![]()
The Winston Trails community in Lake Worth, Florida is a meticulously maintained guard gated, golf course community for family members of all ages. Here you can enjoy the country club atmosphere and amenities without the country club expenses. After a rousing round of golf, you and your friends can sit and enjoy a relaxing cocktail in beautiful surroundings at the full service restaurant. Not a golfer? Why not enjoy, the tennis courts, swimming pools, exercise room or saunas. The Winston Trails community consists of over 1900 single family homes and villas, many with golf course views. Its central and convenient location puts you within arm's reach of the best of Palm Beach County with quick and easy access to both I-95 and the Turnpike. Winston Trails is conveniently located on the East side of Jog Road between Lantana and Hypoluxo. Click on a listing to view the property details, photos and agent comments. If you would like to change or expand your search criteria, go back to the main Lake Worth FL Real Estate page, or try using our Advanced Search.
Located in the gated community of Winston Trails, this spacious 3-bedroom, 2-bath CBS home features a desirable split-bedroom floorplan with soaring vaulted ceilings, abu...
Exceptional opportunity to own this 3-bedroom, 2-bath residence situated on a desirable corner lot in the highly sought-after Winston Trails Golf Community, featuring top...
LAKEFRONT POOL HOME WITH NEW ROOF & SPECTACULAR WATER VIEWS! Enjoy the best of Florida living in this spacious 3-bedroom plus loft/den, 2.5-bath, 2-car garage home, ideal...
Welcome to this beautifully updated Venice model pool home in the highly sought-after Winston Trails community. Featuring a desirable split-bedroom ranch floor plan, this...
Meticulously maintained 3BR/2BA home in a desirable gated community featuring a NEW ROOF (2025), IMPACT WINDOWS, A/C (2023), NEW GARAGE DOOR OPENER (2023), NEW POOL HEATE...
Rare opportunity to own this beautifully renovated 4-bedroom, 2.5-bath pool home in the highly sought-after Winston Trails Golf Community, offering top-rated "A" schools ...
LOCATION! LOCATION! LOCATION! This sought after community is waiting for you. Perfectly positioned on the 15th hole, this beautifully updated pool home offers peaceful v...
Welcome to your dream home in Winston Trails! Located in the desirable Las Colinas Village, this beautifully maintained 3-bedroom, 2-bathroom Cairo model offers breathtak...
Welcome home to this beautifully updated 4-bedroom, 2.5-bath pool home located in the highly desirable gated Bay Hill Village subdivision of Winston Trails. Situated on a...
Welcome to this beautifully maintained Nairobi model located in the highly desirable gated community of Winston Trails, within the Prairie Dunes Village subdivision. Th...
Welcome to this beautifully maintained 3-bedroom, 2-bathroom home located in the highly sought-after gated community of Winston Trails. Thoughtfully updated and move-in r...
Welcome to this beautifully renovated 4-bedroom, 2.5-bath lakefront home in the highly sought-after community of Winston Trails. Perfectly situated on a serene waterfront...
Welcome to your own slice of paradise with this beautifully cared for Paris model that offers an expansive view of the lake and golf course, and a thoughtful blend of com...
Welcome to 6244 Grand Cypress Circle, nestled in one of Palm Beach County's most established gated, non-equity golf communities — Winston Trails! This beautifully mainta...
Welcome to the highly sought-after gated community of Winston Trails in the desirable Barton Creek Village subdivision! This bright and beautifully maintained Nairobi mod...
Set within the highly sought-after gated golf community of Winston Trails Golf Club, this exceptional Paris model combines luxury, privacy, and resort-style living in one...
Welcome to 6292 Grand Cypress Circle, nestled in one of Palm Beach County's most established gated, non-equity golf communities—Winston Trails! This beautifully maintaine...
This beautiful home qualifies for a Lender specific $10k Buyer Credit! Welcome to Shadow Tree Lane nestled on a quiet cul-de-sac in the the highly desirable community, ...
A BRAND NEW ROOF!!! Welcome to one of the best opportunities in Winston Trails Community! Step into this beautifully maintained home in the highly desirable Winston Trail...
