$614,668Average Value$290Average Price per Sq Ft21Homes For Sale
Entrance to the Winston Trails Country Club.
Walkability and recreation in a gated community
Winston Trails is a luxurious gated community in South Florida that’s aptly named. The neighborhood has a 2-mile-long walking trail that winds through palm-tree-lined streets and lush Florida landscaping. “It’s great for people who like to ride their bikes or walk their dogs,” says Lois Rutigliano, global advisor at One Sotheby’s with experience in the area. “You can go for a long walk without having to get on a main street.” Residents enjoy views of glistening lakes and the 18-hole golf course from their Spanish-styled homes. Numerous commercial centers nearby and access to highly rated public schools have attracted families in recent years. “It’s a very family-oriented place,” Rutigliano says. Commuters are well-connected to the surrounding areas, with Downtown West Palm Beach just 18 miles away.
Houses line the Winston Trails Golf Course.
Winston Trails Golf Club anchors recreation
Residents who join the Winston Trails Golf Club have access to the classic country club amenities, including an Olympic-sized swimming pool and six tennis courts. The 18-hole golf course spans 7000 yards of lush, manicured fairways and champion Bermuda grass-putting greens. Beyond the gates, Buttonwood Park is nearby and features fully lighted sports fields and basketball courts. Indoor recreation is anchored by West Boynton Parks and Recreation Center, while beach days can always be found at the lapping shores of Lantana Municipal Beach, under 9 miles away.
Rows of houses in Winston Trails showcase a blend of modern and classic architecture.
Spanish-style homes on palm tree-lined streets
Winston Trail’s housing consists of 1891 single-family homes scattered throughout 18 subdivisions. Spanish-revival architecture is the predominant style, and most residences feature pastel-colored stucco exteriors with red-tiled roofs. Palm trees shade the well-manicured front lawns, while backyard swimming pools provide a great place to cool off. Prices range from $500,000 to $850,000, depending on the number of bedrooms and lot sizes. The Winston Trails Golf Club does not have a mandatory membership for residents, though individual subdivisions do have HOAs. The area is prone to hurricanes, but the neighborhood’s inland location provides protection against stronger storms.
Park Vista Community High School
Highly rated Palm Beach County Public Schools
The highly rated Palm Beach County School District serves the neighborhood. Manatee Elementary and Christa McAuliffe Middle School both received an A-minus rating. Students can enroll in Christa McAuliffe’s Information Communication Technology Academy, which emphasizes college preparatory curriculum linked to a direct career in IT. The A-rated Park Vista Community High School offers students multiple in-house academies ranging from medical sciences to information technology. The digital media program encourages participants to become proficient in industry-standard technologies and techniques to create original work. Trinity Christian Academy is an A-rated private school option for parents to consider.
Local eateries and live music
Winston’s on The Green is a popular local eatery conveniently located in the middle of the neighborhood. As the name suggests, the restaurant has picturesque golf course views and features live music every Friday and Saturday night. The community is close to a host of shopping and dining areas nearby. “It's pretty commercialized out there,” Rutigliano says. “There’s quite a few chains but also lots of smaller mom-and-pop kind of places.” One of these establishments includes Chris’ Taverna, a family-owned and operated Greek restaurant that serves classic Mediterranean-style dishes. Eggs-Cetera Café is next door and features tasty breakfast creations. Winn-Dixie and Publix Super Market provide the neighborhood with fresh produce and weekly groceries. More extensive retail can be found at Boynton Beach Mall, 7 miles away. HCA Florida JFK Hospital is one of many medical facilities in the area.
Community events with city-wide celebrations nearby
The neighborhood hosts numerous community events throughout the year, ranging from major golf tournaments to back-to-school supply drives. Live music acts are common at Winston’s on the Green, and tickets are sometimes required for popular performers. Residents are also close to celebrations put on by the City of Lake Worth. Downtown Lake Worth is transformed during the Annual Street Painting Festival, where over 600 artists turn the streets into a temporary collection of original art and masterpiece reproductions. The creative exhibition is popular for local artists and art school field trips, and the colorful collections last only until the next rain.
Easy access to the 95 from Winston Trails.
Catch a ride on The PalmTran
Winston Trails is highly walkable, but those traveling farther will find they are well connected to South Florida. Residents are 18 miles from downtown West Palm Beach and 14 miles from Palm Beach International Airport. The Palm Tran is a public transit bus system that services many stops along Lantana Road, which runs parallel to the community.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
Are you familiar with the Winston Trails neighborhood?
to let others know what life in this neighborhood is like.
Crime and Safety
1 - Low Crime, 10 - High Crime
Winston Trails
US
Homicide
1
4
Sexual Assault
2
4
Assault with Weapon
3
4
Robbery
3
4
Burglary
4
4
Motor Vehicle Theft
3
4
Larceny
2
4
Crime Score
2
4
Source: WhatIsMyCrimeRisk.com
Winston Trails Demographics and Home Trends
On average, homes in Winston Trails, West Palm Beach sell after 45 days on the market compared to the national average of 55 days. The median sale price for homes in Winston Trails, West Palm Beach over the last 12 months is $585,000, down 4% from the median home sale price over the previous 12 months.
