Location: Windermere
Do Not Show Listings
5538 W LAKE BUTLER RD, WINDERMERE, FL 34786
$3,495,00084 Days on yellowkey MLS ID: O6376859
Bed: 6 Bath: 5.5 Liv Area Sq Ft: 6000 Built: 1982Monthly Fee: $67 Tax: $25,546 (2025)Community: Kelso On Lake ButlerSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$25,546
Elementary School: Windermere Elem
High School: Windermere High School
Tax Year: 2025
Middle School: Bridgewater Middle
Remarks: Welcome to 5538 W Lake Butler Road—an expansive, newly renovated estate set on 1.9 acres of lush, lakefront land in arguably one of Central Florida’s most coveted locations, Kelso on Lake Butler. What distinguishes this property is its remarkable dual lake access. Your own private boat dock provides direct skiable waterfront on Lake Davis, while exclusive community privileges grant you gated access to Kelso's private boat ramp on the prestigious Butler Chain of Lakes. This convergence of private waterfront with chain-of-lakes connectivity creates unparalleled boating and recreational opportunities found in few lakefront estates. The expansive grounds and recent outdoor enhancements create an entertainer's paradise that is second to none! A newly upgraded outdoor bar and grill area, resort-caliber pool and spa, and sweeping lawn frame breathtaking sunset views over the water. Boasting 6 bedrooms, 6 bathrooms, 3 car garage, and more than 6,000 square feet of living space, this custom estate offers privacy, scale, and unforgettable lakefront views from nearly every room. From the moment you arrive, the chic coastal architecture, circular drive, and sprawling presence command attention. Step inside to dramatic 25-foot ceilings in the living room with a two story stacked stone fireplace and walls of glass that dissolve the boundary between interior luxury and lakefront beauty. An adjacent sun-filled flex room provides tranquil views of Lake Davis, while the completely remodeled chef's kitchen, with its oversized island, custom cabinetry, high end appliances, adjacent indoor bar and generous family room, is designed for both intimate moments as well as large scale entertaining. The main level's thoughtfully designed primary suite offers serene seclusion with a private sitting area, spa-inspired bathroom, and expansive walk-in closet, complemented by a convenient main-floor office. Upstairs, five additional oversized bedrooms, a versatile loft, dedicated gym, and stunning rooftop deck provide space for every lifestyle need. Recent upgrades give you the ultimate peace of mind, including upgraded lighting throughout, a new roof with GAF Golden Pledge 20 year workmanship warranty, three newer A/C units, updated water heater, Hayward pool heater, new dock motor, new sprinkler system with a lake-fed pump, and a transferable Massey termite bond. Minutes from Disney's back gates, top-tier schools, and Windermere's celebrated shopping and dining, yet completely private and serene—this is lakefront living without sacrifice. Your Kelso compound awaits!
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Julie Bettosini, Pa (321-689-9594)
8351 BOWDEN WAY, WINDERMERE, FL 34786
$1,199,00026 Days on yellowkey MLS ID: O6393659
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2599 Built: 2001Monthly Fee: $283 Tax: $8,252 (2025)Community: Keenes PointeSingle Family
Taxes:$8,252
Remarks: Nestled within the highly acclaimed guard-gated community of Keene’s Pointe, this completely remodeled Windermere home offers a 4-bedroom, 3-bathroom estate that showcases timeless architectural details, curated modern finishes, and a seamless indoor-outdoor luxury lifestyle. Step inside to discover a light-filled open layout with tall coffered ceilings, custom-laid wood tile flooring, formal dining, family room, and separate sitting area, all anchored by a gourmet chef’s kitchen featuring quartz countertops, premium stainless steel appliances, and custom cabinetry—effortlessly flowing into expansive living and dining spaces ideal for both everyday comfort and refined entertaining. The luxurious primary suite offers a tranquil retreat with a sitting area, a spa-inspired en-suite bath, and a spacious walk-in closet. 2 of the additional bedrooms are split from the main suite, providing comfort and flexibility with a jack-n-jill bathroom. While a separate 4th bedroom is set apart from the others and can be used as a guest suite or office, it's in a perfect space for remote work or study. Outside, your private oasis awaits—a covered lanai overlooks a sparkling pool and lushly landscaped backyard, creating a serene setting for alfresco dining or lounging under the Florida sun. This residence is also zoned for A-rated schools, within minutes of Windermere’s charming shops, fine dining, and world-renowned attractions. (Roof Replace 2026). This exceptional home invites you to experience the very best of Central Florida living. Schedule your showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Sharon Brandt (407-310-3623)
12121 SILVERLAKE PARK DR, WINDERMERE, FL 34786
$509,00042 Days on yellowkey MLS ID: O6388109
0 Days Off yellowkey (back on 3/28/2026)
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 2035 Built: 2013Monthly Fee: $33 Tax: $7,699 (2025)Community: Windermere Trls Ph 1Single Family
