Location: Windermere
Do Not Show Listings
505 JENNIFER LN, WINDERMERE, FL 34786
$2,250,00057 Days on yellowkey MLS ID: O6384643
1 Days Off yellowkey (back on 3/27/2026)
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 3525 Built: 1989Monthly Fee: $333 Tax: $7,624 (2024)Community: Windermere OaksSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,624
Elementary School: Windermere Elem
High School: Olympia High
Tax Year: 2024
Middle School: Chain of Lakes Middle
Remarks: Under contract-accepting backup offers. Villa Casablanca | Luxury Windermere Estate on 1-Acre. Some homes are built. Villa Casablanca was transformed. Set on a rare private acre within one of Windermere’s most privately held enclaves— this white-painted brick 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. Bay windows overlook the fountain and motor court, creating a balanced dialogue between arrival and retreat. 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, smooth drywall level 5 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)
11536 CLAYMONT CIR, WINDERMERE, FL 34786
$1,250,00030 Days on yellowkey MLS ID: O6392958
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2882 Built: 2002Monthly Fee: $298 Tax: $8,766 (2025)Community: Keenes Pointe Ut 04 Sec 31 48 82Single Family
Taxes:$8,766
High School: Winter Park High
Tax Year: 2025
Middle School: Bridgewater Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to luxury living inside the guard-gated community of Keene’s Pointe, home to the renowned Golden Bear Club and its Jack Nicklaus Signature golf course. Perfectly positioned within one of Windermere’s most sought-after neighborhoods, this exceptional single-story residence offers a refined blend of elegance, comfort, and lifestyle. Beautifully remodeled throughout, this is truly move-in ready, showcasing a fresh, modern aesthetic while maintaining timeless architectural appeal. From the moment you enter, you’re welcomed by marble tile flooring, newly refinished wood floors, fresh interior paint, and thoughtfully selected modern light fixtures that elevate every space. The home features both a traditional dining room and formal living room, complemented by custom window treatments that add warmth and sophistication. At the heart of the home, the completely remodeled kitchen shines with all-new appliances, a gas stove, double oven, quartz countertops, and a large walk-in pantry, all wrapped in a clean, contemporary design that seamlessly opens to the family room—where a decorative modern fireplace creates the perfect gathering space. The expansive primary suite is a true retreat, featuring wood floors, direct pool access, a dedicated mini-split system for enhanced comfort and efficiency, and a spa-inspired bathroom with a stunning new garden tub, separate shower, and an oversized walk-in closet. Additional bedrooms lend to stylish comfort with new herringbone tile flooring and share a convenient Jack-and-Jill bathroom. All bathrooms throughout the home have been fully remodeled with high-end finishes. A large private office with a built-in desk provides the ideal work-from-home environment. Step outside to a spacious, fenced backyard featuring a newly repainted pool and patio—perfect for enjoying Florida living year-round. Additional highlights include a 2020 roof, paver driveway, and an oversized 3-car garage. Every detail has been thoughtfully updated, making this home completely turn-key. Residents of Keene’s Pointe enjoy 24-hour guard-gated security and a lifestyle centered around both recreation and natural beauty. The community offers private access to the Butler Chain of Lakes, ideal for boating, skiing, and sunset cruises, along with scenic walking paths, tranquil green spaces, and a peaceful, well-maintained setting throughout. There is even the opportunity for boat storage, adding convenience for those looking to fully embrace the lake lifestyle. Optional membership to the Golden Bear Club unlocks a premier lifestyle experience with championship golf, tennis, fitness, a resort-style pool, dining, and a vibrant calendar of social events. The neighborhood also features community parks, playgrounds, and gathering spaces, creating a welcoming environment that blends luxury living with everyday convenience and community connection through regular neigborhood events. Whether you're relaxing poolside, entertaining guests, or enjoying the unmatched lifestyle of this premier golf and lakefront community, this home delivers the very best of Central Florida living.
