Stately Oaks
Homes for Sale in Winter Haven, FL
True comps, carrying-cost math, and listings before the portals.
As of November 2026, the MLS records 19 closed sales in Stately Oaks in Winter Haven, FL since 2006, the most recent in March 2026. Across Winter Haven as a whole, 1,657 homes closed in the last 12 months at a median of $279,065, 65 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).
Stately Oaks is a small, established pocket of about 50 homes in Winter Haven, built between 1958 and 1980 with a median vintage around 1960. Price here is driven almost entirely by condition and how much updating a given home has seen, not by floor plan novelty - these are mid-century houses with a median of roughly 2,128 square feet, which is more room than most homes of that era deliver. Expect a wide spread between original and renovated, and plan to underwrite each property on its own merits.
With zero active listings and only a couple of closings in the recent window, this is a thin, low-turnover market. For a seller, that scarcity can work in your favor when a well-prepared home does come up. For a buyer, it means patience: you may wait for the right house rather than choose from several at once, and when one surfaces you should be ready to move.
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 Stately Oaks 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
Stately Oaks is a tenure-heavy enclave of mid-century homes in Winter Haven, Polk County, where about two-thirds of owners hold a homestead exemption - a sign people stay put and listings are infrequent.
Stellar MLS sales records identify 32 homes in STATELY OAKS that have changed hands since 2006, built between 1958 and 1980 (median 1961), with a median living area of about 1,629 sq ft and a typical 3-bedroom, 2-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 Stately Oaks is best for.
Best for
- Buying to settle into a low-turnover, established neighborhood where owners tend to stay long-term
- Seeking more square footage than typical mid-century homes offer and willing to renovate to taste
- Buyers who can wait patiently for the right listing and act decisively when one appears
Probably not for
- Needing to close on a short timeline from a current pool of available homes
- Wanting new construction or move-in-ready finishes without any updating work
- Looking for community amenities such as a pool, clubhouse, or gated access
The market around Stately Oaks
Stately Oaks is a small community — 17 recorded sales on file, most recently in 2024 — too few for its own price trend. Here is the market around it.
In ZIP 33881, 339 homes are on the market and 24% are under contract — a steady corner of Winter Haven.
Across Polk County, 5,189 homes are active and 1,757 pending (25% under contract).
The housing mix here is 98% single family residence, 2% ?.
In ZIP 33881 (Winter Haven), 406 homes closed in the last 12 months at a median of $308K ($163/sq ft), down 3.3% year over year, with a median 68 days on market. Right now 1 active and 1 pending listings. See the live ZIP 33881 housing market and the Polk County market.
ZIP and county figures describe the wider market, not Stately Oaks 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
- Confirm zoned elementary, middle, and high · By address
- Magnet and choice options may apply · Choice
Zoned schools reflect the assignments reported on recent Stately Oaks 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 Stately Oaks address.
Recent Developments in Stately Oaks
Development, infrastructure, retail, and school activity affecting Stately Oaks, 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 5 miles north of Stately Oaks.
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 site is about 2 miles east of Stately Oaks.
Source: Polk County Government - 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 7 miles east of Stately Oaks, elsewhere in Polk County.
Source: Bay News 9 - June 2026Development
Haines City Commission Reviews Lake Eva Estates Subdivision
Haines City reviewed a preliminary plat for Lake Eva Estates, a 31 lot single family subdivision on 16.68 acres west of 10th Street South by Lake Eva. The project is zoned low density residential and includes an approved traffic study.
What it may mean for the marketA new single family subdivision adds for sale housing supply in the Lake Eva area and reflects continued residential platting activity in Haines City. The project is about 9 miles northeast of Stately Oaks, elsewhere in Polk County.
Source: The Citrus Tea - 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 2 miles south of Stately Oaks, 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 Stately Oaks buying strategy.
If we were buying in Stately Oaks 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 Stately Oaks.
A condition-driven mid-century market
The housing stock dates to 1958 - 1980 with a median build year near 1960, so the practical questions are mechanical and structural: roof, systems, electrical, and whether a home has been meaningfully updated or left largely original. At a median of about 2,128 square feet, there is genuine space to work with, which rewards buyers willing to renovate and sellers who have already invested in the right improvements.
A homestead share around 66% tells you this is a hold-and-stay area rather than an investor churn. That stability is part of the appeal, but it also explains the thin inventory - with no active listings as of early August 2026 and just two closings in the recent window, comparable sales are limited and each transaction carries extra weight in setting value.
The location and the amenities are priced into every listing in Stately Oaks. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a market this thin, the data does the talking only if someone reads it correctly. With no active listings and few recent closings, pricing a Stately Oaks home - or making a defensible offer on one - takes real local judgment about how condition translates to value on 1960s stock. We track this pocket closely and will tell you plainly when a home's price reflects its updates and when it does not.
Stately Oaks in 15 seconds.
Tools for a Stately Oaks 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 Stately Oaks sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Stately Oaks, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Stately Oaks home worth?
Get a no-obligation home value based on real comparable sales in Stately Oaks, 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 33881 |
|---|---|
| Homes in the community | 50 (FL DOR 2025 assessment roll) |
| Years built | 1958–1980 (median 1960) |
| Typical living area | 2,128 sq ft (median) |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 66% |
| Zoned public schools | Polk County Public Schools (verify by address); Confirm zoned elementary, middle, and high; Magnet and choice options may apply |
Data as of August 2, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2006 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Stately Oaks key facts,” movewithmomentum.com/neighborhoods/stately-oaks-winter-haven, data as of August 2, 2026.
Housing distress & ownership in STATELY OAKS, 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
- All homes for sale in Winter Haven, FL
- Gated communities in Winter Haven
- Winter Haven home values: what is my house worth?
- ZIP 33881 housing scorecard
Winter Haven guides & data
Florida buyer guides
- Florida home insurance rates by county
- Florida property tax by county
- Florida property tax calculator
- What flood zone X means
- The 4-point inspection, explained
- Florida flood insurance calculator
- Florida housing market map
- Interactive housing market map (county, ZIP and community)
- Save Our Homes tax estimator
- How to stop a foreclosure in Florida
- Florida documentary stamp tax, explained
- Cheapest places to live in Florida
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Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- Avenue S NW (7 homes on record)
Email me new listings in Stately Oaks
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Stately Oaks
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Stately Oaks will answer, and the answer is published on this page for the next buyer.
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Polk County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Polk County scorecard.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.
Frequently Asked Questions
How many homes are in Stately Oaks?
What share of Stately Oaks is owner-occupied?
When were the homes in Stately Oaks built?
Do cash buyers compete in Stately Oaks?
What schools serve Stately Oaks?
Who is the best real estate agent for Stately Oaks?
How do I find a top Winter Haven real estate agent who knows Stately Oaks?
Can Momentum Realty connect me with an agent for Stately Oaks?
Where is Stately Oaks, and what county is it in?
Should you buy in Stately Oaks?
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 25, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (community parcel extract) |
| 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 2006 (19 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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See how STATELY OAKS fits the bigger picture — live prices, inventory, and Momentum Scores: