Water, water everywhere and more than you might think
Winter Haven is the midpoint between Tampa and Orlando in rapidly growing Polk County. Known for having dozens of lakes, this outdoor paradise has experienced significant growth in recent years, reaching 60,000 in 2024. For years the city was a popular destination for snowbirds seeking a second home and empty-nesters relocating from up north, but a younger demographic is driving the current growth. Fitting for a city that offers year-round outdoor adventures, is home to Legoland theme park and has a buzzy downtown with a burgeoning contemporary dining and entertainment scene. “Over the last 15 years, we have gotten a lot younger,” says Kim Davis, a Realtor with Crosby & Associates and city resident. “We now have a very large population of adults between 25 and 50. We’re definitely growing in the family-producing age group. Thirty years ago, Winter Haven was basically a 55-plus community with a few families, but it has really flipped.”
Whether you arrive by boat or car Tanners Lakeside is a waterfront hangout in Winter Haven, FL.
For a fun adventure, Legoland is a great family theme park in Winter Haven, FL.
Downtown Winter Haven is the vibrant centerpiece of one of Florida’s fastest-growing cities.
Downtown Winter Haven is full of vibrant works of art on the side of historical buildings.
The Social Cocktail Lounge features a speakeasy-style atmosphere with great cocktail options.
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Housing prices have leveled off; residential options are wide-ranging
The median sales price of $300,000 represents a $30,000 decrease from the market’s peak in August 2022. Residential options occupy a vast spectrum, from manufactured homes to waterfront mansions. Traditional ranch-style homes anchor the city’s established single-family housing. New construction comprises a collection of contemporary custom homes in traditional subdivision settings and gated and/or age-restricted communities.
Waterfront housing is ubiquitous, regardless of size or style. Manufactured homes can be found for as low as $20,000, while single-family homes typically range from around $200,000 to $1 million-plus. “There are extremes in either direction,” Davis says, “but the general single-family home is going be priced between about $250,000 and $450,000.” Condominiums and townhouses range from $100,000 to the high $300,000s. Flooding is rarely an issue in Central Florida, but insurance rates can be affected by a high risk of wind damage during hurricane season.
Gated 55+ communities of manufactured homes offer great price points for retiree's.
Waterfront housing is ubiquitous, regardless of size or style in Winter Haven.
Traditional ranch-style homes anchor the city’s established single-family homes.
New construction comprises a collection of custom homes in traditional subdivisions.
Condominiums and townhouses in Winter Haven range from $100,000 to the high $300,000s
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Dozens of lakes provide an array of recreational options
Winter Haven residents have easy access to more than 6,000 acres of lakes within the city limits. Lake Eloise is the largest at more than 1,100 acres. These bodies of water are connected by canals, making the city a haven for water recreation. “I think people appreciate the lakes, but they don’t quite realize what we have here,” says Sara Beth Wyatt, president and CEO of the Winter Haven Chamber of Commerce. “You could jump in a boat and travel from southeast Winter Haven to northwest Winter Haven quicker than you could drive.
Most lakes in Winter Haven have public access, and the city has done a great job maintaining them. We have a lakeside lifestyle that you don’t often find.” The city also offers 13 miles of multi-use trails, and its parks feature recreational spaces for athletic activities that range from baseball to pickleball. Destinations of note include Winter Haven Recreational & Cultural Center, Winter Haven Skate Park and Willowbrook Golf Course, one of the many options for golfers in and around the city.
Winter Haven residents have easy access to more than 6,000 acres of connected lakes.
Boating on Lake Summit is a common weekly attraction.
Traverse scenic wooded trails at Lake Region Audubon Nature Preserve.
Local youth love the large Winter Haven Skate Park to practice their boarding skills.
Willowbrook GC offers a championship level course for the residents of Winter Haven.
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Nutwood, Arabella's are highlights of a diverse dining scene
The city’s culinary scene is refreshingly eclectic, highlighted by a concentration of highly rated options downtown. Nutwood, owned by Michelin star-rated chef Steven Rojas, is a premier farm-to-table restaurant. Arabella’s is an upscale Italian restaurant that is a Central Florida favorite. Elevated comfort food and barbecue are among the other dining highlights. “We had a development group come here about 10 years ago. They bought up a lot of the land and totally rejuvenated downtown,” Davis says. “It’s a walkable area with restaurants and shops.” Dockside dining is available at well-known seafood restaurants outside of downtown. The city is served by two primary commercial corridors -- U.S. Route 17, known locally as 3rd Street, and Cypress Gardens Boulevard. Both are home to shopping centers, big-box retailers and grocery stores.
A burgeoning contemporary dining scene. Historic venues. Downtown Winter Haven has it all.
Nutwood, is an intimate farm-to-table restaurant located in Downtown Winter Haven
Arabella’s, an upscale Italian favorite, highlight the eclectic offerings of Winter Haven.
Harborside is a popular dockside eatery serving up fresh seafood and other favorites.
U.S. Route 17, known locally as 3rd Street is one of Winter Havens main retail corridors.
Winter Havens big-box retailers such as Lowe's can be found along its comercial corridors.
