Location: Winter Garden
Do Not Show Listings
14257 LAGOON COVE LN, WINTER GARDEN, FL 34787
$510,000167 Days on yellowkey MLS ID: O6375296
REDUCED by $30,000 (5.6%) on 06/01/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2365 Built: 2007Monthly Fee: $123 Tax: $8,178 (2025)Community: Black Lake Park Ph 02Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,178
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Welcome to this charming single-family residence in the highly desirable Black Lake Park community of Winter Garden. This well-maintained home features 4 (3 bedrooms + 1 study)and 2 full bathrooms with a functional open floor-plan that seamlessly connects living, dining, and kitchen areas — perfect for everyday living and entertaining. The spacious interior offers approximately 2,365 sq. ft. of living area on a ±8,178 sq. ft. lot with no rear neighbors and lush landscaping for added privacy. Situated in a vibrant community with amenities including tennis and basketball courts, playground, pool and outdoor recreation areas, this property is conveniently located minutes from Winter Garden Village dining and shopping, major roadways (including the 429), and top-rated schools.
Listing is courtesy of: INTERNATIONAL REAL ESTATE LLC (407-760-5150)
Listing Agent: Anahi Rosario (407-721-9777)
16098 MANGROVE RD, WINTER GARDEN, FL 34787
$559,000172 Days on yellowkey MLS ID: O6373125
1 Days Off yellowkey (back on 7/6/2026)
REDUCED by $9,000 (1.6%) on 07/02/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2472 Built: 2021Monthly Fee: $257 Tax: $5,612 (2025)Community: WaterleighSingle Family
Taxes:$5,612
Remarks: *** SOLAR PANELS TO BE PAID OFF AT CLOSING *** Presenting this move-in-ready 4 bed, 3.5 bath home in Waterleigh. The first floor features solid surface flooring throughout, an updated staircase with beautiful wood floors, and an impressive master walk-in closet with built-ins. Additionally, one guest bedroom and bathroom on the first floor provide perfect accommodations for guests. The master bedroom, along with two other bedrooms, is located on the second floor, separated by a spacious loft that grants access to a large balcony overlooking the pool and park. The resort-style community offers a stunning pool, beach volleyball, and tennis courts. Lawn care and landscaping are included in the HOA, so there's no need to worry about maintenance. The owner has invested extensively in energy efficiency, with whole-home solar panels and spray foam attic insulation. Don't let this opportunity pass you by.
Listing is courtesy of: LAKESIDE REALTY WINDERMERE INC (407-876-5575)
Listing Agent: Nicholas Leloudis (407-489-0711)
15725 SWEET LIMETTA DR, WINTER GARDEN, FL 34787
$704,9003 Days on yellowkey MLS ID: O6420557
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2571 Built: 2018Monthly Fee: $177 Tax: $9,439 (2025)Community: Highlands/Summerlake Grvs Ph 2Single Family
Taxes:$9,439
Remarks: This beautifully maintained 3-bedroom, 2.5-bath home with a dedicated office offers the perfect blend of style, comfort, and functionality. From the charming covered front porch and brick paver driveway to the impressive 10-foot ceilings, 8-foot doors, and crown molding throughout, every detail has been thoughtfully designed. The open-concept floor plan is centered around a stunning gourmet kitchen featuring a massive 12-foot granite island, 42" cabinetry, gas range, walk-in pantry, and abundant prep and storage space, making it the ideal home for entertaining and everyday living. The spacious living room is filled with natural light from oversized triple sliding glass doors that seamlessly connect the indoor and outdoor living spaces. The private primary suite offers a large walk-in closet, dual vanities, and an oversized walk-in shower, while the secondary bedrooms share a convenient Jack-and-Jill bathroom. The dedicated office with provides the perfect work-from-home space. Step outside to your backyard retreat featuring a covered lanai with brick pavers, outdoor cabinetry, refrigerator, TV area, ceiling fan, and gas hookup—perfect for year-round Florida living. Additional upgrades include a tankless gas water heater, smart thermostat, smart garage door openers, and a vinyl privacy fence. Located in the highly desirable Highlands at Summerlake community, residents enjoy resort-style amenities including a pool, tennis courts, dog park, playgrounds, sports fields, and picnic areas, all just minutes from Disney, Hamlin Town Center, shopping, dining, and top-rated schools.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Lily Lassalle (407-747-1751)
12241 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787
$1,190,00063 Days on yellowkey MLS ID: O6403198
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3693 Built: 2021Monthly Fee: $225 Tax: $12,882 (2025)Community: Encore/Ovation Ph 1Single Family
