Collaborative efforts have created an enviable neighborhood
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.”
Downtown Winter Haven is a laid back sunny neighborhood in Florida.
Downtown Winter Haven is the vibrant centerpiece of one of Florida’s fastest-growing cities.
A burgeoning contemporary dining scene. Historic venues. Downtown Winter Haven has it all.
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Dining options are endless
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.
Nutwood, is an intimate farm-to-table restaurant located in Downtown Winter Haven
Adler’s serves up elevated comfort food in a relaxed atmosphere.
The Smokin’ Ox offers the best in modern barbecue in Winter Haven.
Harborside is a popular dockside eatery serving up fresh seafood and other favorites.
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Cultural attractions and community gatherings
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.
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.
Vibrant works of art are abundant at the festival where local artist showcase their works.
Winter Haven Farmers Market is a great weekly event to find fresh produce & local art pieces.
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"A lakefront lifestyle you don't often find"
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.
With over 50 interconnected lakes throughout the Winter Haven area fishing is a common hobby.
The World Famous Cypress Gardens Ski Team continues with monthly shows in Winter Haven.
Locals can break a sweat at the Winter Haven Tennis Center playing Tennis for Pickleball.
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Affordable alternative to nearby metropolitan areas
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.”
Ranch-style designs are prominent among the neighborhood’s established housing.
Lakefront homes are the neighborhood’s most expensive, but have the most majestic evening views.
Contemporary custom homes in gated communities highlight the new growth in Winter Haven.
Spring Lake Towers Boat Slip & Dock
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Neighborhood is home to city's top-rated school
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.
Frank E. Brigham Academy is a magnet school located in Winter Haven, FL.
Denison Middle School is home to over 800 students in grades 6-8.
Winter Haven Senior High School is a public school located in Winter Haven, FL.
Welcome to Chain of Lakes Collegiate High School in Downtown Winter Haven.
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Conveniently located to regional points of interest
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.
The neighborhood’s centralized location provides easy access to travel throughout the region.
The Citrus Connection bus stops are spread throughout the neighborhood of Winter Haven.
The Polk Parkway allows for access to Tampa & Orlando.
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 Downtown Winter Haven neighborhood?
to let others know what life in this neighborhood is like.
Crime and Safety
1 - Low Crime, 10 - High Crime
Downtown Winter Haven
US
Homicide
4
4
Sexual Assault
5
4
Assault with Weapon
5
4
Robbery
5
4
Burglary
5
4
Motor Vehicle Theft
5
4
Larceny
5
4
Crime Score
5
4
Source: WhatIsMyCrimeRisk.com
Downtown Winter Haven Demographics and Home Trends
On average, homes in Downtown Winter Haven, Winter Haven sell after 103 days on the market compared to the national average of 56 days. The median sale price for homes in Downtown Winter Haven, Winter Haven over the last 12 months is $215,000, down 10% from the median home sale price over the previous 12 months.
Virtually Staged. Welcome to Waterside Village, a community of just 48 homes that offers a peaceful setting while keeping you close to everything Winter Haven has. This move-in ready 3-bedroom, 2-bath home offers an open floor plan, spacious kitchen with a large walk-in pantry, and a backyard designed for entertaining. Enjoy the screened-in lanai, pool deck, and above-ground pool with a recently
Welcome to your new home! This spacious 5/2 has all you could need for functionality, family, and entertaining. Nestled just near Lake Elbert, less than a mile from downtown Winter Haven where you will find tons of local shopping, food, and lounges. On the main floor you will find both a formal and family living room, dining room, kitchen with attached laundry and plenty of pantry space, and the
SELLER OFFERING $3,000 TOWARDS BUYER'S CLOSING COSTS. Make this charming and well-maintained home in Winter Haven your home. Featuring gorgeous wood flooring throughout the main living areas and porcelain ceramic tile in the kitchen. The beautifully updated kitchen features stainless steel appliances, a gas stove, soft-close cabinets, and ceramic tile flooring, offering both style and
WELCOME HOME TO STONEBRIDGE! Step through your private, custom-gated Courtyard into a beautifully updated Stonebridge Patio Home that is truly MOVE-IN-READY! NEWER ROOF (2024), NEWER ELECTRIC PANEL (2024), NEWER WINDOWS AND SLIDERS (2022), NEW GUTTERS & DOWNSPOUTS (2026). This fabulous property is located in FEMA Zone X, a low-risk flood zone. From the moment you enter, you'll be impressed by the
Auction Property. Ranch-style home offering 2 bedrooms and 1.5 bathrooms with a spacious living room and a good-sized yard. Features include a durable metal roof, RV electrical hookups, and a chicken coop. Some updates in the kitchen. Short Sale subject to lender approval.
