Location: Winter Garden
Do Not Show Listings
9225 HOLLISTON CREEK PL, WINTER GARDEN, FL 34787
$1,150,0006 Days on yellowkey MLS ID: O6427589
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3897 Built: 2017Monthly Fee: $158 Tax: $15,124 (2025)Community: Watermark Ph 1BSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$15,124
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Welcome to 9225 Holliston Creek Place, an exceptional pool home nestled on a premium corner lot in one of Winter Garden's most sought-after communities. From the moment you arrive, the lush landscaping, side-entry garage, and beautifully maintained exterior set the tone for everything this home has to offer. Step inside and you are immediately greeted by soaring ceilings, an abundance of natural light, and a thoughtfully designed open floor plan that flows seamlessly from the formal living and dining areas into the heart of the home. The spacious kitchen is a true entertainer's dream, featuring generous counter space, ample cabinetry, and a layout that opens directly to the main living area — perfect for gatherings of any size. The dedicated home office is one of the standout features of this property — large, well-appointed, and completely separate from the living spaces, giving you the ideal work-from-home setup or the flexibility to use as a fifth bedroom, playroom, or media room. The primary suite is a private retreat, offering a generous layout, spa-like en suite bathroom with dual vanities, soaking tub, and walk-in shower. Secondary bedrooms are well-sized and thoughtfully positioned for privacy. Step outside and discover your own backyard oasis. The screened pool and lanai area is designed for true Florida living — whether you are taking a morning swim, hosting a weekend cookout, or simply unwinding at the end of the day. The summer kitchen is fully equipped and perfectly positioned to make outdoor entertaining effortless, with everything you need just steps from the pool deck. Being on a corner lot provides additional yard space, extra privacy, and enhanced curb appeal that interior lots simply cannot match. Located in a vibrant, well-established Winter Garden community with easy access to top-rated schools, SR-429, the 408, shopping, dining, and all of Central Florida's best attractions — this one truly checks every box.
Listing is courtesy of: GLOBAL FLORIDA REALTY (407-380-3030)
Listing Agent: Michael Bouchard (407-443-1284)
7467 JOHN HANCOCK DR, WINTER GARDEN, FL 34787
$1,350,00027 Days on yellowkey MLS ID: O6421848
1 Days Off yellowkey (back on 7/15/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3964 Built: 2019Monthly Fee: $215 Tax: $16,560 (2025)Community: West Lake Hancock EstatesSpa: YesSingle Family
Taxes:$16,560
Elementary School: Independence Elementary
High School: Horizon High School
Middle School: Hamlin Middle
Remarks: Luxury, comfort, and an unbeatable location come together in this exceptional home in the highly sought-after Horizon West community. Perfectly positioned just minutes from Disney, shopping, dining, major highways, and top-rated schools, this move-in-ready residence offers the ideal combination of elegance, functionality, and the Florida lifestyle you’ve been looking for. Designed for both everyday living and entertaining, the home features 4 spacious bedrooms, 3 full bathrooms, a half bath, a dedicated office, a versatile bonus room, and a 3-car garage. The open-concept kitchen showcases a large center island, stainless steel appliances, and seamlessly connects to the spacious living areas. What truly sets this home apart is its stunning outdoor oasis. Since its original purchase, the owners have transformed the backyard into a private resort featuring a beautiful custom pool, an expansive covered lanai, and a fully equipped summer kitchen, creating the perfect setting for weekend barbecues, family gatherings, or simply relaxing while enjoying the peaceful pond views. Thoughtfully upgraded and impeccably maintained, this home is truly turnkey, allowing its next owners to move in and immediately enjoy one of Central Florida’s most desirable lifestyles. Whether you’re looking for your primary residence or a place where family and friends can create unforgettable memories, this property delivers the perfect blend of luxury, comfort, convenience, and quality of life.
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Diogo Mac Knight (407-364-7522)
15456 GILLIGAN CT, WINTER GARDEN, FL 34787
$550,000363 Days on yellowkey MLS ID: A4660262
0 Days Off yellowkey (back on 7/2/2026)
REDUCED by $25,000 (4.3%) on 06/12/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2571 Built: 2020Monthly Fee: $102 Tax: $8,702 (2024)Community: Winding Bay Ph 1BSingle Family
Taxes:$8,702
Tax Year: 2024
Remarks: Disney fireworks views, single-story living, low HOA — just 3.9 miles from Disney. Welcome to Winding Bay in Winter Garden, where location, lifestyle, and long-term value come together in one beautifully maintained home. This pristine 3-bedroom, 3.5-bath residence with a flexible bonus room offers the perfect setup for everyday living, visiting guests, remote work, or a potential future sleeping space with proper modification and verification. From the moment you arrive, the home makes a statement with its brick-paved driveway, stone-accented façade, and inviting curb appeal. Inside, the bright open floor plan is designed for comfort and function, featuring a dedicated built-in desk area, an oversized mudroom, an adjacent laundry room, custom cabinetry, and generously sized guest suites. The heart of the home is the chef-inspired eat-in kitchen, complete with 42-inch soft-close cabinetry, quartz countertops, designer backsplash, vented range hood, built-in microwave, massive walk-in pantry, and an oversized island with seating for up to eight — ideal for entertaining, hosting family, or gathering after a day at the parks. The open dining and family room are filled with natural light and flow seamlessly to the custom-designed backyard, where you can relax and enjoy direct views of Disney fireworks from home — a rare and memorable feature that truly sets this property apart. Winding Bay offers a peaceful, pride-of-ownership atmosphere with no short-term rentals permitted, helping preserve the neighborhood feel while still keeping you minutes from Disney, dining, shopping, schools, and major conveniences. Residents also enjoy a community pool, dog park, and a low HOA of just $102/month. Move-in ready, meticulously maintained, and positioned in one of Winter Garden’s most desirable communities, this home is ideal for owner-occupants, Disney professionals, second-home buyers, or anyone seeking proximity to the magic without the noise, crowds, or rental turnover. Private showings available by appointment.
