Your Guide to 55+ Communities in Winter Haven, Florida (Homeowner-Owned Properties)

Nestled in the heart of Central Florida, Winter Haven offers active adults an idyllic setting for retirement living. Known as the “Chain of Lakes City” with 26 interconnected lakes, Winter Haven provides a perfect balance of small-town charm, natural beauty, and big-city convenience. This guide focuses exclusively on communities where you own the land beneath your home—no mobile home parks included.

Why Choose Winter Haven?

Before exploring specific communities, here’s what makes Winter Haven special:

• Perfect Location: Equidistant from Tampa and Orlando (approximately 45 minutes to each)
• Chain of Lakes: 26 interconnected lakes offering boating, fishing, and water sports
• Affordable Living: Lower cost of living compared to coastal Florida cities
• Family Attractions: Home to LEGOLAND Florida theme park and just 30 minutes from Disney World
• Cultural Scene: Award-winning Theatre Winter Haven and excellent dining options
• Historic Charm: Named the 2019 Winner of Great Places in Florida – People’s Choice Award
• Year-Round Sunshine: Subtropical climate perfect for outdoor activities

The Communities

1. Lake Ashton

Size: Approximately 1,600 homes 
Built: 2002-2023
Type: Single-family homes and attached carriage homes
Location: Lake Wales/Winter Haven border (6 miles from downtown Winter Haven)

What Makes It Unique: Lake Ashton is the crown jewel of the Winter Haven area, sprawling across 1,200 scenic acres overlooking the picturesque Lake Ashton. This award-winning, 24-hour manned gated community offers a resort lifestyle with two championship 18-hole golf courses and some of the most extensive amenities in Central Florida. The community has received numerous accolades and is known for its exceptional value combined with luxury living.

Amenities:

• Two championship 18-hole golf courses
• 26,000 square-foot main clubhouse with:
  
  • Elegant grand ballroom
  • Full-service restaurant, lounge, and bar
  • Resort-style outdoor pool
  • Woodworking shop
  • Meeting rooms and library
  • Computer lab
  • Catering kitchen
  • Game room
• 30,000 square-foot health and fitness center with:
  
  • Weight room and cardiovascular equipment
  • Indoor heated pool
  • Courts for basketball, pickleball, and racquetball
  • Sauna
• Tennis courts
• Pickleball courts
• Four-lane bowling alley
• Surround-sound movie theater
• Onsite banking
• Boat slips available at the dock
• Covered boat and RV storage
• Walking and biking trails
• 24-hour manned gated security

Home Features: The Islander and Adventurer series range from approximately 1,290-2,600 square feet with 2-3 bedrooms, 2-3 bathrooms, and attached 2-3 car garages. Carriage homes (condos in 20-unit buildings) offer 2-3 bedrooms. All Islander homes built after 2009 are Certified Green Homes with energy-saving appliances. Adventurer homes include RV or boat garages. Many homes feature water or preserve views, covered lanais, and open floor plans. HOA fees are approximately $60 year. Lake Ashton is a CDD community and the CDD includes a maintenance fee that pays for all the amenities. Homes range from the mid $200,000s to $800,000+.

2. Traditions at Lake Ruby

Size: 552 homes
Built: 2005-present
Type: Single-family homes (resale and new construction)
Location: Winter Haven (Thompson Nursery Road)

What Makes It Unique: Traditions at Lake Ruby sits directly on the scenic banks of Lake Ruby, offering residents a true lakefront lifestyle. The community features a lakeside gazebo, dock slips for smaller boats, and a boat ramp—amenities not found in most 55+ communities. The 19,000 square-foot clubhouse rivals much larger communities, and the gated entrance provides security and peace of mind.

Amenities:

• 19,000 square-foot lakefront clubhouse with:
  
  • Grand ballroom
  • Card room and library
  • Billiards room
  • Arts and crafts studio
  • Meeting rooms
• Fitness center with cardiovascular equipment
• Aerobics studio
• Resort-style heated outdoor pool and spa
• Two tennis courts
• Three bocce ball courts
• Two shuffleboard courts
• Half basketball court
• Dog park
• Lakeside gazebo overlooking Lake Ruby
• Boat dock and boat ramp for smaller watercraft
• Walking and biking trails
• Gated entrance

Home Features: Two collections available—the Estates Collection (1,582-2,032 sq ft) and Executive Collection (1,779-2,599 sq ft). Homes feature 2-4 bedrooms, 2-3 bathrooms, and attached 2-3 car garages. Many models include dens perfect for home offices. Open floor plans with low-maintenance exteriors and covered lanais. HOA fee of approximately $504 per month includes lawn service (mowing, bush and tree trimming, mulch replacement), exterior painting of homes, cable, internet, and amenities. Homes range from the high $100,000s to $400,000+.

3. Vienna Square

Size: 181 homes total (100 villas + 81 single-family homes)
Built: Ongoing (new construction available)
Type: Attached villas and single-family homes
Location: Southeast Winter Haven

What Makes It Unique: Vienna Square is one of Winter Haven’s smallest 55+ communities, developed by Century Residential (developer of Lake Ashton). Despite being a smaller, intimate community, it boasts a 7,000 square-foot clubhouse with a state-of-the-art 30-seat movie theater—a rare amenity in communities of this size. The community offers both new construction and resale homes, providing flexibility for buyers seeking move-in-ready or customizable options.

