Location: Winter Garden
Do Not Show Listings
16975 WINGSPREAD LOOP, WINTER GARDEN, FL 34787
$975,00072 Days on yellowkey MLS ID: O6376353
1 Days Off yellowkey (back on 4/5/2026)
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3557 Built: 2021Monthly Fee: $127 Tax: $9,898 (2024)Community: Hawksmoor Ph 4Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,898
Elementary School: None
High School: Horizon High School
Tax Year: 2024
Middle School: Water Spring Middle
Remarks: Under contract-accepting backup offers. Wake each morning to tranquil lake views and soft natural light that set a serene tone for the day. Built in 2021, this refined residence is positioned on an expansive premium lot within Winter Garden’s sought-after Hawksmoor community, offering the rare luxury of no rear or front neighbors—only open space, conservation views, and uninterrupted privacy. The paved driveway and oversized three-car garage create an impressive arrival and hint at the thoughtfully designed interiors beyond. Inside, soaring ceilings and an open, light-filled layout create an effortless sense of elegance and flow. At the center of the home, the chef-inspired kitchen makes a striking statement with a waterfall island, gleaming quartz countertops, 42-inch cabinetry, and stainless steel appliances—perfectly suited for both intimate mornings and entertaining. From the main living areas, expansive windows frame breathtaking sunset views across the lake and conservation land, seamlessly blending indoor and outdoor living. French doors open to a private office or fifth bedroom featuring a versatile bonus nook—ideal for a home office, creative studio, or serene retreat. Upstairs, a spacious loft provides endless flexibility, whether envisioned as a media lounge, game room, or additional living space. The primary suite is a true sanctuary, highlighted by elegant tray ceilings, dual walk-in closets, and remote-controlled blinds that allow you to reveal the picturesque views at your leisure. Outdoors, the covered lanai invites relaxed evenings and elevated entertaining, all set against the calming backdrop of water and nature. Residents of Hawksmoor enjoy resort-style amenities including a sparkling pool, splash pad, state-of-the-art fitness center, and scenic walking trails. Ideally located just minutes from SR 429, Hamlin Town Center, historic downtown Winter Garden, and world-renowned theme parks, this home offers the perfect balance of privacy, luxury, and convenience
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Kristin Duncan (407-274-5911)
8685 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787
$555,000Listed 04/05/2026 4:46PM MLS ID: O6394975
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2489 Built: 2015Monthly Fee: $332 Tax: $8,849 (2025)Community: WaterleighSingle Family
Taxes:$8,849
Elementary School: Water Spring Elementary
Tax Year: 2025
Remarks: Must see and make your new home today!! Situated in front of a most beautiful, sweeping lakefront view, it's the perfect place to wind down or just relax. It has A+ rated school district. Waterleigh provides a perfect blend of activities, amenities, trails, nature, parks, Tennis, clubhouse pools, fitness, parks, lush landscaping, parks & playgrounds allwing activities for everyone. Beautiful views of spectacular sunsets, & Disney Fireworks at night. You are close to several shopping districts, farmers markets, restaurants, luxury theaters, schools, hospitals, and (of course) at Disney's back door. Inside this beautiful and meticulously maintained home, there is a spacious en suite bedroom downstairs with walk in closet and lake view. A vast great room with large dining area adjacent to an open kitchen plan with plenty of cabinet space and walk in pantry. The appliances, including under counter water purifier and dispenser, are all in excellent condition with a brand new samsung dishwasher. A drop zone from the rear entry attached two car garage (with workbench/countertop). The large pavered screened in lanai is both private and large enough for outdoor sofa and dining al fresco. Upstairs is a bright loft with lake view, and two additional guest bedrooms, one with a beautiful lake view. The master bedroom has a huge double sink vanity, two linen closets, large walk in closet, private privy, and luxury no maintenance shower. This home has it all... except carpets... no carpet anywhere in the home. All flooring is either tile or luxury vinyl plank in a modern birch tone. Weeks and Months Available
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Karan Wienker (310-890-8687)
1005 CHASE DR, WINTER GARDEN, FL 34787
$649,000121 Days on yellowkey MLS ID: A4674195
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2319 Built: 2005Monthly Fee: $68 Tax: $7,086 (2024)Community: Island Pointe SubSingle Family
Taxes:$7,086
High School: None
Middle School: None
Remarks: LUXURY RENOVATED 4-BED HOME WITH NEW ROOF + AC — OVERSIZED 3-CAR GARAGE — MOVE-IN READY This beautifully renovated 4-bed, 2.5-bath single-family home in the heart of Winter Garden (34787) is truly move-in ready — offering a luxury 2025 redesign from top to bottom. Located in the highly desirable Golf Cart District, this home sits on a quiet cul-de-sac just minutes from Downtown Winter Garden, Plant Street Market, and the West Orange Trail. The interior features a bright open floor plan with dramatic double-height ceilings, brand-new tile flooring downstairs and durable LVP upstairs, all-new baseboards and trim, and a fully updated 2025 kitchen with stone countertops and modern cabinetry. The spa-style primary suite includes two walk-in closets, a glass walk-in shower, and a soaking tub. Major upgrades include a new roof, new AC, updated electrical and plumbing, and fresh exterior paint — making this home feel like new construction. The oversized 3-car garage provides rare extra storage and golf cart space. Only 4 minutes to Newton Park with a public boat ramp — perfect for lake access, sunsets, and outdoor recreation. Schedule your private showing today!