Listing is courtesy of: MATT ALLEN REAL ESTATE LLC (321-228-5555)
Listing Agent: Matt Allen (321-228-5555)
436 E 7TH AVE, WINDERMERE, FL 34786
$2,175,000199 Days on yellowkey MLS ID: O6350454
Bed: 4 Bath: 5.0 Liv Area Sq Ft: 3136 Built: 2025Community: Windermere Town RepSingle Family
Taxes:
Elementary School: None
High School: None
Tax Year:
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)
14285 CREST PALM AVE, WINDERMERE, FL 34786
$1,019,99091 Days on yellowkey MLS ID: G5107224
0 Days Off yellowkey (back on 3/25/2026)
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 3100 Built: 2025Community: Palms At WindermereSingle Family
Remarks: One or more photo(s) has been virtually staged. Welcome to the Arlington with Bonus a stunning 4-bedroom, 4-bathroom home offering 3,123 square feet of beautifully designed living space. Thoughtfully crafted with an open-concept layout, this home is perfect for both everyday living and entertaining. Step inside to find soaring 10-foot ceilings on the first floor and durable laminate flooring throughout, creating a seamless and modern feel. The gourmet kitchen is a true centerpiece, featuring elegant quartz countertops, a large center island, and abundant cabinet space—ideal for hosting and meal preparation alike. The spacious floor plan includes a versatile second-floor bonus room complete with a full bath, perfect for a guest suite, media room, or home office. The elegant primary bathroom offers a spa-like retreat, featuring a spacious walk-in shower with a luxurious rain shower head and a dual vanity with ample counter space. Situated on a desirable conservation homesite, this property offers added privacy and serene natural views. The oversized garage provides ample room for vehicles, storage, or even a workshop. This home effortlessly combines style, functionality, and comfort.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Cindy Sapp (352-516-2843)
7432 LEIGHSIDE DR, WINDERMERE, FL 34786
$475,00061 Days on yellowkey MLS ID: O6383362
2 Days Off yellowkey (back on 3/25/2026)
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 1898 Built: 2014Community: Lake Burden South Ph 2Townhouse
Remarks: Under contract-accepting backup offers. Welcome to this beautifully upgraded 4-bedroom, 2.5-bath, home with a 2-car garage, located in a quiet and highly desirable Windermere community that truly invites you to enjoy the Florida lifestyle. The spacious primary suite is conveniently located on the first floor, offering comfort and privacy. The home features recent upgrades including a renovated kitchen, updated bathrooms, and new flooring, making it move-in ready. Residents enjoy wonderful community amenities such as a clubhouse, resort-style swimming pool, tennis courts, and scenic walking paths, perfect for relaxing or staying active. Ideally situated just minutes from Walt Disney World, major highways, top-rated A schools, shopping centers, supermarkets, restaurants, and everyday conveniences. This property offers the perfect combination of location, lifestyle, and value, ideal as a primary residence, vacation home, or investment opportunity in one of Central Florida’s most sought-after areas..
Listing is courtesy of: METROPOLITAN R.E SOLUTIONS INC (407-953-6501)
Listing Agent: Belkys Zambrano (407-516-9103)
9225 MCDAVID CT, WINDERMERE, FL 34786
$835,00042 Days on yellowkey MLS ID: O6390371
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2713 Built: 1984Community: Roberts LandingSingle Family
Remarks: Welcome to this beautifully maintained custom 4-bedroom, 2-bath pool home set on a full 1-acre lot in a quiet, established neighborhood. Built and lovingly cared for by the original owner, this home offers a bright, airy interior with timeless wood trim details that add warmth and character throughout. The spacious family room features a wood-burning fireplace, creating a comfortable gathering space for everyday living and entertaining. Designed for enjoying Florida living, the home includes a large enclosed Florida Room with views of the pool and expansive backyard. Step outside to the extra-large pool deck—perfect for relaxing, hosting friends, or enjoying sunny afternoons. The pool area is fully fenced for added safety. Car enthusiasts, hobbyists, or those needing extra storage will appreciate the oversized side-facing 3-car garage, complete with a dedicated workshop area. The generous one-acre property provides space to spread out, garden, or simply enjoy the peaceful surroundings. Conveniently located near shopping, the local library, and medical facilities, and zoned for highly regarded schools, this home offers both privacy and everyday convenience. With well and septic already in place, you’ll also enjoy the benefit of no water or sewer bills. A wonderful opportunity to own a meticulously cared-for home with space, character, and room to enjoy the Florida lifestyle.
