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$203,000
3 Beds ⋅ 1 Baths ⋅ Bay St Park SubDv. ⋅ 34787 Zip Code
Super Rare Opportunity at a Super Rare price in Winter Garden! Don't miss out on this 3 bedroom home with a brand new HVAC 2024, laminate flooring throughout with the exception of the bonus room. Natural gas range, Updated bathroom, updated electrical panel and more!  Bonus room can be used for a multitude of purposes. Exterior features a shed, extra long driveway and NO HOA!  A short  distance to the West Orange Trail, local shops, restaurants, and farmers markets—this location truly can’t be beat. Don’t miss your opportunity to own a piece of Winter Garden charm—schedule your private showing today!

1170 E Bay Street, Winter Garden
$1,389,375
4 Beds ⋅ 3 Baths ⋅ Acreage & Unrec SubDv. ⋅ 34787 Zip Code
*Video and 3D Tour Available! * Bring the horses! This 5-acre lot has not only a beautiful home, but room for the horses to run and live comfortably in your back yard. The home is situated at the end of quiet Tower Pine Dr. and is FULLY FENCED. The fresh landscaping and circle driveway greet you when you pull through the gate. This home has formal living and dining rooms as well as an open concept between the kitchen and the family room. You’ll find tile floors throughout and new carpet in the secondary bedrooms. CROWN MOLDING, a stone accented WOOD-BURNING FIREPLACE and French doors to the pool make this living space warm and inviting! Make your favorite dishes in the eat-in GOURMET KITCHEN with a double built-in oven, induction cooktop, granite countertops, large island, and walk-in pantry. Movie night is calling from the MEDIA ROOM with the BOSE SURROUND SOUND, screen and projector. The spacious primary bedroom has FRENCH DOORS to the patio, 2 walk-in closets, dual vanities and dual shower heads. The front bedroom has a PRIVATE BATH while the 3rd and 4th bedrooms share a hall bath. There is a large laundry room with utility sink and EXTENDED 3-CAR GARAGE. Enjoy the sunsets from the SCREENED PATIO and cool off in the SALT-WATER POOL. The HEATED SPA and rock feature also have WATERFALLS. Outside you’ll find a 3-STALL BARN with a 30x30 turnout, an 18x12 FEED & TACK ROOM, and a 12x12 WASH STALL with rubber mats. There are 2 fenced and cross-fenced PASTURES attached to the 80x120 ARENA with a clay footing and sand topper. The SCREEN ROOM is just waiting for you with a hot tub and room for a tiki bar! There’s a TRACTOR/STORAGE BARN and an 18x24 SHED to keep you organized! Additional upgrades in the home include a NEWER ROOF (2021), blown-in insulation (2024), gutters, irrigation and landscape lighting plus there are ceiling fans throughout the property. Don’t miss your chance to make this one your own!

9019 Tower Pine Drive, Winter Garden
$635,000
3 Beds ⋅ 1 Baths ⋅ Winter Garden Shores Add 02 SubDv. ⋅ 34787 Zip Code
SOLD DATA ENTRY ONLY.

374 N Boyd Street, Winter Garden
$408,000
3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 4a SubDv. ⋅ 34787 Zip Code
NEW LOWEST PRICE! SELLER HIGHLY MOTIVATED. Least expensive adorable just 2 years newest impeccable, vacant & available Ibis townhome, offers a perfect blend of comfort and convenience with 3 bedrooms, 2.5 baths, 1-car garage, featuring a Stainless-Steel Kitchen Appliances package, granite counter tops, an inviting open-concept first floor with ceramic tile flooring perfect for gathering. Upstairs' Laundry Room includes Washer & Dryer. Master bath with double sinks and shower glass doors. Covered Lanai, walkway and driveway have elegant brick pavers. Waterleigh community includes lawn care, top-notch amenities speak for themselves—resort-style pools, scenic views, tennis courts, gym, sand volleyball court and more. This townhome offers everything you need to embrace a warm, welcoming lifestyle in a prime location. ZERO DEFECTS! It shows as a model. Decorations are not included.

