Location: Winter Garden
Do Not Show Listings
2227 OAKINGTON ST, WINTER GARDEN, FL 34787
$489,9907 Days on yellowkey MLS ID: O6414707
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1867 Built: 2002Monthly Fee: $240 Tax: $5,321 (2025)Community: Stoneybrook West 47/78Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,321
Elementary School: Whispering Oak Elem
High School: West Orange High
Tax Year: 2025
Middle School: SunRidge Middle
Remarks: Welcome to this beautifully maintained 4-bedroom, 2-bath home located in the highly desirable gated golf community of Stoneybrook West in Winter Garden. This move-in-ready residence features an open and spacious floor plan with separate living and dining areas, high ceilings, abundant natural light, and ceramic tile throughout. The upgraded kitchen offers granite countertops, ample cabinet space, and all appliances are included. The spacious primary suite features a large walk-in closet and an updated bathroom with skylights, dual vanities, a garden tub, and a separate shower. Enjoy outdoor living in the fully fenced backyard with a large patio, perfect for entertaining or relaxing. Recent updates and meticulous care make this home a true standout. Roof replaced in 2021. Property comes with solar panels. Residents enjoy resort-style amenities including a community pool, fitness center, tennis and basketball courts, playgrounds, lake access, fishing pier, boating, and 24-hour guarded gate security. Conveniently located near top-rated schools, shopping, dining, major highways, downtown Winter Garden, and Orlando's world-famous attractions. Don't miss this exceptional opportunity—schedule your private showing today!
Listing is courtesy of: REALTY ONE GROUP EVOLUTION (786-477-4715)
Listing Agent: Milena Nunez (407-247-1814)
14903 DRIFTWATER DR, WINTER GARDEN, FL 34787
$390,0006 Days on yellowkey MLS ID: S5151359
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1745 Built: 2015Monthly Fee: $402 Tax: $6,152 (2025)Community: Signature Lakes Ph 3B-6Townhouse
Taxes:$6,152
Elementary School: None
High School: None
Middle School: None
Remarks: Well keep and move in ready corner unit townhouse at the beautiful signature lake at winter garden ,brand new vinyl plank floor at the first floor this 3 bedroom and 2.5 bath room townhouse have 1750 sqft and feature big court yard between the garage you can enjoy the outdoors living on the big courtyard , the oversize front porch is welcome to their new owner , the first floor feature all ceramic title ,have living room and the work space at the front the house and the the kitchen offer gorgeous granite counter tops , wood cabinet and pendant lighting , open up the family room , also have powder room at the first floor , upstair you have 3 bedroom big walk in closet at the master bedroom and dual sink at the master bathroom and one more full bath to share for the other bedroom , signature lake is sought after community at winter garden , feature resort style pool and state of the art gym and club house many event for the residence for the community , grade A school . it is close located next to the Hamlin shopping center and the winter garden village close to 429 and 535 , the HOA fee include cable include HBO and high speed internet from sepcturm . , this is turn key townhouse is ideal for who enjoy low maintenance lifestyle .
Listing is courtesy of: NUMBER 1 BROKER, LLC (407-566-3400)
Listing Agent: Eric Jia (407-401-1431)
12026 SHINE VIEW LN, WINTER GARDEN, FL 34787
$596,19040 Days on yellowkey MLS ID: O6405058
3 Days Off yellowkey (back on 5/27/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2216 Built: 2025Monthly Fee: $190 Tax: $1,989 (2025)Community: WaterleighSpa: NoSingle Family
Taxes:$1,989
Remarks: Under Construction. Waterleigh presents the Bellake. This amazing all concrete block construction single-family home features 3 bedrooms and 2.5 bathrooms optimizing living space with an open concept feel. The kitchen overlooks the dining and great room, while having view to the covered lanai outside. Ample windows and a set of sliding glass doors allow lighting into the living area. The well-appointed kitchen features an island with bar seating, plentiful cabinet and counter space and stainless steel appliances, making entertaining a breeze. The first floor also features a flex room that provides an area for work or play and half bathroom. As we head up to the second floor, we are greeted with Bedroom one which includes a spacious walk-in closet as well as ensuite bathroom with double vanity. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. Your laundry room is located on the second floor as well. This home features a two car garage located at the rear of the home complete with drop zone as you enter the home. Like all homes in Waterleigh, the Bellake 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)
17865 ADRIFT RD, WINTER GARDEN, FL 34787
$599,000326 Days on yellowkey MLS ID: O6329586
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2484 Built: 2023Monthly Fee: $277 Tax: $9,155 (2024)Community: Waterleigh Ph 4B & 4CSingle Family
Taxes:$9,155
Elementary School: Water Spring Elementary
High School: Horizon High School
Tax Year: 2024
Middle School: Water Spring Middle
Remarks: A home full of charm, comfort, and practicality. It features four bedrooms, including a spacious master suite, three full bathrooms, and a powder room, distributed in a clever layout that enhances each room. Right at the entrance, the balcony invites you to slow down and enjoy the home's cozy atmosphere. The kitchen is modern and functional, equipped with all essential appliances and a central island perfect for quick meals or family time. The laundry room is also fully equipped and ready for everyday use. Upstairs, a spacious loft opens up to new possibilities—it could be a TV room, office, or leisure space—in addition to three bright and comfortable bedrooms. Sliding doors connect the interior area with the private backyard, where the covered balcony offers stunning views. With no neighbors in the back, the environment is quiet, private, and ideal for relaxation. The condominium offers a complete infrastructure, with swimming pools, gyms, and leisure areas for the whole family. The location is strategic, with supermarkets, schools, and various amenities nearby, as well as easy access to the region's main attractions. The house is currently occupied, but you can schedule a viewing. A rare opportunity to live well, with tranquility and quality of life.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Joao Freitas De Souza Freitas, Jr (407-342-6363)
15907 MARINA BAY DR, WINTER GARDEN, FL 34787
$443,50063 Days on yellowkey MLS ID: O6398406
4 Days Off yellowkey (back on 6/9/2026)
REDUCED by $6,500 (1.4%) on 05/06/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1818 Built: 2020Monthly Fee: $286 Tax: $7,110 (2025)Community: Hawksmoor-Ph 1Townhouse
Taxes:$7,110
Remarks: Welcome to your future home, a harmonious blend of luxury, comfort, and convenience nestled within the vibrant community of Hawksmoor, located in Winter Garden, FL. This impeccably designed 3-bedroom plus loft, 2.5-bathroom townhome offers unparalleled living, featuring upgrades and amenities that redefine modern living. As you step inside, you're greeted with ambiance of spaciousness and style. The foyer leads seamlessly into a dining room and a generous size family/living room, adorned with 20' ceilings. The large outdoor courtyard is perfect for entertaining or unwinding in tranquility. Designed for both functionality and elegance, the chef's kitchen boasts premium features including granite countertops, upgraded cabinetry, stainless steel appliances, and a convenient walk-in pantry. The meticulous attention to detail extends throughout the home, with tile flooring in the first floor, carpet in the bedrooms, and tile in the bathrooms and laundry room. The first-floor master suite is a haven of relaxation, offering a walk-in closet and an en-suite bathroom with upscale finishes. Upstairs, two additional bedrooms, a full bath, and a versatile loft space provide ample room for family living or personal retreat. This end unit townhome offers privacy and tranquility. Beyond the home's exquisite interior, enjoy the convenience of a two-car garage, providing ample storage space for your vehicles and belongings. The community offers an array of amenities designed to enhance your lifestyle, including a resort-style swimming pool, clubhouse, shaded playgrounds, walking trails, and a fully-equipped gym. Conveniently located within Winter Garden's popular Horizon West area, you're just minutes away from downtown attractions, world-class theme parks, and a plethora of shopping and dining options. Easy access to major highways ensures seamless commutes to work and leisure destinations alike. Don't miss the opportunity to make this meticulously crafted townhome your own.
Listing is courtesy of: SIMPSON REALTY LLC (407-371-5955)
Listing Agent: Cristian Cen Chen (407-450-9010)
14501 GROVE RESORT AVE #3425, WINTER GARDEN, FL 34787
$480,0006 Days on yellowkey MLS ID: O6414956
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1265 Built: 2018 Tax: $7,044 (2025)Community: Grova Residence & Spa Hotel Condo 3Condo
Taxes:$7,044
Remarks: Welcome to The Grove Resort & Water Park, a luxury vacation condo-hotel community offers owner privacy and convenience. Located 5 minutes from Walt Disney World, ownership of the largest 2-bedroom provides a family friendly place to vacation and relax. Let's discuss more about this 2B When you step through the door, you enter directly into the living space. The unit features in-unit laundry, with full-size washer and dryer. The kitchen is well-equipped with all major appliances, so you can certainly cook here if desired. The living space is spacious, and also includes a dining area. You can be making $ on the day of closing! Financial statements are available! Please note that this is a condo-hotel, so you could not live here full time due to zoning restrictions
Listing is courtesy of: MIAMI LIFE REALTY LLC (786-464-8804)
Listing Agent: Jorge Kupferman (786-306-7308)
15025 EVERGREEN OAK LOOP, WINTER GARDEN, FL 34787
$505,00023 Days on yellowkey MLS ID: O6410108
REDUCED by $5,000 (1.0%) on 06/08/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2477 Built: 2016Monthly Fee: $195 Tax: $8,019 (2025)Community: Signature Lakes Ph 3B-4 3B-5 3B-Single Family
Taxes:$8,019
Elementary School: Independence Elementary
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: Motivated seller. New paint and new flooring throughout. This home features two primary suites — one downstairs and one upstairs. Located in an area with all A-rated schools. Close to Disney World, and you can even enjoy Disney fireworks from the front yard. The home is conveniently located near Super Walmart, Winter Garden Village shopping centers, and top-rated restaurants. The Independence Community Association offers outstanding amenities, including: 2 community pools, green spaces & park areas, tennis & basketball courts, a main clubhouse with fitness & arcade, 2nd clubhouse with fitness & billiards, community boat ramp to ski-able Lake Hancock, dog park, bike & walking paths. HoA fee covers basic TV CABLE and WIFI.
