Countryside Key
Homes for Sale in Oldsmar, FL
All 172 homes for sale in Oldsmar, FL · median $329,450 · 150 homes for sale in 34677 · Pinellas County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 5 closed sales in Countryside Key Unit in Oldsmar, FL since 2006, the most recent in October 2024. Across Oldsmar as a whole, 296 homes closed in the last 12 months at a median of $364,750, 61 median days on market, with 89 homes for sale today. At that median and Pinellas County's FY2025-26 rate of 19.39 mills, annual property tax runs about $7,070 ($6,260 with the full homestead exemption).
There is not enough active listing volume in Countryside Key Unit right now to draw out a pricing pattern. That is itself useful information: it means comps here need to be pulled and verified property by property rather than inferred from a community-wide snapshot.
Current MLS listings for this community do not document any community amenities. That does not mean none exist, only that a buyer or seller should not assume a pool, gate, or clubhouse is part of the deal until it is confirmed in the listing or HOA documents directly.
Nearby homes for sale
No active listings inside Countryside KeyHomes for Sale in Oldsmar, FL 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
Countryside Key Unit sits in Oldsmar, within Pinellas County. Current MLS data does not surface community amenities, so amenity details for this community should be confirmed directly rather than assumed from the name or area.
Stellar MLS sales records identify 165 homes in Countryside Key that have changed hands since 2004, built between 1995 and 1998 (median 1997), with a median living area of about 1,110 sq ft and a typical 2-bedroom, 2.5-bath layout; 95% are townhomes. 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 Countryside Key is best for.
Best for
- A buyer comfortable verifying HOA and amenity details directly rather than relying on a listing summary.
- A buyer or seller focused on a specific property rather than a community-wide price trend.
- Someone who wants a Pinellas County, Oldsmar location and is willing to do the diligence to confirm the rest.
Probably not for
- A buyer who needs a confirmed amenity package, like a pool or clubhouse, spelled out before considering the community.
- A buyer who wants an established median price or sales history to anchor an offer strategy.
- Someone who prefers to shop by aggregated community statistics rather than individual listings.
The market around Countryside Key
Countryside Key is too small for its own price trend, so here is the market around it.
In ZIP 34677, 184 homes are on the market and 21% are under contract — a steady corner of Oldsmar.
Across Pinellas County, 6,628 homes are active and 1,729 pending (21% under contract).
In ZIP 34677 (Oldsmar), 439 homes closed in the last 12 months at a median of $365K ($239/sq ft), down 4.5% year over year, with a median 61 days on market. Right now 90 active and 20 pending listings put supply at about 4.7 months — a buyer's market. See the live ZIP 34677 housing market and the Pinellas County market.
ZIP and county figures describe the wider market, not Countryside Key specifically. Momentum Research analysis of MLS records.
Countryside Key Unit by the numbers
From county property records and closed MLS sales for the Countryside Key Unit subdivision: 21 homes on record; built 1995–1998; typical size about 1,110 heated sq ft; 2 bedrooms is the median. Housing mix: townhome 80%, condo 14%.
| Year | Recorded sales | Median price |
|---|---|---|
| 2007 | 1 | $132,000 |
| 2008 | 2 | $139,950 |
| 2009 | 6 | $104,000 |
| 2010 | 6 | $86,500 |
| 2011 | 2 | $69,500 |
| 2024 | 1 | $270,000 |
Newest recorded sale: $270,000 on 2024-10-22.
Recorded data as of 2026-09-12; counts cover addresses tagged to this subdivision in the public record, not every parcel. Not an appraisal.
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.
What the listing data actually shows
When a community shows no documented amenities in current listings, it usually means one of two things: the community genuinely does not carry shared amenities, or the listings active at this snapshot simply did not include that detail. Either way, the fix is the same: get the HOA documents or condo association details in hand before writing an offer.
The same caution applies to pricing. Without an established median or sales count to point to for Countryside Key Unit specifically, any pricing conversation here has to start with a direct comparable pull for the specific unit or lot in question, not a community-level average.
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.
Why work with Momentum here
This is exactly the kind of community where a thin public data set can lead a buyer or seller astray if they rely on aggregated numbers instead of the specific property. We pull HOA documents, association rules, and property-level comps directly rather than filling gaps with assumptions.
Countryside Key in 15 seconds.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- 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 all homes for sale in Oldsmar →
Should you buy in Countryside Key?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2006 (5 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 local comps.
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See how Countryside Key Unit fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Countryside Key
Where is Countryside Key?
Countryside Key is a community in Oldsmar, Pinellas County, Florida, ZIP 34677.
How many homes are in Countryside Key?
County property records list 21 homes in Countryside Key, built between 1995 and 1998; the typical home is about 1,110 heated square feet.
What do homes in Countryside Key sell for?
Countryside Key has no MLS sales in the last 12 months. The most recent year with recorded sales on file is 2024 (1 sale, median $270,000). For context, ZIP 34677 has 184 homes on the market with 21% under contract.
Are there homes for sale in Countryside Key right now?
No active listings inside Countryside Key at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Countryside Key have an HOA or CDD?
No HOA is on record for Countryside Key in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.
Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.
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