Welcome home to this well-maintained 2-bedroom, 1-bath patio home located in the 55+ community of Parkland Village. This move-in-ready home offers numerous recent updates, including a new roof (December 2025), new windows (2024–2025), new A/C (2022), and a new refrigerator and stove (2026), providing comfort and peace of mind for years to come. Inside, you'll find thoughtful features such as
Welcome to easy lakefront living in the highly desirable Sandy Cove community on the Winter Haven Chain of Lakes! This beautiful 2nd floor condo offers low-maintenance living perfect for a full-time residence, seasonal retreat, or investment opportunity. This 2-bedroom, 1-bath condo features a bright and functional layout with comfortable living and dining spaces designed for everyday living and
Short Sale. **SHORT SALE** BANK APPROVED PRICE** CAN CLOSE QUICKLY*** Welcome to this beautiful 3-bedroom, 2-bathroom block home perfectly positioned at the end of a quiet cul-de-sac in Winter Haven's sought-after Cypress Gardens neighborhood. With 1,400 square feet of interior living space and a layout designed for both comfort and connection, this home checks every box. Step inside and you're
Calling all investors and house-hackers! Welcome to 1830 2nd St NW, a fantastic multi-family investment opportunity located right in the heart of Winter Haven. This well-maintained duplex features two spacious, mirror-image units, each offering a highly desirable 3-bedroom, 1-bathroom layout perfect for maximizing rental income and attracting long-term tenants! Both units boast bright,
Short Sale. Discover the exceptional potential of this 3-bedroom, 2-bathroom home ideally located in the heart of Winter Haven, offering unbeatable access and flexibility with no HOA restrictions. Positioned just minutes from major highways, shopping centers, dining, and local amenities, this property delivers convenience that’s hard to match. Inside, the home features a spacious living area, an
MUST SEE! Discover this beautifully remodeled first-floor condo with NO STAIRS to climb, offering the convenience and comfort of true single-level living. Perfect for year-round residents, seasonal owners, or anyone seeking easy accessibility, this move-in-ready home combines modern updates with an exceptional lifestyle in one of Winter Haven's most desirable lakefront communities. Located just
Charming & Renovated Single Family Home With NO HOA & Great Investment Potential! Welcome to this cozy 3 Bed, 1 Bath residence that features a seamless open floor plan, with a bright living room and dining room combo that flows into the modern kitchen. The interior has been thoughtfully updated with luxury vinyl and tile flooring throughout, providing a stylish and easy-to-clean environment. The
SELLER VERY MOTIVATED. NO HOA!!!!! MAKE OFFER! Looking for an affordable, move-in ready home under $210k with a fenced yard and no HOA in central Winter Haven? This updated 3-bedroom, 1-bath concrete block home offers 1,191+ square feet of easy living—plus a bright Florida bonus room and a private backyard that's fully fenced, perfect for pets, gardening, or relaxing outdoors. Inside, you'll find
165 SW 5th St, Winter Haven, FL 33880 presents a strong opportunity for commercial redevelopment or investment in a growing Winter Haven location. This vacant parcel offers approximately 17,476 square feet and is positioned in an area with surrounding commercial and mixed-use activity. The site is ideal for a local owner-user, boutique developer, retail or service user, professional office,
Discover a rare opportunity to own this architecturally distinctive 2-bedroom, 2.5-bath residence located in the gated community of Casarena on the Lakes. This well-designed home offers an impressive blend of indoor and outdoor living spaces. The main level features a formal living room with a fireplace and wet bar, a dining area, a functional kitchen with breakfast bar, a guest half bath, and
Welcome home to this charming 2-bedroom, 1-bathroom rental located in the desirable Chain of Lakes area of Winter Haven! This beautifully renovated home offers a comfortable and inviting space with plenty of room to make it your own. Featuring a newer roof installed in Fall 2023, the home also includes a versatile bonus room that can be used as a home office, guest space, playroom, or additional
Discover the essence of upscale living at The Breeze, where the vibrant spirit of Winter Haven meets the serenity of a private retreat. Our community was designed for those who demand more from their surroundings. Each residence serves as a masterclass in architectural efficiency, blending high-performance energy standards with "luxury-first" essentials. From gourmet-inspired kitchens to living
VACANT, MOVE-IN READY & PET FRIENDLY! Lease for just $1,600/month! Located in the lovely and up-and-coming Winter Haven area, this completely remodeled historic 1930s home has been beautifully restored to its former glory. This charming home offers 2 bedrooms and 1 well-appointed full bathroom, perfect for comfortable living. Situated on an oversized, fully fenced corner lot—perfect for pets—the
Discover a living experience that moves with you. At Raindance, we have reimagined the modern residence as a sanctuary of light and fluid design. Each floor plan is a masterclass in spatial harmony, meticulously curated to balance expansive windows with intimate, designer-led interiors. Our commitment to excellence is woven into the very bones of the building, exceeding the highest energy
The Best Amenities in TownThe Jade offers the most comprehensive amenity package in town, offering an unmatched blend of luxury, comfort, and convenience at one inclusive price—no other apartment complex nearby provides such a diverse range of options under one roof.
Welcome to Briarcrest at Winter Haven Apartments, ideally located near downtown Winter Haven, FL where convenience meets comfort in a picturesque setting. Choose from our spacious and versatile one, two, and three-bedroom floor plans, each thoughtfully designed to suit diverse lifestyles. Our community boasts not just one, but two sparking pools for residents to unwind and enjoy Florida's
Barrington Place at Winter Haven is an intimate and charming community located in Winter Haven, FL. Our exclusive residences offer a serene retreat for residents seeking comfort and convenience. Discover the perfect balance of tranquility and accessibility, with proximity to Cypress Gardens Blvd., top-rated schools, healthcare facilities, and shopping destinations just moments away. Choose from
Welcome to luxury living in Winter Haven. Lakeshore Club is located on the Chain of Lakes between Lake Howard and Lake Mary minutes from downtown Winter Haven.
Lakeview Tower offers newly remodeled studio and one bedroom apartment homes. It is an exceptional senior living, 62+ and disabled Community. Lakeview Tower sits right on Lake Howard, allowing breath taking views from your window.
Raingarden Apartments is a 9-unit collection of spacious luxury townhouse apartments located in downtown Winter Haven. Perfect for those looking to embrace a walkable, urban lifestyle where environmentally conscious living meets uncompromising, modern sophistication. All units have an enclosed 2-car garage and courtyard patio.
This spacious single-story ranch in Winter Haven offers 5 bedrooms and 3 bathrooms across 2,806 square feet of thoughtfully updated living space. The fresh interior paint and wood-look flooring create a bright and modern atmosphere, while multiple ceiling fans with lights keep the rooms comfortable year-round.An open-concept kitchen with white cabinetry, light countertops, and a mosaic
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.
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