Location: Winter Garden , 34787
Do Not Show Listings
13780 FRESH IVY ST, WINTER GARDEN, FL 34787
$865,00048 Days on yellowkey MLS ID: O6403387
REDUCED by $30,000 (3.4%) on 06/06/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2862 Built: 2025Monthly Fee: $642 Tax: $2,578 (2025)Community: Del Webb Oasis Ph 3Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,578
Elementary School: Water Spring Elementary
High School: Horizon High School
Tax Year: 2025
Middle School: Water Spring Middle
Remarks: Welcome to this elegant and NEARLY NEW 4-bedroom, 3-bath home in the highly sought-after Del Webb Oasis of Winter Garden, a GUARD-GATED 55+ community where luxury, comfort, and lifestyle come together beautifully. Built in 2025 and offering over 2,800 SQUARE FEET, this residence features the LARGEST FLOOR PLAN in the community and is perfectly situated on one of the MOST EXPANSIVE LOTS providing both space and privacy. From the moment you arrive, the home impresses with its REFINED CURB APPEAL and spacious 2-car garage with an additional TANDEM BAY—ideal for a golf cart or extra storage. Inside, you’ll find a bright, open-concept design enhanced by LUXURY VINYL PLANK FLOORING that flows seamlessly through the Living Room, Dining area, and Kitchen. NATURAL LIGHT pours into the main living spaces through large windows with ELECTRIC BLINDS and dramatic corner sliding glass doors, creating a seamless transition to the outdoor living area. The Kitchen is a TRUE SHOWPIECE, thoughtfully designed with white cabinetry, stone countertops, a stylish tile backsplash, stainless steel appliances, BUILT-IN OVENS, a gas cooktop, a closet pantry, and an oversized breakfast bar that anchors the space beautifully. The Primary Suite, located on the main floor, offers a private retreat with ABUNDANT NATURAL LIGHT and serene backyard views. It features a CUSTOM-DESIGNED WALK-IN CLOSET (2026) and a SPA-INSPIRED EN SUITE BATH with dual sinks, a dedicated makeup area, a walk-in shower with built-in seating, and a private water closet. Also on the main level, you’ll find a secondary bedroom and full bath, along with a FLEXIBLE OFFICE SPACE behind glass French doors that can easily serve as a fourth bedroom. A Mudroom and well-appointed Laundry Room—complete with washer, dryer, cabinetry, and COUNTER SPACE—add everyday convenience. Upstairs, a GENEROUS LOFT AREA offers incredible versatility, currently enhanced with a CUSTOM COFFEE BAR (2025) and large enough to accommodate additional living, entertaining, or even a future bedroom while still maintaining open loft space. An ADDITIONAL BEDROOM AND FULL BATH upstairs provide the perfect setup for guests. Step outside to your EXTENDED COVERED PAVER PATIO, complete with a SUMMER KITCHEN (2025) and set beneath an oversized screened lanai, all enhanced by CUSTOM OUTDOOR LIGHTING (2025). This home has been further enhanced with thoughtful upgrades, including a WATER FILTRATION AND SOFTENER SYSTEM (2026), FENCED BACKYARD (2025), and expanded outdoor living features that elevate both comfort and functionality. Residents of Del Webb Oasis enjoy RESORT-STYLE AMENITIES, including a clubhouse, sparkling pool, fitness center, tennis courts, and social activities, along with included cable and internet, fostering an active and connected lifestyle. IDEALLY LOCATED in Winter Garden, you’re just minutes from the charm of HISTORIC DOWNTOWN WINTER GARDEN, known for its boutique shopping, dining, and weekly farmers market. Enjoy OUTDOOR RECREATION along the West Orange Trail, or take a short drive to WORLD-CLASS ATTRACTIONS like Walt Disney World Resort. Convenient access to major roadways makes exploring all that Central Florida has to offer effortless. This exceptional home offers a RARE OPPORTUNITY to enjoy elevated, low-maintenance living in one of Winter Garden’s premier active adult communities—where every detail has been THOUGHTFULLY DESIGNED for both luxury and ease. Now is the time—don't miss your chance to call this home!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
15026 SUMMER HARVEST ST, WINTER GARDEN, FL 34787
$669,990146 Days on yellowkey MLS ID: S5142710
REDUCED by $22,000 (3.2%) on 06/19/2026
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2908 Built: 2024Monthly Fee: $202 Tax: $9,669 (2025)Community: Harvest At OvationSingle Family
Taxes:$9,669
Elementary School: Whispering Oak Elem
Middle School: Horizon West Middle School
Remarks: PRICE IMPROVEMENT! Exceptional opportunity in Winter Garden. This 2024 home offers 5 bedrooms, 4.5 bathrooms, and a private suite with a separate entrance, bedroom, bathroom, and kitchenette. With over $60,000 in upgrades already completed, this property delivers value from day one. Ideally located just minutes from Disney, Flamingo Crossings, Hamlin Town Center, shopping, dining, entertainment, hospitals, and top-rated schools. The open-concept floor plan features high ceilings, a remodeled kitchen, porcelain tile flooring on the first floor, upgraded second-floor flooring, wood stairs, upgraded paint, paver driveway and patio, epoxy garage flooring, and numerous additional improvements throughout the home. The private suite provides excellent flexibility for multigenerational living, guests, or additional private living space. A rare opportunity to purchase a nearly new home in a prime Winter Garden location with major upgrades already completed. Buyer and buyer’s agent to verify all information, including room sizes, HOA, school zoning, rental restrictions, lease details, and all property information. Proof of funds or pre-approval required prior to showing.
