Windermere Homes under $1 million

Windermere Homes under $1 million

Welcome to Windermere, Florida – a picturesque gem nestled in Orange County, just a stone's throw away from the vibrant city of Orlando. Known for its stunning lakes, charming streets, and a strong sense of community, Windermere offers a serene lifestyle that beautifully balances suburban tranquility with urban convenience. With its lush landscapes and scenic waterfront views, this enchanting town is perfect for families, retirees, and everyone in between.

One of the most appealing aspects of Windermere is the accessibility of homes under $1 million. This makes it an ideal destination for first-time homebuyers and those looking to invest in a slice of Florida paradise without breaking the bank. The real estate market here features a variety of options, from contemporary single-family homes to cozy townhouses, all designed to cater to diverse tastes and lifestyles. Many properties boast modern amenities, spacious layouts, and beautiful outdoor spaces, perfect for enjoying the Florida sunshine.

Living in Windermere means you’ll enjoy a tight-knit community with excellent schools, lush parks, and a plethora of recreational activities. The nearby Butler Chain of Lakes offers opportunities for boating, fishing, and kayaking, while the charming downtown area features delightful shops and restaurants that capture the essence of small-town charm.

Whether you’re drawn to Windermere for its natural beauty, community spirit, or affordable housing options, it’s a place where dreams of homeownership can become a reality. Explore the possibilities in this enchanting town and discover your perfect home today!

Newest Windermere Homes under $1 million

14551 Yellow Butterfly Road, Windermere
$784,900
5 Beds ⋅ 4 Baths ⋅ S5160985 MLS
Welcome to this beautifully maintained and thoughtfully updated home, ideally situated along a quiet bend of Yellow Butterfly Road in the desirable Summerport community. Backing to a peaceful natural setting with trees, a scenic walking path, and pond views, this property combines privacy, comfort, and convenience. Step outside and enjoy the fenced backyard, attractive landscaping, young orange and mango trees, and an expansive brick-paver patio—an inviting setting for relaxing, entertaining, or simply enjoying Florida's beautiful weather. Inside, the home features spacious living areas, including a versatile first-floor den that can serve as a home office, study, or flex space. Imagine coming home for the holidays, gathering with loved ones, and enjoying the warm glow of the fireplace at the flick of a switch—a cozy touch that makes this home especially inviting. Upstairs, five generously sized bedrooms are thoughtfully arranged for comfort and privacy. The expansive primary suite features two walk-in closets, while two additional bedrooms share a Jack-and-Jill bathroom with separate vanities. Another bedroom features its own en-suite bathroom, and the oversized fifth bedroom, overlooking the trees and pond, provides endless possibilities as a playroom, game room, or additional living space. Conveniently located near SR 535, Hamlin's shopping and dining destinations, scenic walking trails, and Summerport's community amenities, this home provides easy access to the area's finest shopping, dining, recreation, and everyday conveniences. Keene's Crossing Elementary School is within easy reach via the walking path behind the home. Bridgewater Middle School, Windermere High School, Windermere Preparatory School, Foundation Academy, and other educational options are also nearby. Lovingly cared for by its owners, this home is being presented for sale due to a family relocation out of state. A wonderful opportunity to make this exceptional Summerport property your own! Seller is open to considering flexible buyer credits toward closing costs or a mortgage rate buydown for purchase proposals at or near the asking price.

14551 Yellow Butterfly Road, Windermere
104 E 11th Avenue, Windermere
$862,500
3 Beds ⋅ 2 Baths ⋅ O6455790 MLS
Photos coming soon! Welcome to your new home in the historic, golf-cart-friendly Town of Windermere! Nestled on a 0.29-acre corner lot shaded by mature trees, this charming 1-story block home offers 3 bedrooms, 2 bathrooms, and 1,834 square feet of flexible living space on one of Windermere’s beloved dirt roads. Step inside to find an open-concept floor plan designed for effortless entertaining. The oversized main living room serves as a blank canvas, highlighted by a cozy fireplace that anchors the gathering area. Transition seamlessly into the expansive kitchen—a chef’s dream packed with extensive prep space. The hallway in the center of the house leads to two generous bedrooms and a full guest bathroom, while the rear primary suite serves as a quiet retreat complete with an en-suite bathroom. The entire home is fully wired for AT&T high-speed fiber internet, making remote work a breeze. Your private oasis awaits outside. Enjoy a dedicated 36’ x 40' sports court equipped with a basketball hoop, ping pong table, and pickleball net — the ultimate setup for weekend matches and entertaining. Afterward, unwind on your screened back porch. Experience additional peace of mind with an extensive list of structural and mechanical updates: Water Treatment & Softener System (08/2026, incl. transferable warranty) Well Pump (07/2024) Exterior Paint (01/2023) New Attic Insulation (2023) Electric Water Heater (03/2022) New Electric Panel ( 03/2023) Metal Roof (11/2017) HVAC System (06/2014) Double Pane Windows (2012) ?Living in the heart of Windermere means you are just a short walk or golf-cart ride from boutique shopping, weekly farmers markets, and local dining. Best of all, residents enjoy exclusive access to private neighborhood boat ramps to launch into the pristine Butler Chain of Lakes, as well as nearby tennis courts and waterfront parks. Zoned for top-rated public schools including Windermere Elementary. ?Don't miss this rare opportunity to live the ultimate lake-community lifestyle!

