Location: Winter Garden
Keyword(s): West Orange High
Keyword(s) High School: West Orange High
Do Not Show Listings
17379 CHANNEL WAY, WINTER GARDEN, FL 34787
$689,00010 Days on yellowkey MLS ID: O6412749
REDUCED by $10,000 (1.4%) on 06/05/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2782 Built: 2019Monthly Fee: $215 Tax: $9,049 (2025)Community: Waterside At Johns LakeSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,049
Elementary School: Hamlin Elementary
High School: West Orange High
Tax Year: 2025
Middle School: Hamlin Middle
Remarks: Large 4-bedroom home + 2 large Bonus rooms. This 2782sf 7-year-old home is in the awesome community of Lakeside just west of the Winter Garden Village about 4 miles. The home has tons of space, humungous kitchen and Master bedroom downstairs along with bedroom #2 and 3, and with a full bath. The first floor is gorgeous tile from the front door throughout up to the bedrooms. Coffered details in high ceilings, arched openings and a back yard looking over a green retention area. This Hampshire plan has a split plan with 2 bedrooms and full bath near the front of the house first floor. Walking past the flex room that can be used for formal dining, office, etc to the main open living area with living, dining, and kitchen. The kitchen is large with TONS of tall 42 inch raised panel cabinetry and walk-in pantry. The beautiful light brown speckled granite is accented by medium Brown cabinets and all stainless-steel appliances with the stove fueled with gas. A walk-in pantry and Island sink with breakfast bar look out to the open living room and dinette. Dinette has large windows on 3 sides to embrace the outside nature. The main living area has a 3-panel slider door to open wide to the paved, covered Lania that overlooks a good-sized back yard with a large field retention area beyond. Past the living room through the arched entry into the large primary bedroom. Ceiling fan and high coffered detailed ceilings and a huge bath with a seated walk-in shower separating two individual vanities on large cabinets for lots of storage. Large walk-in closet, separate toilet room, and linen closet. Washer and dryer have their own room near the garage. Take a quick step upstairs to a HUGE open loft, 4th bedroom and 3rd full bath. full bath. This home has a 2 car garage and gas heated Tankless water heater. This home is located in the awesome community of Waterside at Johns lake, with an incredible huge pool lakeside, playground, dock, clubhouse, state-of-the-art fitness center
Listing is courtesy of: SPRING REALTY ONE LLC (407-340-1754)
Listing Agent: Chun Cai (951-699-4983)
13212 SOCIAL LN, WINTER GARDEN, FL 34787
$595,00058 Days on yellowkey MLS ID: O6398708
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2526 Built: 2005Monthly Fee: $100 Tax: $4,474 (2025)Community: Regency Oaks FSpa: NoSingle Family
Taxes:$4,474
Elementary School: SunRidge Elementary
Middle School: SunRidge Middle
Remarks: One or more photo(s) has been virtually staged. SEVERAL PHOTOS HAVE BEEN VIRTUALLY STAGED !Welcome to this beautifully updated 4-bedroom, 2.5-bath home in the highly sought-after Regency Oaks community. Thoughtfully upgraded for long-term peace of mind, this residence features a newly replaced roof, a 2023 HVAC system (both indoor and outdoor units), and a 2023 water heater—major improvements that add exceptional value and confidence for the next owner. Step inside to discover a bright, open floor plan with luxury vinyl flooring throughout, offering durability, modern style, and easy maintenance. The remodeled kitchen showcases sleek modern cabinetry and quartz countertops, creating a fresh, contemporary space perfect for everyday living and entertaining. The spacious primary suite provides a comfortable retreat, complemented by three additional bedrooms ideal for family, guests, or a home office. With two full bathrooms and a convenient half bath, the layout is designed for both functionality and comfort. Enjoy Florida living at its best with a screen-enclosed patio and a fully paved backyard, offering a low-maintenance outdoor oasis perfect for gatherings, grilling, or quiet relaxation. Located just 15 minutes from Universal Studios and Disney Parks and less than a 2-minute walk to AdventHealth, this home is perfectly positioned for both families and professionals. Regency Oaks offers resort-style amenities including a sparkling pool, clubhouse, tennis courts, playground, and a scenic park—enhancing the lifestyle experience beyond your front door. This move-in-ready home combines modern upgrades, unbeatable convenience, and exceptional community features—an outstanding opportunity to enjoy the best of Winter Garden and Orlando living.