Listing is courtesy of: NEXTHOME CASA BELLA ELITE (813-726-5646)
Listing Agent: Loren Rosenthal (813-726-5646)
15009 LEBEAU LOOP, WINTER GARDEN, FL 34787
$775,0006 Days on yellowkey MLS ID: O6427810
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2116 Built: 2022Monthly Fee: $101 Tax: $8,170 (2025)Community: Winding Bay Ph 3Spa: NoSingle Family
Taxes:$8,170
Remarks: Beautifully upgraded home in the highly desirable Winding Bay community! 3-bedroom, 2.5-bath + office/flex room one-story single-family home over 2,100 square feet of comfortable living space with modern finishes and an open floor plan filled with natural light. The spacious kitchen is truly the heart of the home, featuring a large quartz island, built-in oven and microwave, gas cooktop, stainless steel appliances, plenty of cabinet space, and a walk-in pantry. Master Bedroom Suite offers a spa-like bathroom with dual vanities, a large walk-in shower, and a custom walk-in closet. The dedicated office with built-in cabinetry provides an ideal work-from-home space. The backyard offers your own private retreat with a heated saltwater pool, covered lanai, outdoor kitchen, pergola, and a fully fenced yard—perfect for relaxing, entertaining, or enjoying Florida's beautiful weather year-round. Additional features include solar panels, luxury laminate flooring throughout the main living areas, a custom wood panel for the TV, a spacious laundry room with built-in cabinets and utility sink, an irrigation system, and a two-car garage with storage racks and an EV charger. Winding Bay enjoy resort-style amenities including a community pool, playground, dog park, and scenic walking paths, all conveniently located near Disney, Horizon West, shopping, dining, and top-rated schools.
Listing is courtesy of: TOP HOUSING LLC (689-250-2717)
Listing Agent: Sofia Bastardo (407-860-2429)
1801 BURDOCK DR, WINTER GARDEN, FL 34787
$599,90034 Days on yellowkey MLS ID: O6419427
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2534 Built: 2008Monthly Fee: $90 Tax: $3,695 (2025)Community: Carriage Pointe A-I & LSingle Family
Taxes:$3,695
Remarks: Callaway Model built by Taylor Morrison Home: Welcome home to this beautifully maintained residence offering exceptional curb appeal and timeless Florida charm. From the moment you arrive, you'll appreciate the attractive paver driveway, manicured landscaping, lush lawn, and welcoming covered front porch accented by elegant columns and mature palm trees. The home's inviting exterior showcases a desirable split bedroom style appearance, a spacious two car garage, and a thoughtfully landscaped front yard that creates a warm first impression. Situated in a well kept community, this property offers the perfect blend of comfort, style, and functionality. Whether you're enjoying your morning coffee on the front porch or welcoming guests into this charming home, you'll appreciate the pride of ownership evident throughout. Conveniently located near shopping, dining, entertainment, major roadways, and all that Winter Garden has to offer. Don't miss this opportunity to own a move-in-ready home in one of Central Florida's most sought-after areas! Roof was replaced in March 2026, AC 2018, Water Heater is newer.
Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)
Listing Agent: Tracy Hampstead (407-803-3137)
15790 SWEET LIMETTA DR, WINTER GARDEN, FL 34787
$899,00021 Days on yellowkey MLS ID: O6421864
0 Days Off yellowkey (back on 7/23/2026)
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3636 Built: 2020Monthly Fee: $72 Tax: $11,362 (2025)Community: Highlands/Summerlake Grvs Ph 2Single Family
Taxes:$11,362
Remarks: PRICE TO SELL!!!! Beautifully maintained and highly desirable residence in a prime Orlando-area location. This home stands out for its exceptional condition, functional layout, and inviting atmosphere, making it an outstanding opportunity for both homeowners and investors alike. Step inside to a bright and open living space filled with natural light, offering a seamless flow that enhances everyday comfort and entertaining. The thoughtfully designed kitchen connects effortlessly to the main living area, creating a practical and welcoming centerpiece of the home. In addition to the spacious living areas, the home features a dedicated office, perfect for working from home or creating a quiet study space, as well as a separate TV/media room, offering the ideal setting for movie nights, gaming, or relaxing with family and friends. The primary suite provides a private retreat with generous closet space and a well-appointed bathroom. Additional bedrooms are well-proportioned and flexible, ideal for guests or personal use. The home also features convenient in-unit laundry and ample storage throughout, adding to its everyday functionality. Located in a well-kept community with excellent access to major highways, shopping centers, dining options, and local attractions, this property offers both lifestyle and convenience in one package. With strong rental and resale appeal, this is a rare opportunity you don't want to miss. Buyer to verify all information, including HOA rules, fees, and rental restrictions.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Jennifer Olmeda (407-547-9242)
14902 ARRENA RD, WINTER GARDEN, FL 34787
$628,000649 Days on yellowkey MLS ID: O6248982
REDUCED by $10,000 (1.6%) on 07/14/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3392 Built: 2001 Tax: $7,754 (2023)Community: Arrowhead LakesSpa: NoSingle Family
Taxes:$7,754
Elementary School: Water Spring Elementary
Tax Year: 2023
Middle School: Water Spring Middle
Remarks: Under contract-accepting backup offers. WATERFRONT--2 ACRES--NO HOA 7 Miles west of Disneys' main entrance...Winter Garden address with "A rated" schools listed on tax records. Close to many restaurants, shopping and other amenities. This is considered the 4 Corner Area because across Hwy 192 is Kissimmee, Hwy 27 is just a couple blocks west and if you go North it is Clermont and going south on Hwy 27 is Davenport. Piece of Paradise..Spacious..Upgraded...MOVE IN READY.. Expansive 2 car garage..workshop...storage...oversized.. Also approx 19X11 shed with an upper loft area ..The property is partially fenced. --..French doors open to a deck overlooks Lake Chapin in the rear of the property with fruit trees, banana trees, ..No damage from hurricane Milton. You will absolutely need to see to appreciate this home...even driving by, it is deceivingly large from just outside appearance.(almost 3400 Living sq ft). Beautifully maintained and Quality throughout.--Double Paned, tilt-out Windows with Marble sills--Well Maintained Bamboo Flooring (quality thicker boards ).Loads of Storage throughout and lighted closets...extra insulation in attic..Ceiling fans with wall controls and remotes..-French doors..-the list continues... A Central Kitchen that will delight the Chef --It has been thought out from past years of wants and needs and implemented. A WALL of Cabinetry..Corner Lazy susans upper and lower , pull out drawers ..under counter lights ..Convection oven and island cooktop with grill. Bar area opening into the Living room/ Dining room.. Split bedrooms plan and Master Suite has an extra room adjoining,which could be a exercise room, office, sitting room just to name a few. Large (approx 16x15) Suite has 3 solid core barn doors to close off the double walk in closet ROOMs and for the entrance door. Beautifully done Master Bath. (approx 13x9) Inside Laundry room with additional outlet for another refrigerator ..freezer. More than expansive (approx 16x13 sq ft) with a prestine pool table that can stay or go...your call.. This home makes a fantastic home for entertaining and/or family life with room to grow .. Come and see this home and you will want to make it yours..There is not another like it around. and it's so rare to find
Listing is courtesy of: STAR SOLUTION PROPERTIES LLC (407-383-9317)
Listing Agent: Cheryl Danboise (407-383-9317)
9953 SUMMERLAKE GROVES ST, WINTER GARDEN, FL 34787
$859,99010 Days on yellowkey MLS ID: S5154027
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2935 Built: 2020Monthly Fee: $164 Tax: $10,398 (2025)Community: Watermark Ph 4ASingle Family
Taxes:$10,398
Elementary School: Panther Lake Elementary
Remarks: Welcome to this exceptional corner-lot home with a premium lot in the highly sought-after Watermark community of Horizon West, Winter Garden! This beautifully maintained residence offers 4 bedrooms, 3.5 bathrooms, plus a spacious bonus room that can easily serve as a 5th bedroom, home office, media room, or playroom. Designed for both comfort and entertaining, the open-concept floor plan is filled with abundant natural light and features a stunning gourmet kitchen with an oversized island, perfect for gathering with family and friends. The spacious living and dining areas flow seamlessly to the covered lanai, creating the ideal indoor-outdoor Florida lifestyle. The luxurious primary suite offers a private screened balcony, providing the perfect place to enjoy your morning coffee or unwind after a long day. Step outside to a generously sized, fully fenced backyard offering exceptional privacy and endless possibilities to design your dream outdoor oasis, whether you envision a custom pool, summer kitchen, or beautiful garden. Additional upgrades include a whole-home water softener system, epoxy flooring in the oversized two-car garage, and numerous thoughtful features throughout the home. Located within walking distance to top-rated schools and just minutes from shopping, dining, entertainment, major highways, Disney theme parks and everything Horizon West and Winter Garden have to offer, Watermark also features outstanding resort-style amenities for residents to enjoy year-round. This is more than just a home—it’s a lifestyle. Schedule your private showing today and experience everything this remarkable property has to offer.