12035 Holystone Street, Winter Garden
$663,285
4 Beds ⋅ 4 Baths ⋅ Silverleaf Reserve At Hamlin SubDv. ⋅ 34787 Zip Code
Alcott II Floorplan

5243 Citrus Leaf Boulevard, Winter Garden
$705,114
4 Beds ⋅ 3 Baths ⋅ Horizon Isle SubDv. ⋅ 34787 Zip Code
Beautiful single family house at Horizon Isle - Winter Garden

13130 Dendy Way, Winter Garden
$315,000
4 Beds ⋅ 2 Baths ⋅ Orange County SubDv. ⋅ 34787 Zip Code
Charming Winter Garden Home – Prime Location Near Top-Rated Schools! This well-priced 4-bedroom, 1.5-bath home is a fantastic find for buyers or investors looking for value and location. Inside, you'll find a welcoming living room that flows into a spacious bonus room—perfect as a family room, home office, or potential 5th bedroom (formerly a garage). The open dining area connects to a thoughtfully updated kitchen featuring granite countertops, stainless steel appliances, and rich wood cabinetry—a great space for hosting or everyday meals. Down the hall are four separate bedrooms, including a primary bedroom with its own private half-bath, plus a shared full bathroom. Step outside to a generously sized backyard—ideal for adding a fence, starting a garden, or creating your outdoor retreat. Located just across the street from the scenic Tucker Ranch Recreation and Nature Complex, this home puts outdoor adventure and relaxation right at your doorstep. Attention investors: The home is currently occupied by a long-term tenant (now on a month-to-month lease) who has lived there for 7 years and would love to stay. ? Flexible layout | Excellent investment | Move-in ready | Prime location Don't miss out—this property is priced for a quick sale and won't last long!

154 Avalon Road, Winter Garden
$639,000
5 Beds ⋅ 4 Baths ⋅ K Hovnanian Osprey Ranch Llc SubDv. ⋅ 34787 Zip Code
ENTER ONLY SOLD DATA

12506 Westhaven Oak Drive, Winter Garden
$783,000
4 Beds ⋅ 4 Baths ⋅ Heritage/Plant Street SubDv. ⋅ 34787 Zip Code
Sold off market.

Winter Garden
$427,000
3 Beds ⋅ 1 Baths ⋅ G T Smith Sub 7 SubDv. ⋅ 34787 Zip Code
1940s Historic Home on 1 Acre total in Winter Garden. Close to Fowler Groves. This home has been in the same family for generations. No HOA! Horse farm across the street. Mature Oak trees, Mature Honey Mango tree. Beautiful front porch to relax and enjoy the country life in the city. Verify with the County to build another home on the property, which is 2 lots. Downtown Winter Garden, 3 miles drive on South Dillard St. Close to restaurants and shopping. Centrally located to the 429 to Downtown Orlando and Florida Turnpike. City water is available through Winter Garden.

485 Palm Street, Winter Garden
$280,000
4 Beds ⋅ 2 Baths ⋅ Partlow Acres SubDv. ⋅ 34787 Zip Code
Welcome to your dream home in Winter Garden, FL! This stunning NO HOA 4-bedroom, 2-bathroom with residence offers the perfect blend of comfort and serenity living. The open floor plan allows for seamless flow between the living, dining, and kitchen areas, making it ideal for entertaining family and friends. The kitchen features ample cabinetry, appliances, and perfect for culinary adventures. Retreat to the serene master suite, and complete with a private bathroom. Three additional well-sized bedrooms provide plenty of space for family, guests, or a home office. New AC and roof updated 2019. Step outside to your private backyard oasis, perfect for outdoor gatherings or simply relaxing in the Florida sunshine. Located in the highly sought-after Winter Garden area, you'll enjoy easy access to shopping, dining, and top-rated schools. Don't miss your chance to make this exquisite home yours! Schedule a showing today and experience the charm of Winter Garden living!

1181 Partlow Drive, Winter Garden
$276,000
3 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
LOCATION, LOCATION, LOCATION, Rare opportunity to acquire a Large 3/2+ Open Office Condominium in the Gated Southern Pines Community that is located in the heart of the City of Winter Garden. The Front Door Entry leading to this unit is located on First Floor, taking stairs to the Open and Spacious residence all being located on the second floor with no residence above you. Waterproof Luxury Vinyl is throughout the entire living area and each room is designed with Window Treatments, Crown Molding, Ceiling Fans and Fresh paint. The kitchen is dressed with Stainless Steel Appliances and includes a laundry closet housing a Full Washer and Dryer for convenience. The living area is open and spacious to the kitchen and designated dining area and then leads into an additional open room space that is designed as a sunroom/office/extra den. Southern Pines, within its gates, is designed to be a resort community with onsite management, resort style pool and lounging areas, fitness center, covered playground, tennis courts and designated car wash. This community is desirous because of its centrally location and short miles from Shopping, Restaurants, the Infamous Historic Downtown, Medical Offices and Hospital. Minutes away from Highway 429 leading to Turnpike. Its a must See and a Must Visit. Schedule your viewing today.

