Windermere Homes under $750,000

Windermere Homes under $750,000

Welcome to Windermere, Florida – a picturesque gem nestled in the heart of Orange County. Known for its serene lakes, lush landscapes, and charming small-town vibe, Windermere offers residents a unique blend of tranquility and community spirit. With its stunning waterfront views and vibrant local culture, this idyllic town is a perfect place to call home.

Windermere is renowned for its friendly atmosphere, where neighbors become friends, and every corner of the community exudes warmth. The town is dotted with beautiful parks, scenic walking trails, and inviting playgrounds, making it an excellent choice for families, retirees, and everyone in between. The local schools are highly rated, and the community is actively involved in creating a nurturing environment for children to thrive.

For those seeking to invest in a home in this enchanting area, Windermere offers a variety of options under $750,000. Whether you’re looking for a cozy single-family home, a modern townhome, or a spacious property with a backyard oasis, there’s something for everyone. Many homes in this price range boast contemporary designs, open floor plans, and convenient access to local amenities, including shopping, dining, and recreational activities.

Living in Windermere means enjoying a relaxed lifestyle while being just a short drive away from the bustling attractions of Orlando. With its blend of natural beauty, community charm, and affordable housing options, Windermere is truly a hidden treasure waiting to be discovered. Come explore your dream home in this delightful town, where every day feels like a vacation!

Newest Windermere Homes under $750,000

4936 Wise Bird Drive, Windermere
$535,000
4 Beds ⋅ 3 Baths ⋅ Summerport Creeks Run SubDv. ⋅ 34786 Zip Code
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.

4936 Wise Bird Drive, Windermere
13125 Penshurst Lane, Windermere
$599,000
3 Beds ⋅ 2 Baths ⋅ Lakes/Windermere Ph 03 P & Q SubDv. ⋅ 34786 Zip Code
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 ⋅ Legado SubDv. ⋅ 34786 Zip Code
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 ⋅ Summerport Ph 05 SubDv. ⋅ 34786 Zip Code
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
8276 Maritime Flag St Unit 1204, Windermere
$324,900
3 Beds ⋅ 2 Baths ⋅ Lakeside/Lk/Windermere Ph 12 SubDv. ⋅ 34786 Zip Code
Virtually Staged. Welcome to this beautiful 3-bedroom, 2-bathroom first-floor condo in the desirable Lakeside at Lake Windermere community! Offering an attractive combination of location, comfort, and investment potential, this property is an excellent opportunity for both homeowners and investors looking for a rental property in the heart of Central Florida. Conveniently located near Walt Disney World, Windermere, shopping, restaurants, and major roadways including I-4 and the 429, this condo offers easy access to the area's top attractions, employment centers, and everyday conveniences. Its location also makes it an appealing option for renters seeking proximity to Disney, the Windermere area, and nearby schools. Inside, you'll find a functional open-concept split floor plan with quality laminate flooring throughout. The kitchen features beautiful wood cabinetry, granite countertops, modern appliances, and plenty of counter space. The spacious dining area and great room create an inviting setting for entertaining family and friends. The generously sized primary bedroom accommodates a king-size bedroom suite and features a walk-in closet. The primary bathroom includes dual sinks, ample cabinetry, and a bathtub/shower combination. Two additional bedrooms are situated on the opposite side of the condo, conveniently located near the second full bathroom and laundry closet. Step through the sliding glass doors to enjoy your private screened-in patio, perfect for relaxing and enjoying Florida's year-round outdoor lifestyle. Residents enjoy a variety of community amenities, including a gated entrance, valet trash service, a beautiful clubhouse, a resort-style destination pool, a sand volleyball court, and a barbecue area. An Excellent Investment Opportunity you don't want to miss!!

8276 Maritime Flag St Unit 1204, Windermere
11963 Vermillion Avenue, Windermere
$430,000
3 Beds ⋅ 3 Baths ⋅ Windermere Trails SubDv. ⋅ 34786 Zip Code
Virtually Staged. LOCATION, LOCATION, LOCATION! Welcome to Windermere Trails, one of Windermere’s most desirable communities. This beautiful 3-bedroom, 2.5-bath townhome offers 1,676 sq. ft. of living space, a 2-car garage, and an unbeatable location just steps from Bay Lake Elementary School. Enjoy the convenience of having shopping, dining, and everyday essentials nearby, including Publix at Lakeside Village, while being just minutes from Walt Disney World and major roadways. The home features an open and functional floor plan, stainless steel appliances, ceramic tile throughout the first floor, and spacious living areas designed for comfortable everyday living. Windermere Trails offers resort-style community amenities including a pool, splash pad, playground, dog park, open-air pavilion, walking areas, and beautiful green spaces. Exceptional Windermere location, convenient access to highly regarded area schools, shopping, dining, entertainment, and everything the Horizon West area has to offer. Schedule your showing today!