Listing is courtesy of: CENTURY 21 CARIOTI (407-354-0074)
Listing Agent: Bo Zhang (407-848-8486)
5526 TINY RD, WINTER GARDEN, FL 34787
$1,590,000311 Days on yellowkey MLS ID: O6334009
3 Days Off yellowkey (back on 6/8/2026)
REDUCED by $85,000 (5.1%) on 06/01/2026
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2474 Built: 2007 Tax: $10,165 (2024)Community: NoneSingle Family
Taxes:$10,165
Remarks: Under contract-accepting backup offers. A Rare Slice of Serenity in the Heart of Horizons West — 5526 Tiny Road Almost five acres in the middle of one of Central Florida's most sought-after communities isn't just rare — it's nearly impossible to find. While the rest of Horizons West builds closer together, 5526 Tiny Road sits on almost five rolling, private acres surrounded by open sky, a private pond, and natural Florida landscape — all within walking distance of community trails, top-rated schools, and the brand-new Orange County Library currently under construction just steps away. This is the property buyers spend years waiting for. The freedom of acreage. The convenience of community. No HOA. No compromise. The custom-built 2007 estate offers 2,400 square feet of thoughtfully designed living space — three bedrooms, a spacious loft, and 2.5 bathrooms inside, plus a half bath in the oversized 3.5-car garage built for the enthusiast, the workshop, the toys, or all three. The open-concept layout is filled with natural light, anchored by a gourmet kitchen and flowing living spaces designed for both everyday comfort and effortless entertaining. Step outside and the property truly comes alive. A front gazebo attached to the home frames sweeping views across the acreage. The screened rear lanai overlooks a nature preserve. Sunrises and sunsets paint the elevated ridge in a way that no subdivision lot can replicate. Wild turkeys, native birds, and open Florida sky are your neighbors. Just a short ride to Hamlin Town Center, Disney World, SR-429, and everything Horizons West continues to build around you — including planned road enhancements to Tiny Road itself, with landscaped medians and expanded sidewalks that will further elevate the entrance to this property. Properties like this don't come back to market. Once it's gone, it's gone — because there is nothing left to build like it here. 3 Bed | Loft | 2.5 Bath + Garage Half Bath | 3.5-Car Garage | Almost 5 Acres | No HOA | Custom 2007 Build | Private Pond | Horizons West / Independence-Summerport
Listing is courtesy of: BUYER REBATES REALTY (407-629-2300)
Listing Agent: Sean Popat (407-399-1669)
279 ZACHARY WADE ST, WINTER GARDEN, FL 34787
$1,675,00031 Days on yellowkey MLS ID: O6408014
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4473 Built: 2003Monthly Fee: $67 Tax: $8,609 (2025)Community: Lakeview ReserveSpa: YesSingle Family
Taxes:$8,609
Elementary School: Tildenville Elem
Middle School: Lakeview Middle
Remarks: An unparalleled lakefront opportunity in Downtown Winter Garden **Seize the rare chance to own a premier waterfront estate where the true value lies in the spectacular lot, private dock, and an enviable golf-cart lifestyle ** Launch your boat from your private lift for a scenic 30-minute cruise to Mt. Dora or take your golf cart just minutes away to the historic downtown Farmers’ Market and restaurants **Positioned within a private, gated enclave directly across from the West Orange Trail, this property offers the ultimate Florida resort lifestyle outside, featuring a heated saltwater pool, raised spa, and a fully fenced, expansive lakeside yard ** Inside, the home boasts a massive primary suite +/16x26’ with tray ceiling, fireplace and a balcony with lovely lake views and massive +/-23x25 bonus room including a wet bar and fireplace** The kitchen has a large cooking island w/sink plus a separate breakfast bar, stone counters, under cabinet lighting, a Jenn-Air double convection oven and lovely dining area overlooking the lake ** There's even an open wine closet/alcove with wine refrigerator off the kitchen ** First floor bedroom with an oversized walk in closet as a 5th bedroom or den (currently being used as a dining room) ** Other home upgrades include a newer roof +/-2022, 3 newer A/C units, a whole-home Katolight 40KW generator that runs +/- 90% of the home, crown molding throughout the home, ADT security system with cameras, boat house with new roof 2025, resurfaced pool +/-5 yrs ago & Aqualink pool/spa automation system and a 10’ seawall ** Relax on the covered screened patio with the Bose speaker system and prime outdoor living space including additional yard space beyond the pool and patio ** 2 car garage plus a 1 car garage with easy access to the back yard perfect for bringing your boat or lawn equipment through ** LOW HOA fees $200 quarterly ** All room measurements in MLS and on 3d floorplan are approximate. Buyer to verify. Tax record is incorrect - property has 5 bedrooms. Dock measurement is estimated. Buyer to verify. Solar panel lease to be transferred to buyer at closing.