Taxes:$12,882
Elementary School: Water Spring Elementary
High School: Horizon High School
Middle School: Water Spring Middle
Remarks: Welcome to this stunning 2021-built residence in the highly sought-after Encore at Ovation community in Winter Garden, where modern elegance meets exceptional comfort and thoughtful design. This beautifully upgraded home showcases an open-concept floor plan filled with abundant natural light, soaring ceilings, and exquisite, professionally curated finishes throughout. rom the moment you arrive, you’re greeted by impressive curb appeal, lush landscaping, a charming front porch, and a grand, custom-designed entry hall that sets the tone for the home’s refined interior. Inside, you’ll find designer lighting, including high-end chandeliers and custom pendant fixtures, enhancing both the common and private living spaces. The gourmet kitchen is a true showstopper, featuring next-generation stainless steel appliances, premium cabinetry, stunning stone countertops, a spacious center island, and a large walk-in pantry, perfectly designed for both everyday living and entertaining. The seamless flow into the living and dining areas creates an inviting atmosphere for gatherings of any size. Retreat to the expansive primary suite, where the spa-inspired master bathroom offers a truly luxurious experience with oversized proportions and high-end finishes, complemented by custom-designed closets. Additional bedrooms are generously sized, offering flexibility for guests, a home office, or multi-generational living. This home also features a spacious loft, an oversized laundry room, and beautiful flooring throughout with no carpet, providing both style and easy maintenance. Step outside to your private backyard oasis, designed for unforgettable moments. Enjoy a covered summer kitchen complete with modern features and a cozy fireplace, perfect for barbecues and al fresco dining. The breathtaking pool and spa, enhanced by elegant landscaping and design, create a resort-style ambiance. A fire pit gathering area and outdoor shower complete this exceptional space, your guests may never want to leave. Additional highlights include a Tesla charger, solar panel system for significant energy savings, and a garage equipped with storage racks and ample space. Situated on a premium lot, this home truly offers it all. Ideally located near top-rated schools, shopping, dining, and major highways, and just minutes from Walt Disney World and Orlando’s world-class attractions, this move-in-ready masterpiece delivers the perfect combination of luxury, efficiency, and prime location.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Any Alves (407-455-0618)
14543 GOLDEN HARBOR LN, WINTER GARDEN, FL 34787
$525,0007 Days on yellowkey MLS ID: O6420711
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2039 Built: 2017Monthly Fee: $164 Tax: $7,337 (2025)Community: Watermark Ph 2CSingle Family
Taxes:$7,337
Elementary School: Panther Lake Elementary
Middle School: Hamlin Middle
Remarks: Welcome to this beautifully updated 3-bedroom single-family home in the watermark community of Winter Garden! This move-in ready residence features freshly painted interior walls throughout the entire home and brand new flooring on the entire second floor, including the staircase. The spacious upstairs living area is flooded with natural light and provides an open, airy feel for relaxing or entertaining. Strategically located in Horizon West area, this home provides an unbeatable combination of convenience and lifestyle: Just 0.2 miles from highly-rated Panther Lake Elementary School (8/10) 3.1 miles from Hamlin Middle School (9/10) Directly across the street from Starbucks, 7-Eleven, Walgreens, and a variety of restaurants. Only 15 minutes to Disney Magic Kingdom.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
12632 CLEAR SAPPHIRE DRIVE, WINTER GARDEN, FL 34787
$575,000Listed 07/06/2026 10:02AM MLS ID: S5152652
Bed: 4 Bath: 2.5 Gar: 4 Liv Area Sq Ft: 2148 Built: 2025Monthly Fee: $96 Tax: $2,290 (2025)Community: Osprey RanchSpa: NoSingle Family
Taxes:$2,290
Remarks: BEST PRICE IN FLAMINGO CROSSING AREA IN WINTER GARDEN, THE SELLER WILL CONTRIBUTE UP TO $ 8000 TOWARD CLOSING COST OR BUYER RATE ON FINANCING. This is an amazing Bungalow style house with 4 bedrooms and 3 bathrooms, on second floor there are 3 bedrooms, two bathrooms and area that maybe use has work-office place or Tv place, on main floor there are a guest suite, bathroom and amazing open concept Kitchen, walking closet and spacious dining and living area that face a nice open space area with a lanai completely fenced...this house is located on the very beautiful Osprey Ranch Community and few feet away from the Community Pool and social areas..
