Location: Windermere , 34786
Do Not Show Listings
13858 CAYWOOD POND DR, WINDERMERE, FL 34786
$963,00055 Days on yellowkey MLS ID: O6382987
2 Days Off yellowkey (back on 4/5/2026)
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3070 Built: 2004Monthly Fee: $130 Tax: $12,050 (2025)Community: Summerport Ph 1Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$12,050
Elementary School: Keene Crossing Elementary
High School: Windermere High School
Tax Year: 2025
Middle School: Bridgewater Middle
Remarks: Under contract-accepting backup offers. JUST REMODELED! Stunning lakefront pool home located in the heart of Windermere, offering 5 bedrooms, 4 full bathrooms, and nearly 3,100 square feet of beautifully updated living space. Perfectly positioned between downtown Windermere and Winter Garden Village, this exceptional property is nestled within the highly desirable Summerport community and features pristine waterfront views. This is more than a home-it's a lifestyle. From the moment you arrive, the home’s curb appeal impresses with a beautiful stone façade, charming arbor detail, spacious covered front porch, and a 3-car split garage. Inside, you are welcomed by a dramatic 20-foot ceiling in the formal living room, highlighted by elegant arched openings, a sweeping staircase, and a curved balcony overlooking the space below. Fresh updates throughout create a bright, modern feel, making this home truly move-in ready. Major improvements include a recently updated roof in last 6 years, brand-new AC system, and new water heater, new pool pump, new spa gas heater — offering comfort and peace of mind for years to come. Step outside to your private screened-in pool oasis. Cool off in the sparkling pool while enjoying serene lake views, mature landscaping, and added privacy from lush greenery — the perfect setting for relaxing or entertaining. Residents of Summerport enjoy resort-style amenities including a community pool, fitness center, basketball and tennis courts — all just minutes from shopping, dining, and entertainment at Winter Garden Village, and zoned for top-rated Windermere schools. Experience luxury lakefront living with privacy, elegance, and timeless charm — all in one of Central Florida’s most sought-after communities. Information deemed reliable but not guaranteed.
Listing is courtesy of: SPRING REALTY ONE LLC (407-340-1754)
Listing Agent: Chun Cai (951-699-4983)
12132 MONTALCINO CIR, WINDERMERE, FL 34786
$3,950,000166 Days on yellowkey MLS ID: O6319854
Bed: 6 Bath: 7.0 Gar: 3 Liv Area Sq Ft: 5709 Built: 2016Monthly Fee: $242 Tax: $38,798 (2024)Community: Casa Del Lago RepSingle Family
Taxes:$38,798
Elementary School: Sunset Park Elem
Tax Year: 2024
Middle School: Horizon West Middle School
Remarks: Experience the essence of luxury lakefront living in this stunning contemporary Mediterranean estate, ideally positioned on Lake Burden within the exclusive gated community of Casa Del Lago in Windermere. This elegant two-story residence combines refined design, functionality, and breathtaking panoramic lake views throughout. The gourmet kitchen features custom dark cabinetry, quartz countertops, a designer mosaic backsplash, pendant lighting, and top-of-the-line stainless-steel appliances. The primary suite is a serene retreat showcasing peaceful lake views, a spa-inspired bathroom with a freestanding soaking tub, dual vanities, and a custom-designed walk-in closet. This remarkable home also includes a fully equipped theater room, a complete gym setup, multiple TVs, and select designer furniture pieces in the dining room, living room, and office, along with all chandeliers and lighting fixtures. Outdoors, enjoy a resort-style pool, spacious travertine patio, and a private dock with lifts for both a Yamaha boat and Jet Ski, which are included in the sale for your convenience. With its three-car garage, lush landscaping, and proximity to fine dining, golf, and top-rated schools, this residence exemplifies modern sophistication and lakefront elegance in Windermere.
