Location: Winter Garden
Do Not Show Listings
18047 CIDER MILL LN, WINTER GARDEN, FL 34787
$829,99028 Days on yellowkey MLS ID: O6411900
2 Days Off yellowkey (back on 6/2/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3327 Built: 2025Monthly Fee: $200 Tax: $1,989 (2025)Community: WaterleighSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,989
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Under Construction. Waterleigh presents the Seacliff. This two-story all concrete block construction single-family home features 4 bedrooms and 3.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you are greeted with a formal dining room. Go down the hallway and you’ll find a powder room and laundry room tucked behind the stairwell leading up to the second floor. The well-appointed gourmet kitchen overlooks the casual dining area, family room and outdoor lanai. This home features a spacious kitchen island with built in sink and dishwasher to optimize counter space, and a walk-in pantry for extra storage. All homes in this community will have stainless steel appliances, making cooking a piece of cake. Bedroom one is located off the living space in the back of the home for privacy. The bedroom one bathroom impresses with separate vanities, shower/tub space, toilet room with privacy door as well as a spacious walk in closet. As we head upstairs, you are greeted with a loft area and all three bedrooms. Two bedrooms share a upstairs bathroom with double bowl vanity while the additional bedroom is complete with ensuite bathroom. Like all homes in Waterleigh, the Seacliff includes a Home is Connected smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)
Listing Agent: Stephen Cline (407-250-7299)
744 LAKE BRIM DR, WINTER GARDEN, FL 34787
$949,000108 Days on yellowkey MLS ID: O6388775
1 Days Off yellowkey (back on 5/26/2026)
REDUCED by $20,000 (2.1%) on 05/22/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2667 Built: 2016Monthly Fee: $208 Tax: $9,275 (2025)Community: Oakland ParkSingle Family
Taxes:$9,275
Elementary School: Tildenville Elem
High School: West Orange High
Middle School: Lakeview Middle
Remarks: Under contract-accepting backup offers. Perfectly positioned fronting one of Oakland Park’s picturesque green spaces, this exceptional home offers a rare opportunity to enjoy PARK-SIDE living in one of Winter Garden’s most celebrated communities. Oakland Park, a PARADE of HOMES award-winning neighborhood, is admired for its timeless architecture & inviting outdoor spaces that create a true sense of community. This beautifully designed Seaside floorplan blends classic charm with modern livability, offering 4 bedrooms, 3.5 baths, a STUDY, dining area, spacious loft, oversized garage, & FENCED yard. The primary suite is conveniently located on the main level, creating a peaceful retreat complete with a generous walk-in closet, a separate linen closet, & direct access to the laundry room, which has been enhanced with custom cabinetry for optimal storage & organization. Upstairs, the loft provides a versatile secondary living area—ideal for a media room or play space—accompanied by three additional bedrooms & two full baths, including one private en-suite. At the center of the home, the expansive kitchen is designed for both everyday living & effortless entertaining, enhanced with under cabinet lighting & tile backsplash. Abundant cabinetry & extensive counter space provide exceptional functionality, while the large island offers ample seating, making it the natural gathering place for family & guests alike. The adjoining dining area is equally impressive, featuring a dedicated buffet—perfect for hosting celebrations, holidays, or casual dinners. The home showcases rich WOOD flooring throughout the main living areas, adding warmth and sophistication, while soft carpeting in the bedrooms enhances comfort & tranquility. One of the home’s most captivating features is the inviting wraparound front porch, where French doors open to sweeping views of the beautifully maintained park. The home’s outdoor living continues in the screened rear porch, thoughtfully designed with retractable screens to maximize comfort & flexibility throughout the seasons. Beyond the porch, the backyard has been carefully curated as a private entertainment retreat. A paver patio anchors the space, complemented by a cozy FIRE-PIT, additional seating areas, & an outdoor kitchen featuring a built-in grill, mini fridge, & sink. Pet lovers will appreciate the dedicated dog area finished with low-maintenance artificial turf, creating a convenient & attractive space for four-legged family members. With its prime park-front location, versatile living spaces, & thoughtfully designed indoor-outdoor lifestyle, this home offers an exceptional blend of elegance, comfort, & community. Just a short GOLF CART ride away, you’ll find the charm and vibrancy of Historic Downtown Winter Garden, known for its award-winning restaurants, boutique shopping, outdoor dining, farmers market, & events. This is more than a home — it’s a lifestyle defined by luxury, walkability, connection, & the unmatched charm of Winter Garden living. This golf-cart-approved WATERFRONT community offers year-round activities, from golf cart parades to book clubs & social gatherings, making it an extraordinary place to call home. The community features parks, playgrounds, two pools, a clubhouse, dog park, & trails, including access to the 22 mile long WEST ORANGE TRAIL. Don’t miss this opportunity to live in one of the areas most sought-after neighborhoods, with easy access to interstate travel, shops, restaurants, golf courses, & world-renowned theme parks!
Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)
Listing Agent: Ashley Boyd (321-209-5540)
15518 HONEY MANDARIN WAY, WINTER GARDEN, FL 34787
$869,90084 Days on yellowkey MLS ID: O6396204
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3640 Built: 2018Monthly Fee: $113 Tax: $11,489 (2025)Community: Highlands/Summerlake Grvs Ph 2Single Family
Taxes:$11,489
Elementary School: Summerlake Elementary
High School: Horizon High School
Middle School: Hamlin Middle
Remarks: Stunning 5-bedroom, 4.5-bath home located in the highly sought-after Highlands at Summerlake Groves in Horizon West. Built in 2018, this spacious two-story residence offers over 3,600 square feet of living space with an open-concept layout, a gourmet kitchen with oversized island, and a large upstairs loft perfect for entertainment or a home office. The primary suite features a walk-in closet and spa-style bathroom. Conveniently located near Hamlin Town Center, top-rated schools, and major highways including 429, this home combines modern comfort with prime location.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Alexandre Zapparoli Llc (321-444-8701)
12915 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787
$594,000137 Days on yellowkey MLS ID: O6381156
0 Days Off yellowkey (back on 5/5/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2143 Built: 2026Monthly Fee: $77 Tax: $2,326 (2025)Community: Westhaven At OvationSingle Family
Taxes:$2,326
Elementary School: Water Spring Elementary
Middle School: Water Spring Middle
Remarks: Under Construction. Toll Brothers New Construction at Winter Garden Horizon West. Estimate completion July 2026. Single family Bungalow. This 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 master suite is highlighted by a large walk-in closet and a private bath with dual vanities, separate shower, and private water closet.
Listing is courtesy of: ORLANDO TBI REALTY LLC (407-345-6000)
Listing Agent: Dayene Grubert (863-521-4474)
12940 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787
$919,000137 Days on yellowkey MLS ID: O6381140
0 Days Off yellowkey (back on 2/14/2026)
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3894 Built: 2026Monthly Fee: $77 Tax: $2,326 (2025)Community: Westhaven At OvationSingle Family
Remarks: Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026. The wide and elongated foyer create an impressive entry into this home, with large formal dining room and spacious kitchen. The well-equipped kitchen features a walk-in pantry and an open view of the breakfast area and great room. The great room opens out to a covered lanai. The master bedroom/ on the second floor includes a large walk-in closet and a private bath with a free-standing tub, a separate shower with a seat, and a private toilet area. The second floor features a spacious loft, and large secondary bedrooms. The Griffin is well planned for a comfortable, luxurious lifestyle. Model home available for walkthrough.
12911 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787
$548,000142 Days on yellowkey MLS ID: O6379918
5 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2062 Built: 2026Monthly Fee: $77 Tax: $2,326 (2025)Community: Westhaven At OvationSingle Family
Remarks: Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026. This home is conducive for entertaining with its open floor plan. This home features a covered entry that leads to an open and expansive living space, kitchen, and dining. The home features covered lanai and a spacious courtyard with access to the detached 2 cars garage. The master bedroom is highlighted by a large walk-in closet and a private bath with dual vanities, separate shower, and private water closet.
