MLS data updated Aug 26, 2026
Winter Haven
Florida's Chain of Lakes City
Winter Haven, FL
Home to LEGOLAND Florida and the stunning Chain of Lakes, Winter Haven offers diverse waterfront living, a revitalized downtown, and strong value across all price points.
Median sold: $285K · Median days on market: 49 · Sold-to-list: 97.6% · Source: Stellar MLS
About 1.7 months of inventory — homes are selling faster than new ones come on the market, so sellers hold the leverage (under 4 months = seller's market).
Aggregate statistics from recent Stellar MLS closed sales and live MLS inventory. A market read, not an appraisal of any home or a listing of individual sales.
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Ryan's Take on Winter Haven
Winter Haven is a lake town first, and everything about the market follows from that. The 24-lake Chain of Lakes is fully navigable by private boat, and the headline I keep coming back to with clients is the value gap: dockable chain frontage here runs a fraction of what comparable access costs on Orange County's Butler Chain. That's why I see remote workers and equity buyers from pricier markets, plus serious anglers, since Polk County is genuine bass-fishing country with tournament infrastructure to match.
This is a destination market, not an Orlando commuter suburb, fifty-plus miles out, so it rewards buyers who prioritize lifestyle over a daily drive: Polk County employees at Publix, Amazon, and AdventHealth, plus 55-plus retirees comparing Traditions to The Villages. On schools, don't stop at the district's B rating, the single fact most buyers miss is Chain of Lakes Collegiate High, where students can graduate with an associate's degree. Buy waterfront with eyes open: budget for dock inspection, flood insurance, and the lakefront premium. LEGOLAND drives real short-term-rental demand southeast near Lake Eloise, but underwrite that occupancy as seasonal, not Disney year-round.
— Ryan Solberg, Broker/Owner, MaxLife Realty
Under Contract
17 homes pending in Winter Haven · Avg. $296K
Winter Haven · 3rd Quarter 2026
1243 sales · Stellar MLS · last 12 mo
$285K
Median Sale Price
49 days
Median Days on Market
97.6%
Sold-to-List
$166
Median $/sqft
Recent Sales Map
43 recent individual sales in and around Winter Haven · FL public records · no addresses published
Approximate sale locations — dots are offset ±1 home for privacy
| Beds | Baths | Sq Ft | Listed | Sold ▼ | List Price | Sold Price | $/Sq Ft | DOM |
|---|---|---|---|---|---|---|---|---|
| — | — | 8,445 | — | 9/1/25 | — | $1,700,000 | $201 | — |
| — | — | 3,831 | — | 9/1/25 | — | $795,000 | $208 | — |
| — | — | 3,488 | — | 9/1/25 | — | $525,000 | $151 | — |
| — | — | 4,247 | — | 9/1/25 | — | $475,000 | $112 | — |
| — | — | 3,279 | — | 9/1/25 | — | $440,000 | $134 | — |
| — | — | 3,470 | — | 9/1/25 | — | $440,000 | $127 | — |
| — | — | 3,526 | — | 9/1/25 | — | $436,800 | $124 | — |
| — | — | 4,672 | — | 9/1/25 | — | $360,000 | $77 | — |
| — | — | 3,009 | — | 9/1/25 | — | $339,000 | $113 | — |
| — | — | 2,727 | — | 9/1/25 | — | $329,000 | $121 | — |
| — | — | 2,336 | — | 9/1/25 | — | $326,000 | $140 | — |
| — | — | 2,488 | — | 9/1/25 | — | $325,000 | $131 | — |
| — | — | 2,835 | — | 9/1/25 | — | $315,000 | $111 | — |
| — | — | 2,294 | — | 9/1/25 | — | $310,000 | $135 | — |
| — | — | 2,266 | — | 9/1/25 | — | $307,900 | $136 | — |
| — | — | 2,395 | — | 9/1/25 | — | $304,300 | $127 | — |
| — | — | 3,064 | — | 9/1/25 | — | $300,000 | $98 | — |
| — | — | 1,988 | — | 9/1/25 | — | $297,000 | $149 | — |
| — | — | 2,478 | — | 9/1/25 | — | $297,000 | $120 | — |
| — | — | 2,608 | — | 9/1/25 | — | $295,000 | $113 | — |
| — | — | 2,060 | — | 9/1/25 | — | $285,000 | $138 | — |
| — | — | 2,680 | — | 9/1/25 | — | $283,300 | $106 | — |
| — | — | 2,043 | — | 9/1/25 | — | $280,000 | $137 | — |
| — | — | 2,098 | — | 9/1/25 | — | $270,000 | $129 | — |
| — | — | 1,961 | — | 9/1/25 | — | $270,000 | $138 | — |
| — | — | 2,956 | — | 9/1/25 | — | $260,000 | $88 | — |
| — | — | 1,441 | — | 9/1/25 | — | $250,000 | $173 | — |
| — | — | 2,061 | — | 9/1/25 | — | $235,000 | $114 | — |
| — | — | 2,029 | — | 9/1/25 | — | $225,000 | $111 | — |
| — | — | 1,535 | — | 9/1/25 | — | $215,000 | $140 | — |
| — | — | 1,221 | — | 9/1/25 | — | $208,000 | $170 | — |
| — | — | 2,084 | — | 9/1/25 | — | $205,000 | $98 | — |
| — | — | 1,966 | — | 9/1/25 | — | $180,000 | $92 | — |
| — | — | 2,258 | — | 9/1/25 | — | $172,000 | $76 | — |
| — | — | 1,037 | — | 9/1/25 | — | $170,000 | $164 | — |
| — | — | 1,724 | — | 9/1/25 | — | $160,000 | $93 | — |
| — | — | 1,828 | — | 9/1/25 | — | $150,000 | $82 | — |
| — | — | 1,620 | — | 9/1/25 | — | $143,400 | $89 | — |
| — | — | 1,144 | — | 9/1/25 | — | $143,000 | $125 | — |
| — | — | 1,679 | — | 9/1/25 | — | $140,000 | $83 | — |
| — | — | 1,232 | — | 9/1/25 | — | $135,000 | $110 | — |
| — | — | 2,657 | — | 9/1/25 | — | $132,500 | $50 | — |
| — | — | 1,148 | — | 9/1/25 | — | $127,900 | $111 | — |
Currently For Sale
50 active listings in Winter Haven
$189/sqft
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$209/sqft
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$278/sqft
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$282/sqft
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$177/sqft
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$169/sqft
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$181/sqft
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$246/sqft
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$272/sqft
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$181/sqft
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$178/sqft
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$217/sqft
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| Beds | Baths | Sq Ft | List Price | $/Sq Ft | DOM | Pool | Waterfront | View |
|---|---|---|---|---|---|---|---|---|
| 4 | 2 | 2,385 | $450,000 | $189 | 194 | — | ✓ | Water |
| 3 | 1 | 1,100 | $229,900 | $209 | 0 | — | — | — |
| 3 | 2 | 1,258 | $349,900 | $278 | 38 | — | — | — |
| 4 | 2 | 2,125 | $599,900 | $282 | 120 | — | — | — |
| 3 | 2 | 1,242 | $220,000 | $177 | 349 | — | — | — |
| 3 | 2 | 1,800 | $305,000 | $169 | 13 | ✓ | — | — |
| 3 | 2 | 800 | $145,077 | $181 | 537 | — | — | — |
| 4 | 4 | 2,118 | $520,000 | $246 | 51 | — | ✓ | Lake Howard |
| 4 | 3 | 3,483 | $949,000 | $272 | 7 | — | ✓ | Water |
| 3 | 2 | 1,863 | $337,500 | $181 | 20 | — | — | — |
| 4 | 2 | 1,824 | $324,900 | $178 | 2 | — | — | — |
| 3 | 2 | 1,220 | $264,950 | $217 | 7 | — | — | — |
| 4 | 3 | 1,900 | $324,500 | $171 | 97 | — | — | — |
| 3 | 2 | 1,517 | $299,950 | $198 | 183 | — | ✓ | Lake Thomas |
| 3 | 2 | 1,292 | $265,000 | $205 | 147 | — | — | — |
| 4 | 3 | 2,639 | $409,000 | $155 | 119 | — | — | — |
| 3 | 3 | 2,039 | $385,000 | $189 | 21 | ✓ | — | — |
| 3 | 2 | 1,788 | $324,700 | $182 | 58 | ✓ | — | — |
| 3 | 1 | 850 | $215,000 | $253 | 36 | — | — | — |
| 4 | 2 | 1,816 | $319,900 | $176 | 2 | — | — | — |
| 4 | 3 | 2,004 | $315,000 | $157 | 9 | ✓ | — | — |
| 2 | 2 | 720 | $160,000 | $222 | 28 | — | — | — |
| 4 | 2 | 2,522 | $359,900 | $143 | 19 | — | — | — |
| 3 | 2 | 1,741 | $342,900 | $197 | 98 | — | — | — |
| 4 | 2 | 1,741 | $344,900 | $198 | 104 | — | — | — |