11963 Vermillion Avenue, Windermere
8576 Powder Ridge Trail, Windermere
$620,000
4 Beds ⋅ 4 Baths ⋅ Windermere Trails SubDv. ⋅ 34786 Zip Code
Virtually Staged. Welcome to this exceptional, energy-efficient modern residence built in 2017, perfectly positioned with tranquil lake views in one of the area’s most desirable neighborhoods. Offering a spacious and thoughtfully designed main home alongside a full apartment—ideal as a private guest suite or a lucrative rental income opportunity—this property delivers unmatched versatility and lifestyle appeal. The main home features an expansive open-concept layout designed for daily living and sophisticated entertaining. The bright, airy living and dining area flow seamlessly into a modern kitchen, equipped with premium stainless steel appliances, abundant counter space, and extensive storage. A second family room offers additional possibilities for entertaining and comfort. Upstairs, the spacious primary suite features a dual-sink vanity and a walk-in shower. Two additional well-sized bedrooms offer exceptional flexibility for family, guests, or a home office. A large balcony spans the entire width of the home on both stories. A standout feature of this property is the fully independent detached granny flat, complete with its own kitchenette, bedroom, living room and full bathroom. Whether utilized for multi-generational living, visiting family, or leased out for steady rental income, this private space adds extraordinary value. Additional highlights include a secure two-car garage and patio. Situated in a vibrant community, residents enjoy resort-style amenities including a sparkling pool overlooking the lake, a dedicated dog park, playgrounds, scenic walking trails, and a picnic pavilion. This home boasts a few minute walk from top-rated schools, including Bay Lake Elementary, Horizon West Middle School and Windermere High School. This prime, highly sought-after location is just a few minute drive from historical downtown Windermere, equipped with charming boutiques and picturesque views, and in close proximity to top shopping and dining at Lakeside Village and Winter Garden Village, as well as world-famous Orlando attractions including Disney, Universal Studios, and SeaWorld. A rare find combining modern 2017 construction, income potential, and a premium neighborhood setting—schedule your private tour today!

8576 Powder Ridge Trail, Windermere
8179 Maritime Flag Street Unit 206, Windermere
$350,000
3 Beds ⋅ 2 Baths ⋅ Lakeside/Lks/Windermere SubDv. ⋅ 34786 Zip Code
Enjoy easy Florida living in this beautifully maintained first-floor, 3-bedroom, 2-bathroom condo in Windermere. The split floor plan offers privacy, while premium upgrades and 18-inch tile throughout the common areas make this move-in-ready home both comfortable and practical. Spend your weekends enjoying the community pool, fitness center, clubhouse, volleyball court, and grilling and picnic areas. Tennis courts and a playground are also available through the master association. HOA fees include water, sewer, garbage collection, and exterior maintenance, giving you more time to enjoy your surroundings. Conveniently located near Publix, Starbucks, shopping, and dining, this Windermere condo puts Walt Disney World, Disney Springs, Horizon West, and Winter Garden within easy reach. Whether you’re looking for a primary residence or a seasonal retreat, this home offers comfort, convenience, and more time for the Florida lifestyle you love.

8179 Maritime Flag Street Unit 206, Windermere
6858 Merrick Landing Boulevard, Windermere
$595,000
3 Beds ⋅ 2 Baths ⋅ Vineyards/Horizons West Ph 1a SubDv. ⋅ 34786 Zip Code
YOUR OWN PRIVATE SPA, A WINDERMERE ADDRESS, AND LANDSCAPING YOU DON’T HAVE TO WORRY ABOUT—6858 Merrick Landing Blvd makes Florida living easy. Located in the desirable community of THE VINEYARDS IN WINDERMERE, FL, this spacious 3-BEDROOM, 2-BATH HOME + BONUS ROOM offers 2,115 SQ FT of thoughtfully designed single-story living with a split floor plan that creates both connection and privacy. Step inside to an open and inviting interior with vaulted ceilings, crown molding, and a kitchen positioned at the heart of the home featuring an OVERSIZED CENTER ISLAND, GRANITE COUNTERTOPS, 42-INCH CABINETRY, STAINLESS STEEL APPLIANCES, and a walk-in pantry overlooking the main living and dining spaces. The BONUS ROOM gives you valuable flexibility without sacrificing a bedroom—perfect for a home office, media room, playroom, fitness space, or second lounge. Privately positioned away from the secondary bedrooms, the OVERSIZED PRIMARY SUITE offers plenty of room for a sitting area, along with a generous walk-in closet and en-suite bath featuring dual vanities and a large walk-in shower with bench. Outside, unwind in your own PRIVATE IN-GROUND SPA, creating a relaxing retreat for quiet mornings or Florida evenings at home. Life in THE VINEYARDS makes ownership even easier, with the HOA including LANDSCAPING/GROUND MAINTENANCE AND PEST CONTROL, plus access to a community pool, parks, playgrounds, sidewalks, and green spaces. The location is another major advantage—currently zoned for INDEPENDENCE ELEMENTARY, BRIDGEWATER MIDDLE, AND WINDERMERE HIGH SCHOOL, with Windermere High located directly nearby, while HORIZON WEST, HAMLIN, WINTER GARDEN VILLAGE, DISNEY SPRINGS, WALT DISNEY WORLD, shopping, dining, and major roadways are all within convenient reach. At 6858 Merrick Landing Blvd, the location is desirable, the floor plan is flexible, and the lifestyle is refreshingly easy. Schedule your private showing today.

