Displaying: For Sale
Location: Windermere
Property Type(s): Single Family
Beds: 4 to 4
Do Not Show Listings
Windermere - 117 properties found
2806 WINDSOR HILL DR, WINDERMERE, FL 34786
$1,099,00061 Days on yellowkey MLS ID: O6385977
1 Days Off yellowkey (back on 5/18/2026)
REDUCED by $51,000 (4.4%) on 05/02/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3181 Built: 1989Monthly Fee: $111 Tax: $13,057 (2024)Community: Windsor HillSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$13,057
Elementary School: Thornebrooke Elem
High School: Olympia High
Tax Year: 2024
Middle School: Gotha Middle
Remarks: Under contract-accepting backup offers. Step into this stunning 4-bedroom, 3-bathroom pool home nestled on nearly half an acre in the highly desirable Windsor Hill community of Windermere. From the moment you enter, you’ll appreciate the bright, open floor plan designed for both comfort and effortless entertaining. At the heart of the home is a beautifully updated kitchen featuring rich walnut cabinetry, quartz countertops, a mosaic tile backsplash, touch faucet and a spacious island that seamlessly connects to the dining and living areas. Equipped with a gas range, stainless steel appliances, and ample counter space, this kitchen is perfect for gathering with family and friends. The expansive media room offers the ultimate entertainment experience, complete with a built-in media center, kitchenette, wine refrigerator, and full-size refrigerator—ideal for movie nights or hosting guests in style. Step outside to your private backyard oasis, where a sparkling heated pool and spa await. Enjoy modern features including a heater, LED lighting with remote control, and a newer pool pump. The covered outdoor living area, complete with a sink and cabinetry, creates the perfect setting for al fresco dining and relaxation. Inside, every bathroom has been thoughtfully renovated with updated vanities, mirrors, bidets, and sleek shower stalls. The luxurious primary suite boasts a spa-inspired bath with a 67-inch freestanding soaking tub, smart mirror with defog function, and dual vanities. Major system upgrades provide peace of mind, including a new roof and skylight (2021), whole-home re-plumbing (2022), water heater (2022), and pool pump (2023). Garage features an electric car charger. Combining the tranquility of suburban living with convenient access to major roadways, shopping, dining, and downtown Orlando, this move-in ready home truly has it all. The HOA features a play ground and tennis courts for neighborhood enjoyment! Don’t miss your opportunity to own this exceptional property—schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Candace Hebert (321-246-0068)
12533 CRAGSIDE LN, WINDERMERE, FL 34786
$575,00032 Days on yellowkey MLS ID: O6405628
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2151 Built: 2004Monthly Fee: $82 Tax: $8,484 (2025)Community: Lakes Windermere Ph 01 49 108Single Family
Taxes:$8,484
Elementary School: Sunset Park Elem
High School: Windermere High School
Tax Year: 2025
Middle School: Horizon West Middle School
Remarks: **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment** Welcome to Lakes of Windermere, where comfort, thoughtful upgrades, and an unbeatable Central Florida location come together in one beautifully maintained home. Inside, you’ll love the inviting layout with formal living and dining spaces accented by custom crown molding, flowing into a kitchen designed for both function and style with marble countertops, stainless steel appliances, and a large pantry—all open to the family room so everyone stays connected. Step outside to the screened patio, the perfect spot for morning coffee, weekend grilling, or winding down in the evenings. The primary suite feels like a private retreat with a tray ceiling, spacious walk-in closet, and an en-suite bath featuring dual vanities, a soaking tub, and a separate walk-in shower, while three additional bedrooms present flexible space for guests, a home office, or growing households. Major updates have already been taken care of, including a new roof (May 2022), HVAC (2021), water heater (2022), plus fresh interior paint, baseboards, and newer ceiling fans, giving you true move-in-ready peace of mind. Enjoy resort-style community amenities like tennis courts, a playground, a community pool, and a pier on Lake Sawyer, all conveniently located near shopping, dining, major highways, theme parks, and everyday essentials.
