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$459,990
3 Beds ⋅ 3 Baths ⋅ Tribute At Ovation SubDv. ⋅ 34787 Zip Code
Amazing beautiful new corner townhome in Tribute at Ovation

15369 Burgtheater Drive, Winter Garden
$849,628
4 Beds ⋅ 5 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
SOLD DATA ONLY

16193 Honey Harvest Street, Winter Garden
$599,302
4 Beds ⋅ 4 Baths ⋅ Osprey Ranch - Phase 1 SubDv. ⋅ 34787 Zip Code
Brand new single family home in Winter Garden

15549 Gentle Rain Drive, Winter Garden
$937,239
4 Beds ⋅ 4 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Charming new construction home located in the beautiful neighborhood of Oakland Park. Golf cart to downtown Winter Garden!

1179 Wilder Oaks Way, Oakland
$170,000
4 Beds ⋅ 1 Baths ⋅ Joe Louis Park SubDv. ⋅ 34787 Zip Code
*Multiple offers received* Highest and best offers due by 3/30 7:00pm*** 4Bed- 1bath 1,369sqFt **Watch REAL WALKTHROUGH VIDEO** This 1,369-square-foot block home has 4 bedrooms and 1 bathroom and is located just 5 minutes from the picturesque Downtown Winter Garden! At the end of a quiet dead-end road, this home has no front neighbors, just greenery in front of your front door and a nice-sized backyard. It does need some tender loving care (TLC) to make it shine! This property is only 3 minutes away from Highway 429 and just 10 minutes from the West Orange Trail, making it ideal for easy access to transportation and outdoor activities. Within a few minutes drive, you'll find the “West Orange Recreation Center”, award-winning "Daniel’s Cheesesteak House", Zander's Park & Bouler Pool, and "Gelato Go". Everything for your entertainment is just a short distance away! This home is the perfect starter home for a family looking to settle down in a cozy and convenient location, with plenty of space and nearby amenities, it's a great place to call home!

508 Dunbar Avenue, Winter Garden
$1,089,631
5 Beds ⋅ 5 Baths ⋅ Silverleaf Oaks At Hamlin Phase 3a SubDv. ⋅ 34787 Zip Code
Sold Data Only. Information should be independently verified.

6239 Argent Wood Drive, Winter Garden
$125,000
Overstreet Crate SubDv. ⋅ 34787 Zip Code
Home builders! Discover the perfect lot for your dream project in the heart of Winter Garden. Whether you're looking to build spec, your dream home, or invest in future development. Less than a 5 min bike ride to Plant Street Market and everything Downtown Winter Garden has to offer, including restaurants, brewery, shopping, etc. There is a 1940's frame house on the site in unlivable condition, 2 bed/1 bath, approximately 500 sf. Water and sewer available for connection according to call with City of Winter Garden. Lot is zoned R-2. According to the City of Winter Garden Planning Department, this is considered a legal non-conforming lot. A Single family house is allowed to be built as long as it meets required setbacks. If smaller setbacks are needed for home plans, a variance can be applied for.

227 W Cypress Street, Winter Garden
$686,360
3 Beds ⋅ 2 Baths ⋅ Del Webb Oasis Phase 3 SubDv. ⋅ 34787 Zip Code
Sold data entry only.

13756 Fresh Ivy Street, Winter Garden
$275,000
34787 Zip Code
Come build your dream home in Downtown Winter Garden. Located just a few blocks from Plant Street this 47.5 by 140 foot corner lot spans 6,649 sf and falls within the Winter Garden Gold Cart District. Enjoy the farmers market on Saturday, or all the new & existing food options. As well as holiday events, decorations, pickleball courts and live entertainment all year round. Located conveniently to the Winter Garden Village and 429 - to Disney World. This fantastic opportunity won’t last long be one of the first to build a new construction home within blocks on Plant Street. City Sewer & Water.

326 S Main Street, Winter Garden
$1,371,753
5 Beds ⋅ 5 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
SOLD DATA ENTRY.