Fall in love with this magnificent 5 bedroom, 3 bath inground spa pool home, where elegance and sophistication meet thoughtful design and high end improvements. Every detail of this residence has been curated to blend style, comfort, and functionality, creating a truly exceptional living experience. The hear of the home is the renovated kitchen, featuring updated cabinets with granite
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 rear neighbors and ideal south exposure, this light-filled residence offers both privacy and elegance. The home features a designer kitchen (2018) and beautifully updated bathrooms (2019), major upgrades including roof (2021),
Welcome to your dream home in the highly sought-after Winston Trails! Located in the desirable Sand Hills Village subdivision, this beautifully updated 3-bedroom, 2-bath pool home offers over 1,900 sq. ft. of living space on a 0.18-acre lot. Step inside and experience the thoughtfully designed Copenhagen floor plan, enhanced with stylish modern updates throughout. The spacious formal living and
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 beautifully remodeled 4-bedroom, 2.5-bath pool home with a private den/office offers the perfect blend of comfort, style, and functionality. Situated on an oversized lot, the backyard is a true retreat—fully fenced with a lush Clusia
Beautifully updated 4-bedroom, 2.5-bath home featuring a private screened-in pool and spacious outdoor living area, perfect for enjoying the Florida lifestyle. This well-maintained property includes a new roof and fully renovated pool (2025), along with a heated pool system and a newly tiled patio, creating a modern and inviting outdoor space ideal for entertaining. The screened-in enclosure,
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 is designed for both comfort and entertaining, featuring a beautifully maintained saltwater pool set on a paved patio with endless outdoor living possibilities. The home is in excellent condition, showcasing neutral tile and
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 exposure. Additional features include recently painted living areas, hurricane panel protection, a large driveway, and an extended 2-car garage with an additional 4 feet of depth, allowing space for a full-size pickup truck. Winston
Stunning builder's model home located in the beautiful community of Winston Trails! This spacious 2-story lakefront pool home features 3 bedrooms plus a Den/ loft, 2.5 bathrooms, and a 2-car garage, perfectly positioned overlooking the long end of the lake for peaceful water views. Move-in ready and meticulously maintained, the home features a brand-new roof and has been freshly painted inside
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 Trails community, where comfort, space, and lifestyle come together effortlessly. From the moment you arrive, you'll feel the pride of ownership and the inviting atmosphere that makes this house truly feel like home. Inside, you're
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 roof and exterior paint (2021), plus a modernized interior featuring a remodeled kitchen, updated first-floor guest bath, new flooring, and upgraded stair railing -- all less than two years old. The home also includes newer
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 ROOM is perfectly positioned on expansive lake + fairway views, offering soaring ceilings, light-filled open layout. Renovated kitchen features modern finishes, double oven, generous prep space, flows seamlessly into the main living
*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!*Brand New Roof Jan 2026!*Brand New AC Jan 2026!*New Wtr Htr!*Beautifully Updated Master Bathroom With An Oversized Soaking Tub, Dual Sinks & Closet Built Ins!*You Have A True Living Room, Separate Family Room, Formal Dining Room
Welcome to this charming 3 bedroom, 2 bathroom single-family home located on a desirable corner lot in the sought after Winston Trails community. This well maintained residence offers a spacious and functional layout, perfect for comfortable everyday living and entertaining. Enjoy abundant natural light throughout the home, along with generously sized bedrooms and a primary suite featuring a
Beautiful 3 bedrooms, 2.5 Baths, 2 cars garage in a desirable Neighborhood,Spacious and well-maintained 2-story home located in Strawberry Lakes community. This bright and airy residence features an open layout, wood flooring upstairs, and tile flooring on the main level. New kitchen with quartz countertops and cabinets, stainless-steel appliances, New Bathrooms and fresh paint the entire house.
Welcome to this beautiful and bright home for 3 BR / 2 full BAin Winston Trails, a very nice Gated Community neighborhood, 24hs security. 2 cars garage. Freshly painted home, plenty storage space, walk in closet. Tiled and laminated floor. Granite countertop. New stainless-steel appliances. New yard fences. Rent includes Association Dues, Trash removal, Basic Cable, High Speed Internet and
Spacious and well-maintained 2-story home located in the desirable Strawberry Lakes community. This bright and airy residence features an open layout, wood flooring upstairs, and tile flooring on the main level. Updated kitchen with granite countertops, ample cabinet space, and stainless-steel appliances. Generously sized bedrooms with plenty of natural light and closet space. Enjoy a private,
Local Logic measures the walkability, access to public transit and bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
