Displaying: For Sale
Location: Winter Garden
Property Type(s): Single Family
Price: $400,000 to $499,000
Do Not Show Listings
Winter Garden - 36 properties found
16385 ADMIRALS COVE LN, WINTER GARDEN, FL 34787
$469,90040 Days on yellowkey MLS ID: O6393056
REDUCED by $100 (0.0%) on 04/27/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1705 Built: 2020Monthly Fee: $257 Tax: $4,805 (2025)Community: WaterleighSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,805
Elementary School: None
High School: Horizon High School
Tax Year: 2025
Middle School: Water Spring Middle
Remarks: Unique financing opportunities make this Waterleigh home a standout. Eligible VA buyers may have the rare chance to assume the seller’s incredibly low 2.5% interest rate, while non-military buyers can take advantage of a 2-1 buy-down paid by the seller’s preferred lender for added affordability and potential monthly savings in today’s market. Plus, the sellers are now offering $5,000 in concessions! This beautifully maintained 3-bedroom, 2-bath home features a bright, open-concept layout designed for both everyday living and easy entertaining. The spacious kitchen is the heart of the home, complete with stainless steel appliances, a walk-in pantry, and a large center island. The private owner’s suite offers a relaxing retreat with a generous walk-in closet and en-suite bath. Located in highly sought-after Waterleigh in Winter Garden, this home offers the lifestyle buyers are looking for, with golf cart-friendly streets, resort-style amenities, breathtaking Disney fireworks views, and the added convenience of a pool and playground directly across the street. Two schools are also located within the community, making this location as practical as it is desirable. Schedule your private showing today!
Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)
Listing Agent: Shaheda Gordon-Jefferson (646-456-7410)
107 TRADITIONS DR, WINTER GARDEN, FL 34787
$474,97548 Days on yellowkey MLS ID: S5145650
REDUCED by $25,020 (5.0%) on 04/20/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1582 Built: 1999Monthly Fee: $45 Tax: $1,458 (2024)Community: Traditions SubSingle Family
Taxes:$1,458
Elementary School: Dillard Street Elem
High School: West Orange High
Tax Year: 2024
Middle School: Lakeview Middle
Remarks: You found it with this Location! The family will love this beautiful, Former Model home in Traditions! Blocks away from Downtown Winter Garden! Golf carts welcome! This 3/2 split plan has wood laminate flooring in living room & the master bedroom. Kitchen is open, Ceramic tile & eat-in space overlooking backyard. Master Bedroom is spacious with Walk-in shower and separate tub. Big backyard fully fenced. Enjoy the restaurants, famer's market & shops all in walking distance or use a golf cart! Separate Workshop room in garage- perfect for the handyman. AC 2019. Easy access to the turnpike, 429, 408 to downtown Orlando or OIA! Great Schools! Solar panels will be paid off at closing!
Listing is courtesy of: WATSON REALTY CORP (407-298-8800)
Listing Agent: Rick Evans, Ii (407-538-9295)
9355 TYRELLA PINE TRL, WINTER GARDEN, FL 34787
$475,00040 Days on yellowkey MLS ID: O6391856
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1670 Built: 2016Monthly Fee: $148 Tax: $657 (2025)Community: Watermark Ph 1BSingle Family
Taxes:$657
Elementary School: Panther Lake Elementary
Middle School: Hamlin Middle
Remarks: One or more photo(s) has been virtually staged. Experience the perfect blend of modern upgrades and an unbeatable location in this move-in-ready 3-bedroom, 2.5-bathroom home within the premier Watermark community. This residence has been meticulously maintained, boasting exterior paint (2023), a new garage lift (2024), and a brand-new water heater (2025). The home welcomes you with a huge covered front porch and an open-concept first level featuring tile flooring throughout, a chef-inspired kitchen with stainless steel appliances, rich cabinetry, and a breakfast bar. Upstairs, a versatile loft and convenient laundry room connect the primary suite to two generously sized guest bedrooms. Residents enjoy world-class community amenities including a resort-style pool, fitness center, tennis courts, and playground, all while being walking distance to the brand-new "The Mark" shopping center. Perfectly situated for families and commuters alike, zoned for Top Rated Schools, and just minutes from Hamlin Town Center, the 429 expressway, and Disney property. With alley-access parking and easy access to Winter Garden’s unique charm, this home offers the ultimate Horizon West lifestyle. Tour today!
