 7 Baths ⋅ O6443303 MLS
Welcome to Valhalla Way, an absolutely turn-key home, in the highly sought-after guard-gated community of Keene’s Pointe. Timeless in character yet fully updated for modern living, this stunning pool home offers a golf-course view of the 14th hole at the renowned Golden Bear–designed Keene’s Pointe Country Club, a beautifully renovated kitchen, soaring ceilings, and more than 5,000 square feet of thoughtfully designed space.Step through the ornate yet fitting front door and the foyer opens into a formal living area, where cathedral ceilings create a bright, open feel and French doors lead to one of the home’s covered lanais. The formal dining room is an inviting space for entertaining, with ceiling and floor details that immediately draw the eye.At the heart of the home, the renovated kitchen is made for both everyday living and gathering. It features fresh two-tone cabinetry, upgraded appliances including a top-of-the-line gas stove, stone counters with a custom backsplash, crown molding, and a center island with prep sink, storage, and bar seating. A breakfast nook offers a more intimate setting with views of the pool.The family room continues the indoor-outdoor flow, with a wall of glass doors opening to a second lanai. On the main floor you’ll also find an office, a bedroom and bath, and the owner’s suite. This private retreat is filled with natural light and highlighted by a double tray ceiling, an accent wall, and a sitting area made for a quiet morning coffee. The spa-like en-suite bath includes a custom dual-sink vanity, dressing table, and oversized walk-in shower.Upstairs, a chic modern staircase leads to additional bedrooms and baths, an open loft with a wet bar for casual entertaining, and a theater room for movie nights.Outside, the home is just as impressive: two covered lanais, an outdoor grill, multiple seating areas, and a custom saltwater pool and spa that has been recently resurfaced with new pool equipment. The backyard feels like a private oasis, with unobstructed golf-course views and lush landscaping. Choosing a home in Keene’s Pointe is choosing a lifestyle unlike any other. This lakefront, guard-gated community offers access to the famous Lake Butler Chain of Lakes, and, of course, golf, tennis, and pickle-ball thru membership into the Golden Bear Club. Set in sought-after Windermere, it also provides easy access to shopping, dining, attractions, and so much more. Zoned for top-rated schools, this breathtaking home delivers everything you could want and then some. Schedule your private tour of Valhalla Way and start making memories that last a lifetime, surrounded by all that Central Florida has to offer.

6850 Valhalla Way, Windermere
11267 Grander Drive, Windermere
$435,000
3 Beds ⋅ 3 Baths ⋅ O6450595 MLS ⋅ 11267 BLDG.
Stunning modern townhome in the desirable Lake Burden community of Windermere! This beautifully designed 3-bedroom, 2.5-bathroom corner-lot townhome offers 1,743 sq ft of living space with all bedrooms upstairs, including a primary suite with walk-in closet. The modern kitchen features dark wood cabinets, granite countertops, a spacious island with room for three barstools, and slate stainless steel GE appliances. High ceilings and an open floor plan create a bright, inviting space perfect for entertaining. Two-car garage. Currently tenant-occupied with a lease through 12/31/2026 - a great opportunity for investors seeking immediate rental income, or for buyers planning ahead. Short walk to the community clubhouse with a large resort-style pool, shaded seating and picnic areas. Lake Burden is a nature lover's paradise featuring a fishing pier, a scenic lake with a mile-long walking and biking trail, outdoor fitness stations, playground and tennis courts, with trails connecting to Downtown Windermere. Zoned for Sunset Park Elementary, Horizon West Middle and Windermere High School. Short-term rentals are not permitted. Schedule your showing today!