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Legoland, downtown entertainment venues are top attractions
More than just a popular vacation destination, Legoland Florida offers colorful, family-friendly fun. The latest addition to the sprawling complex is a theme park dedicated to Peppa Pig. “Locals buy passes if they have small children,” Davis says, “because there’s also a water park attached to it.” As Legoland expanded, it took over Cypress Gardens, Florida’s oldest theme park. The meticulously landscaped grounds are a botanical extravaganza on the shores of Lake Eloise.
In addition, the Cypress Gardens Water Ski team has been performing exhibitions since the 1940s, thus the city’s label as “Water Ski Capital of the World.” More traditional cultural attractions are found downtown. Theatre Winter Haven is home to popular community theater productions, and the Historic Ritz Theatre, established in 1925, features movies, concerts and improv comedy acts. Gram Parsons Derry Down is a contemporary concert venue with connections to the Winter Haven native whose “Cosmic American music” is considered the precursor to alternative country. The downtown area also hosts citywide events throughout the year. Annual celebrations include Taste of Winter Haven, Craft Beer Crawl and family friendly gatherings such as CommunityFest and Bark in the Park.
More than just a popular vacation destination, Legoland Florida offers colorful, family fun.
The World Famous Cypress Gardens Ski Team continues with monthly shows in Winter Haven.
Located in the heart of Downtown Winter Haven is the Historic Ritz Theater.
Gram Parsons Derry Downs is an event venue in Downtown Winter Haven, FL.
Community Fest is a family friendly event that encourages the community to come together
A favorite of the Bark in the Park event is the annual wiener dog race.
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Chain of Lakes Collegiate High is an A-rated Polk County school
Students are served by the Polk County Public Schools, a B-rated district by Niche that offers school choice. In 2018, in conjunction with the Polk County Sheriff’s Office, PCPS implemented one of the country’s first school safety guardian programs, which placed a law enforcement officer or armed district employee on every campus. The city’s top-rated institution is Chain of Lakes Collegiate High, a charter school for high-performing juniors and seniors that earns an A from Niche. High school and college courses are taken simultaneously at the school, which is located on the Winter Haven campus of Polk State College.
Fred G. Garner Elementary School is a public school located in Winter Haven, FL.
Jewett School of the Arts is a magnet school focused on STEAM, emphasizing the Fine Arts.
Winter Haven Senior High School is a public school located in Winter Haven, FL.
Chain of Lakes Collegiate High School offers a distinctive experience for students.
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Quick access to major roadways, but far enough from the big cities
While Interstate 4 provides direct access to Tampa and Orlando, living about an hour from each adds to the city's appeal. “People come here if they want to live in a more rural area away from the big city,” Davis says. “Winter Haven is an excellent example of Middle America in the South. We have a lot of northerners here, so you get a good hometown vibe.” Residents also enjoy proximity to several other major roadways, including U.S. routes 17, 27 and 92, that provide convenient travel to points of interest throughout the county, including Lakeland 15 miles away. Closer to home, Citrus Connection buses provide public transportation in and around the city. Winter Haven Hospital, which is one of the city’s biggest employers, is less than a mile north of downtown. For those who prefer to ride the rails, Winter Haven Station provides daily Amtrak service. Both Tampa and Orlando have international airports. The Central Florida Integrated Logistics Park is the latest project of the Winter Haven Economic Development Council. The park offers more than 12 million square feet of space for development on 1,500 acres in the southwest corner of the city. The location takes advantage of the existing CSX Rail Intermodal Facility and proximity to State Route 60, a major east-west corridor that runs from the Gulf of Mexico to the Atlantic Ocean.
Crime
While total service calls to police decreased by 13 percent, Winter Haven experienced a slight rise in reported crimes from 2022 to 2023, according to statistics from the city’s police department. Misdemeanor arrests increased from 74 to 84. Felony arrests increased from 34 to 50. The department's community policing initiatives include the Citizen Volunteer Program, which provides additional resources to help with crime prevention in neighborhoods, at parks and during special events.
Written By
Matt Pallister
Photography Contributed By
Jeffery Palmer
Video By
Alex Finneran
Interested in learning more about homes in this area?
Reach out to
Randy Shultz,
an experienced agent in this area.
On average, homes in Winter Haven, FL sell after 83 days on the market compared to the national average of 53 days. The median sale price for homes in Winter Haven, FL over the last 12 months is $289,590, down 2% from the median home sale price over the previous 12 months.
