Location: Windermere
Do Not Show Listings
8796 PEACHTREE PARK CT, WINDERMERE, FL 34786
$949,99946 Days on yellowkey MLS ID: O6399023
REDUCED by $30,000 (3.1%) on 05/16/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3299 Built: 2014Monthly Fee: $218 Tax: $9,513 (2025)Community: Peachtree ParkSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,513
Elementary School: Bay Lake Elementary
High School: Windermere High School
Tax Year: 2025
Middle School: Horizon West Middle School
Remarks: Come live in paradise!! Minutes from the Magic Kingdom with amazing fireworks view from front porch and private pool. This exceptional builder model offers an unmatched combination of luxury upgrades, thoughtful design, and a premier location in the coveted Peachtree Park community. Perfectly positioned with conservation views and no rear neighbors, this home delivers privacy, style, and a true Windermere lifestyle. Step inside to discover custom upgrades throughout the house, including beams, shiplap accents, built-ins, and designer finishes that elevate every room. The first-floor features engineered hardwood flooring and a beautifully upgraded powder room, while the second floor offers upgraded carpet, a spacious loft with custom built-in shelving and a cushioned bench overlooking the backyard, and a fully outfitted laundry room with soft-close cabinetry and a farmhouse sink. The gourmet kitchen is a showstopper with a quartz island, open shelving, built-in appliances, a stainless steel vent hood, and a stylish backsplash. A custom cushioned bench at the kitchen table seats 8+ and stays with the home. Retreat to the luxurious primary suite featuring a custom shiplap wall, large pendant lighting, and a mounted TV, along with a spa-inspired bath offering dual vanities and a large walk-in shower. The expansive California Closets–designed primary closet is large enough to function as a second office, and the desk remains with the home. Outdoor living shines with a heated electric pool with water fountains, upgraded landscaping including a turfed backyard, bamboo and hedging for privacy, and extensive black rock accents. The pavered lanai features a motorized awning, a mounted TV, and a cedar tongue-and-groove ceiling, mirrored on the charming front porch. Professional landscape lighting enhances both the front and back yards. Insulated garage door, quiet side-winder opener, and a temperature-controlled storage closet with a keypad lock. Epoxy flooring and ceiling storage racks in the garage. Custom plantation shutters, curtains, blinds, and motorized shades. The HOA also takes care of the lawn, trees, fertilizer and hedge trimming. This home is zoned for A+ Windermere schools and offers the rare opportunity to own a meticulously upgraded, model-quality residence in one of the area’s most desirable neighborhoods.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Lee Goldberg (407-223-6965)
8179 MARITIME FLAG ST #101, WINDERMERE, FL 34786
$325,00045 Days on yellowkey MLS ID: O6399551
0 Days Off yellowkey (back on 5/16/2026)
REDUCED by $5,000 (1.5%) on 05/05/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1442 Built: 2006 Tax: $4,106 (2025)Community: Lakeside/Lks/WindermereCondo
Taxes:$4,106
Elementary School: Sunset Park Elem
Remarks: Under contract-accepting backup offers. Located just 10 minutes from Disney's Magic Kingdom and Transportation and Ticket Center, welcome to this beautifully maintained FIRST FLOOR END UNIT in the highly sought after Lakeside at Lakes of Windermere. Move in ready and thoughtfully updated, this home offers a bright, open split floor plan with high ceilings and a light, neutral palette throughout. The home has been wired with high speed fiber optic internet, and association included valet trash, sewer, and water completes living with convenience. The kitchen has been tastefully upgraded with new FRIGIDAIRE GALLERY STAINLESS STEEL appliances, including a luxury INDUCTION RANGE, complemented by 42 inch wood cabinetry, a stainless steel backsplash, pantry, and bar seating that is perfect for everyday living or entertaining. The spacious owner’s suite is filled with natural light and offers a peaceful retreat, complete with a large walk in closet and an en suite bath featuring double sinks and a garden tub and shower combo. Secondary bedrooms are generously sized with one having an ensuite/shared bathroom, and the full size laundry closet adds everyday convenience. One of the standout features is the wraparound screened in porch where you can relax and enjoy the lush landscaping and mature oak trees, plus easy access to explore the beautifully maintained grounds or go fishing on Lake Burden. The amenities here truly stand out. Residents enjoy a resort style pool, tennis courts, fishing dock to LAKE BURDEN, clubhouse with full kitchen and gathering spaces, fitness center, beach volleyball court, outdoor fireplace, walking paths, playground, and more. With assigned parking, plus plenty of guest parking, and a prime location just across the street from Publix, dining options such as My French Cafe, Piesanos Stone Fired Pizza, Boteco do Manolo, and other great dining, shopping, top rated schools, and just minutes to Orlando’s world renowned theme parks, this is low maintenance living at its best.