Listing is courtesy of: BELLA VIEW REALTY LLC (407-616-7653)
Listing Agent: Caroline Perotti (407-460-9019)
11455 CLAYMONT CIR, WINDERMERE, FL 34786
$1,249,00016 Days on yellowkey MLS ID: O6396381
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2262 Built: 2003Monthly Fee: $298 Tax: $7,673 (2025)Community: Keenes PointeSingle Family
Taxes:$7,673
Elementary School: Windermere Elem
Remarks: Better-Than-New Fully Renovated Pool Home in 24-hour gated/attended Keene's Pointe. Home to The Golden Bear Club an 18-hole golf course designed by Jack Nicklaus featuring golf, tennis, fitness, dining and swimming. Welcome to your dream home—completely renovated and truly move-in ready! This stunning residence offers the perfect blend of modern upgrades, thoughtful design, and luxurious indoor-outdoor living. Step inside to discover a spacious, light-filled layout featuring three bedrooms, three full bathrooms, formal dining room, and a dedicated office, ideal for working from home or creating a private retreat. A formal dining room with arched window greets you at the entrance, while the heart of the home opens into an expansive great room with an open-concept floor plan, seamlessly connecting the living, dining, and kitchen areas—perfect for entertaining. The low maintenance wood-look tile carries throughout the home.The beautifully updated kitchen boasts a large island that seats 6 comfortably and provides additional storage. White and oak shaker cabinets, Verona quartz on the counters and backsplash, and new stainless steel appliances, create a warm and inviting atmosphere for gatherings both large and small.The primary suite offers two custom closets and bathroom with dual vanities, free-standing tub and zero entry shower. On each side of the kitchen are the two additional bedrooms with full baths to service each offering custom tile detailing and decorative free-standing vanities. From the great room through the triple-panel sliding door you enter the patio overlooking your own private oasis with an oversized pool and spa, recently resurfaced and enhanced with a new pool motor and heater—perfect for year-round relaxation and entertaining. Throughout this home you will find quality features such as designer lighting, crown moldings, and coffered and tray ceilings. Additional highlights include: 3-car garage with ample storage space, tankless gas water heater for energy efficiency and endless hot water, new roof (2022), professionally designed landscaping and much more. Every detail has been thoughtfully updated, offering the feel of new construction without the wait. Located in close proximity to shopping, dining, major tourist attractions, expressways and top-rated public and private schools - space, style and upgrades in every corner, this home truly has it all!
Listing is courtesy of: SOUTHERN REALTY GROUP LLC (407-217-6480)
Listing Agent: Teresa Stewart (407-493-3057)
1002 DOWN RESERVE CT, WINDERMERE, FL 34786
$6,490,00058 Days on yellowkey MLS ID: O6383597
0 Days Off yellowkey (back on 4/4/2026)
Bed: 6 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 6706 Built: 2021Monthly Fee: $433 Tax: $61,838 (2024)Community: Rosser Reserve RepSingle Family
Taxes:$61,838
High School: Olympia High
Middle School: Chain of Lakes Middle
Remarks: UNDER CONTRACT ACCEPTING BACKUP OFFERS! Luxury, architectural elegance, and an unparalleled lakefront lifestyle on the Butler Chain of Lakes in Windermere. Set on a sprawling lot of over one acre, this extraordinary waterfront estate offers direct access to the prestigious Butler Chain of Lakes — a rare interconnected system of 12 private lakes, providing one of the most exclusive boating lifestyles in Central Florida. From the moment you arrive, the home captivates with its contemporary architecture, expansive paver driveway, and striking façade. Clean lines, refined finishes, and manicured landscaping create an unforgettable first impression. Inside, soaring ceilings, exposed wood beams, and designer lighting enhance the open-concept layout. Oversized sliding glass doors frame breathtaking panoramic lake views while creating a seamless indoor-outdoor flow filled with natural light. The gourmet kitchen serves as the heart of the home, featuring an oversized quartz island, custom cabinetry, and premium stainless steel appliances — perfectly designed for both intimate gatherings and grand-scale entertaining. With 6 spacious bedrooms, 5 full bathrooms, and 1 powder room, the residence offers comfort and privacy for family and guests. Beyond the main living areas, this home delivers an exceptional lifestyle experience with a private gym, dedicated cinema room, game room, and playroom — thoughtfully designed for wellness, entertainment, and family enjoyment. Step outside into your private lakeside retreat. The resort-style pool with integrated spa is complemented by sleek glass railings that preserve unobstructed water views. The covered outdoor living area is a masterpiece, featuring a wood-paneled ceiling, oversized ceiling fan, stone fireplace, mounted TV, and a fully equipped summer kitchen with professional-grade stainless steel grill and hood — ideal for year-round entertaining. The private covered dock accommodates boats and jet skis and provides direct access to all 12 lakes of the Butler Chain, making this property a true paradise for boating enthusiasts. Additional features include: Whole-house water filtration system High-capacity generator capable of powering the entire residence Located within an exclusive gated community with meticulously maintained infrastructure Offering privacy, security, expansive outdoor space, and one of Windermere’s most coveted lakefront settings, this is more than a residence — it is a lifestyle defined by elegance, recreation, and exclusivity. Schedule your private showing and experience lakefront living at its finest.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Jennifer Olmeda (407-547-9242)