13223 Tollcross, Winter Garden
$542,525
4 Beds ⋅ 3 Baths ⋅ Silverleaf Reserve/Hamlin Ph 2 SubDv. ⋅ 34787 Zip Code
BEAUTIFUL NEW MERITAGE HOME

5014 Railroad Vine Alley, Winter Garden
$855,821
5 Beds ⋅ 5 Baths ⋅ Horizon Isle SubDv. ⋅ 34787 Zip Code
Private home office, perfect for telecommuting. Formal dining room for hosting dinner parties. Striking kitchen with center island and plenty of counter space. Spacious great room leading to covered patio. Extra Suite, perfect for guests or multi-generational families. Lavish primary suite with large primary bath and walk-in closet.

13147 Faro Court, Winter Garden
$540,000
4 Beds ⋅ 3 Baths ⋅ Silverleaf Reserve At Hamlin SubDv. ⋅ 34787 Zip Code
Beautiful new corner home 4/3 Meritage

4990 Railroad Vine Alley, Winter Garden
$899,000
4 Beds ⋅ 4 Baths ⋅ Lake Avalon Groves SubDv. ⋅ 34787 Zip Code
Exceptional 1+ Acre Property in Winter Garden – No HOA! Discover the flexibility and opportunity this unique property offers, set on a spacious lot with 100 newly planted Podocarpus trees for enhanced privacy and scenery. The main home features a bright and open floor plan with high ceilings and luxury vinyl flooring throughout—no carpet! The gourmet kitchen boasts custom cabinetry, granite countertops, a breakfast bar, and ample storage. The primary suite includes a large walk-in closet and a private en-suite bath, while three additional bedrooms provide generous space for family or guests. A highlight of this property is the detached 1-bedroom, 1-bath guest suite with a full kitchen, ideal for rental income, Airbnb, or an in-law suite. Outdoor living shines with a screened-in pool with a dedicated full pool bath, an extended patio with a fire pit. The oversized 3-car garage offers RV parking, workshop space, and attic storage with a pull-down stairway. Additional features include energy-efficient Icynene insulation, double-paned windows, and a ceramic-coated well reaching 250 feet into the aquifer. Seller updates include but are not limited to Factory Enduroshield Master glass shower doors, new bathroom sinks, and a pumped septic tank. Enjoy fireworks views from the backyard and the convenience of being minutes from major roads, shopping, dining, hospitals, and attractions. All appliances in both the main home and guest suite convey, and the seller is offering a home warranty. Don’t miss this incredible opportunity—schedule your showing today!

17572 Davenport Road, Winter Garden
$530,000
4 Beds ⋅ 2 Baths ⋅ Glenview Estates 1st Add SubDv. ⋅ 34787 Zip Code
This beautifully renovated 4-bedroom, 2-bathroom home perfectly combines a modern aesthetic with a charming, welcoming feel. Situated in Winter Garden in a golf cart approved zone and no HOA! The open floor plan is filled with natural light, showcasing bright light walls and flooring that are thoughtfully balanced by dark hardware and accent details, creating an updated yet cozy atmosphere. Soaring cathedral ceilings enhance the spacious feel, while brand-new luxury vinyl plank flooring flows throughout, adding both style and durability. The kitchen is a showstopper, featuring all-new GE stainless steel appliances, soft-close cabinets, a striking stone honeycomb backsplash. The oversized island with modern overhanging pendant lights is a standout feature, offering extra storage space, expansive prep and serving areas, and room for seating — ideal for family gatherings or hosting guests. Plus, with a brand-new roof (2024) with under soffit lighting, 2022 AC, and 2022 water heater, you will have peace of mind for years to come. Step outside to the expansive, fully fenced backyard complimented with a screened-in patio offering a serene retreat, perfect for enjoying the outdoors without the nuisance of pests. And the location couldn’t be better! This home is just minutes away from Winter Garden Village, offering a variety of shopping, dining, and entertainment options, and only a short drive to the vibrant Plant Street Market. Plus, with Lake Apopka just a short walk or bike ride away, you’ll have easy access to nature trails, water activities, and scenic views. This is an incredible opportunity to own a beautifully renovated home in one of Winter Garden's most sought-after neighborhoods. Don’t wait — schedule your showing today and make this dream home yours!