Listing is courtesy of: CENTURY 21 CARIOTI (407-573-2121)
Listing Agent: Chris Sartwell (321-427-7678)
9011 PINNACLE CIR, WINDERMERE, FL 34786
$2,250,00041 Days on yellowkey MLS ID: O6400872
Bed: 5 Bath: 5.0 Gar: 4 Liv Area Sq Ft: 6546 Built: 2002Monthly Fee: $172 Tax: $23,090 (2025)Community: Lake Down CrestSpa: YesSingle Family
Taxes:$23,090
Elementary School: Thornebrooke Elem
High School: Olympia High
Middle School: Gotha Middle
Remarks: Majestic and stately, this castle inspired residence sits on a 1.2 acre homesite within the privately gated enclave of Lake Down Crest. Its commanding presence is defined by patterned stone and brickwork, gabled rooflines, slate accents, wooden beams, and a shimmering grand fountain that sets an unforgettable first impression. Double front doors open to an impressive foyer flanked by formal living and dining rooms, while a step down home theater or richly paneled den—with custom built ins—creates a dramatic focal point. The well appointed kitchen features an island with prep sink, stainless appliances, gas cooktop, pantry, and a bright breakfast nook, making it ideal for both entertaining and everyday living. The inviting family room showcases a fireplace, custom millwork, and wood flooring, with French doors that lead to a Travertine patio overlooking the pool, elevated spa with waterfall, iron fencing, and paver decking. The primary retreat is a sanctuary of its own, complete with a private entrance foyer, bedroom with ceiling niche, fireplace, alcove, separate den or nursery, and a luxurious bath featuring a double headed pass through shower, jetted tub, marble topped vanities, and a spacious walk in closet. A secondary guest suite is also conveniently located on the main level. Upstairs, three additional bedrooms accompany a massive bonus room over the garage—perfect as a game room, theater, sixth bedroom, or private guest wing. A rare Florida feature, the finished basement offers exceptional flexibility for a game room, office, or substantial storage. A four and a half car drive through garage provides entrances on both sides and abundant storage. The home is nestled within an exclusive 32 residence community in East Windermere, offering top tier schools and effortless access to SR 408, downtown Orlando, I 4, Mall at Millenia, Walt Disney World, Universal Orlando, and Central Florida’s premier attractions.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Rob Rahter (407-497-4526)
9548 CROWN PRINCE LN, WINDERMERE, FL 34786
$1,450,00016 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
$2,199,00093 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
Elementary School: Windermere Elem
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. 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
$1,500,00045 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)
2219 RIDGEWIND WAY, WINDERMERE, FL 34786
$1,299,00042 Days on yellowkey MLS ID: O6400508
REDUCED by $50,000 (3.7%) on 05/04/2026
Bed: 6 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3364 Built: 1997Monthly Fee: $218 Tax: $10,027 (2024)Community: Estates At WindermereSingle Family
Taxes:$10,027
Elementary School: Lake Whitney Elem
High School: West Orange High
Middle School: SunRidge Middle
Remarks: Under contract-accepting backup offers. Set behind the gates of The Estates at Windermere—an intimate enclave of just 67 homes—2219 Ridgewind Way is the kind of property that stops you mid-scroll. A true Victorian-inspired residence, its architectural presence is unforgettable: a statement turret, wraparound porch, and intricate trim work that feels both rare and timeless in today’s market. It’s not just different—it’s irreplaceable. Inside, soaring ceilings and natural light highlight detailed millwork and thoughtfully designed living spaces that balance character with livability. The kitchen delivers where it counts—gas cooktop, stainless steel appliances, and rich wood cabinetry—anchoring both everyday life and effortless entertaining. Formal and casual spaces connect seamlessly, creating flow without sacrificing definition. The primary suite is privately positioned on the main floor, featuring a recently refreshed, spa-inspired bath. A secondary downstairs bedroom offers flexibility for guests or a true work-from-home setup, while four additional bedrooms upstairs provide the space today’s buyers are searching for. And then—the lot. Set on a rare .63 acres, outdoor living feels like a private retreat. A saltwater pool, lush landscaping, and multiple areas to unwind create a setting that’s equal parts peaceful and functional. It’s the kind of backyard that’s increasingly hard to find in Windermere. Location seals it: gated privacy just minutes from top-rated schools, parks, dining, shopping, farmers markets, hospitals, major highways and everything that makes Windermere one of Central Florida’s most sought-after places to live. Distinctive. Hard to replicate. Worth seeing in person.