Listing is courtesy of: CENTURY 21 CARIOTI (407-573-2121)
Listing Agent: David Vannoy (702-245-6071)
12235 MONTALCINO CIRCLE, WINDERMERE, FL 34786
$1,899,924140 Days on yellowkey MLS ID: O6365656
Bed: 4 Bath: 4.5 Liv Area Sq Ft: 4550 Built: 2018Community: Casa Del Lago RepSingle Family
Remarks: Casa del Lago gated community in Windermere, Florida. Exquisite 4 bedroom/4.5 bath luxury residence showcasing exceptional craftsmanship and high-end finishes throughout. As you arrive you are welcomed by a circular driveway and quaint courtyard entrance. The first floor boasts a formal dining room,and a spacious gathering room anchored by a stunning stone two-sided fireplace. A dedicated 1,275-bottle wine cellar with tasting and corking areas elevates the home’s entertainment appeal. The gourmet kitchen features Thermador appliances, a generous island, a walk-in pantry, and a Butler’s area—perfect for hosting on any scale. A private primary suite offers direct access to the patio and pool, along with a spa-inspired en-suite bath. This retreat features stone wall accents, a luxurious indoor shower plus an outdoor shower with dual rain heads, and an expansive, custom-designed closet with three separate areas and built-in shelving.Also on the main level are two additional en-suite bedrooms, one with a private entrance from the front courtyard—ideal for guests or multi-generational living. A large laundry room with built-in refrigerator and freezer and additional storage room adds convenience and functionality. The gathering room with built-in entertainment center and 16ft sliding glass doors opens seamlessly to the private outdoor patio with summer kitchen, gas fireplace, and screened resort-style swim-spa, as well as sitting area with fire pit, creating an effortless indoor-outdoor flow.Upstairs, a spacious club room awaits—complete with built-in entertainment center and abundant storage—perfect for gaming, media, or relaxed lounging. The upper level also includes a fourth en-suite bedroom with walk-in closet and a large closet for holiday storage. This home also has a 3-car split garage, hardwood flooring, wood paneled and beamed ceilings, plantation shutters, and custom details throughout. A rare blend of elegance, comfort, and thoughtful design—crafted for luxurious everyday living and exceptional entertaining. Located close to shopping, dining, top-rated public and private schools, expressways and tourist attractions, this home has everything you are looking for. Call for your private viewing today.
Listing is courtesy of: SOUTHERN REALTY GROUP LLC (407-217-6480)
Listing Agent: Teresa Stewart (407-493-3057)
5413 WALSH POND CT, WINDERMERE, FL 34786
$875,00032 Days on yellowkey MLS ID: O6391919
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 3124 Built: 2006Community: Edens HammockSingle Family
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)
8582 POWDER RIDGE TRL, WINDERMERE, FL 34786
$670,000263 Days on yellowkey MLS ID: S5132123
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 2297 Built: 2017Community: Windermere Trls Ph 3BSingle Family
Remarks: AN IRRESISTIBLE INVESTMENT OPPORTUNITY — OR YOUR FIRST HOME! Welcome to this stunning Kipling model offering serene lake views and a host of exceptional upgrades. This home features fully paid-off solar panels, electric vehicle charging outlets, and a whole-house water filtration system for maximum efficiency and comfort. Step inside and enjoy the spacious loft above the garage, new carpeting, and custom window blinds throughout. The gourmet kitchen is equipped with stainless steel KitchenAid appliances, granite countertops, and a stylish backsplash. Laminate floors and LED-lit cabinetry enhance the home’s modern elegance. Outside, enjoy a fully renovated fence, a paved terrace, and stone walkways, creating the perfect outdoor living space. Located just minutes from Disney parks, restaurants, and major shopping centers, this home is a prime opportunity for savvy investors or first-time buyers ready to make this their dream home. Don’t miss out on the chance to combine financial stability with the unmatched appeal of Disney-area living!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Mariana Rondon (407-607-3558)