Listing is courtesy of: REDFIN CORPORATION (407-708-9747)
Listing Agent: Jo Holton (307-690-7219)
16229 PEBBLE BLUFF LOOP, WINTER GARDEN, FL 34787
$479,0004 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
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)
2154 OAKINGTON ST, WINTER GARDEN, FL 34787
$469,9004 Days on yellowkey MLS ID: O6402495
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1585 Built: 2002Monthly Fee: $243 Tax: $5,166 (2025)Community: Stoneybrook WestSingle Family
Taxes:$5,166
Elementary School: Whispering Oak Elem
Middle School: SunRidge Middle
Remarks: Welcome to this beautifully maintained, single-story home that perfectly blends comfort, style, and functionality. From the moment you arrive, the manicured front yard and inviting entry to set the tone for what’s inside. Step into a bright, open living space filled with natural light from large windows. The formal living and dining area offers the perfect setting for entertaining guests or enjoying quiet evenings at home. The kitchen is updated and designed with both style and convenience in mind, featuring modern appliances, generous storage, and a breakfast bar ideal for casual meals. Just beyond, the spacious family room provides plenty of seating for gatherings, movie nights, or simply relaxing with friends and family. This home offers a desirable split floor plan with a primary suite, complete with an ensuite bathroom and a full-size soaking tub—perfect for unwinding at the end of the day. Two additional bedrooms share a well-appointed full bathroom, making it ideal for families or guests. Step outside to your own private back yard fully fenced yard features a covered, screened-in patio—perfect for enjoying Florida year-round. The home has a New Roof and A/C in 2023.
Listing is courtesy of: REAL LIVING R E SOLUTIONS (407-253-1377)
Listing Agent: Tony Marino (407-468-2004)
115 ZACHARY WADE ST, WINTER GARDEN, FL 34787
$496,000177 Days on yellowkey MLS ID: O6356997
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1780 Built: 2001Monthly Fee: $58 Tax: $5,467 (2024)Community: Lakeview Reserve 46/149Spa: NoSingle Family
Taxes:$5,467
Elementary School: Tildenville Elem
Remarks: One or more photo(s) has been virtually staged. In the heart of Winter Garden’s beloved Golf Cart District just moments from the charm of Plant Street where the scent of roasted coffee drifts through the air and neighbors wave as they roll past on their way to the Saturday morning Farmers Market lies a hidden gem tucked inside the gated lakeside community of Lakeview Reserve. The West Orange Trail echoes just beyond the gates guiding joggers, cyclists, and families toward the beating heart of historic downtown. Behind the oaks and quiet streets stands a home that tells a story of balance between small town charm and modern comfort Its open layout flows effortlessly kitchen with stainless steel appliances to a warm, inviting living room that opens onto a screened in back porch, blending indoor comfort with outdoor serenity. The setting offers a backdrop of calm that feels a world away from the bustle yet you’re still close enough to hop on your golf cart and be downtown for dinner in minutes. As you move through the home every space seems to adapt and invite. A flexible office with double doors makes the perfect work from home retreat while a cozy bonus area can transform into a playroom, fitness space, or second lounge. The primary suite was designed for rest and renewal featuring a garden tub dual sinks and a generous walk in closet all framed by thoughtful updates like a 2017 ROOF replacement, 2023 Electrical Panel updated, 2017 Vinyl Fence and fresh interior paint. Step outside and you’ll find what truly defines Florida living and gentle lake breeze that seems to whisper peace. Here every detail speaks relaxation every sunset feels like a private showing and every golf cart ride into town reconnects you to the pulse of this growing yet timeless community from the laughter spilling out of Crooked Can Brewery to the soft music drifting beneath the twinkle lights of Plant Street. And as night falls and the air cools, you’ll realize that isn’t just a home it’s a rare piece of Winter Garden’s soul waiting for its next chapter to be written.