Listing Agent: Hilary Hall (407-902-9311)
212 W 1ST AVE, WINDERMERE, FL 34786
$3,900,00034 Days on yellowkey MLS ID: S5148430
INCREASED by $2,300,000 (143.8%) on 05/13/2026
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3800 Built: 2026 Tax: $12,463 (2025)Community: Windermere TownSpa: NoSingle Family
Taxes:$12,463
Remarks: Pre-Construction. To be built. Positioned along the coveted Butler Chain of Lakes, this waterfront residence offers an exceptional opportunity to live in the Town of Windermere. Boasting approximately 85 feet of private frontage, The property captures sweeping views across Wauseon Bay. Permits have been approved including a 900 sf covered boat dock with lift. There are 2 primary suites, one on the 1st floor and one on the 2nd that open to a private balcony and patio respectively overlooking the water creating a serene retreat. All secondary bedrooms have lake views and balconies. Open floor plan with 2 story great room and massive windows throughout. Just moments from Windermere’s parks, tennis courts, farmers market, and private boat ramp, this home embodies the charm and lifestyle of lakefront living in one of Central Florida’s most desirable communities. ** Also listed as vacant land MLS S5147532 for $1,650,000
Listing is courtesy of: HOME WISE REALTY GROUP, INC. (407-712-2000)
Listing Agent: Eric Powell (407-720-1833)
14368 DESERT HAVEN ST #4106, WINDERMERE, FL 34786
$360,00055 Days on yellowkey MLS ID: O6396784
0 Days Off yellowkey (back on 5/14/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1840 Built: 2013Monthly Fee: $541 Tax: $3,885 (2025)Community: Oasis Cove Ii/Lakeside Village #XiSpa: NoCondo
Taxes:$3,885
Elementary School: None
High School: None
Middle School: None
Remarks: Don't miss 14368 Desert Haven St, recently enhanced with a partial flooring replacement, providing an updated surface throughout. The kitchen is equipped with stainless steel appliances for functional meal preparation. This residence includes a primary bedroom with a spacious walk-in closet, and its connecting bathroom provides double sinks and a separate tub and shower, contributing to its practical design. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
2127 LILYPAD LN, WINDERMERE, FL 34786
$1,250,00030 Days on yellowkey MLS ID: O6403899
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)
81 OAKDALE ST, WINDERMERE, FL 34786
$2,300,000195 Days on yellowkey MLS ID: S5138567
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4284 Built: 2001 Tax: $24,940 (2025)Community: Davis ShoresSingle Family
Taxes:$24,940
Remarks: Gorgeous canal-front home with direct access to the Butler Chain of Lakes and just four blocks from the heart of downtown Windermere, this 2024 luxury remodel offers the perfect blend of modern living and small-town charm. Minutes from Food Truck Fridays, local cafés, parks, tennis courts, and year-round community events, this home blends modern elegance with the warmth of small-town living. Step inside to an open, grand gathering space framed with natural wood beams, a gas fireplace, and a seamless flow into a chef-inspired kitchen. Featuring state-of-the-art GE Monogram appliances, a Taj Mahal quartzite island, restaurant-quality crushed ice, a 100+ bottle wine cooler, a full bar and coffee lounge, and a spacious walk-in kitchen pantry—this home invites effortless entertaining. Throughout, new wide-plank laminate wood floors set a refined, cohesive tone. Additional highlights include professional designer wallpaper in the dining room and powder bath, smart bidet in the primary bath, and a fully integrated smart-home lighting, shade, and security system. The