Listing is courtesy of: LA ROSA REALTY KISSIMMEE (407-930-3530)
Listing Agent: Gianni Montano (407-683-5067)
906 ALLENDALE LN, WINTER GARDEN, FL 34787
$1,765,000155 Days on yellowkey MLS ID: G5107489
REDUCED by $20,000 (1.1%) on 04/01/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3784 Built: 2023Monthly Fee: $203 Tax: $17,228 (2024)Community: Oakland Park B-2Spa: NoSingle Family
Taxes:$17,228
Tax Year: 2024
Remarks: Step into a custom residence where calmness, grace, and thoughtful design greet you from the moment you arrive. In the quiet part of community, overlooking peaceful pond views, this luxury home features an open, airy floor plan filled with natural light, upscale laminate planks throughout, large lot. The gourmet kitchen is a true centerpiece here, offering a commercial-grade hood ideal for entertaining, gas stove, Bosch appliances, pot filler, walk-in pantry, and an appliance garage. The living area flows seamlessly to the outdoors through fully retractable sliding glass doors, complemented by surround sound and custom-tinted windows for comfort and privacy. With 4 bedrooms and 3 full baths—including one with direct patio access—the layout is designed for both convenience and flexibility. One bedroom is located on the main level, while upstairs you’ll find a Jack-and-Jill setup and a spacious primary suite featuring a tray ceiling, spotlight accents, and a spa-inspired bath with walk-in shower, separate soaking tub, and a stunning built-in closet with natural light. An exceptional bonus is the private in-law suite above the garage, complete with its own kitchen, living area, bedroom, and stackable washer/dryer—perfect for guests or multi-generational living. The outdoor oasis is a destination of its own, surrounded by bamboo, olive, lime, and persimmon trees. The covered patio invites year-round enjoyment, and the fully fenced property offers privacy and space to unwind. From your backyard, you can even watch Space Shuttle launches light up the sky. Located in the highly desirable golf cart district, this home places you just a 2-minute walk from the West Orange Trail and only 3 miles from historic Downtown Winter Garden. Unbeatable location, unmatched lifestyle. Schedule your private showing today.
Listing is courtesy of: CENTURY 21 CARIOTI (407-566-0555)
Listing Agent: Jurgita Blake (407-402-4308)
1608 HIGHBANKS CIR, WINTER GARDEN, FL 34787
$699,000201 Days on yellowkey MLS ID: O6367937
REDUCED by $20,000 (2.8%) on 07/06/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2278 Built: 2019Monthly Fee: $140 Tax: $5,152 (2024)Community: Roper ReserveSingle Family
Taxes:$5,152
Remarks: Roper Reserve is a cozy gated community with a low HOA and just a few minutes from the bustling Downtown Winter Garden and the Winter Garden Village, that has shops and restaurants. This stunning Delaney model by Richmond American Homes, has been beautifully upgraded and blend's location, lifestyle and comfort. With large rooms and a versatile flex room, there is plenty of room in this home for everyone. The home features a gourmet kitchen with double ovens, gas appliances, and a tankless water heater, dual laundry rooms including one in the primary suite’s custom closet, and smart upgrades like a cyber space that fits a large desk, shelves and is lined with sound dampening tiles, it also includes extra outlets! Perfect working from home and housing electronics charging hub. Enjoy the AC garage, extra-wide brick paver driveway, UV light AC treatment, and beautifully finished bedrooms—one with sound-dampening and specialty lighting. The flex room shines with moody décor and copper ceiling tiles, while outside you’ll find a private pool, screened patio, outdoor kitchen, fruiting banana trees, and no rear neighbors for ultimate privacy. Whole house water softener, automatic window wireless window blinds. The home also features security cameras at various locations outside the home. Fiber Optics internet connection has just been installed into the community, making it very convenient for those working from home or for streaming!