Listing is courtesy of: MARCILLO REAL ESTATE LLC (954-297-3636)
Listing Agent: Maria Barrios Tovar (407-600-4040)
925 BAINBRIDGE LOOP, WINTER GARDEN, FL 34787
$815,00096 Days on yellowkey MLS ID: O6402075
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3580 Built: 2008Monthly Fee: $72 Tax: $4,880 (2025)Community: Covington ParkSpa: NoSingle Family
Taxes:$4,880
Elementary School: Dillard Street Elem
High School: Ocoee High
Middle School: Lakeview Middle
Remarks: Virtually Staged. Welcome to Covington Chase, one of Winter Garden's most sought after communities, where this beautiful home now features a brand new AC system that was just installed, giving you one less major expense to worry about. Just minutes from the charm and energy of Historic Downtown Winter Garden, this exceptional 4 bedroom, 4 full bathroom home sits on an oversized 0.38 acre lot and offers the perfect blend of space, comfort, and flexibility. The expansive backyard provides endless possibilities for entertaining, gardening, relaxing, or creating your own outdoor oasis. With nearly four tenths of an acre, there is plenty of room to enjoy the outdoors and make the space your own. A long driveway and spacious 3 car garage offer ample parking, extra storage, and even room for a golf cart so you can fully enjoy life in Winter Garden's popular golf cart district. Designed with everyday living in mind, the thoughtfully planned layout offers flexibility for a variety of lifestyles. The first floor features a spacious primary suite tucked away for privacy, complete with two walk in closets and a generously sized bathroom. A dedicated office provides the perfect space for working from home, hobbies, or a quiet retreat. You'll also find a convenient Jack and Jill bedroom and bathroom setup on the main level, adding even more versatility to the home's layout. Upstairs, a large loft offers the ideal space for movie nights, a game room, fitness area, or additional living space. A private bedroom and full bathroom complete the second floor, creating a comfortable retreat with added privacy. Recent updates add even more value, including the brand new AC system and a roof that was replaced just a few years ago, offering peace of mind for years to come. The location is just as impressive as the home itself. Only minutes away is the Historic Downtown Winter Garden District, where you'll enjoy locally owned restaurants, coffee shops, boutiques, live events, and the award winning weekly farmers market. Spend weekends exploring the nearby 22 mile West Orange Trail, perfect for biking, walking, or simply enjoying Florida's beautiful weather. Living in the golf cart district makes it easy to head downtown for dinner, festivals, or an evening out without needing to drive. Opportunities like this are rare. An oversized lot, versatile floor plan, downstairs primary suite, dedicated office, multiple living spaces, private upstairs retreat, 3 car garage, brand new AC system, and an unbeatable location near downtown Winter Garden make this home an exceptional opportunity to enjoy the best of Central Florida living.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erica Diaz (407-897-5400)
9567 MEADOW HUNT WAY, WINTER GARDEN, FL 34787
$945,00024 Days on yellowkey MLS ID: O6422408
REDUCED by $20,000 (2.1%) on 07/23/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4305 Built: 2019Monthly Fee: $164 Tax: $9,084 (2025)Community: WatermarkSingle Family
Taxes:$9,084
Remarks: Currently occupied by tenant. Tenant will move out Jan 2027. Welcome to this beautifully upgraded 5-bedroom, 5-bathroom floorplan, where comfort meets style in the highly sought-after Watermark community. One of the bedrooms has been thoughtfully converted into a spacious media room by the original owners in 2019, but it can easily function as a fifth bedroom if needed. From the charming front porch to the shining luxury tile floors, this home is filled with elegant touches throughout. As you step inside, you’re greeted by a custom full-length glass wall in the hallway, adding depth and openness to the floorplan. The first room on the left is a fully equipped office. Adjacent is a sophisticated formal dining room with stylish wallpaper. The soaring ceilings and oversized family room are designed for both entertaining and everyday comfort, featuring stunning window treatments, a high-resolution projector, and a built-in surround sound system—perfect for cinematic nights at home. The gourmet kitchen is a chef’s dream, featuring stainless steel appliances, a large quartz countertop, a summer kitchen layout, and designer pendant lights, all of which can remain with the home. The first-floor master suite is a true retreat with blackout window treatments, a spa-like bath with a soaking tub, and a generous walk-in closet. Upstairs, you’ll find three additional bedrooms, a spacious loft, a study/den, and a one-of-a-kind themed game room with a hand-painted moon mural, cloud accents, twinkling ceiling lights, and a second surround sound system. Step outside to a covered patio with a heat-block screen and ambient ceiling lighting—ideal for evening gatherings. Located just a short walk from the luxury clubhouse and nearby commercial plaza, you’ll enjoy resort-style amenities including pool, a fitness center, fire pit, waterslides, tennis and basketball courts—all with a low HOA. This home offers the perfect combination of luxury, convenience, and community living. There are four lights have been removed compared to the original listing photos: • The fixture in the front study room • The one in the formal dining room • The light above the staircase• The one in the morning/breakfast area Please call for showing.