13013 OVERSTREET RD, WINDERMERE, FL 34786
$679,99453 Days on yellowkey MLS ID: O6380917
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2053 Built: 2009Monthly Fee: $82 Tax: $3,146 (2024)Community: Lakes/WindermereSingle Family
Taxes:$3,146
Remarks: Welcome to 13013 Overstreet Rd — a beautifully upgraded 4-bedroom, 2.5-bath home located in one of Windermere’s most desirable and sought-after communities. This property combines modern living, elegant design, and the true Florida lifestyle you’ve been searching for. Step inside to an open, bright floor plan featuring gorgeous wood floors, a spacious living area, and a modern kitchen with sleek cabinetry, stainless steel appliances, island, and plenty of storage — perfect for everyday cooking or entertaining friends and family. The primary suite includes a luxurious bathroom with his-and-her sinks and an upgraded California closet with premium built-ins for maximum organization. Enjoy Florida weather year-round in the screened-in patio with a retractable electric screen, extending your living space and providing the perfect spot for morning coffee or evening relaxation. The large, fully fenced backyard features extended brick pavers, offering plenty of room for gatherings, grilling, pets, or future customization. Additional features include a front balcony, a 2-car garage, and an oversized driveway with great curb appeal. This home sits in a prime Windermere location surrounded by some of the best amenities in Central Florida. Just minutes away you’ll find top-rated Windermere schools, scenic lakes, nature trails, Bay Hill, The Butler Chain of Lakes, playgrounds, and community parks. Nearby you’ll enjoy endless shopping, popular restaurants, cafés, breweries, local markets, and everyday conveniences. You’re also close to the Winter Garden Village, Downtown Windermere, major highways, theme parks, and world-class entertainment. The community itself offers resort-style amenities including a sparkling community pool and clubhouse — perfect for relaxing weekends and social gatherings. If you’re looking for a move-in-ready home with modern finishes, incredible outdoor space, and a location that simply can’t be beat, this is the one. Homes like this in Windermere don’t last long — schedule your private showing today! *** A/C and Water Heater replaced in 2024. Roof replaced in 2025. Exterior of home repainted in 2022 ***
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Omar Andreasen (407-883-2989)
4 CHASE RD, WINDERMERE, FL 34786
$900,00059 Days on yellowkey MLS ID: O6384257
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2386 Built: 1971 Tax: $7,637 (2024)Community: Windermere TownSingle Family
Taxes:$7,637
Elementary School: None
High School: None
Middle School: None
Remarks: FULLY RENOVATED DREAM HOME. This home is located right in the heart of the Town of Windermere. Welcome to 4 Chase Rd, Windermere - a refined expression of luxury living where elevated design, privacy, and lifestyle converge. Set within one of Windermere’s most desirable areas, this exceptional residence delivers a seamless blend of sophistication and comfort. From its striking curb appeal to its thoughtfully curated interior spaces, every detail has been designed to create an atmosphere of understated elegance. Inside, expansive living spaces unfold beneath soaring ceilings and abundant natural light, creating a sense of openness while maintaining warmth and intimacy. The chef’s kitchen anchors the home, featuring premium finishes, generous workspace, and effortless flow into the main living and entertaining areas - ideal for both everyday living and elevated gatherings. The primary suite serves as a private sanctuary, offering a tranquil escape with a spa-inspired bath and spacious walk-in storage. Secondary bedrooms provide flexibility for guests, executive office space, or multigenerational living while maintaining the home’s refined aesthetic. Outdoors, the property transforms into a resort-style retreat designed for entertaining and relaxation. Thoughtfully designed outdoor living spaces create the perfect setting for evening gatherings, weekend hosting, or quiet moments of escape. Positioned in the heart of Windermere, the home offers convenient access to top-rated schools, amenities, dining, shopping, and major thoroughfares while preserving the exclusivity and lifestyle the area is known for.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Matthew Hughes (407-619-4717)
11835 GOLD CREEK TRL, WINDERMERE, FL 34786
$900,00067 Days on yellowkey MLS ID: O6382068
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3119 Built: 2012Monthly Fee: $75 Tax: $9,395 (2024)Community: Windermere Trls Ph 1ASingle Family