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Rosa Aponte (407-375-9350)
13412 FOX GLOVE ST, WINTER GARDEN, FL 34787
$849,90098 Days on yellowkey MLS ID: G5110319
REDUCED by $43,000 (4.8%) on 04/16/2026
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3954 Built: 2005Monthly Fee: $243 Tax: $5,889 (2025)Community: Stoneybrook West Un 06Spa: YesSingle Family
Taxes:$5,889
Elementary School: Whispering Oak Elem
High School: West Orange High
Middle School: SunRidge Middle
Remarks: WOW!!! OVER $40,000 RECENT PRICE REDUCTION!! BRAND NEW AC SYSTEM INSTALLED LAST WEEK (7/2/26) Experience refined Florida living in this beautifully enhanced home located within a highly desirable golf course community. The property offers both style and peace of mind with a roof replaced just five years ago and a recently sealed and painted exterior. Inside, the home is designed for both comfort and entertainment, featuring an immersive surround sound system throughout the main level and an impressive dedicated theater/bonus space. Every detail has been curated to elevate everyday living. Step outside to your own private retreat—an exceptional backyard showcasing a custom pool and spa with a striking grotto feature, creating the perfect setting for relaxing or entertaining guests year-round. Residents enjoy access to an array of resort-style amenities, including a clubhouse with dining, fitness center, tennis and basketball courts, beach volleyball, playgrounds, and an expansive community pool. Ideally situated just minutes from world-renowned attractions like Walt Disney World, with convenient access to major expressways and premier shopping and dining destinations nearby, this home offers the perfect balance of luxury, location, and lifestyle. One or more photo(s) have been virtually staged. PLEASE REMOVE SHOES BEFORE ENTERING THE HOME!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Juli Onorata (407-864-7701)
14591 BLACK QUILL DR, WINTER GARDEN, FL 34787
$1,335,0007 Days on yellowkey MLS ID: O6420836
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4057 Built: 2016Monthly Fee: $215 Tax: $8,212 (2025)Community: West Lake Hancock EstatesSpa: YesSingle Family
Taxes:$8,212
Elementary School: Independence Elementary
Middle School: Bridgewater Middle
Remarks: Welcome to this beautifully upgraded luxury home in Hamlin, offering 4 bedrooms, a dedicated theater room, bonus room, resort-style pool and spa, summer kitchen, and putting green. Built in 2016 and meticulously maintained, this exceptional residence sits on one of Overlook at Hamlin’s most desirable homesites, featuring rare elevated conservation and water views that provide privacy and a setting unlike the typical flat Florida lot. Inside, soaring ceilings, abundant natural light, and an open-concept layout create the perfect balance of comfort and sophistication. The fully remodeled chef’s kitchen features quartz countertops, brand-new appliances, an oversized island, built-in microwave, wine refrigerator, and a stunning custom Venetian plaster hood. The spacious primary suite offers custom walk-in closets and a spa-inspired bath with luxury designer touches. Additional highlights include a dedicated movie theater with tiered seating, a large bonus room, custom laundry room, camera security system, designer lighting, and premium finishes throughout. Step outside to your own private backyard retreat featuring a screened-in pool and spa, summer kitchen with fire feature, covered outdoor living space, putting green, and breathtaking conservation views. Living in Overlook at Hamlin means enjoying some of the best amenities in the area, including a clubhouse, fitness center, resort-style pool, playgrounds, golf cart-friendly streets, and private lake access. Just minutes from Hamlin Town Center, you’re surrounded by great restaurants, shopping, and entertainment. With amazing sunsets and a prime location in the heart of Horizon West, this is a rare opportunity to own a luxury pool home in one of Winter Garden’s most sought-after communities.