Listing Agent: Tyler Somers (561-713-8728)
5145 LATROBE DR, WINDERMERE, FL 34786
$3,299,000114 Days on yellowkey MLS ID: O6382287
REDUCED by $150,000 (4.3%) on 05/17/2026
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4512 Built: 1991Monthly Fee: $1,224 Tax: $27,776 (2025)Community: IsleworthSpa: NoSingle Family
Taxes:$27,776
Elementary School: Windermere Elem
Middle School: Chain of Lakes Middle
Remarks: Welcome to Isleworth Golf & Country Club. This home features a grand entrance that welcomes you with a spacious open foyer featuring a custom bar and a dramatic two-story living room with a fireplace, creating an impressive yet inviting setting for entertaining. Providing access from all rooms to the outdoor living area, the thoughtfully designed floor plan blends elegance and functionality throughout. The kitchen is designed for both everyday living and entertaining, featuring Thermador appliances, including a cooktop, double ovens, warming drawer, microwave, dishwasher, icemaker, and beverage refrigerator. The space overlooks a generous dinette area with direct access to the patio, seamlessly connecting indoor and outdoor living. A formal dining room and a spacious great room provide additional gathering spaces for family and guests. The primary suite, located on the first floor, is a private retreat complete with three closets and a spa-inspired bath showcasing a large walk-in shower, soaking tub, and dual vanities. A second ensuite bedroom is also conveniently located on the main level, along with a well-appointed laundry room featuring built-in cabinetry. Upstairs, the travertine staircase with iron railing leads the way to a large game room with wet bar and French doors opening to an expansive balcony overlooking the pool and golf course. Two additional ensuite bedrooms complete the upper level. Throughout the home, you’ll find plantation shutters, travertine flooring, and hardwood floors, adding warmth and sophistication. The property also features an oversized three-car garage with storage and a large driveway for ample parking.Outdoor living is truly exceptional, with a large swimming pool, covered patio with half bath, and summer kitchen with beverage refrigerator—perfect for entertaining while enjoying serene golf course views. The oversized fenced backyard offers privacy and space to relax or play. Conveniently located to shopping, dining and expressways, as well as top-rated public and private schools, this home has it all!
Listing is courtesy of: SOUTHERN REALTY GROUP LLC (407-217-6480)
Listing Agent: Teresa Stewart (407-493-3057)
14341 CREST PALM AVE, WINDERMERE, FL 34786
$1,130,64324 Days on yellowkey MLS ID: G5112469
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3153 Built: 2026Monthly Fee: $245 Tax: $1,309 (2025)Community: Palms At WindermereSingle Family
Taxes:$1,309
Elementary School: Bay Lake Elementary
Remarks: One or more photo(s) has been virtually staged. Under Construction. Arlington Floorplan – 3,153 Sq. Ft. | 4 Beds | 4 Baths | 2.5-Car Garage | Arlington with Bonus Room – a thoughtfully designed, 1-story home plus a Bonus Room on the 2nd floor that perfectly blends luxury, functionality, and comfort. This brand new 3,153 square foot residence sits on a wooded lot, offering expansive indoor and outdoor living space. Features: 4 Spacious Bedrooms: Designed for privacy and flexibility, including a luxurious owner’s suite with spa-like en-suite bathroom and large walk-in closet. 4 Full Bathrooms: Modern finishes with quartz countertops, tile flooring, and upgraded fixtures throughout.Gourmet Kitchen: A chef’s dream featuring built-in stainless steel appliances, a large center island, upgraded cabinetry, quartz countertops, a walk-in pantry, and designer lighting – perfect for hosting or everyday meals.Open-Concept Living: The heart of the home flows seamlessly from the kitchen to the dining area and large family room, all overlooking the covered lanai for indoor-outdoor living. 2.5-Car Garage: Ample space for two vehicles plus additional storage or hobby area. Projected Completion August/September. Preferred Lender incentives apply.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
9548 CROWN PRINCE LN, WINDERMERE, FL 34786
$1,450,00025 Days on yellowkey MLS ID: O6407352
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3997 Built: 1999Monthly Fee: $108 Tax: $9,227 (2025)Community: Windsor HillSingle Family
Taxes:$9,227
Remarks: Nestled on a rare half-acre lot in one of Windermere’s most sought-after communities, Windsor Hills, this FULLY RENOVATED luxury home delivers the ultimate move-in-ready, like-new lifestyle buyers are searching for. Featuring 4 spacious bedrooms, 4 beautifully updated bathrooms, and a highly desirable open-concept layout, every inch of this residence has been meticulously redesigned with today’s modern buyer in mind. The stunning chef’s kitchen is a true showpiece, appointed with brand-new premium Thermador appliances, custom cabinetry, designer finishes, and elegant lighting that elevate the entire living experience. Wide-plank luxury vinyl flooring flows seamlessly throughout the home, combining sophistication with durability and low-maintenance living. Designed for both everyday comfort and entertaining, the flexible floor plan includes an oversized upstairs BONUS ROOM, with a built-in-closet and a full bathroom, ideal for a home theater, game room, executive office, fitness studio, or private guest retreat/in-law suite. Major upgrades provide exceptional value and peace of mind, including a 2021 roof, dual high-efficiency HVAC systems (2 units/ 2026), new water heater, upgraded sliding glass doors, and an epoxy-coated garage. The expansive backyard offers endless possibilities to create your dream outdoor oasis, resort-style pool, or entertaining space. Located just minutes from the renowned Butler Chain of Lakes, championship golf courses, upscale dining, shopping, and top-rated schools, this exceptional property combines luxury, privacy, and convenience in one of Central Florida’s most desirable locations. Rarely does a fully updated home with this level of quality, land, and location become available. Some photos have been virtually staged. Furnishings shown are for illustrative purposes only and are not included in the sale.