130 Southern Pecan Circle Unit 204, Winter Garden
$85,000
Merchants Sub SubDv. ⋅ 34787 Zip Code
ENTITLED SINGLE LOT With APRROVED PLANS! | 3 Bed 2 Bath 2 Car Garage | Build Your Dream - Spec Home -Investment Home in the Heart of Winter Garden! | 821 Pine St, Winter Garden, FL 34787 Rare Ready-to-Build Lot with Approved Plans! High & Dry Ready to Build! Welcome to a highly sought-after lot located in the heart of Historic Downtown Winter Garden! This vacant residential lot is a rare gem—fully permitted and ready for construction with approved architectural plans to build a stunning two-story single-family home. Prime Location, Endless Possibilities: • Just minutes from Downtown Winter Garden – enjoy the farmers market, boutiques, restaurants, and live music events • Close proximity to Winter Garden Village, local hospitals, and top-rated Orange County Public Schools • Walking or biking distance to parks, trails, and community events • NO HOA – freedom to build and live without restrictions! Features & Highlights: • High & Dry Ready to Build lot in an established area of Winter Garden Florida. • Includes approved construction plans for a spacious custom home • Utilities nearby – ready for immediate development • Perfect for primary residence, second home, or investment opportunity Why This Property? This lot is ideal for anyone looking to build in a vibrant, walkable community where charm meets modern convenience. Without the burden of HOA rules or fees, you have the flexibility to create a home that suits your unique lifestyle. Schedule a Showing Today! This opportunity won’t last long! Land like this in Winter Garden is disappearing fast. Call or text Heather Grooms. Powered by The Landlord Finders Build Real Estate today and make this ready-to-build lot yours! Visit BuildingFloridaRealEstate

821 Pine Street, Winter Garden
$210,000
34787 Zip Code
ZONED RESIDENTIAL AND OVER JUST A HALF ACRE . NO HOA & NOT IN A FLOOD ZONE 120 FT OF ROAD FRONTAGE. All information intended to be accurate but buyer to due diligence including but not limited to all facts with county, local government and HOA officials to make sure property meets their specific needs.

Avalon Road, Winter Garden
$247,500
M C Britt Sub 2 SubDv. ⋅ 34787 Zip Code
Some properties are just land. This one tells a story. Quietly held for generations—pristine and untouched, never built on, never listed—this rare homesite in Winter Garden’s Golf Cart District is now ready for its first chapter. Just blocks from Plant Street’s farmers market, dining, and community events, it offers a rare blend of peace, walkability, and charm. Enjoy pickleball courts, nature trails, and live entertainment year-round—and you will love the proximity to the Winter Garden Village, Disney World, and major highways. Build where legacy meets lifestyle, and timeless living begins.

W Vining Street, Winter Garden
$842,650
5 Beds ⋅ 5 Baths ⋅ Silverleaf Reserve/Hamlin Ph 2 SubDv. ⋅ 34787 Zip Code
Hayden Floor plan at Silverleaf Reserve

16457 Silver Grove Boulevard, Winter Garden
$882,045
5 Beds ⋅ 5 Baths ⋅ Silverleaf Reserve At Hamlin Phase 2c SubDv. ⋅ 34787 Zip Code
Hayden floorplan Silverleaf Reserve

5253 Citrus Leaf Boulevard, Winter Garden
$883,005
5 Beds ⋅ 5 Baths ⋅ Silverleaf Reserve/Hamlin Ph 2 SubDv. ⋅ 34787 Zip Code
Hayden floorplan Silverleaf Reserve

16477 Silver Brook Way, Winter Garden
$858,325
5 Beds ⋅ 5 Baths ⋅ Silverleaf Reserve At Hamlin Phase 2c SubDv. ⋅ 34787 Zip Code
Silverleaf Reserve by Meritage Homes

16543 Silver Brook Way, Winter Garden
$911,195
5 Beds ⋅ 5 Baths ⋅ Silverleaf Reserve/Hamlin Ph 2 SubDv. ⋅ 34787 Zip Code
Hayden Floor Plan on Silverleaf Reserve