Listing is courtesy of: RE/MAX EXCLUSIVE COLLECTION (407-447-2829)
Listing Agent: Carmelo Nuccio (321-441-6951)
1836 WINGED ELM PL, WINTER GARDEN, FL 34787
$435,00050 Days on yellowkey MLS ID: O6390771
REDUCED by $4,000 (0.9%) on 04/30/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1712 Built: 2005Monthly Fee: $55 Tax: $6,075 (2025)Community: Winter Garden Trls 01-3Single Family
Taxes:$6,075
Remarks: One or more photo(s) has been virtually staged. One or more photo(s) have been virtually staged to showcase the incredible potential of this beautiful home. A 100-Day Home Warranty is also available at closing, offering added peace of mind for the new owner. Welcome to your dream home in the highly desirable city of Winter Garden, where comfort, space, and location come together perfectly! This beautiful 4-bedroom, 2-bath residence offers a spacious and functional layout designed for both everyday living and effortless entertaining. Step inside to discover a private and relaxing primary suite featuring a walk-in closet, a luxurious soaking tub, and a separate walk-in shower—creating the perfect retreat at the end of the day. The modern kitchen is equipped with stainless steel appliances and a convenient breakfast bar, ideal for casual dining, morning coffee, or gathering with family and friends. Enjoy Florida living at its best with a screened-in patio, perfect for relaxing evenings or weekend get-togethers while enjoying the outdoor breeze. Additional highlights include a two- car garage, ample living space, and a layout designed with comfort in mind. Location is everything, and this home delivers! With quick and easy access to 429, commuting is a breeze. You'll also be just minutes from Downtown Winter Garden. With its prime location, desirable features, and move-in ready appeal, this home is an incredible opportunity you won’t want to miss. Schedule your private showing today before this Winter Garden gem is gone!
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Jeff Jones (205-902-3584)
236 DONALD DR, WINTER GARDEN, FL 34787
$465,00010 Days on yellowkey MLS ID: O6401940
2 Days Off yellowkey (back on 4/30/2026)
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1080 Built: 1930 Tax: $410 (2025)Community: Showalter ParkSingle Family
Taxes:$410
Remarks: Under contract-accepting backup offers. Calling all buyers, builders, and investors, this is a rare opportunity to secure land with no HOA in the heart of Downtown Winter Garden. Located within the highly sought after Golf Cart District, just 0.5 miles from the iconic Plant Street Market, seconds from the West Orange Trail, and with convenient access to the Florida's Turnpike, this spacious quarter acre lot offers the ultimate combination of freedom, location, and connectivity. Set on a private street, this property is the perfect canvas to build your custom dream home without restrictive guidelines or additional monthly fees. With an existing structure already on site, electricity, water, and essential utilities are already in place, making the building process significantly easier, faster, and more cost effective. Whether you envision a modern custom estate, a charming bungalow, or an investment opportunity, the flexibility here is unmatched. Enjoy the ability to walk, bike, or golf cart to everything downtown has to offer, while being positioned in an area experiencing exciting growth with new dining, retail, and commercial development continuing to expand throughout Winter Garden. Opportunities like this, a no HOA quarter acre lot in the Golf Cart District with prime access and growth around it, rarely come available. This is your chance to build exactly what you have been dreaming of in one of Central Florida’s most desirable and rapidly evolving communities.
