Winter Haven Homes with Villa Property Style

Winter Haven, located in Polk County, Florida, is a charming city known for its picturesque landscapes and tranquil atmosphere. With its mild winters and sunny summers, Winter Haven offers residents the perfect balance between a relaxed small-town feel and the conveniences of a larger city.

This beautiful city is home to a variety of real estate options, including homes with villa property style. Villas in Winter Haven are highly sought after for their unique architectural designs and luxurious features. These properties often boast spacious layouts, elegant finishes, and private outdoor spaces, making them ideal for those seeking a blend of comfort and sophistication.

Living in a villa in Winter Haven allows residents to enjoy the benefits of a low-maintenance lifestyle. With exterior maintenance typically taken care of by the homeowners' association, residents have more time to explore the city's numerous amenities and attractions. From the renowned Chain of Lakes to the vibrant downtown area, Winter Haven offers a range of recreational activities, shopping destinations, and dining options.

Whether you're looking for a permanent residence or a vacation home, Winter Haven's homes with villa property style provide an excellent opportunity to experience the city's unique charm and relaxed way of life. With its prime location in the heart of Central Florida, Winter Haven is a city that truly has it all.

Newest Winter Haven Homes with Villa Property Style

1307 Innsbruck Ct, Winter Haven $198,900

Short Sale. CLOSE IN 60 DAYS OR LESS! QUICK and easy HECM Short Sale on this 2 bedroom 2 bath Vienna Square Villa with pond and wooded view. Located next door to the club...

2 Beds
2 Baths
Vienna Square SubDv.
33884 Zip Code

665 Broadmoor Circle, Winter Haven image

665 Broadmoor Circle, Winter Haven $165,000

Virtually Staged. Welcome to effortless Florida living in the highly sought-after gated Cypress Wood Golf & Country Club! Perfectly positioned on the beautifully maintain...

2 Beds
2 Baths
Cypresswood Tennis Villas SubDv.
33884 Zip Code

1 Enclave Drive, Winter Haven $225,000

Opportunity Knocks! Build sweat equity in this 3 bedroom 2 bathroom villa that is ready for some cosmetic updates. Make this home your own with fresh paint, new floorin...

3 Beds
2 Baths
Cypresswood Enclave Ph 01 SubDv.
33884 Zip Code

1525 Oakview Circle Se, Winter Haven image

1525 Oakview Circle Se, Winter Haven $199,000 ▼

Turn-key elegance in one of Winter Haven’s 55+ community! Welcome home to Oakview, an immaculate, highly sought-after hidden jewel. This smokefree, move-in ready 2BR/2B...

2 Beds
2 Baths
Oakview SubDv.
33880 Zip Code

1026 Medinah Drive, Winter Haven $175,000 ▼

Enjoy the Florida Country Club Lifestyle in this affordable and updated 2 bedroom 2 bath villa. Recent updates include new luxury vinyl flooring, new dishwasher and new ...

2 Beds
2 Baths
Cypresswood Villas/Green SubDv.
33884 Zip Code

1004 Medinah Drive, Winter Haven $165,000 ▼

Don’t miss this incredible opportunity to own a villa in one of Winter Haven’s most sought-after gated golf communities — at an unbeatable price! This 2-bedroom, 2-bathro...

2 Beds
2 Baths
Cypresswood Tennis Vls SubDv.
33884 Zip Code

1213 8th Street Nw, Winter Haven $189,000 ▼

One or more photo(s) has been virtually staged. SELLER NOW OFFERING 2/1 INTEREST BUY DOWN RATE WITH APPROVED FINANCING!Beautiful, well-cared-for 2BR/2BA villa in a mainte...

2 Beds
2 Baths
North Gate Village SubDv.
33881 Zip Code

1052 Medinah Drive, Winter Haven $190,000 ▼

Welcome to the affordable lifestyle of living in a Villa within a golf course community. Upon entering the front of the home you will notice a courtyard area on the left ...

2 Beds
2 Baths
Cypresswood SubDv.
33884 Zip Code

345 24th Street Nw Unit 25, Winter Haven image

345 24th Street Nw Unit 25, Winter Haven $140,000 ▼

Welcome to maintenance-free living in the heart of Winter Haven! This darling 2-bedroom, 2-bath villa is perfectly located in the desirable Imperial Villas a 55+ resident...

2 Beds
2 Baths
Imperial Villas SubDv.
33880 Zip Code

2270 Firestone Place, Winter Haven image

2270 Firestone Place, Winter Haven $185,000 ▼

Welcome to this spacious end-unit villa in Cypresswood Golf & Country Club, a gated golf community in Winter Haven known for its mature landscaping, active amenities, and...

2 Beds
2 Baths
Cypresswood Golf Villas Gi-4 SubDv.
33884 Zip Code

649 Broadmoor Circle, Winter Haven image

649 Broadmoor Circle, Winter Haven $137,500 ▼

UNDER MARKET VALUE!!! Brand NEW AC Fan motor, AC Amp Fuse and AC capacitor installed May 2026. Brand NEW fire/carbon monoxide detector alarms throughout the home. Welcome...

2 Beds
2 Baths
Cypresswood Golf Villas SubDv.
33884 Zip Code

1709 Linz Ct, Winter Haven $259,000

NATURE CALLS, flies, and strolls by this beautiful NEW CONSTRUCTION Villa. Complete, and ready for its 1st happy homeowner. Bright, fresh, and relaxing 2 bedroom 2 bath w...

2 Beds
2 Baths
Vienna Square SubDv.
33884 Zip Code