Listing is courtesy of: AROD PARTNERS REALTY (407-627-7621)
Listing Agent: Keyla Chirinos Sivira (786-380-5541)
9103 MORGANA CT, WINTER GARDEN, FL 34787
$1,630,90034 Days on yellowkey MLS ID: O6409652
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4376 Built: 2022Monthly Fee: $423 Tax: $15,919 (2025)Community: Avalon CoveSingle Family
Taxes:$15,919
Elementary School: None
High School: None
Middle School: None
Remarks: Nestled within one of Central Florida's most exclusive neighborhoods this stunning home offers the perfect blend of luxury, comfort, and effortless entertaining. Located on a quiet cul-de-sac street boasting 5 bedrooms, 4.5 baths, a large loft and open floor plan this home is designed for everyday living and seamless hosting! Step outside to your private resort style salt water pool and enjoy nightly views of the Disney fireworks lighting up the sky! The upgraded "picture frame" pool screen design offers an uninterrupted view of the serene pond and the diverse wildlife that visits it! On the main level you will find the PRIMARY SUITE COMPLETE WITH A LUXURIOUS SPA LIKE BATH AND HUGE walk-in closet, a guest bedroom with its own full bath, the glass enclosed wine room and a convenient half bath for guests. The GOURNET KITCHEN flows to the expansive great room where 4 large sliders can open to the covered patio for the "outside inside" living!! Upstairs, in addition to the large loft are 2 bedrooms that share a full bath and another private en-suite bedroom. Recent upgrades include beams on the main level ceiling, beautiful built-in wall unit in the loft, outdoor kitchen and outdoor lighting. Located just minutes from Walt Disney World, premier shopping, dining, and everyday conveniences, and approximately 30 minutes to Orlando International Airport, this beautiful home is perfect for that unbeatable central Florida lifestyle!
Listing is courtesy of: HAMMOND REALTY GROUP LLC (407-468-0074)
Listing Agent: Lesa Dolan (407-925-5786)
14610 SETON CREEK BLVD, WINTER GARDEN, FL 34787
$488,00027 Days on yellowkey MLS ID: GC540630
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1916 Built: 2016Monthly Fee: $164 Tax: $5,965 (2025)Community: Watermark Ph 1BSingle Family
Taxes:$5,965
Remarks: Welcome to this beautifully maintained 3-bedroom, 2.5-bath home located in the highly desirable Watermark community in Winter Garden! This home features a bright open-concept floor plan where the kitchen, dining, and living areas seamlessly flow together — perfect for entertaining and everyday living. Upstairs, you’ll find all three bedrooms, two full bathrooms, a convenient upstairs laundry room, and an additional flex space ideal for a playroom, office space, media room, or second family room. The spacious primary suite offers privacy, while the two secondary bedrooms share access to a charming private balcony overlooking the neighborhood. A downstairs half bath adds convenience for guests. Additional features include a 2-car garage, energy-efficient solar panels, and thoughtfully designed living spaces throughout. Enjoy an unbeatable location with Starbucks, Walgreens, restaurants, shopping, and everyday conveniences all in close proximity. For Disney lovers, Magic Kingdom is approximately 9 miles away and Disney Springs is about 12 miles away, making this an ideal primary residence, vacation home, or investment opportunity. Residents of Watermark enjoy resort-style amenities including a community pool, tennis courts, clubhouse, playground, fitness center, and scenic walking trails. This home offers the perfect combination of location, lifestyle, and modern Florida living!