Listing is courtesy of: PMI PRIME HOME (407-218-7598)
Listing Agent: Jianlin Shi (407-988-5057)
17422 CHANNEL WAY, WINTER GARDEN, FL 34787
$767,000109 Days on yellowkey MLS ID: G5108709
1 Days Off yellowkey (back on 6/8/2026)
REDUCED by $7,000 (0.9%) on 05/11/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3261 Built: 2019Monthly Fee: $215 Tax: $9,958 (2025)Community: Waterside On Johns LakeSpa: NoSingle Family
Taxes:$9,958
Remarks: Welcome to this beautifully maintained 5-bedroom, 3-bathroom home offering comfort, space, and versatility for modern living. With a thoughtfully designed floor plan, this home is perfect for families, multigenerational living, or anyone needing extra space for a home office or guest rooms. The open living areas are filled with natural light and provide a welcoming atmosphere for both everyday living and entertaining. The kitchen offers ample cabinetry and counter space, flowing seamlessly into the dining and living areas, ideal for gatherings and family meals. The primary suite features a private bathroom and generous closet space, creating a relaxing retreat. Additional bedrooms are well-sized and flexible, perfect for children, guests, or work-from-home needs. Three full bathrooms ensure comfort and convenience for everyone. Outside, enjoy a private backyard with plenty of room for outdoor entertaining, play, or relaxation. Whether you envision weekend barbecues, a garden, or a peaceful outdoor escape, this space delivers. Conveniently located near schools, shopping, dining, and major roadways, this home combines space, comfort, and location, ready for its next owner to make it their own. Serious buyers welcome. Schedule a showing today!
Listing is courtesy of: LIST NOW REALTY, LLC (352-385-7636)
Listing Agent: Matt Buttner (352-385-7636)
205 HORSTFIELD DR, WINTER GARDEN, FL 34787
$315,00022 Days on yellowkey MLS ID: O6410222
REDUCED by $7,500 (2.3%) on 06/08/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1048 Built: 1998Monthly Fee: $40 Tax: $1,983 (2025)Community: Park Ave EstatesSingle Family
Taxes:$1,983
Middle School: Lakeview Middle
Remarks: **WINTER GARDEN SINGLE FAMILY HOME** **HVAC (2023) + ROOF (2018) + EXTERIOR PAINT (2024)** **ALL NEW ENERGY EFFICIENT WINDOWS & SLIDING DOOR (2025)** **LARGE FULLY FENCED PRIVATE BACKYARD** **NATURAL GAS** **TILE THROUGHOUT -- NO CARPET** Welcome to this adorable, affordable & move-in-ready single family home in the PERFECT LOCATION. Purchase with CONFIDENCE & PEACE OF MIND…recent updates & special features include: all new energy efficient windows and sliding door (2025), updated kitchen cabinetry (2018), updated bathroom vanities (2024), roof (2018), HVAC (2023), freshly painted exterior (2024), new garage opener (2023), custom hurricane shutters for windows & doors, fully fenced (2022)…and MORE! NO CARPET -- tile throughout the entire home. Lots of NATURAL LIGHT throughout. The fantastic & FLEXIBLE floor plan features a large living space open to the kitchen, THREE bedrooms, TWO full bathrooms -- all one ONE LEVEL. The primary suite includes a large walk-in shower, updated vanity and walk-in closet with shelving. All appliances STAY -- including washer & dryer. Enjoy the Florida lifestyle outdoors with the extended paver patio and large backyard space that is fully fenced & private with additional open community easement behind the home for added privacy buffer. Extended driveway for ample parking space. LOW UTILITY BILLS with newer roof, HVAC & windows! The LOW HOA includes a community pool. The PERFECT location -- conveniently located to both Winter Garden & Clermont with easy direct access to the FL Turnpike (less than three miles) and HWY 429 (less than two miles). Just ONE MILE to historic Downtown Winter Garden -- enjoy the West Orange Trail, HUGE weekly farmer's market, festivals, shopping, dining, art, the Crooked Can Brewery & Plant Street Market. Easy access to ALL shopping (Costco, Target & more), dining, medical & conveniences in both Winter Garden & Clermont along HWY 50 and Winter Garden Village. WELCOME HOME!
