Location: Winter Garden
Do Not Show Listings
7036 BOLANZO ALY, WINTER GARDEN, FL 34787
$475,000Listed 04/23/2026 10:13PM MLS ID: O6401429
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 1920 Built: 2024Monthly Fee: $188 Tax: $6,919 (2025)Community: MezzanoTownhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,919
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Welcome to this beautifully maintained, like new townhome located in the highly desirable Mezzano community in Winter Garden. Offering a thoughtful and versatile layout, this home combines modern features with comfortable living spaces throughout. The first floor features a spacious primary suite filled with natural light, complete with a large walk in closet and a sleek walk in shower in the ensuite bathroom. Just off the primary bedroom, enjoy your private front patio overlooking tranquil wetlands, the perfect spot for morning coffee or unwinding in the evening. A convenient half bath is also located on the main level for guests. The open concept living and dining areas provide flexible space for entertaining or everyday living, enhanced by upgraded lighting beyond the builder standard and elegant 9 foot ceilings that create an airy feel. Upstairs, you will find a generous loft area that can be used as a second living space, office, or playroom, along with a full laundry room for added convenience. The second floor also features a private double master bedroom suite with its own full bathroom, walk in closet, and beautiful views of the community pool and surrounding wetlands. Two additional bedrooms with standard closets and another full bathroom complete the upper level, offering plenty of room for family or guests. Enjoy additional outdoor space with a private rear patio situated between the home and detached garage, along with easy access to scenic walking paths that allow you to explore the community without needing to be on main roads. This home is ideally positioned within a short distance to the community pool and offers unique views of Magic Kingdom and EPCOT fireworks from both the bedroom and alley. Additional highlights include CAT5 wiring throughout, smart switch wiring in the primary bedroom and front exterior lighting, termite coverage for both ground and aerial protection, and a kitchen pot and pan rack that will remain with the home. The accent walls feature peel and stick wallpaper, allowing for easy customization. With abundant space both upstairs and downstairs, scenic surroundings, and a highly functional layout, this home offers a rare opportunity to enjoy comfort, convenience, and a touch of magic in one of Winter Garden’s most sought after communities.
Listing is courtesy of: SERHANT (786-296-8626)
Listing Agent: Lindsay Seibert (407-590-8687)
776 RAINFALL DR, WINTER GARDEN, FL 34787
$550,0001 Day on yellowkey MLS ID: O6400904
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2238 Built: 2007Monthly Fee: $92 Tax: $7,884 (2025)Community: Black Lake Park Ph 02Single Family
Taxes:$7,884
Remarks: GREAT LOCATION & LAKE VIEWS! Welcome to this immaculately maintained corner-lot gem, featuring 3 bedrooms plus a versatile Office/Den and 2 full bathrooms. The open-concept floor plan is designed for both elegant entertaining and comfortable daily living, flowing seamlessly from the formal living/dining area into a spacious family room. The gourmet kitchen is a chef’s dream, boasting granite countertops, a cooktop, built-in oven, and beautiful 42” cabinetry. Retreat to the private Master Suite—a true oasis featuring a generous walk-in closet, dual sinks, a garden tub, and a separate shower. Step outside to your covered rear patio to unwind and enjoy breathtaking lake views and sunsets. Located just minutes from Winter Garden Village and Historic Downtown, this upscale community offers unparalleled amenities: a private boat ramp on a skiable lake, fishing dock, community pool, tennis, basketball, soccer fields, and a playground. With easy access to the 429, 408, and Turnpike, your commute is a breeze. Don’t miss this opportunity—start living your best life today!