16555 WINGSPREAD LOOP, WINTER GARDEN, FL 34787
$791,000300 Days on yellowkey MLS ID: O6340280
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3093 Built: 2019Monthly Fee: $120 Tax: $9,566 (2024)Community: Hawksmoor-Ph 1Single Family
Taxes:$9,566
Tax Year: 2024
Remarks: This stunning 4-bedroom, 3.5-bath residence sits proudly in the highly sought-after Hawksmoor community of Winter Garden. Designed with a modern open-concept layout and upgraded with premium finishes, this home blends elegance, functionality, and comfort. Perfectly positioned near the Orange County National Golf Center and Lodge—home to the nation’s largest driving range—this property also offers quick access to Orlando Health Hospital, brand-new top-rated schools, shopping, fine dining, and entertainment. With Highway 429 just minutes away, world-famous Orlando theme parks are practically at your doorstep. House is leased until Nov/2026 and buyer must honor the contract. Step inside and be welcomed by soaring ceilings and a bright, spacious floor plan. The luxurious primary suite with a spa-inspired ensuite is conveniently located on the main level, while the second floor offers three beautifully designed bedrooms, a bonus living/play area, and ample space for family or guests. A flex room on the first floor can serve as a home office, library, or formal dining area. At the heart of the home, you’ll find a chef’s kitchen featuring stainless steel appliances, custom 42" cabinetry, oversized granite island seating up to six, walk-in pantry, and butler’s bar connecting to the dining/flex space. Perfect for both everyday living and entertaining. Outside your door, Hawksmoor provides resort-style amenities, including a zero-entry pool with splash area, clubhouse with private rental options, fitness center, yoga lawn, Zen garden, and community walking trails around picturesque lakes and ponds. This is more than just a house—it’s a lifestyle. Don’t miss the chance to make this exceptional property your new home in one of Winter Garden’s most desirable communities.
17124 BEACHGRASS ALY, WINTER GARDEN, FL 34787
$559,99039 Days on yellowkey MLS ID: O6408024
0 Days Off yellowkey (back on 6/1/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1983 Built: 2026Monthly Fee: $112 Tax: $6,874 (2025)Community: Lake Star At OvationSpa: NoSingle Family
Taxes:$6,874
Remarks: Under Construction. Welcome to 17124 Beachgrass Alley, in Winter Garden, Florida: a new construction home built by M/I Homes, offering 1,983 square feet of thoughtfully designed living space. This home features a well-crafted floorplan combining quality design with everyday functionality. This home features 3 bedrooms, 2.5 bathrooms, an open-concept living space perfect for daily living and entertaining, a lanai, and a 2-car rear-load garage This home showcases an open-concept living space that creates a seamless flow between the family room, kitchen, and dining area, making it ideal for both relaxed evenings and hosting guests. The floorplan is designed with intention, ensuring each room serves a clear purpose while maintaining a cohesive feel throughout. Upstairs, the owner's bedroom offers a private retreat, complete with an en-suite bathroom and walk-in closet for added convenience. The overall layout reflects a commitment to quality design, with clean lines and functional spaces that make everyday living comfortable. Situated in a desirable Winter Garden neighborhood, this home benefits from proximity to parks and outdoor recreation areas, providing easy access to green spaces for families and individuals alike. The surrounding neighborhood offers a welcoming atmosphere with well-maintained streets and a sense of connection to the outdoors.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Stacie Brown Kelly (407-221-4954)
15047 GAULBERRY RUN, WINTER GARDEN, FL 34787
$1,525,00041 Days on yellowkey MLS ID: O6408283
1 Days Off yellowkey (back on 5/31/2026)
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4964 Built: 2013Monthly Fee: $198 Tax: $10,739 (2026)Community: Signature Lks-Pcl 01D Ph 02Single Family
Taxes:$10,739
Elementary School: Independence Elementary
Tax Year: 2026
Middle School: Bridgewater Middle