Welcome to this charming first-floor condominium in the heart of Winter Haven! Offering several upgrades such as hardwood floors, granite countertops and crown molding. Conveniently located on the renowned Chain of Lakes, this spacious 2-bedroom, 2-bathroom home offers the perfect blend of comfort and convenience. Step inside to enjoy an open and inviting floorplan with plenty of natural light
One or more photo(s) has been virtually staged. WATERFRONT CUSTOM St. John floor plan with CDD bond debt PAID IN FULL! A true gem in Lake Ashton. Recent Upgrades: Kinetico whole-house water softener, refrigerator (2025), New roof (2024), AC, dishwasher, stove, additional screened room with pavers, and upgraded landscaping (2022). Experience Florida living at its finest in this beautifully
Welcome home to Traditions at Lake Ruby, one of Winter Haven’s most sought-after 55+ communities! This beautifully maintained 2-bedroom, 2-bath home, built in 2019, offers 1,385 sq ft of comfortable living space and 1,773 sq ft total. Step inside to find a bright, open layout perfect for everyday living and entertaining. Enjoy resort-style amenities including two heated swimming pools, sports
This stunning 2 bedroom, 2 bath home has been thoughtfully renovated throughout, featuring newer windows and stylish vinyl plank flooring. The updated kitchen offers plenty of cabinetry and a cozy eat-in area-perfect for morning coffee or casual meals. Both bathrooms have been tastefully updated for a clean, modern feel. You'll love the spacious Florida Room across the front of the home, finished
VRRY SPACIOUS AND A BEAUTIFUL HOME! 2 BONUS ROOMS, HAVE UPDATED JUST ABOUT ALL SYSTEMS INCLUDING: ROOF, DRYWALL, FLOORING, KITCHEN, BATHROOMS, BEDROOMS, A/C, TANKLESS WATER HEATER, ELECTRICAL SYSTEM, PLUMBING, CEILING, INSULATION, AND MORE. LOTS OF SPACIOUS, A LOT OF NATURAL LIGHT. DESIGNER DOORS. OWNER artistically INSPIRED, GIVING THE HOME A UNIQUE FLAIR. A MANUAL IS AVAILABLE FOR MOST OF THE
NO CDD!Come and see this beautiful home and all it has to offer FOR YOU! located in one of the most desirable areas of Winter Haven FL. Built in 2022, this well-maintained home features over 2,600 sf, 4 bedrooms, 2.5 baths, with a dedicated office with French doors offering functionality to your workspace or easily convert it to suit your needs! As you walk through, you will notice the home
Welcome to this charming 2-bedroom, 2-bathroom upstairs condo nestled in the serene Lake Buckeye Condo community. Step inside to discover laminate and ceramic tile flooring throughout, enhancing both style and easy maintenance. The open living and dining area seamlessly flow onto the balcony, offering a perfect spot for unwinding. The kitchen, complete with appliances, showcases beautiful granite
Tucked away in Southeast Winter Haven, you’ll fall in love with the lakefront community of Cypress Landing! This beautiful, move-in ready 2-bedroom, 2-bath home showcases modern vinyl plank flooring throughout and an open floor plan designed for comfort and functionality. The spacious living and dining area flows seamlessly into the kitchen, which includes a cozy dinette — perfect for casual
Whether you’re starting your morning with coffee and calm lake views or winding down to a glowing sunset over Lake Conine, this home offers a peaceful retreat you’ll love coming back to. Perfectly situated in the waterfront community of Winter Ridge, this 2-bedroom, 2-bath home combines low-maintenance living with direct access to the Chain of Lakes (Lake Smart). Inside, laminate floors connect
Surrounded by lakes, Poinsettia Park in Winter Haven, Florida is a sunny slice of suburbia where residents enjoy their leisure time boating, fishing and golfing. “Shopping and dining are about 4 miles away on Winter Haven’s Main Street, and with nearby access to Highway 17, folks stay connected to neighboring cities like Orlando and Tampa,” says Laurie Krall, a Realtor with La Rosa Realty who has worked in real estate for over 5 years. “There’s lots to do in the area, from the Chain of Lakes to Lego Land.” Poinsettia Park is ideal for those looking for a quiet suburb not far from city amenities.
Most homes in Poinsettia Park were built in the last 20 years and are typically variations on the four-square model with Craftsman-style or Colonial Revival designs; older ranch-style homes from the midcentury can also be found. Common features include short driveways with garages, green, grassy lawns and sidewalks lining the streets; some houses may also feature oak or palm trees in the front lawns. Homes start around $200,000 for midcentury ranch-style homes and go up to $500,000 for modern construction in gated communities like Hampton Cove. Poinsettia Park Homeowners Association has authority over subsections within the community and maintains guidelines for residences.
Local kids can attend schools in Polk County, like Elbert Elementary, rated C by Niche, where students can join music extracurriculars like chorus, handbells and strings. Denison Middle receives a C and offers three academies for students to develop their skills and interests in: Academy of Business Computing, Academy of Fine Arts and Techno Robotics/STEAM pre-academy. Winter Haven Senior High receives a B-minus; students enrolled here can take Dual Enrollment classes to earn college credit at Polk State College.
Poinsettia’s Park subtropical climate makes for ideal temperatures to enjoy outdoor recreation. At The Golf Range on Dundee Road, 4 miles away, residents can perfect their swing with lessons and open tee times. Willowbrook Golf Course is about 5 miles away; a 9-hole course where golfers can hit the links and opt into their membership program for discounts. Poinsettia Park’s most notable feature is its many lakes, some of which offer premier fishing. Lake Hamilton is one of the area’s largest lakes and fishing enthusiasts can cast their lines here for largemouth bass, crappie and channel catfish; visitors can also enjoy the lake’s picnic area and public boat ramp.