primary suite is a private sanctuary, complete with a fully reimagined spa bath wrapped in marble and porcelain, a freestanding soaking tub, and two custom-designed closets. There are three more en suite bedrooms offering privacy and convenience. This corner-lot haven is framed by mature oak trees and newly installed landscaping and irrigation. A beautiful outdoor deck and built-in fire pit creates a cozy retreat for gatherings. Follow the canal behind the home to access the world-renowned Butler Chain of Lakes. The boathouse features an electric lift, dual Sea-Doo floating docks, and instant access to some of Florida’s most coveted waterways.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: David Warzycha (863-860-3365)
8180 BOAT HOOK LOOP #108/301, WINDERMERE, FL 34786
$322,000136 Days on yellowkey MLS ID: TB8465266
REDUCED by $3,000 (0.9%) on 05/14/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1442 Built: 2006 Tax: $4,422 (2024)Community: Lakeside/Lks/Windermere Ph 3Condo
Taxes:$4,422
Remarks: **$1000 Credit at Closing for Cosmetic Upgrades (with acceptable offer)!!!!**Discover the best of Windermere living in this meticulously maintained 3-bedroom, 2-bath CORNER UNIT condo in Lakeside at Lakes of Windermere. An expansive wrap-around screened porch embraces tranquil views and Florida breezes while providing an ideal space for morning coffee or evening relaxation. Inside, the open-concept layout features silestone countertops, cherry cabinets, and stainless appliances (2023 microwave, and upgraded dishwasher) lending a modern flair to the chef’s kitchen. Additional recent upgrades include a **2024 Carrier 15 SEER HVAC system** for comfort and energy efficiency throughout the year and **BRAND NEW 2025 new wood look porcelain tile** in all three bedrooms (NO CARPET). The generous primary suite and two additional bedrooms are thoughtfully separated for privacy. This floor plan features the closet OUTSIDE of the bathroom in the primary bedroom. Located just steps from the clubhouse and pool, this unit offers easy access to community amenities. Lakeside at Lakes of Windermere residents enjoy a fitness center, clubhouse and resort-style pool. The neighborhood is nestled near Lake Burden with access to a shared private dock and its own man-made lake. As a gated community, it also features a billiards room, walking paths around a central pond, and sports courts and fields. This home is just a few minutes drive from Walt Disney World (and neighboring parks) and boasts a view of the Disney fireworks EVERY night!! The combination of a well-appointed interior, wrap-around porch and enviable location near neighborhood amenities and Orlando's best entertainment make this corner-unit condo an exceptional opportunity.
Listing Agent: Erin Aaron (727-422-1688)
8866 HERENCIA ALY, WINDERMERE, FL 34786
$430,00018 Days on yellowkey MLS ID: O6407518
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1577 Built: 2021Monthly Fee: $240 Tax: $5,532 (2025)Community: Legado 95/47 Lot 100Townhouse
Taxes:$5,532
Elementary School: Castleview Elementary
High School: Horizon High School
Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bathroom home featuring a spacious loft area perfect for a home office, media room, or play space. This move-in ready property offers an open-concept layout, stylish finishes, abundant natural light, and comfortable living spaces throughout. Located in the highly desirable Windermere area, this home offers easy access to top-rated schools, shopping, dining, major highways, and Orlando attractions. Enjoy the perfect blend of comfort, convenience, and Florida living in a great location!