Taxes:$9,395
Remarks: Windermere Trails Award Winning Model - Voted #1 Model by HBA 2013 It's surrounded by The Butler Chain of Lakes, with fabulous shopping and dining just minutes away. These are just a few of the celebrated qualities you'll love about Windermere Trails. Located in Windermere, FL, Windermere Trails is a community of new, incredibly energy-efficient homes, ranging 2,260 - 4,400 sq. ft. just south-east of downtown Orlando and is only a short drive to the SR 429 giving you access to the Florida Turnpike, SR 408 and I4; so you're close to all of Orlando's most popular area attractions. If golfing, boating, shopping and great schools are on your list of must-haves, you'll absolutely cherish living at Windermere Trails with Butler Chain of Lakes, several area golf courses and excellent schools, such as Windermere Prep nearby. Every home we build showcases our commitment to providing incredibly energy-efficient homes that let you spend your money on better things than utility bills. After all, we believe in building new homes and communities the way they can, and should be, built. That's why every Meritage home at Windermere Trails is built standard with the following energy- and money-saving features: - Spray-Foam Insulation - ENERGY STAR Appliances - ENERGY STAR Programmable Thermostat - Low-E2 Double pane/tinted Vinyl Windows - Variable SEER 15 HVAC - CFL Lighting and Fixtures - Weather-Sensing Irrigation - Water-Efficient Fixtures - Dual-Flush Toilets - Low VOC Carpets, Paints and Finishes
Listing is courtesy of: BB GROUP REALTY CORP (407-624-7625)
Listing Agent: Flavio Vieira De Melo (407-470-5008)
13421 BONICA WAY, WINDERMERE, FL 34786
$1,369,99931 Days on yellowkey MLS ID: O6392381
Bed: 6 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4869 Built: 2005Monthly Fee: $317 Tax: $19,939 (2025)Community: Tildens Grove Ph 02Single Family
Taxes:$19,939
Remarks: Gorgeous East facing custom estate on a .63-acre lot in the highly sought-after 24-hour guard-gated community of Tildens Grove in Windermere. This elegant home offers 6 bedrooms, 4.5 baths, and an open layout perfect for entertaining, all located near top-rated schools, the Butler Chain of Lakes, Winter Garden Village, major highways, and Walt Disney World. Kitchen has two-tone cabinetry, granite countertops, an oversized island, gas cooktop, double ovens, walk-in pantry, and brick wine cellar with cast iron doors. The kitchen opens to a spacious family room with custom built-ins, gas fireplace, and French doors leading to the lanai. Formal living and dining rooms showcase tray and coffered ceilings, with travertine flooring and crown molding throughout the main areas. Fenced yard. The primary suite features a sitting area, bay windows, French doors to the pool, dual walk-in closets, and a bath with soaking tub, dual vanities, and walk-in shower. A connected flex room can serve as an office, nursery, or additional bedroom. The split floor plan offers privacy, while upstairs includes a bonus room, bedroom, full bath. Additional highlights include a dedicated office, oversized 3-car garage, and numerous updates such as new A/C, water softener, gas stove, washer/dryer, electrical upgrades, and fresh exterior paint. Tildens Grove is an exclusive community of 140 homes offering tennis courts, playground, basketball court, and soccer field, with a neighborhood park just steps away.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Aparajita Leekha (352-562-3731)
8375 BOWDEN WAY, WINDERMERE, FL 34786
$1,369,000175 Days on yellowkey MLS ID: S5137385
1 Days Off yellowkey (back on 4/4/2026)
REDUCED by $1,000 (0.1%) on 03/31/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3809 Built: 1999Monthly Fee: $283 Tax: $9,709 (2025)Community: Keenes Pointe Unit 1Single Family
Taxes:$9,709
Remarks: The kitchen has been recently upgraded with brand-new white quartz (Calacatta Belardo) countertops and backsplash, creating a bright, modern, and spacious feel. This charming four-bedroom, three-and-a-half-bath home in the highly sought-after Keene’s Pointe community perfectly combines elegance, comfort, and character. Designed with a timeless French-inspired décor, every space feels warm, inviting, and beautifully curated. The highlight of this home is its backyard oasis — a peaceful retreat overlooking the sparkling pool and tranquil pond views, creating the perfect setting for relaxation and entertainment. A nice added air-conditioned covered patio area allows you to enjoy the outdoors year-round, even on the warmest Florida days. Inside, you’ll find beautifully appointed living spaces, elegant finishes, and a floor plan designed for both comfort and functionality — ideal for families or those who love to host. Recent Updates Include: A/C Unit: 2025,A/C Unit: 2016,Roof: 2018,Pool Heater: 2020, Irrigation Well: 2022 Water Heater: 1999 Life in Keene’s Pointe is truly exceptional. Residents enjoy a gated, golf-course lifestyle surrounded by nature, scenic lakes, and the renowned Golden Bear Club, designed by Jack Nicklaus. This exclusive Windermere community offers an active, social, and family-friendly atmosphere unlike anywhere else. Don’t miss the opportunity to make this stunning French-style home your own — a perfect blend of elegance, comfort, and Florida charm.