Listing is courtesy of: TARA MOORE REAL ESTATE (407-738-5588)
Listing Agent: Tara Moore (407-765-3700)
420 E CYPRESS ST, WINTER GARDEN, FL 34787
$425,00012 Days on yellowkey MLS ID: O6412414
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1616 Built: 1950 Tax: $5,517 (2025)Community: Overstreet CrateSingle Family
Taxes:$5,517
Elementary School: Maxey Elem
Remarks: Welcome to this stunning, fully renovated and fully furnished home, perfectly situated on an oversized lot in one of Winter Garden's most exciting and rapidly growing areas. Whether you're looking for a primary residence, a turnkey investment, or a second home, this move-in-ready property offers the perfect blend of comfort, style, and convenience. Inside, you'll find an open-concept floor plan filled with natural light, featuring all-new flooring, recessed lighting throughout, energy-efficient double-pane windows, and a beautifully updated kitchen complete with stainless steel appliances. Major improvements include a new roof and a 3.5-ton AC system, providing peace of mind for years to come. Step outside and enjoy the spacious, fully fenced backyard, offering plenty of room for entertaining, pets, play, or simply relaxing outdoors. Located just one mile from Historic Downtown Winter Garden, you'll enjoy easy access to award-winning dining, shopping, farmers markets, and community events, all while living in a welcoming, family-friendly neighborhood. Fully furnished, beautifully updated, and truly move-in ready, this home offers a rare opportunity to enjoy all that Winter Garden has to offer from day one.
Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)
Listing Agent: Trevor Zwick (863-303-6114)
483 PENNSYLVANIA AVE, WINTER GARDEN, FL 34787
$339,90060 Days on yellowkey MLS ID: O6398208
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1008 Built: 1988 Tax: $2,702 (2025)Community: East Garden Manor Add 03Single Family
Taxes:$2,702
Remarks: Move in ready, completed renovated, property offers two bedrooms and 2 bathrooms, brand new bathrooms, brand new kitchen, new appliances, new windows, ceramic trough the house, new roff, new pluming, close to major roads, schools, minutes to Winter Garden dawn town.
Listing is courtesy of: STIRLING INTERNATIONAL REAL ES (407-250-1000)
Listing Agent: Rosa Rodriguez (407-832-1185)
205 SURPRISE DR, WINTER GARDEN, FL 34787
$1,200,000191 Days on yellowkey MLS ID: O6365188
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2171 Built: 1950 Tax: $3,406 (2024)Community: Winter Garden Shores RepSingle Family
Taxes:$3,406
Elementary School: Dillard Street Elem
Tax Year: 2024
Remarks: PRICE ADJUSTED to reflect recent appraisal, this four-lot parcel presents immediate value- with two vacant lots ready for expansion, additional income potential, or future development. Discover an exceptional property in the heart of highly desirable GOLF CART DISTRICT of Winter Garden. Situated on an expansive four-lot parcel totaling 3/4 of an acre, this unique estate offers unmatched space, charm and potential with NO HOA- all within short distance to the 22 mile long West Orange Trail, Winter Garden Farms Market, Plant Street dining, shopping and breathtaking sunsets over Lake Apopka. This beautifully maintained three-bedroom, two-bath home features an office with custom wood built-ins and a light-filled breezeway framed in windows, perfect for a sunroom or additional living space. Gorgeous hardwood floors flow throughout, and the newly renovated bathroom showcases modern, floor-to-ceiling tile for a luxurious touch. Storage is abundant, including an oversized two-car garage with a half bath, ideal for hobbyist or future conversion opportunities. Outside, the property transforms into a private oasis featuring a sparkling heated saltwater pool, outdoor fireplace and lush mature landscaping complete with fruit trees - all fully fenced for privacy. Two of the four lots are currently vacant, offering potential to subdivide, expand, or build. A large shed, rated as a detached garage, on the property provides additional space for a workshop or equipment storage. There is ample room for all your recreational toys; golf-cart, boat, and more. The current owners also have plans for a kitchen renovation and poolside wraparound porch, which they are willing to share with the buyer - opening the door to greater customization. Whether you're seeking a serene retreat, developmental potential, or the charm of downtown Winter Garden living, this property is truly one of a kind. This private paradise location is a convenient commute to Downtown Orlando, Disney and other Orlando attractions. You're dream estate awaits.
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Alison Scorsone (321-689-3554)
914 TROWMAN ALY, WINTER GARDEN, FL 34787
$649,00018 Days on yellowkey MLS ID: O6410871
REDUCED by $26,000 (3.9%) on 06/02/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1642 Built: 2022Monthly Fee: $356 Tax: $6,421 (2025)Community: Oakland ParkSingle Family
Taxes:$6,421
Elementary School: Tildenville Elem
Remarks: One or more photo(s) has been virtually staged. Nestled in the highly sought-after Oakland Park community, this beautifully maintained 3-bedroom, 3-bath home is the definition of move-in ready living. Featuring desirable upgrades throughout, including gas appliances, elegant plantation shutters, and a turnkey design, this home offers the perfect blend of comfort, style, and convenience. Enjoy open-concept living spaces filled with natural light, spacious bedrooms, and a layout designed for modern living and entertaining. Pride of ownership shines in every detail, making this home truly stand out. Located in a charming golf cart community with resort-style amenities, residents enjoy access to parks, schools, walking trails, and more. Just minutes from vibrant Downtown Winter Garden, you'll love being close to the award-winning farmers market, lively festivals, boutique shopping, dining, and entertainment. This is your opportunity to own a well-maintained, upgraded home in one of Winter Garden's most desirable communities!