Residents can head 3 miles into town to grab grocery essentials at Farm Fresh Market or pop into the local Publix. Around Lake Silver, stop into The Donut Man for breakfast grub, coffee and pastries, or enjoy some lunch at Big Daddy’s Barbeque for pulled pork and grilled bologna sandwiches. Nearby in Downtown Winter Haven, find specialty shops like Four Purls Yarn Shop, Carlton Music Center and Angelic Flowers. “People are really involved in keeping local businesses running,” says Krall. “Downtown Winter Haven has that small city feeling.”
Winter Haven’s downtown area is full of exciting events throughout the year. The historic Ritz Theatre was constructed in 1925 and operates today as movie theater, music venue and stage for theatrical productions. At the Winter Haven Theatre, patrons can enjoy community theater performances of their favorite plays and musicals. Krall recommends Bok Tower Gardens, 17 miles away, to enjoy tours and jazz music. Residents can also enjoy NCAA sports on Polk State College’s campus.
Residents in Poinsettia Park typically drive, and the nearby Highway 17 helps connect drivers throughout Winter Haven and to neighboring cities like Tampa and Orlando. “We’re not as congested as other areas of Florida,” says Krall. In Downtown Winter Haven, locals can also use Citrus Connection buses to get around. Winter Haven Regional Airport is about 7 miles away; Orlando International Airport is 45 miles away. Winter Haven Hospital is 4 miles from the neighborhood for medical needs.
Situated around the neighborhood’s namesake, residents of Lake Lucerne are never far from the water, with lakes surrounding the housing developments. “The draw with Winter Haven is that it’s part of the chain of lakes,” says sales agent Christina Maurais with CRF Resales. “It’s a beautiful environment with plenty of opportunities for outdoor activity.” In Lake Lucerne, residents can enjoy the water on boats, or residents living in the retirement communities can golf at private courses. Downtown Winter Haven is just a few miles away, so Lake Lucerne residents are close to annual events and excellent restaurants.
Lake Lucerne has multiple subdivisions. In the Lake Lucerne subdivision by the central lake, people can find New Traditional stucco houses on open streets with minimal landscaping or trees. In Royal Hills, pastel Mediterranean-style homes with rounded arches and features sit on landscaped lots with plenty of lush green and flowering plants. Style and personalization set homes apart, so each one is unique.
Retirees can settle into one of Lake Lucerne’s retirement communities. In developments like Hidden Golf Club and Swiss Golf and Tennis Club, residents can enjoy a gated community with a private golf course. Residents here may be retired, but the communities’ active social calendar and clubs keep people busy and connected.
Homes in the subdivisions tend to list between $325,000 and $350,000, though homes in the retirement communities will peak around $175,000 and list for much lower. “It’s so much cheaper than living on the coast,” Maurais says. “Life is just good here in Lake Lucerne. Once you see it, you don’t want to leave.”
Students in Lake Lucerne can attend Lake Alfred Elementary School, which receives a C-plus from Niche. Niche gives Shelley B. Boone Middle School a C-minus ranking. Haines City Senior High School offers several academies, covering topics like visual and performing arts to agriculture and children’s educational studies. The school earns a C-plus from Niche.
While the golf communities can practice their swing at any time, other Lake Lucerne residents can head to Willowbrook Golf Course. Along with specials for 9-hole games, the course has plenty of mature trees and Florida wildlife for an interesting game. Mackay Gardens and Lakeside Preserve is 112 acres alongside Lake Rochelle, boasting nature and fitness trails. Boaters can also use the dock found here.
Winter Haven Farmers Market takes place every Saturday, featuring local vendors to encourage residents to support local businesses. The organization announces the week’s vendors on Thursdays so people can plan their shopping experience ahead of time. Golfers can participate in the annual golf tournament at Country Club of Winter Haven in April, which has hosted the competition for over 30 years. CommunityFest Winter Haven offers live entertainment, games, food and meet and greets with popular movie characters.
In Winter Haven, Lucille’s American Café serves hearty steak dinners alongside comfort food favorites like chicken pot pie and homemade pies. For something sweet, try something off their sundae menu. Manny’s Original Chophouse offers a mix of steak and seafood options. Lavender ‘n Lace Tearoom creates an elegant atmosphere with seasonal dishes and occasional afternoon teas.
The Publix at Northgate is just 6 miles from Lake Lucerne. Farm Fresh Market is under 5.5 miles from the neighborhood, while Santiago’s Market is just over.
Buses stop along Lucerne Loop and connect the community with downtown Winter Haven, just 6.5 miles away. Highways 17 and 27 aren’t far from the neighborhood, helping to link residents to other communities and fun Florida attractions. Legoland is just 10 miles from Lake Lucerne, and Disney’s Magic Kingdom is 27 miles to the north. The Winter Haven Amtrak station is just 18 miles away, and Winter Haven Regional Airport is just 9 miles away. For international travel, Lakeland Linder International Airport is 26 miles away. The closest hospital is Winter Haven Hospital, just 6 miles from Lake Lucerne.