7924 BROFIELD AVE, WINDERMERE, FL 34786
$650,00036 Days on yellowkey MLS ID: S5146185
0 Days Off yellowkey (back on 3/24/2026)
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1709 Built: 2011Community: Lake Sawyer South Ph 04Single Family
Remarks: Under contract-accepting backup offers. Beautiful 3-bedroom, 2.5-bath home fully remodeled in a modern style. This move-in ready property features a 2023 A/C system, plus an additional A/C unit in the garage for added comfort and versatility. The backyard offers peaceful conservation views, providing privacy and a relaxing natural setting. Located in a highly desirable Berkshire Park community with excellent amenities, including a playground, swimming pool, and tennis courts—perfect for enjoying an active and family-friendly lifestyle. Conveniently situated with easy access to shopping, dining, and major roadways. This home combines style, comfort, and location—ideal for today’s lifestyle. Property is being sold AS IS.
Listing is courtesy of: ALTIS REALTY (407-401-7447)
Listing Agent: Maria Pa Virgilio (321-947-5650)
12989 WESTSIDE VILLAGE LOOP, WINDERMERE, FL 34786
$655,00039 Days on yellowkey MLS ID: S5145903
3 Days Off yellowkey (back on 3/24/2026)
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 2665 Built: 2018Community: Westside VillageSingle Family
Remarks: nergy-efficient home. This 4 beds and 3.5 baths. There is a den in the first floor that it can be library or an office. The open concept floor plan makes it great for entertaining and family gatherings. One suite bedroom in the first floor and the master suite bedroom upstairs with a nice master bathroom with dual sinks and a large walking closet. The kitchen has beautiful granite countertops, glass cook-top and stainless appliances. Located in the heart of Windermere, Westside Village is only minutes from access to multiple lakes, dining, shopping and A-rated schools. Westside Village will also have fantastic community amenities including a resort-style pool, clubhouse, and playground. Schedule a Showing today.
Listing is courtesy of: NUMBER 1 BROKER, LLC (407-566-3400)
Listing Agent: Eric Jia (407-401-1431)
7231 SANGALLA DR, WINDERMERE, FL 34786
$1,498,00038 Days on yellowkey MLS ID: O6390817
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 3835 Built: 2011Community: Casa Del Lago-ReplatSingle Family
Remarks: Located in the gated community of Casa Del Lago in Windermere, featuring just 88 luxury homes surrounding Lake Burden, this neighborhood offers an exceptional setting near top-rated schools and only minutes from Orlando’s most popular destinations, including major highways, airports, shopping, dining, and world-renowned attractions. Built by one of the nation’s top private homebuilders, David Weekley Homes, this nearly 4,000-square-foot residence is thoughtfully designed for both everyday living and entertaining. The home features four bedrooms on the first floor, including two bedrooms positioned on the same side of the home that are connected by a shared playroom or bonus space, while each bedroom maintains its own private en suite bathroom. A formal dining room, dedicated private office, and spacious family room provide multiple areas for gathering and daily living. A convenient pool bath is located just off the main living area with direct access to the pool patio. Upstairs, a large loft-style game room offers flexible living space along with a private fifth bedroom featuring its own full bathroom, making it ideal for guests or multigenerational living. Outdoor living is equally impressive with a luxurious paver patio, screened-in pool, and low-maintenance turf backyard, creating a private retreat perfect for year-round Florida living. The home is also fully wired with a comprehensive CCTV security system featuring 21 cameras for added security and peace of mind. Residents also enjoy the prestigious opportunity to become members of the Golden Bear Club, featuring a full-service golf course and clubhouse located in the neighboring community of Keene’s Pointe. Homes in Casa Del Lago rarely come to market, making this a unique opportunity to own in one of Windermere’s most exclusive gated communities.
Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)
Listing Agent: Matt Kester (772-494-8550)
7885 BERKSHIRE OAK ALY, WINDERMERE, FL 34786
$568,00097 Days on yellowkey MLS ID: O6374875
0 Days Off yellowkey (back on 3/23/2026)
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 2214 Built: 2018Community: Westside VillageSingle Family
Remarks: Under contract-accepting backup offers. Back on the market due to the buyer failing to make the deposit; inspection was never performed. Great Schools! Beautiful 4-bedroom, 2 1/2 bathroom home in Windermere, Contemporary move-in-ready two-story home in the community of Westside Village in Windermere. Wood-look tile throughout the first floor. The kitchen features quartz countertops, an oversized island, and stainless steel appliances. The second floor features a spacious master bedroom, complete with a large walk-in closet, ensuring your desire for space and organization is fulfilled. With two full bathrooms and an additional powder room for guests, convenience and comfort are at the forefront. Thoughtfully planned, the second floor also boasts a laundry room complete with a washer & dryer. The 2-car garage has a rear entry. Community amenities include a pool and playground. Westside Village is located in the heart of Windermere and within minutes of multiple lakes, dining, and a short distance to all major attractions, including Disney, Universal, and SeaWorld. Westside Village is a sought-after community with state-of-the-art amenities, amazing a clubhouse, resort-style pool, and playground.
Listing is courtesy of: U S GLORY REALTY (407-222-7801)
Listing Agent: Rui Gao (407-222-7801)
606 E 6TH AVE, WINDERMERE, FL 34786
$2,350,00038 Days on yellowkey MLS ID: O6390327
Bed: 4 Bath: 4.5 Liv Area Sq Ft: 4471 Built: 2016Community: DiamondheadSingle Family
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)
5001 LATROBE DR, WINDERMERE, FL 34786
$3,499,99939 Days on yellowkey MLS ID: O6389183
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 4417 Built: 1990Community: IsleworthSingle Family
Remarks: One or more photo(s) has been virtually staged. Don’t miss this rare opportunity to own a stunning estate home in the prestigious Isleworth Golf & Country Club, perfectly positioned on a quiet cul-de-sac along the 6th fairway with serene views of Lake Bessie. Offering 4,417 square feet of refined living space, this elegant two-story residence features five spacious bedrooms, four-and-a-half baths, and timeless designer finishes throughout. Rich mahogany floors, soaring ceilings, and dual fireplaces create a warm yet sophisticated ambiance, while the gourmet kitchen impresses with custom cream cabinetry, a Viking gas range with French hood, double islands, and three ovens—ideal for entertaining. The seamless indoor-outdoor flow leads to a covered, screened-in patio with a summer kitchen, a resort-style heated pool, and an open-air travertine courtyard, perfect for enjoying Florida evenings. The first floor hosts two luxurious bedroom suites, including a private owner’s retreat with vaulted wood-beam ceilings, spa-like bath, and custom walk-in closets, while three additional bedrooms upstairs include a flexible guest or in-law suite with private entry. A three-car garage and expansive paver driveway provide ample parking. Experience luxury living, breathtaking golf and lake views, and the unmatched lifestyle of Isleworth—schedule your private showing today.
Listing is courtesy of: Q BOUTIQUE SPECIALTY REALTY INC (407-863-7965)
Listing Agent: Laura Diss (407-388-4103)
7264 BACKWOODS TRL, WINDERMERE, FL 34786
$650,00051 Days on yellowkey MLS ID: O6387913
3 Days Off yellowkey (back on 3/23/2026)
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 2214 Built: 2017Community: Ashlin Park Ph 2Single Family
Remarks: Under contract-accepting backup offers. Backwoods Trail, a beautifully designed 4-bedroom, 3-bathroom home that perfectly blends modern style with everyday comfort. The bright open-concept floor plan creates an inviting space ideal for both relaxing and entertaining. At the center of the home is a stunning chef’s kitchen featuring crisp white cabinetry, stainless steel appliances, designer backsplash, and an oversized quartz island with seating, seamlessly flowing into the spacious living area highlighted by a custom designer accent wall and media center. The generous primary suite offers a peaceful retreat, while the additional bedrooms provide flexibility for family, guests, or a home office. Step outside to enjoy a fully fenced backyard and an expansive screened-in lanai with paver flooring, offering the perfect space for entertaining, relaxing, or creating your own private fitness or outdoor lounge area. Conveniently located near shopping, dining, and major roadways, this home offers the perfect combination of style, space, and functionality. Don’t miss the opportunity to make this exceptional home yours.