11267 Grander Drive, Windermere
14038 Eden Isle Boulevard, Windermere
$709,000
4 Beds ⋅ 3 Baths ⋅ O6450925 MLS
Single-story Windermere Pool Home in the gated community of Eden Isle, with private lake access to Lake Speer. This home has brand-new carpeting in the 4 bedrooms with 5-year-old vinyl laminate flooring throughout the rest of the home. Recent renovations have been done to the kitchen, including new countertops along with recent renovations to the bathrooms. Home had full exterior paint in 2022. This beautiful move-in-ready home is a 4 bedroom, 3 bathrooms with a bonus room and a three-car garage. 2 car garage side-by-side with a single car garage currently being used as a workshop/hobby room. So many great features and perfect for entertaining. Home is about to get a brand new roof which will be installed before closing. This floor plan allows for indoor/outdoor living with its covered lanai and screened-in saltwater pool. An expansive 1/4 acre yard with backyard views of the conservation area. This home is conveniently located near the community private boat ramp. Centrally located in Horizon West, this home is zoned for A rated schools - Keenes Crossing Elementary, Bridgewater Middle and Windermere High School.

14038 Eden Isle Boulevard, Windermere
12930 Vennetta Way, Windermere
$349,000
3 Beds ⋅ 3 Baths ⋅ O6450743 MLS ⋅ 12930 BLDG.
Exceptional value in Windermere! 12930 Vennetta Way offers an outstanding opportunity to own a 3-bedroom, 2.5-bath townhouse with 1,644 square feet of living space and a 2-car attached garage in Berkshire Park at Lake Sawyer South. Located in the Windermere 34786 / Horizon West area, this house combines space, location and a peaceful rear conservation setting. The main level features an open living and dining area, kitchen with solid wood cabinetry and solid-surface counters, interior laundry and a convenient half bath. Upstairs are all three bedrooms, including the primary suite and two additional bedrooms with a shared bath. Smart-home and utility features include a Ring doorbell, under-cabinet lighting and a smart garage door opener. The garage provides additional electrical upgrades, LED lighting and its own A/C unit, creating additional flexibility for storage, a workshop or other uses. Out back, enjoy a conservation view and the uniquely Central Florida experience of seeing and hearing nearby Walt Disney World fireworks from the neighborhood. Lake Sawyer South offers a community pool and clubhouse and is convenient to Horizon West shopping and dining, Walt Disney World, Winter Garden and major Central Florida roadways. Assigned public schools include Sunset Park Elementary, Horizon West Middle and Windermere High, each currently rated A and shown on the Excellent List for the past two years. If you have been searching for a Windermere townhouse for sale, a home in Horizon West, or a property near Walt Disney World, this is a house you will want to see. Value, location, a 2-car garage and conservation views make 12930 Vennetta Way a compelling opportunity in today’s Windermere market.

12930 Vennetta Way, Windermere
13019 Garridan Avenue, Windermere
$620,000
4 Beds ⋅ 4 Baths ⋅ O6451068 MLS
Fully remodeled modern kitchen, Remodeled guest bath, Roof replaced in 2026, so no big-ticket surprises, TWO primary suites, each with a walk-in closet and a double-vanity bath, 3 full baths + half bath, Screened patio between the house and garage, Whole-house water filtration, impeccably maintained. ***No renovations. No repairs. No compromises. Just unpack and start living. Homes like this don't last. Call today and see it before someone else does!

13019 Garridan Avenue, Windermere
4205 Clarice Court, Windermere
$2,899,000
7 Beds ⋅ 9 Baths ⋅ O6450995 MLS
Experience extraordinary luxury and cutting-edge technology at 4205 Clarice Court in Windermere! This impressive 7-bedroom, 8.5-bathroom estate offers 7,042 square feet of heated living space and underwent an extensive renovation down to the studs in 2021–2022. Designed for elevated living and entertaining, the home features custom 42x42 marble tile flooring, brand-new windows, spray foam insulation throughout, and a Control4 smart home system integrating lighting, music, TVs, and intercom. A Tesla solar system with eight backup batteries is designed to power the entire home, including appliances and A/C units. Three tankless water heaters and three A/C units with air filtration and UV-light systems add comfort and efficiency. The stunning remodeled main kitchen features commercial-size refrigerator and freezer, double ovens, two dishwashers, a built-in cappuccino maker, warming drawer, convection cooktop, drawer microwave, ice maker, reverse osmosis water system, and smartphone controls. A second full kitchen upstairs provides additional convenience. The luxurious primary suite features a Kohler smart shower system, while smart toilets are installed in two primary suites and a downstairs bathroom. Enjoy movie nights in the custom theater with a 150-inch screen and theater insulation. Step outside to a spectacular 2022 PebbleTec pool with custom waterfall, waterslide, multicolor LED lighting, smart controls, and both propane and electric pool heaters. The brand-new outdoor kitchen is equipped with a pizza oven, gas grill, cooktop, full-size sink, and soft-serve ice cream machine. Additional highlights include a custom backyard racetrack, indoor and outdoor cameras, ceiling speakers throughout the home and outdoor areas, Wi-Fi 7 mesh networking, epoxy-coated garage flooring, a garage A/C unit, and an optional vehicle lift designed to accommodate up to six-car parking. The property also boasts an incredible variety of more than 25 types of fruits and vegetables grown right in the yard. This one-of-a-kind Windermere estate combines impressive scale, advanced technology, resort-style outdoor living, and exceptional amenities for a truly distinctive lifestyle.