Listing is courtesy of: INTEREALTY SERVICE (626-328-8535)
Listing Agent: Emma Yue (626-328-8535)
931 KYLEE ALY, WINTER GARDEN, FL 34787
$766,00085 Days on yellowkey MLS ID: O6404673
0 Days Off yellowkey (back on 6/20/2026)
REDUCED by $1,000 (0.1%) on 06/16/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2831 Built: 2022Monthly Fee: $393 Tax: $9,637 (2025)Community: Oakland ParkSingle Family
Taxes:$9,637
Elementary School: Tildenville Elem
High School: West Orange High
Remarks: Under contract-accepting backup offers. ***Seller to offer up to $17,000 toward buyer's closing cost & or rate buy down.*** There is a distinct rhythm to life in Oakland Park that cannot be replicated anywhere else in Central Florida. It is a refined balance of Old Florida charm and modern luxury, where tree-lined streets, curated green spaces, and intentional design create a true sense of place. As you enter the community, everything feels elevated and thoughtfully composed, with the 22-mile West Orange Trail serving as the heartbeat that connects residents to both nature and one another. At 931 Kylee Alley, this lifestyle is fully realized. Positioned on a prominent corner lot, this David Weekley Stoneybrook residence showcases timeless architecture with a clean, sophisticated presence. One of the greatest luxuries here is the ease of ownership. The homeowners' association provides full landscaping maintenance, allowing the property to remain in pristine condition without demanding your time. Your weekends are yours to enjoy, not manage. Inside, the home immediately impresses with intentional sightlines and natural light. Built in 2022, the design feels both current and enduring. Soaring ceilings and expansive windows, complemented by custom plantation shutters, create a bright yet grounded atmosphere. The gourmet kitchen anchors the home, featuring an oversized island with sleek, solid surface countertops that serve as the perfect setting for gathering, entertaining, or everyday living. The floor plan is designed for both connection and privacy. The main level offers a flexible and refined space that can function as a guest suite or executive-style home office. Upstairs, the private quarters provide a peaceful retreat. The primary suite is expansive and serene, complete with a spa-inspired bath designed for relaxation at the end of the day. Living here means immediate access to the West Orange Trail and the best of Winter Garden. Bike to Plant Street, enjoy the Saturday Farmers Market, or simply take in the charm of one of Central Florida’s most sought-after destinations. Within Oakland Park, residents enjoy resort-style amenities, including multiple pools, a clubhouse, and a dog park, all contributing to a true lock-and-leave lifestyle. From an investment perspective, this property stands out. It offers an exceptional price per square foot for Oakland Park, with pricing thoughtfully adjusted to reflect the opportunity for upstairs flooring customization. In a community where demand continues to outpace supply, especially for newer construction on premium corner lots, this home represents both immediate value and long-term upside. 931 Kylee Alley is more than a home. It is a strategic acquisition within one of Winter Garden’s most desirable communities.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Matthew Mckee (407-948-0658)
10750 PETRILLO WAY, WINTER GARDEN, FL 34787
$749,00021 Days on yellowkey MLS ID: O6423067
REDUCED by $1,000 (0.1%) on 07/21/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2613 Built: 2020Monthly Fee: $101 Tax: $5,059 (2026)Community: Winding Bay Phase 1BSingle Family
Taxes:$5,059
Tax Year: 2026
Remarks: Welcome to this beautifully upgraded 2020-built home in Horizon West offering 3 spacious bedrooms, 2.5 bathrooms, and a thoughtfully designed floor plan that blends style, comfort, and functionality. From the elegant formal living room to the expansive great room that seamlessly connects the kitchen, dining, and family areas, this home is perfect for both everyday living and entertaining.The heart of the home is the stunning chef's kitchen, featuring an oversized island, custom range hood, upgraded cabinetry with crown molding, and abundant workspace for cooking and gathering. Luxury tile flooring, upgraded in 2025, flows throughout the entire home, while crown molding, oversized baseboards, and decorative hallway columns add timeless architectural detail throughout the home.The spacious owner's suite offers a beautifully renovated spa-inspired bathroom, fully upgraded in 2026, creating a private retreat you'll love. A convenient Jack-and-Jill bathroom serves the secondary bedrooms, providing both functionality and privacy for family or guests.Outside, enjoy the screened lanai complete with sun shades, overlooking a fully fenced backyard with elegant iron fencing. Additional exterior features include an extended driveway, whole-home security camera system, and solar panels installed in 2022 for enhanced energy efficiency.Additional upgrades include a whole-home water softener system with reverse osmosis filtration in the kitchen, a dedicated garage outlet for an additional refrigerator or freezer, and numerous custom finishes that make this home truly move-in ready.With modern upgrades, exceptional attention to detail, and an ideal layout, this home offers the perfect combination of luxury, efficiency, and everyday comfort. Don't miss the opportunity to make this exceptional property your next home!