Remarks: Under contract-accepting backup offers. This is the one you’ve been waiting for! Tucked away on a peaceful cul-de-sac and situated on an expansive half-acre corner lot, this stunning Horizon West home, in the highly sought-after community of Independence, offers exceptional curb appeal, privacy and luxury living at every turn. Inside, experience soaring, double-height ceilings and an abundance of natural light that fills the spacious, open-concept living area. The thoughtfully designed floor plan features a private office, a formal dining room and an oversized main living space with incredible two-story ceilings and breathtaking views of the resort-style pool and outdoor entertaining areas. At the heart of the home is the chef’s kitchen, complete with extensive cabinetry and storage, a large center island and top-of-the-line stainless steel appliances, perfectly designed for both everyday living and entertaining. The spacious owner’s suite is a true retreat, featuring custom walk-in closets and a spa-inspired bath designed for relaxation. An additional main-level living space offers incredible flexibility and can easily serve as a private guest retreat or multigenerational living suite. Upstairs, entertainment takes center stage with a spacious bonus and playroom, an included pool table and an impressive, dedicated private home theater, featuring luxury powered seating for eight with a built-in projector and amazing quality in-wall surround sound for the ultimate movie-night experience. Outside, enjoy your private backyard oasis. The inviting and refreshing oversized pool showcases a stone wall spillover water feature and Baja sun shelf, all surrounded by lush landscaping for added privacy. The expansive lanai offers two separate seating areas, plus a natural gas fire pit and outdoor kitchen, creating the perfect setting for family fun and entertaining. Beyond the pool area, you’ll find more than 2,000 square feet of private, fenced backyard space with lush grass, shaded by mature trees, ideal for play, pets or relaxing outdoors. Additional upgrades include an oversized, three-car garage plus workspace, a dependable, powerful 20-kilowatt-hour Kohler whole-house generator, two tankless water heaters, a newly-upgraded HVAC and pool equipment and newer pool solar panels, all offering added efficiency and peace of mind. In a community known for its beautiful lake views, incredible scenery and abundant natural wildlife, this home also offers nightly views of Disney fireworks, spectacular sunsets over Lake Hancock and unforgettable rocket launches, all from inside and around this beautiful home. Experience this incredible home in the ideal location for yourself, and discover luxury living at its finest.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)
Listing Agent: Lynda Miller (407-620-2924)
17588 LAKE STAR RD, WINTER GARDEN, FL 34787
$1,185,000106 Days on yellowkey MLS ID: O6387269
REDUCED by $10,000 (0.8%) on 04/25/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4026 Built: 2024Monthly Fee: $84 Tax: $3,806 (2024)Community: Northlake At OvationSingle Family
Taxes:$3,806
Remarks: Step into better-than-new living with this beautifully upgraded home that rival's today's new construction--without the wait. This exceptional five-bedroom, four-bathroom home situated on Lake Star located in the highly desirable Horizon West area. The inviting entryway leads to a spacious, bright, and open-concept layout filled with abundant natural light and wood look plank tile flooring on the lower level. This Ashton Woods "Superior" floor plan has been upgraded to include a downstairs 5th Bedroom/In-law suite. The gourmet kitchen features a neutral color palette, sleek quartz countertops, lots of cabinet storage, under cabinet lighting, a white farmhouse apron front single bowl sink, modern appliances, including a stainless-steel wall-mounted vent hood, smooth surface cooktop, built-in oven and microwave complemented by a tile backsplash. An open-concept design seamlessly connects the kitchen to the expansive family room, providing an ideal space for entertaining. The first-floor primary bedroom suite offers a tray ceiling and a luxurious bath featuring double vanities, garden tub and a walk in glass framed shower with multiple headed jets. Three additional well-appointed bedrooms upstairs provide ample space for family and guests. The home also features a formal dining room, a den, and a spacious game room, offering versatile living options. A beautiful, stained oak staircase with open stair rails. Elegant finishes, including plantation shutters on all the windows and neutral tones create a timeless aesthetic throughout the residence. Outdoors, the property boasts a well-maintained exterior, and a paver driveway leading to the two-car garage. The spacious lot includes a covered lanai with plumbing already in place to create a summer kitchen of your dreams, and a scenic lakefront view, providing a peaceful and tranquil setting. The community amenities include a clubhouse, a pool, a dog walk park, and a playground, offering convenient recreational opportunities. Conveniently located near shopping, dining, top-rated schools and world-famous Orlando attractions, including Disney parks, Downtown Winter Garden and 40 minutes to the Orlando International Airport. This home is also within minutes of Florida's Western Beltway 429, providing easy access to the area's major thoroughfares. Why wait months for new construction when you can have it all--right now?