Listing is courtesy of: DOUGLAS ELLIMAN (561-655-8600)
Listing Agent: Dianna Desboyaux (407-920-4601)
505 JENNIFER LN, WINDERMERE, FL 34786
$2,199,000102 Days on yellowkey MLS ID: O6384643
4 Days Off yellowkey (back on 5/15/2026)
REDUCED by $51,000 (2.3%) on 04/28/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3525 Built: 1989Monthly Fee: $333 Tax: $7,624 (2024)Community: Windermere OaksSpa: YesSingle Family
Taxes:$7,624
Remarks: Under contract-accepting backup offers. Villa Casablanca | Luxury Windermere Estate on 1-Acre. Some homes are built. this was transformed. Set on a rare private acre within one of Windermere’s most privately held enclaves— this estate makes an immediate architectural statement. A circular motor court, tiered fountain, and mature canopy trees establish presence before you ever step inside. What unfolds within is architectural theater. Vaulted ceilings rise to a dramatic 14-foot peak as skylights and expansive double-pane windows flood the interiors with natural light. A sculptural chandelier crowns the volume, while a full-height stone fireplace ascends as the focal point. French glass doors frame panoramic views of the private rear oasis — pool, pergola, and mature canopy beyond — creating a seamless connection between interior grandeur and outdoor serenity. The chef’s kitchen commands attention. A grand Taj Mahal quartzite island defines the center. White oak cabinetry spans floor to ceiling. The Thor range and sculpted hood rise against a full-height stone backdrop. pot filler., Viking refrigerator. Glass pendants hover overhead -- Every finish carries presence. The scullery unfolds unexpected, elevated, and unforgettable — Deep olive custom cabinetry, textured tile, LED-lit shelving, beverage refrigeration, and layered storage make it as functional as it is striking. A split plan introduces the primary suite — vaulted, private, composed. A sculptural chandelier anchors the ceiling while tailored wall moldings define the room. Dual concealed walk-in closets preserve symmetry. The primary bath is a statement of design: matte stone soaking tub beneath clerestory light, full-height stone extending into a curbless marble shower, dual tailored vanities with brushed brass accents, and patterned marble floor grounding the space in immersive opulence. An adjoining vaulted extension captures pool views and opens to the lanai. The powder room shifts tone — charcoal paneled walls, sculptural marble sink, polished brass fittings, arched mirror, and bold tile creating a rich, moody presence. A formal office behind glass French doors offers focused productivity and polished presentation. An arched corridor leads to the secondary wing where three additional bedrooms offer privacy and versatility. One suite provides direct exterior access, functioning as a cabana retreat with its own en suite bath — ideal for guests or seamless indoor-outdoor living. Outdoors, the property transforms into a private compound. A covered veranda spans the rear with classical columns and herringbone flooring. The fully equipped summer kitchen, custom wood pergola lounge, expansive lawn, fresh sod, rear gate access, and lush landscaping offer scale impossible to replicate in today’s market. Villa Casablanca is not comparable to new construction. It is rarer. Extensively renovated inside out with a long list of brand new finishes - Roof, HVAC, Double pane windows, plumbing, pool refinish, level 5 drywall smooth finish and much more. Schedule your showing today.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Ahmad Hassan, Pa (718-641-9358)
5825 OXFORD MOOR BLVD, WINDERMERE, FL 34786
$1,500,00054 Days on yellowkey MLS ID: O6399697
1 Days Off yellowkey (back on 5/15/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4319 Built: 2002Monthly Fee: $183 Tax: $16,530 (2025)Community: Oxford MoorSpa: YesSingle Family
Taxes:$16,530
Middle School: Bridgewater Middle
Remarks: Under contract-accepting backup offers. Completely Remodeled 2022 | Single Story |Gated Windermere Community | Set on nearly three-quarters of an acre in the gated Oxford Moor community, this fully remodeled single-story home delivers the kind of space and finish level that's genuinely hard to find. Wide-open living areas, high ceilings, oversized rooms, and a modern aesthetic. The kitchen provides a large island, full stone backsplash, Bosch appliances with induction cooktop and double ovens, and a dedicated coffee bar. The split floorplan separates the primary suite from the secondary bedrooms, each generously sized, while the living areas flow directly to the covered lanai and saltwater pool. The primary suite includes a sitting area, expanded closet, and a fully renovated bath. A large private office comfortably fits dual workstations. Outdoor living space includes the saltwater pool running on updated equipment and automation, surrounded by a spacious fenced yard framed by mature landscaping and fruit trees that actually produce. Oxford Moor is one of Windermere's quieter gated communities comprised of 85 Estate Homes. Top-rated schools including Windermere Elementary, Bridgewater Middle, Windermere High school, and less than 1 mile from Windermere Prep, convenient SR 429 access, and a short drive to Walt Disney World round out the location.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Jeffrey Funk, Pa (407-285-9672)
2127 LILYPAD LN, WINDERMERE, FL 34786
$1,250,00039 Days on yellowkey MLS ID: O6403899
0 Days Off yellowkey (back on 5/14/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3349 Built: 1989Monthly Fee: $122 Tax: $10,870 (2025)Community: Willows At Lake Rhea Ph 01Spa: YesSingle Family
Taxes:$10,870
