Countryside Key
Homes for Sale in Oldsmar, FL
All 178 homes for sale in Oldsmar, FL · median $333,500 · 18 townhomes for sale in Oldsmar · 149 homes for sale in 34677 · Pinellas County homes for sale
True comps, carrying-cost math, and listings before the portals.
Market Heat
As of October 2026, Countryside Key in Oldsmar, FL has 2 homes for sale. Over the 12 months ending 2026-09-20, 10 recorded sales closed at a median of $235,000, $212 per square foot, a median 66 days on market, sellers accepting 93% of original asking (-14% versus the prior year). Homes listed or recently sold were built 1995 - 1998; 12 of 13 report an HOA (median $433/mo); none of the 13 geocoded homes sit in a FEMA special flood hazard zone (median elevation 14 ft). At the median price and Pinellas County's FY2025-26 rate of 19.39 mills, annual property tax runs about $4,560 ($3,740 with the full homestead exemption).
Countryside Key right now
🟡 Balanced market. 1.8 months of supply and 0% of the inventory already under contract put buyers and sellers on roughly even footing.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Stellar MLS records, as of September 20, 2026. Confidence: Medium (2 active and pending listings, 10 closed sales in 12 months).
🔴 Off the recent peak. The trailing-12-month median ($235K) is down 14.2% from the prior 12 months ($274K). 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 September 20. Confidence: Medium (10 and 9 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 24, 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 September 20, 2026): the median sale price is about $235K ($212 per sq ft over the trailing 12 months of closed sales), a median 66 days on market for closed sales, and 1.8 months of supply, a balanced market. 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).
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.
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.
The setting & the homes.
Aerial and on-site photos of Countryside Key. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 20 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 ($274K) IS the -14.2% 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.
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Pinellas 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 · Pinellas 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.
Countryside Key Market Scorecard
Countryside Key is currently a strong seller's market. About 2.2 months of supply, a median asking price of $252,250, and homes go under contract in about 72 days.
Typical home value in the 34677 ZIP is $358,138, about 15.3% below the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · 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.
Homes For Sale Right Now in Countryside Key
Live MLS inventory for Countryside Key. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active and pending Countryside Key listings as of 2026-10-23, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2004 through 2026. Tap any home to ask about it.
Countryside Key on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap contributors.
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.
Recent Developments in Countryside Key
Development, infrastructure, retail, and school activity affecting Countryside Key, 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 19 miles south of Countryside Key, elsewhere in Pinellas County.
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 11 miles southeast of Countryside Key.
Source: Tampa Bay Business and Wealth - 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 19 miles south of Countryside Key, elsewhere in Pinellas County.
Source: St Pete Catalyst - 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 19 miles south of Countryside Key, elsewhere in Pinellas County.
Source: FOX 13 Tampa Bay - 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 20 miles south of Countryside Key, 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.
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.
Inventory runs at 1.8 months of supply, a balanced market and the trailing-12-month median down 14% year over year. Homes that do trade take a median 66 days on market, useful leverage on any listing that has lingered.
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 (5.2). Basis: Recent Direction -14.2% year-over-year; Liquidity & Demand 1.8 months of supply; Pricing Power 92.6% sale-to-list. Refreshed with each data update.
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 →
| Location | Oldsmar, Pinellas County, FL · ZIP 34677 |
|---|---|
| Home types (current listings and sales) | townhouses 100% |
| Amenities listed by sellers | Gated Community - No Guard, Pool, Tennis Court(s), Deed Restrictions, Buyer Approval Required, Gated Community |
| Sale prices, last 12 months | $235,000 median across 10 closed sales · $212 per sq ft · -14.2% vs the prior 12 months |
| Days on market (closed sales) | 66 median |
| For sale right now | 2 active, 0 pending · median asking $252,250 · 1.8 months of supply |
| Zoned public schools | Pinellas County Schools (verify by address); Confirm zoned elementary, middle, and high |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2004 through 2026. Market figures describe homes, not residents. Cite as: Momentum Realty, “Countryside Key key facts,” movewithmomentum.com/neighborhoods/countryside-key, data as of September 20, 2026.
Housing distress & ownership in Countryside Key, Oldsmar
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 October 2026 through October 2026. Deemed reliable but not guaranteed.
Just listed in Countryside Key
The newest homes for sale in Countryside Key right now, newest first. Each link opens the full listing with every photo, the price history and a tour request.
- 279 Countryside Key Boulevard $275,000 · 2 bd · 1.5 ba · 1,105 sq ft · listed Aug 27, 2026 Courtesy of REAL ESTATE FIRM OF FLORIDA, LLC
- 366 Countryside Key Boulevard $229,500 · 2 bd · 2.5 ba · 1,110 sq ft · listed Jul 31, 2026 Courtesy of CENTURY 21 INTEGRA
Checked against the MLS nightly. All new listings in this market.
Every Home for Sale in Countryside Key Right Now (2)
All 2 active and pending Countryside Key listings with a detail page, newest first, refreshed twice a day from the MLS.
- 366 Countryside Key Boulevard · $229,500 · 2 bd / 2.5 ba · listed Sep 10, 2026 · listed by Century 21 Integra
- 279 Countryside Key Boulevard · $275,000 · 2 bd / 1.5 ba · listed Sep 4, 2026 · listed by Real Estate Firm Of Florida, Llc
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Oldsmar guides & data
- Market data
- Cost of living
- Best neighborhoods
- Property taxes (Pinellas County)
- Homestead exemption (Pinellas County)
- Home insurance cost
- New construction (Pinellas County)
- Gated communities guide
Florida buyer guides
Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- Countryside Key Boulevard (128 homes on record)
- Countryside Key Boulevard (10 homes on record)
- Countryside Key Boulevard (4 homes on record)
- Countryside Key Boulevard (4 homes on record)
- Countryside Key Boulevard (3 homes on record)
- Countryside Key Boulevard (2 homes on record)
What it really costs to own in Countryside Key
The parts of the monthly number a mortgage calculator leaves out, from the tax roll, the MLS, Citizens and FEMA. Property facts only.
| HOA dues | Median $433/month across 12 MLS listings (most billed monthly; 2026-10-24). Dues cover what the documents say they cover; ask for the budget and reserve study. |
|---|---|
| Home and flood insurance | The average Citizens Property Insurance premium in Pinellas County is $1,911/yr (20,791 policies, Citizens detail by county, April 2026); private-market quotes depend on roof age, wind mitigation and construction. |
| Roof and age | Median build year 1997 across 13 listings. An original roof here would be about 29 years old; under Florida's 2022 reform (SB 2-D) carriers may require an inspection past 15 years, so budget for a roof report, and for replacement where it fails. |
Email me new listings in Countryside Key
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 Countryside Key
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Countryside Key will answer, and the answer is published on this page for the next buyer.
Frequently Asked Questions
What is the median home price in Countryside Key?
How long do homes in Countryside Key take to sell?
Is Countryside Key a buyer's or seller's market right now?
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?
Where is Countryside Key, and what county is it in?
Is Countryside Key a good place to live?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 23, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 20, 2026 |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Schools | 2025-26 district assignments + FLDOE school grades; verify with the district |
| Historical depth | Closed-sale records back to 2004 (103 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.
Looking to buy here? Search homes for sale →
What’s your home worth in your area?
A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Countryside Key fits the bigger picture — live prices, inventory, and Momentum Scores:
More on Countryside Key
- Home values · What homes in Countryside Key actually sell for
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