LAKEFRONT, GOLF COURSE, POOL HOME in one of Palm Beach County’s most established golf communities, Winston Trails. This meticulously maintained 3-bedroom home + BONUS ROO...
Welcome to your dream home in the highly sought-after gated community of Winston Trails in the Bay Meadow Village subdivision! This bright and beautifully updated Fairfax...
Rare extended Sydney model located in the only separately gated section of Winston Trails -- beautifully updated and truly move-in ready! Enjoy peace of mind with a newer...
Experience the best of both worlds on this premium lot with stunning water views in the front and picturesque golf course vistas in the back! This 3-bedroom (+ Loft), 2.5...
Welcome to 5053 Prairie Dunes Village Circle, located in the gated, non-equity golf community of Winston Trails in the desirable Prairie Dunes subdivision. This beautifu...
Nestled in the highly sought-after community of Winston Trails, this exceptional home sits on a large, beautifully maintained lot that offers both space and serenity. Sur...
Welcome to a beautiful waterfront home tucked within the desirable Winston Trails community of Lake Worth. This 4-bedroom, 2.5-bath residence captures the best of Florida...
Welcome to this beautifully maintained 3-bedroom, 2-bathroom single-story home located in the highly sought-after community of Winston Trails. Nestled in a gated, golf co...
Luxurious 5-bedroom, 3-bathroom pool home offering over $155,000 in upgrades, designed for both comfort and functionality. Situated on a beautifully landscaped lot, the p...
Exquisitely remodeled 3BR/2BA home in the prestigious guard-gated community of Winston Trails with A-rated schools. Perfectly positioned lot backing the 18th tee with no ...
New Roof installed 2026. Enjoy outdoor living with a screened covered patio and private pool overlooking peaceful lake and golf course views with desirable southern expos...
Welcome home to this magnificent 5-bedroom, 3-bathroom two-story home, perfectly located on a cul-de-sac and and situated on an oversized, fully fenced lot. This property...
Located within the guard-gated Winston Trails community, this well-appointed 3-bedroom, 2-bath single-family residence offers 1,336 sq ft of comfortable, thoughtfully des...
*Nothing Left To do In This Gorgeous 1 story Estate Home!*Split Plan With 4 Large Bedrooms and 2 Full Baths*Tile Throughout Living Areas & New Laminate In The Bedrooms!*B...
SELLER SAYS BRING ALL REASONABLE OFFERS. Here's your own slice of paradise - this stunning beautifully cared and HARDLY LIVED IN, as this was a 2nd home for the sellers,...
This impeccably Willow model offers 4 bedrooms plus a loft and 3 full baths, ideally positioned on a premium lakefront lot showcasing breathtaking long-lake views and unf...
Welcome to this beautifully updated, meticulously maintained residence located in the highly sought-after gated golf community of Winston Trails. Situated on an oversized...
Corner Lot! Beautiful Pool and Lakefront View. Porcelain and Bamboo Floors. Upgraded kitchen from top to bottom, with Honey Maple Cabinets, Crown Molding, with Pantry and...
Truly remarkable and spacious lakefront home on a premium lot with private backyard. Large, screen enclosed pool and over 300 sq. ft. of roof covered lanai that feels lik...
Welcome to Winston Trails! Where this beautiful 4 bedroom, 2.5 bath home is available. Light and bright this updated property has everything you could want from fully re...
Welcome to your dream home in the highly sought-after Winston Trails! Located in the desirable Shadow Creek Village subdivision, this beautifully updated 4-bedroom, 3-bat...
Step into this fully renovated, move-in-ready home located within the highly sought-after, gated community of Winston Trails, known for its A-rated schools and an excepti...
Welcome to Winston Trails, a resort style community with a manned gate - conveniently zoned for all A rated schools such as Manatee Elem, Crista McAuliff Middle and Park ...
Prepare to be amazed by this stunning, fully remodeled two-story residence, offering four spacious bedrooms, three beautifully updated baths, and an additional den/office...