Listing is courtesy of: TOP TIER RESORT REALTY (407-375-4566)
Listing Agent: Seth Flaugher (407-375-4566)
9605 LOST CREEK DR, WINTER GARDEN, FL 34787
$699,000297 Days on yellowkey MLS ID: V4944858
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2117 Built: 2021Monthly Fee: $261 Tax: $614 (2024)Community: WaterleighSpa: NoSingle Family
Taxes:$614
Remarks: Short Sale. ***SHORT SALE. ***ALL OFFERS MUST GO THROUGH SHORT SALE PROCESS WITH SELLERS LENDER FOR APPROVAL/DENIAL.** The Bellmore in Waterleigh! This elegant single-story four-bedroom, two-bath residence offers 2,984 total square feet of refined living on a premier corner lot with wooded privacy and pond access. Blending timeless design with modern upgrades, this home showcases luxury finishes inside and out. The gourmet kitchen is a centerpiece, featuring stainless steel appliances, a walk-in pantry, and an oversized island with abundant prep and seating space. It opens seamlessly to the spacious family room, creating a setting for gatherings. Designer touches include recessed wood-insert ceilings in the foyer and primary suite, a dramatic brick accent wall in the living room, upgraded lighting throughout and a striking chandelier in the foyer. The primary suite offers a custom closet organization system, while ceiling fans are thoughtfully placed in almost every room. Outdoor living rivals a private resort with a screened, heated saltwater pool and cascading waterfalls, surrounded by lush tropical landscaping. The covered lanai features a 10-foot drop-down projection screen for outdoor cinema nights, while brick pavers enhance the driveway, walkways, and patio. A 13.67-kilowatt solar system with net metering ensures energy efficiency. From the backyard, enjoy nightly views of the spectacular Disney fireworks—an unforgettable backdrop unique to Central Florida living. Optional luxury additions for additional purchase include a four-seat electric golf cart with charger, professional-grade garage storage racks and a complete home gym with free weights. Waterleigh is Winter Garden’s flagship planned community, offering two expansive clubhouses with resort-style pools, state-of-the-art fitness centers, tennis courts, miniature golf, walking trails, dog parks, community gardens and scenic lakes with fishing piers. Ideally near Disney, major highways, shopping and dining, Waterleigh combines convenience with unmatched amenities. Ranked as one of the top communities in the United States, Winter Garden is celebrated for its vibrant downtown, lifestyle amenities and exceptional quality of life—making this home a rare opportunity to own in one of the nation’s desirable areas. This one is a must-see. By appointment only. BUYER MUST ASSUME 50K SOLAR PANEL LOAN- BANK WILL NOT CONSIDER ANY OFFERS ASKING FOR BANK TO PAY OFF SOLAR PANELS. OCCUPIED- BY APPOINTMENT ONLY.
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (386-761-2172)
Listing Agent: Jennifer Matacale (386-212-9277)
12033 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787
$779,99011 Days on yellowkey MLS ID: O6418908
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2740 Built: 2026Monthly Fee: $169 Tax: $2,512 (2025)Community: Encore At OvationSpa: NoSingle Family
Taxes:$2,512
Remarks: Welcome to 12033 Encore At Ovation Way in Winter Garden, Florida! This new construction home built by M/I Homes offers 2,740 square foot of thoughtfully designed living space with 4 bedrooms and 3 full bathrooms. The functional floorplan offers versatility for a variety of lifestyles while maintaining a cohesive flow throughout the home. The home's design balances aesthetic appeal with practical functionality, creating spaces that are both beautiful and livable. This beautiful two-story home features an open-concept living space perfect for entertaining and family gatherings, a first-floor bedroom, a versatile loft space, a wrap-around front porch, an extended covered lanai, and a 2-car garage. Located upstairs off the loft, your owner's bedroom provides convenience and privacy with its en-suite bathroom and large walk-in closet. Experience the comfort and style of new construction without the wait. This move-in ready home offers the perfect opportunity to start fresh in a brand new space that hasn't been lived in before. Schedule a viewing today to experience firsthand what makes this Winter Garden home special!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Stacie Brown Kelly (407-221-4954)
15607 SYLVESTER PALM DR, WINTER GARDEN, FL 34787
$729,00043 Days on yellowkey MLS ID: O6410558
REDUCED by $20,000 (2.7%) on 07/06/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2092 Built: 2017Monthly Fee: $281 Tax: $10,040 (2025)Community: Lakeshore Preserve Ph 1Single Family
Taxes:$10,040
Remarks: Welcome to this stunning modern single-story home featuring a full CRESTRON Whole-Home Smart System, located in the highly sought-after Lakeshore Preserve community in Winter Garden. Built in 2017, this beautifully maintained residence offers approximately 2,092 square feet of living space situated on a 7,719 square foot lot. Inside, you’ll find 3 spacious bedrooms, 2 full bathrooms, and an open-concept layout that seamlessly connects the living, dining, and kitchen areas — creating the perfect space for both everyday living and entertaining. The stylish kitchen is equipped with modern appliances, including a built-in oven, cooktop, dishwasher, and disposal, along with solid surface countertops designed for both function and style. Additional upgrades and features include central heating and air conditioning, a tankless water heater, and an attached two-car garage. Residents of Lakeshore Preserve enjoy access to exceptional community amenities such as a clubhouse, resort-style pool, and recreational facilities. Offering a move-in ready lifestyle in one of Winter Garden’s most desirable communities, 15607 Sylvester Palm Drive combines modern comfort, smart-home convenience, and the ease of single-level living.