Listing is courtesy of: SAVVY AVENUE, LLC (888-490-1268)
Listing Agent: Moe Mossa (888-490-1268)
15162 SPINNAKER COVE LN, WINTER GARDEN, FL 34787
$825,0009 Days on yellowkey MLS ID: O6393190
REDUCED by $25,000 (2.9%) on 04/05/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3902 Built: 2005Monthly Fee: $243 Tax: $7,653 (2025)Community: Stoneybrook WestSingle Family
Taxes:$7,653
Elementary School: Whispering Oak Elem
High School: West Orange High
Middle School: SunRidge Middle
Remarks: *Discounted Interest Rates Available* Nestled on a premier corner lot within the guard-gated enclave of STONEYBROOK WEST, this stunning 5-bedroom, 3-bathroom residence offers the ultimate Winter Garden lifestyle. The home has been meticulously enhanced over the last two years with modern updates, ensuring a move-in-ready experience for today’s discerning buyer. Inside, the open-concept layout is anchored by a gourmet kitchen featuring quartz countertops, a central island, and stainless steel appliances, all flowing into a family room warmed by a classic fireplace. High-volume ceilings—reaching 9.25 feet on the main floor and an impressive 10.50 feet in the massive upstairs bonus room—create an airy, grand atmosphere throughout. Retreat to the primary suite, where tray ceilings and a private walk-out balcony offer a peaceful vantage point overlooking the championship golf course. The lifestyle here extends far beyond the front door. Stoneybrook West is a premier "live-play" community boasting 24-hour staffed security and a spectacular WATERFRONT CLUBHOUSE perched on the shores of BLACK LAKE. For the outdoor enthusiast, the amenities are unmatched: enjoy private access to the lake via a COMMUNITY BOAT RAMP, and take advantage of the rare convenience of an ON-SITE BOAT STORAGE LOT. Whether you are hitting the links on the championship golf course, enjoying the fitness center, or spending the afternoon at the pool-front recreation facility, every day feels like a vacation. Perfectly positioned for convenience, you are just 6 minutes from the 80+ retailers and restaurants at WINTER GARDEN VILLAGE, 18 minutes from the magic of WALT DISNEY WORLD, and only 30 minutes from Orlando International Airport. This home combines the security of a gated community, the luxury of recent high-end improvements, and the rare perk of Florida lake living. Call today to schedule a visit!
Listing is courtesy of: EXP REALTY LLC (407-706-5000)
Listing Agent: Daniel Betancourt (407-375-9142)
1672 MALCOLM POINTE DR, WINTER GARDEN, FL 34787
$519,900219 Days on yellowkey MLS ID: S5133690
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2035 Built: 2001Monthly Fee: $33 Tax: $6,403 (2024)Community: Tuscany Ph 02Single Family
Taxes:$6,403
Elementary School: Maxey Elem
High School: Ocoee High
Middle School: Lakeview Middle
Remarks: Golf cart district * Beautiful single-story home is nestled in a serene cul-de-sac in the heart of downtown Winter Garden.It is just an 8-minute drive to downtown Winter Garden, 5 minutes away from Publix, 10 minutes to Walmart, 14 minutes to target in winter garden village, easy access to SR-429 and Florida turnpike, offering exceptional convenience. This cozy 3-bedroom, 2-bathroom and an office can be an easy 4th bedroom. Modern single-story home provides 2,035 square feet of comfort and style. Fully renovated in 2022, featuring no carpeting throughout with dual offices, the kitchen has been updated with refinished cabinets and stainless steel appliances. Additionally, the roof and air conditioning were replaced in 2020, making it an ideal choice for buyers seeking a quick-move-in home!