Listing is courtesy of: ONLI REALTY GROUP LLC (352-278-8544)
Listing Agent: Vinny Machado Da Silva (352-278-8544)
3430 TURNINGWIND LN, WINTER GARDEN, FL 34787
$825,000Listed 04/23/2026 9:47PM MLS ID: G5111151
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3358 Built: 2002Monthly Fee: $115 Tax: $6,001 (2024)Community: Windward Cay 48 125Spa: NoSingle Family
Taxes:$6,001
Elementary School: Keene Crossing Elementary
High School: Windermere High School
Tax Year: 2024
Middle School: Bridgewater Middle
Remarks: One or more photo(s) has been virtually staged. Looking for a pool home in Winter Garden that offers privacy and space, in a peaceful gated community? Well, welcome home! This beautifully upgraded home is close to schools, shopping, dining, golf, and quick access to the 429. Featuring 4 bedrooms, 4 bathrooms, a private office, two versatile bonus rooms, a large screened pool with water features, and a 3-car garage, it offers space for everyone. The long driveway and oversized paver pad provide parking for eight or more vehicles. The screened pool is over 6 feet deep and opens to a newly renovated pool bath, creating the perfect space for relaxing and entertaining year-round. With no rear neighbors, the backyard oasis backs to a tranquil conservation area and is framed by a wrought-iron fence with fragrant climbing jasmine for added privacy, and provides a green space for your furry friends. Inside, you’ll find wood-grain tile and high-quality bamboo flooring throughout—no carpet—plus a dramatic staircase with soaring ceilings and an elegant light fixture. The open kitchen is perfect for everyday living and entertaining, featuring new quartz countertops, a new sink and disposal, a newer stainless steel stove, microwave, and dishwasher, and a walk-in pantry with stylish new doors, all flowing into spacious living and dining areas. Downstairs, French doors lead to the office, while bi-fold doors connect to a flex room ideal for a gym, playroom, or guest suite. Upstairs, you’ll find three bathrooms, and two of the four bedrooms feature custom Closets by Design, along with a versatile flex space, perfect for a theater or family room. The oversized primary suite offers dual walk-in closets, extra storage, and a spa-like bath with soaking tub, separate shower, split vanities, and a private water closet. Recent updates include a new roof (2023), refreshed pool deck, new pool pump (2022), and new electric pool heater (2025). Additional upgrades include new lighting, updated hardware, fresh baseboards, new outlets and switches, coach lights, mirrors, and crown molding in the office, dining room, and primary suite. This is a home where comfort, style, and Florida living come together—ready to welcome you home.
Listing is courtesy of: CENTURY 21 HANCOCK (352-708-5650)
Listing Agent: Lydia Wells (352-708-5650)
837 GRANDE REGAL PT, WINTER GARDEN, FL 34787
$479,0001 Day on yellowkey MLS ID: O6400571
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1874 Built: 2002Monthly Fee: $60 Tax: $1,662 (2025)Community: Regal Pointe Ph 02 47/133Single Family
Taxes:$1,662
Remarks: Nestled in the highly sought after area of Winter Garden, this hidden gem presents the perfect blend of comfort, convenience, and charm. This well maintained home features three spacious bedrooms and two bathrooms, along with both a welcoming living room and a separate family room, ideal for entertaining or relaxing with loved ones. Centrally located, the property is just minutes from the hospital, shopping, dining, and all that Winter Garden has to showcase. Practically turnkey, the home boasts major updates including a 2019 roof, 2022 HVAC system, and a 2022 water heater, providing peace of mind for years to come. Step outside to your own private oasis, where a beautifully maintained yard is filled with a variety of fruit trees and plants, including avocado, banana, pigeon peas, lemon, pineapple, ginger, soursop, and much more, perfect for enjoying fresh homegrown produce. Do not miss the opportunity to own this unique and inviting home in a prime location!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Herna Quero (321-305-0916)
14501 GROVE RESORT AVE #2534, WINTER GARDEN, FL 34787
$225,000122 Days on yellowkey MLS ID: O6369252
REDUCED by $10,000 (4.3%) on 04/23/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1396 Built: 2018 Tax: $8,154 (2024)Community: Grove Residence & Spa Hotel Condo IiCondo
Taxes:$8,154