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erica Diaz (407-897-5400)
940 MARSH REED DR, WINTER GARDEN, FL 34787
$779,99061 Days on yellowkey MLS ID: O6397274
REDUCED by $20,000 (2.5%) on 05/13/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3493 Built: 2015Monthly Fee: $128 Tax: $10,543 (2025)Community: Johns Lake PointeSpa: NoSingle Family
Taxes:$10,543
Remarks: One or more photo(s) has been virtually staged. Welcome to 940 Marsh Reed Drive, a beautifully upgraded 5 bedroom, 3 bathroom, SOLAR HEATED POOL HOME offering just under 3,500 square feet of well-designed living space in the highly sought-after Johns Lake Pointe community! Additional OFFICE and LOFT / BONUS ROOM. Solar panels are paid off! From the moment you arrive, the home makes a strong impression with its tile roof, enhanced landscaping, and well manicured appearance, setting the tone for what’s inside. The interior opens to a bright, expansive layout with high ceilings, neutral finishes, and multiple living and dining areas designed for both everyday comfort and entertaining. The heart of the home is the open-concept kitchen, featuring abundant cabinetry, walk-in pantry, granite countertops, stainless steel appliances, extended butler's pantry style prep area, and a large center island that flows seamlessly into the main living area. Natural light fills the space, creating an inviting atmosphere that connects effortlessly to the indoor and outdoor living areas. The first floor dedicated office provides the ideal work-from-home setup or can easily function as a flex space to suit your needs. Upstairs, a spacious loft/bonus area offers additional versatility—perfect for a media room, playroom, or secondary living space. The primary suite is generously sized and features tray ceilings, large windows, and a relaxing, private feel. The en-suite bathroom includes dual vanities, a walk-in shower, walk-in closet, and ample storage, creating a comfortable retreat at the end of the day. Step outside to your private backyard oasis, where the SCREENED-IN POOL and covered lanai deliver the ultimate Florida lifestyle. The pool is equipped with SOLAR HEATING for year-round enjoyment and a NEW POOL PUMP for efficiency. A standout feature is the $7,000 integrated smart exterior lighting system, including the pool enclosure, creating a stunning nighttime ambiance perfect for entertaining. Additional upgrades include a new gutter drainage system and overhead garage storage racks, offering both convenience and functionality. Located in Johns Lake Pointe, residents enjoy access to resort-style amenities including a community pool, fitness center, playground, and sports courts, all while being just minutes from major highways, shopping, dining, Winter Garden's Historic Plant Street, and everything Central Florida has to offer. Only a short drive to Disney! Close to HIGH-RATED SCHOOLS. This is a rare opportunity to own a move-in ready home that combines space, upgrades, and lifestyle in one exceptional package. Call now for your private showing!
Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)
Listing Agent: Andrew Kincaid (407-304-0454)
15326 JOHNS LAKE POINTE BLVD, WINTER GARDEN, FL 34787
$1,385,00015 Days on yellowkey MLS ID: S5150851
1 Days Off yellowkey (back on 6/5/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3495 Built: 2014Monthly Fee: $128 Tax: $7,670 (2025)Community: Johns Lake PointeSpa: YesSingle Family
Taxes:$7,670
Remarks: Under contract-accepting backup offers. Welcome to luxury lakefront living on the shores of sought-after Johns Lake. Perfectly positioned with breathtaking west-facing sunset views, this fully upgraded waterfront residence offers the ultimate blend of elegance, comfort, and resort-style outdoor living in one of Winter Garden’s most desirable communities. Featuring nearly 3,500 square feet on 1 floor of thoughtfully designed living space, this exceptional home showcases 4 bedrooms, 3.5 bathrooms, a 3-car garage, premium hardwood flooring, and a gourmet chef’s kitchen with high-end finishes, upgraded cabinetry, and expansive entertaining space. Designed to maximize the waterfront lifestyle, the home seamlessly transitions outdoors to a private backyard retreat complete with a sparkling pool, oversized spa, outdoor kitchen, and stunning panoramic lake views — the perfect setting for sunset entertaining year-round. Additional highlights include a newer roof and HVAC systems (approximately 3 and 5 years old), luxurious updated interiors, spacious living areas. This rare Johns Lake opportunity combines elevated style with effortless move-in-ready convenience. With premium designer furnishings negotiable. Making this a possible true turnkey opportunity. Located within the highly sought-after Johns Lake Pointe community, residents enjoy proximity to historic downtown Winter Garden, top-rated schools, shopping, dining, major highways, and Orlando’s world-class attractions. Experience the best of Central Florida lakefront living in a home where every evening ends with unforgettable sunsets over Johns Lake.