Lake Fox, a cozy waterfront community in Polk County, offers all the perks of Florida living at an affordable price. With easy access to a pair of neighborhood lakes, residents are conveniently positioned to enjoy the Winter Haven lifestyle. Relaxing on pontoon boats with friends and family, angling for that next big catch in fish-heavy waters and skiing are daily parts of life. Residents have the luxury of living in a wholly residential community, yet they also enjoy proximity to golf, theme parks and Old Florida dining.
Winter Haven is famous for its lakes. Almost two dozen comprise the city’s chain of lakes, a network of waterways that is connected by canals, but more than 50 dot the landscape. “The lakes are the reason anyone comes to Winter Haven,” says Emily Ward, a Realtor with EXP Realty who lives in nearby Cypress Gardens. Residents can access any of the lakes with minimal effort, but there are plenty of opportunities to enjoy lakefront living without leaving the neighborhood. Lake Fox is a 56-acre private lake, and Lake Daisy is a 135-acre public lake. Both are large enough to accommodate boats and related activities, but small enough that canoes and kayaks are an option. Central Florida is a hot spot for fishing, and the lakes are stocked with sportfish such as bass, crappie and bluegill. The private docks that ring both lakes can be used for bankside fishing, and they also provide the perfect location to sit, drink in hand, and watch the sun set over the water. Florida’s most popular recreational land activity also is easily accessible to residents, as Cypresswood Golf & Country Club is just north of the neighborhood. The semi-private club features a par-72, 18-hole course that stretches for more than 6,800 yards. Other amenities include a driving range and a bar and grill with patio seating. Golfers also can receive individualized lessons and participate in multi-person clinics. Just west of the neighborhood is the Lake Region Audubon Nature Preserve, where visitors can traverse scenic wooded trails with interpretive signage that lead to Lake Ned. Eagles and alligators highlight the array of native flora and fauna to be found in their natural habitats. The preserve also includes the Street Nature Center, which offers educational programs for children.
Polk County is the fastest-growing county in the nation. Much of that has to do with available land, but another key factor is cost. That makes neighborhoods such as Lake Fox additionally appealing. “A lot of people are looking to purchase a Florida home, and the Orlando/Kissimmee area is pretty tapped out. So if someone is looking to invest, Winter Haven is a great place,” Ward says. “We’re near Orlando and near Tampa, but we have a smaller state of mind. With lower prices, it’s a great place for people looking for longer-term investments.” Polk County also has fewer restrictions on buying homes as rental properties, an important factor for those seeking a seasonal retreat. Neighborhood housing is highlighted by ranch-style and contemporary custom homes featuring private driveways, attached garages and ample yard space in quiet subdivision settings. “The average home in Winter Haven is about $350,000,” Ward says. “You can get a lot of house here for that money, usually about 2,000 to 2,500 square feet.” Manufactured homes in the 55-plus communities of Lake Fox Village and Garden Grove Oaks offer a more affordable alternative with the added bonus of amenities that include swimming pools, shuffleboard courts, lake access and clubhouses that host community dinners, holiday celebrations, card games and more. Single-family homes along the lakefronts are the neighborhood’s most expensive properties. Overall, prices range from $50,000 to the mid-$500,000s.
Younger students can attend Garden Grove Elementary, a C-plus-rated school by Niche within walking distance of the community, and Jewett Middle Academy, a B-rated magnet school. Older students can attend Winter Haven Senior High, a B-minus-rated school that offers the Advanced International Certificate of Education (AICE) program through the University of Cambridge.
Families have plenty of entertainment to choose from, with Legoland Florida nearby. In addition to theme park rides, the water park is a popular attraction, and visitors can catch water ski shows featuring Lego characters. Peppa Pig Theme Park, the latest addition to Legoland’s sprawling complex, offers an array of colorful rides and activities dedicated to the cheeky British porcine character and her family. As Legoland expanded, it took over Cypress Gardens, Florida’s oldest theme park. The meticulously landscaped grounds on the shores of Lake Eloise are home to nearly 8,000 flower varieties from 90 countries. Offering discounted rates to locals, the park isn’t simply a tourist attraction. “The neighborhood is near Legoland, so that can be a draw,” Ward says. “Legoland treats its Florida residents pretty well.”
Featured dining destinations include Ovation Bistro & Bar, which serves up comfort food classics along a stretch of Cypress Gardens Boulevard corridor that forms the neighborhood’s southern edge. Harry's Old Place, an Old Florida eatery on nearby Ned Lake that specializes in seafood, is another popular stop. “Harry’s has been around for quite a while,” Ward says. “It’s one of the old family-run businesses in this area.” A Walmart Supercenter is conveniently located near Ovation Bistro, and Cypress Gardens Boulevard leads directly to the Publix-anchored Winter Haven Square about 2 miles away, across the street from Legoland in the heart of Winter Haven. “Lake Fox isn’t commercialized, and you’re technically out of the city limits,” Ward says. “But you’re still just minutes away from the main drag.”