104 E 11th Avenue, Windermere
8133 Enchantment Drive Unit 1307, Windermere
$399,000
4 Beds ⋅ 3 Baths ⋅ O6455333 MLS ⋅ 8133 BLDG.
Welcome to this BEAUTIFULLY UPDATED 4-Bedroom, 2.5-Bath Condo in the GATED Oasis Cove at Lakeside Village community in Windermere! Offering the spacious layout and FEEL OF A TOWNHOME, this two-story residence combines modern updates including NEWER AC (2023), flexible living spaces and the convenience of LOW-MAINTENANCE condo living. A paver driveway leads to the TWO-CAR GARAGE, featuring an attractive CARRIAGE-STYLE GARAGE DOOR, while the welcoming exterior sets the stage for all that's waiting inside. Step through the front door and you'll immediately appreciate the FRESH, CONTEMPORARY LOOK, highlighted by NEWER WOOD-LOOK LAMINATE FLOORING throughout the main living areas. The SPACIOUS OPEN LAYOUT allows the Kitchen, Dining Area and Living Room to flow together beautifully, creating an inviting space for everyday living or entertaining. The Living Room is filled with NATURAL LIGHT and features sliding glass doors that open to a COVERED REAR PATIO and fenced backyard—a lovely spot to enjoy your morning coffee or relax outdoors with a little green space of your own.The UPDATED KITCHEN is both stylish and functional, featuring STONE COUNTERTOPS, an abundance of cabinetry, STAINLESS STEEL APPLIANCES and a classic subway tile backsplash. A BREAKFAST BAR offers additional seating and creates a natural gathering spot for casual meals or conversation. The spacious FIRST-FLOOR PRIMARY SUITE provides a comfortable retreat, complete with an EN SUITE BATH featuring dual sinks and a step-in shower, and includes a LARGE WALK-IN CLOSET. A CONVENIENT HALF BATH on the first floor is perfect for guests and everyday living.Upstairs, a GENEROUS LOFT adds wonderful flexibility and makes an ideal family room, media space, game room or home office. ARCHITECTURAL ARCHWAYS and distinctive cutouts add character, while NEWER LAMINATE FLOORING and a sleek, modern ceiling fan give the space a fresh contemporary feel. Two additional Bedrooms, each with NEWER CARPETING, provide comfortable accommodations for family or guests, and both offer WALK-IN CLOSETS. A full Bath nearby, serves the upstairs Bedrooms, while an additional FLEX SPACE can be used as a FOURTH BEDROOM, office, hobby room or whatever best suits your needs. Enjoy the ease of LOW-MAINTENANCE LIVING in this GATED COMMUNITY, where amenities include a clubhouse, COMMUNITY POOL and playground, as well as exterior and grounds maintenance, cable, internet, trash and water, giving you more time to enjoy your home and the surrounding area. Oasis Cove is conveniently situated near LAKESIDE VILLAGE CENTER, where you'll find Publix, restaurants and everyday services, and for even more shopping and dining, WINTER GARDEN VILLAGE offers a wide variety of popular retailers and eateries. Outdoor enthusiasts can explore the trails and natural beauty of TIBET-BUTLER PRESERVE, enjoy lakeside recreation at R.D. KEENE PARK or spend an afternoon at WEST BEACH PARK. And with WALT DISNEY WORLD, Disney Springs and the many attractions of Central Florida nearby, there's always something fun to enjoy.The home is also zoned for A-Rated schools—BAY LAKE ELEMENTARY, HORIZON WEST MIDDLE and WINDERMERE HIGH SCHOOL. With its MODERN UPDATES, spacious loft, flexible living spaces and GREAT LOCATION, this Oasis Cove condo offers a WONDERFUL OPPORTUNITY to enjoy the best of Windermere living. Welcome Home!