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Priscila Lima (321-442-7790)
13609 ANCILLA BLVD, WINDERMERE, FL 34786
$749,999107 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 Agent: Fernanda Soares Santos De Oliveira (407-840-0734)
8648 POWDER RIDGE TRL, WINDERMERE, FL 34786
$499,000131 Days on yellowkey MLS ID: O6373065
1 Days Off yellowkey (back on 5/13/2026)
REDUCED by $17,000 (3.3%) on 04/13/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1876 Built: 2014Monthly Fee: $81 Tax: $6,733 (2025)Community: Windermere Trls Ph 1CSingle Family
Taxes:$6,733
Remarks: LOCATION, LOCATION, LOCATION! Welcome to this stunning bungalow-style single-family home located in the highly sought-after Windermere Trails community—where lifestyle, convenience, and charm meet at your front door. Built by Meritage Homes (consistently ranked among the best builders in Florida), this residence features the desirable Angelou floor plan offering 3 bedrooms, 2.5 bathrooms, a spacious loft, and 1,876 square feet of thoughtfully designed living space. The open-concept kitchen and living area create a warm, inviting flow—perfect for everyday living and entertaining. Upstairs, you’ll find a versatile loft, a spacious primary suite, and two additional bedrooms with a full bathroom conveniently located between them. Wood flooring throughout the main living areas and a wooden staircase. Step outside and enjoy Florida living at its finest. From the large front porch, take in breathtaking sunsets and the Magic Kingdom nightly fireworks, while the extra-wide private balcony offers peaceful sunrise views. The rear-entry 2-car attached garage and low-maintenance yard provide both functionality and ease of ownership. *** Owned solar panel system (paid in full—no lease) designed to offset most or all of your monthly electric bill.*** The location is truly unbeatable. The home is walking distance to Bay Lake Elementary, as well as top-rated daycare and middle schools—offering unmatched peace of mind for families. Everyday conveniences such as grocery stores, dining, gyms, and shopping are also just steps away, including the newly opened Lakeside Village shopping plaza. Windermere Trails residents enjoy resort-style amenities including a large community pool, playground, dog park, scenic lakes and preserves, and miles of biking and jogging trails surrounded by beautiful retention ponds and local wildlife—perfect for morning walks and outdoor living.
Listing is courtesy of: NOVA REAL ESTATE SERVICES INC (407-592-1744)
Listing Agent: Renan Serretiello (407-415-7317)
606 E 6TH AVE, WINDERMERE, FL 34786
$2,350,00074 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)
7503 LAKE ALBERT DR, WINDERMERE, FL 34786
$1,650,00023 Days on yellowkey MLS ID: S5149564
3 Days Off yellowkey (back on 5/11/2026)
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4329 Built: 2015Monthly Fee: $180 Tax: $17,734 (2025)Community: Lake Burden South Phase 1Single Family
Taxes:$17,734
Remarks: 7503 Lake Albert Drive presents a beautifully renovated residence in the Lake Burden South community of Windermere. Completely renovated in 2023, the home showcases modern finishes, soaring ceilings, abundant natural light, and an open-concept layout designed for both everyday living and entertaining. Interior features include porcelain tile flooring, designer lighting, updated bathrooms, a modern kitchen, and refined details throughout. The spacious floor plan offers seamless indoor-outdoor living with a stunning backyard featuring a private pool, screened enclosure, and generous outdoor living space ideal for enjoying Florida living year-round. Additional highlights include a whole-house reverse osmosis water filtration system and beautifully updated living spaces throughout the home. Conveniently located near shopping, dining, major highways, Horizon West, and Windermere area amenities.