Taxes:$7,699
Elementary School: Bay Lake Elementary
Middle School: Horizon West Middle School
Remarks: Under contract-accepting backup offers. Enjoy over $35,000 in upgrades in this beautiful Windermere subdivision! This CORNER LOT home is move-in ready with FRESH INTERIOR AND EXTERIOR PAINT * REPLACED CARPETING * RENOVATED SECOND BATHROOM SHOWER * KITCHEN QUARTZ COUNTERTOP * APPLIANCES REPLACED * WASHER AND DRYER INLUDED * WATER SOFTENER/FILTRATION SYSTEM and more! Experience the bright and inviting atmosphere from the moment you enter. The updated kitchen features elegant quartz countertops, stainless steel appliances, and provides the perfect space for cooking, gathering, and entertaining. The secondary upstairs full bathroom has been updated with a newly renovated shower, offering a spa-like retreat within your own home. Additional upgrades include a water softener system, adding comfort and convenience to everyday living. This home is close to theme parks, major roadways, shopping, dining, and top area attractions! You'll enjoy the ideal balance of peaceful neighborhood living and easy access to everything Central Florida has to offer. From its stylish upgrades to its prime location, this home delivers exceptional value and comfort. Come experience everything this spectacular home has to offer!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Amy Moline (407-506-7447)
5036 LATROBE DR, WINDERMERE, FL 34786
$4,900,000201 Days on yellowkey MLS ID: O6346003
1 Days Off yellowkey (back on 3/28/2026)
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 5548 Built: 1990Monthly Fee: $1,224 Tax: $17,326 (2024)Community: IsleworthSingle Family
Taxes:$17,326
High School: Olympia High
Tax Year: 2024
Middle School: Chain of Lakes Middle
Remarks: Within the gates of the renowned Isleworth Golf & Country Club, this beautiful lakefront estate captures the essence of timeless luxury and gracious living. Poised on the shores of Lake Bessie, the 5,548 square-foot residence unfolds across two levels, designed to frame sweeping water views and create effortless spaces for both grand entertaining and quiet retreat. The upper level greets guests with custom French entry doors that flow into the open formal living and dining rooms, perfectly designed for gatherings. The kitchen is spacious and inviting, offering casual dining and seamless access to the main living areas. A richly appointed library adds warmth and refinement, while two en-suite bedrooms complete this floor, including the primary suite. With its oversized windows capturing endless lake vistas, a large sitting area, exterior balcony, and an en-suite bath featuring dual vanities, a soaking tub, and walk-in shower, the primary suite is a sanctuary of light and serenity. On the lower level, the estate offers two expansive bonus areas joined by a well-equipped kitchenette. Ideal for gaming, entertaining, or working from home, both spaces connect effortlessly to the sun-drenched pool terrace—seamlessly integrating indoor luxury and outdoor living. A stunning mature oak tree anchors the property's beautiful lakefront grounds, stretching gracefully toward the water’s edge—a signature of the property’s natural beauty. Beyond the oak tree, Lake Bessie shimmers in full view, offering a breathtaking backdrop to the estate. A rare combination of elegance, versatility, and iconic setting, this residence presents a lifestyle within one of Central Florida's finest communities.
Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)
Listing Agent: Monica Lochmandy (407-230-6888)
13106 ORANGE ISLE DR, WINDERMERE, FL 34786
$815,000135 Days on yellowkey MLS ID: O6361057
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 3312 Built: 2022Monthly Fee: $95 Tax: $11,893 (2025)Community: Sanctuary/Lks/WindermereSingle Family
Taxes:$11,893
Elementary School: Sunset Park Elem
Remarks: Explore the WINTERSET model from Ryan Homes of the Sanctuary at Lakes of Windermere, a corner unit, this 5- bedroom, 4.5 bathroom in Windermere combines the modern elegance, and a touch of magic with its a DISNEY Fireworks view, offering a lifestyle of unparalleled comfort. Upon entering, you are greeted by those who appreciate a dedicated workspace, the home includes a spacious office and a serene atmosphere, allowing for maximum productivity while working from home. The expansive living room boasts soaring ceilings, allowing natural light to cascade through the large windows, creating an airy and inviting ambiance. The gourmet kitchen is a chef's dream, featuring stainless steel appliances, a large cabinetry, and a spacious island with granite countertops. The adjacent formal dining room is perfect for hosting intimate gatherings or grand dinner parties. The master suite is offering a sanctuary of tranquility, a enormous shower, and dual vanities. Each of the remaining four bedrooms is generously sized, providing comfort and privacy for family and guests. The highlight of the outdoor space is the breathtaking view of the nightly Disney fireworks display, visible from the comfort of your own home. This feature creates a magical atmosphere and makes every evening a celebration.
Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)
Listing Agent: Victor De Oliveira (321-393-2772)
6109 ORTA CT, WINDERMERE, FL 34786
$4,495,00097 Days on yellowkey MLS ID: O6374125
1 Days Off yellowkey (back on 3/27/2026)
Bed: 5 Bath: 6.0 Liv Area Sq Ft: 5895 Built: 2016Monthly Fee: $442 Tax: $65,510 (2025)Community: WaterstoneSingle Family
Taxes:$65,510
Remarks: Under contract-accepting backup offers. Within the gates of the Waterstone community, this exceptional lakefront estate offers approximately 5,895 square feet of refined living space, seamlessly blending modern elegance with timeless sophistication. The thoughtfully designed floor plan features five bedrooms, five full bathrooms, and two half bathrooms, with the primary suite conveniently located on the main level. At the heart of the home is an expansive gourmet kitchen appointed with premium Thermador appliances and granite countertops, perfectly balancing form and function. The kitchen opens effortlessly to the grand family room, creating an ideal setting for both everyday living and entertaining. Soaring ceilings and clean, contemporary finishes throughout the residence underscore the home’s elevated design. Additional highlights include a dedicated wine room, ideal for showcasing a curated collection, and a private office suite that offers a quiet, productive retreat. Outdoor living is equally impressive, featuring a resort-style pool and spa, an outdoor kitchen, and a fireplace—designed for year-round enjoyment. Set on a generous 2.16-acre cul-de-sac lot, the property offers sweeping views of the ski-able Lake Cypress and includes a private dock capable of accommodating jet skis, delivering a truly exceptional waterfront lifestyle.
9508 WINDY RIDGE RD, WINDERMERE, FL 34786
$30,000,00036 Days on yellowkey MLS ID: O6388674
Bed: 7 Bath: 13.0 Liv Area Sq Ft: 51000 Built: 2011 Tax: $162,563 (2024)Community: N/ASingle Family
Taxes:$162,563
Elementary School: Thornebrooke Elem
Middle School: Gotha Middle
Remarks: Presenting Windy Ridge Estate on 18 gated acres with 614 feet of pristine frontage on Lake Down, Butler Chain of Lakes. Manicured grounds, panoramic water views, and over 50,000 SF across multiple structures create an unrivaled lakefront compound. The walled entry opens to a grand foyer with a floating mahogany staircase, marble floors, paneled walls, and Murano chandeliers. An art gallery leads to a spacious living room featuring rich mahogany millwork and expansive lake vistas. Gourmet kitchen: salamander, dual double convection ovens, commercial icemaker, full-size refrigerator, and freezer. The main level includes one of two owners' suites, plus a library-lounge or a possible sixth bedroom. Dual staircases or a Thyssenkrupp elevator provide access to the upper level, which features four-bedroom suites, including the primary retreat. An 85-foot parlor with 20-foot ceilings, built-in bookshelves, and a wet bar provides a dramatic entertaining space. Screened porch captures southern lake views and Disney fireworks. Breezeway connects to a 5,600 SF rustic lodge with a bar, catering kitchen, entertainment hall, and locker facilities. Outdoor amenities: Junior Olympic pool, spa, decorative fountain, architectural lighting, direct lake access. Additional structures include a 4,000 SF paneled garage with 20-foot ceilings, an office, and a guest apartment; a 3,800 SF storage building; three separate garages accommodating motor coach and car collection; and staff quarters with a private courtyard. A rare fusion of Georgian grandeur, lakefront serenity, and equestrian potential—crafted for those who demand the extraordinary.
Listing is courtesy of: DOUGLAS ELLIMAN (305-695-6070)
Listing Agent: Christine Gelman (561-723-4545)
505 JENNIFER LN, WINDERMERE, FL 34786
$2,250,00054 Days on yellowkey MLS ID: O6384643
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 3525 Built: 1989Monthly Fee: $333 Tax: $7,624 (2024)Community: Windermere OaksSingle Family
Taxes:$7,624
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
$1,250,00027 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
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
$2,175,000196 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
$1,019,99088 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)
9225 MCDAVID CT, WINDERMERE, FL 34786
$835,00039 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
$1,899,924137 Days on yellowkey MLS ID: O6365656
2 Days Off yellowkey (back on 3/25/2026)
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
$875,00029 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
$670,000260 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
$650,00033 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)
6846 HELMSLEY CIR, WINDERMERE, FL 34786
$609,000183 Days on yellowkey MLS ID: O6342692
Bed: 5 Bath: 3.0 Liv Area Sq Ft: 2555 Built: 2009Community: Preston SquareSingle Family
Remarks: Under contract-accepting backup offers. NEW ROOF! Welcome to 6846 Helmsley Circle in beautiful Windermere, FL! This stunning 5-bedroom, 3-bathroom home is situated on the largest lot in the neighborhood, offering over a quarter-acre of space with two expansive backyards. Imagine the possibilities—perhaps a pool or even a pickleball court! The home boasts two primary suites, one conveniently located on the main floor and another upstairs, catering to versatile living arrangements. Spanning 2,555 square feet, the interior is both spacious and inviting. The open kitchen, equipped with stainless steel appliances, seamlessly connects to a kitchenette opening up to a large family room, perfect for entertaining. In addition to the second primary suite upstairs you will find a spacious loft versatile for your needs. You won't find any carpet in this home, upgraded tile and LVP throughout. Outside, relax on the porch with peaceful views or take advantage of the community's amenities. Rear loaded attached garage! Located in Horizon West, this home offers pond and conservation views right from the front, all while being just a stone's throw away from Disney, retail, shopping, and dining. This listing is a must-see for anyone looking to embrace modern living with ample outdoor space! Come make this yours.