Listing is courtesy of: MULTI CHOICE REALTY LLC (352-404-6542)
Listing Agent: Mingke Li (352-973-2303)
838 BETHUNE AVE, WINTER GARDEN, FL 34787
$275,00029 Days on yellowkey MLS ID: O6388596
REDUCED by $2,000 (0.7%) on 04/02/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 985 Built: 1961 Tax: $1,340 (2025)Community: Overstreet CrateSingle Family
Taxes:$1,340
Remarks: Welcome to this fully renovated 3-bedroom, 2-bath home on an oversized 0.20-acre lot in one of Winter Garden’s growing corridors. This move-in ready property offers immediate livability with long-term upside. Recent upgrades include a new AC system and water heater (2026) and a roof replaced in 2019, minimizing near-term capital expenses. The home features updated interiors and a functional layout suited for both owner-occupants and investors. The large lot provides flexibility for outdoor use and potential future enhancements. Zoned R-4, the property may provide additional possibilities for expansion or income-producing use. Buyer to verify all zoning and development options with the city. Located just minutes from major highways, shopping, and ongoing development, this property is well-positioned for both convenience and future growth.
Listing is courtesy of: LIVE MVRK LLC (407-756-4563)
Listing Agent: Gabriel Flete (407-341-9663)
13332 SUBURBAN TER, WINTER GARDEN, FL 34787
$749,900170 Days on yellowkey MLS ID: O6352569
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2706 Built: 1994 Tax: $2,841 (2024)Community: Citrus Cove Unit 01Single Family
Taxes:$2,841
Elementary School: Grassy Lake Elementary
High School: East Ridge High
Middle School: Windy Hill Middle
Remarks: Location, Location, Location! Welcome to 13332 Suburban Terrace, a stunning three-story contemporary home in the desirable city of Winter Garden, Florida. This residence offers 4 bedrooms and 3 bathrooms, combining comfort, functionality, and exceptional outdoor living. The first floor features a private in-law suite/studio with one bedroom, a full kitchen, and an open living/dining area—perfect for guests, extended family, or potential rental income. The second floor includes a bright living room, formal dining area, and a fully equipped kitchen with all stainless steel appliances, kitchen island, smooth glass electric cooktop, glass-canopy range hood, plus two bedrooms and one full bath. On the third floor, enjoy a spacious master suite with an en-suite bath and a family room overlooking the main living area. All windows and glass doors are hurricane-impact resistant insulated units (IGUs) for enhanced safety, energy efficiency, and year-round comfort—complete with a lifetime warranty. The outdoor area is a true entertainer's paradise, it showcase a beautiful pool, poolside cabana, bbq, bar, a generous space for dining, lounging and an expansive patio surrounded by lush landscaping and mature trees—ideal for relaxing, entertaining and hosting unforgettable moments with friends and family. Enjoy partial views of Lake Johns from the second-floor porch or kitchen window. Additional highlights include a two-car garage and an oversized driveway accommodating up to ten vehicles, a boat, or an RV. Located few minutes away from John’s Lake public boat ramp with access to beautiful county lakes and waterways—perfect for boating, fishing, and sunset cruises. Conveniently close to shopping, dining, top-rated schools, hospital, and major highways including Hwy 50 and the Florida Turnpike. Experience the best of Florida living just minutes from world-famous attractions and beaches. The seller is offering a $10,000 concession toward buyer's closing cost, discount points, or prepaids. Don't miss this opportunity. Schedule your private showing today!