Residents can take Cypress Gardens Boulevard via car or bus to Downtown Winter Haven, whose cultural attractions include the Historic Ritz Theatre and Gram Parsons Derry Down, a contemporary concert venue. The downtown area also hosts citywide events, including the annual Taste of Winter Haven and CommunityFest. U.S. Highway 27, which forms the neighborhood’s eastern border, provides easy access north to Haines City and south to Lake Wales. Lakeland is less than 15 miles directly west. Winter Haven also is conveniently located between Tampa and Orlando and their international airports. Both cities are about 50 miles away via Interstate 4.
Jan Phyl Village, a small community 5 miles west of Winter Haven, was created in the mid-20th century when a Vermont man purchased 1,200 acres and named the area after his two daughters, Janet and Phyllis. After its development, the village became popular with airmen working at the Bartow Airbase, less than 10 miles south, and quickly filled up with sturdy ranch-style homes. "The per capita price point for homes and taxes in this area are some of the lowest in the state," says Melissa Witter, lifetime Winter Haven resident and local real estate agent at Keller Williams Realty Smart 1. "And it's very well connected if you're a commuter."
At the center of the neighborhood are Simmers-Young Park's athletic facilities and the Auburndale Speedway racetrack, while a municipal complex housing the Polk County Sheriff's Office and other county services sits on the community's southwest corner. Recker Highway runs parallel to the train tracks along the neighborhood's eastern border and is lined with automotive businesses, industrial parks, restaurants, and small community churches.
Jan Phyl Village was primarily developed between the 1950s and ‘70s as a bedroom community for local airmen and flight instructors stationed at nearby Bartow Air Base during the Korean War. “It’s primarily block homes, very safe and reliable,” Witter says. “There’s not any Homeowners Association, so there aren’t as many restrictions on renovations either.” Clusters of close-set homes lie on the east and west here, separated by a large stretch of undeveloped land in the middle. Three-bedroom midcentury ranch-style houses dominate the neighborhood, often selling for around $200,000, but many multi-story New Traditional-style houses from the 1990s are also mixed in, selling for as much as $600,000. Within residential areas, wooded lots surrounded by maple and pine trees sit along narrow paved county roads with gravel or cracked pavement encroaching on either side.
The Central Polk Parkway lies just west of Jan Phyl Village, providing a quick and easy connection to Interstate 4, about 13 miles north. Once on the interstate, Tampa to the west and Orlando to the north are less than 50 miles away. Winter Haven Regional Airport is about 6 miles northeast, while Winter Haven Hospital is located 5 miles east, near downtown. Though the nearest train station sits 4 miles north in Auburndale, the tracks run along the community’s western border.
Local kids are zoned for Polk County schools like Lake Shipp Elementary, rated by C Niche, or the C-minus-rated Westwood Middle. The B-minus-rated Auburndale Senior High offers the Saddle Creek Logistic Academy, which teaches technical design and application, and an Agritechnologies Academy, which focuses on agricultural science and horticulture. On the west side of Jan Phyl Village, the Polk State College Center for Public Safety provides professional training and education for law enforcement and corrections workers.
Along Jan Phyl Village’s southern edge, Spirit Lake Crossing Shopping Center is anchored by a Publix, while Circle K and CVS are found nearby. Just outside the neighborhood, independently owned grocery store Green’s Market has been serving the community for almost 50 years, and a couple of miles to the west is Lonesome Oak Blueberry Farm, where locals can spend the day picking fresh berries to keep or share. While most dining options lie further east in Winter Haven, residents can head to the Tacos My Friend food truck to enjoy street-style Mexican food or visit Ramona Deli for Dominican cuisine.
At the center of the neighborhood, Simmers-Young Park is the community’s main hub for outdoor activities, featuring ten multi-purpose fields, baseball and softball facilities, and a shaded playground; an attached dog park features a grassy, fenced-in meadow. Winter Haven is home to 19 lakes, including Thomas Lake on Jan Phyl Village’s southeast corner, where locals can enjoy year-round freshwater fishing. On the neighborhood’s east side, the Imperial Polk Gun Club is a skeet and trap shooting range with five skeet and four trap fields for shotgun sport shooting.
Located at the center of the neighborhood, Auburndale Speedway racetrack has operated under various names, including Tri-Cities Speedway and Winter Haven Speedway, but locals know it simply as “The Dale.” The track hosts racing on most weekends throughout the year, with engines cooling off during a summer break from mid-June to late August. While the speedway attracts a large crowd, noise pollution is dampened by the undeveloped wooded land surrounding the track.
Cypresswood is a master-planned community where golf courses and country clubs offer luxury, convenience and amenities. With over 1,000 residential units and 14 neighborhood associations within Cypresswood Community Association, the area has plenty of housing options for various preferences. The main golf course, which opened in 1969 and was voted the best course in Winter Haven for 2023, is owned by the Cypresswood Community Association. “The developer wanted it to stay a golf course, so he leased it to the homeowner’s association for one dollar a year for the next 50 years,” says Tom Hevel, Assistant Golf Professional at Cypresswood Golf & Country Club. “I imagine if it’s a golf course for all that time, it’ll be a golf course forever.” Residents here not only have access to country club amenities, but also to shopping, dining and education nearby. Cypresswood students are zoned for Polk County Public Schools, which is in the top 50 districts in the state, according to Niche.
