Winston Trails

In This Community

19 homes for sale

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Buyers of homes for sale in the prestigious community of Winston Trails connect to the country club lifestyle without mandatory membership. In other words, enjoying spectacular views of waterways crisscrossing undulating green fairways and integrating with South Florida’s exotic plants, indigenous trees, and wildlife doesn’t cost them an arm and a leg. The developers tackled the gated golf community landscape ambitiously, constructing just over 1,900 single family homes and villas in eighteen architecturally distinctive villages ranging from 1,300 to 4,000 square feet. Most Winston Trails real estate listings entering the MLS reflect vintages in the mid to late 1990s.
 
Of course, the proximity of the semi-private golf facility is ideal for those living on campus who want to participate in the amenities. The latter includes a meticulously manicured championship golf course (with a driving range and practice chipping & putting green), two heated swimming pools, tennis courts and pickleball courts, and a state of the art fitness center with saunas. Please note that non-equity family membership fees are less than $700 per month, and the monthly HOA for all residents (mandatory fee members or not) enjoying the country club environment, gated security, and multiple nature trails is a lowly $205.

Winston Trails Homes For Sale

Reduced

$1,199,999

$1,300,000

MLS#RX-11127618

6405 Shadow Creek Village Cir
Lake Worth, FL 33463

4

3

2

2,977 SqFt

Pool

105 Days

$949,995

MLS#RX-11135008

6374 Old Medinah Cir
Lake Worth, FL 33463

4

3

2

2,986 SqFt

Pool

79 Days

$829,000

MLS#AX-11919707

6758 Lake Nona Pl
Lake Worth, FL 33463

4

3

2

3,204 SqFt

0.167 Acres

47 Days

$817,000

MLS#RX-11116749

6283 Shadow Tree Ln
Lake Worth, FL 33463

5

3

3

3,722 SqFt

Pool

Water Front

0.18 Acres

145 Days

Under Contract

$779,000

MLS#RX-11134971

5609 Lake Shore Village Cir
Lake Worth, FL 33463

4

3

2

3,267 SqFt

Pool

Water Front

0.29 Acres

2 Days

Reduced

$753,000

$800,000

MLS#RX-11131114

6394 Sand Hills Cir
Lake Worth, FL 33463

5

3

2

3,204 SqFt

Pool

0.17 Acres

93 Days

$729,900

MLS#RX-11145002

6206 Indian Forest Cir
Lake Worth, FL 33463

4

3

2

9,904 SqFt

Water Front

0.23 Acres

39 Days

Reduced

$705,000

$790,000

MLS#RX-11088064

5349 Oakmont Village Cir
Lake Worth, FL 33463

4

3

2

2,977 SqFt

0.17 Acres

237 Days

Under Contract

$639,900

MLS#RX-11130971

6346 Sand Hills Cir
Lake Worth, FL 33463

4

2

2

2,426 SqFt

Pool

0.17 Acres

134 Days

Reduced

$637,500

$657,000

MLS#RX-11099628

6380 Bridgeport Ln
Lake Worth, FL 33463

4

3

2

3,168 SqFt

0.18 Acres

659 Days

$637,000

MLS#RX-11146690

6220 Barton Creek Cir
Lake Worth, FL 33463

3

3

2

2,463 SqFt

Pool

Water Front

0.13 Acres

32 Days

Under Contract

$600,000

MLS#FX-10538628

6329 Hatteras Club Drive
Lake Worth, FL 33463

3

2

2

2,672 SqFt

Water Front

0.18 Acres

17 Days

19 Active Listings in Winston Trails

Prospects interested in extremely desirable Winston Trails discover a considerable difference in residence features for one primary reason: some homeowners have significantly upgraded original developer handovers, while others have added little. Remodeling, when evident, delivers from an extensive list that covers replaced roofs, new air-con systems, and high-impact windows and sliders; also, modern marble, graphite, and imported wood materials on flooring, sleek cabinetry, and countertops.