Listing Agent: Nickolas Amburgey (407-864-7622)
6613 MERRICK LANDING BLVD, WINDERMERE, FL 34786
$675,00030 Days on yellowkey MLS ID: O6391719
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 2641 Built: 2014Community: Vineyards/Horizons West Ph 1BSingle Family
Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained 3-bedroom, 3.5-bath home designed with comfort, functionality, and style in mind. From the moment you step inside, you’ll appreciate the seamless open-concept layout that effortlessly connects the living, dining, and kitchen spaces, perfect for both everyday living and entertaining. The kitchen is a true centerpiece, featuring granite countertops, stainless steel appliances, generous cabinetry, and upgraded Kohler fixtures. Throughout the home, you’ll find thoughtful features including luxury vinyl plank flooring in all bedrooms and energy-efficient LED lighting with many dimmer switches. Upstairs, a versatile loft area offers additional living space with the potential to convert into a fourth bedroom. The spacious primary suite provides a relaxing retreat, complete with a well-appointed ensuite bathroom and custom Closet maid organizers. Every bedroom includes built-in closet systems for optimal storage. Step outside through elegant French doors to a screened-in lanai overlooking a large, fully fenced, and professionally landscaped backyard, ideal for enjoying Florida living year-round. The home is also equipped with built-in speakers in the main living area, loft, and lanai, making it perfect for a home theater or entertainment setup. Additional highlights include a rare 3-car garage (one of only three in the neighborhood) with four heavy-duty overhead storage racks, a Culligan Gold Series water softener, whole-house surge protection, foam block insulation for added efficiency. Ideally located just blocks from Windermere High School and minutes from shopping and dining in Summerport and Winter Garden Village, this home also benefits from an HOA that covers lawn care, tree trimming, and fertilization. Residents enjoy access to two community pools and well-maintained surroundings. Don’t miss your opportunity to own this exceptional home, schedule your private showing today!
Listing is courtesy of: THE AGENCY FL (407-335-4119)
Listing Agent: Andy Neal (407-619-3517)
12989 WESTSIDE VILLAGE LOOP, WINDERMERE, FL 34786
$655,00036 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)
13048 LAKE ROPER CT., WINDERMERE, FL 34786
$1,950,000222 Days on yellowkey MLS ID: O6342354
Bed: 5 Bath: 3.5 Liv Area Sq Ft: 4130 Built: 2002Community: Windermere PointeSingle Family
Remarks: Back on the market. Unmatched Value! The only Windermere lakefront home with boat access available under $2M. Don't miss this opportunity. Enjoy the e evenings to a breathtaking sunset at your own private lake in this stunning custom-built home. Land: 1.6 acres including lake portion with 135 feet direct lake frontage. Lake Roper is renowned for its water sports, water skiing, jet skiing and fishing only acceded by the surrounding houses (No Public Ramps). This is one of the largest lots in the community. Location: Only minutes from Winter Garden Village and Downtown Windermere, minutes from main roads like 429 and 408 and a short distance from Theme Parks and Shopping Areas. Great School District. Kitchen: Totally renewed, custom-built cabinetry, high-end stainless still appliances, built in induction cook top, built in microwave and oven, huge island built with one piece of quartz, no sims. Pop-out outlets, touchless faucet and built in hood. Bathrooms: Contemporary look with porcelain tiles, quartz tops, custom made cabinetry and modern metals. Pool area: The pool was resurfaced, surrounded by new pavers overviewing the lake and a brand-new equipped summer kitchen just built. Dock: Wood dock and fishing pier with Electric Boat lift. The house was completely renovated from top to bottom including new engineering hardwood floors, 3 new A/Cs, new water heater, new irrigation system, fresh painted and new roof installed in 2020. Important Notice: "Seller is willing to accept a smaller house as part of the payment".
Listing is courtesy of: WOODSTONE INVESTMENTS LLC (407-300-4727)
Listing Agent: Fernando Teixeira (407-300-4727)
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