Listing is courtesy of: NOVAK REALTY CORP (407-347-0114)
Listing Agent: Danilo Novak (407-832-2615)
107 TRADITIONS DR, WINTER GARDEN, FL 34787
$499,99519 Days on yellowkey MLS ID: S5145650
REDUCED by $24,980 (4.8%) on 04/01/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1582 Built: 1999Monthly Fee: $45 Tax: $1,458 (2024)Community: Traditions SubSingle Family
Taxes:$1,458
Elementary School: Dillard Street Elem
Remarks: You found it with this Location! The family will love this beautiful, Former Model home in Traditions! Blocks away from Downtown Winter Garden! Golf carts welcome! This 3/2 split plan has wood laminate flooring in living room & the master bedroom. Kitchen is open, Ceramic tile & eat-in space overlooking backyard. Master Bedroom is spacious with Walk-in shower and separate tub. Big backyard fully fenced. Enjoy the restaurants, famer's market & shops all in walking distance or use a golf cart! Separate Workshop room in garage- perfect for the handyman. AC 2019. Easy access to the turnpike, 429, 408 to downtown Orlando or OIA! Great Schools! Solar panels will be paid off at closing!
Listing is courtesy of: WATSON REALTY CORP (407-298-8800)
Listing Agent: Rick Evans, Ii (407-538-9295)
1710 E BAY ST, WINTER GARDEN, FL 34787
$254,99533 Days on yellowkey MLS ID: O6376343
REDUCED by $19,400 (7.1%) on 04/05/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 972 Built: 1957 Tax: $958 (2025)Community: Joe Louis Park First AddSingle Family
Taxes:$958
Remarks: WALK INTO $40,000+ OF INSTANT EQUITY! Appraised at $295,000 but priced for a lightning-fast sale at only $254,995, this fully renovated 3-bedroom, 2-bathroom Winter Garden home is the deal of the year. The seller must close before April 29, 2026, offering you a rare opportunity to secure a move-in-ready luxury property significantly below market value. This home provides total peace of mind with a BRAND NEW ROOF, new HVAC, and complete re-piping, all accented by a designer interior featuring large-format flooring, a gourmet kitchen, and spa-like bathrooms. Outside, the property shines with fresh stucco, a massive driveway, and a private fenced backyard, just minutes from the charm of Historic Plant Street. Best of all, this deal offers total financing flexibility: while the base price is set for a clean sale, the seller is happy to include any amount of closing cost credits or a furniture package by simply adjusting the price above $260,000. Act now to claim this built-in wealth before the deadline passes!
Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)
Listing Agent: Jose Villafana (407-705-8014)
2439 BALFORN TOWER WAY, WINTER GARDEN, FL 34787
$570,00037 Days on yellowkey MLS ID: O6386373
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2508 Built: 2008Monthly Fee: $243 Tax: $3,490 (2025)Community: Stoneybrook West DSingle Family
Taxes:$3,490
Remarks: *Video Tour Available!* Experience the best of Florida living in the heart of Stoneybrook West, where resort-style amenities and a true sense of community come together. Behind 24-HOUR GUARD GATED ENTRANCE, you’ll find everything you need to live like you’re on vacation year-round—an Olympic-sized swimming POOL, splash zone, FITNESS CENTER, playground, tennis, basketball and pickleball courts, a fishing pier, plus a PRIVATE BOAT RAMP on Black Lake. Even better, the quarterly HOA INCLUDES SPECTRUM INTERNET AND CABLE, making life here as convenient as it is enjoyable. Tucked away on a quiet CUL-DE-SAC STREET with no through traffic, this home offers both privacy and charm from the moment you arrive. Warm curb appeal welcomes you inside to rich WOOD FLOORS and soaring ceilings that create a light, airy Florida feel. At the front of the home, the FORMAL LIVING AND DINING ROOMS provide flexible space for entertaining or working from home, highlighted by a welcoming staircase. Designed for gathering, the OPEN FLOOR PLAN seamlessly connects the family room and eat-in kitchen. The kitchen features abundant QUARTZ COUNTERTOPS, upgraded cabinetry, and a pantry to keep everything organized. Double sliding doors from both the kitchen and family room open to a SCREENED PATIO OVERLOOKING A PEACEFUL POND—no rear neighbors, just tranquil views and evening sunsets. Upstairs, you’ll find the bedrooms along with a convenient laundry room. The primary suite is spacious with wood floors, double sinks, quartz countertops, a water closet, and WALK-IN CLOSET. The RENOVATED SECOND BATHROOM offers a beautifully tiled shower and tub with a built-in shampoo niche. Generously sized secondary bedrooms feature deep closets for all your storage needs. Additional upgrades include ceiling fans throughout the home and patio, a convenient half bath downstairs, new irrigation panel, updated faucets and shower head in the primary bath, newer microwave and refrigerator, window blinds and exceptional storage throughout. This is more than a home—it’s your opportunity to embrace the Florida lifestyle, where sunny days, waterfront adventures, and a vibrant community are all right outside your door.
Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)
Listing Agent: Tennille Biggers (850-628-4455)
5931 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787
$829,965199 Days on yellowkey MLS ID: G5102265
0 Days Off yellowkey (back on 9/18/2025)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2688 Built: 2026Monthly Fee: $150Community: Avalon WoodsSingle Family
Taxes:$0
Elementary School: Hamlin Elementary
Middle School: Hamlin Middle
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. The Anna Maria with Bonus floorplan is an expansive two-story home designed to accommodate a growing family, offering five bedrooms and three and a half bathrooms. On the main floor, you'll find a spacious great room adjacent to a well-appointed dining room and kitchen, creating an ideal space for gatherings. The primary suite, featuring a large walk-in closet and private bath, is thoughtfully positioned for privacy. An additional bedroom and a flexible bonus room on the second floor provide ample space for family members or guests.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
14255 HAMPSHIRE BAY CIR, WINTER GARDEN, FL 34787
$1,300,0002 Days on yellowkey MLS ID: O6395612
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4625 Built: 2003Monthly Fee: $141 Tax: $12,364 (2025)Community: Bay Isle 48 17Single Family
Taxes:$12,364
Elementary School: SunRidge Elementary
Remarks: One or more photo(s) has been virtually staged. NEW ROOF (2025) ~ TWO NEW A/C UNITS (2024) ~ and a NEW WATER HEATER (2024) headline this exceptional LAKEFRONT ESTATE on Black Lake, where recent RENOVATIONS and thoughtful design have transformed the home into a must see retreat designed to impress! Ideally situated behind the gates of Bay Isle in Winter Garden, this remarkable home is the cherry on top of 6.44 ACRES surrounded by lush mature trees and sweeping LAKE VIEWS, creating a peaceful personal oasis just minutes from everything. A paver driveway and COURTYARD ENTRANCE invite you into the residence, complemented by a split 3-car garage and beautiful architectural details that set the tone for what awaits inside. Spanning OVER 4,000 SQ FT of curated living space, the home blends timeless craftsmanship with a fresh, modern edge. Sleek PORCELAIN TILE and rich WOOD FLOORS flow throughout, while intricate DESIGN WORK and CUSTOM BUILT-INS add character and sophistication from floor to ceiling. Designed with both everyday living and entertaining in mind, the layout offers MULTIPLE LIVING AREAS & FLEX SPACES, and formal living and dining rooms, all positioned to maximize NATURAL LIGHT and capture the home’s breathtaking water views. Walls of windows pull the outdoors in, creating a light-filled atmosphere that highlights the beauty of the surrounding landscape! At the heart of the home, the GOURMET KITCHEN delivers everything a home chef could want and more. Outfitted with a gas range, gas oven, waterfall island, dual pantries for abundant storage, and a rare Doyon Etuve Proofer, the space is as functional as it is impressive, easily supporting everything from quiet dinners to large gatherings. Your MAIN FLOOR OWNER’S SUITE is a true retreat with tranquil views of Black Lake, a sitting area, a dedicated dressing space, and a beautifully designed modern en-suite bath that feels straight out of a home magazine. Throughout the rest of the home, additional bedrooms and flexible spaces offer endless possibilities for guests, offices, hobbies, or creative pursuits. Step outside and the lake lifestyle truly comes to life. MULTIPLE OUTDOOR LIVING SPACES invite you to relax, entertain, or simply take in the scenery, while the PRIVATE DOCK on Black Lake makes it easy to bring your boat and enjoy everything lakefront living has to offer. Despite the sense of seclusion, this home remains incredibly convenient to daily life. Shopping, dining, and major roadways including SR-429 are just minutes away, placing you close to Winter Garden’s vibrant charm, area attractions, and world-famous theme parks. Elegance personified, this extraordinary home delivers the privacy, style, and space you have been searching for. Bring your boat, embrace the lake life, and discover the lifestyle waiting for you in Bay Isle!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