4205 Clarice Court, Windermere
4936 Wise Bird Drive, Windermere
$535,000
4 Beds ⋅ 3 Baths ⋅ O6450351 MLS
Welcome home to your immaculate and move in ready single story home in desirable Summerport with A-rated schools and the Keene's Crossing Elementary School conveniently located a bike ride away within the community and Windermere High School across the street. School commute convenience at its best!!! This light & bright functional floor plan has been recently painted inside and out with a brand new roof in 2025 and new HVAC in 2020, and is the ideal first home for a growing family, a vacation home to get away from those cold winters, or even a retirement home or investment property. From the minute you enter through the covered front porch you are greeted by upgraded Luxury Vinyl Plank flooring through all the living areas and bedrooms with ceramic tile floors in the kitchen and wet areas. The formal living and dining rooms are located across from one another and can serve as the desired flex space that you need making them ideal as a home office, media or game room, home theatre or play room. The kitchen is conveniently located adjacent to the formal living room and features upgraded Quartz counter tops with new appliances in 2021 with a natural gas stove and a brand new dishwasher in 2026. You will literally be cooking with gas in this home...The inviting family room opens up to the kitchen making this the ideal floor plan to entertain your guests and serve your favorite culinary creations on the breakfast bar. The breakfast nook offers serene views of your private wooded backyard. Your master retreat is privately tucked away in the back of the home and features serene wooded views of your private back yard, a spacious walk-in closet and an en suite bath with dual vanities, a garden tub, separate shower and bathrooms stalls. The adjacent bedroom with full bath is ideal for a close by nursery or home office. Bedrooms 2 and 3 are located on the opposite side of the home with a shared bath; ideal as guest bedrooms or the private space that your teenagers need. Long hot showers are as economical as it gets thanks to the natural gas water heater from 2020. Summerport community offers a clubhouse with a hall featuring a cozy fireplace and fully equipped kitchen, a well equipped gym, community swimming pool, tennis and basketball courts, lake front beach volleyball court, playgrounds and BBQ areas. All this in a excellent location conveniently located to grocery stores, shopping, hospitals and a short trip to the area attractions and the airport. MULTIPLE WRITTEN OFFERS RECEIVED

4936 Wise Bird Drive, Windermere
17538 Black Rail Street, Windermere
$1,189,000
5 Beds ⋅ 5 Baths ⋅ O6449981 MLS
WATER VIEW! DISNEY FIREWORKS! 4,999 SQ FT OF LIVING SPACE! TWO PRIMARY SUITES, ONE ON EACH FLOOR! 3 CAR GARAGE! Located in the desirable Enclave community of Windermere, this spacious 5 bedroom home offers an exceptional floor plan with a primary suite on the first floor and a generously sized primary retreat upstairs. Highlights include expansive living areas, formal dining room, private office, dedicated Media Room, and a large upstairs Loft, offering plenty of space for entertaining, relaxing, and everyday living. The spacious kitchen features a pantry and ample storage, complemented by a covered lanai overlooking the water. A well designed Mudroom with extensive custom cabinetry and generous storage, plus a central vacuum system, adds everyday convenience. Beautifully maintained, this residence combines generous living space, comfort, and versatility, with excellent potential to personalize its interiors to your own style. Enjoy the best of Windermere living with beautiful water views, Disney fireworks in the distance, and an exceptional combination of space, functionality, and location.