While most residents here spend outdoor time on the golf course, in the pool or at the gym at the Cypresswood Golf & Country Club or at The Country Club of Winter Haven, other public parks are available nearby. Locals can get some fresh air at the Michael V. Lewis Arboretum and Parrott Trail, where 42 acres of land host a mixture of native and exotic plants. The trail is about 1.5 miles and features picnic shelters and the personal plant collection of Talbot Lewis, who took decades to landscape the area. For fishing enthusiasts, there are plenty of lakes nearby, though some are private and prohibit public recreation. Cypresswood is also under 5 miles from Legoland, and under 30 minutes from Disney World. The neighborhood sits about 2 hours from both east and west coast beaches.
The main restaurant in the area is Cypresswood Golf & Country Club’s restaurant, the Cypresswood Pub, though residents travel outside of the neighborhood for more options. “Folks around here ride their golf carts everywhere,” Hevel says. “There’s a little strip mall nearby with a sandwich shop and a dollar store. People go there all the time.” Cypresswood is a short drive to Legacy Craft BBQ, which serves slow-smoked Southern BBQ, handmade sauces and fresh pies and cobblers. The Dundee Diner is another popular spot, known for its homestyle cooking. For groceries, Winn-Dixie is within 2 miles of the neighborhood, and a Walmart Supercenter is under 6 miles south.
The neighborhood has plenty of activities throughout the year to keep the community close. The Cypresswood Social group works to improve the events and opportunities in the area and is currently working to convert some tennis courts into pickleball courts. The Cypresswood Pub has live music on the weekends, yappy hours for the four-legged residents and corn hole. The country clubs hold special activities, as well, including tennis clinics and community service events, including blood drives.
Most homes here were constructed in the 1980s to early 2000s and bear ranch-style architecture. New construction is still popping up today, including custom builds on sprawling lots. Properties often sell between $200,000 and $600,000, with outliers on both ends of the range. Price not only depends on home size, but also location on the course. “I’d say about 70% of people just move here because they like the house they find, and 30% are here for the golf,” says Hevel. Houses often have two- or three-car garages and green lawns shaded by palm trees, and some have private pools in enclosures that protect the area from bugs and severe sunlight.
Students in the Cypresswood neighborhood can begin their education at Elbert Elementary and Denison Middle, which both earn C grades on Niche. Winter Haven Senior High School earns a B-minus rating and is part of the Advanced International Certificate of Education program (A.I.C.E.) through the University of Cambridge. For a private pre-kindergarten through 12th grade option, Winter Haven Christian School is within a few miles of most residences for faith-based learning.
Public transportation does not reach the neighborhood, and Cypresswood residents usually get around by car or golf cart. Major routes are nearby, such as US Highway 27, which flows north toward Gainesville. Florida State Road 60, from Tampa to the east coast, is within 15 miles, which is a 20-minute drive from Cypresswood. For air travel, Orlando International is about 45 miles away. Other amenities, such as health care and houses of worship are typically found toward the west in Winter Haven, within about 6 miles.
Eclectic dining. Cultural attractions. Lakefront recreation. On the surface, these are the reasons that Winter Haven is the fastest-growing city in one of the fastest-growing regions in the country. But if you dig a little deeper, you’ll find that the work of city officials and business leaders has laid the foundation. “There’s a unique level of collaboration and cooperation to do what is best for Winter Haven,” says Sara Beth Wyatt, president and CEO of the Winter Haven Chamber of Commerce. “We start with ‘Yes,” and then see if we can make it happen.” Nothing epitomizes the ongoing success of their efforts more than Downtown Winter Haven, the vibrant centerpiece of a flourishing city. “Full disclosure, I live and work downtown, so I’m a big fan,” Wyatt says. “There’s just so much to do. A lot of that is centered around the lakes, and we like to joke that you run into a lake at the end of every street, but we’ve got bars, restaurants, ice cream shops, shopping. You can park your car once and enjoy all of it.”
The neighborhood is anchored by a burgeoning dining scene. Nutwood, owned by Michelin star-rated chef Steven Rojas, is the city’s premier farm-to-table restaurant. Arabellas is known far and wide for its upscale Italian dishes. “I can’t tell you the number of times I’ve heard of people driving 45 minutes-plus just for the dining experience,” Wyatt says. Adler’s elevates comfort food with its contemporary twist on burgers. The Smokin’ Ox is the go-to spot for everything barbecue. For relaxed dockside dining away from the buzz of downtown, Harborside is a popular established eatery serving up seafood favorites. Bowen Yard, a new food and event space featuring six eateries, is the latest project of the Six/Ten LLC development group. “They are very partial to whom they want to attract,” Wyatt says. “A private entity that can be a little more particular in recruiting companies to Winter Haven will make sure we have a diverse mix.” Adding to the diversity are established eateries from outside the city such as Lucille’s American Café and Delectable Delights that have recently opened downtown locations. “They see something in Winter Haven,” Wyatt says. There are plenty of nightlife options as well. Featured stops include speakeasy-style Social Cocktail Lounge, which features live music, Grove Roots Brewing Co. and The Union Taproom. The neighborhood is served by two primary commercial corridors -- U.S. Route 17, known locally as 3rd Street, and Cypress Gardens Boulevard. Walmart, Publix, Aldi and Lowe’s are among the convenient retail options along the corridors.