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Mariana Haddad (858-829-7578)
2931 SUNBITTERN CT, WINDERMERE, FL 34786
$1,199,000114 Days on yellowkey MLS ID: O6378100
2 Days Off yellowkey (back on 2/26/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 4018 Built: 1985Monthly Fee: $215 Tax: $8,710 (2024)Community: Butler BaySpa: YesSingle Family
Taxes:$8,710
Remarks: Under contract-accepting backup offers. Discover the charm of the Town of Windermere, Tree City USA, where the sparkling lakes, mature tree canopies, and a quaint ambiance create an exceptional place to call home. Deeply committed to preserving its character while embracing thoughtful cultural progress, Windermere offers a vibrant community filled with playful events. Nestled within the town proper and the gates of Lake Crescent Reserve, this freshly painted, custom 4018 sf home rests on pristine a 1.06 acre lot, showcasing an outdoor oasis. Designed for seamless indoor-outdoor living, this home also features an impressive 1100 sf flex suite with a private entrance, full kitchen, sliding doors to the pool. This area is ideal for a pool party or game area, multigenerational living, private office and work area, fitness center, or other creative space that best suits your needs. From the moment you enter, you’re welcomed into the family room featuring the vaulted ceilings, a wondrous wood-burning fireplace and wet bar conveniently located by the sliding pocket doors to the pool and outdoor entertaining spaces. Overlooking a privately landscaped yard with a new firepit, this home invites you to the perfect balance of year-round entertaining and peaceful retreat, where indoor comfort meets outdoor beauty in effortless harmony. Thoughtful home design is exhibited by a split floor plan, providing flexible spaces for separate conversations, play areas, multigenerational living, or large, scale entertaining. The spacious, well-appointed kitchen features a large eat-in area, SubZero refrigerator, quartz and granite countertops, wood cabinetry, and a center island with a cooktop and countertop eating. The owner’s suite offers a luxurious, recently updated en-suite and generous walk-in closet. Take advantage of the flex-space opportunities, which include the 1100 sf private entrance suite and the expansive second-floor loft with natural light from skylights. Notable upgrades include a Gerard stone-coated metal roof, resurfaced pool, re-sealed patio deck, and oversized septic leach field. Additional features include two water heaters, three-zone HVAC, vaulted family room ceiling, a large, covered lanai with retractable sunscreens on those days you prefer a little shade, and two outdoor kitchen plumbing access points for future expansion of the outdoor living space. Located within the Town of Windermere, residents enjoy exclusive amenities, including access to tennis courts, boat ramps to the various lakes, events, food truck night, farmers market, art and holiday special events, and other exclusive Town of Windermere residents-only events, to mention a few. The recently approved project to enhance the already meaningful community, involves the development of the Windermere Ward Trail and pedestrian bridge to provide safe and convenient access for pedestrians, bicyclists, and golf carts, to safely connect to local recreational areas, businesses, and government.
Listing is courtesy of: REVEL REALTY LLC (407-876-6448)
Listing Agent: Christa Dinallo (561-702-2112)
1515 LAKE WHITNEY DR, WINDERMERE, FL 34786
$1,350,00024 Days on yellowkey MLS ID: O6405903
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3931 Built: 2005Monthly Fee: $272 Tax: $12,979 (2025)Community: Reserve At Belmere 48 23Spa: YesSingle Family
Taxes:$12,979
Remarks: Under contract-accepting backup offers. Welcome to an exceptional opportunity in the highly sought-after, guard-gated community of Reserve at Belmere in Windermere, where elegance, space, and lifestyle come together seamlessly. This beautifully designed residence offers over 3500 square feet of refined living space, featuring 5 spacious bedrooms and 5 full bathrooms, salt water pool/spa, 3 car garage and thoughtfully laid out to provide both comfort and flexibility for modern living. From the moment you arrive, you are welcomed by a custom waterfall fountain in the front yard, setting the tone for the level of detail and care found throughout the home. Inside, you are greeted by soaring ceilings, elegant finishes, and an abundance of natural light that creates a warm and inviting atmosphere. The indoor fireplace adds a cozy focal point, perfect for relaxing evenings. At the heart of the home is a spacious gourmet kitchen featuring a gas stove, ideal for those who love to cook and entertain. With a large center island, ample cabinetry, flush fridge and wine fridge with an open flow into the main living areas, this space is designed for both everyday living and hosting with ease. The bedrooms throughout the home are generously sized, each offering comfort and privacy, along with spacious closets featuring custom built-ins. The primary suite is a true retreat, complete with a custom-designed closet with built-in cabinetry, providing both luxury and functionality. In addition to the primary suite there is a second en-suite bedroom. The second-floor bonus room adds incredible versatility, featuring one of the five full bathrooms, making it an ideal space for a private en-suite bedroom, home office, media room, or guest retreat. The home features crown molding, tray ceilings in the primary and a surround sound system throughout the living areas and back patio. Step outside to your own private backyard oasis, beautifully maintained, and incredibly private. Designed for true Florida living, this space is perfect for summer pool days and year-round entertaining. Enjoy the saltwater pool and spa a fully equipped summer kitchen, and a custom outdoor fire pit, creating multiple areas to gather, relax, and entertain. The size and privacy of the yard provide a peaceful, resort-style setting rarely found. The rear yard is fully fenced. Situated on a spacious lot within this premier community, residents enjoy access to top-tier amenities including a fitness center, tennis courts and park areas. Located just minutes from Downtown Windermere, top-rated schools, dining, shopping, and major roadways, this home offers the perfect balance of privacy and convenience. This is more than just a home, it’s a lifestyle.