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Carlos Facchinat (407-433-8109)
15187 HARROWGATE WAY, WINTER GARDEN, FL 34787
$435,00058 Days on yellowkey MLS ID: TB8497081
REDUCED by $10,000 (2.2%) on 06/06/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1296 Built: 2003Monthly Fee: $46 Tax: $5,808 (2025)Community: Stone CrkSingle Family
Taxes:$5,808
Elementary School: Whispering Oak Elem
Remarks: Location! Location! Welcome to this wel maintained 3 beds 2 bath single family home located in the desirable community of Stone Creek in Winter Garden. This home offers a spacious living room, dining area, spacious master bedroom with double sink and walking closet, 2 extra bedrooms and sharing bath, 2 car garage, screened porch and generous fenced back yard. This property is convenient located near shops, restaurants, and the highly rated Elementary School is located inside the community with walking distance. Also, near Winter Garden village Mall, Stonybrook West Golf Club, Tucker Ranch Wellness Park (in construction) And easy acces to the Highway and Airport.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Maria Howard (410-422-3518)
16746 TURTLE HATCH DR, WINTER GARDEN, FL 34787
$1,265,00024 Days on yellowkey MLS ID: O6406556
1 Days Off yellowkey (back on 6/6/2026)
Bed: 6 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4451 Built: 2018Monthly Fee: $215 Tax: $9,540 (2025)Community: Waterside/Johns Lk-Ph 1Single Family
Taxes:$9,540
Remarks: Behind the gates of the Waterside community in Winter Garden, this exceptional residence offers a rare blend of luxury, thoughtful design, and modern functionality. Built in 2018, this beautifully upgraded 6 bedroom, 4.5 bathroom home spans 4,451 square feet and includes a spacious 3 car garage, all positioned within one of Winter Garden’s most desirable gated communities. From the moment you enter through the charming front courtyard entrance, the home showcases refined finishes, expansive living spaces, and an open concept layout designed for both everyday comfort and upscale entertaining. A dramatic two story entry and soaring two story great room create an impressive first impression, while abundant natural light pours throughout the home enhancing the warm yet elegant atmosphere. Additional architectural details including crown molding, tray ceilings, and elegant rod iron stair railings further elevate the design. The gourmet kitchen serves as the centerpiece of the home featuring quartz countertops, a designer tile backsplash, vent hood, gas range, double convection ovens, oversized island, abundant cabinetry, built-in desk area, and an expansive eat in kitchen area ideal for both casual dining and entertaining family and guests. The thoughtfully designed first floor features a spacious primary suite highlighted by tray ceilings, ceiling fan, dual walk in closets, and a spa inspired ensuite bathroom complete with dual sinks, granite countertops, garden tub, and a luxurious walk-through shower with dual shower heads. A private guest suite with its own ensuite bath and tile glass enclosed walk in shower offers the perfect setup for visitors or multi generational living. A dedicated office with double door entry, elegant formal dining room with tray ceiling, expansive great room, convenient half bath, and exceptional storage throughout further enhance both the functionality and sophistication of the home. Upstairs, the second floor features four additional bedrooms, two additional bathrooms, and a spacious bonus room with double door entry complete with a private balcony overlooking the backyard, creating the perfect retreat for entertaining, relaxing, or family gatherings. Outdoor living is equally impressive with a covered rear patio featuring pavers and ceiling fan, offering the perfect place to relax or entertain while enjoying the privacy of having no rear neighbors. The property also offers ample space to create your dream pool and outdoor entertaining area. Additional highlights include a tankless water heater, window blinds throughout, crown molding, and the home is prewired for a future outdoor kitchen. Neighborhood amenities include a community pool, recreational facilities, and playground. Located within gated Waterside, residents enjoy a private and exclusive atmosphere while remaining just minutes from top rated schools, shopping, dining, Disney, downtown Winter Garden, and major roadways including the 429, Turnpike, and 408. This is more than a home, it is a lifestyle defined by space, craftsmanship, privacy, and location in one of Central Florida’s premier communities