Listing is courtesy of: NOVA REAL ESTATE SERVICES INC (407-592-1744)
Listing Agent: Lafayette Britto (407-493-2575)
12941 WESTSIDE VILLAGE LOOP, WINDERMERE, FL 34786
$929,900141 Days on yellowkey MLS ID: O6363541
Bed: 5 Bath: 3.5 Liv Area Sq Ft: 3717 Built: 2018Community: Westside VillageSingle Family
Remarks: Experience the elegance of Westside Village in Windermere, where timeless design meets modern luxury. This five-bedroom, four-bath residence spans 3,717 square feet of thoughtfully designed living space, built in 2018. The foyer welcomes you with porcelain tile floors, vaulted ceilings, and chandelier lighting that set a tone of quiet sophistication. French doors open to a versatile home office, while the formal dining room with tray ceiling creates the perfect setting for gatherings. The open-concept great room connects seamlessly to the chef's kitchen featuring a butler's pantry, premium finishes, and expansive sightlines. Enjoy peaceful water and fountain views, or open the sliding glass doors to the covered lanai, ideal for relaxing under the Disney fireworks. The owner's suite offers a serene retreat with natural light, spa-inspired bath with soaking tub, dual vanities, and a spacious walk-in closet. Upstairs, a generous loft provides flexible living for media, games, or study, while each bedroom includes a walk-in closet with a private sink. Designed for efficiency and comfort, this home features dual AC systems, a whole-house dehumidifier, and dual-pane storm windows. Residents enjoy resort-style amenities a community pool, walking trails, and parks within the sought-after Windermere school district, just minutes from dining, shopping, and Disney.
Listing is courtesy of: CENTURY 21 CARIOTI (407-566-0555)
Listing Agent: Keren Reyes (407-219-0105)
11339 CAMDEN PARK DR, WINDERMERE, FL 34786
$1,490,00050 Days on yellowkey MLS ID: O6388110
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 3492 Built: 2004Community: Keenes PointeSingle Family
Remarks: Luxury Pond-View Home in Keene’s Pointe – Windermere Located in the highly sought-after gated golf community of Keenes Pointe, this beautiful 5-bedroom, 4-bathroom residence offers an exceptional combination of space, comfort, and scenic surroundings. The home features a thoughtfully designed floor plan with a private den/office, formal living and dining rooms, and expansive living areas perfect for both everyday living and entertaining. Large windows and sliding doors allow natural light to flow throughout the home while showcasing the peaceful pond views. The spacious kitchen opens to the family room and overlooks the outdoor living area, creating the perfect setting for gatherings and family time. Step outside to enjoy your private screened pool and spa, ideal for relaxing while enjoying the tranquil waterfront setting. Additional highlights include: 5 spacious bedrooms 4 full bathrooms Private den / home office Formal living and dining rooms 3-car garage Beautiful pond views Private pool and spa Brand new roof (2024) Situated in the prestigious Keenes Pointe community, residents enjoy 24-hour guard-gated security, tree-lined streets, and proximity to world-class golf, shopping, dining, and top-rated schools. This is a rare opportunity to own a spacious home with water views in one of Windermere’s most desirable communities.
