Skidmore
Homes for Sale in Winter Haven, FL
All 844 homes for sale in Winter Haven, FL · median $279,900 · 345 homes for sale in 33884 · Polk County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of November 2026, the MLS records 13 closed sales in Skidmore in Winter Haven, FL since 2015, the most recent in October 2024. Across Winter Haven as a whole, 1,657 homes closed in the last 12 months at a median of $279,065, 54 median days on market, with 788 homes for sale today. At that median and Polk County's FY2025-26 rate of 16.19 mills, annual property tax runs about $4,520 ($3,840 with the full homestead exemption).
Skidmore is a small pocket of 50 homes in Winter Haven, and what drives price here is not a tidy builder spec sheet. The median living area is roughly 4,800 square feet, which is genuinely large, but the homes span a wide stretch of build years and the median was built around the mid-1990s. That combination means condition, updates, and lot do the heavy lifting on value. Expect a wide spread from house to house rather than a predictable per-square-foot number.
The current snapshot shows no active listings and no recent closings in the window we track, so there is no live pricing tension to read. For sellers, that thin turnover means a well-prepared listing sets the comp rather than chasing one. For buyers, it means patience: inventory here surfaces occasionally, not on demand, and you may need to be ready to move when a home does come up.
Figures in this note are as of October 26, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Nearby homes for sale
No active listings inside SKIDMORE right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Skidmore is a compact, owner-occupied enclave of large homes in Winter Haven, Polk County, where roughly nine in ten homes carry a homestead exemption and turnover is quiet.
Stellar MLS sales records identify 25 homes in SKIDMORE that have changed hands since 2005, built between 1973 and 2006 (median 1995), with a median living area of about 3,506 sq ft and a typical 4-bedroom, 3.5-bath layout; 100% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.
Who Skidmore is best for.
Best for
- Buying to hold long term in a quiet, owner-occupied setting
- Needing substantial square footage well above typical Winter Haven stock
- Buyers willing to wait for a rare listing and move when one surfaces
Probably not for
- Needing to close quickly from a ready pool of inventory
- Looking for new construction or a turnkey community with shared amenities
- Wanting a predictable per-square-foot price backed by frequent comps
The market around Skidmore
Skidmore is a small community — 55 recorded sales on file, most recently in 2024 — too few for its own price trend. Here is the market around it.
In ZIP 33884, 457 homes are on the market and 25% are under contract — a steady corner of Winter Haven.
Across Polk County, 5,189 homes are active and 1,757 pending (25% under contract).
Homes here are single family residence.
In ZIP 33884 (Winter Haven), 651 homes closed in the last 12 months at a median of $308K ($163/sq ft), down 0.9% year over year, with a median 57 days on market. Right now 2 active and 2 pending listings. See the live ZIP 33884 housing market and the Polk County market.
ZIP and county figures describe the wider market, not Skidmore specifically. Momentum Research analysis of MLS records.
Schools
- Polk County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Polk County Public Schools (verify by address) · Public
- Chain of Lakes Elementary, Denison Middle, Winter Haven Senior High (verify by address) · By address
- Magnet and choice options may apply · Choice
Zoned schools reflect the assignments reported on recent Skidmore listings and can change; always confirm with Polk County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Skidmore address.
Recent Developments in Skidmore
Development, infrastructure, retail, and school activity affecting Skidmore, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated November 2026.
- October 2026Schools
County commission and School Board begin updating growth and school capacity agreement
At a joint Oct. 29 meeting at the Lake Myrtle Sports Complex, both boards agreed to advance updates to their interlocal agreement on school planning. Topics included reducing portable classrooms, concurrency service areas and workforce housing options. Superintendent Fred Heid called the current agreement outdated.
What it may mean for the marketUpdated coordination between growth approvals and school capacity could shape where new school space is added and how new housing is phased across the county. The site is about 11 miles north of Skidmore.
Source: Polk County Government - October 2026Infrastructure
Sheffield Road to reopen early as next construction phase closes Old Bartow Eagle Lake Road
Sheffield Road west of Spirit Lake Road was set to reopen Oct. 19, over a month ahead of schedule. Phase 3 closes Old Bartow Eagle Lake Road between Spirit Lake Road and Spirit Landings Boulevard from Oct. 18 until about Jan. 11, 2027. Detours use Crystal Beach, Thornhill and Spirit Lake roads.
What it may mean for the marketCommuters in northeast Winter Haven regain Sheffield Road now but face a detour on Old Bartow Eagle Lake Road through early January. The project is about 5 miles north of Skidmore, elsewhere in Polk County.
Source: Polk County Government - September 2026Infrastructure
$1.2 Million Sidewalk Project Completed in Northwest Lake Wales
Lake Wales finished a $1.2 million sidewalk phase covering Orange Avenue, Wetmore Street, Sessoms Avenue, Seminole Avenue, Seaboard Avenue, Dorsett Avenue, B Street and C Street, rehabilitating existing walks and adding new ones. A state grant paid for the work, and an earlier phase finished in 2025. Landscaping and street trees remain scheduled in some areas.
What it may mean for the marketNew sidewalks improve walking access to nearby streets and amenities in northwest Lake Wales. The project is about 8 miles southeast of Skidmore, elsewhere in Polk County.
Source: DailyRidge - September 2026Development
Winter Haven Commission Approves 13-Townhome Affordable Housing Project at 7th Street SW and Avenue N SW
Winter Haven commissioners voted unanimously on Aug. 24 to support Heart for Winter Haven's plan for about 13 transitional affordable townhomes on 0.818 acres at the southwest corner of 7th Street SW and Avenue N SW. The city will provide a $350,000 forgivable grant from its Supplemental Affordable Housing Trust Fund, with a seven-year affordability requirement. No construction dates were given.
What it may mean for the marketThe project adds a small number of affordable units near central Winter Haven, supporting local workforce housing supply. The site is about 4 miles northwest of Skidmore.
Source: DailyRidge - July 2026Development
Haines City Data Center Proposal on Hold Over Water Capacity
Texas based Cielo Digital Infrastructure has proposed a data center on Marion Road and State Road 544 East in Haines City, requesting 150,000 gallons of potable water per day. City officials say the project remains preliminary, is awaiting additional water allocation from the Southwest Florida Water Management District, and has not yet come before the commission for approval.
What it may mean for the marketA proposed data center signals commercial and industrial interest in the Haines City area while highlighting water infrastructure limits that could shape the pace of future development. The project is about 9 miles northeast of Skidmore, elsewhere in Polk County.
Source: Bay News 9 - May 2026Development
SouthState Plans $17M Office in Downtown Winter Haven
SouthState plans a $17.2 million, five story, 40,035 square foot Class A office building on vacant parcels along Central Avenue in downtown Winter Haven. The regional operations center would house about 125 employees, with construction expected to begin in July 2026 and take 12 to 16 months.
What it may mean for the marketA new downtown office building adds employment space and Class A commercial inventory to downtown Winter Haven, supporting the area's redevelopment and taxable value. The project is about 4 miles northwest of Skidmore, elsewhere in Polk County.
Source: Tampa Bay Business & Wealth
Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in Northeast Florida.
The Skidmore buying strategy.
If we were buying in Skidmore today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Skidmore.
Large homes, slow turnover
The headline fact is scale: a median living area near 4,833 square feet puts Skidmore well above typical Winter Haven stock. The build years range across several decades and the median lands around 1995, so you are looking at a neighborhood of established, substantial houses rather than new construction. No community amenities turn up in current MLS listings, so the draw is the homes and the location, not shared facilities.
A homestead share above 90% tells you this is a lived-in, hold-for-the-long-term street rather than an investor churn. That stability is a double edge. It supports a settled feel, but it also means listings are infrequent, and with no active inventory and no recent closings on record, both sides should treat a sale here as an event to prepare for carefully, not a quick transaction.
The location and the amenities are priced into every listing in Skidmore. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a 50-home pocket with thin turnover and no live comps, pricing is a judgment call, not a formula. We underwrite each home on its own condition and lot, pull in the broader Winter Haven large-home context, and tell you plainly when a number does not hold up. For sellers that means defensible pricing in a market with few anchors; for buyers it means a realistic read before you commit to a rare opportunity.
Skidmore in 15 seconds.
Tools for a Skidmore buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Skidmore sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Skidmore, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Skidmore home worth?
Get a no-obligation home value based on real comparable sales in Skidmore, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See all homes for sale in Winter Haven →
| Location | Winter Haven, Polk County, FL · ZIP 33884 |
|---|---|
| Homes in the community | 50 (FL DOR 2025 assessment roll) |
| Years built | 1969–2019 (median 1995.0) |
| Typical living area | 4,833 sq ft (median) |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 90% |
| Zoned public schools | Polk County Public Schools (verify by address); Chain of Lakes Elementary, Denison Middle, Winter Haven Senior High (verify by address); Magnet and choice options may apply |
Data as of August 2, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2015 through 2024; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Skidmore key facts,” movewithmomentum.com/neighborhoods/skidmore, data as of August 2, 2026.
Housing distress & ownership in SKIDMORE, Winter Haven
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period November 2026 through November 2026. Deemed reliable but not guaranteed.
More Winter Haven home searches
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- Winter Haven home values: what is my house worth?
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- Florida property tax calculator
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Frequently Asked Questions
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What share of Skidmore is owner-occupied?
When were the homes in Skidmore built?
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Where is Skidmore, and what county is it in?
Should you buy in Skidmore?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: June 30, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (4 streets, ZIP 33884)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Schools | 2025-26 district assignments + FLDOE school grades; verify with the district |
| Historical depth | Closed-sale records back to 2015 (13 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
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