| 4 | 2 | 2,032 | $384,900 | $189 | 125 | — | — | — |
| 4 | 3 | 2,378 | $429,900 | $181 | 125 | — | — | — |
| 3 | 2 | 1,164 | $289,900 | $249 | 35 | — | — | — |
| 3 | 2 | 1,572 | $435,000 | $277 | 6 | — | — | — |
| 4 | 4 | 2,230 | $399,900 | $179 | 14 | — | — | — |
| 3 | 3 | 2,352 | $450,000 | $191 | 15 | ✓ | — | — |
| 3 | 2 | 1,675 | $308,000 | $184 | 37 | — | — | — |
| 3 | 2 | 1,930 | $307,000 | $159 | 37 | — | — | — |
| 3 | 2 | 1,728 | $229,900 | $133 | 69 | — | — | — |
| 4 | 3 | 2,300 | $355,000 | $154 | 14 | — | — | — |
| 3 | 2 | 1,310 | $249,500 | $190 | 91 | — | — | — |
| 3 | 2 | 1,355 | $289,900 | $214 | 48 | — | — | — |
| 2 | 3 | 1,407 | $199,950 | $142 | 153 | — | ✓ | Lake Roy/Lulu Canal |
| 5 | 2 | 2,992 | $405,000 | $135 | 65 | — | — | — |
| 4 | 2 | 1,520 | $240,000 | $158 | 430 | ✓ | — | — |
| 3 | 2 | 1,851 | $225,000 | $122 | 49 | — | — | — |
| — | 0 | — | $175,000 | — | 504 | — | — | — |
| 3 | 2 | 1,158 | $234,900 | $203 | 175 | — | — | — |
| 5 | 3 | 3,022 | $475,900 | $157 | 197 | ✓ | — | Water |
| 3 | 2 | 1,708 | $249,900 | $146 | 12 | — | — | — |
| 3 | 2 | 1,124 | $279,000 | $248 | 14 | — | — | — |
| 3 | 1 | 1,080 | $144,900 | $134 | 21 | — | — | — |
| 2 | 2 | 1,220 | $210,000 | $172 | 188 | — | — | — |
| 3 | 2 | 1,109 | $239,999 | $216 | 92 | — | — | — |
| 3 | 2 | 2,309 | $309,999 | $134 | 226 | — | — | — |
Winter Haven Market — Common Questions
Is Winter Haven a buyer's or seller's market in 2026?+
Winter Haven is currently a seller's market with about 1.7 months of inventory. About 1.7 months of inventory — homes are selling faster than new ones come on the market, so sellers hold the leverage (under 4 months = seller's market).
What is the median home sale price in Winter Haven?+
Based on Florida Department of Revenue public records over the last 6 months, the median sale price in Winter Haven is approximately $285K, up about 5.6% from a year earlier.
How many homes are for sale in Winter Haven?+
There are currently 172 active listings in Winter Haven, with homes selling at roughly 103.6 per month. That works out to about 1.7 months of inventory.
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Ryan Solberg
MaxLife Realty
321.373.3536
5.0 ★ · 42 reviews
What clients say
All 42 reviews on Zillow“Highly organized. Moves very quickly. Broad reaching resources, up-to-date advertising methods. Hard working, has all the materials for staging on hand — and sold in less than 30 days.”
“Wow, what an amazing experience. Ryan was able to help me find the best home in Windermere. He is very knowledgeable and very resourceful. He helped me close a very big deal.”
Report generated August 26, 2026 at 3:01 PM ET· Powered by Stellar MLS
MLS Data:Active and pending listing data is sourced from the Stellar MLS as distributed by MLS GRID. Listings courtesy of Stellar MLS as distributed by MLS GRID. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The MLS GRID does not guarantee the accuracy of this data, which may not reflect all real estate activity in the area.
Sold Data: Sales analysis is derived from Florida Department of Revenue public property records(arm's-length transactions). Ryan Solberg and MaxLife Realty LLC are not affiliated with Winter Havenor its HOA. This report is not intended to solicit properties already listed for sale nor to cause a breach of an existing agency relationship. Data should be independently verified. E&OE.
Based on information submitted to the MLS GRID as of August 26, 2026 at 2:18 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of August 26, 2026 at 2:18 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA