Location: Winter Garden , 34787
Do Not Show Listings
3407 CURRENT AVE, WINTER GARDEN, FL 34787
$699,0001 Day on yellowkey MLS ID: O6400102
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3747 Built: 2020Monthly Fee: $152 Tax: $10,520 (2025)Community: Lakeview PreserveSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,520
Elementary School: Lost Lake Elem
High School: East Ridge High
Tax Year: 2025
Middle School: Windy Hill Middle
Remarks: Five bedrooms, four and a half baths, and a three-car split garage inside a gated waterfront community on Johns Lake. This 2020-built home in Lakeview Preserve is built around space and flexibility. The kitchen anchors the main living area with stainless appliances, a large center island, and an open sightline into the family room and dining space. A downstairs primary suite sits privately off the family room with a spacious walk-in closet and an oversized ensuite bath. On the opposite end of the first floor, a guest bedroom with its own private ensuite makes the layout ideal for multigenerational living or overnight guests. The true split floor plan keeps everyone's space their own. Upstairs holds three more bedrooms, including a second primary with a walk-in closet and private ensuite bath. The remaining two bedrooms share a guest bathroom. Lakeview Preserve is a gated community on Johns Lake with a resort-style pool, fitness center, cabana, playground, splash pad, and a private community dock with a kayak launch. Conservation areas run throughout the neighborhood. You're minutes from Hamlin Town Center, the 429, AdventHealth Horizon West, and Stoneybrook West Village, with Historic Downtown Winter Garden and the West Orange Trail about eight miles away. Disney is a fifteen-minute drive. Rare to find this much square footage, this many ensuites, and gated lake access all in one address.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Brad Young (407-897-5400)
68 N PARK AVE, WINTER GARDEN, FL 34787
$1,899,0001 Day on yellowkey MLS ID: O6400066
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3555 Built: 2021Monthly Fee: $325 Tax: $15,594 (2025)Community: 30 North ParkTownhouse
Taxes:$15,594
Elementary School: None
High School: None
Middle School: None
Remarks: Experience the ultimate in luxury urban living at 68 N Park Ave, a stunning 3-story townhome with rooftop deck located in the heart of Historic Downtown Winter Garden. This sophisticated 4-bedroom, 4.5-bathroom residence offers over 3,500 sq. ft. of meticulously designed space, seamlessly blending modern elegance with the charm of the historic district. The open-concept main level features soaring 11-foot ceilings, expansive industrial-style windows, and a chef’s dream kitchen equipped with an oversized quartz island, natural gas appliances, and custom artisan cabinetry. Accessibility is effortless with your own private elevator serving all floors. Retreat to the third-floor master suite, featuring a spa-inspired bath and massive walk-in closet, or host guests in the versatile first-floor bedroom suite. The "wow factor" continues on the 1,200 sq. ft. private rooftop terrace, offering panoramic views of the city skyline—the perfect spot for evening cocktails or watching local fireworks.Location is everything. Leave your car in the 2-car garage and embrace the golf-cart-friendly lifestyle. You are just steps away from: The award-winning Winter Garden Farmers Market, The vibrant Plant Street Market and Crooked Can Brewing Co, The world-class West Orange Trail for biking and running, Boutique shopping, fine dining, and the historic Garden Theatre. Don’t miss this rare opportunity to own a piece of downtown luxury. Schedule your private showing today!