Listing is courtesy of: B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE (407-217-7573)
Listing Agent: Oscar Rodriguez (321-297-7264)
3138 SEIGNEURY DR, WINDERMERE, FL 34786
$1,350,00041 Days on yellowkey MLS ID: O6387397
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3831 Built: 1997Monthly Fee: $250 Tax: $11,794 (2024)Community: Harbor IsleSingle Family
Taxes:$11,794
Elementary School: Thornebrooke Elem
Middle School: Gotha Middle
Remarks: Under contract-accepting backup offers. Timeless style and classic design unfold behind the gates of Harbor Isle, one of Windermere’s most sought-after communities. This custom-built estate residence offers captivating views of Lake Down on the pristine Butler Chain of Lakes. Featuring all living areas on the first floor except for a bonus room upstairs, this thoughtfully crafted home offers separate formal and living spaces and a private den. The generously-sized primary retreat has a gas fireplace and large bath including oversized shower. Clerestory windows bathe the home in an abundance of natural sunlight. Three secondary bedrooms on the first floor include a guest room with pool bath and a pocket door feature to create a private suite. The additional bedrooms on the first floor are joined by a jack-and-jill-style bathroom. A multi-use space on the second floor is mammoth in size and is a perfect retreat for working from home, game room, or playroom. With an adjacent full bath, the space is large enough to be converted into two additional bedrooms. The screen enclosed pool and spa with patio offers a tranquil escape with lake views in the distance. Harbor Isle is an exclusive gated community of just 31 home sites, perched along the shores of Lake Down on The Butler Chain, and on the east side of Windermere offering easy access to downtown Orlando, theme parks, Restaurant Row, and the best shopping options in Central Florida.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Rob Rahter (407-497-4526)
14217 BRIDGEWATER CROSSINGS BLVD, WINDERMERE, FL 34786
$600,00017 Days on yellowkey MLS ID: O6396155
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2419 Built: 2006Monthly Fee: $131 Tax: $8,205 (2026)Community: SummerportSingle Family
Taxes:$8,205
Tax Year: 2026
Remarks: Don't miss out on this 4 bedroom 3 bathrooms in the tranquil Summerport community in Windermere. The first floor consists of the Kitchen, dining, family room, living room, the Master bedroom and the 3 other bedrooms and the guest bathroom. The second floor consists of the large loft, closets and a full bathroom. Don’t miss your chance to experience exceptional living very close to Keenes Crossing Elementary, Bridgewater Middle and Windermere high
Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-585-0500)
Listing Agent: Azim Manji (407-342-3548)
8533 GREENBANK BLVD, WINDERMERE, FL 34786
$550,000180 Days on yellowkey MLS ID: O6354672
0 Days Off yellowkey (back on 4/3/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2551 Built: 2004Monthly Fee: $176 Tax: $3,300 (2024)Community: Lakes/Windermere-PeachtreeSingle Family
Taxes:$3,300
Remarks: Roof is 2022, A beautiful Home in a wonderful Gated Community in Windermere. Home sits on a big lot that extends all the way to the high tree, and it has fruit trees, avocado, and mango. Home is very spacious with Master downstairs, one owner, the upper floor was not even being used by seller. Come see this beauty, priced to sell. Motivated Seller, please bring your offers.