Listing is courtesy of: CLOCK TOWER REALTY (407-832-7332)
Listing Agent: Jennifer Mitchell (803-414-1133)
14411 HAMPSHIRE BAY CIR, WINTER GARDEN, FL 34787
$895,0008 Days on yellowkey MLS ID: O6413972
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4010 Built: 2005Monthly Fee: $182 Tax: $11,924 (2025)Community: Bay Isle 48 17Spa: YesSingle Family
Taxes:$11,924
Remarks: Nestled within the prestigious gated enclave of Bay Isle, this distinguished Toll Brothers home offers a rare combination of sophisticated design, thoughtful craftsmanship, and resort-caliber amenities — all within walking distance of Winter Garden Village and AdventHealth. A soaring two-story foyer and grand living room welcome you with an abundance of natural light streaming through an exceptional array of windows — a hallmark of the home's open, airy character. At the heart of the home lies a commanding gourmet kitchen, completely updated in 2021 with quartz countertops, a handsome marble backsplash, and a professional-grade induction cooktop with custom hood vent. Rich cherry cabinetry, a wall oven, built-in microwave, generous center island, and extensive counter space are all finished with elegant crown molding — flowing seamlessly into the expansive family room with French doors opening to the outdoor living area. The main-level primary suite is a true sanctuary, featuring rich laminate flooring, serene pool and spa views, and architectural transom windows that elevate the abundant natural light. Two oversized walk-in closets with custom built-in organization systems flank a luxurious en-suite bath complete with a dual-sink vanity, deep soaking tub, and a spa-inspired walk-in shower. Upstairs, three additional bedrooms offer both privacy and connection. A private en-suite bedroom with generous walk-in closet is discreetly separated via a catwalk, while two additional bedrooms share a well-appointed Jack-and-Jill bath with individual vanity areas and a shared water closet and tub/shower. Your private home theater is fully equipped for the ultimate cinematic experience — theater seating, a 4K HD projector, Dolby surround sound, all convey with the home. The space also offers flexibility as a fifth bedroom. A loft game area and additional half bath complete the upper level's entertainment suite. Step outside to your private oasis: a sparkling pool and spa enclosed within an oversized screened lanai, complete with an outdoor shower and multiple seating areas ideal for effortless outdoor entertaining. An additional state of the art Clearlight 2 person infrared sauna provides relaxation, and rejuvenation. A three-car split garage — two bays connected to the main home, a third independently accessed — provides exceptional versatility for a workshop, boat storage, collector vehicles, or extra storage. A dedicated EV charging station is already in place. Eight-foot interior doors and extensive crown molding throughout reinforce the home's refined aesthetic. New roof (2019) · Pool pump (2018) · Full kitchen renovation (2021) Bay Isle's gated grounds feature a park, playground, walking trail, and a fishing pier on Black Lake — offering a tranquil, connected lifestyle just minutes from major roadways and every amenity Winter Garden has to offer.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Julie Bettosini, Pa (321-689-9594)
1651 AMSEL FALLS PARK TER, WINTER GARDEN, FL 34787
$1,080,0008 Days on yellowkey MLS ID: O6414027
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3881 Built: 2017Monthly Fee: $184 Tax: $6,540 (2025)Community: TwinwatersSingle Family
Taxes:$6,540
Remarks: Welcome home to this beautifully maintained 4-bedroom, 3 full bath, residence in sought-after Twinwaters. Featuring a designer kitchen with full-extension soft-close drawers and cabinets, 10-foot ceilings on the main level, 9-foot ceilings upstairs, crown molding, and central vacuum, this home offers both comfort and thoughtful upgrades throughout. Enjoy peaceful views of the expansive conservation area from your backyard with no rear neighbors, creating a private and relaxing setting. Professionally designed landscaping provides year-round color and fragrance, while local songbirds add to the natural charm. On clear evenings, catch a glimpse of Disney fireworks from home. Conveniently located just minutes from historic Downtown Winter Garden, shopping, dining, and premier golf destinations including Orange County National. Complete with a spacious 2-car garage, this warm and inviting home is ready for its next owner. Schedule your private showing today!