Listing is courtesy of: VISTA CAY REALTY COMPANY (407-996-4656)
Listing Agent: Drew Frahm (407-996-4656)
15555 PANTHER LAKE DR, WINTER GARDEN, FL 34787
$2,000,0001 Day on yellowkey MLS ID: O6400010
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4342 Built: 2016Monthly Fee: $431 Tax: $28,576 (2025)Community: Lakeshore Preserve Ph 1Single Family
Taxes:$28,576
Remarks: Welcome to luxury living in the highly sought-after Panther Lake community in Winter Garden. This award-winning Toll Brothers Maranello model home is now available for sale —offering over 4,600 square feet of impeccably designed living space, featuring 5 bedrooms and 5+ bathrooms, all set on a premium waterfront lot. From the moment you arrive, the home makes a statement with its elegant architecture and professionally designed finishes throughout. The grand foyer opens seamlessly into an expansive great room, where natural light, volume ceilings, and refined details create a space that is both inviting and impressive. At the heart of the home is a chef-inspired kitchen, complete with a large center island, premium cabinetry, and a walk-in pantry, all overlooking a bright breakfast area. From here, step directly onto the expansive covered lanai, where indoor and outdoor living come together effortlessly. This is where the home truly sets itself apart. Enjoy your own private resort-style outdoor retreat, featuring a stunning infinity-edge pool overlooking the lake, a fully equipped outdoor kitchen, and a gas fireplace—creating the perfect setting for entertaining or relaxing in total privacy. The primary suite, located on the first floor, offers a luxurious escape with a spa-like bathroom, dual vanities, a walk-in shower, and a generous walk-in closet. Also on the main level, you’ll find a private en-suite guest bedroom as well as a separate mother-in-law suite, providing flexibility for guests or multi-generational living. Upstairs, the home continues to impress with a spacious loft featuring a built-in bar, three additional bedrooms with bathrooms, and a beautiful balcony that adds both charm and additional outdoor living space. Located in one of Winter Garden’s most desirable communities, this home offers privacy, prestige, and convenience, with close proximity to top-rated schools, shopping, dining, and major roadways. Model homes of this caliber—especially with a waterfront lot and infinity pool—rarely become available. Schedule your private showing today and experience elevated living at its finest.
Listing is courtesy of: RIGHTHOUSE REALTY LLC (407-216-8788)
Listing Agent: Tim Schmidt (407-216-8788)
15306 GILLIGAN CT, WINTER GARDEN, FL 34787
$925,0001 Day 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
High School: Horizon High School
Middle School: Water Spring Middle
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)
328 BAYSIDE AVE, WINTER GARDEN, FL 34787
$445,0001 Day 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
High School: West Orange High
Middle School: Lakeview Middle
Remarks: 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)
13158 BOUNTY AVE, WINTER GARDEN, FL 34787
$395,000253 Days on yellowkey MLS ID: O6334532
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1567 Built: 2022Monthly Fee: $257 Tax: $6,198 (2024)Community: WaterleighSpa: NoTownhouse
Taxes:$6,198
Tax Year: 2024
Remarks: Welcome home to The Ibis Model at Waterleigh! This beautiful, spacious town home with 3 bedrooms, 2.5 baths Has all the space of a single family home, but with a carefree living. The kitchen is equipped with stainless steel appliances, granite countertops and a large walk in pantry that is equipped with extra storage! This home invites you from the time you enter! This lifestyle Community includes over the top amenities with multiple beautiful clubhouses with 3 resort style pools, 2 fitness centers, putt-putt golf, beach volleyball, tennis, lake view BBQ/picnic area, dog-park and so much more. Did i mention that Lawn care is included! Built in 2022 this home is essentially new! Close to sought after schools, shopping and more! Make your appt to view the community that is a “must see” in Winter Garden/Horizons West
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Sascha Davis (304-395-9407)
17231 MELOGOLD WAY, WINTER GARDEN, FL 34787
$969,00080 Days on yellowkey MLS ID: O6377688
0 Days Off yellowkey (back on 4/17/2026)
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3787 Built: 2024Monthly Fee: $85 Tax: $2,836 (2024)Community: Northlake/Ovation Ph 1Single Family
Taxes:$2,836
Elementary School: Bay Lake Elementary
Remarks: Stunning Upgraded Two-Story Home in Prime Winter Garden Location Welcome to this exceptional two-story residence in the heart of Winter Garden, thoughtfully designed to impress even the most discerning buyers. Featuring 5 spacious bedrooms and 4.5 bathrooms, this home offers comfort, functionality, and style in every detail. The primary suite is a true retreat, complete with a generous walk-in closet, while the additional bedrooms feature built-in closets for smart, efficient storage. The open floor plan creates a seamless flow throughout the home, highlighted by expansive living and dining rooms that are perfect for entertaining or everyday living. The beautifully appointed kitchen stands out with solid wood cabinets, elegant stone countertops, and appliances—combining timeless design with modern convenience. This home boasts nearly $120,000 in builder upgrades, plus custom built-in furniture, delivering a level of quality and finish rarely found. Outside, you’ll appreciate the added privacy of a fenced yard and an expanded driveway—extended three feet on each side beyond the neighborhood standard—providing extra space and convenience. A 2-car attached garage completes the package. Located near a major road with easy access to shopping, dining, and entertainment, and zoned for highly regarded schools, this property offers both lifestyle and location. With a low HOA of only $85 per month, this is a rare opportunity to own a highly upgraded home in one of Winter Garden’s most desirable areas.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Joao Freitas De Souza Freitas, Jr (407-342-6363)
375 REGAL DOWNS CIR, WINTER GARDEN, FL 34787
$334,90052 Days on yellowkey MLS ID: O6377205
0 Days Off yellowkey (back on 3/20/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1464 Built: 2001 Tax: $4,413 (2024)Community: Regal Pointe Ph 01 43/129Single Family
Taxes:$4,413
Elementary School: Maxey Elem
Remarks: Under contract-accepting backup offers. Welcome to this beautiful 3-bedroom, 2-bathroom home with a two-car garage in the heart of the Regal Pointe subdivision of Winter Garden. Upon entry, you are welcomed by the large kitchen overlooking the living room, embracing open-concept living. The kitchen features laminate countertops, a tile backsplash, a breakfast eating area, and stainless steel Whirlpool appliances. The primary bedroom offers a private retreat, situated on the opposite side of the house from the secondary bedrooms. The large, open living room provides sliding door access to a screened-in patio with a peaceful pond view, making it the perfect place to enjoy a morning coffee or evening drink. You’re conveniently located within 25 minutes of Orlando’s theme parks, the airport, and downtown Orlando. Schedule your showings today!
Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)
Listing Agent: Robert Salmons (888-216-6364)
1720 PORTCASTLE CIR, WINTER GARDEN, FL 34787
$389,90080 Days on yellowkey MLS ID: O6377195
2 Days Off yellowkey (back on 2/20/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1606 Built: 2004Monthly Fee: $46 Tax: $5,520 (2024)Community: Stone Creek Unit 4Spa: NoSingle Family
Taxes:$5,520
Elementary School: Whispering Oak Elem
Middle School: SunRidge Middle
Remarks: Under contract-accepting backup offers. Welcome to this fantastic, move-in ready, 4-bedroom, 2.5-bathroom, two-story home with a two-car garage. Enter the foyer leading directly into the open-concept living room and kitchen. The kitchen is functional and stylish, featuring laminate countertops, an island, and stainless steel appliances. Conveniently located off the kitchen are the laundry room, a half bathroom, and access to the two-car garage. All four bedrooms are located on the second level, with the primary suite situated at the rear of the home for privacy. A small flex space upstairs is perfect for a reading nook or a small office area. The primary bedroom features a walk-in closet and an attached ensuite with dual sinks and a tub/shower combo. Schedule your showings today!
7036 TWILIGHT BAY DR, WINTER GARDEN, FL 34787
$524,900166 Days on yellowkey MLS ID: S5137842
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 1914 Built: 2023Monthly Fee: $180 Tax: $750 (2023)Community: MezzanoTownhouse
Taxes:$750
Elementary School: Summerlake Elementary
Tax Year: 2023
Middle School: Horizon West Middle School
Remarks: Motivated Seller-Excellent investment opportunity in the exclusive Mezzano community of Winter Garden. This fantastic Stone House–style townhouse, built in 2023, is currently tenant-occupied through February 28, 2027, providing immediate rental income from day one. The residence features a modern 4-bedroom, 3.5-bathroom layout, including a primary suite on the first floor, a junior suite upstairs, and premium finishes throughout. Designed with an open-concept interior and abundant natural light, the property also includes a private patio and an EV charger. Strategically located just minutes from Hamlin Town Center, Flamingo Crossings, and top-rated A+ schools, it offers long-term value in one of Central Florida’s premier growth corridors. Residents enjoy access to a resort-style pool and playground. This is a turn-key asset for any portfolio seeking a high-quality property in a prime location.
Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)
Listing Agent: Carola Garcia De Montenegro (407-616-5098)
1672 MALCOLM POINTE DR, WINTER GARDEN, FL 34787
$519,900232 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
High School: Ocoee High
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)
3467 BUOY CIR, WINTER GARDEN, FL 34787
$629,000104 Days on yellowkey MLS ID: G5106141
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2610 Built: 2020Monthly Fee: $152 Tax: $5,995 (2025)Community: Lakeview PreserveSingle Family
Taxes:$5,995
Remarks: This move-in ready lakeview home offers 4 bedrooms, 3 full bathrooms, and a spacious bonus room that can easily serve as a 5th bedroom or versatile flex space. The main level features four bedrooms, two full bathrooms, and an open concept kitchen, dining and living area, along with an extended two-car garage. Designed for both comfort and functionality, this home includes tile throughout the main living areas, new carpet in all bedrooms, tray ceilings in the living room and primary suite, and quartz countertops in the kitchen and bathrooms. Upstairs, a generously sized bonus room with full-bathroom and two closets offers flexibility as a future in-law suite, home office, media or game room. Additional highlights include ample storage throughout and an interior laundry room with cabinetry and utility sink. Enjoy outdoor living from your covered front porch, fully fenced backyard, and screened-in patio overlooking John’s Lake. Located in Lakeview Preserve, this gated community offers a clubhouse, resort-style pool with zero-entry, playground, splash pad, fitness center, centralized mailboxes, and a community dock and kayak launch on John’s Lake, creating the perfect combination to enjoy Florida living.
Listing is courtesy of: CAM REALTY & PROPERTY MANAGEME (407-929-1852)
Listing Agent: Chelsea Eckert (407-455-2785)
16838 OLD HIGHWAY 50, WINTER GARDEN, FL 34787
$875,0003 Days on yellowkey MLS ID: O6399357
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1795 Built: 1972 Tax: $4,787 (2025)Community: Lake Highlands 23-22-26Mobile Home
Taxes:$4,787
Elementary School: Grassy Lake Elementary
High School: Lake Minneola High
Middle School: East Ridge Middle
Remarks: **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Rare opportunity to own 5 acres of highly versatile land near Orlando, Clermont, and Winter Garden, located at 16838 Old Highway 50 in a rapidly growing corridor of Lake County. This property offers 300 feet of frontage and is already divided into three parcels, with agricultural, commercial, and residential zoning, making it ideal for developers, builders, investors, or anyone searching for land for sale in Orlando, Clermont development land, Winter Garden acreage, or Central Florida investment property. Positioned in a high-growth area with ongoing expansion and development, this property is a prime candidate for residential development, mixed-use, or future commercial use. Currently on the property are two manufactured homes, including a fully remodeled home updated within the last two years with a new kitchen, new flooring, and extensive renovations completed down to the studs—perfect for immediate occupancy, rental income, or use as part of a private family compound. The second is a 4-bedroom, 2-bath manufactured home that has already been improved and is currently used for storage, but can easily be converted into an in-law suite, guest home, or additional living space. The property also features a city-converted self-watering system (contact listing agent for full details). With ample space for animals, horses, barns, horse stables, workshops, and agricultural use, this property offers endless possibilities for equestrian living, farming, development, or multi-generational living. Flexible zoning, prime frontage, proximity to major growth areas, and rare acreage make this a standout opportunity for anyone looking for land for sale in Orlando, Clermont land, Winter Garden development land, or Central Florida acreage with future upside. Opportunities like this are rare in such a high-growth location.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
671 CANOPY ESTATES DR, WINTER GARDEN, FL 34787
$1,325,00040 Days on yellowkey MLS ID: O6383438
REDUCED by $25,000 (1.9%) on 04/08/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4490 Built: 2019Monthly Fee: $300 Tax: $12,519 (2024)Community: Canopy Oaks Ph 1Spa: YesSingle Family
Taxes:$12,519
Elementary School: Lake Whitney Elem
Remarks: Under contract-accepting backup offers. Canopy Oaks, located in Winter Garden, Florida, is a unique blend of high-end luxury homes and suburban tranquillity. This gated enclave, developed by the distinguished home builder A.R. Bailey, features 49 classic estates. The meticulously crafted community is designed to cater to the specific needs and desires of homeowners, and includes a scenic nature trail, a children’s play park, and a community post office. From the moment you arrive at this Mediterranean POOL estate home, it makes a BOLD statement with its 8-foot Solid Wood Arched double entry doors. You are greeted with cathedral ceilings, solid wood oversized French doors to the private office, elegant hand forged custom iron railings, and a unique wine cellar with a custom hand forged iron gate. Luxury details and fine craftsmanship are inside this 5 BR/4.5 Ba/2-car garage POOL home. Open Floor plan leads pleasantly into the chef-style kitchen with the perfect layout for entertaining. The kitchen includes Bespoke Samsung stainless steel appliances, including a Family Hub Refrigerator. Gas stove top, built-in oven, and built-in convection oven. Granite counters. Completing the 1st floor, in addition to the 1st MBR, is a den/office, laundry room, generous dining area, powder bath, epoxy-coated garage floor 2-car garage, Autel Level 2 EV Charger and large lanai complete with Remote controntrolled, motorized retractable patio screens (upstairs and downstairs). The lanai and pool area are designed as additional living space, with pre-plumbing and Gas for your Summer Kitchen. Tons of architectural features throughout, upgraded light fixtures. Both Primary Suites have built in Kitchenettes. The media room includes a mini kitchenette with sink and microwave, and the theatre is wired for a 5.1 in-wall sound system. Three en-suite bedrooms and a Second Master Suite can also be found on this upper floor – perfect for multi-generational options and living privacy. The upstairs primary bathroom and closet are a dream come true. The Spa style bath has granite countertops, custom wood cabinetry, spacious dual sinks, an elegant free-standing soaking tub, seperate frameless glass wall shower with a bench. The custom-made, upgraded, solid wood oversized closet is Couture-Ready. Rainsoft whole-home water filtration/treatment/softener system. Luxury saltwater pool and spa. Privacy hedges along the side yard. Pool lighting; spa with custom tile; finished pool surface; low-maintenance turf and landscaping in the backyard. Exterior lighting, LED trim lighting. The list goes on and on. This home is a must see. An exceptional estate at an exceptional value, Canopy Oaks is located on Roper Road between Winter Garden’s downtown historic district and the Winter Garden Village shopping complex. With convenient access to major highways such as 429, 408, and the Turnpike, and its proximity to world-renowned attractions like Disney World® and Universal Studios®, this home offers an exceptional opportunity for easy commuting.
Listing Agent: Sean Flatley (609-208-8204)
628 ORANGE BELT LOOP, WINTER GARDEN, FL 34787
$525,00038 Days on yellowkey MLS ID: O6389653
0 Days Off yellowkey (back on 4/11/2026)
REDUCED by $4,900 (0.9%) on 04/04/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1850 Built: 2018Monthly Fee: $336 Tax: $3,620 (2025)Community: Heritage At Plant Street Community AssocSpa: NoTownhouse
Taxes:$3,620
