Winter Haven Commercial Real Estate

Winter Haven is the one market in this batch where nearly as much space is offered for lease as for sale. The Stellar MLS snapshot of October 29, 2026 showed 20 active for-sale and 18 active for-lease listings. Mixed-use led the lease side with seven listings, ahead of office with four, and office led the sale side with five of the 20.

Sellers were slow to clear. The median listing had been on the market 207 days, and half of the 20 for-sale listings were past 180 days. Eleven were priced below their original ask, though the median cut, 8.8%, was shallower than in neighboring Lakeland. The median ask was $750,000 across the 20, and the median asking price per square foot was $362 across the 19 listings with usable building area, well above Lakeland's $223, so read it alongside the price bands: six listings under $500,000, seven from $500,000 to $1 million, six from $1 million to $3 million and one above $3 million.