Listing is courtesy of: SUNSHINE LIFE REALTY LLC (321-229-0627)
Listing Agent: Michelle Fiorino-Ragni (352-223-9938)
1950 PANTHEON DR, WINTER GARDEN, FL 34787
$495,00037 Days on yellowkey MLS ID: O6418888
1 Days Off yellowkey (back on 7/22/2026)
REDUCED by $15,000 (2.9%) on 07/08/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1754 Built: 2015Monthly Fee: $211 Tax: $3,783 (2025)Community: Alexander RdgSingle Family
Taxes:$3,783
Elementary School: Hamlin Elementary
Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to 1950 Pantheon Drive, a charming 3-bedroom, 2-bath home located in the desirable Alexander Ridge community of Winter Garden. Offering 1,769 square feet of living space, this thoughtfully designed split-bedroom floor plan provides comfort, privacy, and easy everyday living. From the moment you arrive, the home makes a welcoming first impression with a bright exterior, paver driveway, covered entryway, mature landscaping, and a large front tree that adds shade and curb appeal. Inside, the open living, kitchen, and dining areas create a functional flow for relaxing, gathering, and entertaining. The living room features warm engineered wood flooring, neutral tones, and natural light from multiple windows, creating a bright and inviting main living space. The kitchen overlooks the living area and features granite countertops, warm wood cabinetry, stainless steel appliances, pendant lighting, recessed lighting, a breakfast bar, a center island, a deep kitchen sink, and a modern pull-down faucet. Just beyond the kitchen, the dining area provides a dedicated space for meals while remaining connected to the heart of the home. The private primary suite offers neutral tones and direct access to the ensuite bathroom. The primary bath features dual sinks, granite countertops, warm wood cabinetry, upgraded lighting, a walk-in shower with a glass enclosure, a separate soaking tub, and direct access to the walk-in closet. The walk-in closet also includes convenient door access to the laundry room, adding a smart everyday function. Bedrooms 2 and 3 are located on the opposite side of the home and share a spacious second bathroom. Recent updates include HVAC replaced in August 2024, PAID OFF Solar Panels in 2018, ROOF installed in 2023. The solar system is paid off, helping create an energy-efficient home with low-cost utilities. Alexander Ridge offers inviting community amenities, including a resort-style pool with paver decking, lounge areas, a covered pavilion, playground, open green space, and beautifully maintained common areas surrounded by mature landscaping and palm trees. This Winter Garden home blends comfort, function, efficiency, and community living in one inviting package.
Listing is courtesy of: EXP REALTY LLC (407-641-2808)
Listing Agent: Todd Schroth, Pa (407-641-2808)
342 WINDFORD CT, WINTER GARDEN, FL 34787
$319,90077 Days on yellowkey MLS ID: O6407632
REDUCED by $20,000 (5.9%) on 06/29/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1194 Built: 1996Monthly Fee: $40 Tax: $4,266 (2025)Community: Park Ave EstatesSingle Family
Taxes:$4,266
Remarks: *** $20k PRICE IMPROVEMENT*** Welcome to one of the best-priced opportunities in all of Winter Garden — a fully updated, move-in ready home where every major improvement has already been done for you. This is the kind of listing first-time buyers dream about: zero surprises, just keys and comfort. Step inside to find soaring vaulted ceilings and gleaming tile throughout, creating a bright, open feel the moment you walk through the door. The kitchen shines with granite countertops, stainless steel appliances, and a gas stove — a chef's delight and an entertainer's best friend. Both bathrooms have been tastefully refreshed with updated vanities and showers. And the best part? The washer and dryer stay. Out front, you'll fall for the adorable open porch — perfect for morning coffee or evening sunsets. Out back, a shed and additional exterior storage give you all the space you need for tools, hobbies, or weekend adventures. Another plus, the community pool is two doors down! Location is everything, and this home delivers. You're just minutes from the vibrant shops, restaurants, and farmers market of Downtown Winter Garden — without the premium price tag that usually comes with it.
Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)
Listing Agent: Brooke Cangro (407-758-6699)
9296 BOLERO RD, WINTER GARDEN, FL 34787
$779,00026 Days on yellowkey MLS ID: O6422122
REDUCED by $20,000 (2.5%) on 07/23/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2117 Built: 2020Monthly Fee: $193 Tax: $9,402 (2025)Community: Waterleigh Phs 3B 3C & 3DSingle Family
Taxes:$9,402
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: Welcome to this beautifully maintained 4-bedroom, 3-bath home built in 2020, ideally situated on a premium corner lot at the end of a quiet cul-de-sac in the highly desirable Waterleigh community. Offering an open-concept layout with luxury vinyl flooring, a spacious kitchen featuring a large island, modern finishes, and seamless living and dining areas, this home is perfect for everyday living and entertaining. Relax on the covered lanai while enjoying peaceful water views and breathtaking Florida sunsets. Residents enjoy resort-style amenities including multiple pools, fitness centers, tennis courts, playgrounds, walking trails, dog parks, BBQ and picnic areas, and lawn maintenance, all just minutes from top-rated schools, shopping, dining, hospitals, major highways, Flamingo Crossings, and Walt Disney World. This exceptional home offers the perfect combination of comfort, convenience, and resort-style living—schedule your private showing today!
