Location: Winter Garden , 34787
Do Not Show Listings
833 BENDING OAK TRL, WINTER GARDEN, FL 34787
$425,0005 Days on yellowkey MLS ID: O6403683
REDUCED by $10,000 (2.3%) on 05/13/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1789 Built: 2009Monthly Fee: $447 Tax: $4,032 (2025)Community: Oaks/Brandy Lake OTownhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,032
Elementary School: Tildenville Elem
High School: West Orange High
Tax Year: 2025
Middle School: Lakeview Middle
Remarks: Beautifully maintained and truly turn-key, this 3-bedroom, 2.5-bath townhome is the kind of home where you can simply move in and start enjoying everything Winter Garden has to offer from day one, all while being located in the highly sought-after Golf Cart District just moments from the heart of charming Downtown Winter Garden! From the moment you walk in, you’re welcomed by bright, open living spaces, thoughtful design, and timeless finishes that make the home feel warm, elevated, and instantly inviting. Plantation shutters throughout add that polished custom touch, while the open-concept layout creates the perfect flow for both everyday living and entertaining. Upstairs, the spacious primary suite feels like its own private retreat, thoughtfully positioned away from the guest rooms so you can truly enjoy your own space. Wake up to beautiful open skies and unwind each evening with stunning sunset views right from your bedroom. This is townhome living exactly how it should be. Where else in Winter Garden can you enjoy a home like this, have pool access just a short walk away, and spend your weekends enjoying life instead of worrying about exterior upkeep? Lock it, leave it, travel when you want, and come home to a space that always feels effortlessly cared for. And the location? It’s hard to beat! Bending Oak Trail offers that true neighborhood feel with peaceful evening walks, friendly neighbors, and a sense of community that makes you feel right at home, all while being just moments from the heart of Downtown Winter Garden—one of Central Florida’s most beloved downtowns, known for its brick-lined streets, incredible local restaurants, charming boutiques, cozy coffee shops, weekend Farmer’s Market, and year-round community events that make this area so special. Hop on your golf cart and head down Plant Street for your morning coffee, dinner with friends, shopping, or an evening stroll. Even better, you’re right next to the West Orange Trail, making morning bike rides, walks, and outdoor living part of your everyday lifestyle. With quick access to 429, the Turnpike, SR-50, Disney, Downtown Orlando, and Orlando International Airport, convenience is seamlessly built into daily life. Winter Garden continues to be one of Central Florida’s most sought-after communities, and opportunities to own something this move-in ready, this well-located, and at this price point are incredibly hard to find.
Listing is courtesy of: GLOBAL FLORIDA REALTY (407-380-3030)
Listing Agent: Lauren Bouchard (352-978-6837)
6212 ARALIA IVY LN, WINTER GARDEN, FL 34787
$434,90047 Days on yellowkey MLS ID: O6394386
REDUCED by $5,100 (1.2%) on 05/06/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1560 Built: 2020Monthly Fee: $289 Tax: $6,732 (2025)Community: Hamilton Gardens Ph 2A & 2BTownhouse
Taxes:$6,732
Elementary School: Hamlin Elementary
High School: Horizon High School
Middle School: Hamlin Middle
Remarks: LOCATION! LOCATION! LOCATION! Take advantage of $5,000 in seller concessions! This spacious and beautiful two-story townhome offers the perfect blend of comfort, privacy, and convenience in the highly desirable Hamilton Gardens community. Enjoy an open-concept floor plan, freshly painted interior, and a private outdoor courtyard leading to a rear-entry two-car detached garage. The bright kitchen features granite countertops, a spacious pantry, and overlooks the dining area and great room, creating a seamless space ideal for entertaining. Large windows with blinds fill the home with natural light, enhancing the open feel throughout. Storage is abundant with a pantry, an under-stairs closet, and a generous walk-in closet in the owner’s suite. Upstairs, you’ll find 3 generous bedrooms, 2 bathrooms, and a convenient second-floor laundry. The owner’s suite boasts an enormous walk-in closet and peaceful views of beautiful mature trees. With no neighbors behind, this home offers a quiet, private setting that’s truly rare. Hamilton Gardens provides exceptional amenities, including a resort-style beach-entry pool, cabana, dog park, sports lawn, playgrounds, and scenic garden paths. Residents also enjoy nightly views of the Disney fireworks right from the community. Located just moments from Hamlin Town Center, you’ll have restaurants, cafés, entertainment, and a weekly farmers market less than a mile away. Convenient to SR 429, A-rated schools, top medical facilities, Winter Garden Village, Historic Downtown Winter Garden, and Windermere. A perfect combination of privacy, convenience, and resort-style living—come see it today!