Listing is courtesy of: CENTURY 21 CARIOTI (407-354-0074)
Listing Agent: Faneeza Mohamed (321-438-7843)
9323 GLADYS GARDEN CT, WINDERMERE, FL 34786
$12,500,00066 Days on yellowkey MLS ID: O6381880
REDUCED by $1,495,000 (10.7%) on 04/03/2026
Bed: 6 Bath: 8.0 Gar: 4 Liv Area Sq Ft: 9770 Built: 2026Monthly Fee: $1,099 Tax: $21,279 (2025)Community: IsleworthSingle Family
Taxes:$21,279
Remarks: Brand new construction and fully furnished! Architecturally refined and intentionally designed by Ashley Martin Home, this custom estate is a masterclass in proportion, craftsmanship, and quiet luxury. European-inspired stonework, dramatic gabled rooflines, and a custom metal arched front door set a tone of understated elegance from the moment of arrival. Concrete tile roofing, four-car garage plus golf cart garage, and a friends-and-family entry with covered parking. Inside, discover Sierra Pacific casement windows with stained interior mullions flood the home with natural light, highlighting warm beams, wide-plank floors, and curated details. Lutron lighting, Sonos audio, and powered draperies enhance modern comfort without compromising design. The formal dining room features a stained white oak arched opening, classic dentil molding, and built-in wine display. The living room is anchored by a gas Isokern fireplace with precast surround, custom built-ins, stained beams, and sculptural custom one off lighting, while an interior glass breezeway subtly defines the transition to the private primary wing. The primary suite offers a serene retreat with custom arch detailing, a nickel joint ceiling, and stained beams. The spa-inspired bath includes a marble soaking tub and a dramatic solid limestone staircase leading to a hidden upper-level flex space, ideal for an office or gym, complete with beverage refrigeration and powered Roman shade. The boutique-style closet features dual islands and an integrated wash tower. At the heart of the home, the chef’s kitchen stuns with soaring 18-foot ceilings, exposed beams, a curved reeded island, and custom Urban Electric pendants designed specifically for the residence. Sub-Zero refrigeration, freezer, and wine column, a 60-inch Wolf range, dual integrated dishwashers, and a fully equipped back kitchen ensure effortless entertaining. Indoor and outdoor living connect seamlessly to a private courtyard-style retreat featuring a resort-inspired pool with copper scupper water features, a summer kitchen with Wolf grill, powered screens, and multiple lounging areas designed for year-round enjoyment. Additional highlights include four upstairs en-suite bedrooms, including a secondary primary suite, an upstairs laundry with linen towers and folding station, a third-level bonus floor with theater, bar, powder bath, and storage, elevator-ready construction, and an advanced security system with AI-enabled cameras and window vibration sensors. Designed with architectural intention, this home pairs refined craftsmanship with warmth, creating spaces that feel both elevated and deeply livable.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Steve Healy (407-230-1441)
8256 MARITIME FLAG ST #103| 1710, WINDERMERE, FL 34786
$338,49027 Days on yellowkey MLS ID: O6393278
0 Days Off yellowkey (back on 4/1/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1442 Built: 2009 Tax: $1,540 (2024)Community: Lakeside/Lks/Windermere Ph 17Condo
Taxes:$1,540
Remarks: Under contract-accepting backup offers. Rare opportunity to own a first-floor 3-bedroom, 2-bath condo in the only condo community located in highly sought-after Windermere. This corner-unit offers added privacy and a unique “home-like” feel, featuring a spacious screened terrace with an open and peaceful setting — no direct rear neighbors, allowing you to enjoy a more private outdoor space. The interior showcases ceramic tile flooring throughout, a modern kitchen with granite countertops, and a well-maintained condition with no pending repairs. Recent upgrades include a new water heater and an updated interior A/C unit for added efficiency and comfort. The unit has plenty of storage, multiple linen closets, and a spacious pantry The community offers resort-style amenities, including a clubhouse, fitness center, swimming pool, and beach volleyball court, creating a lifestyle that blends convenience and leisure. Additional features include two assigned parking spaces, an electronic door lock, pre-wired alarm system, ceiling fans throughout, and window treatments in all areas. Ideally located near top-rated schools, shopping, dining, and major roadways, this property is perfect for both homeowners and investors seeking value in one of Central Florida’s most desirable areas.