Remarks: VACATION Investment opportunity at The Grove Resort & Water Park, Orlando—welcome to Unit 2534. This fully furnished 3-bedroom, 2-bath CONDO-HOTEL is positioned in one of Central Florida’s highest-demand VACATION RENTAL communities. The spacious Jasmine floor plan sleeps 8 and includes a king suite, two queen beds in the guest room, and a pull-out sofa in the living room. Designed for durability and guest appeal, the unit features quartz countertops, stainless steel appliances, in-unit laundry, and an oversized screened balcony overlooking tranquil resort and conservation views. AS A SHORT-TERM RENTAL PROPERTY, owners are allowed personal use up to 179 days a year, with full on-site property management available to handle bookings, housekeeping, maintenance, and guest services year-round. This hassle-free model makes it ideal for out-of-state, international investors, or active vacation home investors seeking passive income. The Grove Resort is a full-service destination featuring Surfari Water Park with lazy river and FlowRider surf simulator, three additional pools, Lake Austin access for water sports and fishing, fitness center, arcade, indoor glow mini golf, restaurants, bars, spa, and 24-hour concierge. Daily Disney shuttles and proximity to major attractions that drive strong guest occupancy. HOA fee covers all utilities, including electric, water, cable, WiFi, pest control, and insurance—offering predictable, streamlined costs for owners. With high rental demand, professional management, and a below-market price point, this unit offers strong ROI potential in a market with continued tourism growth. Act now to capitalize on this prime income-producing asset in the heart of Orlando’s booming short-term rental zone. Agents, please Realtor's remarks for details.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Jackie Cavada-Barrero (407-443-7776)
16329 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787
$490,000187 Days on yellowkey MLS ID: O6353551
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2070 Built: 2021Monthly Fee: $284 Tax: $5,869 (2024)Community: Hawksmoor Ph 3Townhouse
Taxes:$5,869
High School: Horizon High School
Middle School: Water Spring Middle
Remarks: Welcome to this stunning corner-unit townhome in the heart of Winter Garden, where natural light, extra space, and thoughtful design come together to create the perfect place to call home! As you step inside, you'll be greeted by a welcoming foyer that leads into an open-concept layout. From there, you’ll approach the beautifully designed modern kitchen and spacious dining area that flows seamlessly into the gathering room, ideal for entertaining or everyday living. On the first floor, you’ll find a versatile fourth bedroom with a closet, offering flexibility for guests, a home office, or a playroom. You’ll also love the spacious breezeway that adds both elegance and function to the layout, while upstairs, bedrooms 2 and 3 are connected by a convenient Jack-and-Jill bathroom. The end-unit location provides added privacy and extra green space; plus, knowing this home has been beautifully maintained with a roof (2021), water heater (2021), and AC unit (2021)—all in excellent condition, gives peace of mind. Beyond the home itself, the community offers an incredible lifestyle with resort-style amenities such as a pool, splash pad, clubhouse, gym, pet-friendly parks, soccer field, playground, scenic walking trails, a covered picnic area, regular social events, and more. Located just minutes from Hamlin Town Center, top-rated schools, shopping, dining, and parks within the vibrant Horizon West community—one of Central Florida’s fastest-growing and most desirable areas—this home truly has it all. Don’t miss your opportunity to own this beautifully maintained, move-in-ready corner-unit townhome. Schedule your showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Erica Jefferson (414-248-9118)
14766 ELLINGSWORTH LN, WINTER GARDEN, FL 34787
$1,099,00039 Days on yellowkey MLS ID: O6390518
0 Days Off yellowkey (back on 4/23/2026)
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4661 Built: 2018Monthly Fee: $210 Tax: $14,115 (2025)Community: Oxford ChaseSpa: YesSingle Family
Taxes:$14,115
Elementary School: SunRidge Elementary
High School: West Orange High
Middle School: SunRidge Middle
Remarks: Welcome to this beautifully upgraded 5 bedroom, 4 and a half bath pool and spa home located in the highly desirable, fully gated community of Oxford Chase! Zoned for top-rated schools, this home offers the perfect combination of luxury, privacy, and energy efficiency. This spacious residence features a 3-car garage, paver driveway, and impressive curb appeal. Inside, you’ll find thoughtfully designed living spaces including a formal dining room with a custom built-in bar, perfect for entertaining guests or hosting special occasions, multiple office spaces, upgraded flooring throughout, a large laundry room, private gated doggie retreat, and so much more. The primary suite is located on the first level, secluded for optimal privacy with oversized his and hers closets. Upstairs you'll find guest bedrooms, a large open air loft space, and plush movie theatre room. Step outside to your own gorgeous backyard oasis featuring a fully enclosed heated pool and spa, ideal for year-round Florida living. The backyard overlooks a peaceful green space with no rear neighbors, providing extra privacy and relaxing views. Enjoy outdoor entertaining with the fully equipped summer kitchen featuring a custom vented hood, perfect for grilling and gatherings. The home is also equipped with PAID IN FULL SOLAR PANELS offering incredible energy efficiency and the benefit of little to no electric bill. Located in a secure gated neighborhood close to top schools, shopping, dining, and major highways, this home truly has it all — privacy, premium upgrades, and resort-style outdoor living. Schedule your showing today!