Listing is courtesy of: CROSS KEYS REALTY, INC. (352-505-5049)
Listing Agent: Morgan Coleman (352-222-9093)
14075 LOCHEND WAY, WINTER GARDEN, FL 34787
$515,000134 Days on yellowkey MLS ID: O6380897
REDUCED by $10,000 (1.9%) on 06/19/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2197 Built: 2024Monthly Fee: $133 Tax: $1,835 (2024)Community: Ovation/WesthavenTownhouse
Taxes:$1,835
Tax Year: 2024
Remarks: Gorgeous, pristine and clean, four-bedroom, three-bath, like-new townhome, is approximately 20 minutes to the Disney area and approximately 35 minutes to Universal and on a prime corner lot in the desirable West Haven Ovation community of Winter Garden. Built by Toll Brothers, this nearly new townhome offers an opportunity to move in now so why wait to build! This two-story townhome features an open-concept floor plan filled with abundant natural light. The kitchen is a showstopper, boasting quartz countertops, wood cabinetry, stainless steel appliances, ample lighting, an extended island with a breakfast bar, a large walk-in pantry and a separate dining area. The spacious family room flows seamlessly from the kitchen and dining areas, making it ideal for entertaining. The first floor includes a guest bedroom with a large closet and a full bath with tub/shower, offering flexibility for a home office, playroom or workout space. Upstairs, you’ll find three additional bedrooms, including the oversized primary suite, complete with a spacious walk-in closet and a private en-suite bath featuring dual vanities. The second floor also includes a large walk-in laundry room, with washer and dryer included. Enjoy the convenience of a rear-facing two-car garage with opener and a private courtyard, ideal for relaxing in the sun. There is an enclosed walkway from the garage to the home. Residents of West Haven Ovation enjoy resort-style amenities, including a community clubhouse and pool, playground, and sidewalks for recreation, biking or jogging. Near Horizon West Town Center, with easy access to Interstate 4 and the 429 Expressway, and close to shopping, dining, highly rated schools and an easy commute to Disney area theme parks. Call today to schedule your private tour. This beautiful home could be yours!
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-581-7888)
Listing Agent: Wendy Fischer (407-620-0713)
9107 GRAND ISLAND WAY, WINTER GARDEN, FL 34787
$499,90099 Days on yellowkey MLS ID: O6391117
4 Days Off yellowkey (back on 6/19/2026)
REDUCED by $5,100 (1.0%) on 05/04/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2082 Built: 2017Monthly Fee: $159 Tax: $7,996 (2025)Community: Watermark Ph 2CSingle Family
Taxes:$7,996
Elementary School: Panther Lake Elementary
Middle School: Hamlin Middle
Remarks: Welcome to 9107 Grand Island Way, a beautiful Corner Lot Home in the heart of Horizon West’s Watermark community! This home is the perfectly balance of comfort, style, and convenience, designed for both everyday living and entertaining. Upon entering the front door, you will see your updated, modern kitchen with granite countertops, modern 42" cabinets and modern pendant lights overlooking your spacious living room. You will space for a nice dining room table to entertain as well as a half bathroom and the entrance to the 2 car garage! Upon walking up the modern staircase, you will find a very nice spaced loft/entertainment room, to where you can have your private second living room, office or movie theater room! The primary bedroom provides a relaxing and spacious space with a nice sized primary bathroom and walk in closet, while the additional bedrooms offer flexibility for family, guests, or a home office. As this is a corner lot, there home is filled with natural light. flowing seamlessly into the kitchen and dining space. One of the most unique aspects of this property is its prime corner location directly across from the vibrant Horizon West Retail Center, placing you just steps from such stores like Starbucks, New York Beer Project, 7-11 and Walgreens and more! Enjoy the rare ability to walk or bike to dining, entertainment, and local hotspots while still enjoying the privacy of a residential neighborhood. Residents of Summerlake enjoy resort-style amenities including a community pool, clubhouse, fitness center, dog parks, playgrounds and more! With easy access to Interstate 429, Hamlin Town Center, top-rated schools, Orange County National Golf Center and Walt Disney World just minutes away, this home offers the perfect balance of lifestyle and location in one of Winter Garden’s most sought-after communities conveniently located in the middle of everything!