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Olga Recean (253-285-2595)
921 BENDING OAK TRL, WINTER GARDEN, FL 34787
$575,0005 Days on yellowkey MLS ID: O6405328
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2481 Built: 2012Monthly Fee: $125 Tax: $3,791 (2025)Community: Oaks/Brandy Lake 01 Rep A & BSingle Family
Taxes:$3,791
Remarks: One or more photo(s) has been virtually staged. Welcome home to 921 Bending Oak Trail in highly sought-after, downtown, golf cart district of Winter Garden! This spacious 4-bedroom, 2.5-bath home is perfectly situated on a private oversized corner lot with serene pond views, offering both privacy and a peaceful backdrop. The thoughtfully designed layout features a first-floor primary suite and convenient downstairs laundry room. The main living areas showcase updated modern, stone-like tile flooring, while the kitchen offers a large walk-in pantry that extends under the staircase for exceptional storage. The spacious Living Room and covered patio are wired for a surround sound system and have beautiful water views from the windows and paver patio. Upstairs, you’ll find generously sized secondary bedrooms, including one with an oversized walk-in closet, along with a large loft ideal for a home office, playroom, or flex space, all featuring engineered hardwood flooring. Enjoy outdoor living with a spacious entertaining area and the added benefit of a rear-entry garage accessed through a private, owners-only alleyway where you can also enter the home without climbing any stairs. Major updates include a roof replacement in 2025, making this home as practical as it is beautiful. Lastly, the location is incredible, the neighborhood is extremely well maintained, offering a tranquil walking community around Brandy Lake and duck filled ponds, a sparkling community pool, entertaining pavilion, community greenspace, and perfect playground for the little ones.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Claire Sims Llc (203-767-8109)
6044 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787
$579,820Listed 05/13/2026 2:42PM MLS ID: G5112346
0 Days Off yellowkey (back on 5/13/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2102 Built: 2026Monthly Fee: $150Community: Avalon WoodsSingle Family
Taxes:$0
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity in Avalon Woods! Discover the newest community by Dream Finders Homes in highly sought-after Hamlin, Winter Garden. Welcome to the Berkley, a thoughtfully designed bungalow that blends charm, functionality, and modern comfort. This brand-new home offers 4 bedrooms, 3 bathrooms, and 2,102 sq. ft. of living space. The inviting front porch sets the tone, while inside, abundant natural light flows through thoughtfully placed windows. A bedroom and full bath on the first floor provide flexibility for guests or multi-generational living, while the upstairs keeps the remaining bedrooms together for privacy. Enjoy seamless indoor-outdoor living with a covered breezeway and private courtyard, perfect for gatherings or a quiet retreat. Nestled in Avalon Woods, you’ll love the convenience of being just minutes from top-rated schools, Hamlin Town Center, Hwy 429, and Disney.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
15401 PORTER RD, WINTER GARDEN, FL 34787
$549,900134 Days on yellowkey MLS ID: S5140743
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2455 Built: 2015Monthly Fee: $242 Tax: $8,271 (2024)Community: SummerlakeSpa: NoSingle Family
Taxes:$8,271
Elementary School: Summerlake Elementary
Tax Year: 2024
Remarks: (3D tour link attached!) Welcome to this well-appointed single-family home offering 2,455 sq. ft. of living space in the desirable Winter Garden area. Featuring 5 bedrooms and 3 full bathrooms, this residence provides generous space and flexibility for comfortable everyday living, guests, or work-from-home needs. All the bedrooms upstairs and the stairs are laminate flooring. Only the bedroom downstairs is carpet. The thoughtfully designed floor plan includes multiple living areas and a layout well suited for both relaxation and entertaining. With five bedrooms, the home offers versatility for growing households or those seeking additional space. Situated within a welcoming residential community, residents enjoy sidewalk-lined streets, green spaces, and a neighborhood-friendly atmosphere ideal for outdoor enjoyment and daily walks. When using our preferred lender, the buyer will receive a 1 percnt lender credit of the loan amount, which can be applied toward closing costs or an interest rate buydown. Conveniently located near major roadways, this home offers easy access to shopping, dining, parks, and schools, and is just a short drive from Walt Disney World, making it an excellent option for a primary residence, vacation home, or investment opportunity. This property presents a wonderful opportunity to enjoy space, location, and community living in one of Central Florida’s most sought-after areas.