Listing Agent: Jenna Palmero (407-697-8727)
13813 PEACH ORCHARD WAY, WINTER GARDEN, FL 34787
$850,00017 Days on yellowkey MLS ID: O6392351
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3793 Built: 2018Monthly Fee: $190 Tax: $7,249 (2025)Community: Orchard Pk/Stillwater Xing PhSingle Family
Taxes:$7,249
Remarks: Amazing & spacious executive home with 5 bedrooms, 4 and a half bathrooms, with no rear neighbors in the beautiful Orchard Park community located in Winter Garden and just minutes from both Hamlin Town Center and Winter Garden Village. Upon entering this immaculate home you will be impressed with its open and spacious floor plan that offers a downstairs guest room and bathroom, Living Room, Dining Room, Family Room and an amazing kitchen with 42" Cabinets, granite counter tops, ss appliances, oversized center island and massive pantry. The first floor offers neutral oversized tile floors, a half bath, a drop zone area located just off the kitchen and garage and sliders from the breakfast area onto the covered screened patio with paver patio extension and fire pit. The upstairs offers an oversized Primary Suite with 5 piece bathroom including double vanities, a guest room with private bath and two additional bedrooms that share a hall bathroom. The large upstairs Laundry Room makes doing laundry convenient. The community offers a Private Community Swimming Pool, Sports field and Playground. Conveniently located near major roadways and shopping and minutes from the Walt Disney World Resort.
Listing Agent: Randall Gill (407-756-0071)
15306 GILLIGAN CT, WINTER GARDEN, FL 34787
$925,0007 Days on yellowkey MLS ID: O6399653
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3127 Built: 2020Monthly Fee: $102 Tax: $8,308 (2025)Community: Winding Bay Ph 1BSpa: NoSingle Family
Taxes:$8,308
Elementary School: Water Spring Elementary
Remarks: Set within one of Winter Garden’s most sought-after communities, this thoughtfully designed two-story home offers a lifestyle defined by ease, connection, and everyday enjoyment. This 4-bedroom, 3.5-bath home with over 3,000 square feet features an open floor plan with a gourmet kitchen and a large island, perfect for both everyday living and entertaining. The main level includes a dedicated den/office, while the second floor offers a spacious loft, along with a fourth bedroom and full bath—ideal for guests or multi-generational living. Tree-lined sidewalks, friendly neighbors, nearby parks, and resort-style amenities create a setting that feels both relaxed and vibrant, while top-rated schools, convenient access to shopping and dining, and close proximity to Walt Disney World Resort. Positioned on arguably one of the BEST lots in the community, this home sits at the end of a quiet cul-de-sac with breathtaking, unobstructed pond and tree-lined views that create a peaceful and private backdrop. Inside, the home showcases extensive upgrades and thoughtful design throughout, including a kitchen with 42-inch cabinetry and additional custom upper cabinets, GE Profile appliances, and a seamless flow into the main living space highlighted by two expansive tri-sliders opening to the outdoor oasis. Custom floor-to-ceiling drapery adds elegance, while upgrades such as 8-foot doors throughout, level 4 wood-look tile flooring, upgraded carpet with 8-pound padding, 5 1/4-inch baseboards, and 7 1/4-inch shiplap accents in the hallway, kitchen, tech nook, and primary bedroom elevate the interior. Additional features include custom plantation shutters on the first floor, upgraded glass doors in the front den/office, Cat 6 wiring throughout with pre-wiring for PoE security cameras, and a new alarm system with wireless sensors on all doors and windows. The home has been meticulously maintained with quarterly HVAC servicing, gutters installed since purchase, and a freshly painted exterior completed in 2025 using upgraded Sherwin Williams 25-year paint. Step outside to a private outdoor retreat featuring fresh landscaping, a fully fenced side yard, a privacy-enhancing podocarpus hedge, and custom paver walkways with additional space for storage. The backyard feels like a private Central Florida escape, where an 18,000-gallon resort-style saltwater pool serves as the true centerpiece, complete with a lounging platform overlooking the serene pond and tree-lined backdrop. The pool is thoughtfully designed with sealed pavers, a striking midnight blue interior finish, a fountain with dual deck jets, two multicolor LED lights, and a Pentair smart system for remote control, all professionally serviced weekly. The screened enclosure allows for year-round enjoyment, while the community dog park directly across the street adds everyday convenience for pet lovers. From the upstairs loft and bedrooms, enjoy views of Disney fireworks, adding a magical touch to everyday living. This move-in ready home is prepared for its next chapter, with community amenities that include a resort-style pool, oversized cabana, sports fields, playground, sidewalks, and a dog park. More than just beautifully upgraded, this home offers a rare opportunity to own a meticulously maintained, design-forward property in a premier location, delivering both luxury and lifestyle in one exceptional package—a place to settle in, build memories, and truly feel at home in Winter Garden.
Listing is courtesy of: REAL ESTATE HOUSE FL INC (407-484-0005)
Listing Agent: Gretchen Carlson (407-484-0005)
17224 OLD COUNTRY LN, WINTER GARDEN, FL 34787
$2,099,00058 Days on yellowkey MLS ID: O6384075
REDUCED by $101,000 (4.6%) on 04/16/2026
Bed: 6 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3629 Built: 1980 Tax: $9,822 (2024)Community: Lake Avalon Groves RepSingle Family
Taxes:$9,822
Elementary School: Hamlin Elementary
Middle School: Hamlin Middle
Remarks: A rare opportunity for a completely renovated home in rural Avalon Groves and no HOA. Situated on 2.5 private acres, this beautifully remodeled farmhouse inspired estate offers peaceful country living with modern comfort and thoughtful design throughout. This spacious home features 6 bedrooms and 3.5 bathrooms and has been extensively updated within the last year. New septic tank added (now making 2 septic tanks in 2026). New roof. Tankless hot water heater. Brand new gates and fencing. The interior offers open living spaces filled with natural light, high quality finishes, and top of the line appliances throughout. Every detail has been carefully selected to create a warm and welcoming atmosphere while maintaining functionality for everyday living. The primary suite serves as a private retreat, highlighted by an expansive bathroom that is comparable in size to a bedroom. Designed for comfort and relaxation, this space offers both luxury and privacy. Outdoors, the property continues to impress with a private pool and generous acreage providing flexibility for a variety of uses. Dedicated boat and RV storage offers added convenience for those who enjoy an active lifestyle. Two separate private gated entrances provide enhanced accessibility and privacy. This property presents a rare opportunity to enjoy acreage living while still benefiting from modern updates and refined finishes in the Rural Avalon Groves area, while being only 5 minutes away from all your shopping, restaurants and groceries.
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Kerstin Crow (615-428-7046)
15527 SWEET ORANGE AVE, WINTER GARDEN, FL 34787
$700,00028 Days on yellowkey MLS ID: O6394429
Bed: 3 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2383 Built: 2017Monthly Fee: $118 Tax: $5,959 (2025)Community: Highlands/Summerlake Grvs Ph 1Single Family
Taxes:$5,959
Elementary School: Summerlake Elementary
Remarks: Experience refined living in this truly one-of-a-kind single-story residence, offering over 2,300 square feet of thoughtfully designed space. This exceptional home features three spacious bedrooms, three full bathrooms, and an additional half bath, along with a private office or den enclosed by elegant French doors—perfect for working from home or quiet retreat. Designed for both comfort and sophistication, the home boasts soaring 10-foot ceilings and striking tray ceilings in the foyer, great room, and primary suite. The open-concept living area is enhanced by extended tile flooring, creating a seamless and upscale feel throughout. At the heart of the home, the gourmet kitchen impresses with a large center island, stylish pendant lighting, and effortless flow into the main living and dining spaces. Enjoy the best of indoor-outdoor living with two screened-in lanais—one just off the kitchen and the other connected to the family room—accessible through dual sets of sliding glass doors. Home features tankless gas water heater, gas range and outdoor gas hookup for grilling. Additional highlights include a rare tandem three-car garage, a functional drop zone with built-in cabinetry and counter space, and charming curb appeal with a welcoming front porch—perfect for relaxing with your favorite drink. Nestled in the highly sought-after Horizon West area of Winter Garden, this home offers unmatched convenience. You’re just minutes from Walt Disney World, premier shopping and dining, Orange County National Golf Center, and the charm of Historic Downtown Winter Garden. With easy access to major highways including 429, I-4, and the Florida Turnpike, commuting is effortless. Residents enjoy access to outstanding community amenities, including a resort-style pool, playgrounds, dog park, tennis courts, and more. Whether you’re searching for a primary residence, vacation home, or investment opportunity, this property offers the perfect blend of luxury, functionality, and location.