730 RIVER GRASS LN, WINTER GARDEN, FL 34787
$649,90070 Days on yellowkey MLS ID: G5107248
0 Days Off yellowkey (back on 4/4/2026)
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2647 Built: 2014Monthly Fee: $72 Tax: $3,572 (2024)Community: Covington Chase Ph 2CSingle Family
Taxes:$3,572
Remarks: Welcome to life in the Winter Garden Golf Cart District, where you can cruise to Downtown Winter Garden’s shops, restaurants, and famous farmers market in minutes, then come home to a cul-de-sac beauty on a premium conservation lot with no rear neighbors. This stunning 5-bedroom, 3-bath home delivers the space, layout, and upgrades buyers dream about. Downstairs, you’ll find a full bedroom currently used as an office, perfect for guests, multigenerational living, or a private work-from-home suite, plus an additional flex space with double French doors for an ideal second workspace, playroom, or formal sitting room. Entertain in style in the formal dining room with tray ceiling, then gather in the heart of the home: a spacious kitchen featuring 42” wood cabinets, granite countertops, stainless steel appliances, and a massive island with breakfast bar, and yes, the stools stay! A sunny dinette/nook adds even more room for casual meals and morning coffee. The open-concept great room flows seamlessly from the kitchen, made for family game nights, movie marathons, and hosting the big game. Coming in from the garage, you’ll love the charming mudroom with cabinetry, ready for backpacks, purses, and the ultimate phone-charging station. And don’t miss the whimsical bonus: a “Harry Potter” closet under the stairs with shelving and tons of storage, perfect as a book nook, playhouse, or creative hideaway. Upstairs, retreat to a truly oversized primary suite with an en suite bath featuring double granite vanities, a soaking tub, and a separate double shower with two independent shower heads, plus his-and-hers closets. You’ll also find three additional bedrooms, another full bath, and an upstairs laundry room for everyday convenience. Step outside to your covered, screened patio, your new favorite place to unwind with a beverage at sunset or sip coffee while watching wildlife in the peaceful preserve behind you. The large lot offers plenty of space for a future pool, with the privacy of no rear neighbors. Major updates include: NEW roof (2025), NEW washer & dryer (2025), NEW oven & dishwasher (2023), a reverse osmosis drinking system, and a complete stainless-steel appliance package, including the refrigerator. All of this in a community with a pool and playground, and the West Orange Trail running through the neighborhood, perfect for biking, walking, and living the Winter Garden lifestyle. Conveniently located 5 minutes to 429 and the Turnpike, and approximately 25 minutes to Walt Disney World. Homes with this layout, this lot, and this location don’t last, so come see why this one feels like “the one.”
Listing is courtesy of: ASSIST2SELL BUYERS & SELLERS (352-289-6100)
Listing Agent: Karen Tefft (352-729-1227)
16230 CARRAWAY BAY ALY, WINTER GARDEN, FL 34787
$573,00069 Days on yellowkey MLS ID: NS1087076
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2474 Built: 2024Monthly Fee: $291 Tax: $2,273 (2024)Community: Waterleigh Ph 4B & 4CSingle Family
Taxes:$2,273
Remarks: Welcome to 16230 Carraway Bay Alley, a beautifully maintained home located in the heart of Winter Garden. Situated in a desirable community with convenient access to shopping, dining, and major highways, this property offers a perfect blend of comfort, style, and location. The home features a thoughtfully designed layout with spacious living areas, abundant natural light, and modern finishes throughout. The kitchen opens to the main living space, making it ideal for both everyday living and entertaining. The primary suite provides a private retreat with ample closet space and an en-suite bathroom. Enjoy low-maintenance living with outdoor space perfect for relaxing or hosting guests. Community amenities and nearby attractions enhance the lifestyle appeal, with close proximity to downtown Winter Garden, top-rated schools, and scenic trails. Convenient access to SR-429 and the Florida Turnpike makes commuting easy.
