Momentum Housing Data · Home Values · Pinellas County
Buying here? See Countryside Key homes for sale and the Countryside Key community guide (Oldsmar).
Countryside Key (Oldsmar, FL): 10 recorded closings in the 12 months ending 2026-09-20, an 11-year price record, and sales split by price band and home size — every number from recorded MLS closings, none from an estimate model.
In the current window, sellers accepted a median 92.6% of original asking; the median sale took 66 days (window ending 2026-09-20).
| Year | Median sold | Median $/sqft | Median DOM | Sold ÷ original ask | Sales |
|---|---|---|---|---|---|
| 2026 | $235,000 | $212 | 66 | 92.6% | 10 |
| 2025 | $274,000 | $247 | 63 | 94.8% | 9 |
| 2024 | $285,000 | $254 | 19 | 95.3% | 7 |
| 2023 | $288,500 | $261 | 19 | 98.3% | 5 |
| 2022 | $250,000 | $225 | 4 | 102.4% | 15 |
| 2021 | $223,000 | $201 | 3 | 102.4% | 9 |
| 2019 | $155,750 | $140 | 50 | 97.2% | 4 |
| 2017 | $138,500 | $124 | 30 | 94.5% | 8 |
| 2016 | $127,700 | $115 | 17 | 97.3% | 22 |
| 2015 | $112,500 | $101 | 65 | 94.5% | 9 |
| 2014 | $98,900 | $90 | 31 | 100.0% | 3 |
Over the recorded series, Countryside Key’s median sold price moved from $98,900 (2014) to $235,000 (12 months ending 2026-09-20) — +138% over that span, with every year’s figure from recorded closings, not a model.
The recorded series starts in 2014 at $98,900. The 2020–22 run-up did what it did everywhere — Countryside Key’s median moved +61% from 2019 to 2022. Against the 2023 peak of $288,500, the current median stands at -19%. Annual sales volume here has ranged from 0 to 22 closings a year (10-yr average 6.8). With roughly 6.8 closings a year, Countryside Key’s medians move in steps, not curves — a handful of unusual sales can swing a year, which is why the sales count sits next to every figure above.
Of the 25 recorded Countryside Key closings since 2024, half landed between $235,000 and $279,000 (the middle two quartiles); the lowest recorded sale was $191,000 and the highest $287,000. If your home sits outside the middle band, the reason usually shows up in the size table below before it shows up in condition.
| Sold price band | Share of closings | Sales |
|---|---|---|
| Under $225,000 | 2 (8%) | |
| $225,000 – $241,667 | 8 (32%) | |
| $241,667 – $258,333 | 3 (12%) | |
| $258,333 – $275,000 | 3 (12%) | |
| None and up | 9 (36%) |
The same recorded closings, split into thirds by living area. Find the row your home falls in: the $/sqft figure times your square footage is the recorded-sales bracket for homes like yours here — a starting range from real closings, not a valuation of your specific property. Larger homes here have been selling at a higher price per square foot than smaller ones ($248 vs $217) — less common, and usually a sign of newer or upgraded product at the top of the range.
| Size group | Median $/sqft | Median sold | Sold range | Sales |
|---|---|---|---|---|
| Smaller homes 1,105–1,105 sq ft | $217 | $240,000 | $220,000 – $281,000 | 8 |
| Mid-size homes 1,105–1,110 sq ft | $225 | $250,000 | $191,000 – $280,000 | 8 |
| Larger homes 1,110–1,285 sq ft | $248 | $275,000 | $230,000 – $287,000 | 9 |
From the live MLS feed as of 2026-10-01: The homes listed or recently sold were built between 1995 and 1998 (median 1997); 13 of 14 listed or recently sold homes report an HOA, median $433/mo; the features listings here most often name are Gated Community - No Guard, Pool, Tennis Court(s), Deed Restrictions and Gated Community. See the current Countryside Key listings →
At Countryside Key’s $235,000 median and Pinellas County’s adopted 19.39 mills (FY2025-26), a home assessed at that price carries roughly $4,560 a year in property tax before exemptions, or about $3,740 with the full Florida homestead exemption — a buyer’s first-year figure; a long-time owner’s Save Our Homes cap can be far lower, which is one reason resale taxes jump at closing. Municipal and special-district millage varies inside the county; see the Pinellas County tax page.
Current asking prices run a median $252,250 against the $235,000 recorded sold median (+7%) — the gap between what sellers hope and what the record shows. The market is carrying about 1.8 months of supply at the current sales pace. Demand check: 0% of Countryside Key’s listings are under contract, against 19% for ZIP 34677 and 20% for Pinellas County as a whole — the community is currently absorbing slower than its surroundings, which is negotiating information. Momentum’s market-heat index for Countryside Key reads 10/100 (computed from DOM, sale-to-list, and absorption; 2020–21 peaked in the 70s here).
Asking and recorded sold prices are within a few percent of each other here, so the table above is close to what a Countryside Key buyer will actually pay; the spread on any single home comes down to size, condition and timing.
We don’t publish algorithm guesses for specific homes — they can’t see condition, upgrades, or your lot. A local agent will prepare a records-based valuation from the same closed-sale data on this page, adjusted for your home. Free, no obligation.
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Communities buyers shopping Countryside Key are also weighing (nearest by map distance), each on its own recorded 12-month closings. A median well above the neighbors is a ceiling to price against; well below is where the value argument lives.
| Community | Median sold | Median $/sqft | Median DOM | Sales |
|---|---|---|---|---|
| EAST LAKE WOODLANDS | $650,000 | $264 | 34 | 13 |
| Oaks At Countryside I The Condo | $228,000 | $177 | 160 | 5 |
| East Lake Woodlands Cluster Homes | $282,500 | $174 | 57 | 11 |
| bayside meadows ph ii | $260,250 | $228 | 5 | 4 |
| School | Level | FLDOE grade |
|---|---|---|
| Pinellas County Schools (verify by address) | Public | — |
| Confirm zoned elementary, middle, and high | By address | — |
Assignments and grades as recorded/published; both change — verify current zoning with the district before relying on it. Grades are the state’s official FLDOE ratings, reported as published.
More Countryside Key: full community guide & homes for sale · choosing an agent here · should you sell now (statewide data) · what selling costs · cash offer vs. listing
Based on Stellar MLS data distributed by MLS GRID for the period 2004 through 2026. Compiled from recorded MLS closings; deemed reliable but not guaranteed. Figures are medians for the stated windows and change as new sales record; individual homes vary widely. No automated valuation for any specific property appears on this page. Equal Housing Opportunity. © 2026 Move With Momentum LLC — brokerage licensed in FL and GA. Disclosures
Content on this page is compiled from public records, MLS data, and automated data sources, and may contain errors or be out of date. It is provided for general information only and is not a representation about any specific property, community, builder, or association. Verify all information independently before relying on it.