Listing is courtesy of: INDEPENDENCE REALTY GROUP LLC (407-408-6662)
Listing Agent: Andrew Philippone (407-408-6662)
15026 SUMMER HARVEST ST, WINTER GARDEN, FL 34787
$689,990137 Days on yellowkey MLS ID: S5142710
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2908 Built: 2024Monthly Fee: $202 Tax: $9,669 (2025)Community: Harvest At OvationSingle Family
Taxes:$9,669
Middle School: Horizon West Middle School
Remarks: Seller offering up to $15,000 toward buyer’s closing costs, prepaids, or interest rate buy-down with acceptable offer. Exceptional opportunity in highly desirable Winter Garden/Horizon West! This beautifully upgraded 5-bedroom, 4.5-bath home offers over 2,900 sq. ft. of flexible living space, including a private in-law suite with its own separate entrance, bedroom, bathroom, and kitchenette — currently rented for $1,300 per month, providing immediate income potential or an ideal space for multigenerational living. The main home features an open-concept layout, high ceilings, upgraded flooring, a renovated kitchen, modern finishes, and spacious living areas designed for comfort and functionality. The private suite adds exceptional value for buyers looking for rental income, a guest retreat, a private office, or independent living space. Located just minutes from Disney, Flamingo Crossings, Hamlin, shopping, dining, entertainment, hospitals, and top-rated schools, this home offers the perfect combination of location, lifestyle, and income potential. Enjoy the benefits of living in one of Central Florida’s fastest-growing and most desirable communities. A rare opportunity to own a move-in-ready home with upgrades, a private income-producing suite, and a seller incentive of up to $15,000 with an acceptable offer.
Listing is courtesy of: AROD PARTNERS REALTY (407-627-7621)
Listing Agent: Keyla Chirinos Sivira (786-380-5541)
8721 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787
$679,00042 Days on yellowkey MLS ID: G5111855
REDUCED by $16,000 (2.3%) on 06/08/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2842 Built: 2015Monthly Fee: $342 Tax: $8,082 (2025)Community: Waterleigh Ph 1ASpa: NoSingle Family
Taxes:$8,082
Elementary School: Panther Lake Elementary
Remarks: Amazing opportunity for a corner lot pool home, within the highly demanded Waterleigh - Marina Bay neighborhood. With views of Hickorynut Lake from the front porch and theme park fireworks from the back porch and pool, you have found resort-style living with easy access to everything Central Florida has to offer. Looking for more privacy while enjoying the heated pool? Simply close the privacy curtains that are installed around the pool cage. Inside, you’ll find a spacious home that includes 4 bedrooms, 3 and a half bathrooms, a flex space, a loft, ample storage, and much more. The primary suite is located on the first floor, while one of the second floor bedrooms is designed like a secondary primary with a bathroom en suite. Take advantage of numerous upgrades throughout including, Smart Home features, security options, car charger in garage, wood and tile flooring throughout, granite countertops, plantation shutters, under stairs storage and attic storage where drywall and lighting have been added. Recent updates include, pool (June 2023), exterior paint (Feb 2022), HVAC (Jan 2022), pavers cleaned & sealed (June 2023). When not enjoying the beauty of your home, take advantage of the numerous resort-style amenities that come with living in Waterleigh including, lawn & landscaping maintenance provided by the HOA, two large clubhouses with rentable space, four resort-style pools, two fitness centers, tennis, sand volleyball, mini-golf course, walking paths that take advantage of how the neighborhood wraps around the lake, regular community events, and so much more. As you venture outside of the community you find the home’s location puts you in close proximity to schools, Orange County National Golf, the numerous village centers of Horizon West, Historic Downtown Winter Garden, and quick access to all Central Florida has to offer with 429 connecting you to the Florida Turnpike, 408, and I-4.
Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)
Listing Agent: Joshua Howard (407-739-9118)
16071 BARKLY RIDGE CT, WINTER GARDEN, FL 34787
$1,150,00093 Days on yellowkey MLS ID: O6390569
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2986 Built: 2024Monthly Fee: $225 Tax: $2,420 (2024)Community: Avalon RidgeSingle Family
Taxes:$2,420
Elementary School: Hamlin Elementary
Middle School: Hamlin Middle
Remarks: Enchanting newly built home in Avalon Ridge with a private pool, located in one of the most desirable areas of Winter Garden. This beautiful residence has been thoughtfully designed and features 4 bedrooms with carpet flooring, 3 full bathrooms, and a perfect blend of modern space, functionality, and elegant finishes. The living area features sliding glass doors that open to the outdoor space and private pool, creating the perfect setting for entertainment and relaxation. The spacious living room flows seamlessly into a large kitchen equipped with modern cabinetry, stainless steel appliances, elegant countertops, and a generous center island. The primary suite offers a spacious bathroom with dual sinks, a large walk-in closet, and a comfortable walk-in shower. The three additional bedrooms provide plenty of space for family members or guests. The three-car garage offers ample room for vehicles, storage, or even a workspace. Ideally located in a rapidly growing area, just minutes from major highways, shopping centers, restaurants, and top-rated schools. Don't miss this opportunity—schedule your showing today!
Listing Agent: Jennifer Olmeda (407-547-9242)
9493 EMERALD BERRY DR, WINTER GARDEN, FL 34787
$999,000338 Days on yellowkey MLS ID: O6325653
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3211 Built: 2025Monthly Fee: $86 Tax: $1,857 (2024)Community: Summerlake ReserveSingle Family
Taxes:$1,857
Remarks: We present an impeccable, newly built home in brand-new condition, ready to welcome you and your family with comfort, modernity, and style. Located in the sought-after Summerlake Reserve community in Horizon West, this home surprises with every detail. Upon arrival, the charming porch with its well-kept garden gives you a taste of what lies ahead. Upon entering, the integrated living, dining, and kitchen areas create a feeling of spaciousness and warmth, perfect for those who value open, well-lit spaces. Large sliding doors allow for abundant natural light and connect the interior with the exterior. With high ceilings of almost 3 meters, the home exudes elegance and sophistication. The kitchen is a true highlight: equipped with modern appliances, high-end wood cabinetry, a large central island, and a spacious pantry—ideal for those who love cooking and entertaining. The four bedrooms are spacious, well-appointed, and designed to offer maximum comfort. There are three and a half bathrooms, all with quality finishes and tasteful furnishings. The laundry room offers a functional space and is already equipped to make daily life easier. The garage accommodates three cars and has an automatic gate, ensuring convenience and security. All this in a prime location, close to schools, shops, restaurants, and all the amenities that make Horizon West one of the most valued areas in Florida. If you're looking for a new, modern home in a complete community, this is the perfect opportunity. Schedule your visit and come see for yourself!
833 BENDING OAK TRL, WINTER GARDEN, FL 34787
$399,00037 Days on yellowkey MLS ID: O6403683
0 Days Off yellowkey (back on 6/8/2026)
REDUCED by $26,000 (6.1%) on 05/18/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1789 Built: 2009Monthly Fee: $447 Tax: $4,032 (2025)Community: Oaks/Brandy Lake OTownhouse
Taxes:$4,032
Remarks: Under contract-accepting backup offers. Beautifully maintained and truly turn-key, this 3-bedroom, 2.5-bath townhome is the kind of home where you can simply move in and start enjoying everything Winter Garden has to offer from day one, all while being located in the highly sought-after Golf Cart District just moments from the heart of charming Downtown Winter Garden! From the moment you walk in, you’re welcomed by bright, open living spaces, thoughtful design, and timeless finishes that make the home feel warm, elevated, and instantly inviting. Plantation shutters throughout add that polished custom touch, while the open-concept layout creates the perfect flow for both everyday living and entertaining. Upstairs, the spacious primary suite feels like its own private retreat, thoughtfully positioned away from the guest rooms so you can truly enjoy your own space. Wake up to beautiful open skies and unwind each evening with stunning sunset views right from your bedroom. This is townhome living exactly how it should be. Where else in Winter Garden can you enjoy a home like this, have pool access just a short walk away, and spend your weekends enjoying life instead of worrying about exterior upkeep? Lock it, leave it, travel when you want, and come home to a space that always feels effortlessly cared for. And the location? It’s hard to beat! Bending Oak Trail offers that true neighborhood feel with peaceful evening walks, friendly neighbors, and a sense of community that makes you feel right at home, all while being just moments from the heart of Downtown Winter Garden—one of Central Florida’s most beloved downtowns, known for its brick-lined streets, incredible local restaurants, charming boutiques, cozy coffee shops, weekend Farmer’s Market, and year-round community events that make this area so special. Hop on your golf cart and head down Plant Street for your morning coffee, dinner with friends, shopping, or an evening stroll. Even better, you’re right next to the West Orange Trail, making morning bike rides, walks, and outdoor living part of your everyday lifestyle. With quick access to 429, the Turnpike, SR-50, Disney, Downtown Orlando, and Orlando International Airport, convenience is seamlessly built into daily life. Winter Garden continues to be one of Central Florida’s most sought-after communities, and opportunities to own something this move-in ready, this well-located, and at this price point are incredibly hard to find.