Listing is courtesy of: GLOBAL FLORIDA REALTY (407-380-3030)
Listing Agent: Lauren Bouchard (352-978-6837)
16105 WATER SPRING BLVD, WINTER GARDEN, FL 34787
$499,000210 Days on yellowkey MLS ID: O6348822
REDUCED by $20,000 (3.9%) on 04/16/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2042 Built: 2020Monthly Fee: $103 Tax: $4,770 (2024)Community: Storey GroveSingle Family
Taxes:$4,770
Elementary School: Water Spring Elementary
Remarks: Perfect for buyers seeking convenience, accessibility, and a family-friendly setting—just steps from the elementary school!! Discover this well-maintained 4-bedroom, 3-bath home located in the highly desirable Storey Grove community in Winter Garden. This property offers 2,042 sq ft of bright and functional living space/ Total area :4,704 SqFt , featuring an open-concept layout that seamlessly connects the kitchen and main living areas—ideal for everyday living and entertaining. The spacious primary suite includes a private bathroom and ample storage, while the additional bedrooms provide flexibility for guests, a home office, or growing families. Conveniently situated just steps from the elementary school, this home is perfect for those seeking accessibility and ease in their daily routine. Its location also provides quick access to main roads, shopping, dining, and Disney World, making commuting and errands simple and efficient. Enjoy outdoor living with a private patio, plus access to resort-style community amenities including a pool, fitness center, clubhouse, playgrounds, and dog parks. This property comes with solar panels, providing energy efficiency and savings.. Community parking regulations help maintain a clean and organized neighborhood environment, with guest parking available nearby. Seller is motivated and open to concessions. Schedule your private showing today. Property have solar Panels that will be trasferable to buyers.
Listing is courtesy of: URBAN-O REAL ESTATE SOLUTION (407-822-1063)
Listing Agent: Yesenia Barrios (321-276-1977)
1670 E SPRING RIDGE CIR, WINTER GARDEN, FL 34787
$425,0006 Days on yellowkey MLS ID: O6403033
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1699 Built: 1995Monthly Fee: $50 Tax: $1,352 (2025)Community: Crown Point Springs Ut 2Single Family
Taxes:$1,352
High School: Ocoee High
Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bath home in the highly desirable Spring Ridge area of Winter Garden. Offering 1,699 square feet of thoughtfully designed living space, this move-in ready property combines comfort, charm, and major updates—including a NEW ROOF and A/C installed in 2020 for added peace of mind. Situated on an oversized quarter-acre lot, the home features standout curb appeal, mature landscaping, and a spacious fenced backyard with endless possibilities—whether you envision a pool, garden, play area, or the ultimate entertaining space. Inside, you’ll find a bright and inviting floor plan filled with natural light and comfortable living areas designed for both everyday living and hosting guests. The main living space is centered around a beautiful masonry fireplace, creating the perfect setting for cozy nights and memorable gatherings. The private primary suite offers a walk-in closet and ensuite bath with soaking tub, providing a relaxing retreat at the end of the day. Secondary bedrooms are generously sized and flexible for guests, family, or a home office setup. Located just minutes from top-rated schools, shopping, dining, parks, and major roadways, this is an incredible opportunity to own a well-cared-for home in one of Winter Garden’s most sought-after communities. Homes with this lot size, condition, and location don’t come around often—schedule your private showing today.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Milton James (407-572-4458)
2281 OAKINGTON ST, WINTER GARDEN, FL 34787
$475,00011 Days on yellowkey MLS ID: S5148475
REDUCED by $20,000 (4.0%) on 04/29/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1628 Built: 2003Monthly Fee: $240 Tax: $5,033 (2025)Community: Stoneybrook West 47/78Single Family
Taxes:$5,033
Remarks: Move-in ready home located in the highly desirable guard-gated community of Stoneybrook West. This well-maintained property offers a bright and open layout with a functional split-bedroom floor plan designed for comfortable everyday living. The spacious primary suite features a walk-in closet, dual vanities, soaking tub, separate shower, A flexible bonus area just off the suite can easily serve as a home office, nursery, or additional bedroom. The kitchen provides ample storage and flows seamlessly into the main living space, making it ideal for both daily use and entertaining. The family room is highlighted by a cozy fireplace, adding warmth and charm. Enjoy the fully screened backyard with plenty of room to relax or entertain outdoors. Stoneybrook West residents have access to resort-style amenities, including lake access, multiple sports courts, a community pool, playground, fitness center, and an active Town Centre. Conveniently located near shopping, dining, and major highways, this home offers both lifestyle and location.