1022 Glenharbor Circle, Winter Garden
$729,490
3 Beds ⋅ 2 Baths ⋅ Del Webb Oasis Ph 3 SubDv. ⋅ 34787 Zip Code
New Construction

15452 Orchard Garden Street, Winter Garden
$830,240
5 Beds ⋅ 4 Baths ⋅ Silverleaf Oaks/Hamlin Ph 3a SubDv. ⋅ 34787 Zip Code
New Construction

6614 Foggy Silver Road, Winter Garden
$725,540
3 Beds ⋅ 2 Baths ⋅ Dell Web Oasis SubDv. ⋅ 34787 Zip Code
New Construction

15434 Orchard Garden Street, Winter Garden
$483,000
4 Beds ⋅ 2 Baths ⋅ Winter Garden Shores Add 02 SubDv. ⋅ 34787 Zip Code
*** BACK-UP OFFERS are strongly encouraged. Inquire today! *** Charming POOL home with a fenced-in backyard oasis just footsteps from historic downtown WINTER GARDEN! This beautiful retreat with NO HOA sits on a QUARTER of an acre and features 4-bedrooms, 2-baths, a dining space that opens to a family room, a 13 X 22 living room, a laundry room with ample storage, a generously sized screened-in porch (~12X38), a serene backyard perfect for relaxation and entertaining, and a utility shed for added storage. Step through the FRENCH doors onto the porch and take in the lush private landscaping. The spacious kitchen boasts GRANITE countertops and stainless steel appliances, making meal prep a delight. UPDATES include: double-pane windows and roof (2014), water heater (2023). This move-in-ready home is located in the GOLF CART district near the vibrant historic downtown Winter Garden, where you can explore charming boutiques, exceptional dining, the award winning Farmers Market, and access to the 22 mile long West Orange Trail. Ride your golf cart to dinner or take a leisurely stroll into town. Enjoy stunning sunsets, a public boat ramp, an expansive park, and a playground at Newton Park, overlooking Lake Apopka. Local events are hosted at this park, including July 4th fireworks, which can be seen from the front yard! With easy access to major highways, shopping, and entertainment, this home offers both tranquility and convenience. Don’t miss this rare opportunity to own a piece of Winter Garden’s charm! Note: the pool is in need of repairs. Property is being sold AS-IS.

427 N Lakeview Avenue, Winter Garden
$1,249,334
5 Beds ⋅ 5 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
WESTHAVEN AT OVATION

13271 Tollcross Way, Winter Garden
$1,000,000
5 Beds ⋅ 5 Baths ⋅ Westhaven/Ovation SubDv. ⋅ 34787 Zip Code
The property at 13235 Tollcross Way in Winter Garden, Florida, is a newly constructed single-family residence located in the Westhaven at Ovation - Retreat community. This two-story home spans 3,778 square feet and includes 5 bedrooms and 4.5 bathrooms. ?Upon entering, you're greeted by a striking two-story foyer that leads to an open-concept kitchen seamlessly connected to the main living area, offering prime access to the outdoor patio. The second floor features an oversized primary bedroom with dual walk-in closets and a spa-like primary bath. Additionally, there's a loft space ideal for family activities.

13235 Tollcross Way, Winter Garden
$770,800
3 Beds ⋅ 3 Baths ⋅ Silverleaf Reserve/Hamlin Ph 2 SubDv. ⋅ 34787 Zip Code
Sold data only