8133 Enchantment Drive Unit 1307, Windermere
8736 Peachtree Park Court, Windermere
$875,000
4 Beds ⋅ 3 Baths ⋅ O6455345 MLS
Welcome to this beautifully updated home in the desirable Windermere area, just minutes from Walt Disney World! Featuring a convenient downstairs bedroom and full bathroom. The main living area showcases a stunning custom fireplace, while the kitchen features high-end Café appliances, including an induction range, and a custom pantry. Additional upgrades include all new hurricane-impact windows, automatic shades throughout, a water softener, and fresh interior and exterior paint. Upstairs, you'll find the spacious primary suite with a custom California Closet, 2 additional bedrooms, a loft with a custom glass half wall. The garage features epoxy flooring and EV charging. Enjoy a fenced backyard with no rear neighbors and beautiful natural surroundings, plus a neighborhood playground. Conveniently located near Disney, shopping, dining, and major roadways, this home offers an incredible combination of upgrades, comfort, and location!

8736 Peachtree Park Court, Windermere
9100 Palm Tree Drive, Windermere
$579,000
3 Beds ⋅ 2 Baths ⋅ O6454929 MLS
Welcome to this inviting 3-bedroom, 2-bathroom pool home, situated on a corner lot with a circular driveway in the established community of Silver Woods. A spacious foyer opens into the living room, flowing seamlessly into the adjoining dining area for easy everyday living and entertaining. The conveniently located kitchen connects to the family room, where wood-look tile and vaulted ceilings create a warm, open gathering space. The split-bedroom floor plan offers privacy for the primary suite, complete with a walk-in closet and attached bathroom. Two additional bedrooms and a full bathroom are located on the opposite side of the home, providing flexibility for guests, a home office, or everyday needs. French doors from the family room open to the patio and in-ground pool, creating a welcoming setting for outdoor dining, weekend gatherings, or simply relaxing in the Florida sunshine. A fenced backyard completes the outdoor space. Recent updates - New Porcelain Tile floor throughout, New Hurricane strength garage door, New cabinetry in garage and laundry room, Custom closets in Primary, Roof 2021, Windows 2020, HVAC 2019. Silver Woods offers low HOA fees and community tennis courts, along with a convenient Windermere location near shopping, dining, and Dr. Phillips’ Restaurant Row. Enjoy access to major roadways and popular Central Florida destinations, including Universal Orlando Resort and Walt Disney World. This home brings together comfortable living, outdoor enjoyment, and everyday convenience!

9100 Palm Tree Drive, Windermere
10628 Reams Road, Windermere
$479,000
4 Beds ⋅ 3 Baths ⋅ O6455169 MLS
Welcome to Windermere Trails! This beautiful 4-bedroom, 2.5-bath, two-story home offers the perfect combination of comfort, style, and convenience in one of Central Florida's most desirable locations. Step inside to discover a spacious, open-concept floor plan designed for both everyday living and entertaining. The kitchen features granite countertops, stainless steel appliances, ample cabinetry, and a seamless flow into the living and dining areas. Wood flooring enhances the main living spaces, while generously sized bedrooms provide plenty of room to unwind. Enjoy the convenience of an attached two-car garage, interior laundry, and a private outdoor patio perfect for relaxing after a long day. Ideally located just minutes from Walt Disney World, Disney Springs, shopping, dining, and entertainment, with convenient access to major roadways and everything the growing Horizon West area has to offer. This home delivers the space, location, and lifestyle you've been looking for. Schedule your private showing today!

10628 Reams Road, Windermere
7129 Thicket Branch Alley, Windermere
$450,000
3 Beds ⋅ 3 Baths ⋅ O6455110 MLS ⋅ 7129 BLDG.
A kitchen that makes you stop scrolling. A Windermere address that makes you want to stay. This beautifully upgraded 3-bedroom, 2.5-bath townhome in Ashlin Park offers 1,588 square feet of inviting living space, fresh paint, and distinctive contemporary finishes. The centerpiece is the kitchen: brand-new countertops with a dramatic waterfall edge, decorative wood-slat accents, two-tone cabinetry, stainless steel appliances, and sleek architectural lighting. An open layout connects the kitchen, dining, and living areas—perfect for hosting friends or enjoying a quiet evening at home. Wood-look flooring and stylish bathroom finishes carry the contemporary feel beyond the kitchen. Upstairs, the primary bedroom offers a comfortable retreat, with two additional bedrooms providing room for guests or a home office. A welcoming front porch and two-car garage complete the home. Enjoy Ashlin Park’s community pool, playground, and sidewalks, with shopping, dining, and Disney nearby. Schedule your showing and see what makes this home stand out.