Listing is courtesy of: METROPOLITAN R.E SOLUTIONS INC (407-953-6501)
Listing Agent: Alejandra Silva (407-929-7308)
5130 SUN PALM DR, WINDERMERE, FL 34786
$525,00018 Days on yellowkey MLS ID: O6390875
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1723 Built: 1987Monthly Fee: $30 Tax: $8,032 (2025)Community: Silver Woods Ph 04Single Family
Taxes:$8,032
Remarks: Welcome to 5130 Sun Palm Drive, located in the heart of WINDERMERE! This beautifully maintained 3-bedroom, 2-bath home offers 1,723 sqft of living space on a spacious ¼-acre FULLY FENCED lot — perfect for outdoor enjoyment and privacy. Recent upgrades include a new ROOF (2022) and a new AC SYSTEM (2020). ALL FLOORING HAS BEEN UPDATED. The carpet was removed and replaced with Mohawk Pergo luxury vinyl plank. The original tile was replaced with fresh ceramic tile throughout the rest of the house—NO MORE POPCORN CEILING, all was removed, and now it has a beautiful finished ceiling. A brand NEW SLIDING GLASS DOOR opens to the NEW PATIO DECK recently installed. Ideal for indoor-outdoor living. Just minutes from the famous Sand Lake Restaurant Row, conveniently located near the distinguished Bay Hill Golf Community, and backing up to the exclusive Isleworth Court private community. Zoned for top-rated schools, and ideally situated just 20 MINUTES from Walt Disney World and 10 minutes from Universal Studios — this location truly offers the best of Central Florida living!
Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)
Listing Agent: Elle Walters (407-431-4600)
6712 THORNHILL CIR, WINDERMERE, FL 34786
$680,000189 Days on yellowkey MLS ID: O6351284
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2976 Built: 2002Monthly Fee: $80 Tax: $4,096 (2024)Community: Lakes Windermere Ph 01 49 108Single Family
Taxes:$4,096
Remarks: With timeless curb appeal and a front porch built for slow mornings, this Windermere home blends classic charm with the upgrades that make everyday life easier. Step inside and the ceilings rise, sunlight floods through, and hardwood floors (2021) lead you through open living and dining spaces that flow seamlessly into a remodeled kitchen with quartz countertops, updated cabinetry, and dual pantries that actually hold it all. The primary suite sits privately on the main floor with with a large walk in closet, and ensuite, while three additional bedrooms offer room to spread out — perfect for guests, a home office, or both. The main-level guest bath keeps accessibility in mind with a sleek zero-entry shower, while a nearby half bath makes life easier for everyday traffic. Upstairs, a full suite with its own bath creates the ideal spot for visitors, multi-generational living, or a tucked-away retreat when you need a breather. Covered porches in both the front and back extend your living outdoors, while a rear-entry two-car garage keeps the curb appeal clean. Inside the garage, a wheelchair ramp provides easy access from the garage — and can be removed by the seller if not needed. Major updates are already handled: newer roof (2021), water heater (2018), and one of two HVACs replaced in 2021. Low HOA dues get you high-return perks — a resort-style pool, lake pier for fishing and star-gazing, tennis, volleyball, basketball, playgrounds, and open green space for everything else. All of it just minutes from Windermere’s shops, dining, and top-rated schools. High ceilings, natural light, updates for modern comfort — this is the Windermere vibe, done right.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Brad Young (407-897-5400)
8180 BOAT HOOK LOOP #108/301, WINDERMERE, FL 34786
$325,00095 Days on yellowkey MLS ID: TB8465266
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1442 Built: 2006 Tax: $4,422 (2024)Community: Lakeside/Lks/Windermere Ph 3Condo
Taxes:$4,422
Remarks: Discover the best of Windermere living in this meticulously maintained 3-bedroom, 2-bath CORNER UNIT condo in Lakeside at Lakes of Windermere. An expansive wrap-around screened porch embraces tranquil views and Florida breezes while providing an ideal space for morning coffee or evening relaxation. Inside, the open-concept layout features silestone countertops, cherry cabinets, and stainless appliances (2023 microwave, and upgraded dishwasher) lending a modern flair to the chef’s kitchen. Additional recent upgrades include a **2024 Carrier 15 SEER HVAC system** for comfort and energy efficiency throughout the year and **BRAND NEW 2025 new wood look porcelain tile** in all three bedrooms (NO CARPET). The generous primary suite and two additional bedrooms are thoughtfully separated for privacy. This floor plan features the closet OUTSIDE of the bathroom in the primary bedroom. Located just steps from the clubhouse and pool, this unit offers easy access to community amenities. Lakeside at Lakes of Windermere residents enjoy a fitness center, clubhouse and resort-style pool. The neighborhood is nestled near Lake Burden with access to a shared private dock and its own man-made lake. As a gated community, it also features a billiards room, walking paths around a central pond, and sports courts and fields. This home is just a few minutes drive from Walt Disney World (and neighboring parks) and boasts a view of the Disney fireworks EVERY night!! The combination of a well-appointed interior, wrap-around porch and enviable location near neighborhood amenities and Orlando's best entertainment make this corner-unit condo an exceptional opportunity.
