Winter Garden Waterfront Homes For Sale By Owner (72 Homes)

  • Home For Sale $267,500
    • 3Bed
    • 2Baths
    • 1,596Sq ft
    17515 MANDARIN CIRCLE , Winter Garden,...

    Wonderful home with recent updates located on a cul-de-sac, nearly ½ acre lot, no hoa and public... Read More

  • Home For Sale $440,000
    • 3Bed
    • 2.5Baths
    • 1,988Sq ft
    8812 BISMARCK PALM DRIVE , Winter Garden,...

    Beautiful property in a very exclusive community, only minutes away from all theme parks and... Read More

  • Home For Sale $345,000
    • 4Bed
    • 3Baths
    • 1,986Sq ft
    2246 BLACK LAKE BOULEVARD , Winter Garden,...

    The expansive covered front porch of this beautifully updated home is perfect for spending time... Read More

  • Home For Sale $711,995
    • 5Bed
    • 4.5Baths
    • 3,811Sq ft
    8168 TOPSAIL PLACE , Winter Garden, Florida

    Under construction. the madeira palm beach features a welcoming foyer leading to your... Read More

  • Home For Sale $675,000
    • 5Bed
    • 4Baths
    • 4,063Sq ft
    1845 BLACKWATER COURT , Winter Garden,...

    Beautiful and spacious 5 bedroom, 4 bath home in one of the most sought after communities in lake... Read More

  • Home For Sale $480,000
    • 3Bed
    • 2Baths
    • 2,522Sq ft
    15661 SHOREBIRD LANE , Winter Garden, Florida

    Motivated seller. bring all offers! like new! 3,022 sqft. very beautiful and spacious home in the... Read More

  • Home For Sale $525,000
    • 4Bed
    • 3.5Baths
    • 3,090Sq ft
    9295 BRADLEIGH DRIVE , Winter Garden, Florida

    This beautiful, water front home has been meticulously maintained and designed with no expense... Read More

  • Home For Sale $1,775,000
    • 5Bed
    • 5.5Baths
    • 5,675Sq ft
    14628 AVENUE OF THE RUSHES , Winter...

    Gorgeous better than new custom home on lake handcock!! as you approach the home you are welcomed... Read More

  • Home For Sale $809,990
    • 5Bed
    • 3.5Baths
    • 4,907Sq ft
    17732 DEER ISLE CIR , Winter Garden, Florida

    One or more photo(s) has been virtually staged. this prestigious victorian 4 bedroom main house... Read More

  • Vacant Land For Sale $285,000
    • 0Baths
    LAKE HICKORY NUT DRIVE , Winter Garden,...

    Spectacular one-acre lakefront lot on pristine lake hickory nut, a jewel just west of disney.... Read More

  • Home For Sale $669,995
    • 4Bed
    • 3.5Baths
    • 2,853Sq ft
    8180 TOPSAIL PLACE , Winter Garden, Florida

    Under construction. the bavaro plan features a soaring two-story foyer highlighted by a grand... Read More

  • Home For Sale $609,995
    • 3Bed
    • 3Baths
    • 2,298Sq ft
    15835 SHOREBIRD LANE , Winter Garden, Florida

    Under construction. mediterranean single story home with tile roof, paver driveway, front porch,... Read More

  • Home For Sale $315,000
    • 2Bed
    • 2Baths
    • 1,265Sq ft
    14501 GROVE RESORT AVENUE #1244, Winter...

    Enjoy florida living at the grove resort & water park. this unique 4-star resort offers luxury... Read More

  • Home For Sale $1,250,000
    • 5Bed
    • 5Baths
    • 4,839Sq ft
    14604 AVENUE OF THE RUSHES , Winter...

    Independence! lakefront home with breathtaking views of lake hancock and so close to disney you... Read More

  • Vacant Land For Sale $500,000
    • 0Baths
    260 DEER ISLE DRIVE , Winter Garden, Florida

    Nestled just inside the gates of deer island, an exclusive community featuring an enclave of... Read More

  • Home For Sale $1,175,000
    • 7Bed
    • 6Baths
    • 5,141Sq ft
    16623 BROADWATER AVENUE , Winter Garden,...

    Why wait and build new when this waterfront opportunity is ready now! every amenity you need is... Read More

  • Home For Sale $296,900
    • 2Bed
    • 2Baths
    • 1,265Sq ft
    14501 GROVE RESORT AVENUE #1111, Winter...

    Zoned for short term rental. this condo offers a fully-equipped kitchen, separate living and... Read More

  • Home For Sale $1,050,000
    • 5Bed
    • 5Baths
    • 5,422Sq ft
    17800 BONNIEVISTA COURT , Winter Garden,...

    Location & lifestyle! come home to this gated island oasis boasting 1-acre min lots & surrounded... Read More

  • Home For Sale $319,900
    • 3Bed
    • 2.5Baths
    • 2,411Sq ft
    1122 HARBOR HILL STREET #1, Winter...

    Gated golf course community located just south of winter garden 15 minutes from disney this 3... Read More

  • Home For Sale $847,500
    • 6Bed
    • 5Baths
    • 4,817Sq ft
    7479 JOHN HANCOCK DRIVE , Winter Garden,...