Listing is courtesy of: MULTI CHOICE REALTY LLC (352-404-6542)
Listing Agent: Huizi Li (407-353-1043)
1419 HUNTERMAN LN, WINTER GARDEN, FL 34787
$479,90053 Days on yellowkey MLS ID: O6390064
1 Days Off yellowkey (back on 3/20/2026)
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 2840 Built: 2005Monthly Fee: $42 Tax: $7,786 (2025)Community: Chapin Station ASingle Family
Taxes:$7,786
Elementary School: Maxey Elem
Remarks: Under contract-accepting backup offers. This impressive 5-bedroom, 3.5-bathroom residence is situated on a sprawling large corner lot, offering both privacy and abundant outdoor space. The interior is defined by high ceilings and an array of large windows that flood the home with natural light, creating an airy and ambiance. Designed for maximum comfort and privacy, the layout features a primary master suite along with two additional bedrooms boasting their own en suite bathrooms, making it an ideal floor plan for multi-generational living or hosting guests. With its generous proportions and premium lot positioning, this home represents a rare opportunity for those seeking space, light, and a versatile, high-end configuration.
Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)
Listing Agent: Robert Salmons (888-216-6364)
15187 HARROWGATE WAY, WINTER GARDEN, FL 34787
$450,00018 Days on yellowkey MLS ID: TB8497081
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1296 Built: 2003Monthly Fee: $46 Tax: $5,808 (2025)Community: Stone CrkSingle Family
Taxes:$5,808
Remarks: Location! Location! Welcome to this wel maintained 3 beds 2 bath single family home located in the desirable community of Stone Creek in Winter Garden. This home offers a spacious living room, dining area, spacious master bedroom with double sink and walking closet, 2 extra bedrooms and sharing bath, 2 car garage, screened porch and generous fenced back yard. This property is convenient located near shops, restaurants, and the highly rated Elementary School is located inside the community with walking distance. Also, near Winter Garden village Mall, Stonybrook West Golf Club, Tucker Ranch Wellness Park (in construction) And easy acces to the Highway and Airport.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Maria Howard (410-422-3518)
16149 WIND VIEW LN, WINTER GARDEN, FL 34787
$498,00052 Days on yellowkey MLS ID: O6389892
REDUCED by $7,000 (1.4%) on 04/15/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2036 Built: 2016Monthly Fee: $332 Tax: $4,472 (2025)Community: Waterleigh Ph 1BSingle Family
Taxes:$4,472
Remarks: Welcome home to one of the most popular DR Horton floor plans- the Cordale! With a first floor primary suite, spacious open floor plan downstairs, and additional living space upstairs, it is easy to see how the functionality of this home will make it a great fit for you. This home has had 1 owner who has meticulously cared for the home as will be evident immediately upon entering. The open concept living space greets you with the kitchen, dining space, and living room. Lined with windows and recessed lighting, this space feels bright and welcoming. Stainless steel appliances, granite countertops, and ample counterspace equip the kitchen. The downstairs laundry room is tucked away in the front of the home to keep tending to that chore quiet. The primary suite is nestled in the back of the home for privacy and features and en suite bathroom. A walk-in shower, dual vanity, and walk-in closet make this room fit for luxury and comfort. An elongated drop zone leads you to the 2-car garage and has granite countertops and cabinetry in the same colors as in the kitchen for continuity of the downstairs space. The remaining 2 bedrooms are located upstairs where a loft also provides these rooms with another living space. They also share a bathroom with a shower/bathtub combination. The fun continues out back where you'll find a covered brick-paved patio. Relish in the view of not having any rear neighbors, admire the rarity of having a corner lot, and indulge in the unique green space view out of the front of the home. The Waterleigh community is known for its vast array of resort-style amenities include community pools, playgrounds, fitness centers, sports courts, walking trails, dog parks, and more! Primely located in Horizon West, this home is ready for its new owners to make memories here for years to come. Inquire today to make this gem your own! ***NEW HVAC INDOOR BLOWER UNIT, NEW HVAC OUTDOOR CAPACITOR UNIT***
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Jacquelyn Voigt (941-356-3956)
16716 WINGSPREAD LOOP, WINTER GARDEN, FL 34787
$495,00025 Days on yellowkey MLS ID: O6397108
1 Days Off yellowkey (back on 4/24/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1676 Built: 2019Monthly Fee: $127 Tax: $5,006 (2025)Community: Hawksmoor-Ph 1Single Family
Taxes:$5,006
Remarks: Under contract-accepting backup offers. Welcome to 16716 Wingspread Loop, a beautifully maintained single-story home in the highly sought-after Hawksmoor community of Winter Garden. Built in 2019 and cared for by its original owner, this 3-bedroom, 2-bath residence is move-in ready with thoughtful upgrades throughout. The open layout creates an easy flow between the kitchen, dining, and living areas. The kitchen features warm honey-toned cabinetry, granite countertops, and generous storage. The spacious primary suite serves as a private retreat with a large bedroom, walk-in closet, and an en-suite bath with quartz countertops. Additional highlights include built-in cabinetry in the laundry room, with the washer and dryer conveying for added convenience. Enjoy Florida living outdoors on the private patio, perfect for relaxing or hosting friends. The two-car garage includes a durable epoxy-coated floor, and the paved driveway enhances the home’s curb appeal. All kitchen and laundry appliances are included. Located along Avalon Road, this home places you just minutes from Hamlin Town Center, Flamingo Crossings, Walt Disney World, FL-429, Orange County National Golf Center, Clermont, Windermere, and top-rated Orange County schools. Residents of Hawksmoor enjoy a variety of resort-style amenities, including a clubhouse with rentable event space, fitness center, pool and splash pad, outdoor summer kitchen and grill, yoga lawn, shaded playground, dog park, and scenic walking paths. Schedule your private showing today and experience everything this Winter Garden home has to offer. Transferable lifetime termite contract from Massey available.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
837 GRANDE REGAL PT, WINTER GARDEN, FL 34787
$479,00011 Days on yellowkey MLS ID: O6400571
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1874 Built: 2002Monthly Fee: $60 Tax: $1,662 (2025)Community: Regal Pointe Ph 02 47/133Single Family
Taxes:$1,662
Remarks: Nestled in the highly sought after area of Winter Garden, this hidden gem presents the perfect blend of comfort, convenience, and charm. This well maintained home features three spacious bedrooms and two bathrooms, along with both a welcoming living room and a separate family room, ideal for entertaining or relaxing with loved ones. Centrally located, the property is just minutes from the hospital, shopping, dining, and all that Winter Garden has to showcase. Practically turnkey, the home boasts major updates including a 2019 roof, 2022 HVAC system, and a 2022 water heater, providing peace of mind for years to come. Step outside to your own private oasis, where a beautifully maintained yard is filled with a variety of fruit trees and plants, including avocado, banana, pigeon peas, lemon, pineapple, ginger, soursop, and much more, perfect for enjoying fresh homegrown produce. Do not miss the opportunity to own this unique and inviting home in a prime location!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Herna Quero (321-305-0916)
328 BAYSIDE AVE, WINTER GARDEN, FL 34787
$445,00017 Days on yellowkey MLS ID: O6396654
1 Days Off yellowkey (back on 4/23/2026)
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
Remarks: Under contract-accepting backup offers. Welcome to easy Florida living in this charming 3-bedroom, 2-bath ranch-style home, perfectly positioned on a spacious corner lot in one of Winter Garden’s most desirable areas. With its single-story layout and inviting curb appeal, this home offers both comfort and convenience in a relaxed, open setting. Step inside to discover a bright and functional floor plan designed for everyday living and effortless entertaining. The generous living spaces flow seamlessly, while ample natural light enhances the home’s warm and welcoming feel. The split-bedroom design provides privacy, with a well-appointed primary suite and comfortable secondary bedrooms. Outside, the oversized corner lot offers endless possibilities—plenty of room for outdoor gatherings, gardening, or simply enjoying the Florida sunshine. Located well within the golf cart district, you’re just a short ride from the charm and energy of historic downtown Winter Garden. Enjoy easy access to local shops, dining, community events, and the popular weekly farmers market, all just minutes from your doorstep. This is a rare opportunity to own a beautifully situated home that combines classic ranch-style living with an unbeatable location. Call Today!