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Dee Lund (407-925-7781)
15532 AVENUE OF THE ARBORS, WINTER GARDEN, FL 34787
$1,999,94744 Days on yellowkey MLS ID: O6405850
REDUCED by $3 (0.0%) on 05/25/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3837 Built: 2016Monthly Fee: $195 Tax: $17,089 (2025)Community: Signature Lakes Ph 02 A B H I JSpa: YesSingle Family
Taxes:$17,089
Middle School: Horizon West Middle School
Remarks: .....LOCATION! LOCATION! LOCATION!.....LAKE HOME!.....PRIVATE DOCK!.....SALTWATER POOL!.....PRIMARY BEDROOM on MAIN!!!!!..... Gorgeous 5 bedroom. 4.5 bath home on Lake Hancock located in Hamlin Town Center. Upon entering, the home welcomes you with a bright, OPEN-CONCEPT design that seamlessly connects the main living areas, creating an ideal flow for entertaining and everyday living. Stunning LAKE VIEWS can be enjoyed from the gourmet kitchen, main level primary suite, additional bedroom and great room. The JUNIOR SUITE would make a wonderful mother in law suite. The UPPER LEVEL features a spacious BONUS ROOM ideal for media/game/play/home gym or secondary living area; along with FULL BATH and BEDROOM, providing flexibility and privacy away from the main living spaces. Step outside to a massive RESORT STYLE OUTDOOR LIVING AREA making it your personal oasis for both relaxation or entertaining. The expansive PAVER DECK leads to a pristine heated saltwater pool and spa. Your private dock offers the perfect setting to enjoy fishing, sunsets, and nightly Disney fireworks from the comfort of home. LAKE HANCOCK is renewed for it’s exceptional recreational opportunities, making it ideal for boating enthusiasts and avid anglers alike. The lake is well known for its excellent fishing, canoeing, paddle boarding, water skiing and wake sports. The lakes size and depth also accommodate seaplane activity. The COMMUNITY features multiple playgrounds, tennis courts, basketball, pools, fitness centers, arcade, clubhouse, dog parks, business center and CABLE/INTERNET included in HOA DUES.....Located in one of Central Florida's most sought after areas-HAMLIN TOWN CENTER, the vibrant heart of the HORIZON WEST community. The NEIGHBORHOOD offers sidewalks. paved WAKING/BIKING trails connecting to everything you need. Close walk to grocery store, dining, shopping, Cinepolis, POPSTROKE (Tiger Woods designed Putt Putt), Restaurant/Ice Cream Parlor/Playground), Urban Air Adventure & Trampoline Park. Convenient access to SR429! ***All information deemed reliable but not guaranteed and should be independently verified by the buyer***
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Tina Carroll (678-850-8036)
15591 GENTLE RAIN DR, WINTER GARDEN, FL 34787
$730,00028 Days on yellowkey MLS ID: O6411803
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2896 Built: 2025Monthly Fee: $99 Tax: $1,890 (2025)Community: Osprey Ranch Ph 1Spa: NoSingle Family
Taxes:$1,890
Remarks: Welcome to this beautifully upgraded home in Winter Garden, where style, comfort, and thoughtful design come together seamlessly. From the moment you step inside, you’re greeted by an open, bright, and airy layout, enhanced by elegant farmhouse-inspired finishes and abundant natural light throughout. The main home features no carpet, creating a clean and modern aesthetic, while stunning custom built-in cabinetry in the kitchen, living room, and bedrooms adds both sophistication and functionality. At the center of the home, the spacious kitchen is designed to impress, featuring a large island perfect for entertaining, elegant finishes, and seamless flow into the living and dining spaces. Every detail has been thoughtfully selected, and with tons of upgrades throughout, this home feels elevated at every turn. One of the standout features is the private studio above the garage, ideal for guests, extended family, a home office. Located in the desirable Osprey Ranch community, this home is just minutes from Walt Disney World and everyday conveniences. Even better, you are just steps from the resort style amenities, including the community pool, splash pad, cabana, and playground, offering the perfect blend of lifestyle, convenience, and community living.