Listing is courtesy of: GLOBAL FLORIDA REALTY (407-380-3030)
Listing Agent: Lauren Bouchard (352-978-6837)
9360 MCLAREN ALY, WINTER GARDEN, FL 34787
$615,00023 Days on yellowkey MLS ID: O6408913
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2477 Built: 2020Monthly Fee: $257 Tax: $7,373 (2025)Community: WaterleighSingle Family
Taxes:$7,373
Remarks: Welcome to this beautifully appointed, move-in-ready home located in the highly desirable, resort-style master-planned community of Waterleigh in Winter Garden. This home offers the perfect blend of modern sophistication and everyday functionality across a bright, open-concept design. From the moment you enter through the front door, the airy foyer welcomes you with elegant, durable ceramic tile in a natural wood-grain finish. This flooring flows seamlessly through the main living areas, which are accented by striking arched doorways and a beautifully crafted staircase. The heart of the home is the stylish chef's kitchen, which shines with pristine shaker-style cabinetry, expansive granite countertops, a classic tiled backsplash and a generous center island with an undermount double sink and an extended breakfast bar perfect for casual dining. Fully equipped with sleek stainless-steel appliances and a dedicated built-in beverage cooler station, this culinary space overlooks a main living zone flooded with natural Florida sunshine through large windows with custom blinds. The primary bedroom ensuite features dual vanity sinks, stone countertops and a massive walk-in closet. Upstairs, the second-floor balcony is the place to unwind after a long day or start your morning with sun salutations. A brick-paved backyard patio and a rear-entry garage provideultimate privacy for your new sanctuary. Living in Waterleigh means enjoying a vacation-style lifestyle every day. With HOA-included lawn and ground maintenance, you have nothing left to do but relax and enjoy the community's premier amenities, including multiple resort-style pools, fitness centers and tennis and pickleball courts. Plus, you are just minutes from Disney's Magic Kingdom, upscale shopping at Winter Garden Village, historic downtown Winter Garden and Orlando International Airport.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-581-7888)
Listing Agent: Leslie Heimer (407-494-9833)
5211 CITRUS LEAF BLVD, WINTER GARDEN, FL 34787
$799,000153 Days on yellowkey MLS ID: O6373067
REDUCED by $20,000 (2.4%) on 05/16/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2909 Built: 2023Monthly Fee: $165 Tax: $9,990 (2024)Community: Silverleaf Reserve/Hamlin Ph 2Single Family
Taxes:$9,990
Remarks: Welcome to this exceptional Barret floor plan in the exclusive Silverleaf Reserve by Meritage Homes, offering 4 spacious bedrooms, a versatile bonus room, a dedicated office, and an additional flex space currently used as a music room. Positioned on one of the best lots in the community, this home features stunning lake views, unmatched privacy, and a thoughtfully designed layout for both comfort and functionality. This residence is loaded with upgrades: luxury vinyl flooring throughout, elegant quartz countertops, soft-close cabinetry, designer glass-front cabinets, and beautiful under-cabinet lighting that adds charm and sophistication to the kitchen. The master bedroom is located on the second floor, making it perfect for families with young. On the first floor, a guest suite is conveniently located near the entrance, ideal for visitors or elderly family members. The home also includes a stylish powder room (half bath) for added convenience. The bonus room provides endless flexibility, whether as a media room, playroom, or additional lounge space, while the office is perfect for working from home. The unique music/flex room adds character and versatility to the home. Located in Winter Garden’s prime area, Silverleaf Reserve offers not only a premium lifestyle but also the convenience of two highly rated public schools (elementary and middle) right inside the community, along with easy access to shopping, dining, and major highways. This property is the perfect combination of modern design, luxury finishes, and an unbeatable location — a rare opportunity in the heart of Winter Garden.
Listing is courtesy of: MCO REALTY GROUP LLC (407-747-3822)
Listing Agent: Tiago Fernandez Pllc (407-747-3476)
15058 SUNSTAR WAY, WINTER GARDEN, FL 34787
$1,900,00016 Days on yellowkey MLS ID: O6411520
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3607 Built: 2021Monthly Fee: $110 Tax: $645 (2025)Community: Highlands/Summerlake Grvs Ph 3Spa: YesSingle Family
Taxes:$645
Elementary School: Summerlake Elementary
Remarks: Experience LUXURY ~ WATERFRONT LIVING in this FULLY UPGRADED ~ POOL HOME in the sought-after Highlands at Summerlake Groves community of Horizon West! Built in 2021 and situated on a generous .40 ACRE LOT with a FENCED YARD, this exceptional home delivers breathtaking nightly views of DISNEY FIREWORKS reflecting across the water, creating a spectacular backdrop you can enjoy year-round from the comfort of your own home. Designed with both everyday living and unforgettable entertaining in mind, this home offers an OPEN CONCEPT layout filled with natural light, a dramatic two-story living room with a chic FIREPLACE feature wall, CUSTOM BUILT-INS, and WOOD LOOK TILE flooring throughout the main living areas. The spacious MAIN FLOOR PRIMARY SUITE delivers a private retreat, while a dedicated OFFICE with custom built-in cabinetry and desk space makes working from home effortless. Upstairs, you will find three additional bedrooms and one of the home's most impressive features – a PROFESSIONALLY DESIGNED THEATER ROOM with over $350,000 invested in premium finishes and technology, including a $12,000 projector, professional acoustic treatments, custom wall detailing, and seating for eight. No detail was overlooked when it comes to technology and convenience! Whole-home automation controls music, lighting, outdoor fans, LED lighting, water features, and more with the touch of a button. The WHOLE HOME & POOL SOUND SYSTEM further enhances the experience, while the two-car garage includes its own mini-split A/C system. Additional upgrades include a TILE ROOF, water softener, paver driveway, and separate 1-car and 2-car garages offering ample storage and flexibility. Step outside and discover a backyard designed to rival a private resort. The COVERED LANAI features a fully equipped OUTDOOR KITCHEN complete with a built-in grill, pizza oven, stone flat-top grill, vent hood, and oversized ISLAND for gathering. MOTORIZED SHADES provide privacy and comfort, while the CUSTOM POOL & SPA showcase three WATER FEATURES, dramatic FIRE ELEMENTS, and panoramic LAKE VIEWS. A perimeter mosquito misting system helps maintain a comfortable outdoor environment day and night, allowing you to fully enjoy Florida living year-round. Whether you are boating, skiing, entertaining guests, enjoying a movie night in the theater, or watching Disney fireworks dance across the lake each evening, this home offers a lifestyle few properties can match. Residents of the Highlands at Summerlake Groves also enjoy community amenities and a prime Winter Garden location just minutes from Orange County National Golf Center, the New Independence area, Disney parks, shopping, dining, Downtown Winter Garden, farmers markets, community events, and convenient access to SR 429. Waterfront luxury, state-of-the-art technology, unforgettable outdoor living, and one of the most impressive theater rooms you will find in a private residence – this is the opportunity you have been waiting for. Call today to schedule a private tour!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
14501 GROVE RESORT AVE #1612, WINTER GARDEN, FL 34787
$299,000237 Days on yellowkey MLS ID: S5136940
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1375 Built: 2016Monthly Fee: $875 Tax: $6,828 (2024)Community: Grove Resort And Spa Hotel Condo 1Condo
Taxes:$6,828
Remarks: Awesome VIEW makes this unit stand out above others! BLDG 1 ALLOWS FINANCING! Come enjoy this EXCEPTIONAL Fully Furnished 6th floor Vacation Condo unit with WATER AND CONSERVATION VIEWS plus Evening Fireworks views from your private South-facing Balcony at The Grove Resort and Spa/Water Park in Orlando near Walt Disney World! Experience the Resort FUN yourself and enjoy the income-producing option to rent out your unit when you are away. This Full-service Fully-furnished Luxury Resort unit is the Birch model (split plan 1375 sq ft) in Bldg 1H. Two bedroom suites plus sleeper sofa in the great room, TVs in all rooms, Fully equipped Kitchen, inside private Laundry room, a short walk to Attached Garage parking, and the Fitness Center is conveniently just downstairs! Experience lifetime memories at the multitude of amenities on site: the Surfari Water Park with an amazing FlowRider Surf Simulator, Lazy River, Water slides, numerous pools and activities, cabanas, meeting areas, shopping options and Family Fun Center, or escape just minutes away to neighboring theme parks, shopping, restaurants, and more!