    Upon arrival, you are greeted by this gorgeous estate home. situated on the only premium homesite... Read More

Winter Garden - Statistics and Home Trends

Learn More About Winter Garden, Florida

Currently there are 290 homes for sale, 23 condos and apartments for sale, 38 vacant land for sale and 31 townhomes for sale in Winter Garden

Learn More About Winter Garden, Florida:

Winter Garden is a mid-sized city in Orange County, Florida in the central region of the state. Located just 14 miles west of downtown Orlando, Winter Garden covers approximately 15.6 square miles of and has a population of just over 40,300. Winter Garden’s is a city that takes great pride in and goes to great lengths to preserve its local history.


Winter Garden features a warm and humid subtropical climate, which typically produces a hot and rainy season lasting from May until October and a dryer, more moderate season from November through March. The area's weather is significantly influenced by the movement of the Gulf Stream.


Winter Garden is known for its incredible parks and outdoor amenities as well as its historic preservation efforts. That’s why the signature community feature is Winter Garden is the West Orange Trail. This former rail line has ben converted into a 22 mile multi-use trail that is enjoyed by cyclists, joggers, rollerbladers, and walkers alike. It has four main stations, one of which is the historic downtown district. All four stations providing parking, restroom facilities, bike racks and drinking fountains. Bike and roller-skate rentals are available at the Killarney Station. The Chapin Station has a basketball court and tennis courts.


For those who enjoy a brush with the past, a stroll through Winter Garden’s Downtown Historic District will certainly brighten their day.  The 100-acre district features no less than 26 historic buildings providing a fascinating insight into Winter Garden’s past. In August 1996, it was added to the U.S. National Register of Historic Places.


Also key to connecting to Winter Garden’s past are the Heritage Museum and the Central Florida Railroad Museum. The Heritage Museum houses an extensive collection of over 5,000 artifacts documenting the area's past, including local citrus labels, Native American artifacts, railroad memorabilia and historic photographs. The Central Florida Railroad contains exhibits depicting Central Florida's railroading history, including a large collection of dining car china.


The cultural gem of area is the Garden Theatre widely known as Winter Garden's premier performing arts venue. First opened in 1935, the theatre was designed in the Mediterranean Revival style, with the interior of the theatre featuring Romeo & Juliet balconies, a Spanish tile roof and a dark blue ceiling resplendent with stars. After closing in 1963, the city bought it in 2002 and restored it through the efforts of the Winter Garden Heritage Foundation. After reopening in 2008, the facility has hosted some of the best plays, musicals, and live performances in the state.


Schools in Winter Garden are administered through the Orange County School District. Amongst the highest rated schools in the city are: Lake Whitney Elementary School, Bridgewater Middle School, West Orange High School, and Whispering Oak Elementary School.


Winter Garden has a well earned reputation for being a desirable place to live due to its diversity of housing options, warm charm, great schools, and one of the lowest millage rates in Orange County. All of which adds up to a superior quality of life for those who call it home. offers For Sale By Owner listing services throughout the country. By posting home with ByOwner your property will get the same exposure you’d receive from a traditional real estate company. Our Winter Garden, Florida Flat Fee MLS listing Service saves you from paying the traditional 6% commission charged by most real estate offices, but gives you the same worldwide exposure.

Your home will be found on the local MLS, plus all the major search engines and popular real estate portal sites, including: Trulia, Zillow,, MSN, AOL, Bing, Yahoo, and of course Google. Additionally when your home gets added to the MLS, your FSBO listing will listed alongside of the homes listed by ReMax, C-21, Coldwell Banker, ERA, Redfin, Movoto, Keller Williams and all the other nationwide brokerage sites. These sites often display “all” of the MLS postings, not just their own, which means your home will be on these sites also.

The average seller who uses our Flat Rate MLS Listing, will save over $15,000. We give you the tools and exposure you need as a ForSaleByOwner to compete with every other listing in the MLS. But you are in control of the savings and the fees you pay.

Currently Winter Garden has 385 properties on the market for sale. The inventory was last updated 01/20/2020. Of these properties, 290 single family homes are for sale by their owners in Winter Garden, and 23 condos are for sale by their owners in Winter Garden. The average price of the single family homes for sale in Winter Garden, is $482,113, the average condo price in Winter Garden, is $385,714. The average price per square foot of the active inventory is $152. This is based the living area square footage.

Over the last year, there have been 10,191 of properties sold in Winter Garden. Of these properties, 8,197 single family homes have sold by their owners in Winter Garden, and 374 condos have sold by their owners in Winter Garden. The average sales price of the single family homes sold in Winter Garden, is $325,262. Single family homes have been selling for 140 per square foot of living area. The average sales price of the condos for sale in Winter Garden, is $251,639. Condos have been selling for 110 per square foot of living area.

The most active subdivisions with listings for sale in Winter Garden, are: Watermark (18 For Sale), Hamilton Gardens (12 For Sale), Mcallister Landing (9 For Sale), Mcallister Landing Phase 2 (9 For Sale), Stoneybrook West 44134 (7 For Sale), Lakeshore Preserve (6 For Sale), Twinwaters (5 For Sale), Stoneybrook West (5 For Sale), Overlook At Hamlin (5 For Sale), Signature Lakes Ph 02 A B H I J (4 For Sale)

If you are thinking of selling your Winter Garden home, try our flat fee listing service, Our list fees start at $449, and may save you $15,000 in real estate commissions. Click here to start saving.

Disclaimer: Listing broker has attempted to offer accurate data, but buyers/lessees are advised to confirm all information IDX information is provided exclusively for consumers' personal, non-commercial use that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that data is deemed reliable but is not guaranteed accurate by the MLS. The MLS may, at its discretion, require use of other disclaimers as necessary to protect Participants and/or the MLS from liability.
This data up-to-date as of 01/20/2020