Amenities:

• 7,000 square-foot clubhouse with:
  
  • Grand ballroom for dances and events
  • 30-seat movie theater with surround sound
  • Billiards room
  • Cards and crafts room
  • Library
  • Multi-purpose rooms
• Fitness center with group exercise classes
• Heated outdoor pool and whirlpool spa
• Tennis courts
• Pickleball courts
• Sports court
• Walking trails
• Gated entrance with 24/7 security

Home Features: Villas come in two floor plans ranging from 1,100-2,200 square feet with 2-3 bedrooms, 2 bathrooms, and attached 2-car garages. Single-family homes offer eight models ranging from 1,231-1,930 square feet with 2-3 bedrooms, 2-3 bathrooms, some with dens or studies, and attached 2-car garages. Standard upgrades include granite countertops, custom shaker cabinets, stainless steel Whirlpool appliances, upgraded Delta fixtures, designer lighting, paver driveways, screened lanais, and tranquil nature preserve views. HOA fees range from $290 (single-family)-$430 (villa) per month and include lawn maintenance, security gate remote, and professional property management. The villas HOA includes exterior paint and roof replacement making them nearly maintenance-free! Prices for new villas and homes vary based on customization.

4. Preserve at Lakeside Landings

Size: 44 homes
Built: 2016-2020
Type: Single-family homes
Location: Winter Haven

What Makes It Unique: The Preserve at Lakeside Landings is Winter Haven’s newest 55+ community, built by D.R. Horton’s Freedom Homes division (the same builder as Heritage Landings in Lakeland). This intimate, gated community features modern single-story homes with all the latest upgrades as standard features. The community’s small size creates a close-knit neighborhood feel while still offering resort-style amenities. Beautiful conservation areas with water views provide a serene natural setting.

Amenities:

• Clubhouse with multi-purpose rooms
• Resort-style swimming pool with cabana
• Scenic ponds throughout the community
• Nature trails
• Multi-purpose field
• Tot lot for grandchildren visits
• Gated entrance
• Professional lawn maintenance included

Home Features: Four floor plans ranging from 1,641-2,034 square feet with 2-3 bedrooms, 2 bathrooms, and attached 2-car garages. All homes feature first-floor master suites, open-concept living spaces, customizable flex rooms, covered lanais, and conservation or water views. Standard features include contemporary design, tile flooring in main areas, granite countertops, stainless steel appliances, and energy-efficient construction. The low HOA of approximately $180/month includes lawn maintenance. This community does have a CDD.

Location Highlights

Winter Haven’s central location provides residents with:

Nearby Attractions:

• LEGOLAND Florida theme park (13 miles)
• Disney World (29 miles)
• Lake Eva Water Park (6 miles)
• Bok Tower Gardens (nearby Lake Wales)
• Spook Hill (historic attraction)
• Theatre Winter Haven (award-winning community theater)

Shopping & Dining:

• Publix, Winn-Dixie, Walmart, and Aldi for groceries
• Colonial Promenade shopping center
• Lakeside Village shopping complex
• Diverse dining from casual waterfront seafood to fine dining
• Harry’s Old Place and Nutwood (local favorites)

Healthcare:

• Winter Haven Hospital
• Lakeland Regional Health Medical Center (30 minutes)
• Advent Health in Haines City
• Numerous urgent care and specialty medical facilities

Airports:

• Tampa International Airport (45 minutes)
• Orlando International Airport (45 minutes)
• Lakeland Linder International Airport (nearby)

Making Your Decision

When choosing a 55+ community in Winter Haven, consider:

• Budget: Communities range from affordable ($200,000s) to upscale ($500,000+)
• Lifestyle: Do you want golf (Lake Ashton), lakefront maintenance-free living (Traditions), or a more intimate community (Vienna Square, Preserve)?
• Amenities: Consider which features matter most—golf courses, movie theaters, lake access
• Community Size: From intimate 44-home communities to expansive 1,600-home developments
• Home Style: Decide between new construction with customization or move-in-ready resale homes
• Location Within Winter Haven: All communities offer convenient access to shopping and attractions

The Bottom Line

Winter Haven offers exceptional value for 55+ homebuyers seeking a lakefront Florida lifestyle without the hefty price tag of coastal communities. The Chain of Lakes provides endless recreational opportunities, while the central location means both Gulf and Atlantic beaches are just 90 minutes away. With LEGOLAND and Disney World nearby, Winter Haven is perfect for retirees who want to balance quiet lake living with easy access to world-class entertainment.

Whether you’re drawn to the extensive resort amenities of Lake Ashton, the genuine lakefront lifestyle of Traditions at Lake Ruby, the modern convenience of Vienna Square, or the intimate charm of Preserve at Lakeside Landings, Winter Haven’s 55+ communities offer something for every taste and budget—all while owning the land beneath your home.

From championship golf to lakeside sunsets, theater performances to nature trails, Winter Haven provides the perfect backdrop for an active, fulfilling retirement in the Sunshine State.

Ready to explore these communities? Contact Swan City Realty, a local real estate brokerage that specializes in 55+ communities in Winter Haven to schedule tours and find your perfect retirement home in the Chain of Lakes City.

*HOA fees are subject to change. Please check with the HOA for the most recent fees. This was updated in October 2025.