Listing is courtesy of: MULTI CHOICE REALTY LLC (352-404-6542)
Listing Agent: James Song (407-405-3140)
16229 PEBBLE BLUFF LOOP, WINTER GARDEN, FL 34787
$479,00013 Days on yellowkey MLS ID: O6403777
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1685 Built: 2018 Tax: $7,243 (2025)Community: Waterleigh Ph 2ASingle Family
Taxes:$7,243
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to this cozy house in Waterleigh Winter Garden! When you walk in the door, a beautiful porch welcomes you, as you enter the foyer, you’ll find two guest bedrooms that share a full bathroom. As you continue into the home you will find the well-appointed kitchen overlooks the family room, dining room, and outdoor lanai. This home features a spacious kitchen island with built in sink and dishwasher to optimize counter space, and walk-in pantry for extra storage. Waterleigh is located just a short drive to nearby shopping, dining and major entertainment attractions, minutes from Disney, Hamlin, I-4, turnpike and 429. The community features 2 fitness centers in the clubhouses with ballroom, theater, grill and screened room , 3 resort style pools , dog parks, beach volleyball courts, tennis courts, mini golf court, HOA includes of all landscape maintenance. Publix plaza and A rated schools are mins away. Call to schedule a showing today!
Listing is courtesy of: U KEY REALTY (407-937-8888)
Listing Agent: Yukey Hoo (407-937-8888)
16776 BROADWATER AVE, WINTER GARDEN, FL 34787
$1,324,000Listed 05/13/2026 7:59AM MLS ID: O6407043
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3713 Built: 2018Monthly Fee: $383 Tax: $9,438 (2025)Community: Waterside/Johns Lk-Ph 1Spa: YesSingle Family
Taxes:$9,438
Remarks: Positioned on a premium homesite with an expansive manicured common area along one side, this property offers added privacy and open space, along with sweeping views of John’s Lake from the front of the home. Inside, the home opens to a formal dining area accented by wood beam ceilings, while custom wall details in the foyer and along the staircase add a refined, designer touch. The main living area features soaring ceilings, abundant natural light, wood beam ceiling accents, and a striking floor-to-ceiling accent wall, creating a dramatic yet inviting focal point that flows seamlessly into the dinette and open kitchen. Designed for both everyday living and entertaining, the kitchen includes a large island with seating, sleek cabinetry, stainless steel appliances, a gas cooktop, built-in oven, and generous pantry space. Just off the pantry, a connecting space between the kitchen and dining room offers the perfect opportunity for a coffee station or butler’s pantry. The main level also offers a spacious primary suite with a well-appointed bath and a custom walk-in closet featuring built-in drawers, cabinetry, and shelving, along with a secondary bedroom and full bath, ideal for guests or multigenerational living. Upstairs, you will find three additional bedrooms, including one with a private bath, while the remaining two share a full bath, plus a generous loft overlooking the living area that provides flexible space for a secondary living area, home office, or play space. The outdoor living space is designed for true Florida living, featuring a saltwater pool and spa added in 2021 with full automation, expansive Travertine tile decking, and a lanai with a motorized screen that extends your living space year-round. The patio is also pre-plumbed for a future outdoor kitchen, offering even more potential for entertaining. Additional highlights include a split three car garage configuration with a separate side entry one car bay and a 2 car garage equipped with an EV charging outlet. Waterside on John’s Landing offers a clubhouse, fitness center, resort-style pool, playground, covered dock, and pavilion on John’s Lake, all conveniently located near Horizon West, Hamlin, shopping, dining, and major roadways.