5235 Citrus Leaf Boulevard, Winter Garden
$380,000
3 Beds ⋅ 3 Baths ⋅ Longleaf At Oakland SubDv. ⋅ 34787 Zip Code
.**BACK ON THE MARKET**Welcome to this exceptionally appointed town home located in Longleaf at Oakland in Oakland, Florida. This charming residence offers 3 bedrooms and 2.5 bathrooms, perfectly designed with an open-concept layout that features stylish laminate flooring in the living and dining areas. The kitchen is truly the heart of the home, boasting a large island with seating for four, L-shape granite countertops, 42-inch cabinets, and stainless steel appliances. Large kitchen windows flood the space with natural light, creating a bright and inviting atmosphere. Adjacent to the kitchen is a laundry room with storage shelves and a walk-in pantry closet for ample storage. Step outside through a glass French door to a private courtyard paved with bricks, ideal for outdoor relaxing or entertaining. The courtyard leads to a 2-car detached garage and additional parking pad. Inside the garage, you'll find a whole-house water treatment system for convenience and efficiency. Upstairs, the master suite features a walk-in closet, a double sink with granite countertops, and a spacious walk-in shower. There are two additional bedrooms and a second full bathroom, providing plenty of space for family or guests. The stairwell wall is beautifully accented with a custom-designed feature, adding a touch of elegance. For added security, the home is wired for a security system with the option to add cameras. The community offers fantastic amenities including a pool, playground, and sidewalks, making it a great place for families and outdoor activities. Located close to shopping centers and major roads, this property is perfect for first-time home buyers, second homeowners, or investors. Currently rented at $2,600 monthly through 2026, offering immediate rental income. Don’t miss the opportunity to make this exceptional town home your new home!

2203 Gopher Tortoise Terrace, Oakland
$2,050,000
4 Beds ⋅ 5 Baths ⋅ Acreage & Unrec SubDv. ⋅ 34787 Zip Code
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.

9940 Black Bear Lane, Winter Garden
$1,284,682
5 Beds ⋅ 5 Baths ⋅ Oakland Park South SubDv. ⋅ 34787 Zip Code
The Crabtree by David Weekley Homes is a beautifully designed two-story home featuring an open-concept layout, a main-level owner’s suite, elegant finishes, and a detached garage apartment ideal for guests, family members, or a private office. Located in Oakland Park, a walkable, green-certified community in Winter Garden, residents enjoy resort-style amenities, scenic trails, and close proximity to historic downtown.

1245 Wilder Oaks Way, Oakland
$857,000
3 Beds ⋅ 2 Baths ⋅ Avalon Estates SubDv. ⋅ 34787 Zip Code
Nestled within a tranquil cul-de-sac in the sought-after Avalon Estates. A rare fusion of rustic charm and modern opulence. Situated on 5.47acres, Fully cross fenced and mostly irrigated equestrian-zoned property, rendering it an ideal haven for equestrian enthusiasts or those seeking a secluded sanctuary mere minutes from Winter Garden's amenities. The residence encompasses 1700 sq ft, featuring 3 bedrooms and 2 bathrooms, with a well-designed split floorplan ensuring a seamless flow. The exquisitely updated primary bathroom serves as a serene retreat after a long day. The screened pool area is perfect for entertaining with views of Disney fireworks. Every room boasts breathtaking views that must be seen to be believed. The property also includes a spacious barn, and with no HOA in the neighborhood. The property's proximity to Lake Louisa State Park, with 19 miles of horse trails, further enhances its appeal. This rare opportunity to own an expansive tract of land in Winter Garden should not be missed.

11115 Romance Court, Winter Garden
$700,000
3 Beds ⋅ 2 Baths ⋅ G T Smith Sub SubDv. ⋅ 34787 Zip Code
Step into a piece of Winter Garden's rich history with this captivating, charming historic home in the "golf district" in the heart of downtown Winter Garden. Nestled in the heart of downtown Winter Garden, enjoy easy access to the widely popular Plant Street farmer's market, West Orange Trail, and the famed Crooked Can Brewery. This prime location home is nestles in the heart of downtown Winter Garden with easy access to local shops, restaurants, parks, and the vibrant community events that define this sought-after area. Original architectural details reflects the home's 1920's heritage, offering a unique blend of past and present. Some of modern highlights include Brazilian Cherry hardwood floors, Roof 2018, AC 2019, and replumbed in 2020. Your spacious living amenities include 3 bedrooms with large walk-in closets, 2 full bathrooms, and an ample upstairs retreat generous enough for families or those seeking to room to grow. Don't miss the opportunity to own a piece of Winter Garden's history. Schedule your private showing today and envision the endless possibilities this home has.