6858 Merrick Landing Boulevard, Windermere
7030 Mapperton Drive, Windermere
$649,000
4 Beds ⋅ 3 Baths ⋅ Lakes Of Windermere SubDv. ⋅ 34786 Zip Code
Virtually Staged. WHIMSICAL POOL HOME | Welcome to the highly desired community of the Lakes Of Windermere. Enjoy the beauty of park-side living and the comfort of your own private pool retreat in this immaculate, move-in-ready home in the desirable Lakes of Windermere community. Featuring four bedrooms, three bathrooms, and 2,455 square feet of thoughtfully arranged living space, this inviting single-story residence features an expansive open floor plan. A roof replaced in 2023, air-conditioning system replaced in 2021, new water heater, and newly replaced pool cage screens add meaningful value to a home that is beautifully prepared for its next chapter. A welcoming covered front porch overlooks the treed community park across the street, creating a peaceful setting for morning coffee or an unhurried evening outdoors. Inside, generous living spaces and an airy, flowing layout provide room to gather, entertain, and settle comfortably into everyday life. The spacious formal living and dining areas offer flexibility for both intimate occasions and larger celebrations, while the heart of the home unfolds into an expansive kitchen and adjoining family room. A preparation island, breakfast bar, abundant cabinetry, generous counter space, dual dining room options and stainless steel appliances make the kitchen as practical as it is inviting. Its open connection to the family room keeps conversation flowing and brings the main living spaces together with views toward the pool. Privately positioned within the floor plan, the spacious primary suite offers a relaxing escape, complemented by two walk-in closets and an en-suite bathroom with separate vanities, a soaking tub, and a separate shower. Three additional bedrooms provide comfortable accommodations and flexibility for guests, a home office, or creative pursuits, while a conveniently located half bathroom serves the main living area. Outdoors, the screened private pool becomes a natural extension of the home, offering space to unwind in the sunshine or enjoy a refreshing swim. The covered lanai provides a shaded setting for outdoor dining and entertaining, with a built-in exhaust hood for your BBQ setup and mature landscaping that enhances the inviting surroundings while providing a completely private pool area. An attached two-car garage accessed from the rear preserves the welcoming character of the front elevation while adding everyday convenience. Beyond the home, Lakes of Windermere offers a large community pool and sun deck, tennis, basketball, and volleyball facilities, three playgrounds, and a fishing pier on Lake Sawyer. Pine Loop Park adds a shaded gathering gazebo and an approximately 0.9-mile sidewalk loop for leisurely walks or an afternoon jog. Ideally located close to A-List schools, all four Walt Disney World theme parks and resorts, with shopping, dining, and daily conveniences nearby, this beautifully maintained residence brings together spacious interiors, inviting outdoor living, valuable updates, and a prime Windermere setting. Call me to schedule your private showing now.

7030 Mapperton Drive, Windermere
8168 Boat Hook Loop Unit 302, Windermere
$299,997
2 Beds ⋅ 2 Baths ⋅ Lakeside/Lks/Windermere SubDv. ⋅ 34786 Zip Code
Welcome to this spacious 2-bedroom, 2-bathroom third-floor condo in an elevator building, meaning no noisy above neighbors, in a convenient Windermere location, situated within walking distance from the community clubhouse and its extensive resort-style amenities. Offering an open floor plan, generous living spaces, and a low-maintenance lifestyle, this home is well suited for a full-time residence, second home, or investment property. The open-concept living and dining areas create a comfortable space for everyday living and entertaining, while the spacious kitchen features a breakfast bar, tons of cabinet storage, and large pantry closet. Both bedrooms are generously sized with ample closet space. The primary suite includes a private en-suite bathroom and walk-in closet. An enclosed outdoor living area provides additional space to relax, enjoy your morning coffee, or unwind at the end of the day. The community clubhouse is located just steps away and offers a variety of amenities, including a large swimming pool, fitness center, library, fireplace gathering area, kitchen facilities for entertaining, volleyball court, and playground. Located in Windermere with convenient access to Walt Disney World, shopping, A rated schools, dining, entertainment, and major Central Florida attractions. Disney's Magic Kingdom is approximately 10 minutes away, making this property an attractive option for those seeking a primary residence, vacation home, or investment opportunity in the Orlando area. Schedule your private showing today and discover the convenience and lifestyle this Windermere condo has to offer.

8168 Boat Hook Loop Unit 302, Windermere
7271 Londale Boulevard, Windermere
$562,000
3 Beds ⋅ 2 Baths ⋅ Enclave/Berkshire Park B G H I SubDv. ⋅ 34786 Zip Code
7271 Londale Blvd is a one-story Windermere home with an open layout and a large kitchen island. The kitchen has white cabinetry, stainless steel appliances, and counter space, and it opens to the dining and living areas. Bedrooms have neutral finishes, and the bathrooms have tile surrounds and vanities. A screened patio overlooks the lawn, with mature landscaping around the house. An attached one-car garage and a broad driveway sit at the front. Included 100-Day Home Warranty with buyer activation

7271 Londale Boulevard, Windermere
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