Remarks: Under contract-accepting backup offers. Welcome to a rare opportunity in the highly sought-after Willows at Lake Rhea, where incredible design, extensive upgrades, and an elevated Windermere lifestyle come together on a private ½-acre cul-de-sac lot in one of Central Florida’s most desirable luxury communities. This exceptional 4-bedroom, 3-bath residence features a thoughtfully designed split floor plan with two dedicated home offices and a versatile flex space complete with a built-in bar, currently designed as a sports and media room with multiple TVs, soundbar, and its own independent AC, creating the perfect balance of productivity and entertainment. At the center of the home, a fully reimagined custom designer kitchen flows seamlessly into the main living areas and showcases premium finishes, high-end appliances, and a reverse osmosis system, all complemented by architectural details like shiplap ceilings, barn doors, and curated lighting that add warmth and sophistication throughout. The outdoor living space is a beautifully landscaped setting with mature trees and a heated inground saltwater pool and spa featuring a color-changing LED lighting system, designed for both relaxation and hosting. This home has been meticulously upgraded with over $400,000 in improvements including a new roof, windows, doors, gutters, AC, smart WiFi thermostats, a smart WiFi hybrid hot water heater, smart WiFi Sprinkler controller, interior and exterior paint, pool equipment, and a Tesla charger, offering true peace of mind and move-in confidence, along with AT&T fiber internet delivering 1G/1G speeds for seamless connectivity. A side-entry 3-car garage, plantation shutters, and too many other details to list complete the home, while the location delivers unmatched convenience with walking distance to the Windermere Farmer’s Market, zoning for top-rated Windermere High School, and quick access to Winter Garden Village, the 408, and 429. Residents also enjoy community amenities including a park, basketball, and pickleball courts, all surrounded by the charm of Windermere and the lifestyle of the Butler Chain of Lakes, making this more than a home, it is a refined living experience that checks all the boxes in a community that truly offers it all. You have found your forever home.
Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)
Listing Agent: Angela Jaspon (407-235-0093)
13609 ANCILLA BLVD, WINDERMERE, FL 34786
$749,999116 Days on yellowkey MLS ID: O6381542
0 Days Off yellowkey (back on 5/12/2026)
REDUCED by $39,001 (4.9%) on 04/14/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3360 Built: 2005Monthly Fee: $130 Tax: $9,521 (2024)Community: Summerport Ph 03Single Family
Taxes:$9,521
Elementary School: Keene Crossing Elementary
Remarks: One or more photo(s) has been virtually staged. Welcome to this stunning and spacious single-family home located in the heart of Windermere, offering breathtaking lake views from both the front and rear of the property. With 3,360 sqft heated living space, this beautifully maintained residence features a thoughtfully designed floor plan ideal for comfort and functionality. The first floor includes a private primary suite with its own balcony, providing a serene retreat, as well as a dedicated home office perfect for remote work or study. Generous living areas are filled with natural light and create a seamless connection between indoor and outdoor living. Step outside to enjoy the covered patio and expansive backyard, offering ample space for entertaining, relaxing, or future customization. The property sits on a well-sized lot and is part of a community that features amenities such as a pool, park, playground, and sidewalks. Conveniently located near top-rated schools, shopping, dining, and major roadways, this home delivers an exceptional combination of location, space, and lifestyle. A rare opportunity to own a lake-view property in one of Windermere’s most desirable areas. Schedule your private showing today. SOME IMAGES HAVE BEEN VIRTUALLY STAGED AND/OR DIGITALLY ENHANCED TO ILLUSTRATE THE PROPERTY'S POTENTIAL AFTER UPDATES OR RENOVATIONS.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Fernanda Soares Santos De Oliveira (407-840-0734)
606 E 6TH AVE, WINDERMERE, FL 34786
$2,350,00083 Days on yellowkey MLS ID: O6390327
2 Days Off yellowkey (back on 5/13/2026)
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4471 Built: 2016 Tax: $25,043 (2025)Community: DiamondheadSingle Family
Taxes:$25,043
Remarks: Experience elevated lakefront living in this one-of-a-kind estate, offering breathtaking views of Lake Bessie and unforgettable Florida sunsets. A private gated entry welcomes you to this exceptional residence, featuring 3 bedrooms and 3.5 bathrooms, plus a private in-law suite with its own full bath bringing the total to 4 bedrooms and 4.5 bathrooms. Thoughtfully designed for both everyday living and elegant entertaining, this home offers the perfect blend of comfort, privacy, and sophistication. The main level features formal living and dining rooms with a fireplace, along with a private office just off the foyer. The gourmet kitchen is a chef’s dream, showcasing custom cabinetry, built-in wine rack, wine refrigerator, Sub-Zero refrigerator, custom lighting, gas range, and a spacious pantry. A convenient half bath and oversized laundry room are also located on the main floor. Upstairs, you’ll find two private suites, each with its own full bathroom, plus the luxurious owner’s retreat offering stunning lake views, custom tile floors and walls, a separate walk-in shower, jetted soaking tub, custom lighting, and a large walk-in closet with built-in cabinetry. Step outside to your resort-style oasis featuring large pool with expansive deck and water feature. Two additional outdoor entertaining areas include a dedicated space with an outdoor kitchen. The pool house offers large windows with panoramic views, custom cabinetry, granite countertops, upgraded tile flooring, a Murphy bed, and a full custom bathroom, perfect for guests. Complete with a covered boat dock and located just a few blocks from downtown Windermere and nearby shopping, this extraordinary home blends luxury, comfort, and the ultimate Florida lifestyle.