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Carolina Fortes Ribeiro (407-956-7674)
13181 TOOLCROSS WAY, WINTER GARDEN, FL 34787
$1,100,00028 Days on yellowkey MLS ID: O6410984
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3894 Built: 2024Monthly Fee: $83 Tax: $11,946 (2025)Community: Westhaven At OvationSingle Family
Taxes:$11,946
Remarks: Located in the highly desirable Westhaven at Ovation, this exceptional five bedroom, four bathroom home sits on one of the largest lots in the community with an impressive 0.28 acres, offering extra privacy, space, and an unbeatable setting. With no front or rear neighbors and peaceful pond views behind the home, this property delivers a rare combination of comfort and tranquility. Designed with both elegance and functionality in mind, the home features a spacious open layout with a large loft, an oversized covered lanai perfect for entertaining, and a charming front porch that creates a warm welcome. The gourmet kitchen is equipped with premium KitchenAid appliances and an LG InstaView Door-in-Door refrigerator, combining luxury and modern convenience. Thoughtful upgrades can be found throughout the home, including elegant open rail stairs with luxury vinyl flooring, floor-to-ceiling tile in the bathrooms, and custom-designed spaces in the primary suite closet, laundry room, and pantry for maximum organization and style. The laundry room also includes a utility sink, adding extra practicality for everyday living. The spacious primary suite and well-distributed floor plan provide comfort for the entire family, while the proximity to the community clubhouse adds even more convenience and lifestyle appeal. With a two car garage, exceptional finishes, and one of the best locations in the neighborhood, this home is truly a standout opportunity in Winter Garden.
Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)
Listing Agent: Roberta Do Nascimento Ferreira Voto (407-346-9720)
15197 BLUE PEACOCK LN, WINTER GARDEN, FL 34787
$704,900105 Days on yellowkey MLS ID: O6390611
REDUCED by $5,100 (0.7%) on 05/18/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2440 Built: 2024Monthly Fee: $100 Tax: $8,695 (2025)Community: Osprey RanchSingle Family
Taxes:$8,695
Remarks: The Suncrest II is a spacious rear-load garage home featuring a convenient first-floor Extra Suite. With 10-foot ceilings and an expansive open-concept living area, this thoughtfully designed home offers approximately 2,500 square feet of comfortable living space with stylish finishes throughout. Currently being used as a builder’s model home, this property is being sold fully furnished with professional designer décor and is leased back to the builder through January 27, 2027, presenting an excellent investment opportunity with secured lease income during the lease term. At the rear of the home, the main living area is anchored by a beautifully designed gourmet kitchen, featuring stainless steel appliances, 42” light cabinetry, quartz countertops, and generous workspace, perfect for both everyday living and entertaining. The home also offers a spacious lanai and private courtyard-style lawn, ideal for outdoor enjoyment. Upstairs, you will find a versatile loft area along with three additional bedrooms, providing ample space for family, guests, or a home office. Located in Osprey Ranch, a beautiful community of new single-family homes in Winter Garden, FL, residents enjoy excellent amenities, a prime location, and thoughtfully designed homes, making this community a wonderful place to call home.
Listing is courtesy of: KICANTO REALTY (305-744-2297)
Listing Agent: Cristiane Leon (305-744-2297)
15143 KIRSTY ALY, WINTER GARDEN, FL 34787
$654,900282 Days on yellowkey MLS ID: O6344886
REDUCED by $4,100 (0.6%) on 05/24/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2934 Built: 2017Monthly Fee: $328 Tax: $9,868 (2025)Community: Overlook 2/Hamlin Ph 2 & 5Single Family
Taxes:$9,868
Remarks: Welcome to this beautifully maintained 5-bedroom, 3.5-bathroom move in ready home, ideally situated on a desirable corner lot in the heart of Hamlin, Winter Garden. With a thoughtfully designed layout, this home features one bedroom on the main floor—perfect for guests or multi generational living—and three additional bedrooms upstairs, offering plenty of space and privacy for the whole family. The home boasts soaring open ceilings that create a bright, airy atmosphere throughout. The upgraded kitchen is a true highlight, featuring modern finishes, high-end appliances, and ample space for cooking and entertaining. Adding even more value is the detached mother-in-law suite, offering flexibility for extended family, a private office, or rental income potential. Recently repainted exterior, elegant plantation shutters throughout the entire home, upgraded carpet, screen enclosure, upgraded 8 feet door downstair and upstairs, and the advantage of a spacious corner lot offering extra privacy and curb appeal. Located just minutes from top-rated schools, shopping, dining, and entertainment, this home perfectly combines luxury, functionality, and location in one of Winter Garden’s most sought-after communities.