16439 Silver Grove Boulevard, Winter Garden
$460,000
7 Beds ⋅ 4 Baths ⋅ Millers Pt Winter Garden SubDv. ⋅ 34787 Zip Code
Incredible location in the HISTORIC DISTRICT of DOWNTOWN WINTER GARDEN-great opportunity to buy now and build your own custom home in the GOLF CART DISTRICT. Currently the property is home to TWO EXISTING/OCCUPIED RENTAL HOMES! The VALUE OF THIS PROPERTY IS PRIMARILY IN THE LAND! Both of the existing buildings need significant repairs and are sold as-is/where is. The buyer is responsible for determining any/all allowable future use with the City of Winter Garden. Zoned R-2 RESIDENTIAL/TWO FAMILY, this .25 acre property is located across the street from Foundation Academy/preschool, and less than 1/10 mile from Plant Street. Building 1 (a white wood frame 2 story with asbestos siding & metal roof) was built in 1925 and consists of 2, 2 bedroom, 1 bath units, labeled A and B. This building is approximately 1902 sq. ft heated per tax records. Building 2 (located behind bldg 1) is a two story concrete block structure with storage on the ground level and an attached carport/shed. Building 2 was built in 1960 and contains a second floor apartment (C) with 2 bedrooms/1 bath, and (D) a 1st floor efficiency apartment. Building 2 is occupied by two tenants and has a large storage room below the 2nd floor apartment. The tax records indicate the heated square footage of Building 2 is 1687. Both buildings are connected to city water, sewer and Lake Apopka natural gas with Duke Energy for electricity. The West Orange Trail and all of the most desirable amenities of Downtown Winter Garden are just steps from your front door, including the national award winning Farmer's Market, numerous restaurants, bars, coffee and ice cream shops, boutiques/gift shops, The Crooked Can Brewery, Plant Street Market, Railroad & Heritage Museums, Winter Garden Theatre, Splash Pad, SOBO Art Gallery, doctors/dentists, and lash/nail/beauty & barber shops. Locals and visitors enjoy the many seasonal events like Spring Fever in the Garden, Oktoberfest, Winter Garden Halloween Experience, and Light Up Winter Garden. Quick and easy access to public schools and daycares too! SOLD AS-IS/Seller will make no repairs. Tenants are on month to month leases and the new owner inherits the tenants. Leases available for review upon acceptance of an offer. Buyer/Buyer's agent are responsible for verifying all information contained herein.

100 N Main Street, Winter Garden
$399,000
2 Beds ⋅ 1 Baths ⋅ Winter Garden Shores SubDv. ⋅ 34787 Zip Code
Charming Downtown Winter Garden Home – Prime Opportunity - Just 4 Blocks from Plant St. and 3 Blocks from Lake Apopka! Seize this rare opportunity to own a home in the heart of Downtown Winter Garden for under $400,000! Nestled on a ¼-acre lot adorned with beautifully maintained oak trees, this property offers both charm and potential. The large fenced yard features alley access, providing convenient entry from both the front and rear of the home. A shed is included, with the flexibility to replace it with another structure, such as a garage or additional living space. Zoned R-2, this lot presents an excellent opportunity—whether you’re looking for a fixer-upper or an investment property. This inviting 2-bedroom, 1-bathroom home includes an office, workshop, dining room, family room, and living room—providing ample space to personalize and enjoy. Major updates have already been completed, including new plumbing, electrical, and HVAC systems, along with a NEW ROOF installed in 2023. Relax on the charming front porch and take in the cool evening breeze. The covered carport accommodates one vehicle, while the extended driveway offers additional parking. Located in the coveted Golf Cart District, you’re just a short way from local restaurants, boutique shops, and the award-winning Winter Garden Farmers Market. Living in Downtown Winter Garden offers more than just homeownership—it provides an opportunity to be part of a vibrant, close-knit community with year-round events and activities. Don’t miss this exceptional opportunity to experience the charm, convenience, and unique lifestyle this neighborhood has to offer. Schedule your showing today!

412 N Boyd Street, Winter Garden
$210,000
3 Beds ⋅ 1 Baths ⋅ Bay St Park SubDv. ⋅ 34787 Zip Code
A Home of Warmth and Light - A hidden gem, so full of cheer, A place to love, to hold so dear. Three bright rooms, a bath with grace, A charming, peaceful living space. Built with care in days gone by, Where sunsets paint the open sky. A tranquil lot, both wide and fair, With memories waiting to grow and share. Close to shops and schools so near, Highways, roads, and places dear. Near the shops and schools so close, Highways leading where life flows. A perfect start, a dream come true, A space to build, to start anew. The chance is here, don’t wait too long, cause if you wait it could be gone.