Listing is courtesy of: WATSON REALTY CORP (386-428-7355)
Listing Agent: Matthew Eads (804-651-6911)
16006 GILDEN WAY, WINTER GARDEN, FL 34787
$1,150,0009 Days on yellowkey MLS ID: O6392997
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3617 Built: 2023Monthly Fee: $225 Tax: $12,929 (2025)Community: Encore At OvationSingle Family
Taxes:$12,929
Remarks: Exquisite! Enjoy the experience of living in the finest of modern luxury in this "architecturally" designed estate. Situated in one of the Top Rated communities in Winter Garden, at Encore Ovation, on a 0.38-acre premium lot. Boasting over $200,000 in QUALITY UPGRADES, this residence features, five bedrooms and four bathrooms. Step onto the elegant 48 X 48 ceramic tiling that flows throughout the main level, transitioning to rich engineered hardwood on the second floor. A striking custom wood and TEMPERED glass staircase serves as a focal point, leading to a spectacular second floor entertainment gallery enclosed in TEMPERED glass with private balcony. A GOURMET DREAM KITCHEN , featuring custom wood cabinetry, Exotic Quartzite countertops, and a custom-fitted pantry. Equipped for the foodie enthusiast, with a SUB -ZERO refrigerator for peak freshness, a Wolf precision oven, a Thermador hub, and a dual-zone wine chiller, for years of gatherings and conversations. Retreat to the oversized travertine-floored lanai, overlooking a sprawling backyard already prepped with plumbing for a summer kitchen-the perfect. The perfect canvas for a custom infinity pool. Other features include;motorized designer blinds, custom lighting installations, and high-efficiency ceiling fans. A spacious garage with built-in overhead storage racks. HOA INCLUDES LAWN CARE AND BASIC LANDSCAPING, for true low-maintenance living.Enjoy resort-style community amenities just steps from your home.These include a clubhouse, fitness center, community pool and steps from a dog park and walking trails. End your day on your private Master Suite balcony, embracing breathtaking sunsets over Lake Mac. Welcome to paradise!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Renee Rodriguez (407-927-2055)
11145 HOLLOW BAY DR, WINTER GARDEN, FL 34787
$899,990111 Days on yellowkey MLS ID: O6367437
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3327 Built: 2025Monthly Fee: $200 Tax: $1,989 (2024)Community: WaterleighSingle Family
Taxes:$1,989
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. 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 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 an 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. This home is open for self-touring 7 days a week. *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)
11858 SHINE VIEW LN, WINTER GARDEN, FL 34787
$539,990184 Days on yellowkey MLS ID: O6349514
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2027 Built: 2025Monthly Fee: $190 Tax: $1,989 (2024)Community: WaterleighSingle Family
Remarks: Under Construction. Waterleigh presents the Cordale. This amazing all concrete block construction single-family home features 3 bedrooms and 2.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the home you’ll find a downstairs powder room and laundry room complete with doors for privacy. The well-appointed kitchen overlooks the family room, dining room, and oversized outdoor lanai. The kitchen features quartz countertops, stainless steel appliances, spacious walk-in pantry and an island with bar seating. Bedroom one is located off the living space in the back of the home for privacy. The bedroom one-bathroom impresses with double bowl vanities, toilet room with privacy door, shower/tub space, and spacious walk in closet. As we head up to the second floor, we are greeted with a loft area and two additional bedrooms. The upstairs bedrooms share a bathroom and linen closet for extra storage. This home features a two-car garage located at the rear of the home with drop zone as you enter the first floor. Like all homes in Waterleigh, the Cordale 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.*
13846 FRESH IVY ST, WINTER GARDEN, FL 34787
$649,900187 Days on yellowkey MLS ID: O6346706
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2108 Built: 2024Monthly Fee: $534 Tax: $2,180 (2024)Community: Del Webb Oasis Ph 3Single Family
Taxes:$2,180
Remarks: Welcome to 13846 Fresh Ivy Street, nestled in the highly desirable Winter Garden area, just minutes away from world-famous Orlando attractions. This home is easy on the eyes and offers the perfect blend of comfort, convenience, and luxury living. This beautifully designed two-bedroom, two-and-a-half-bath home features over 2,100 square feet of living space. With spacious interiors, thoughtful finishes, and modern upgrades, this home provides both style and functionality. Inside you will discover bright, open living areas, a gourmet kitchen, and bedrooms designed as your own personal sanctuary. Whether you’re hosting guests or enjoying a quiet evening at home, every detail has been styled with comfort in mind. Imagine mornings spent in the fitness center, afternoons sunbathing on a zero entry sun shelf by a cabana, and nights gathering with friends by the fire pits underneath the stars. This home and community is about freedom, fun, and comfort all in one place. This isn’t just a home, it’s the lifestyle you’ve earned.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