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Alex Vastardis (407-947-6264)
14501 GROVE RESORT AVE #2604, WINTER GARDEN, FL 34787
$205,00091 Days on yellowkey MLS ID: O6367873
REDUCED by $10,000 (4.7%) on 04/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1375 Built: 2009 Tax: $8,091 (2025)Community: Grove Residence & Spa Hotel Condo IiCondo
Taxes:$8,091
Elementary School: Water Spring Elementary
Middle School: Water Spring Middle
Remarks: Welcome! Just 15 minutes from Disney, this 2-bedroom, 2-bathroom unit resides on the sixth floor of the acclaimed Grove Resort & Water Park, a guard-gated, vacation-rental community, boasting a truly impressive array of amenities. On-site restaurants, two resort-style pools, and a water park with a lazy river, multiple pools, water slides, and a surf simulator is just the start. Situated at the heart of Orlando's vibrant attractions, the property offers daily transportation to and from the area's top destinations, placing endless activities at your fingertips. Dive into aquatic adventures at Discovery Cove or tee off at some of Orlando's finest golf courses near Disney World. Explore the enchanting Walt Disney World Resort with its four captivating theme parks or seek thrills at Universal Studios three exciting parks, including their newest addition, Epic Universe. With an onsite management team ready to handle the heavy lifting, this unit is ready for a new owner. Don’t miss your chance and schedule your private tour today.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY (407-203-0007)
Listing Agent: Joseph Doher (407-203-0007)
15334 MURCOTT BLOSSOM BLVD, WINTER GARDEN, FL 34787
$430,00054 Days on yellowkey MLS ID: O6392207
REDUCED by $20,000 (4.4%) on 05/01/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1868 Built: 2017Monthly Fee: $353 Tax: $6,791 (2025)Community: Highlands/Summerlake Grvs Ph 1Townhouse
Taxes:$6,791
Remarks: Beautiful 3-bedroom, 2.5-bathroom townhouse available in the great Summerlake community of Winter Garden. This home features an open floor plan, spacious living areas, and a 2-car garage. An additional room at the front of the house offers the perfect space for a home office or flex room. The Summerlake community provides exceptional amenities, including a pool, playground and dog park. Conveniently located near A-rated schools – Summerlake Elementary, Hamlin Middle, and Horizon High. Nestled in the heart of Winter Garden, this home is just minutes from world-class shopping, dining, and entertainment. Enjoy proximity to Disney, major highways, and the bustling Hamlin Town Center. Winter Garden is known for its charming downtown, weekly farmers markets, and vibrant community events, making it one of Central Florida’s most desirable places to live.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Ligia Coelho (321-888-0461)
7190 ENCHANTED LAKE DR, WINTER GARDEN, FL 34787
$545,0006 Days on yellowkey MLS ID: O6402423
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2113 Built: 2016Monthly Fee: $253 Tax: $5,148 (2025)Community: Lakeview Pointe/Horizon West PSingle Family
Taxes:$5,148
Remarks: Welcome to 7190 Enchanted Lake Drive—your exclusive gateway to the vibrant Horizon West lifestyle. Seize the rare opportunity to own a highly sought-after 4-bedroom, 3-bathroom residence in the coveted Lakeview Pointe community, where modern luxury meets unmatched convenience. This beautifully maintained 2,294 sq. ft. home is designed for effortless entertaining, featuring an expansive open-concept first floor where abundant natural light creates a warm and inviting atmosphere. The upgraded chef's kitchen is an absolute showstopper, boasting 42-inch white cabinets, a new KitchenAid dishwasher, and a convection range. It flows seamlessly into the main living spaces, making it the perfect centerpiece for both intimate family meals and lively gatherings. Step outside to your private screened patio—an idyllic outdoor oasis designed for relaxing in the Florida breeze year-round. Everyday practicality is beautifully elevated by a charming covered walkway leading to the detached 2-car garage, while the freshly painted exterior ensures striking curb appeal and long-term durability. Inside, experience a higher standard of living with custom built-in closets throughout, offering premium storage solutions rarely found at this price point. Best of all, you can end your evenings on the cozy front porch, the ultimate spot to unwind and take in the spectacular nightly Disney fireworks—a truly magical and unique feature that makes this house feel like home.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Mark Gardner (689-248-8585)
168 WINDTREE LN #203, WINTER GARDEN, FL 34787
$209,500212 Days on yellowkey MLS ID: O6351954
REDUCED by $400 (0.2%) on 05/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 918 Built: 1985Monthly Fee: $260 Tax: $2,004 (2024)Community: Windtree Gardens Ph 6Condo
Taxes:$2,004
Remarks: One or more photo(s) has been virtually staged. **BACK ON MARKET: Owner Paused listing to fully remodel the home!** This 2-bedroom, 2-bath second-floor condo in the sought after community of Windtree Gardens is truly a must see now! LOW HOA! Featuring New kitchen cabinets, New quartz countertops, New appliances, New luxury vinyl-plank flooring throughout, New bathroom vanities, New fans and fixtures, and fresh interior paint. Conveniently located walking distance to Starbucks, less than 2 miles to the 429, and just minutes from dining and shopping! Come see this home today, before it goes!!!
