Winter Haven Real Estate

Winter Haven Real Estate

Welcome to Winter Haven, Florida – a charming city nestled in the heart of Polk County that perfectly blends small-town warmth with vibrant community spirit. Known as the "Chain of Lakes," Winter Haven boasts over 50 sparkling lakes, making it a paradise for outdoor enthusiasts, water sports lovers, and nature aficionados alike. The scenic beauty of the area is matched only by its rich history and welcoming atmosphere.

Winter Haven is not just about picturesque views; it’s a community that thrives on connection and culture. With a bustling downtown area filled with unique shops, delightful eateries, and local art galleries, residents and visitors alike can enjoy a variety of dining and shopping experiences. The city also hosts numerous events throughout the year, including the popular Winter Haven Music Festival and the annual Christmas Parade, which foster a strong sense of community.

Families will appreciate the excellent educational opportunities provided by the Polk County School District, along with a range of recreational programs and parks that cater to all ages. The city’s strategic location offers easy access to major highways, making it a convenient hub for those who wish to explore nearby attractions like the world-renowned Walt Disney World and Legoland Florida Resort.

Whether you’re looking to settle down, retire, or simply enjoy the sunshine, Winter Haven offers an inviting atmosphere and a lifestyle that embraces both relaxation and adventure. Discover your new home in this delightful city, where every day feels like a vacation!

Newest Listings in Winter Haven

4 Beds ⋅ 2 Baths ⋅ Villa Park Or Stone & Manns SubDv. ⋅ 33881 Zip Code

Great investment opportunity!! A little over 4100 sq ft total between both buildings. The front 2 story house was initially divided into 5 apartments. 3 downs stairs and 2 upstairs. In a separate building there are 2 apartments. The income property is a fixer upper that could either be restored to 5 apartments or back to one large house with 2 rentals in the back of the property for income or a place to live while being renovated. Tons of square footage, With the right vision this could be a great chance turn this into income!

640 Avenue I Nw, Winter Haven

Acreage SubDv. ⋅ 33881 Zip Code

1 AC Retail Outparcel For Sale or Lease in Winter Haven, Florida! This prime location along Martin Luther King Blvd boasts 30,000+ AADT and over 215 feet of frontage. Positioned in Winter Haven’s commercial corridor, this outparcel is located next to many national retailers, including a Home Depot-anchored shopping center. Zoned C-3, or Commercial Highway, this site allows for a wide range of retail and commercial uses, making it ideal for retail, restaurant, service-based businesses, and many other commercial uses. Additional nearby Retailers include Walgreens, O'Reilly Auto Parts, Publix, AutoZone, Family Dollar, Mister Car Wash, and Mid Credit Union. The property is easily accessed by a private road with two options for ingress/egress via Martin Luther King Blvd. and Unity Way NW. This property is also eligible for incentives from the Florence Villa Community Redevelopment Agency (CRA). These incentives could allow for reducing certain development costs, impact fees, and many other options. Lakeland-Winter Haven is the 2nd fastest growing MSA in the U.S. This is an ideal opportunity for investors or businesses looking to capitalize on a bustling retail environment with strong traffic flow and a growing customer base. The current parcel number includes existing building (1850 Olympian Way) to the south, which will not be included in this purchase. This property will be split upon purchase and a new tax / parcel ID will be created.

Olympian Way, Winter Haven

4 Beds ⋅ 3 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code

Under Construction. Brand new, energy-efficient home available by Aug 2026! An open floorplan that makes entertaining easy in the open kitchen, dining, and great room that flow to the patio. The primary suite is tucked in the rear of the home offering plenty of privacy and features a spacious walk-in closet and shower. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

3757 Giorgio Drive, Winter Haven

1 Beds ⋅ 1 Baths ⋅ Eloise Woods Lake Mariam Unit SubDv. ⋅ 33884 Zip Code

Don't miss this affordable 2-bedroom, 1-bath home nestled in the Lake Mariam area of Winter Haven. Situated on a spacious 0.23-acre lot, this property offers a great opportunity for an investor, rental portfolio, or buyer ready to add their own style and updates. Conveniently located near shopping, restaurants, medical facilities, golf courses, and Winter Haven's renowned Chain of Lakes. Some photos have been virtually enhanced.