Welcome to this beautifully upgraded 5-bedroom, 3-bath Paris Model in the highly sought-after Winston Trails community—renowned for its top-rated schools and resort-style...
Discover refined living in the guard-gated golf community of Winston Trails. This 3-bedroom, 2.5-bath single-family residence with a one-car garage offers a well-designed...
Lakefront Living in Winston Trails! This beautifully updated 3-bed, 2.5-bath single-family home offers 1,622 sq ft & open-concept living with soaring ceilings & stunning ...
Welcome to the highly sought-after community of Winston Trails, renowned for its A-rated schools, beautifully maintained landscaping, and unmatched lifestyle amenities! ...
Welcome to this beautiful two-story home, offering 3 spacious bedrooms and 2.5 bathrooms,1 car garage ,perfect for families .Nestled in a desirable neighborhood, this hou...
NEW ROOF - WOW! Discover this beautifully renovated single-story home in exclusive Winston Trails, offering privacy with no front or rear neighbors! Enjoy serene golf c...
Welcome to Winston Trails’ Catalina on the Green, a gated community where this beautifully maintained lakefront home offers comfort, style, & long-term peace of mind. Not...
A tropical oasis awaits you! This is the Sydney model POOL HOME which is situated on oversized, 1/3 of a acre lot that boasts 4 bedrooms plus and office/workout room adja...
Welcome to 6219 Grand Cypress Circle — Your Dream Home Awaits in Winston Trails! Step into comfort, style, and Florida living at its finest in this Cairo model, ideall...
SELLER IS MOTIVATED! Buyer couldn't wait for probate to finish in the courts—so their loss is your gain! Listing includes virtually staged photos. Welcome to this meti...
Welcome to this beautiful 4 bedroom, 2 bath single-family pool home in the highly desirable Winston Trails community! This home features tile flooring throughout, a kitch...
Priced to sell!. Welcome Home! Bring us an offer! Resort Style Pool home 4 bedrooms, 3 full bathrooms and a loft that can be converted into a fifth bedroom, soaring ceili...
Beautifully maintained Antilles model single-story home in the desirable gated Winston Trails community, lovingly cared for by its original owner. This bright and spaciou...
Perfectly positioned on a quiet cul-de-sac and situated on one of the few lots in the neighborhood that spans over a quarter of an acre, this stunning one-story ranch-sty...
Welcome to your dream home in the highly sought-after Winston Trails! Located in the desirable Shadow Creek Village subdivision, this beautifully updated 4BR, 2.5BA pool ...
Stunning spacious 5 Bedroom, 3 Bath Pool Home in Prestigious Gated Golf Community (No Mandatory Membership!) Welcome to your dream home! This beautifully updated 2-story...
Welcome to this beautifully updated pool home with a new roof on an oversized lot located in the highly sought-after community of Winston Trails. Thoughtfully designed wi...
Move in Ready 3 Bedroom 2 Bathroom with den area! Stunning floors throughout the bedrooms, Gated community and Association dues include lawn/Landscape, trash and pool mai...
Fantastic Ownership Opportunity! This beautiful 3-bedroom, 2-bathroom single-story home with a 2-car garage is ready for its new proud owner. The open and split floor pla...
Waterfront Home with Golf Views in Winston Trails-This 3/2 waterfront residence in Newport Village offers comfortable living w/vaulted ceilings & an open-concept design c...
Welcome home to your dream home in the desired, gated community of Winston Trails! Located in the Indianwood Village subdivision, this beautifully updated Casablanca mode...
Welcome to this beautifully maintained one-story waterfront home featuring 3 bedrooms, 2 baths, a brand-new roof, and about a 3-year-old AC system for peace of mind and c...
None
© 2026 Georgia MLS. All rights reserved. Information Deemed Reliable But Not Guaranteed.
Listings on this website come from the FMLS IDX Compilation and may be held by brokerage firms other than the owner of this website. The listing brokerage is identified in any listing details. Information is deemed reliable but is not guaranteed. If you believe any FMLS listing contains material that infringes your copyrighted work, please click here to review our DMCA policy and learn how to submit a takedown request. © 2026 FMLS. Last updated