Remarks: Under contract-accepting backup offers. Live the downtown Winter Garden lifestyle in this beautifully upgraded CORNER UNIT townhome in the sought-after community of Heritage at Plant Street—perfectly located in the GOLF CART DISTRICT with direct access to the renowned WEST ORANGE TRAIL. Built in 2018 by M/I Homes and meticulously maintained by its original owners, this 2-story, 3 bedroom, 2.5 bath townhome with a 2-car garage offers the ideal combination of low-maintenance living, thoughtful upgrades, and a prime corner location. With HOA-covered exterior maintenance—including the roof and grounds—you’ll spend less time on upkeep and more time enjoying everything downtown living has to offer. The coveted corner placement provides extra privacy, abundant natural light, and a common area GRASSY SIDE YARD perfect for pets or play, while a large guest parking lot sits conveniently just steps from the front door. Inside, the Windham II floor plan features soaring ceilings and a bright, open layout. A light-filled den off the foyer with three large windows offers flexibility as a home office, playroom, or second living space. The heart of the home is the DESIGNER KITCHEN, showcasing slate GE Profile appliances, a NATURAL GAS COOKTOP AND CUSTOM RANGE HOOD, stacked convection wall oven and microwave, and 42" dark shaker cabinetry with hardware. SILESTONE countertops, tiled backsplash, under-cabinet LED lighting, and stylish pendant lights complete the space. The large island with breakfast bar and included barstools opens seamlessly to the dining area and great room, creating the perfect setup for entertaining. Corner-unit placement provides windows on two sides of the great room and dining area, creating a bright, naturally lit living space. The entire first floor features durable large format ceramic tile flooring, while the staircase has been upgraded with dark engineered wood for a polished, low-maintenance look. A spacious laundry room with full-size washer and gas dryer, upper cabinets, and an oversized under-stair storage nook adds everyday convenience. Upstairs, the private primary suite offers a large walk-in closet and an elegant en-suite bath with raised-height dark shaker cabinetry, Silestone double vanity, and a tiled walk-in shower with seamless glass enclosure. Two additional bedrooms share a well-appointed bathroom with matching finishes and a tiled tub/shower combination. Step outside through the French door with built-in blinds to your private, screened brick-paver courtyard, offering both covered and open seating areas—perfect for relaxing or entertaining while overlooking the grassy side yard. The adjoining two car garage with alley access includes screened sliders for a cross breeze into the patio area. Energy-efficient features include ENERGY STAR double-pane Low-E windows, HVAC, insulation, and appliances. The ROOF, HVAC, and INSTANT HOT GAS WATER HEATER were installed in 2018 and have been regularly serviced. The home also features modern high end, noise free ceiling fans with remotes in all bedrooms and living areas, faux wood blinds throughout, and a NEUTRAL INTERIOR PALETTE ready for your personal style. Residents enjoy neighborhood amenities including a POOL and DOG PARK, all just minutes from the shops, dining, and vibrant atmosphere of historic downtown Winter Garden. Spring into the season of easy living—this rare corner-unit opportunity is your key to enjoy everything downtown Winter Garden is famous for.
Listing Agent: Kim Blaylock (407-497-9321)
14626 BLACK QUILL DR, WINTER GARDEN, FL 34787
$799,9002 Days on yellowkey MLS ID: O6399975
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2907 Built: 2016Monthly Fee: $215 Tax: $6,816 (2025)Community: Overlook At HamlinSpa: YesSingle Family
Taxes:$6,816
Elementary School: Independence Elementary
Middle School: Bridgewater Middle
Remarks: MINT CONDITION 4 bedroom pool home in Overlook at Hamlin! Original Owners have taken great care of this Taylor Morrison Jamestown model with EXTENDED PRIMARY SUITE AND EXTENDED LANAI! Natural Gas Community! GAS cooktop and GAS Tankless Hot Water Heater. Lots of crown moldings and picture frame moldings throughout. PLANTATION SHUTTERS as well. NEW AC SYSTEM 2025! The Outdoor space features a GAS HEATED SPOOL (Yes, combination Pool and Spa!) Travertine Decking and screened enclosure. The back yard is also fenced for privacy and pets. There is also a space for pets with synthetic turf, so no cutting grass in the backyard. Beyond the pool area is a dry retention area, so NO REAR NEIGHBORS! This property is expected to go quickly so don't delay in making your appointment!
Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)
Listing Agent: Thomas Moffett (407-375-6498)
213 W TILDEN ST, WINTER GARDEN, FL 34787
$765,00066 Days on yellowkey MLS ID: O6381848
0 Days Off yellowkey (back on 3/2/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2151 Built: 1972 Tax: $8,105 (2025)Community: Westlake Manor 1St AddSingle Family
Taxes:$8,105
Remarks: Located in DOWNTOWN WINTER GARDEN!! This beautifully renovated single story home combines charm with modern upgrades. Completely redesigned in 2021, this home showcases numerous upgrades, including new roof, new HVAC, recently installed Whole-House Water Filtration System, stunning new kitchen, new granite countertops, large center island with storage cabinets, built in walk-in pantry. Additional upgrades include double paned windows, new exterior/interior doors, fully renovated bathrooms, porcelain tile flooring throughout the home. Step outside into your own private oasis, you'll find a wood fenced beautiful backyard with lush landscape and patio area, ideal for relaxing and soaking up the Florida sunshine. Irrigation runs off a well. Set on a beautifully, tree-lined street shaded by majestic live oaks. This home invites you into a bright, open concept layout perfect for both relaxing and entertaining. The spacious living room flows seamlessly into the dining area and kitchen with a large center island, creating a central gathering space for family and friends. Spacious 2 car garage with EV charger outlet and custom garage door. Located in the heart of the Golf Cart District, you can walk or take your golf cart to Plant Street Market, local restaurants, charming boutiques, café spots, and the Farmers Market. Enjoy the small-town atmosphere, community events, festivals, walk or bike to West Orange Trail and enjoy the scenic beauty of nearby Lake Apopka—all with NO HOA!! This home is perfectly nestled in one of Central Florida’s most desirable and vibrant neighborhoods. This is a rare opportunity to own one of the area’s finest homes in a location that combines luxury, lifestyle and small town charm. Close to major highways, minutes to Disney, 30 mins from Orlando. Schedule your private tour today!! See why this incredible property is the best of Winter Garden living!!
Listing is courtesy of: UNITED REALTY GROUP INC (954-450-2000)
Listing Agent: Alice Acosta (561-356-6385)
12043 HOLYSTONE ST, WINTER GARDEN, FL 34787
$385,000223 Days on yellowkey MLS ID: O6339950
1 Days Off yellowkey (back on 4/17/2026)
REDUCED by $5,000 (1.3%) on 04/01/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1568 Built: 2023Monthly Fee: $259 Tax: $6,198 (2024)Community: Waterleigh Ph 4ATownhouse
Elementary School: Waterbridge Elem
Remarks: Under contract-accepting backup offers. Motivated Seller MOVE IN READY . Welcome to Waterleigh community! This townhome has 3 bedroom 2.5 bathroom is conveniently located in Waterleigh Phase 4, near the Elementary and Middle School! It offers a welcoming open concept as you immediately enter the foyer, with plenty of cabinet, double sink, granite countertops and a long kitchen island overlooking the dining space.The community offers great amenities such as pool, gym and a club house.
Listing Agent: Ruth Santos (407-808-4766)
2202 ROMANUM DR, WINTER GARDEN, FL 34787
$585,0002 Days on yellowkey MLS ID: O6398743
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1889 Built: 2015Monthly Fee: $211 Tax: $3,839 (2025)Community: Alexander RidgeSingle Family
Taxes:$3,839
Remarks: Welcome to your next home in the heart of Winter Garden—where location, lifestyle, and upgrades come together seamlessly. This beautifully updated 3-bedroom, 2-bathroom home is perfectly positioned just 20 minutes from Disney, 15 minutes from Downtown Winter Garden, and only 10 minutes to Winter Garden Village, giving you easy access to everything Central Florida has to offer. Step inside to find brand-new luxury vinyl flooring, fresh exterior paint (2024), and a bright, open feel that makes the home both inviting and functional. The enclosed Florida room adds an additional 135 square feet of living space, complete with elegant French doors—perfect for a home office, flex space, or relaxing retreat. Out back, enjoy your own private putting green—ideal for unwinding or entertaining guests. And with HOA-maintained landscaping, you can say goodbye to yard work and hello to low-maintenance living. Major updates bring peace of mind, including a new roof (2024), new AC unit (2025), and new gutters (2024). Additional features include a garage with epoxy flooring, a hybrid hot water heater, and a sleek GE Slate appliance package that adds a modern touch to the kitchen. This home checks all the boxes—location, upgrades, and lifestyle. Schedule your private showing today and experience it for yourself.
Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)
Listing Agent: Trevor Zwick (863-303-6114)
15543 PEBBLE RIDGE ST, WINTER GARDEN, FL 34787
$645,900547 Days on yellowkey MLS ID: O6250356
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
Remarks: 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)
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