Listing is courtesy of: BUYER REBATES REALTY (407-629-2300)
Listing Agent: Sean Popat (407-399-1669)
12731 GROVEHURST AVE, WINTER GARDEN, FL 34787
$620,00079 Days on yellowkey MLS ID: O6379203
REDUCED by $24,900 (3.9%) on 04/20/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3474 Built: 2006Monthly Fee: $111 Tax: $8,378 (2025)Community: Grovehurst A-DSingle Family
Taxes:$8,378
Remarks: One or more photo(s) has been virtually staged. Ideally located in the heart of Winter Garden, this home offers 3,474 sq. ft. of living space and exceptional walkability just steps from Winter Garden Village’s shopping, dining, and everyday conveniences. Recent updates include new carpet and fresh interior and exterior paint. The flexible floor plan features five bedrooms, three full bathrooms, and a kitchen with 42-inch upper cabinets, granite countertops, and an open layout to the family room with a large eat-in area. Stone Crest community amenities include a clubhouse, pool, tennis/pickleball courts, playground, and a scenic walking trail around a tranquil pond. With close proximity to AdventHealth, major highways, historic downtown Winter Garden, the West Orange Trail, and top-rated schools, this property provides excellent convenience and connectivity.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY (407-203-0007)
Listing Agent: Joseph Doher (407-203-0007)
8031 NAVEL ORANGE LN, WINTER GARDEN, FL 34787
$675,0009 Days on yellowkey MLS ID: O6399594
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2298 Built: 2015Monthly Fee: $82 Tax: $8,090 (2025)Community: Summerlake GrvsSingle Family
Taxes:$8,090
Remarks: Welcome to this exquisitely appointed residence, gracefully positioned on a private corner lot with no neighboring home on one side, offering a rare sense of seclusion and tranquility. The outdoor living space is thoughtfully designed, featuring an inviting patio ideal for refined entertaining or quiet relaxation. A freshly painted exterior (2024) enhances the home’s sophisticated curb appeal. Inside, the bespoke kitchen is a true centerpiece, showcasing custom finishes, under-cabinet lighting, a sleek glass tile backsplash, and a suite of recently upgraded appliances including a new dryer, dishwasher, disposal, and range. The formal living room is bathed in natural light from expansive windows and offers exceptional versatility, perfect as an elegant home office or curated hobby space. This residence effortlessly blends timeless style with modern convenience. Residents of Summerlake enjoy access to an array of resort-caliber amenities, including a clubhouse, pool, tennis courts, playground, parks, and scenic walking trails. Ideally situated near top-rated schools, upscale shopping, fine dining, major thoroughfares, and Orlando’s premier attractions, this exceptional home presents a rare opportunity to experience elevated living at its finest.
1075 CHASE DR, WINTER GARDEN, FL 34787
$625,00053 Days on yellowkey MLS ID: O6386607
1 Days Off yellowkey (back on 4/23/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2125 Built: 2015Monthly Fee: $41 Tax: $2,734 (2024)Community: Island Pointe SubSingle Family
Taxes:$2,734
Remarks: Under contract-accepting backup offers. Welcome to 1075 Chase Drive-located in downtown Winter Garden, just minutes from the charm and energy of Plant Street. This rare, newer-construction single-story home offers a blend of modern comfort and timeless style that’s sure to impress. As you enter, custom tile in the foyer sets the tone, with a versatile flex room to the right—perfect for a home office, formal dining room, playroom, or whatever suits your lifestyle.The open-concept design seamlessly connects the kitchen, dining, and family areas, creating an ideal space for entertaining. The large kitchen island is perfect for cooking, casual meals, or hosting friends and family. Sliding glass doors open to create an effortless indoor-outdoor living experience—perfect for those quintessential Florida days. The split floor plan offers privacy, with the primary suite serving as a true retreat, complete with high ceilings, a double vanity, and a spa-like shower. On the opposite side of the home, you’ll find three additional spacious bedrooms, each with plantation shutters and high end laminate flooring. After a long day, unwind on your fully screened back porch with space for multiple seating areas, or head to the side yard to tend your garden. The thoughtfully designed outdoor living space offers plenty of room for grilling, dining, and relaxing—an entertainer’s dream. Just minutes from your front door, Winter Garden’s vibrant Plant Street awaits, offering an award-winning farmer’s market, local dining, boutique shopping, art galleries, Crooked Can Brewery, the West Orange Trail, and year-round festivals.This is a rare opportunity to own a beautifully crafted home in one of Winter Garden’s most desirable neighborhoods—where modern living meets small-town charm. Call for your private showing today.
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Katie Bray (407-779-6677)
17005 ARROWHEAD BLVD, WINTER GARDEN, FL 34787
$615,0003 Days on yellowkey MLS ID: O6401039
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1655 Built: 1983 Tax: $5,400 (2025)Community: Arrowhead LakesSingle Family
Taxes:$5,400
Remarks: Florida lake front charm. 11 minutes to Disney World. Pristine spring fed lake. A2 zoning. A+ schools. No HOA. Nice layout inside out, established neighborhood. Major updates have been done within the last 10 years. Please see realtor remarks for details or call the listing agent. Move in ready, cosmetic updates would be the icing on the cake.
Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-299-3000)
Listing Agent: Dan Lu (407-454-3601)
15659 JUNGLE ALY, WINTER GARDEN, FL 34787
$435,00034 Days on yellowkey MLS ID: S5143684
INCREASED by $75,000 (20.8%) on 04/23/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1732 Built: 2021Monthly Fee: $203 Tax: $6,265 (2024)Community: Winding Bay Ph 2Townhouse
Taxes:$6,265
Remarks: Seller motivated. Beautifully maintained town home 3 bed and 3 bath in the desirable Horizon West area of Winter Garden! This charming alley-facing property features an open-concept floor plan with spacious living and dining areas, a modern kitchen with solid surface countertops, stainless steel appliances, and a large island perfect for entertaining. Upstairs offers generously sized bedrooms, including a private primary suite with walk-in closet and an-suite bath. Enjoy low-maintenance outdoor living with a private patio and rear-entry garage. Conveniently located near top-rated schools, shopping, dining, and major roadways. A fantastic opportunity to own in one of Central Florida’s most sought-after communities! Offers may be entered ONLINE through Tuesday, April 14, 2026 at 3:00 pm. AT SELLER'S DISCRETION, A SUBMISSION MAY BE ACCEPTED AT ANY TIME.
Listing Agent: Dinorah Navarro (407-625-7522)
15543 PEBBLE RIDGE ST, WINTER GARDEN, FL 34787
$645,900553 Days on yellowkey MLS ID: O6250356
2 Days Off yellowkey (back on 4/23/2026)
REDUCED by $3,900 (0.6%) on 04/17/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3359 Built: 2001Monthly Fee: $233 Tax: $8,538 (2023)Community: Stoneybrook WestSpa: NoSingle Family
Taxes:$8,538
Elementary School: Whispering Oak Elem
Tax Year: 2023
Remarks: Under contract-accepting backup offers. Popular Stoneybrook West Subdivision - A gated golf community with 2255 homes. 2 Story, 4 Bedrooms, 3 Full Baths. Master is upstairs, huge bedroom, with walk in closet and master bath. A large 27x24 Bonus room over 3 Car Garage. One bedroom with guest bath downstairs also LR, DR, FR, Kitchen and Laundry. Off the master bedroom is a 12x22 Deck overlooking the screened pool and golf course. Nice quiet street also. The seller will give an allowance for new flooring & kitchen appliances, so buyer can pick their favorite colors.
Listing is courtesy of: RE/MAX SELECT GROUP (407-352-5800)
Listing Agent: Paul Mcgarigal (407-352-5800)
4122 SHEPPERDS HOLLOW ALY, WINTER GARDEN, FL 34787
$554,990112 Days on yellowkey MLS ID: O6370363
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2459 Built: 2021Monthly Fee: $281 Tax: $8,150 (2024)Community: Enclave/HamlinSingle Family
Taxes:$8,150
Elementary School: Independence Elementary
Remarks: Welcome to the Enclave at Hamlin, one of Winter Garden’s desirable communities, featuring the popular Taylor Morrison Ashwood floor plan that blends style, space and versatility. This beautifully designed two-story home offers two bedrooms, 2.5 baths, a spacious loft that can be converted into a third bedroom and a private one-bedroom with kitchenette garage apartment, providing exceptional flexibility for multi-generational living, guests or potential rental income. Upon entry, you are greeted by a welcoming foyer that opens into an expansive great room, ideal for entertaining and everyday living. Overlooking the space is the gourmet kitchen, complete with a large island, quartz countertops, stainless steel appliances and ample cabinetry. The kitchen flows seamlessly to the covered lanai, creating an ideal indoor-outdoor living experience. Also on the first floor is versatile flex space that can be used as a home office, formal dining room or additional bedroom. Upstairs, the primary suite serves as a private retreat, featuring a spa-inspired bath with dual quartz vanities, a walk-in shower, private water closet and a generous walk-in closet. The second floor also includes a secondary bedroom, a full bath with tub/shower combination, a private laundry room and a loft with built-in features, ideal for a playroom, craft room, media space or easily converted bedroom. Adding tremendous value is the one-bedroom, one-bath garage apartment with kitchenette, walk-in closet and private entrance, offering an excellent income opportunity or private accommodations for guests or family. The HOA maintains the lawn, including areas inside the fenced yard, providing a low-maintenance lifestyle. Community amenities include a resort-style pool with cabana overlooking Lake Hartley, a tot lot and peaceful open recreation areas with benches positioned to capture scenic lake views. The location is exceptional, with a quick half-mile experience, bike ride or visit to Hamlin, a vibrant 900-acre destination featuring a luxury theater, shopping, dining, salons, waterfront restaurants and entertainment. Convenient access to SR 429, theme parks, and major roadways makes commuting easy. Residents will also enjoy being within distance of the anticipated Horizon West Regional Park, a 215-acre destination park under development. Once complete, the park will offer miles of scenic trails, playgrounds, picnic pavilions, open green spaces, a splash pad, lake access for kayaking and community event areas, delivering an outstanding outdoor lifestyle right outside your door. This home offers a combination of comfort, convenience and future-forward living in one of Winter Garden’s fastest-growing areas.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-581-7888)