7129 Thicket Branch Alley, Windermere
6620 Sawyer Shores Lane, Windermere
$930,000
4 Beds ⋅ 4 Baths ⋅ O6452089 MLS
Welcome to a rare opportunity to enjoy waterfront living in Windermere! Enjoy canal-front living with access to Lake Sawyer and Little Lake Sawyer from this 4 bedrooms, 3.5 bath Windermere home on over half an acre. Mature trees and a wooded waterway create an inviting backdrop for this home's updated interiors and flexible layout. Inside, welcoming details include crown, decorative wall treatments, and built-in living room shelving. The updated kitchen features white cabinetry, stone countertops, a patterned tile backsplash, under cabinet lighting, stainless steel appliances, and a double-oven range. A generous dining room provides plenty of space for gatherings. Two owner's suites - one upstairs and one downstairs - offer flexibility for guests or multi-generational living. Updated bathrooms feature distinctive tilework and double-sink vanities. Upstairs, a spacious air-conditioned sunroom overlooking the backyard adds versatile living space for relaxing, hobbies, or a home gym. French doors connect the living and dining areas to the downstairs screened porch, while a covered patio provides another spot for outdoor entertaining. The spacious fenced backyard features a swim spa with an adjoining deck, plus a private dock and boat ramp for enjoying the lakes. Major updates include a roof replacement and exterior paint in 2020, upstairs AC and water heater in 2023, an irrigation system installation and asphalt driveway expansion in 2024, a renovated primary shower in 2025, and downstairs AC in 2026. An attached garage completes this property.

6620 Sawyer Shores Lane, Windermere
13555 Gorgona Isle Drive, Windermere
$899,000
6 Beds ⋅ 4 Baths ⋅ O6450150 MLS
Virtually Staged. Welcome to Windermere Isle, where spacious living, thoughtful design, and an exceptional location come together in this impressive 6-bedroom, 4-bathroom home offering 4,199 square feet of living space, plus a spacious upstairs loft! Designed with both everyday comfort and entertaining in mind, this beautiful two-story residence features an open and versatile floor plan with two bedrooms conveniently located on the first floor. Beautiful wood flooring leads to the second floor, while wood-look tile flooring flows throughout the main living areas, creating a warm and cohesive feel. An abundance of windows fills the home with natural light. The spacious family room opens seamlessly to the beautifully appointed kitchen, featuring quartz countertops, rich dark cabinetry, stainless steel appliances, a gas cooktop, built-in double ovens, a stylish tile backsplash, and an oversized center island with seating, perfect for casual meals and gathering with friends and family. A generous dining area provides additional space for everyday meals, while a separate formal dining room offers an inviting setting for special occasions. Additional highlights include an expansive walk-in pantry and a conveniently located built-in workspace with abundant cabinetry and countertop space. The first floor also offers two bedrooms, providing flexibility for guests, a home office, or multigenerational living. Upstairs, the spacious loft creates an impressive second living area, ideal for a media room, game room, or comfortable gathering space. Four additional bedrooms provide plenty of room for everyone, and quartz countertops in all bathrooms add a cohesive finishing touch. Step outside through the sliding glass doors to a generously sized covered patio overlooking the fenced backyard, offering a wonderful setting for outdoor dining, entertaining, or simply enjoying the Florida weather. As an added bonus, enjoy views of Disney fireworks from your own backyard! Additional features include a two-car garage with overhead storage racks, two air-conditioning systems, and solar panels that will be paid off by the seller at closing, providing an appealing energy-efficient benefit. Residents of Windermere Isle enjoy a resort-style community swimming pool with poolside cabana and playground, while HOA fees include lawn care, cable TV, and internet. Conveniently located near Walt Disney World, world-class shopping, dining, and major roadways. With its generous living spaces, versatile floor plan, and desirable community amenities, this exceptional home offers an outstanding opportunity to enjoy the Windermere lifestyle!