Listing Agent: Any Alves (407-455-0618)
11277 HOLLOW BAY DR, WINTER GARDEN, FL 34787
$899,99034 Days on yellowkey MLS ID: O6419923
1 Days Off yellowkey (back on 7/23/2026)
REDUCED by $15,000 (1.6%) on 07/02/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3327 Built: 2025Monthly Fee: $208 Tax: $1,989 (2025)Community: WaterleighSpa: NoSingle Family
Taxes:$1,989
Remarks: Waterleigh presents the Seacliff. This two-story all concrete block construction single-family home features 4 bedrooms and 3.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you are greeted with a formal dining room. Customize this area to meet your needs with an optional den. Go down the hallway and you’ll find a powder room and laundry room tucked behind the stairwell leading up to the second floor. The well-appointed gourmet kitchen overlooks the casual dining area, family room and outdoor lanai. This home features a spacious kitchen island with built in sink and dishwasher to optimize counter space, and a walk-in pantry for extra storage. All homes in this community will have stainless steel appliances, making cooking a piece of cake. Bedroom one is located off the living space in the back of the home for privacy. The bedroom one bathroom impresses with separate vanities, shower/tub space, toilet room with privacy door as well as a spacious walk in closet. As we head upstairs, you are greeted with a loft area and all three bedrooms. Two bedrooms share a upstairs bathroom with double bowl vanity while the additional bedroom is complete with ensuite bathroom. Like all homes in Waterleigh, the Seacliff includes a Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)
Listing Agent: Stephen Cline (407-250-7299)
20 E DIVISION ST, WINTER GARDEN, FL 34787
$1,080,00054 Days on yellowkey MLS ID: O6413659
REDUCED by $40,000 (3.6%) on 07/23/2026
Bed: 4 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2729 Built: 1959 Tax: $7,197 (2025)Community: Winter Garden Shores First AddSpa: NoSingle Family
Taxes:$7,197
Remarks: Appraisal in hand! Welcome to one of Winter Garden's most remarkable custom transformations. This wasn't a flip—it was the owner's forever dream home. Originally built in 1959 and completely reimagined in 2023 and 2026. This extraordinary residence has undergone an extensive renovation and expansion, creating a truly one-of-a-kind property just minutes from Historic Downtown Winter Garden and Plant Street. Offering 2,729 square feet of beautifully designed living space, this 4-bedroom, 3-bathroom home showcases exceptional craftsmanship, thoughtful design, and luxury finishes throughout. In 2026, the owners completed a stunning expansion that includes an ultra-luxury primary suite designed as a private retreat. The spa-inspired custom bathroom features premium finishes, a private sauna, and a level of comfort rarely found at this price point. The heart of the home features open-concept living spaces filled with natural light, designer finishes, and seamless flow for everyday living and entertaining. Step outside to your private backyard oasis featuring a brand-new custom pool completed in 2026, creating the perfect setting for relaxing weekends and unforgettable gatherings. Major improvements include a 2026 HVAC system, 2026 luxury primary suite addition, 2026 custom pool, 2022 plumbing, 2022 electrical, 2018 roof, and all new windows installed in 2018, providing peace of mind for years to come. Every inch of this home tells the story of a family who spared no expense creating their dream home. Now, that dream can become yours. Schedule your private showing today!!!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Liz Boyce (407-784-4919)
16827 EVERMORE ALLEY, WINTER GARDEN, FL 34787
$525,0907 Days on yellowkey MLS ID: O6427521
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1628 Built: 2026Monthly Fee: $152Community: Silverleaf OaksSpa: NoSingle Family
Taxes:$0
Elementary School: Vista Lakes Elem
High School: Colonial High
Middle School: Odyssey Middle
Remarks: Under Construction. Discover Silverleaf Oaks in Winter Garden! This new home community will feature a collection of single-family and townhomes in desirable Horizon West. Located in the heart of Orlando’s attractions, residents will enjoy an array of amenities, including a resort-style pool, cabana, and playground – without a CDD. Plus, minutes to shopping, dining, and entertaining! Introducing the Benton bungalow, a brand-new home that includes 3 spacious bedrooms, 2 full bathrooms, a powder room, and a 2-car rear-load attached garage. The heart of the home is the open-concept kitchen, café, and gathering room, all bathed in natural light. This inviting space is perfect for both everyday living and entertaining. The kitchen boasts a large center island, a convenient storage pantry, and top-of-the-line Whirlpool stainless steel appliances—including a refrigerator. White cabinetry, decorative tile backsplash, and quartz countertops complete the sophisticated look. For added convenience, the first floor includes a powder room and coat closet. Upstairs, you’ll find the private owner’s suite, two additional bedrooms, a second full bathroom, and the laundry room. The owner’s suite is a true retreat, featuring a walk-in closet and a luxurious en suite bathroom with a frameless glass-enclosed shower, quartz-topped dual vanity, and linen closet. Throughout the first floor, enjoy the beauty of Wood-Look Luxury Vinyl Plank flooring, while tile enhances the laundry room and bathrooms. Plush, stain-resistant Shaw carpet covers the stairs and bedrooms, adding comfort and style. This new construction home perfectly blends luxury, convenience, and modern design, making it the ideal place to live and unwind.