Listing is courtesy of: FHG REALTY, LLC (407-505-7600)
Listing Agent: Jeff Inman (407-505-7600)
14501 GROVE RESORT AVE #1742, WINTER GARDEN, FL 34787
$209,900272 Days on yellowkey MLS ID: O6346817
0 Days Off yellowkey (back on 6/19/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1396 Built: 2016Monthly Fee: $997 Tax: $6,945 (2024)Community: Grove Resort And SpaCondo
Taxes:$6,945
Remarks: Under contract-accepting backup offers. Here’s your chance to own a stunning 3-bedroom, 2-bath condominium in The Grove Resort & Water Park, one of Orlando’s most sought-after vacation destinations. Located just 5 minutes from Walt Disney World, this fully furnished, move-in-ready residence combines luxury living with incredible investment potential. Step inside to find a spacious, light-filled layout that’s perfect for relaxing or entertaining. The condo features contemporary décor, high-end finishes, and a sleek, modern kitchen complete with stainless steel appliances, quartz countertops, and plenty of storage. A private screened balcony extends your living space outdoors, while the in-unit washer and dryer add convenience for longer stays. The Grove Resort is packed with amenities designed to impress every guest. Spend the day at Surfari Water Park with its FlowRider® surf simulator, lazy river, waterslides, and zero-entry pools. Take time to unwind in the multiple pools and hot tubs, book a treatment at the on-site spa, or keep active in the 24-hour fitness center. Dining is effortless with several restaurants and bars on property, including Valencia Restaurant and Longboard Bar & Grill. Families will love Flip Flop’s Family Fun Center, while outdoor enthusiasts can kayak, fish, or paddle boat on Lake Austin. A complimentary shuttle makes it easy to visit Disney, Universal, and SeaWorld. Conveniently located in Winter Garden, The Grove is also close to golf, shopping, dining, and major highways. Owners enjoy flexibility — use the condo as your personal getaway or take advantage of the professional hotel rental program to generate income when you’re not there. With its unbeatable location, world-class amenities, and turnkey ownership, this condo offers the perfect mix of a private retreat and a smart investment. Don’t miss the chance to own a piece of Orlando paradise. Contact us today to schedule your private tour!
Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)
Listing Agent: Brooke Cangro (407-758-6699)
12390 CLEAR SAPPHIRE, WINTER GARDEN, FL 34787
$764,99085 Days on yellowkey MLS ID: O6394850
1 Days Off yellowkey (back on 6/19/2026)
REDUCED by $5,000 (0.6%) on 06/16/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2552 Built: 2026Monthly Fee: $96Community: Osprey RanchSingle Family
Taxes:$0
Tax Year: 2026
Remarks: Under contract-accepting backup offers. Under Construction. .
Listing is courtesy of: K HOVNANIAN FLORIDA REALTY (321-263-2601)
Listing Agent: Richard Selikoff (201-741-7242)
9606 WOODCRANE DR, WINTER GARDEN, FL 34787
$525,00032 Days on yellowkey MLS ID: O6410113
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2101 Built: 2017Monthly Fee: $164 Tax: $5,079 (2025)Community: Watermark Ph 2BSingle Family
Taxes:$5,079
Remarks: Prime corner lot home in the highly sought-after Horizon West community of Watermark in Winter Garden with no front neighbors and peaceful water views. Ideally located just a short walk to the community amenity center and The Mark shopping center featuring Starbucks, New York Beer Project, 7-Eleven, Walgreens, dining, entertainment, and more. Enjoy nightly Disney fireworks views right from the front porch, living room or loft sofa. Conveniently located near State Road 429, Hamlin Town Center, top-rated schools, Orange County National Golf Center, and Walt Disney World. This home offers the perfect blend of lifestyle, convenience, and location in the heart of Horizon West.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
1142 DUNBROOKE ST, WINTER GARDEN, FL 34787
$515,0005 Days on yellowkey MLS ID: O6417527
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2068 Built: 2005Monthly Fee: $53 Tax: $4,251 (2025)Community: Chapin StationSingle Family
Taxes:$4,251
Elementary School: Maxey Elem
High School: Ocoee High
Middle School: Lakeview Middle
Remarks: Virtually staged. Welcome to Chapin Station! On an almost quarter-acre lot, this four-bedroom, three-bath home offers a light and spacious split-bedroom open floor plan designed for comfort and functionality. Go inside to find soaring ceilings and an open layout featuring a formal dining room, a large family room and a bright breakfast nook overlooking the kitchen. Double-pane windows provide added energy efficiency throughout the home. The living areas seamlessly connect to the expansive covered rear patio and private backyard, creating the ideal setting for everyday living and entertaining. The thoughtfully designed split floor plan provides privacy for all. The primary suite features vaulted ceilings, dual walk-in closets and an en-suite bath with double vanities, a garden tub and a separate shower. On the opposite side of the home, two secondary bedrooms share a full bath, while a separate guest suite and additional bath offer ideal accommodations for visitors or multigenerational living. The oversized backyard provides ample space to create your dream outdoor oasis, whether you envision a pool, play area, garden or outdoor entertainment space. The large covered patio is ideal for grilling, relaxing, and gathering with family and friends. In the sought-after Chapin Station community, this well-maintained home offers easy access to the West Orange Trail, historic downtown Winter Garden, major highways, hospitals, shopping, dining and Central Florida's world-famous theme parks.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)
Listing Agent: Naresh Mistry (321-356-7882)
1610 BEULAH RD, WINTER GARDEN, FL 34787
$450,0005 Days on yellowkey MLS ID: O6418153
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2210 Built: 1998Monthly Fee: $44 Tax: $2,189 (2025)Community: Orange CoveSingle Family
Taxes:$2,189
Remarks: Welcome to 1610 Beulah Road, a custom built home in one of Winter Garden's most convenient locations. Situated directly across from West Orange High School, this exceptional property offers the perfect blend of privacy, tranquility, and accessibility. Just five minutes from Historic Downtown Winter Garden and Plant Street Market, you'll enjoy easy access to award winning dining, boutique shopping, the popular Farmers Market, Crooked Can Brewing Company, and countless community events throughout the year. Designed with comfort and quality in mind, this custom residence is nestled against protected wooded wetlands, creating a peaceful backdrop rarely found so close to town. Relax and unwind from the screened rear patio while taking in the serene views and natural beauty of the private backyard setting. With no rear neighbors and lush conservation views, this home offers a quiet retreat that feels worlds away. Commuters will appreciate the easy access to State Road 429 and the Florida Turnpike, providing convenient connections to Downtown Orlando, Lake County, and major employment centers throughout Central Florida. Whether you're searching for a home near Downtown Winter Garden, top rated schools, or a property with privacy and scenic views, 1610 Beulah Road delivers an unbeatable combination of location, craftsmanship, and lifestyle. Experience the best of Winter Garden living with the perfect balance of convenience and natural beauty.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Matthew Mckee (407-948-0658)
15121 EVERGREEN OAK LOOP, WINTER GARDEN, FL 34787
$824,90012 Days on yellowkey MLS ID: O6416065
REDUCED by $50,000 (5.7%) on 06/19/2026
Bed: 6 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4042 Built: 2016Monthly Fee: $180 Tax: $552 (2024)Community: Signature Lakes Ph 3B-4Single Family
Taxes:$552
Elementary School: Independence Elementary
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: Welcome to 15121 Evergreen Oak Loop, a stunning 6-bedroom, 4-bathroom home offering over 4,200 square feet of thoughtfully designed living space in one of Winter Garden's most desirable communities. Situated on an oversized homesite with no rear neighbors, this exceptional property combines space, comfort, and privacy with beautiful conservation views and breathtaking Florida sunsets. The heart of the home is the expansive gourmet kitchen featuring stainless steel appliances, a large center island, abundant cabinetry, and an open-concept design that flows seamlessly into the main living areas—perfect for entertaining family and friends. Flexible living spaces include a first-floor bedroom and full bath, ideal for guests, a home office, or multigenerational living. Upstairs, you'll find a spacious theater room complete with reclining theater seating, projector, screen, and surround sound system—all included with the home—creating the ultimate space for movie nights, sporting events, and gaming. The luxurious primary suite serves as a private retreat with a spa-inspired bath, dual vanities, soaking tub, separate shower, and oversized walk-in closet. Step outside to enjoy peaceful conservation views from multiple outdoor living spaces, offering a level of privacy rarely found in Horizon West. Whether you're enjoying your morning coffee or winding down in the evening, this home provides the perfect backdrop for Florida living. Location is everything, and this home delivers. Just minutes away is the newly opened Horizon West Regional Park, a 215-acre recreational destination featuring an inclusive playground, walking and biking trails, picnic pavilions, athletic fields, open green space, and recreational facilities. Future phases are planned to bring additional trails, expanded recreational amenities, and nature-focused areas, adding even more value to this already exceptional location. Residents enjoy convenient access to top-rated schools, shopping, dining, major highways, Disney attractions, and everything that makes Horizon West one of Central Florida's most sought-after places to live. Offering an ideal combination of size, functionality, entertainment, and location, this is a rare opportunity to own a truly special home in the heart of Winter Garden.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Adam Jackson (407-572-6252)
13037 SERENE GLADE RD, WINTER GARDEN, FL 34787
$559,9907 Days on yellowkey MLS ID: G5113926
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1836 Built: 2026Monthly Fee: $160Community: Serenade At OvationSingle Family
Remarks: Virtually Staged. Under Construction. Discover the charm of the Brantley Floor Plan, a bungalow perfect for families and entertaining. This plan features 3 bedrooms, 2.5 bathrooms, a loft, and a 2-car garage. The gourmet kitchen boasts top-end designer finishes and flows seamlessly into the living areas, ideal for gatherings. An extra-large corner pantry provides ample storage for bulk purchases, enhancing functionality. Check out the Brantley today and imagine your life in the beautifully designed home!
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
1219 SADDLEBACK DR, WINTER GARDEN, FL 34787
$1,050,00018 Days on yellowkey MLS ID: O6412381
0 Days Off yellowkey (back on 6/18/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2667 Built: 2022Monthly Fee: $215 Tax: $11,474 (2025)Community: Oakland Parkb-1Spa: NoSingle Family
Taxes:$11,474
Elementary School: Tildenville Elem
High School: West Orange High
Remarks: Welcome to what may be the most impeccably maintained and beautifully upgraded home in Oakland Park! This stunning 4-bedroom, 3.5-bath residence showcases designer-inspired finishes throughout, featuring soaring ceilings, modern color palettes, and countless custom enhancements that make it truly one of a kind. Built just four years ago and nestled on a quiet street directly across from green space, this exceptional David Weekley Seaside model offers the perfect blend of elegance, comfort, and convenience. The thoughtfully designed floor plan features a luxurious first-floor owner's retreat complete with a spacious spa-like bath, while the additional bedrooms, study, dining area, and generous living spaces provide room for everyone to spread out and enjoy. No detail has been overlooked. The current owners have invested extensively in premium upgrades, including custom wood trim and accent walls, designer wallpaper, upgraded lighting throughout, custom Zebra window shades, professionally designed closets in the owner's suite, secondary bedroom, and laundry room, plus a water softener, gutters, epoxy-coated garage floors, updated landscaping, and an inviting paver patio. Both the interior and exterior have been freshly painted, creating a truly move-in-ready experience. Step outside to the screened rear porch, where you'll enjoy peaceful mornings, evening breezes, and endless opportunities for birdwatching and outdoor dining. The spacious 3-car garage provides ample storage and functionality for today's lifestyle. Beyond the home itself, Oakland Park offers an award-winning lifestyle unlike any other. This celebrated Parade of Homes community is known for its charming streetscapes, abundant green spaces, waterfront gathering areas, parks, and strong sense of community. Golf-cart-friendly and ideally located just minutes from the West Orange Trail, you'll also enjoy the convenience of walking or riding into vibrant downtown Winter Garden for exceptional dining, shopping, entertainment, and year-round events. This is more than a home—it's a lifestyle defined by luxury, connection, recreation, and the timeless charm of Winter Garden Living.
Listing is courtesy of: CENTRAL FLORIDA PRIME REAL ESTATE LLC (407-404-4041)
Listing Agent: Lynette Piontek (407-222-4310)
121 W MAPLE ST, WINTER GARDEN, FL 34787
$1,725,0006 Days on yellowkey MLS ID: O6417649
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3243 Built: 1999 Tax: $10,572 (2025)Community: G T Smith Sub 2Spa: YesSingle Family
Taxes:$10,572
Remarks: Welcome to 121 West Maple Street…a Downtown Winter Garden one-of-a-kind statement home spanning nearly 5,500 square feet of indoor & outdoor living space. Originally constructed in 1999 and thoughtfully expanded in 2019…yet this special residence has the heart & soul of a time long ago when character, craftsmanship and attention to details mattered. Private Pool & Spa. Poolhouse. Drawing Room & Study. Courtyard with Fountain. Renovated Kitchen & Bathrooms. 10’ Ceilings. Wood Floors. Handmade (USA) Solid Wood Doors. Custom Wood Trim Throughout. Three-Car Garage with Carriage House. Three Fireplaces. Natural Gas. Custom Built Wood Fence with Copper Caps. Located on one of the few remaining brick roads just TWO BLOCKS from Plant Street, this home with spectacular curb appeal is situated on a rare corner double lot with extensive landscaping & beautiful mature trees…including the incredible Southern Live Oak in front that is part of the Winter Garden Heritage Trees project & walking tour. Enjoy historical charm appropriate for the location...yet live without the pains & aches of owning an old historic home. The incredible drawing room & study (2019) was designed by the historical architect for the City of Charleston…twenty-nine windows, extensive trim work & built-ins, historically accurate sconces & lighting and automatic privacy shades. Live the Florida lifestyle outdoors in this incredible outdoor oasis with heated pebble tec saltwater pool & spa. Following a 2023 transformation with a cost of $225,000, the outdoor living space now features a custom poolhouse cabana with a gas fireplace, multiple seating areas, outdoor kitchen with island, built-in grill, burner and refrigerator, retractable