Listing is courtesy of: WATSON REALTY CORP (407-298-8800)
Listing Agent: Lois Ann Cox, Pa (407-666-8452)
11205 HOLLOW BAY DR, WINTER GARDEN, FL 34787
$939,99083 Days on yellowkey MLS ID: O6392839
1 Days Off yellowkey (back on 5/15/2026)
REDUCED by $10,000 (1.1%) on 05/15/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3327 Built: 2025Monthly Fee: $250 Tax: $1,989 (2025)Community: WaterleighSpa: NoSingle Family
Remarks: Under Construction. Watrerleigh 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. Customize this area to meet your needs with an optional den. 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 additional storage. All homes in this community feature stainless steel appliances, making cooking a piece of cake. Bedroom one is located off the living space in the rear of the home for privacy. It's bathroom impresses with separate vanities, shower/tub space, toilet room with privacy door as well as a spacious walk-in closet. As you head upstairs, you are greeted with a loft area and three bedrooms. Two bedrooms share a upstairs bathroom with double bowl vanity while the additional bedroom is complete with ensuite bathroom. *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.*
15162 CANOPY COVER DR, WINTER GARDEN, FL 34787
$880,000198 Days on yellowkey MLS ID: S5139203
REDUCED by $5,000 (0.6%) on 04/29/2026
Bed: 2 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 2049 Built: 2023Monthly Fee: $545 Tax: $1,939 (2023)Community: Del Webb Oasis Phase 2Single Family
Taxes:$1,939
Tax Year: 2023
Remarks: HEATED SALT WATER POOL IN A CONSERVATION LOT! This exceptional Mystique model by Pulte showcases one of the most impressive outdoor living spaces within Del Webb Oasis, a boutique 55+ resort-style community just minutes from Orlando’s top attractions. Situated on a premium conservation lot, this home offers privacy, tranquility, and unobstructed natural views—an ideal setting for those seeking an elevated and peaceful living experience. With more than $100k in upgrades. At the heart of the property is a remarkable outdoor retreat. Enjoy a custom heated saltwater pool, spa with App-controlled pool features for temperature and lighting and an extended covered lanai featuring a fully equipped outdoor kitchen in this Peaceful conservation backdrop with no rear neighbors. Designed for year-round enjoyment, this space is perfect for entertaining, relaxing, and embracing Florida living at its finest. Sliding glass doors seamlessly connects the indoor living areas to the lanai, enhancing the home’s expansive and open feel. The exterior also includes gutters for added protection and maintenance ease. Inside, this single-story residence features 2 bedrooms, a flex room, perfect for an office, hobby space, or guest accommodations 2 bathrooms, and a 3-car tandem garage. The open-concept layout offers tall ceilings, abundant natural light, and a spacious gathering room. The gourmet kitchen is equipped with built-in Whirlpool appliances, 42” white soft-close cabinetry, Quartz countertops, decorative tile backsplas. The kitchen boasts exquisite, luxurious finishes that elevate the confort and elegance of this wonderful home. The owner’s suite includes a luxury frameless glass walk-in shower, dual quartz vanities, a linen closet, and elegant finishes.. Additional interior upgrades include designer tile flooring throughout, crown molding, 8’ interior doors, comfort-height toilets, and brushed nickel hardware. The laundry room features Whirlpool washer and dryer, quartz countertop, a utility sink, and upgraded cabinetry. This home offers multiple automated features for effortless living: • Electric curtains in the living room and owner’s suite – Controlled via mobile app or Alexa • Smart security camera system, fully app-managed • App-controlled pool system • Watershield Gold softener system included Del Webb Oasis is a natural-gas 55+ community offering resort-style amenities such as a zero-entry pool with sun shelf and lap lanes, private cabanas, spa, fire pits with fireworks views, fitness center, tennis and pickleball courts, walking trails with fitness stations, and a robust calendar of activities organized by a full-time Lifestyle Director. Combining a premier conservation lot, a standout outdoor living area, and high-end interior upgrades, this residence stands out as one of the most desirable homes available in Del Webb Oasis’s 55+ collection. At last, the property you've been waiting for is here - A refined, luxurious retreat just for you. $10K FOR CLOSING COSTS
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Angela Camacho (321-946-2082)
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