Listing Agent: Teresa White (904-994-9075)
328 BAYSIDE AVE, WINTER GARDEN, FL 34787
$445,0007 Days on yellowkey MLS ID: O6396654
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1235 Built: 1986Monthly Fee: $7 Tax: $5,354 (2025)Community: Kings BaySingle Family
Taxes:$5,354
Elementary School: Dillard Street Elem
Middle School: Lakeview Middle
Remarks: Under contract-accepting backup offers. Welcome to easy Florida living in this charming 3-bedroom, 2-bath ranch-style home, perfectly positioned on a spacious corner lot in one of Winter Garden’s most desirable areas. With its single-story layout and inviting curb appeal, this home offers both comfort and convenience in a relaxed, open setting. Step inside to discover a bright and functional floor plan designed for everyday living and effortless entertaining. The generous living spaces flow seamlessly, while ample natural light enhances the home’s warm and welcoming feel. The split-bedroom design provides privacy, with a well-appointed primary suite and comfortable secondary bedrooms. Outside, the oversized corner lot offers endless possibilities—plenty of room for outdoor gatherings, gardening, or simply enjoying the Florida sunshine. Located well within the golf cart district, you’re just a short ride from the charm and energy of historic downtown Winter Garden. Enjoy easy access to local shops, dining, community events, and the popular weekly farmers market, all just minutes from your doorstep. This is a rare opportunity to own a beautifully situated home that combines classic ranch-style living with an unbeatable location. Call Today!
Listing is courtesy of: SOUTHERN HERITAGE REALTY, INC (407-877-6928)
Listing Agent: Jim Kernohan (407-450-3861)
11045 BOSTWICK ALY, WINTER GARDEN, FL 34787
$590,000239 Days on yellowkey MLS ID: O6337436
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2292 Built: 2023Monthly Fee: $245 Tax: $9,031 (2024)Community: Waterleigh Ph 4ASingle Family
Taxes:$9,031
Remarks: SELLER MOTIVATED AND PRICE IS INCLUDING TRANSFERRABLE SOLAR PANELS PAID BY THE SELLER! This amazing single family home located in most desirable prime location in winter garden has it all, from privacy with no back up neighborhood to the front porch facing beautiful landscaping view just few steps from the Elementary school and all the resort amenities The home has solar panel for extra energy saving and the seller will take care of remaining balance. All concrete block construction on both first and second floor 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’ll find the first bedroom complete with ensuite bathroom and a powder room across the hall. The well-appointed kitchen overlooking the great room, dining room, and oversized outdoor lanai. The kitchen features granite countertops, stainless steel appliances, spacious walk-in pantry and an island with bar seating. As we head up to the second floor, we are greeted with a loft area and additional three bedrooms. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity sinks and separate toilet area. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. Your laundry room is located on the second floor for convenience. This home features a two car garage located at the rear of the home with drop zone as you enter the first floor. Waterleigh community is well know for prime location with a lot of lifestyles amenities such Playgrounds & Sports Fields, Indoor Fitness Centers, Scenic Lakes and Ponds, Community Garden Mini-Golf, Walking & Nature Trails, Beach Volleyball & Hammock Beach This beautiful 4 bedrooms 3 bathrooms and 1 half bathroom is built with All Concrete Block Construction, Smart Home Technology, Quartz Counters, Professional Lawn Maintenance Included, Publix Grocery in Community, Local Shops, Restaurants & Cinema Nearby Located just minutes from downtown Winter Garden. This prime location with this particular meticulous home is great spot that leads you to enjoy easy access to a vibrant array of shops, restaurants, and entertainment options. The historic downtown area offers charming boutiques and family-owned eateries, while the nearby Winter Garden Village provides a more modern shopping experience with over 100 retailers.
Listing is courtesy of: EPIQUE REALTY, INC. (888-893-3537)
Listing Agent: Khadija Webber (407-592-2166)
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