40 W Smith Street, Winter Garden
$407,817
3 Beds ⋅ 3 Baths ⋅ Summerlake Pd Ph 2c-2e SubDv. ⋅ 34787 Zip Code
N/A

15588 Blackbead Street, Winter Garden
$203,000
2 Beds ⋅ 2 Baths ⋅ Windtree Gardens Condo Ph 01 SubDv. ⋅ 34787 Zip Code
Move-in ready 2-bedroom, 2-bathroom gem located in the heart of Winter Garden. Whether you're looking for your first home or a smart investment opportunity, this property checks all the boxes! Step inside to find freshly painted interiors, easy-to-maintain ceramic tile flooring throughout, and a split-bedroom layout that offers added privacy—perfect for roommates, guests, or growing households. The spacious master suite is tucked away on one side of the home, while the second bedroom and bathroom are situated on the opposite wing. Enjoy peaceful mornings or relaxing evenings in your screened-in patio area, ideal for outdoor living without the bugs. Just outside, you'll find 2 assigned parking spaces for added convenience. Located directly across from a serene lake, the community also features amenities like a swimming pool and basketball court, giving you a lifestyle of comfort and recreation. Plus, the brand-new roof (2024) AC from 2020 adds long-term value and peace of mind. Centrally located near shopping, dining, major highways, and historic Downtown Winter Garden, this home won’t last long!

51 Windtree Lane Unit 101, Winter Garden
$589,000
4 Beds ⋅ 3 Baths ⋅ Highland Ridge Phase 2 111/6 Lot 175 SubDv. ⋅ 34787 Zip Code
SOLD data entry

11945 Bracco Street, Winter Garden
$190,000
2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo SubDv. ⋅ 34787 Zip Code
Welcome to the largest 2 bedroom/2 bath Cypress Model condo at the 4-Star rated Grove Resort & Spa Orlando! This high floor, corner unit offers a spacious, split bedroom open layout with over 1,400+ SF of living area. This model features an oversized Primary Suite with separate corner sitting area and guest bedroom features 2 queen size beds. This condo sleeps 8! Other features include a modern interior with solid wood cabinets and granite countertops in the kitchen and baths, stainless steel appliances, in-unit laundry, and all furniture and furnishings ready for your turn-key vacation resort. The resort features outstanding amenities including 2 on-site restaurants, spa, fitness center, arcade game room, three pools, private access to Lake Austin,FREE SHUTTLES TO DISNEY PARKS and the on-site SURFARI WATER PARK complete with lazy river, pool-side restaurant and bar, and even a FLOWRIDER® double surf simulator. This is a Walt Disney World Good Neighbor® Hotel and less than 5 miles from the world famous Walt Disney World® Resort and Theme Parks. Also, just 4.3 miles to Margarita Resort and all the restaurants and shops in Kissimmee. This amazing condo-hotel unit also offers the convenience of an in-house, on-site hotel rental program which allows you to rent the property when not in use and features a VIP Check-In for condo owners. ALL UTILITIES INCLUDED IN MONTHLY MAINTENANCE!

14501 Grove Resort Avenue Unit 3636, Winter Garden
$122,000
3 Beds ⋅ 1 Baths ⋅ Joe Louis Park First Add SubDv. ⋅ 34787 Zip Code
$150,000?! $150,000?! That's right! **Investor Special**Welcome to 1701 E Bay Street, Winter Garden! This charming mid-century gem offers 825 square feet of cozy living space, featuring 3 bedrooms and 1 bathroom, all nestled on a spacious .15-acre lot. With fresh interior paint and delightful character throughout, this home is perfect for an owner-occupant seeking a unique abode or an investor looking for a fantastic opportunity. Enjoy the freedom of NO HOA while being just moments away from the vibrant heart of downtown Winter Garden, major thoroughfares, and the world-renowned Central Florida theme parks. Don’t miss the chance to own a piece of Winter Garden’s charm—schedule your tour today! **Property needs some updating and rehab**

1701 E Bay Street, Winter Garden