4918 WILDWOOD POINTE RD, WINTER GARDEN, FL 34787
$680,000295 Days on yellowkey MLS ID: S5129072
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2868 Built: 2015Monthly Fee: $172 Tax: $10,554 (2024)Community: Orchard Hills Ph 2Single Family
Taxes:$10,554
Elementary School: Keene Crossing Elementary
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: Located in the highly sought-after community of Orchard Hills, this stunning home offers the epitome of Central Florida living. Orchard Hills is a community that attracts buyers from all walks of life, making it an ideal investment. This spacious, single-story residence boasts 5 bedrooms, 3 full bathrooms, and one half-bath, ready for you to move in. From the moment you step inside, you'll be captivated by the expansive open spaces that flow seamlessly, creating a welcoming and bright ambiance. The well-thought-out design ensures that every corner of the home feels expansive and filled with natural light. The heart of this home is, without a doubt, its gourmet kitchen. Equipped with modern stainless steel appliances, gleaming granite countertops, and a generous center island, this kitchen is a chef's dream. Whether you're preparing a quick meal or hosting a large gathering, you'll have all the space and amenities you need. Adjacent to the kitchen, the ample living area provides the ideal space to relax and enjoy moments with your loved ones. Washer & Dryer do NOT convey. Click Virtual Tour 1 to visit the Property. Carpets removed, New Laminated Floors refresh up the living space.
Listing Agent: Carlos Hernandez Franquet (786-816-7138)
9354 LAKE HICKORY NUT DR, WINTER GARDEN, FL 34787
$1,099,00037 Days on yellowkey MLS ID: O6385808
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2278 Built: 1983 Tax: $3,375 (2025)Community: Hickory Lake EstatesSingle Family
Taxes:$3,375
Elementary School: Panther Lake Elementary
Remarks: Rare find on a tucked away street in the heart of it all. This lakefront home on Lake Hickory Nut, a 403-acre skiable and bass fishing lake in Winter Garden, offers approximately 100 feet of direct waterfront with no HOA and Disney Firework Views. Situated on an oversized lot with the ability to park boats or RVs, the property is set within a peaceful community surrounded by mature landscaping and spacious homesites. Enjoy breathtaking sunrise views over Lake Hickory Nut, with expansive water views visible throughout the house and on your private balcony. The lake is routinely tested by Orange County and is recognized as a high-quality lake in the area, offering exceptional water clarity and cleanliness providing year-round recreational enjoyment. The home is completely upgraded and renovated. Featuring new lighting, flooring, windows, doors, AC, well, plumbing, interior/exterior paint, epoxy garage flooring, kitchen, bathrooms, appliances, garage door, soffits, gutters, and a paver driveway, walkway, and patio. The living areas of this home bask in natural light, making it feel airy and bright. A wood-burning fireplace in the living room and oversized windows overlooking the lake create a warm and inviting space. The kitchen features an eat-in area that flows into a formal dining room and formal living room, providing flexibility for both entertaining and everyday living. A Florida room is lined with oversized windows and trim detail that maximize natural light and panoramic water views, with French doors leading to a paver patio along the shoreline. The private dock, built in 2018, includes covered and open seating areas ideal for relaxing, boating, or fishing. The first floor includes a bedroom with en-suite bath. Upstairs, double doors lead to an oversized primary suite with a private balcony overlooking the lake. The primary bath offers dual separate sinks and a spacious closet. A secondary upstairs bedroom features a window seat, and an additional full bathroom serves the second level. The upstairs is also prepped for a stackable laundry unit (in addition to the garage hookup) for added convenience. Ideally located near Horizon West, Hamlin Town Center, Downtown Winter Garden, and Orange County National Golf Center, this property offers a rare opportunity to own fully updated, skiable lakefront frontage in one of Central Florida’s most desirable locations.
Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)
Listing Agent: Matt Kester (772-494-8550)
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