COUNTRYSIDE KEY
Homes for Sale in OLDSMAR, FL
True comps, carrying-cost math, and listings before the portals.
Market Heat
COUNTRYSIDE KEY right now
🔴 Off the recent peak. The trailing-12-month median ($235K) is down 14.5% from the prior 12 months ($275K). With about 7 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending August 2. Confidence: Medium (10 and 9 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
Updated August 2, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
COUNTRYSIDE KEY market snapshot (as of August 2, 2026): the median sale price is about $235K ($212 per sq ft over the trailing 12 months of closed sales), and a median 85 days on market for closed sales. The trailing-12-month median is down 14% from the prior 12 months, computed from record-level Stellar MLS closed sales (10 closings in the current window).
COUNTRYSIDE KEY is a community of 230 homes in OLDSMAR, Pinellas County, built between 1995 and 1998 (median 1997), with a median living area of about 1,110 square feet. 66% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
The setting & the homes.
Aerial and on-site photos of COUNTRYSIDE KEY. Swipe to explore the community.
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COUNTRYSIDE KEYPrice History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending August 2 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($235K) IS the median in the snapshot above, and the move from 2025 ($275K) IS the -14.5% one-year change.
Windows contain 0 to 22 sales each (10 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2004 through 2026. Deemed reliable but not guaranteed.
Countryside Key Market Scorecard
Countryside Key is currently a thin data market. Limited supply, a median asking price of n/a.
Go deeper: true cost calculator · affordability calculator.
Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Schools
- Pinellas County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Pinellas County Schools (verify by address) · Public
- Confirm zoned elementary, middle, and high · By address
Zoned schools reflect the assignments reported on recent COUNTRYSIDE KEY listings and can change; always confirm with Pinellas County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any COUNTRYSIDE KEY address.
The COUNTRYSIDE KEY buying strategy.
If we were buying in COUNTRYSIDE KEY 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 COUNTRYSIDE KEY.
A closer look at the COUNTRYSIDE KEY market
At a median of $212 per square foot, COUNTRYSIDE KEY prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
The trailing-12-month median down 14% year over year. Homes that do trade take a median 85 days on market, useful leverage on any listing that has lingered.
The housing stock is 230 homes built between 1995 and 1998, and 66% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
The location and the amenities are priced into every listing in COUNTRYSIDE KEY. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in COUNTRYSIDE KEY buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 3 factors (4.6). Basis: Recent Direction -14.5% year-over-year; Owner Commitment 66% owner-occupied; Pricing Power 92.1% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- Mandatory HOA. Confirm current dues
- Any club/amenity membership is billed separately
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Tools for a COUNTRYSIDE KEY 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 COUNTRYSIDE KEY sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in COUNTRYSIDE KEY, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your COUNTRYSIDE KEY home worth?
Get a no-obligation home value based on real comparable sales in COUNTRYSIDE KEY, 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 homes for sale in COUNTRYSIDE KEY on the map →
Frequently Asked Questions
What is the median home price in COUNTRYSIDE KEY?
How long do homes in COUNTRYSIDE KEY take to sell?
How many homes are in COUNTRYSIDE KEY?
What share of COUNTRYSIDE KEY is owner-occupied?
When were the homes in COUNTRYSIDE KEY built?
Do cash buyers compete in COUNTRYSIDE KEY?
What schools serve COUNTRYSIDE KEY?
Who is the best real estate agent for COUNTRYSIDE KEY?
How do I find a top OLDSMAR real estate agent who knows COUNTRYSIDE KEY?
Can Momentum Realty connect me with an agent for COUNTRYSIDE KEY?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: June 24, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending August 2, 2026 |
| Housing stock & ownership | Florida DOR 2025 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 2004 (102 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.
Own a home here?
You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live your area comps.
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