Listing is courtesy of: PULTE REALTY OF NORTH FLORIDA LLC (407-250-9131)
Listing Agent: Adrienne Escott (407-250-9131)
16803 EVERMORE ALLEY, WINTER GARDEN, FL 34787
$537,2907 Days on yellowkey MLS ID: O6427359
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1896 Built: 2026Monthly Fee: $152 Tax: $1,372 (2025)Community: Silverleaf OaksSpa: NoSingle Family
Taxes:$1,372
Remarks: Discover Silverleaf Oaks in Winter Garden! This new home community will feature a collection of single-family and townhomes in desirable Horizon West. Located in the heart of Orlando’s attractions, residents will enjoy an array of amenities, including a resort-style pool, cabana, and playground – without a CDD. Plus, minutes to shopping, dining, and entertaining! Introducing the Haddock bungalow, a brand-new home that combines modern design and ultimate comfort, featuring 3 spacious bedrooms, 2 full bathrooms, a powder room, and a 2-car rear-load attached garage. The heart of the home is the open-concept kitchen, café, and gathering room, all bathed in natural light. This inviting space is perfect for both everyday living and entertaining. The kitchen boasts a large center island, a convenient storage pantry, and top-of-the-line Whirlpool stainless steel appliances—including a refrigerator and vented microwave. Tilden white cabinetry, decorative tile backsplash, and quartz countertops complete the sophisticated look. For added convenience, the first floor includes a powder room and coat closet. Upstairs, you’ll find the private owner’s suite, two additional bedrooms, a second full bathroom, a loft, and a laundry closet. The owner’s suite is a true retreat, featuring a walk-in closet and a luxurious en suite bathroom with a frameless glass-enclosed shower, quartz-topped dual vanity, private water closet, and linen closet. Throughout the entire first floor enjoy wood-look luxury vinyl plank flooring, while tile flooring spans the laundry room and bathrooms. Plush, stain-resistant Shaw carpet covers the stairs, loft, and bedrooms, adding comfort and style. Smart home features include a smart thermostat, a smart doorbell, and additional LED downlights—ensuring your home is as connected as it is stunning. This new construction home perfectly blends luxury, convenience, and modern design, making it the ideal place to live and unwind.
16968 HAMLIN OASIS LOOP, WINTER GARDEN, FL 34787
$570,0007 Days on yellowkey MLS ID: O6427350
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2088 Built: 2025Monthly Fee: $210 Tax: $2,525 (2025)Community: Hamlin PointeSingle Family
Taxes:$2,525
Remarks: Welcome to this beautiful like-new residence in the highly desirable Hamlin Pointe community, located in the heart of Hamlin/Horizon West, one of the fastest-growing and most sought-after areas in Central Florida. Thoughtfully designed for modern living, this home offers 4 bedrooms, 3 full bathrooms, and a spacious loft, providing flexibility for families of all sizes. The first-floor bedroom is ideal for guests, multigenerational living, or a private home office. Upstairs, you'll find the remaining bedrooms, including the spacious primary suite featuring abundant natural light, a large walk-in closet, and a private en-suite bathroom. A charming covered front porch welcomes you into a bright, open-concept floor plan with generous living and dining areas, perfect for both everyday living and entertaining. The contemporary kitchen is beautifully appointed with wood cabinetry, a large center island, breakfast bar, and a complete stainless steel appliance package, combining style, elegance, and functionality. The location is simply exceptional. Just minutes from Hamlin Town Center, you'll enjoy an outstanding selection of restaurants, cafés, shopping, grocery stores, fitness centers, and entertainment, including Cinépolis Luxury Cinemas. The home is also conveniently located near Orlando Health Horizon West Hospital, the new OCOM campus, top-rated schools, SR-429, Walt Disney World, Orange County National Golf Center, and the future Surf Park, making daily commuting and recreation effortless. This move-in-ready home combines modern design, an unbeatable location, and exceptional value in one of Winter Garden's most desirable communities. Don't miss this incredible opportunity to make this exceptional property your new home!
Listing Agent: Jardel Pizzolato Bittencourt (407-234-4953)
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