Countryside Key
Homes for Sale in Oldsmar, FL
All 174 homes for sale in Oldsmar, FL · median $319,450 · 156 homes for sale in 34677 · Pinellas County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of October 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 157 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.
Recent Developments in Countryside Key Unit
Development, infrastructure, retail, and school activity affecting Countryside Key Unit, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated October 2026.
- October 2026Development
ClearView apartments complete at $1 billion Echelon City Center in St. Petersburg
The 363-unit ClearView community, with ground-floor retail, is complete within the Echelon City Center development by Third Lake Partners and Echelon. A 3rd & 3rd residential high-rise with ground-floor retail is expected to open in the first quarter of 2027.
What it may mean for the marketNew downtown apartments and walkable retail add rental inventory and amenities in central St. Petersburg. The project is about 24 miles southwest of Countryside Key Unit, elsewhere in Pinellas County.
Source: Tampa Bay Business and Wealth - August 2026Development
AECOM Hunt selected as construction manager for proposed $2.3 billion Rays ballpark in Tampa
AECOM Hunt joined the design team led by Populous for the proposed ballpark on a site that includes Hillsborough College property. The stadium would have at least 28,000 fixed seats, with a construction start targeted for September 2026 and completion by late 2028. Tampa's public contribution is up to $80 million and financing is not finalized.
What it may mean for the marketA large ballpark and surrounding mixed-use district would add construction jobs, event traffic and retail demand on the Dale Mabry corridor. The site is about 7 miles southwest of Countryside Key Unit.
Source: Tampa Bay Business and Wealth - August 2026Infrastructure
Four firms vie to build Tampa International Airport's $150 million control tower
TPA narrowed the field to four builders for a new blast-resistant air traffic control tower on about 2 acres northwest of the main terminal. The budget is about $150 million, with board selection expected Oct. 1 and substantial completion targeted for March 2029.
What it may mean for the marketAirport capital spending supports construction employment and long-term air service capacity for the region. The site is about 9 miles southwest of Countryside Key Unit.
Source: Tampa Bay Business and Wealth - July 2026Infrastructure
St. Pete approves temporary downtown dock for Tampa Bay ferry
The St. Petersburg City Council approved a temporary ferry dock on Bayshore Boulevard near the Vinoy in downtown St. Petersburg under a three-year contract costing about 324,200 dollars. Hubbard's Marina will operate cross bay service between downtown St. Petersburg and the Tampa Convention Center, with two vessels running year round. Service is expected to begin in October or November.
What it may mean for the marketEstablishes a temporary downtown dock and cross bay ferry connection, adding a new transit option and waterfront infrastructure serving the downtown St. Petersburg market. The project is about 23 miles southwest of Countryside Key Unit, elsewhere in Pinellas County.
Source: FOX 13 Tampa Bay - July 2026Development
St. Pete advances housing plan for nine vacant city lots
The St. Petersburg City Council unanimously approved a first reading of an ordinance to place a measure on the November 3 ballot that would remove nine vacant city lots in Methodist Town from the city's Charter Park and Waterfront Map. The change would allow up to 41 units of affordable or workforce housing, with four lots planned for single family homes and five larger parcels for multifamily housing. The lots have held park designations since 1984 but have remained vacant.
What it may mean for the marketAdvances a plan to convert nine vacant city lots into new single family and multifamily housing, adding to local housing inventory. Placing the parcels on the ballot could open long dormant land for residential construction. The project is about 24 miles southwest of Countryside Key Unit, elsewhere in Pinellas County.
Source: St Pete Catalyst - July 2026Development
Blake-Related team selected to redevelop 86-acre Historic Gas Plant District
St. Petersburg selected a bid led by Blake Investment Partners, with the Related Group as co-developer, to redevelop the 86-acre Historic Gas Plant District at the Tropicana Field site. The roughly 8.1 billion dollar mixed use plan calls for more than 3,600 income-restricted residential units, a 13-acre central park, and office, retail, hotel and civic space over an estimated 20-year buildout. The developers plan to purchase about 58 acres while the city retains roughly one third.
What it may mean for the marketAdds a large mixed use district with thousands of new residential units, a central park, and office, retail, hotel and civic space to the downtown St. Petersburg market. Redevelopment of the Tropicana Field site reshapes the surrounding property landscape and expands housing supply. The project is about 24 miles southwest of Countryside Key Unit, elsewhere in Pinellas County.
Source: Florida YIMBY
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.
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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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