Listing is courtesy of: SOUTHERN HERITAGE REALTY, INC (407-877-6928)
Listing Agent: Jim Kernohan (407-450-3861)
16856 HYPATIA ALY, WINTER GARDEN, FL 34787
$459,99960 Days on yellowkey MLS ID: O6387941
0 Days Off yellowkey (back on 4/23/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1705 Built: 2019Monthly Fee: $250 Tax: $6,769 (2024)Community: Waterleigh Ph 3ASingle Family
Taxes:$6,769
Remarks: Under contract-accepting backup offers. This charming one story 3 bedroom 2 bath floor features a beautiful kitchen that opens to a spacious family room. You will love cooking in the well-appointed kitchen with great prep space, stainless steel appliances, walk in pantry and a large island that is great for easy entertaining. Brick Pavers are on your front driveway, front porch and covered lanai. Waterleigh is located in Winter Garden/Horizons West and features 2 beautiful clubhouses with resort style pools, miniature putting golf course, 2 fitness centers, and tennis courts. Come out and our beautiful decorated models and view the community that is a “must see” in Winter Garden.
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Luis Gonzalez (305-924-1119)
13837 LANYARD WAY, WINTER GARDEN, FL 34787
$490,00056 Days on yellowkey MLS ID: O6388993
REDUCED by $5,000 (1.0%) on 04/22/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1994 Built: 2023Monthly Fee: $225 Tax: $7,647 (2024)Community: Encore/Ovation Ph 3Spa: NoSingle Family
Taxes:$7,647
Remarks: Welcome to 13837 Lanyard Way, a home that exudes elegance and comfort. The kitchen is a chef's dream with all stainless steel appliances and a functional kitchen island. A walk-in pantry provides ample storage for all your culinary needs. The primary bedroom is a sanctuary with a spacious walk-in closet. The primary bathroom is a haven of relaxation with double sinks. Outside, a storage shed provides additional space for your belongings. Enjoy outdoor living with a covered patio and a fenced-in backyard. This home is a perfect blend of style and functionality. Don't miss out on this gem! Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
2621 SHIREHALL LN, WINTER GARDEN, FL 34787
$475,00059 Days on yellowkey MLS ID: O6386585
REDUCED by $25,000 (5.0%) on 04/17/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1960 Built: 2003Monthly Fee: $243 Tax: $3,181 (2024)Community: Stoneybrook West Ut 04 48 48Spa: NoSingle Family
Taxes:$3,181
Remarks: PRICE IMPROVEMENT. Welcome to this beautifully maintained 3-bedroom, 2-bath home nestled in a 24 hour guard-gated golf community offering resort-style living. Enjoy tranquil mornings from the screened lanai overlooking a serene pond, creating the perfect setting for relaxation or entertaining. The thoughtfully designed floor plan features spacious living areas, abundant natural light, and comfortable bedrooms ideal for both everyday living and guests. The spacious primary suite has a beautiful water view with ensuite having dual sinks, garden tub and walk in shower. This spilt bedroom plan adds to the convenience of privacy, noise reduction and efficient space management. The open Kitchen overlooks the family room and has a breakfast area with center island and granite countertops. The interior has just been painted first of March, New water heater 4/2026. Residents enjoy access to an impressive array of amenities, including a championship golf course, clubhouse, resort-style pool, fitness center, tennis and pickleball courts, walking and biking trails, and an active social calendar. Conveniently located near shopping, dining, and entertainment, this home offers the perfect blend of comfort, security, and lifestyle. Please call for your showing today.
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Barbara Waltman (407-616-2790)
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