13555 Gorgona Isle Drive, Windermere
8214 Serenity Spring Drive Unit 2405, Windermere
$350,000
3 Beds ⋅ 3 Baths ⋅ O6453473 MLS ⋅ 2405 BLDG.
Live about as close to the magic as you can get without a Disney address. This home in gated Oasis Cove sits just 3 minutes from Disney property, so park days, dinner reservations, and fireworks nights are a quick drive instead of a trip. The 3 bed, 2.5 bath layout offers 1,512 sq ft and a 1-car garage, with upgraded flooring on the stairs and throughout the upper level. The HOA covers the roof, lawn care, and water, so electricity is your only utility bill, and the HVAC was replaced in 2024. Spend your free time at the resort-style pool and community amenities, or at the parks down the road, instead of maintaining a home. It works equally well for full-time residents and seasonal owners. Zoned for A-rated schools from elementary through high school. Buyer to verify school assignment, HOA coverage.

8214 Serenity Spring Drive Unit 2405, Windermere
6206 Golden Dewdrop Trail, Windermere
$580,000
3 Beds ⋅ 3 Baths ⋅ O6451210 MLS
Welcome to 6206 Golden Dewdrop Trail in Windermere Landings — an opportunity to live in Windermere, one of Central Florida's most exclusive and sought-after addresses. Set among the Butler Chain of Lakes, Windermere is known for its privacy, tree-canopied streets, and lake lifestyle, yet it's just minutes to Restaurant Row, Winter Garden, and world-class attractions. This 3-bedroom, 2.5-bath, two-story home offers 1,984 square feet with an open main level and ceramic tile throughout the first floor: living and dining areas flow into a kitchen with granite counters, wood cabinetry, stainless appliances, and an island with seating. There's also a downstairs nook and a powder room on the first floor. Plantation shutters on all the windows and upgraded light fixtures run throughout the home. Upstairs, the primary suite has wood flooring and a double-vanity bath; two more bedrooms, a full bath, laundry, and a loft nook complete the level. Out back, a covered porch and paver patio overlook the privacy-fenced yard — ideal for enjoying Florida evenings at home. Windermere Landings offers a pool, clubhouse, and playground, all within this coveted Windermere location.

6206 Golden Dewdrop Trail, Windermere
8325 Vivaro Isle Way, Windermere
$799,900
4 Beds ⋅ 3 Baths ⋅ O6452086 MLS
Virtually Staged. **POND VIEWS & DISNEY FIREWORKS!** Prepare to be impressed by this beautifully appointed 4-bedroom, 3-bath home in sought-after Windermere Isle, offering an inviting blend of stylish living, thoughtful upgrades, and a picturesque pond backdrop with a fountain and conservation views. Designed for both everyday comfort and entertaining, the open floor plan is enhanced by a decorative coffered ceiling in the dining room and a custom built-in entertainment feature that adds architectural interest and a polished focal point to the family room. The kitchen is equally impressive with granite countertops, tile backsplash, stainless steel appliances, abundant cabinetry, and a large center island, complemented by an adjacent informal dining area for casual meals. Everyday functionality is thoughtfully incorporated with a built-in drop zone just inside the garage entry, conveniently positioned near the walk-in pantry and kitchen. A first-floor bedroom with a full bath nearby provides wonderful flexibility for guests, while a creative nook beneath the stairs features a built-in desk, storage, and chalkboard wall, offering a fun space for homework, crafts, or play. Upstairs, **laminate flooring** extends throughout the stairs and entire second floor, where a spacious loft provides another inviting gathering space. The primary suite offers a relaxing retreat with two large walk-in closets and a beautifully appointed bath featuring dual vanities, a freestanding soaking tub, and glass-enclosed shower. The outdoor setting truly sets this home apart. A screened lanai with summer kitchen overlooks the fenced backyard and tranquil pond with fountain, creating the perfect backdrop for dining, entertaining, or simply unwinding while enjoying Disney fireworks in the distance. The home is also equipped with solar panels, while the two-car garage features an EV charger and overhead storage. Upgraded landscaping enhances the home’s curb appeal. Residents of Windermere Isle enjoy a resort-style community swimming pool with poolside cabana and playground, while HOA fees include lawn care, cable TV, and internet. Conveniently located near Walt Disney World, world-class shopping, dining, and major roadways. With its generous living spaces, versatile floor plan, beautiful pond setting, and desirable community amenities, this exceptional home offers an outstanding opportunity to enjoy the Windermere lifestyle!

8325 Vivaro Isle Way, Windermere
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