17538 Black Rail Street, Windermere
13125 Penshurst Lane, Windermere
$599,000
3 Beds ⋅ 2 Baths ⋅ O6449706 MLS
Gorgeous 3 bedroom 2 bathroom home in the desirable subdivision of Lakes of Windermere. The open concept makes the living spaces feel larger and much more inviting. This home also features a split bedroom floorplan for privacy, NO carpet, ceramic tile in all common areas and wood flooring in bedrooms. Home features upgraded kitchen with quartz counter tops, Stainless Steel appliances, New bathrooms, New Roof in2024 and Many More. The kitchen opens up to the family room, perfect for entertaining and enjoying time with guests and family. Off the family room is a the screened patio and completely private back yard, potential to make it the oasis of your dreams. Home is conveniently located near A rated schools, shopping/dining, world class parks and attractions and major roads and highways. Do not miss it! It won't last! Schedule for a private showing today.

13125 Penshurst Lane, Windermere
8867 Herencia Alley, Windermere
$405,000
3 Beds ⋅ 3 Baths ⋅ O6449612 MLS
Welcome to this beautiful townhome in the desirable Legato community in Windermere! This spacious 3-bedroom, 2.5-bathroom home features an open floor plan and a 2-car garage, offering comfort, functionality, and convenience. Enjoy the community swimming pool and a prime location near Walt Disney World, shopping centers, restaurants, and everyday amenities. The property is currently vacant and ready for its next owner. With HOA allowing long-term rentals, this home presents an excellent opportunity for both owner-occupants and investors seeking a rental property in a desirable location. Don’t miss this opportunity!

8867 Herencia Alley, Windermere
4827 Flint Road, Windermere
$559,000
3 Beds ⋅ 2 Baths ⋅ O6449449 MLS
Thoughtfully updated and beautifully maintained, this single-story home is tucked along a quiet neighborhood street in Windermere's sought-after Summerport community. Offering a spacious, private lot with room for a future pool, a flexible floor plan, and valuable recent improvements, this home delivers the comfort, convenience, and lifestyle today's buyers are looking for. Featuring 3 bedrooms, 2 bathrooms, a dedicated office, and 2,085 square feet of living space, the thoughtfully designed floor plan offers an easy flow for everyday living and entertaining. The kitchen features granite countertops, a distinctive copper farmhouse sink, and a casual dining area, adding warmth, character, and functionality to the heart of the home. Plantation shutters, newer carpet, and fresh paint create a welcoming, move-in-ready feel throughout. The privately situated primary suite offers a peaceful retreat, thoughtfully separated from the secondary bedrooms, while the dedicated office with French doors provides an ideal space for working from home or enjoying a quiet escape. With dining space already incorporated into the kitchen, the separate formal dining room offers wonderful flexibility and is currently enjoyed as a game room—perfect for entertaining, hobbies, or creating a space that suits your lifestyle. Step outside to one of the home's standout features—a generously sized, professionally landscaped lot offering wonderful privacy, partial fencing, and plenty of room to create your dream backyard retreat, including space for a future pool. The covered rear porch is an inviting spot for morning coffee, outdoor entertaining, or simply enjoying the peaceful surroundings. Just as appealing are the important improvements already completed, including a roof replaced in 2020 and a new HVAC system installed in 2025, offering added peace of mind. Summerport is one of Windermere's most desirable established communities, known for its mature landscaping, neighborhood lakes, scenic walking paths, and wonderful amenities, including a community pool, clubhouse, fitness center tennis courts, and playgrounds. The community is also served by highly regarded local schools, with the shopping, dining, and entertainment of Hamlin and Winter Garden Village just a short drive away. Disney Fan? You can be on Disney property in 20 minutes. Convenient access to major roadways like the 429 makes exploring all of Central Florida a breeze. With its private, spacious lot, versatile single-story layout, meaningful updates, and inviting neighborhood setting, 4827 Flint Road offers a wonderful opportunity to enjoy the best of Windermere living.

4827 Flint Road, Windermere
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