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erik Mcginnis (407-948-6518)
15976 CITRUS KNOLL DR, WINTER GARDEN, FL 34787
$909,00021 Days on yellowkey MLS ID: O6399342
1 Days Off yellowkey (back on 5/13/2026)
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2953 Built: 2015Monthly Fee: $235 Tax: $11,413 (2025)Community: Hickory Hammock Ph 1DSpa: NoSingle Family
Taxes:$11,413
Elementary School: Whispering Oak Elem
Remarks: Under contract-accepting backup offers. FULLY FURNISHED, HEATED POOL HOME IN A GATED COMMUNITY WITH TOP-RATED SCHOOLS AND RESORT-STYLE AMENITIES — A TRUE TURNKEY OPPORTUNITY. This stunning one-story home, located in the highly desirable gated community of Hickory Hammock in Winter Garden, is loaded with upgrades. Situated on a premium corner lot, the property features a fully fenced yard with a heated saltwater pool, travertine deck, and a versatile basketball court, all surrounded by additional green space—perfect entertaining, kids and pets. Inside, the open-concept layout centers around an oversized Silestone kitchen island, creating a seamless flow between the main living areas. The home offers a thoughtfully designed floor plan with generous living, ideal for keeping the family connected and hosting. Designer upgrades throughout include engineered hardwood flooring, crown molding, upgraded lighting, window treatments, motorized shades, and a 4-zone A/C system allowing customized temperature control across the home. Additional features include a security system, outdoor surround sound, and a termite bond for added peace of mind. This home is being sold fully furnished and truly turnkey, featuring high-quality pieces from Z-Gallerie, Pottery Barn, Sealy, Samsung, Sony, LG, GE, and Char-Broil. Residents of Hickory Hammock enjoy resort-style amenities, including a clubhouse, community pool, fitness center, tennis and volleyball courts, playgrounds, walking trails, dog park, and fishing pier. Conveniently located near Downtown Winter Garden, shopping, dining, Disney, major highways, and Orlando International Airport, and zoned for top-rated schools, this home offers the best of Central Florida living. A full list of upgrades is available in the attachments.
Listing Agent: Mariana Cezar Ovalle (407-427-3559)
225 SOUTHERN PECAN CIR #208, WINTER GARDEN, FL 34787
$288,90070 Days on yellowkey MLS ID: O6383422
REDUCED by $1,000 (0.3%) on 05/13/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1264 Built: 2005 Tax: $3,728 (2025)Community: Southern Pines CondoCondo
Taxes:$3,728
Elementary School: SunRidge Elementary
Middle School: SunRidge Middle
Remarks: Beautiful 2-bedroom, 2-bathroom condo just under 1,300 sq ft in one of the most desirable areas of Winter Garden. Both bedrooms feature large walk-in closets, and the layout is exceptionally well designed, making the home feel spacious and comfortable. The unit COMES WITH A 1-CAR GARAGE, a rare and valuable feature. All appliances are BRAND NEW, including refrigerator, microwave, stove, and dishwasher. A washer and dryer are also included. The flooring has been completely renovated to elegant wood flooring throughout. The main living area offers a separate flex space that is PERFECT for a home office or a kids’ play area. Conveniently located next to the community car wash, with resort-style amenities that include an amazing clubhouse, pool area with barbecue grills, fully equipped gym, tennis courts, basketball courts, and more.