Listing is courtesy of: FOLIO REALTY LLC (407-917-0241)
Listing Agent: Jennifer Dollar (407-252-3762)
1437 SCARLET OAK LOOP, WINTER GARDEN, FL 34787
$350,0008 Days on yellowkey MLS ID: O6411620
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1684 Built: 2014Monthly Fee: $300 Tax: $3,213 (2025)Community: Tucker OaksTownhouse
Taxes:$3,213
Remarks: Don't miss this opportunity to own a well-maintained townhome in the sought-after gated community of Tucker Oaks. Featuring 3 bedrooms, 2.5 bathrooms, a 2-car garage, this home offers the perfect blend of comfort, convenience, and value. The open floor plan provides spacious living and dining areas, ideal for both everyday living and entertaining. A major recent improvement includes a roof installed in 2025, offering added peace of mind for years to come. Residents enjoy an array of community amenities, including a clubhouse, community pool, park, and playground. Ideally located just minutes from Historic Downtown Winter Garden, the West Orange Trail, shopping, dining, and major commuter routes including SR 429 and the Florida Turnpike, this home offers low-maintenance living with convenient access to everything Winter Garden has to offer.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Amy Moline (407-506-7447)
1219 SADDLEBACK DR, WINTER GARDEN, FL 34787
$1,050,0008 Days on yellowkey MLS ID: O6412381
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2667 Built: 2022Monthly Fee: $215 Tax: $11,474 (2025)Community: Oakland Parkb-1Spa: NoSingle Family
Taxes:$11,474
Remarks: Welcome to what may be the most impeccably maintained and beautifully upgraded home in Oakland Park! This stunning 4-bedroom, 3.5-bath residence showcases designer-inspired finishes throughout, featuring soaring ceilings, modern color palettes, and countless custom enhancements that make it truly one of a kind. Built just four years ago and nestled on a quiet street directly across from green space, this exceptional David Weekley Seaside model offers the perfect blend of elegance, comfort, and convenience. The thoughtfully designed floor plan features a luxurious first-floor owner's retreat complete with a spacious spa-like bath, while the additional bedrooms, study, dining area, and generous living spaces provide room for everyone to spread out and enjoy. No detail has been overlooked. The current owners have invested extensively in premium upgrades, including custom wood trim and accent walls, designer wallpaper, upgraded lighting throughout, custom Zebra window shades, professionally designed closets in the owner's suite, secondary bedroom, and laundry room, plus a water softener, gutters, epoxy-coated garage floors, updated landscaping, and an inviting paver patio. Both the interior and exterior have been freshly painted, creating a truly move-in-ready experience. Step outside to the screened rear porch, where you'll enjoy peaceful mornings, evening breezes, and endless opportunities for birdwatching and outdoor dining. The spacious 3-car garage provides ample storage and functionality for today's lifestyle. Beyond the home itself, Oakland Park offers an award-winning lifestyle unlike any other. This celebrated Parade of Homes community is known for its charming streetscapes, abundant green spaces, waterfront gathering areas, parks, and strong sense of community. Golf-cart-friendly and ideally located just minutes from the West Orange Trail, you'll also enjoy the convenience of walking or riding into vibrant downtown Winter Garden for exceptional dining, shopping, entertainment, and year-round events. This is more than a home—it's a lifestyle defined by luxury, connection, recreation, and the timeless charm of Winter Garden Living.
Listing is courtesy of: CENTRAL FLORIDA PRIME REAL ESTATE LLC (407-404-4041)
Listing Agent: Lynette Piontek (407-222-4310)
14755 MASTHEAD LANDING CIR, WINTER GARDEN, FL 34787
$580,00030 Days on yellowkey MLS ID: O6408082
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2258 Built: 2004Monthly Fee: $253 Tax: $8,397 (2025)Community: Stoneybrook WestSpa: NoSingle Family
Taxes:$8,397
Remarks: Located in the highly desirable Stoneybrook West community, this beautifully maintained 4-bedroom, 2-bath home offers the perfect blend on comfort, style, and convenience. Featuring a newer roof installed in 2019, brand-new 2025 central air conditioning system, newer refrigerator, new range/oven, and new dishwasher. The home welcomes you with abundant natural light, an open concept layout, and spacious living areas enhanced by attractive laminate flooring throughout. One of the home's standout features is the serene pond view from the screened lanai. With four bedrooms and versatile living spaces, this home easily accommodates families of all sizes.