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Michelle Dunkley (407-908-4477)
2635 TRYON PL, WINDERMERE, FL 34786
$1,475,00026 Days on yellowkey MLS ID: O6402029
Bed: 6 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4027 Built: 1997Monthly Fee: $60 Tax: $8,425 (2026)Community: Manors At Butler BaySingle Family
Taxes:$8,425
Tax Year: 2026
Remarks: Under contract-accepting backup offers. Come tour the epitome of southern charm mixed with stately elegance located in the heart of Windermere- this beautiful colonial estate was masterfully crafted by Jim Akers and sits on an expansive 0.78 acre lot within the premier Manors at Butler Bay, offering shady oak trees within minutes of downtown Windermere and her chain of lakes. The home was custom built and showcases exceptional millwork, rich hardwood floors, and an updated chef’s kitchen featuring Viking and Thermador appliances. Warm natural light streams in through expansive window packages bracketed by plantation shutters, making the main level warm and welcoming. French doors and windows throughout the newly painted living space, breakfast room and primary suite provide sweeping views of the covered lanai and private pool in this tranquil oasis. The primary suite, with two walk in closets and a spacious bathroom with jetted tub, is on the main floor, while the second level provides an additional five bedrooms, including a versatile mini-master- perfect for multigenerational families, an au pair suite, or a flexible bonus space. An oversized side-entry 3 car garage comes equipped with built in closets, storage shelving, and car charging unit. The expansive front and back yards are unique for this neighborhood, allowing for a myriad of outdoor living options, as well as providing a sense of peace and privacy. Landscaping was recently updated after the 2026 freeze and includes one of the coveted centennial legacy trees from the town of Windermere. This gem has been well maintained, including a NEW ROOF (2021), WHOLE HOME GENERATOR with 500 gallon in ground propane tank (2023), gas fireplace remodel (2022), new AC units (2023, 2023, 2018), a built in Thermador coffee maker (2025), and a Pool Heater/Chiller (2025) that encourages swimming year round. This is truly the perfect family home- it is ideally positioned within minutes of downtown Windermere and is zoned for A rated Windermere Elementary (right around the corner). Come experience the Windermere lifestyle - a unique blend of of lake life, vibrant community, and small town charm. Residents of this neighborhood have access to the Town of Windermere Chain of Lakes private BOAT RAMPs, and downtown Windermere, with its enchanting shopping district, farmer’s market, local restaurants and brewery, is only a short bike or golf cart ride away. With easy access to major highways, downtown Orlando, Disney World, Universal Studios, Winter Garden and Restaurant Row, as well as two major hospitals, are all just minutes away. Don’t miss this rare opportunity to own a home of this caliber in the sought-after Manors at Butler Bay. Washer/Dryer, breakfast and dining rooms light fixtures do not convey.
Listing is courtesy of: REIKI REALTY LLC (407-435-8909)
Listing Agent: Nipul Shah (407-435-8909)
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