Listing is courtesy of: ARION REALTY (407-564-8888)
Listing Agent: Jin Cheng (561-346-5225)
16749 HARPER COVE DR, WINTER GARDEN, FL 34787
$499,99968 Days on yellowkey MLS ID: O6400511
0 Days Off yellowkey (back on 5/29/2026)
REDUCED by $15,001 (2.9%) on 05/19/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2014 Built: 2019Monthly Fee: $257 Tax: $7,287 (2024)Community: Waterleigh Ph 2C-1Single Family
Taxes:$7,287
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 3-bedroom, 2.5-bath two-story home featuring a rear-load 2-car garage, ideally located in one of the area’s most desirable master-planned communities. Designed for modern living, the open-concept floor plan showcases durable tile flooring throughout the main level for easy maintenance. The kitchen is a true centerpiece, complete with granite countertops, white cabinetry, stainless steel appliances, and a large center island—perfect for entertaining or everyday living. The spacious first-floor primary suite is filled with natural light and features a walk-in closet, dual-sink granite vanity, and an oversized walk-in shower. Upstairs, you’ll find brand new carpet, a versatile loft space, two additional bedrooms, and a full bathroom with a dual-sink vanity and tub/shower combination—ideal for guests or family. Waterleigh continues to stand out as one of the premier communities in Horizons West, offering resort-style amenity centers, multiple pools, splash pads, indoor and outdoor fitness areas, scenic lakes and ponds, walking and nature trails, beach volleyball courts, playgrounds, and sports fields. A Publix is conveniently located at the community entrance, and lawn maintenance is included for added ease. This is Florida living at its best—whether you're an investor or end user. Schedule your private showing today.
Listing Agent: Tara Garkowski (407-405-8829)
5443 BOWMAN DR, WINTER GARDEN, FL 34787
$649,00039 Days on yellowkey MLS ID: O6408812
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2656 Built: 2015Monthly Fee: $339 Tax: $7,564 (2025)Community: Overlook 2/HamlinSpa: NoSingle Family
Taxes:$7,564
Remarks: Under contract-accepting backup offers. Luxury lakeview living with private apartment above the garage. Welcome to your dream home, where luxury, comfort and thoughtful design come together in one of Hamlin’s sought-after communities. This exceptional residence features four spacious bedrooms, each with its own en-suite bath on the second floor, including one bedroom with en-suite bath conveniently on the first floor, plus an additional half bath for guest convenience. A standout feature is the desirable private Next Gen suite above the garage, offering incredible flexibility for multigenerational living, extended guests, a home office or potential rental income. Enjoy peaceful water views that create the perfect backdrop for both relaxing mornings and beautiful Florida sunsets. In a top-rated A-rated school district, this home offers not only luxury living but also outstanding educational opportunities. Enjoy a walkable lifestyle with direct access to dining, cafés, boutique shopping, fitness studios, parks and entertainment all nearby. This vibrant, growing community offers unmatched convenience and everyday enjoyment right outside your doorstep. More than just a home, this is a place where neighbors become friends and lasting memories are made in one of Central Florida's desirable areas. Schedule your private showing today and experience it for yourself!