Listing is courtesy of: SUSANA JORDAN STUTSMAN (321-278-0334)
Listing Agent: Susana Stutsman (321-278-0334)
2450 DAHLGREN WAY, WINTER GARDEN, FL 34787
$1,700,000103 Days on yellowkey MLS ID: TB8481106
REDUCED by $250,000 (12.8%) on 05/20/2026
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4365 Built: 2007Monthly Fee: $225 Tax: $8,970 (2024)Community: Bronsons Lndgs F & MSpa: YesSingle Family
Taxes:$8,970
Remarks: Rare Gated Lakefront Retreat with Grandfathered Boat Access on Lake Luntz Discover resort-style living in this one-of-a-kind gated lakefront home in the heart of Winter Garden. Nestled on a quiet, tree-lined cul-de-sac, this 5-bedroom, 5-bathroom, 4,365 Sq Ft home offers a smart layout designed for both everyday living and entertaining. The first-floor bedroom and full bath are ideal for guests or multi-generational living, while upstairs includes a loft, media room, and three additional bedrooms, including one en-suite and a Jack-and-Jill setup. Enjoy endless lake views from the screened pool with grotto seating and waterfall, or entertain indoors in the Florida Grill/Bar room featuring a refrigerator, freezer, deep fryer, griddle, bar sink, dishwasher, and full pool/guest bath. The primary suite is a true retreat with double walk-in closets, spa-style bath, garden tub, walk-in shower, and dual water closets. Lake enthusiasts will love the boathouse, covered dock, and boat lift, complete with power and water, along with multiple watercraft options including a pontoon slip (~20’), jet ski slip for 2, power lifts, and additional space for non-powered boats. Additional bonus spaces include a garage under air with a separate gym/rec room. Outdoor living abounds with a beachfront-style area, wood-burning fireplace, granite bar-top seating, and spectacular sunset views. This is a rare opportunity to own the only home on Lake Luntz with grandfathered boat access, offering a private lakefront lifestyle you won’t find anywhere else.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Keegan Siegfried (813-670-7226)
1061 PORTMOOR WAY, WINTER GARDEN, FL 34787
$535,0009 Days on yellowkey MLS ID: G5113349
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1804 Built: 2001Monthly Fee: $243 Tax: $6,801 (2025)Community: Stoneybrook West 44/134Single Family
Taxes:$6,801
Remarks: Welcome to 1061 Portmoor Way, a single-story 4-bedroom, 2-bathroom home located in the highly desirable Stoneybrook West community—a 24-hour manned, guard-gated golf community known for its resort-style living. This home features inviting modern living spaces that flow seamlessly to a fully fenced backyard with a patio, creating the perfect setting for outdoor relaxation and entertaining. New Roof installed in 2020, water heater installed in 2022, stainless steel appliances, modernized kitchen, tiled floor in kitchen, bathrooms and laundry room. Residents of Stoneybrook West benefit from an outstanding amenity lifestyle, including 24-hour security, a clubhouse, fitness center, resort-style pool, tennis, basketball and volleyball courts, playground, fishing dock, and a boat ramp with access to Black Lake. The community is also home to Stoneybrook West Golf Club and SB Prime restaurant and bar. HOA dues include internet and Spectrum TV, offering added convenience and value. Ideally located minutes from Winter Garden Village, downtown Winter Garden, and SR-429, this home provides easy access to shopping, dining, entertainment, and everyday essentials while still offering a peaceful, gated community setting.
Listing is courtesy of: ENGEL & VOLKERS CLERMONT (407-905-6700)
Listing Agent: Lisa Reed (407-509-7995)
2123 PORTCASTLE CIR, WINTER GARDEN, FL 34787
$389,00011 Days on yellowkey MLS ID: O6412643
0 Days Off yellowkey (back on 6/4/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1606 Built: 2006Monthly Fee: $46 Tax: $5,857 (2025)Community: Stone Creek Unit 4Single Family
Taxes:$5,857
Remarks: One or more photo(s) has been virtually staged. Welcome to your family's next home in the highly desirable Stone Creek community of Winter Garden. This spacious two-story residence features 4 bedrooms, 2.5 bathrooms, and a versatile upstairs loft, perfect for a home office, playroom, or additional living space. Step inside to an open-concept living and dining area with stylish flooring throughout—no carpet throughout! The thoughtfully designed floor plan offers all four bedrooms upstairs, providing privacy and separation from the main entertaining areas. The spacious primary suite features an en-suite bathroom with dual vanities and a walk-in closet. Conveniently located downstairs, you'll find the laundry room and a half bath for guests. Families will appreciate being zoned for Whispering Oak Elementary School, a National Blue Ribbon School and one of the highest-rated schools in the Orlando area. Enjoy an unbeatable location just minutes from Winter Garden Village, Hamlin Town Center, and historic Downtown Winter Garden, with easy access to State Road 429 and the Florida Turnpike. Plus, Disney World and Orlando's top attractions are only a short drive away. Don't miss this opportunity to own a beautiful home in one of Winter Garden's most sought-after communities.
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