The neighborhood also is the city’s cultural center. Theatre Winter Haven is home to popular community theater productions, and the Historic Ritz Theatre, established in 1925, features movies, concerts and improv comedy acts. Gram Parsons Derry Down, a relatively new addition to the entertainment scene, is a contemporary concert venue that is the result of restoring a teen club originally built to showcase a young Gram Parsons, a Winter Haven native whose “Cosmic American music” is considered the precursor to alternative country. The downtown area also hosts citywide events throughout the year. Annual celebrations include Taste of Winter Haven, Craft Beer Crawl and family friendly gatherings such as CommunityFest and Bark in the Park. Downtown also hosts the popular Winter Haven Farmers Market every Saturday. “We’re not as busy or chaotic as Tampa or Orlando, but there’s still so much activity,” Wyatt says.
At 624 acres, Lake Howard is the largest of several lakes in the neighborhood, several of which are connected by canals. Lakes Howard, May, Shipp, Cannon, Mirror and Spring Lake are all connected. Other neighborhood lakes include Silver, Martha, Maude and Idyl. That concentration provides residents with easy access to daily water-related activities throughout the year. Boaters in need of speed can put the throttle down and race across the larger lakes, which offer space for water skiing, an activity the city has long been known for. If relaxation is the aim, the lakes provide an idyllic setting for a pontoon boat float with friends and family. Anglers are ever-present, searching for their next big catch in waters stocked with bass, crappie and bluegill. “I think people appreciate the lakes, but they don’t quite realize what we have here,” Wyatt says. “You could jump in a boat and travel from southeast Winter Haven to northwest Winter Haven quicker than you could drive. The majority of the lakes in Winter Haven have public access, and the city has done a great job maintaining them. We have a lakefront lifestyle that you don’t often find.” South Lake Howard Nature Park and Martin Luther King Park are lakefront green spaces with walking trails. The latter is home to the Winter Haven City Tennis Center, the Winter Haven Senior Adult Center and monthly performance of the Cypress Gardens Water Ski Team on Lake Silver. Organized athletic activity takes place at the Chain O’ Lakes Complex, a sprawling park on the shores of Lake Lulu that is the site of a $20 million redevelopment project. Slated to be finished in early 2025 in time to host regional tournaments, the complex will be anchored by four artificial-turf baseball fields. Future plans include the addition of a multi-purpose field, playground and boardwalk.
Traditional ranch-style homes and other midcentury designs are prominent among established housing, which also includes Spanish-style and cottage-style homes. Contemporary custom homes in gated communities highlight new construction. Prices range from the low $200,000s to the mid-$600,000s. Lakefront homes are the neighborhood’s most expensive, typically priced from the low $800,000s to more than $1.5 million. Alternative options include waterfront condominiums starting in the low $100,000s and manufactured homes in 55-plus communities starting at $40,000. “A lot of people are looking to purchase a Florida home, and the Orlando/Kissimmee area is pretty tapped out. So if someone is looking to invest, Winter Haven is a great place,” says Emily Ward, a Realtor with EXP Realty. “We’re near Orlando and near Tampa, but we have a smaller state of mind. With lower prices, it’s a great place for people looking for longer-term investments.”
Florida offers a robust school-choice program, and Winter Haven’s top-rated institution, Chain of Lakes Collegiate High, is located downtown. A-rated by Niche, the charter school allows motivated 11th- and 12th-graders to take high school and college courses simultaneously. The school is located on the Winter Haven campus of Polk State College, which offers a variety of work certificates, associate’s degrees and bachelor’s degrees focusing on health, science, education and law enforcement. Frank E. Brigham Academy, a B-plus-rated magnet school, is the top elementary option in the neighborhood, which also is home to Denison Middle, a C-rated school, and Winter Haven Senior High, a B-minus-rated school.
The neighborhood’s centralized location provides easy access to travel throughout the region. U.S. Highway 17 connects south to Bartow and north to U.S. Highway 92, which connects directly to Lakeland about 15 miles west. U.S. Highway 27, located a few miles east of downtown, connects south to Lake Wales and north to Haines City and Davenport. The neighborhood is roughly equidistant between Tampa and Orlando. The major metropolitan areas are both about 50 miles away via Interstate 4. Closer to home, Citrus Connection bus stops are spread throughout the neighborhood, which also is home to an Amtrak train station that provides daily commuter service. The Winter Haven Regional Airport, located about 5 miles north of the neighborhood, is a busy public-use facility, but it does not offer commercial service. However, both Tampa and Orlando have international airports.
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