1130 E Bay Street, Winter Garden
$230,000
2 Beds ⋅ 2 Baths ⋅ Windtree Gardens SubDv. ⋅ 34787 Zip Code
Imagine stepping into your new home at 112 Windtree Lane, Unit 203, in Winter Garden, FL, where modern elegance effortlessly intertwines with comfortable living. This beautifully renovated 2-bedroom, 2-bathroom condo, spanning 918 square feet, invites you to experience a chic, modern vibe from the moment you walk in. As you enter, you're greeted by a fresh, open living space, complete with a newly textured ceiling that exudes sophistication. The luxury vinyl flooring, state-of-the-art and seamless, sets the stage for the stylish foundation of this home. The kitchen, the true heart of this condo, dazzles with brand new cabinets and breathtaking butcher block countertops, ideal for those who love to cook and entertain. Both bathrooms have been updated with a modern touch, ensuring a sleek experience every day. With the addition of a brand new washer and dryer, this home is truly move-in ready. Nestled just 1.5 miles from the vibrant Downtown Winter Garden, you'll have convenient access to a myriad of dining, shopping, and entertainment options. Every detail has been meticulously curated, offering a turnkey experience that awaits your personal touch. Embrace the opportunity to make this stunning condo your own and start your new chapter in style.

112 Windtree Lane Unit 203, Winter Garden
$278,000
3 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
INCLUDES GARAGE (valued at $40,000)!! 3 months of association dues paid at closing! BEST VALUE in the exclusive gated community of Southern Pines in the heart of Winter Garden! New luxury vinyl plank flooring throughout and newer stainless-steel appliances including full size washer and dryer. Just painted and ready for move in! Includes private oversized one car garage. Split bedroom floorplan with spacious layout in the middle. Dining area can accommodate an oversized dining room table. Living room has room for a large sectional sofa. The sitting area has lots of natural light next to the windows and has a custom built in desk and shelving. Great location in Southern Pines puts you steps away from the playground, mailbox, clubhouse and pool! Residents of Southern Pines have access to several amenities, including a swimming pool, spa, outdoor kitchen with grills, tennis court, racquetball and basketball courts, fitness center with a kid's playroom, sand volleyball court, covered playground, carwash station and a clubhouse. The clubhouse has a new movie theatre, game room with pool table, conference room and business center. Association fee includes cable, internet and water. Minutes to Historic Downtown Winter Garden and easy access to the Turnpike and 429. Not far from theme parks and everything Orlando has to offer. This 3 bed/2 bath with hard to find garage won't last long!

130 Southern Pecan Circle Unit 205, Winter Garden
$775,000
3 Beds ⋅ 2 Baths ⋅ 34787 Zip Code
~Exceptional One-Owner Home in a Prime Location! This unique property offers a peaceful rural setting with convenient access to everything. Located on the 4th Parcel from Maguire Rd. in unincorporated Orange County, this nearly 2-acre agricultural-zoned lot features stunning Grandfather Oaks and mature landscaping. The spacious 3-bedroom, 2-bathroom home includes a large great room with a fireplace, as well as a separate living room. Enjoy the serene views from the expansive screened rear porch, overlooking the lush green acreage. Don't miss out on this rare opportunity—schedule your showing today!

11207 Roberson Road, Winter Garden
$551,790
3 Beds ⋅ 3 Baths ⋅ Silverleaf Oaks SubDv. ⋅ 34787 Zip Code
Sold Data Entry Only

6466 Tabebuia Parkway, Winter Garden
$100,000
2 Beds ⋅ 1 Baths ⋅ Overstreet Crate SubDv. ⋅ 34787 Zip Code
Investor special in the heart of Winter Garden! Tear it down for fix it up! This 2-bedroom, 1-bathroom home sits on almost a quarter acre and needs a full rehab. The property offers a great location, just minutes from Historic Downtown Winter Garden, with its popular restaurants, shops, and the West Orange Trail. Convenient access to major highways, including SR 429 and Florida’s Turnpike. No HOA. A great opportunity for investors or builders looking for a project. Comps in area being upgraded to 3 bedrooms 2 baths to increase ROI!!

838 Bethune Avenue, Winter Garden