Listing is courtesy of: JOHN SILVA REALTY & ASSOCIATES (407-420-7908)
Listing Agent: John Silva (407-420-7908)
617 MARSH REED DR, WINTER GARDEN, FL 34787
$759,00014 Days on yellowkey MLS ID: O6402724
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2828 Built: 2016Monthly Fee: $128 Tax: $5,746 (2025)Community: Johns Lake PointeSingle Family
Taxes:$5,746
Remarks: From the moment you arrive, this home feels like a place to slow down, settle in, and truly enjoy the best of Winter Garden living. Set within a quiet community, it offers a welcoming blend of comfort, natural light, and thoughtfully designed spaces that make everyday life feel just a little more special. Inside, the home is filled with bright, natural light that enhances its open and inviting feel. Careful attention to design creates a sense of warmth and refinement throughout, offering spaces that are both functional and comfortable for daily living or hosting guests. Step outside to a stunning covered pool area that becomes the heart of the home. Whether you are enjoying a quiet morning or gathering with friends, this private outdoor space offers the perfect setting to relax and unwind while taking full advantage of Florida living year-round. The surrounding community adds another layer of appeal, offering access to amenities such as a clubhouse, pool, and tennis courts that support both recreation and connection. The neighborhood setting encourages time outdoors while maintaining a peaceful and well-kept environment. Location is where this home truly shines. Just minutes from the vibrant Horizon West and Hamlin area, you will enjoy easy access to shopping, dining, and everyday conveniences. Nearby major roadways make commuting and travel simple, while local attractions and outdoor spaces provide endless opportunities to explore and enjoy your surroundings. This home offers a unique balance of comfort, convenience, and lifestyle, creating a space where both everyday moments and special occasions feel effortless. Schedule your private showing to experience it in person and see how it fits your next chapter.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Stacey Vazquez (407-874-5751)
634 FOSTER AVE, WINTER GARDEN, FL 34787
$285,000163 Days on yellowkey MLS ID: TB8451057
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 696 Built: 1951 Tax: $3,778 (2024)Community: Westchester PlaceSpa: NoSingle Family
Taxes:$3,778
Remarks: Charming bungalow that's been completely renovated and is now move-in ready! Rebuilt down to the studs in 2022, with all-new systems and finishes, new roof, electrical, plumbing, central HVAC, flooring and appliances, makes it a very solid investment—whether as a starter home or potentially as a bed-and-breakfast (B&B) option. With two bedrooms and one bath, this bungalow would make for a cozy and functional space. The inside laundry is a great modern convenience, and a breakfast bar is perfect for casual meals. Walking distance to Plant Street the vibrant downtown area of Winter Garden, known for its historic charm and many local businesses. You will enjoy access to the popular indoor artisan food hall, a craft brewery, restaurants, and shops. Outdoor enthusiasts will love being close to West Orange bike trail and Veterans Memorial Park. It is a 2 minute walk to Colonial and Hyde Park bus stop.
Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)
Listing Agent: Stephen Hachey (813-642-6030)
9218 HOLLISTON CREEK PL, WINTER GARDEN, FL 34787
$920,00074 Days on yellowkey MLS ID: O6386394
REDUCED by $7,900 (0.9%) on 05/13/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3087 Built: 2018Monthly Fee: $164 Tax: $11,801 (2025)Community: Watermark Ph 2BSpa: NoSingle Family
Taxes:$11,801
Elementary School: Panther Lake Elementary
Remarks: Delight your clients with this unique opportunity in Watermark, one of the most desirable communities in Winter Garden. This elegant two-story residence combines sophistication, comfort, and impeccable finishes in every detail, featuring over $150,000 in upgrades that elevate the home’s overall quality and value. It offers 4 bedrooms, 3 full bathrooms, and 1 powder room, along with a simply enchanting outdoor area designed to provide unforgettable moments. Upon entering, a spacious and welcoming foyer leads to open-concept living areas, where the living room and dining room connect harmoniously, creating a bright and airy space ideal for entertaining family and friends. The beautiful porcelain tile floors enhance the elegance of the property. The kitchen is a true highlight, equipped with appliances, high-quality wood cabinetry, and ample countertop space, combining functionality and style for everyday living. On the second floor, all bedrooms provide greater privacy and comfort. The bedrooms feature closets and carpeting, creating a cozy atmosphere. The primary suite is a special retreat, featuring two walk-in closets and a spacious bathroom with dual sinks, offering both practicality and sophistication. The laundry room is also located on the upper floor and includes a sink, washer, and dryer, providing added convenience to the family’s routine. Outside, the property impresses with a fully equipped summer kitchen featuring a built-in grill, granite countertops, cabinetry, and a sink — perfect for gatherings and family moments — integrated with a private heated pool, allowing year-round enjoyment with comfort and exclusivity. Living in Watermark means enjoying resort-style amenities, including a community pool, modern fitness center, tennis court, playground, green areas, and tree-lined sidewalks for outdoor walks. The location is another major advantage: just minutes from Hamlin Town Center, with excellent restaurants, cafés, movie theater, and supermarkets; easy access to Walt Disney World Resort; and close to Florida State Road 429, providing convenient access to Orlando and the entire region. Additionally, it is surrounded by highly rated schools and all the conveniences that Winter Garden offers. A complete home, offering leisure, comfort, and a prime location. Don’t miss the opportunity to live or invest in one of the best addresses in the region.