Listing is courtesy of: THE C SMITH REAL ESTATE GROUP LLC (407-705-7797)
Listing Agent: Corey Smith (407-927-0599)
20 W CREST AVE, WINTER GARDEN, FL 34787
$2,349,00018 Days on yellowkey MLS ID: O6417710
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4668 Built: 2020 Tax: $13,263 (2026)Community: Boyd-Lutz SubSpa: YesSingle Family
Taxes:$13,263
Elementary School: Dillard Street Elem
Tax Year: 2026
Middle School: Lakeview Middle
Remarks: Virtually Staged. Step into a home designed for the way you truly want to live. From its elevated concrete construction to its hurricane-rated engineering, this residence offers the rare combination of luxury, security, and effortless comfort. Natural light fills the interior, where level-5 walls, rich wood flooring, crown molding, and custom shutters create a warm, refined atmosphere. The heart of the home is the open living and kitchen area—perfect for gathering, cooking, and connecting. A gas range, pot filler, and handcrafted cabinetry make everyday meals feel elevated. Slide open the dramatic retractable pocket door and the entire space transforms into an indoor-outdoor retreat. The back porch is built for hosting: pecky cypress bar, industrial finishes, automated screens, garage-style doors, mini-split A/C, 1/2 bath, and room for everyone to unwind. The primary suite is a sanctuary of its own, offering a spa-inspired bath with dual shower heads, soaking tub, and digital controls. A custom closet and private concrete safe room add both convenience and peace of mind. With a butler’s kitchen, wine bar, dedicated office, and whole-home CAT-5 wiring, this home is designed for modern living at its finest—where every detail supports a lifestyle of ease, elegance, and connection. Upstairs, the bonus/game room and oversized balcony access create the perfect hangout zone. You won't complain about storage or closet space as most rooms have walk-in closets and the additional closets are oversized as well. Let your imagination run wild because the possibilities are endless with the finished two-story garage loft that is pre-plumbed and air conditioned! Mother-in-law suite, man cave with a golf simulator or a gym, home office or game room. Outside, the home is framed by curated Florida landscaping, gas lanterns, an architectural driveway, and a built-in heated concrete hot tub with Wi-Fi controls—ideal for quiet evenings or weekend entertaining. Fiber-cement siding, Ipe hardwood porch, impact windows, and full foam insulation ensure long-lasting beauty and efficiency. Prime location near Downtown Winter Garden’s brick-lined streets, upscale dining, boutique shopping, award-winning Farmers Market, Plant Street Market, Crooked Can, the West Orange Trail, and the historic Garden Theatre — a truly elevated lifestyle.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Lora King (407-947-7653)
14776 MAGNOLIA RIDGE LOOP, WINTER GARDEN, FL 34787
$880,00021 Days on yellowkey MLS ID: O6416354
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2876 Built: 2017Monthly Fee: $187 Tax: $11,232 (2025)Community: Orchard Hills Ph 3Spa: NoSingle Family
Taxes:$11,232
Elementary School: Keene Crossing Elementary
High School: Windermere High School
Remarks: Discover Your Dream Home in the Exclusive Orchard Hills Community! This stunning residence perfectly blends elegance, comfort, and functionality in one of Winter Garden's most sought-after neighborhoods. Featuring 4 spacious bedrooms, 3 full bathrooms, and 1 half bath, this home offers thoughtfully designed living spaces ideal for both everyday living and entertaining. At the heart of the home is a beautifully appointed gourmet kitchen, complete with a large center island, elegant granite countertops, and ample cabinetry. The kitchen seamlessly flows into the expansive open-concept living and dining areas, creating the perfect setting for gatherings with family and friends. A charming front porch welcomes you and provides the perfect place to relax and enjoy Florida’s beautiful weather. Step through the sliding glass doors and discover your own private outdoor retreat. The backyard features a spectacular covered gourmet outdoor living area and a beautiful private pool, offering the ideal space for entertaining, relaxing, and enjoying year-round outdoor living. Living in Orchard Hills means enjoying an exceptional lifestyle with resort-style amenities, including a clubhouse, fitness center, resort-style swimming pool, dog park, playgrounds, walking trails, and community events throughout the year. Ideally located, this home is just minutes from Hamlin Town Center, Winter Garden Village, top-rated schools, shopping, dining, grocery stores, and major highways, including SR-429. You'll also enjoy convenient access to world-famous attractions such as Walt Disney World and the many entertainment options that make Central Florida such a desirable place to live. This is a rare opportunity to own a beautiful home in one of Winter Garden's premier communities. Schedule your private showing today and experience everything this exceptional home has to offer!