Listing Agent: Erin Aaron (727-422-1688)
11450 ARBORSIDE BEND WAY, WINDERMERE, FL 34786
$749,901180 Days on yellowkey MLS ID: O6354816
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2622 Built: 2002Monthly Fee: $170 Tax: $4,856 (2024)Community: Glenmuir 48 39Single Family
Taxes:$4,856
Remarks: Beautifully maintained 4BR/3BA pool home in gated Glenmuir, Windermere. Open floor plan with high ceilings, formal dining, and spacious family room. Kitchen with breakfast nook overlooks screened pool/lanai. Primary suite features dual closets, spa bath, and pool access. Home includes water softener system, water heater from 2022 and air handler from 2020. Enjoy a private 0.25-acre lot in a tree-lined community. Glenmuir provides a community park with playground, basketball courts, soccer field, pavilion, and picnic areas. Conveniently located near Winter Garden Village, Lakeside Village, and Walt Disney World, the neighborhood is also zoned for top-rated Orange County schools and less than a mile from Windermere Preparatory School.
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: David Sanchez (321-262-2322)
13411 LEMON ORCHARD BND, WINDERMERE, FL 34786
$562,09518 Days on yellowkey MLS ID: TB8493546
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1649 Built: 2026Monthly Fee: $280 Tax: $8,670 (2026)Community: Lake Cawood CoveTownhouse
Taxes:$8,670
Remarks: Under Construction. This stylish two-story townhome features three spacious suites, including a second-floor primary suite and two additional bedrooms. The open-concept first floor offers a bright living area and a gourmet kitchen with 42” cabinets, quartz countertops, stainless steel appliances, and luxury vinyl plank flooring. Enjoy a private courtyard and detached two-car garage. Located in the heart of Windermere near top-rated schools, Winter Garden Village, and charming downtown, with community amenities including a pool and playground.
Listing is courtesy of: ASHTON WOODS FLORIDA REALTY LLC (813-918-4491)
Listing Agent: Reed Williams (813-918-4491)
11531 VICOLO LOOP, WINDERMERE, FL 34786
$600,00092 Days on yellowkey MLS ID: O6374016
REDUCED by $25,000 (4.0%) on 04/03/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2280 Built: 2003Monthly Fee: $122 Tax: $8,726 (2025)Community: Belmere VillageSingle Family
Taxes:$8,726
Elementary School: Lake Whitney Elem
High School: West Orange High
Middle School: SunRidge Middle
Remarks: Some homes feel like a project. This one simply feels DONE. With major improvements already completed—including a NEW ROOF, new attic insulation, and inspection items already addressed—this beautifully refreshed Belmere home offers the peace of mind buyers are looking for, along with FRESH INTERIOR PAINT, FRESH EXTERIOR PAINT, and BRAND-NEW CARPET, plus updated lighting throughout. The smart and flexible layout offers 3 bedrooms plus a dedicated office, ideal for working from home, a playroom, hobby space, or guest overflow. The office is generously sized and could easily function as a 4th bedroom-style flex space with room to add a closet if desired. You’ll appreciate the easy-care tile flooring in the main living areas, including the kitchen, baths, and family room—perfect for everyday living and effortless entertaining. The primary suite is designed as a relaxing retreat featuring a walk-in closet, soaking tub, and BRAND-NEW STEP-IN SHOWER ENCLOSURE. Sliding glass doors from the primary bedroom open directly to the covered lanai, creating the seamless indoor-outdoor connection Florida living is known for. Step outside and enjoy the COVERED LANAI overlooking a PRIVATE FENCED BACKYARD—a wonderful space for morning coffee, weekend grilling, pets at play, or simply unwinding at the end of the day. Located in gated Belmere, residents enjoy a clubhouse, community pool, fitness center, tennis courts, basketball court, and playground/park areas—all within an established Windermere community known for its convenient access to shopping, dining, and major roadways. The home is zoned for Lake Whitney Elementary, Sunridge Middle, and West Orange High, all A-rated Orange County schools, with both Lake Whitney Elementary and Sunridge Middle recognized on the district’s “Excellent” list for more than five consecutive years. With major improvements already completed, fresh finishes throughout, and a flexible floor plan, this home offers the rare combination of comfort, updates, location, and long-term value—making it easy for the next owner to simply move in and start enjoying life.
Listing is courtesy of: THE ROSENBLOOM TEAM (407-376-4454)
Listing Agent: Cindy Rosenbloom (407-876-9175)
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