Winston Trails residents leave the neighborhood, exiting on Jog Road on the western border or Hypoluxo flanking it to the south, a central city position. In twenty minutes or less, they can be:

• Sitting on white sand beautiful beaches east of the A1A.
• Undocking a yacht on the Intracoastal.
• Eating at one of the multiple restaurants in the vicinity.
• Enjoying the many parks, nature preserves, upscale retail outlets, and non-stop Atlantic Avenue action in downtown Delray Beach close by.
• Accessing every expected metropolitan convenience, from supermarkets to clinics, banks, nail salons, good schools (see below), and gas stations via short drives in all directions. 
• Transitioning fast and seamlessly to two international airports via the I95 or Florida’s Turnpike 

All the above makes Winston Trails in Lake Worth the ideal 18 hole golf course community for a rustic lifestyle with big-city conveniences.

South Florida is famous for country club options, equity, and non-equity. Therefore, our data shows that Winston Trails buyers also looked at Boca Pointe, Boca Greens, Delaire Country Club, Gleneagles, Aberdeen Country Club, and Hunters Run, representing the best values in the two country club categories.

Winston Trails Community Summary

Winston Trails is a gated community of single family homes in Lake Worth, Florida, with a range of options priced between $450,000 and $1,199,999. There are currently a total of 19 homes for sale in Winston Trails. The smallest Winston Trails home presently available is a three bedroom two bathroom residence that is 1,638 square feet (1,336SF Under Air living space), and the largest of the Winston Trails homes currently on the market has five beds and three baths and is a 9,904 square foot (2,673SF Under Air) residence.

The Winston Trails community offers a plethora of amenities for its residents to enjoy, including a clubhouse, swimming pool, spa / hot tub, cabana, a state-of-the-art fitness center, sauna, game room, billiards room, and business center. Sports facilities include a championship golf course, a putting green, tennis courts, pickleball courts, Bocce ball, racquetball, basketball court, and shuffleboard. Onsite dining venues consist of a restaurant, and a picnic area. There is also a community park, a playground, as well as walking or jogging trails.

The Winston Trails HOA rules do allow homeowners to have pets although there are certain breed restrictions. There is a limit of how many pets you may have, and there is a restriction on pet size.

The floor plans in Winston Trails are among several home models such as the Antigua, Antilles, Aspen, Athens, Bimini, Cairo, Capri 2, Capri Ii, Cario, Casablanca, Copenhagen, Domenica, Doral, Extended Venice, Fairport, Grandview, Hatteras, Inverness, Lexington, Lisbon, London, Monaco, Montreal, Nairobi, Nassau, Oslo, Paris, Princeton, Richmond, Rio Grande, Riviera, Santa Cruz, Sapporo, Sydney, The Venice, The Washington, The Willow, Venice, Washington, Willow, and the Woodhall.

There are two commercial airports that serve Winston Trails - Palm Beach International Airport (PBI), which is eight miles away, and Fort Lauderdale Hollywood International Airport (FLL), which is 35 miles away.

Winston Trails real estate activity on the Lake Worth MLS during the past year (as of January 2026) reflects 111 homes changing hands, with an average asking price of $624,561 and an average selling price of $601,158. This represents a healthy list-to-sell price ratio of 96% and $225 per square foot. During this period, Winston Trails homes for sale have taken an average of 52 days to sell.

In addition, there are numerous other communities in Lake Worth to choose from, or you may browse all available Lake Worth Real Estate, including some new construction opportunities. Homes for sale in Winston Trails are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Winston Trails hits the market. You can also always contact your ZFC Real Estate agent, who would happily assist you further with all your South Florida real estate needs.

The data relating to homes for sale or lease or other real estate for sale or for rent on the ZFC website comes in part from a cooperative data exchange program of the MLS in which this Broker participates. The real estate displayed may not be all of the homes in the database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Homes for sale that are listed by Brokers other than this Broker are marked with either the listing Broker's name or the MLS name or a logo provided by the MLS and the details page about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. ZFC, the Florida Association of Realtors and its cooperating Multiple Listing Services do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law including the fair housing act prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. All properties featuring the Miami Realtors logo are provided by the Miami Association of Realtors. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.