Listing Agent: Erika Castellani (781-502-6199)
9567 MEADOW HUNT WAY, WINTER GARDEN, FL 34787
$965,0001 Day on yellowkey MLS ID: O6422408
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4305 Built: 2019Monthly Fee: $164 Tax: $9,084 (2025)Community: WatermarkSingle Family
Taxes:$9,084
Remarks: Currently occupied by tenant. Tenant will move out Jan 2027. Welcome to this beautifully upgraded 5-bedroom, 5-bathroom floorplan, where comfort meets style in the highly sought-after Watermark community. One of the bedrooms has been thoughtfully converted into a spacious media room by the original owners in 2019, but it can easily function as a fifth bedroom if needed. From the charming front porch to the shining luxury tile floors, this home is filled with elegant touches throughout. As you step inside, you’re greeted by a custom full-length glass wall in the hallway, adding depth and openness to the floorplan. The first room on the left is a fully equipped office. Adjacent is a sophisticated formal dining room with stylish wallpaper. The soaring ceilings and oversized family room are designed for both entertaining and everyday comfort, featuring stunning window treatments, a high-resolution projector, and a built-in surround sound system—perfect for cinematic nights at home. The gourmet kitchen is a chef’s dream, featuring stainless steel appliances, a large quartz countertop, a summer kitchen layout, and designer pendant lights, all of which can remain with the home. The first-floor master suite is a true retreat with blackout window treatments, a spa-like bath with a soaking tub, and a generous walk-in closet. Upstairs, you’ll find three additional bedrooms, a spacious loft, a study/den, and a one-of-a-kind themed game room with a hand-painted moon mural, cloud accents, twinkling ceiling lights, and a second surround sound system. Step outside to a covered patio with a heat-block screen and ambient ceiling lighting—ideal for evening gatherings. Located just a short walk from the luxury clubhouse and nearby commercial plaza, you’ll enjoy resort-style amenities including pool, a fitness center, fire pit, waterslides, tennis and basketball courts—all with a low HOA. This home offers the perfect combination of luxury, convenience, and community living. There are four lights have been removed compared to the original listing photos: • The fixture in the front study room • The one in the formal dining room • The light above the staircase• The one in the morning/breakfast area Please call for showing.
Listing is courtesy of: INTEREALTY SERVICE (626-328-8535)
Listing Agent: Emma Yue (626-328-8535)
13014 SUNSET GARDEN LN, WINTER GARDEN, FL 34787
$584,00086 Days on yellowkey MLS ID: O6398349
REDUCED by $3,000 (0.5%) on 06/01/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2143 Built: 2026Monthly Fee: $80 Tax: $2,326 (2025)Community: Westhaven At OvationSingle Family
Taxes:$2,326
Remarks: Under Construction. Toll Brothers New Construction at Winter Garden Horizon West. Estimate completion end of 2026. Single family Bungalow. The Montpelier home features a covered entry that leads to a spacious foyer and an expansive guest suite. The living area includes a dining room, with breakfast bar, great room, and access to the courtyard. The second-floor features 2 bedrooms and a primary suite is highlighted by a large walk-in closet and a private bath with dual vanities, separate shower, and private water closet. There's still time to personalize this home with your preferred design upgrades.
Listing is courtesy of: ORLANDO TBI REALTY LLC (407-345-6000)
Listing Agent: Dayene Grubert (863-521-4474)
13067 TOLLCROSS WAY, WINTER GARDEN, FL 34787
$599,000175 Days on yellowkey MLS ID: O6367311
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1906 Built: 2024Monthly Fee: $96 Tax: $2,239 (2024)Community: Westhaven At OvationSingle Family
Taxes:$2,239
Remarks: Located in the heart of Horizon West in Winter Garden, just minutes from the gates of Walt Disney World, this beautiful bungalow is nestled within Westhaven At Ovation, a sought-after residential community by Toll Brothers. The location is truly exceptional, offering quick and easy access to State Road 429, the Flamingo Crossings shopping and dining district, and all the magic Disney has to offer. Community amenities are conveniently located just across the way, making it effortless to enjoy the Florida lifestyle. Inside, the open floor plan is enhanced by beautiful LVP flooring throughout the main living areas on the first floor and in the primary bedroom upstairs, while the additional bedrooms feature comfortable carpet. The kitchen is a standout with crisp white cabinetry, a spacious island accented by three pendant lights, and a stylish backsplash that adds a pop of energy to the inviting neutral palette. Outdoor living is just as impressive, with a screened-in lanai plus additional uncovered outdoor space that connects to the two-car detached garage—one of the few bungalow designs with a detached garage concept, offering even more ways to enjoy Florida’s beautiful weather. WELCOME HOME!
Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)
Listing Agent: Amy Kidwell Pa (407-848-8042)
1349 CASTLEPORT RD, WINTER GARDEN, FL 34787
$720,000125 Days on yellowkey MLS ID: O6377923
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3673 Built: 2001Monthly Fee: $250 Tax: $9,122 (2024)Community: Stoneybrook West 44/134Single Family
Taxes:$9,122
Remarks: This beautiful renovated 5-bedroom home located in the guard-gated golf community of Stoneybrook West, in Winter Garden, offers two primary suites, three additional bedrooms, and a large loft/flex space, ideal for multi-generational living or a home office. New stair and loft railings have been installed to enhance safety and functionality. The open-concept floor plan features abundant natural light and a seamless layout for entertaining. Enjoy a spacious fenced backyard with room for a pool or outdoor living area. Stoneybrook West offers a boat ramp, fishing areas, and lake access for water enthusiasts, a clubhouse, fitness center, and a large resort-style community pool. Residents can enjoy tennis courts, a golf course, basketball court, a playground, and feel at ease with a 24-hour guard-gated entrance ensuring a secure and peaceful living environment with scenic walking and biking trails. Conveniently located near shopping, dining, top-rated schools, and major roadways with easy access to Orlando and area attractions. Resort-style living in a prime Winter Garden location.
Listing is courtesy of: DOUGLAS ELLIMAN (561-655-8600)
Listing Agent: Dianna Desboyaux (407-920-4601)
17059 HARBOR OAK PKWY, WINTER GARDEN, FL 34787
$620,0007 Days on yellowkey MLS ID: G5114379
REDUCED by $10,000 (1.6%) on 07/05/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2692 Built: 2017Monthly Fee: $215Community: Waterside/Johns Lake Ph 2ASingle Family
Taxes:$0
Elementary School: Hamlin Elementary
Remarks: Motivated Seller! Don't miss your opportunity with this Winter Garden home - offering elegance, convenience and affordability. Situated inside the desirable Waterside community, you will find this beautifully designed residence, blending timeless sophistication with modern comfort, offering an open floor plan, designer finishes, and exceptional indoor-outdoor living. From the moment you arrive, the charming covered front porch, mature landscaping, and inviting curb appeal set the tone. Inside, you're greeted by wide-plank luxury vinyl flooring, soaring ceilings, crown molding, and sun-filled living spaces designed for both everyday living and effortless entertaining. The gourmet kitchen is a true showpiece featuring granite countertops, an oversized center island with seating, farmhouse sink, white shaker cabinetry, stainless steel appliances, gas cooktop, double ovens, subway tile backsplash, a custom, handmade hood and designer pendant lighting. Flowing seamlessly into the spacious dining area and family room, this home is ideal for gathering with family and friends. Large sliding glass doors open to an expansive covered lanai with a stunning wood-finished ceiling, creating the perfect space to dine outdoors or just relax. The fully fenced backyard provides privacy, while maintaining a low-maintenance lifestyle. As you journey to the second level, you are greeting by a spacious loft, creating a retreat for unwinding and more closet space. Two large, additional bedrooms and a full bathroom are set off from the primary suite. Escape to your luxurious primary suite, offering a spacious walk-in closet and a beautifully upgraded spa-inspired bath, complete with a custom dual-sink vanity with quartz countertops, elegant gold fixtures, an oversized walk-in shower, and designer tile extending to the ceiling. Additional highlights include double-pane windows, custom window treatments, upgraded light fixtures, abundant storage, an oversized laundry room and pantry and thoughtful designer touches throughout. Residents enjoy outstanding resort-style amenities including a lakeside community pool, clubhouse, fitness center, playground, unfenced dog park and community dock. Ideally located in the heart of Winter Garden, this exceptional home is just minutes from shopping, dining, entertainment, theme parks, major highways, and top-rated schools. This isn't just a home; it's a lifestyle. Book your showing today!
Listing is courtesy of: ERA GRIZZARD REAL ESTATE (352-394-5900)
Listing Agent: Wendy Moore (678-575-5596)
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