107 Lake Elizabeth Drive Unit B, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Acreage SubDv. ⋅ 33880 Zip Code

This mobile home features a unique design, highlighted by a massive front porch that spans the entire width of the house, giving it the charming, spacious feel of a ranch-style home. It is a cozy, practical, and functional living space that allows you to enjoy views of the one-acre lot—which offers endless possibilities—from both inside and out. The home includes 3 bedrooms, 2 bathrooms, a laundry room, and a dream kitchen, all with NO Homeowners Association (HOA) fees. Wood-look vinyl flooring runs throughout the house. The bright kitchen features recessed-panel cabinets, a pantry, and a central island with storage and dining space. The spacious primary suite includes a private bathroom with a separate shower. The property and its grounds attract various bird species throughout the year, delighting residents with incredible sunrises and sunsets; you get the best of both worlds—proximity to the city and the peaceful tranquility of country living. Don't miss the chance to see it; schedule an appointment to discover how you can enjoy a peaceful, serene lifestyle close to everything at such an affordable price.

2363 Gerber Dairy Road, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code

Under Construction. Brand new, energy-efficient home available by Aug 2026! Prepare dinner while catching up on the days events from this homes chef-inspired kitchen which overlooks a great room and dining area. Well appointed primary suite provides a restful retreat at the end of the day and has a spacious walk-in closet. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

3968 Giorgio Drive, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code

A Home That's Ready When You Are — Oakwood Estates, Winter Haven Some of life's best decisions are also the simplest ones. This lovingly maintained, fully furnished manufactured home in Oakwood Estates invites you to skip the hassle and step straight into the lifestyle you've been looking forward to — because everything has already been taken care of, and everything stays. Fresh interiors, thoughtful updates, and a warm, welcoming layout make this one of the most effortless purchases you'll make. Step inside and you're immediately greeted by natural light pouring through double-pane windows, setting a bright, airy tone throughout. The kitchen shines with stainless steel appliances, wood-look countertops, a newer sink, and crisp white cabinetry — and yes, everything stays, right down to the air fryer. The dining area features beautiful built-in cabinetry and shelving, flowing seamlessly into a spacious living room complete with an electric reclining sofa, flat screen TV, and comfortable seating. Luxury vinyl plank flooring runs throughout, tying it all together with style and ease of maintenance. Both bedrooms are generously sized and fully furnished. The primary suite features a walk-in closet, electric reclining bed, and a quality foam mattress. The Florida room offers updated ceiling fans, a brand-new AC unit, and convenient access to the in-home washer and dryer hookups — a true bonus in this community. Slide open the door to the enclosed lanai and enjoy your morning coffee overlooking lush, manicured landscaping — your own quiet corner of Florida. Additional highlights include hurricane shutters, vinyl siding, a 2017 roof, an irrigation system, and an updated electrical panel for peace of mind. Then there's the community. Oakwood Estates is a gated, beautifully maintained 55+ resident-owned community in the heart of Winter Haven — one of Polk County's most desirable areas. Residents enjoy two heated pools, two clubhouses, tennis and pickleball courts, shuffleboard, bocce ball, a miniature golf course, horseshoes, a fishing lake with pier, RV and boat storage, a library and activities center, pool tables, and a vibrant, active activities committee that keeps the social calendar full year-round. Lighted streets, underground utilities, and security cameras throughout the common areas reflect a community that takes pride in where it lives. This is Florida living, fully loaded and ready to go.