screen to astroturf lawn, Trex decking, custom lighting, water features, extended covered lanai and SunBrite outdoor television. (Hayward Natural Gas Pool/Spa Heater - 2025; Hayward Tristar Pool Pump - 2023; Filter Unit - 2020; Salt Cell - 2020). Fantastic & FLEXIBLE floor plan...four bedrooms, three full bathrooms and one half bathroom. Primary suite on main floor. The carriage house above the garage features a separate staircase entrance with private bedroom, bathroom and walk-in closet with built-ins. Stunning kitchen renovation (2021) including custom cabinetry, backsplash, quartz countertops, farm sink, designer lighting, new appliances and an open-concept design that flows effortlessly into the family room. Roof -- July 2019. HVAC -- 2025 (upstairs); 2018 (downstairs - damper system). Tankless Gas Water Heater -- Dec 2015. Garage Epoxy Floor. Whole Home Natural Gas Generator. FULL UPGRADE & SPECIAL FEATURES LIST AVAILABLE. Furnishings and decor (inside & outside), golf cart & custom holiday decorations NEGOTIABLE. Zoned R-2. NO HOA...live without rules & restrictions. You COULD NOT be closer to enjoying the lifestyle of Central Florida's most desirable and growing historic downtown...GOLF CART LIFE, the West Orange Trail, HUGE weekly farmer's market, incredible annual festivals, shopping, dining, art gallery, the Crooked Can Brewery & Plant Street Market, parks & recreation...come JOIN THE FUN! Also conveniently located minutes from the Winter Garden Village shopping center and just minutes from HWY 429 with direct connect to the Turnpike and 408 for an easy commute to anywhere in Central Florida. This is THE ONE you have been waiting for in Downtown Winter Garden...DO NOT MISS your opportunity to own this one-of-a-kind dream home & property!
Listing is courtesy of: TARA MOORE REAL ESTATE (407-738-5588)
Listing Agent: Tara Moore (407-765-3700)
233 SOUTHERN PECAN CIR #101, WINTER GARDEN, FL 34787
$252,90089 Days on yellowkey MLS ID: S5144851
REDUCED by $7,000 (2.7%) on 05/11/2026
Bed: 2 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 966 Built: 2005Monthly Fee: $343 Tax: $2,537 (2024)Community: Southern Pines CondoCondo
Taxes:$2,537
Elementary School: SunRidge Elementary
Middle School: SunRidge Middle
Remarks: Welcome to this beautifully remodeled 2-bedroom, 1-bath condo with an attached garage. Move right into this stunning corner unit. This light-filled home has been thoughtfully updated throughout with fresh paint and brand-new flooring, and modern finishes that create a clean, contemporary feel. Residents enjoy access to an impressive array of resort-style community amenities, including. Swimming pool with a relaxing hot tub spa, fully equipped fitness center, indoor basketball and racquetball court, tennis court, and a convenient car wash area. Whether you're looking for your next home or a great investment opportunity, this beautifully updated condo combines comfort, style, and exceptional amenities in one attractive package. New A/C was installed on June 11, 2026
Listing is courtesy of: HOMESMART (407-476-0451)
Listing Agent: Maria Lloret (407-929-1994)
12566 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787
$592,000103 Days on yellowkey MLS ID: O6389532
REDUCED by $17,900 (2.9%) on 06/15/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2420 Built: 2024Monthly Fee: $96 Tax: $2,162 (2024)Community: Osprey Ranch-Ph 1Single Family
Taxes:$2,162
Remarks: PRICE IMPROVEMENT! PRICED TO SELL, SELLER WILLING TO CONTRIBUTE UP TO $7,500.00 TOWARDS CLOSING COSTS OR BUYER RATE BUY-DOWN! Welcome to 12566 Westhaven Oak Drive in the desireable Osprey Ranch community of Winter Garden. This beautifully designed 4-bedroom, 3-bath home offers the perfect blend of modern comfort and luxury finishes, featuring an open-concept layout ideal for everyday living and entertaining. The gourmet kitchen shines with quartz countertops, a spacious island and stylish cabinetry, flowing seamlessly into the main living and dining areas. The downstairs guest suite offers flexability for visitors or a home office, while the upstairs primary retreat provides a relaxing escape with a spa-like bathroom and generous walk-in closets. This home reflects over $10,000 in uprgrades including an extended fenced in lanai, frameless shower doors and more! Residents of Osprey Ranch enjoy a welcoming community athomsphere with a scenic walking paths, beautiful community pool and convenient access to Horizon West's shopping, dining, top-rated schools and world class attractions. Experience luxury, comfort and the best of the Winter Garden lifestyle in this exceptional home. Call to schedule a private tour today!
Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)
Listing Agent: Kendra Wallace (407-457-7069)
17127 INGRAM BLUFF DR, WINTER GARDEN, FL 34787
$721,8206 Days on yellowkey MLS ID: G5113973
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2235 Built: 2026Monthly Fee: $150Community: Hamlin Meadows At HamlinSingle Family
Elementary School: Hamlin Elementary
Remarks: Virtually Staged. Under Construction. Sample Images The Anna Maria floor plan is a beautifully designed one-story home offering four bedrooms and two and a half bathrooms, thoughtfully arranged for comfortable everyday living. The open-concept layout features a spacious great room that flows effortlessly into the kitchen and dining area, creating an inviting space for entertaining or relaxing at home. The private primary suite includes a well-appointed ensuite bath and a generous walk-in closet. A covered patio extends the living space outdoors, while the two-car garage adds convenience and functionality. With 2,235 square feet of well-designed living space, the Anna Maria delivers both style and practicality.
17049 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787
$568,1916 Days on yellowkey MLS ID: G5113971
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1772 Built: 2026Monthly Fee: $150Community: Hamlin Meadows At HamlinSingle Family
Remarks: Virtually Staged. Pre-Construction. To be built. SAMPLE IMAGES The Amelia is a beautifully designed one-story offering three bedrooms and two baths, thoughtfully arranged for comfortable everyday living. The open concept layout features a spacious great room, dining room combo with no wasted space. The primary Owner’s Suite offers a spa-like experience with a generous walk-in closet and luxurious bath. Hamlin Meadows is the newest jewel of Horizon West, offering a diverse mix of rear-load homes in a highly sought-after Winter Garden location. Enjoy being minutes away from the vibrant Hamlin Town Center and major expressways.
1979 STANDING ROCK CIR, WINTER GARDEN, FL 34787
$520,00027 Days on yellowkey MLS ID: S5150723
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2082 Built: 2019Monthly Fee: $105 Tax: $8,301 (2025)Community: Oakland Trails Ph 2Single Family
Taxes:$8,301
Remarks: BUY THIS HOME WITH 100% FINANCING! LOCATION, LOCATION, LOCATION! Welcome to Your Trailside Oasis in Historic Oakland/Winter Garden! Nestled directly along the scenic West Orange Trail, this meticulously maintained, lightly lived-in bungalow offers the ultimate Florida lifestyle. Cycle straight into vibrant, historic downtown Winter Garden, or retreat to your own peaceful haven under the towering Live Oaks of Oakland Trails. Sophisticated Design Meets Modern Comfort...From the moment you arrive, the extended paver driveway and charming, shaded front porch welcome you home. Step inside to an airy, open-concept living area adorned with gleaming ceramic tile floors, quartz countertops, and upgraded builder finishes. Thoughtful, highly functional details elevate the main floor, including a stylish drop zone by the two-car garage, an under-stair coat closet, and a convenient powder room. High-end custom shades, luxury ceiling fans, and designer light fixtures make this residence completely turn-key and move-in ready. The second level opens into a versatile loft perfect for a media room, home office, or play space. The primary suite serves as a true sanctuary, boasting a grand double-door entrance, two spacious walk-in closets, and an ensuite bath with elegant quarts countertops. Two additional bright bedrooms and a dedicated upstairs laundry room complete this flawlessly designed upper level. Equipped with modern exterior lighting and a security camera system, this home offers total peace of mind. Outside your door, the vibrant Oakland Trails community features a resort-style pool, playground, dog park, and endless walking trails. Abundant dedicated street parking makes hosting family and friends effortless. Positioned perfectly between Clermont and Orlando, you will enjoy rapid access to the Florida Turnpike, 429, 408, and Highway 50. With Killarney Station right outside the neighborhood and the breathtaking Oakland Nature Preserve on the shores of Lake Apopka less than five minutes away, this is a dream destination for outdoor enthusiasts. Don't miss the chance to own this pristine, upgraded gem in one of Central Florida's most desirable trailside communities! Offering a lender credit towards costs or interest rate buy-down, when the client uses the preferred lender ACE Lending Group, ASK HOW.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Ariel Vargas (407-558-5161)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.