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-581-7888)
Listing Agent: Carolina Medeiros (305-753-1943)
11045 HOLLOW BAY DR, WINTER GARDEN, FL 34787
$739,90090 Days on yellowkey MLS ID: O6394192
REDUCED by $10,000 (1.3%) on 05/29/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2113 Built: 2025Monthly Fee: $295 Tax: $3,196 (2025)Community: WaterleighSingle Family
Taxes:$3,196
Remarks: Why wait to build when you can move right into this gently used, practically brand-new home in the highly sought-after Waterleigh community? On a Private, Waterfront LOT! Nestled on a peaceful, quiet street with no rear neighbors, this 4-bedroom, 3-bathroom gem offers over 2,000 sq. ft. of functional living space, perfect for modern family living. Step inside and immediately appreciate the open, airy layout, featuring wood-look tile floors throughout for a sleek, low-maintenance finish. The heart of the home is an inviting living area, ideal for both everyday living and entertaining. The spacious kitchen offers ample storage, and the bright bedrooms provide a retreat at the end of the day. No detail has been overlooked in this home’s design. Situated on a beautiful conservation/water lot, you’ll enjoy serene views and privacy with no rear neighbors. It's the perfect backdrop for your outdoor living moments, whether you're relaxing on your patio or taking in the tranquil surroundings. Waterleigh offers an active and vibrant community lifestyle, with access to multiple resort-style amenity centers, including clubhouses, indoor fitness centers, walking trails, playgrounds, and sports fields—perfect for all ages. The community also provides lawn care and weed control as part of the HOA, so you can spend more time enjoying your beautiful home and less time maintaining it. The community is conveniently located near top-rated schools, including Water Spring Elementary and Middle School, and Horizon High School, making it ideal for families. You’re just a short drive away from everything Central Florida has to offer—amusement parks, shopping, dining, and entertainment. With easy access to I-4 and 429, commuting to all parts of the area is a breeze. Plus, the charming historic district of Downtown Winter Garden is just minutes away, featuring unique boutiques, restaurants, and entertainment options. This beautiful home is truly move-in ready and waiting for its next owner. Don’t miss out on the chance to make it yours—schedule your private showing today before it's SOLD!
Listing is courtesy of: VOSS REALTY INC (407-456-0777)
Listing Agent: Lindsay Kaye Voss (407-456-0777)
1209 CASTLEPORT RD, WINTER GARDEN, FL 34787
$659,000104 Days on yellowkey MLS ID: O6390760
REDUCED by $5,900 (0.9%) on 05/29/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2812 Built: 2001Monthly Fee: $243 Tax: $4,030 (2025)Community: Stoneybrook WestSpa: NoSingle Family
Taxes:$4,030
Elementary School: Whispering Oak Elem
Middle School: SunRidge Middle
Remarks: Welcome to 1209 Castleport Rd — your next chapter in Stoneybrooke West, a gorgeous golf-course community where everyday feels like a getaway. From the moment you arrive you’ll love the manicured fairways, peaceful walking paths, and neighborhood pride that make this community stand out. Step inside and imagine family mornings and movie nights in the bright, open living spaces. This home offers 5 spacious bedrooms and 3 full bathrooms — plenty of room for guests, a home office, or a hobby room. Thoughtful finishes and flexible room spaces make entertaining effortless and daily life comfortable. Location is everything: you’re minutes from theme parks, with fast highway connections for stress-free commutes and weekend escapes, plus easy access to shopping, dining, and services. Whether you’re teeing off on the greens, grabbing dinner nearby, or heading out for a day at the parks, 1209 Castleport Rd combines comfort, convenience, and that warm, community feel you’ve been looking for.
Listing is courtesy of: THE PROPERTY STOP LLC (407-744-5557)
Listing Agent: Angela Magac (407-744-5557)
516 S HIGHLAND AVE, WINTER GARDEN, FL 34787
$500,00032 Days on yellowkey MLS ID: O6409675
1 Days Off yellowkey (back on 5/29/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1716 Built: 1955 Tax: $709 (2025)Community: Rep Pt Pleasant Park SubSingle Family
Taxes:$709
Remarks: Under contract-accepting backup offers. Some Photos virtually staged. Solidly built mid-century home in an exceptional Downtown Winter Garden location, just moments from Plant Street shopping and dining, Crooked Can Brewing Company, Garden Theatre, the splash pad, and all the charm of the golf cart district. Enjoy dinner downtown, then take your golf cart to Newton Park to catch breathtaking sunsets over Lake Apopka. Hard to find, timeless charm and well maintained! Offering 1,716 sq. ft. per the property appraiser, including a spacious laundry room. The roof was replaced in 2016, windows have been updated, and the home includes a termite bond for added peace of mind. Rare opportunity to own a one owner (since the 60's) home, lovingly cared for in a Prime Downtown location~ Schedule your private showing today!
Listing is courtesy of: WINDSOR REALTY GROUP INC (407-877-3463)
Listing Agent: Lisa Bennett (407-877-3463)
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