Listing is courtesy of: AMERICAN HORIZONS REALTY (407-466-0256)
Listing Agent: Martonio Pinto (407-466-0256)
6569 CRESTMONT GLEN LN, WINDERMERE, FL 34786
$985,00037 Days on yellowkey MLS ID: O6390271
1 Days Off yellowkey (back on 3/22/2026)
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 3080 Built: 2002Community: Glenmuir 48 39Single Family
Remarks: Under contract-accepting backup offers. Located in the gated community of Glenmuir, this beautifully renovated 3,080 SF pool residence offers 4 bedrooms + office and 3.5 bathrooms on an over 1/3-acre lot. Thoughtfully designed with both elegance and everyday functionality in mind, the home features a highly desirable split floorplan and seamless indoor-outdoor living. Upon entering, a welcoming foyer introduces the home’s meticulously finished interiors. A private office at the front of the home overlooks the front patio, providing an ideal space for work or study. Just beyond, the formal dining room, eat-in kitchen nook, kitchen, and family room flow effortlessly together, creating an open yet well-defined layout suited for both daily living and entertaining. Wood-look tile flooring runs throughout the main living areas, complementing the home’s neutral palette and elevated design selections. The fully reimagined chef’s kitchen features floor-to-ceiling cabinetry, a sizable center island with additional storage, a custom hood over the cooktop, double pantry closets, and a dedicated bar area. Designer lighting from Visual Comfort and Restoration Hardware enhances the main living spaces, adding warmth and refinement. Large windows and multiple sliding glass doors flood the home with natural light while providing direct access to the lanai and pool area, creating a seamless connection between indoor and outdoor spaces. The primary suite serves as a private retreat, thoughtfully renovated with transitional finishes, natural stone-looking porcelain tile, and a custom-designed closet. Additional conveniences include a spacious, light-filled laundry room with warm cabinetry and a utility sink. The secondary bedrooms are well-positioned within the split floorplan and enjoy convenient access to private bathrooms. Step outside to your private outdoor oasis, featuring a deep rear patio, sparkling pool, and privacy fence, ideal for relaxing or entertaining. Ideally located, the home offers easy access to Central Florida’s premier attractions, including the back entrance to Walt Disney World, Disney Springs, Universal Orlando, CityWalk, SeaWorld, ICON Park, and the renowned dining destinations along Restaurant Row. If you are looking for a renovated home with space, style, and an exceptional location, this outstanding Glenmuir property truly checks all the boxes.
Listing is courtesy of: THE AGENCY FL (407-335-4119)
Listing Agent: Kimberly Gilbert (407-820-6877)
13339 ROSKIN LN, WINDERMERE, FL 34786
$680,000105 Days on yellowkey MLS ID: S5141148
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 2947 Built: 2012Community: Lake Sawyer South Ph 01Single Family
Remarks: Welcome to an exceptional opportunity in one of Central Florida’s most sought-after community, WINDERMERE. Sellers need to sell and are offering closing help! This ginormous 4 bedroom, 2.5 bath, two story home offers 2,947 square feet of versatile living space designed for comfort, entertaining, and everyday luxury. The layout is ideal, featuring a private den/office, a massive upstairs loft, and generously sized bedrooms throughout. The primary suite is a true luxury retreat, impressively oversized with room to relax, unwind, and recharge. Every room offers abundant space, perfect for families, remote work, or multi-generational living. Step outside to a fully fenced backyard oasis, complete with an outdoor kitchen and brick oven!!! ideal for entertaining, weekend gatherings, Pizza Nights, and Florida-style living year-round. Located in a highly desirable neighborhood with low HOA fees and NO CDD, this home is zoned for top-rated schools, including Windermere High School. Enjoy the convenience of being less than 15 minutes from Disney World, major attractions, world-class dining, shopping, and entertainment all while still tucked away in a peaceful residential setting. An added bonus: SOLAR PANEL HOME providing energy efficiency, lower utility costs, and long-term savings, an increasingly valuable feature for today’s buyers. Homes of this size, location, and value are rarely available. Centrally located, spacious, and priced to move, this is an outstanding opportunity to own in the Windermere area. Schedule your private showing today, this one will not last! Interior painting in progress. Professional photos coming this week!!
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Karla Price (407-761-7764)
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