Listing Agent: Gustavo Carneiro (407-758-4001)
1966 PANTHEON DR, WINTER GARDEN, FL 34787
$525,00068 Days on yellowkey MLS ID: O6386961
REDUCED by $25,000 (4.5%) on 04/09/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2076 Built: 2015Monthly Fee: $211 Tax: $5,734 (2024)Community: Alexander RidgeSingle Family
Taxes:$5,734
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. ONE STORY 4-bedroom, 3-bathroom home in desirable Winter Garden / Horizon West. This well-maintained home offers 2,076 square feet and is ready for your vision with the opportunity for a light refresh to make it your own. Looking for the convenience of a one-story single-family home without the upkeep of a larger yard? Step outside to a FULLY FENCED outdoor space with just enough room to enjoy it all…a covered outdoor entertaining area plus extra space for a small play area or dog run. The main living area is open and inviting, while the bedrooms are nicely tucked away to provide privacy. The kitchen features a walk-in pantry, kitchen island with seating, and plenty of cabinets! The spacious primary suite features a tray ceiling, large walk-in closet, and an en-suite bathroom with double vanities, a garden tub, and a separate walk-in shower. The DEDICATED laundry room conveniently connects to the primary bathroom and also has access from the kitchen. WASHER AND DRYER are included. Three additional bedrooms and two full bathrooms provide flexibility for guests, family, or a home office. NO MOWING HERE....LAWN CARE IS INCLUDED in your HOA dues! The community features a pool, clubhouse, and playground, along with green space and sidewalks that make it perfect for biking or walking. Conveniently located minutes from shopping, dining, and everything Horizon West has to offer, with quick access to the 429 Expressway for easy travel throughout Central Florida. The home also offers convenient access to Walt Disney World Resort and other area attractions, making this location especially appealing for those who enjoy everything the area has to offer.
Listing is courtesy of: SIMPLY HOME REALTY (407-920-2016)
Listing Agent: Beth Yannoulis (407-920-2016)
1698 JUNIPER HAMMOCK ST, WINTER GARDEN, FL 34787
$1,450,00026 Days on yellowkey MLS ID: V4948569
Bed: 7 Bath: 4.0 Gar: 4 Liv Area Sq Ft: 4700 Built: 2019Monthly Fee: $97 Tax: $9,199 (2025)Community: Mcallister LndgSingle Family
Taxes:$9,199
Remarks: Experience refined Florida living in this stunning energy-efficient estate, perfectly positioned on an expansive corner lot in the highly sought-after Winter Garden area. Just minutes from Historic Downtown Winter Garden and within close proximity to Orlando’s world-renowned theme parks, this exceptional residence offers the ideal blend of elegance, comfort, and convenience. This impressive two-story home features 7 spacious bedrooms and 4 beautifully appointed bathrooms, thoughtfully designed to accommodate multi-generational living. A luxurious owner’s suite and guest bedroom on the main floor provide flexibility and privacy, while five additional bedrooms are situated upstairs on either side of a generous game room and private home theater, creating the ultimate setting for entertainment and relaxation. At the heart of the home lies a chef-inspired gourmet kitchen, complete with a breakfast bar, and café dining area, all seamlessly flowing into the expansive family room and overlooking the covered lanai. Elegant upgraded tile plank flooring enhances the main living areas, while plush carpeting adds comfort to the bedrooms and bonus spaces. Formal living and dining rooms, provide both sophistication and functionality. Step outside to your private backyard oasis, where a gorgeous in-ground swimming pool, summer kitchen, and oversized covered lanai create the perfect environment for year-round entertaining. The fully fenced yard ensures privacy and ample space for outdoor enjoyment. Car enthusiasts and active families will appreciate the three-car tandem garage with an additional single-car bay, ideal for extra parking, storage, or a golf cart. Modern smart home technology enhances convenience and security, while the home’s energy-efficient construction promotes a healthier, quieter lifestyle and significant savings on utility costs. Residents also enjoy access to exceptional community amenities, including a dock on Lake Apopka, scenic parks, and walking trails, all contributing to the vibrant and active Winter Garden lifestyle.
Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-862-9966)
Listing Agent: Nell Adams (386-315-3967)
10291 ATWATER BAY DR, WINTER GARDEN, FL 34787
$1,274,500303 Days on yellowkey MLS ID: O6326819
REDUCED by $25,000 (1.9%) on 04/01/2026
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3910 Built: 2019Monthly Fee: $250 Tax: $15,141 (2024)Community: Waterleigh Ph 2BSingle Family
Taxes:$15,141
Remarks: OFFERED with a 2021 LOWE PONTOON BOAT! Lakefront Luxury in Waterleigh with Private Dock and Fireworks Views. Welcome to the perfect blend of comfort, function, and lakeside living in the highly sought-after Waterleigh community. This spacious home sits on a fully fenced 1/3-acre lot with over 100' fronting the lake in the back and 90'+ of open green space to the side; featuring a private dock with low-maintenance composite boards, a pontoon boat lift, and a peaceful sitting area—offering a front-row seat to nightly Disney fireworks from your dock or living room. Inside, no detail has been overlooked. The home boasts durable wood-look tile downstairs and luxury vinyl plank flooring upstairs—no carpet in sight. The open-concept layout seamlessly connects the kitchen, dining, and family rooms, all with stunning lake views. The kitchen is a chef’s dream, complete with 42” cabinets, a 4-seat island, 5-burner stove, double convection oven, butler’s pantry, walk-in pantry, and built-in wine rack. The extra-large primary suite is located on the first floor and showcases crown molding, tray ceiling, huge walk-in closet and serene lake views. The primary bathroom is a dream with quartz counters, dual vanities, a makeup counter, and a walk-in double shower. Upstairs, a versatile loft offers the ideal space for a game room, media room, or second living area. All bedrooms are generously sized with walk-in closets, and there’s no shortage of storage with additional closets throughout. Work from home in the dedicated office, enjoy surround sound in the family room (pre-wired for 5.1), and take advantage of the spacious laundry room with built-in cabinetry and counter space. The 3-car garage features epoxy flooring, and the home is pre-wired for a pool if you wish to expand your outdoor living. Waterleigh offers unmatched amenities including resort-style pools, playgrounds, sports fields, fitness centers, and even a Publix right at the entrance. Lawn, landscape and irrigation maintenance are included with the HOA dues, and you're just minutes from the 429, Disney, shopping, dining, and top-rated schools. This is Florida living at its best.
Listing is courtesy of: REVEL REALTY LLC (407-876-6448)
Listing Agent: Chris Sapp (407-574-1002)
9940 BLACK BEAR LN, WINTER GARDEN, FL 34787
$2,050,000362 Days on yellowkey MLS ID: O6309917
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 3110 Built: 2027 Tax: $4,423 (2024)Community: Acreage & UnrecSingle Family
Taxes:$4,423
Remarks: Pre-Construction. To be built. This Custom Single-Story Modern Farmhouse by Lionshead Homes is a showstopper! Set on a serene 5-acre private oasis. Plenty of space for farm animals or just enjoy the open space and tranquil surroundings. Lionshead Homes has recently built custom homes near this property. So Buyers may view a recently completed home to get an idea of fit and finish and our quality craftmanship. Located in the Avalon Rural Settlement, you'll enjoy the country lifestyle without sacrificing proximity to shopping, entertainment and the suburban lifestyle of Hamlin and Winter Garden. Call for more information or to schedule a viewing appointment.
Listing is courtesy of: HAMLIN REALTY (321-299-4279)
Listing Agent: Edward Guerrette Llc (321-299-4279)
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