Listing is courtesy of: ELITE GLOBAL REAL ESTATE LLC (407-758-2604)
Listing Agent: Maria Sarmiento Webel (305-793-6614)
8632 ABBOTSBURY DR, WINDERMERE, FL 34786
$625,00032 Days on yellowkey MLS ID: O6406433
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2720 Built: 2004Monthly Fee: $167 Tax: $8,567 (2025)Community: Lakes/Windermere-PeachtreeSingle Family
Taxes:$8,567
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully updated 4-bedroom, 3.5-bath home located in the highly desirable gated community of Lakes of Windermere. Featuring fresh interior paint and luxury vinyl flooring, this spacious residence offers a modern, clean, and move-in-ready feel with an ideal layout for both everyday living and entertaining. The remodeled first floor creates a bright and inviting atmosphere, while the screened-in outdoor area provides the perfect space to relax and enjoy Florida living year-round. Community amenities include a resort-style pool, playground, and beautifully maintained common areas. Ideally located near shopping, dining, major highways, Disney attractions, and top-rated Windermere schools, this property is an excellent opportunity for homeowners and investors alike. Strong rental demand and a prime location make this home a standout opportunity in one of Central Florida’s most sought-after communities. Schedule your private showing today!
Listing Agent: Priscila Policarpo Attuy De Albuquerque (321-947-5121)
5413 WALSH POND CT, WINDERMERE, FL 34786
$800,00077 Days on yellowkey MLS ID: O6391919
REDUCED by $75,000 (8.6%) on 05/09/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3124 Built: 2006Monthly Fee: $130 Tax: $10,646 (2025)Community: Edens HammockSpa: YesSingle Family
Taxes:$10,646
Remarks: Discover the charm of this water front, 4 bedroom 3.5 bath home located in the desirable Summerport community. This unique property is nestled in the cul de sac for complete privacy. Enjoy scenic water views while relaxing poolside on the spacious screen enclosed lanai, which is also great for entertaining. The interior features granite countertops, stainless appliances, 42" cabinets, built in speakers on both levels and exterior. The community amenities include pool, fitness center, tennis courts, clubhouse, parks, dock, and walking paths. Conveniently located near theme parks, dining, and shopping.
Listing is courtesy of: HAVEN PROPERTY GROUP LLC (407-928-3894)
Listing Agent: Brenda Jebailey (407-361-2101)
6560 LAKE BURDEN VIEW DR, WINDERMERE, FL 34786
$1,890,000110 Days on yellowkey MLS ID: O6381835
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3687 Built: 2006Monthly Fee: $298 Tax: $24,050 (2025)Community: Keenes PointeSpa: YesSingle Family
Taxes:$24,050
Remarks: Experience refined, single-level living in this exceptional custom home located within Keene’s Pointe, Windermere’s premier guard-gated golf and lakefront community. Designed with both privacy and comfort in mind, this beautifully appointed residence offers 4 bedrooms, 4 full baths, a private office, and a resort-style pool and spa. At the front of the home, the dedicated office enjoys tranquil water views, creating an inspiring workspace. Inside, expansive windows frame the sparkling pool and spa, filling the living spaces with natural light and creating a seamless indoor-outdoor ambiance. Contemporary interior updates lend a true “jewel box” feel, with luxury finishes throughout. Neutral designer tones, upgraded Viking appliances, two newer A/C units, and custom iron Cantera double entry doors add both elegance and sophistication. The spacious three-car garage is discreetly tucked at the rear of the property, allowing the home’s striking front elevation and exceptional curb appeal to shine. Situated on an oversized one-third-acre lot overlooking the Camden River, the property offers generous green space and picturesque water views that enhance its impressive setting. Residents of Keene’s Pointe enjoy a sought-after country club lifestyle, with optional membership to the Golden Bear Club offering championship golf, tennis, dining, and a vibrant social calendar—making this one of Central Florida’s most desirable places to call home.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Rob Rahter (407-497-4526)
8525 BOWDEN WAY, WINDERMERE, FL 34786
$999,00034 Days on yellowkey MLS ID: O6405195
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2357 Built: 2000Monthly Fee: $298 Tax: $5,825 (2025)Community: Keenes PointeSpa: NoSingle Family
Taxes:$5,825
Remarks: Keene's Pointe - 24-hour gated/attended community in Windermere, Florida. 4 bedroom/3 bath home with formal living and dining rooms, kitchen and great room. This quaint home features a functional floor plan. Kitchen with newer stainless appliances, open concept floor plan joining the kitchen, nook and great room and private primary with walk-in closet and bath with dual vanities, shower and garden tub. Enjoy peaceful evenings in the private back yard with spacious lanai, screened oversized pool and large yard. The fourth bedroom is currently being used as a den with French doors. NEW ROOF IN 2022, WATER HEATER 2020, two car garage with storage, and much more. Discover all this community has to offer, including The Golden Bear Club, a private 18-hole golf course designed by Jack Nicklaus offering golf, tennis, swimming, dining and clubhouse. Located close to shopping, dining, expressways and top-rated public and private schools, this home is perfect as a primary home or vacation home. Call today for you private viewing.
5138 FAIRWAY OAKS DR, WINDERMERE, FL 34786
$5,500,00045 Days on yellowkey MLS ID: O6401757
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4330 Built: 1994Monthly Fee: $1,224 Tax: $19,599 (2025)Community: IsleworthSpa: YesSingle Family
Taxes:$19,599
Remarks: Set along Isleworth’s signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Isleworth Golf & Country Club—recognized among the finest private club communities in the world. Encompassing more than 4,300 square feet, the single-story residence has been completely transformed inside and out. Thoughtfully redesigned interiors showcase all-new flooring throughout, beautifully renovated bedrooms and baths, and a striking glass-enclosed wine tower serving as a true centerpiece that is both functional and an unforgettable conversation element anchoring the main living spaces. Every detail throughout the home has been elevated, from designer lighting installations that bring character and sophistication to each room, to the seamless flow of living and entertaining spaces. The kitchen is a true showpiece, featuring all-new appliances—including a striking black range with matching hood, refrigerator, and microwave—all accented with elegant gold detailing for a bold, designer-forward statement. Custom cabinetry is paired with exquisite countertops, highlighted by a dramatic waterfall-edge island that anchors the space and seamlessly blends everyday functionality with elevated, modern style.The outdoor living area features a reimagined pool and all-new pool deck creating a resort-style setting, perfectly positioned to take in breathtaking sunsets over the golf course and water. The half-acre homesite has been thoughtfully cleared and fenced to maximize both privacy and panoramic views, offering an exceptional backdrop for everyday living and entertaining alike. Framed by the fairways, the residence captures views of Lake Brenda - also known as Hourglass Pond - a small, privately maintained 10-acre water body that serves as a peaceful and picturesque part of the community setting. Additional features include a home office, in-home laundry room, and a three-car garage. Residents of Isleworth enjoy an unparalleled lifestyle surrounded by the Butler Chain of Lakes, with access to world-class golf, dining, and amenities, all just moments from Central Florida’s premier shopping, dining, and entertainment destinations.
Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)
Listing Agent: Monica Lochmandy (407-230-6888)
436 E 7TH AVE, WINDERMERE, FL 34786
$2,175,000244 Days on yellowkey MLS ID: O6350454
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3136 Built: 2025 Tax: $13,016 (2025)Community: Windermere Town RepSingle Family
Taxes:$13,016
Elementary School: None
High School: None
Middle School: None
Remarks: Seller is Motivated and open to negotiate! Luxury new construction lakefront home in Windermere, newly completed. Situated on Lake Bessie, this modern custom residence delivers architectural elegance, premium finishes, and a prime location just steps from the Town Center. The home offers 3,136 sq ft of air-conditioned space, featuring 4 en-suite bedrooms, a dedicated office at the entry, 5 full bathrooms, an outdoor shower, and an oversized 3-car garage. A dramatic two-story living area sets the tone with clean lines, expansive glass, and natural light throughout. The chef’s kitchen pairs performance and elegance, with a waterfall-edge quartz island, full-height book-matched backsplash, custom cabinetry, and high-end appliances including a Sub-Zero refrigerator, Wolf vent hood, and a full Thermador suite with double ovens and microwave drawer. A hidden walk-in pantry blends seamlessly into the design for added utility and clean aesthetics.Upstairs, the owner’s suite offers lake views, a spacious layout, and a sleek en-suite bath with a large walk-in shower and dual vanity. Secondary bedrooms include en-suite baths and reach-in closets. The home is finished with oversized rectangular porcelain tile throughout the entire main level including the expansive covered lanai and wide plank engineered wood flooring from the staircase through the second floor. Additional highlights include a glass-framed staircase and an abundance of natural light in every space. Located just blocks from Downtown Windermere, this home places you at the center of a highly coveted lakefront lifestyle. Enjoy tennis courts, playgrounds, boat ramps on both Lake Bessie and the Butler Chain, plus a vibrant local culture with weekly farmers markets, food truck nights, and seasonal events in Town Square. Cruise oak-lined sandy streets by golf cart, or explore nearby dining, shops, and fitness at The Grove and along Restaurant Row. World-class golf, theme parks, and the airport are all within easy reach and with the hard work already done, all that’s left is to move in and enjoy. Private showings by appointment only. Seller is Motivated and open to negotiate! We completed the closets upgrades in this beautiful home, thoughtfully designed for the family who will soon call this place home.
Listing is courtesy of: TALENT REALTY SOLUTIONS (407-910-2020)
Listing Agent: Deniley Valdes (407-922-3870)
5151 LATROBE DR, WINDERMERE, FL 34786
$3,900,00081 Days on yellowkey MLS ID: O6392380
REDUCED by $200,000 (4.9%) on 05/05/2026
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 5301 Built: 2000Monthly Fee: $1,224 Tax: $23,020 (2025)Community: IsleworthSpa: NoSingle Family
Taxes:$23,020
Remarks: Positioned along the stunning 4th fairway of the renowned Isleworth Golf & Country Club, this exceptional single-story estate offers four bedrooms and more than 5,300 square feet of meticulously crafted living space. Every detail of this residence reflects the owner’s exceptional craftsmanship, with bespoke woodwork woven throughout the home, culminating in the crown jewel: the primary suite’s expansive wardrobe, featuring a central island, tiger wood floors, and cherry birch built-in displays—a true collector’s dream. The elegant foyer sets the tone, leading to formal living and dining spaces, and flowing effortlessly past a private office into the heart of the home: an open-concept kitchen, casual dining area, and family room designed for both entertaining and daily living. The gourmet kitchen is appointed with anigre wood cabinetry, a center island, dual sinks, a walk-in pantry, and professional appliances by Sub-Zero, Dacor, and Kitchenaid, marrying style and functionality in perfect harmony. A spacious game room with a wet bar provides an ideal space for recreation or hosting, while four luxurious bedrooms and 4.5 spa-inspired baths ensure comfort and privacy for family and guests alike. Seamlessly blending indoor and outdoor living, the estate features a sparkling open-air pool set against serene golf course vistas—an idyllic setting for year-round leisure and entertaining. Additional highlights include a circular driveway and motor court, a three-car garage, and a separate workshop. This is a rare opportunity to acquire a residence where world-class craftsmanship, refined design, and premier golf-front location converge, offering an unparalleled lifestyle in one of Central Florida’s most coveted enclaves.
2 CHASE RD, WINDERMERE, FL 34786
$3,200,000265 Days on yellowkey MLS ID: O6345197
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3889 Built: 2026 Tax: $3,100 (2024)Community: WindermereSingle Family
Taxes:$3,100
Remarks: Pre-Construction. To be built. Pre-Construction. To be built. Pre-Construction | To Be Built | Designed for Unparalleled Luxury Discover an extraordinary opportunity to own a masterfully designed luxury residence in this Windermere community. This exquisite estate, crafted by the renowned Supreme Construction, offers a perfect blend of sophistication, innovation, and timeless elegance. Property Highlights: • Total Living Area: 3,889 Sq. Ft. | Total Building Area: 5,516 Sq. Ft. • 4 Bedrooms | 4 Full Baths | 1 Powder Room | 1 Pool Bath • Expansive Living Spaces with High Ceilings & Open Floor Plan • Great Room | Dining Room | Gourmet Kitchen with Nook & Pantry • Private Elevator & Multiple Open Decks • 2-Car Garage First-Floor Features: • Grand Foyer with Staircase & High Ceilings • Great Room & Elegant Dining Room • Chef’s Gourmet Kitchen with custom cabinetry, quartz countertops, Subzero appliances, and a spacious island • Guest Suite with Private Bath & Walk-in Closet • Laundry Room & Powder Bath • Pool Bath (Outdoor Access) Second-Floor Features: • Lavish Master Suite with Private Balcony, Spa-Inspired Bath & Custom Walk-in Closet • Two Additional Bedrooms with Walk-in Closets & Shared Designer Bathroom • Two Expansive Open Decks for Outdoor Enjoyment Luxury Amenities & Smart Home Features: • State-of-the-Art Smart Home Integration • Hurricane Impact Windows for Safety & Efficiency • Custom California Closets in All Bedrooms • Heat & Glow Fireplaces in the Living Room & Master Suite • Large Format Porcelain Tile & High-End Finishes Throughout • Flat Tile Roof & Metal Truss Construction for Durability Outdoor Oasis & Entertainment Haven: • Resort-Style Custom Pool & Spa (Separate Permit) • Sunken Outdoor Kitchen & Lounge Area for Elevated Entertaining • Landscaped Backyard with Ample Space for Relaxation & Gatherings Prime Windermere Location – Unmatched Lifestyle & Convenience: • Minutes from Isleworth, Home to Celebrities & Sports Icons • Access to the Pristine Butler Chain of Lakes – Ideal for Boating & Water Sports • A-Rated Schools, Parks, & Year-Round Community Activities • Close to Luxury Shopping, Fine Dining, Golf Courses & Entertainment • Easy Access to Disney, Universal, and Orlando’s Top Attractions This exceptional luxury estate embodies a lifestyle of sophistication, exclusivity, and modern convenience. Secure this once-in-a-lifetime opportunity to own a masterpiece of design and craftsmanship in the heart of Windermere. For more details, floor plans, and customization options, contact us today!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Matthew Hughes (407-619-4717)