4332 Cherrywood Street, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code

New Carpet throughout most of the home. Plus many of the windows have been updated to thermal pane insulated windows. If that is not enough the TPO roof was installed in December 2023. The home has a nice layout with a huge primary bedroom with huge walk in closet. Location is convenient in Oakwood Estates, a 55+ community, right across from the office and close proximity to one of the pools. Enjoy the many amenities at Oakwood including two pool, two clubhouses, miniature golf, fishing pier, shuffleboard and much, much more. Join in on the many activities including weekly Koffee Klatch, potluck meals, and dances. The two heated pools offer many hours of relaxation. Or just sit out on the screened front porch and watch the world go by. This home is priced to sell. Check it out today!!

4027 Rolling Oaks Drive, Winter Haven

5 Beds ⋅ 3 Baths ⋅ Hidden Creek SubDv. ⋅ 33880 Zip Code

Virtually Staged. Welcome to this stunning 5-bedroom, 3-bathroom pool residence located in the highly sought-after, gated Hidden Creek community of Winter Haven. Perfectly positioned just minutes from the Polk Parkway and LEGOLAND Florida Resort, and conveniently situated between Lakeland and Winter Haven, this home offers an ideal blend of comfort and unbeatable accessibility. Inside, you will find soaring ceilings, a smart split-floor plan, a dedicated office or bonus room, a large den, and a 2-car garage that delivers ultimate flexibility for modern living, complemented by brand-new carpet replaced in 2025. The beautiful kitchen features granite countertops and a convenient walk-in pantry, while the primary suite serves as a true private retreat featuring a deep soaking tub, separate walk-in shower, dual sinks, a vanity, and a massive walk-in closet. Situated on a generous 0.35-acre lot, the property offers rare privacy, as the home backs up to a preserve with peaceful natural views. The absolute crown jewel of the home is the expansive, screen-enclosed lanai and sparkling saltwater pool with a heated spa, creating an exceptional resort-style outdoor living space masterfully designed for effortless entertaining, relaxing weekend lounging, or simply enjoying the tranquil Florida breeze in total privacy. Schedule your private showing today and discover a rare gem in Winter Haven!

1020 Lena Run Court, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Jewett Mary B SubDv. ⋅ 33881 Zip Code

BEAUTIFUL 3BR/2BA NEW CONSTRUCTION BLOCK HOME LOCATED IN THE HEART OF WINTER HAVEN WITH VIEW OF LAKE IDYL. CONVENIENTLY LOCATED TO EVERYTHING IN CENTRAL FLORIDA (POLK PARKWAY, I-4, TAMPA AND ORLANDO). THIS HOME BOASTS GORGEOUS STAINLESS STEEL APPLIANCES, QUARTZ COUNTERTOPS IN THE KITCHEN AND BATHROOMS, LARGE INDOOR LAUNDRY ROOM, LUXURY VINYL FLOORING THROUGHOUT, DOUBLE SINK IN THE PRIMARY BATHROOM, OPEN FLOORPLAN, 30 YEAR ARCHITECTURAL SHINGLES, BLINDS THROUGHOUT. YOU DON'T WANT TO MISS OUT ON OWNING THIS BEAUTIFUL HOME

851 Avenue R Ne, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Saddle Oaks Mobile Home Sub SubDv. ⋅ 33880 Zip Code

Spacious 3 Bedroom 2 Bath Mobile Home with no HOA! Great Winter Haven location! New Shingle Roof in 2018! This home has been lived in by one family since it was new! Now it is Vacant and ready for a new family! Split Bedrooms, Spacious Family Room, Living Room/Dining Room Combo, Two Concrete Driveways, Covered Carport, Screened Front Porch with wood burning fireplace/grill, Fenced Front Yard, No Rear Neighbors just to name a few of the features here! Home is priced to sell! Schedule your showing today!

820 Water Oaks Drive, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Villamar Phase 6 And Phase 6d SubDv. ⋅ 33884 Zip Code

Under Construction. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

3740 Giorgio Drive, Winter Haven

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