9319 WOODBREEZE BLVD, WINDERMERE, FL 34786
$554,555106 Days on yellowkey MLS ID: O6384930
REDUCED by $20,440 (3.6%) on 04/30/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1798 Built: 1986Monthly Fee: $30 Tax: $3,384 (2024)Community: Silver WoodsSingle Family
Taxes:$3,384
Remarks: WONDERFUL WINDERMERE 4 BED/ 2 BATH HOME LOCATED IN THE CHARMING COMMUNITY OF SILVER WOODS. The moment you drive up to this home you are greeted by low maintence landscaping, paver driveway and a unique courtyard entry which makes this home standout. The courtyard is a perfect space to spend the evenings or start your mornings. Sliders from the kitchen lead onto the courtyard. Upon entering you will notice the details: beveled glass front door, split floorplan, large dining and living (open concept) and well-appointed kitchen. The kitchen overlooks the Livingroom and dining room, and boost upgrades you are sure to love. Cherrywood cabinets with pullout shelves, glass doors, pantry, under cabinet lighting, decorative lighting in cabinets, stainless steel appliances and upgraded granite counters. Additional cabinets were added to create workspace or an eat in kitchen space. Just off the kitchen if the laundry area with matching cabinets. The spacious living room is positioned with views of the kitchen and dining space with sliders leading to the massive patio space. Two additional bedrooms are located just off the living room with the hall bath set up for a pool bath if you decided to add one. Just off the dining room you will find the primary bedroom with French doors leading to a private patio space. The primary bath includes a walk in closet space, cherrywood cabinets and a walk in shower. The rear patio has just as many endless options as the front courtyard does...dining spaces or entertaining or both! All this in a home and still just minutes to restaurants, entertainment, shopping, the parks and so much more. Land, Site, and Tax Information
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Steven Looper (321-662-3582)
8323 LOOKOUT POINTE DR, WINDERMERE, FL 34786
$590,00069 Days on yellowkey MLS ID: O6393407
0 Days Off yellowkey (back on 4/28/2026)
REDUCED by $9,999 (1.7%) on 04/24/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2633 Built: 2016Monthly Fee: $75 Tax: $9,688 (2025)Community: Windermere Trls Ph 3BSingle Family
Taxes:$9,688
Remarks: Under contract-accepting backup offers. Beautiful 4 bedroom, 3.5 bath home located in the highly sought-after subdivision of Windermere Trails. The first floor has tile flooring and a spacious kitchen equipped with granite countertops, 42'' cabinets, a center island, and a walk-in pantry. Step through the dining room to a beautifully finished courtyard, complete with a private fence and elegant stone pavers. Upstairs, you'll find an additional room with double doors, perfect for a gathering space or home office. The primary bedroom features a large walk-in closet for ample storage. All interior has recently been painted, all carpets upstairs in the main home are new, as well as the AC unit is brand new, ensuring comfort and efficiency. This beautiful home layout provides the opportunity to convert this four bedroom home into six bedrooms. One of the rooms downstairs can easily be converted, as it’s already closed off; you just need to add a closet. Additionally, the loft upstairs is also closed off and simply missing a closet, offering another potential bedroom. This home has a separate private one - bedroom apartment above the garage, featuring a kitchenette, walk in closet, private entrance, and its own washer and dryer with a four month old A/C unit. Conveniently located off Winter Garden Vineland Rd. This home provides easy access to I-4, 429, and is just a short distance from all Disney Theme Parks. Enjoy the benefits of low HOA fees and being close to exceptional A+ schools.
Listing is courtesy of: WEST ORLANDO PROPERTY MANAGEMENT REALTY, LLC (407-922-9169)
Listing Agent: Ricardo Diaz (407-922-6196)
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