Neighborhood · Oldsmar, Florida
Countryside Key
Compact Oldsmar living close to Tampa's edge
2
Homes for sale
$252,250
Median list price
$228
Avg price / sqft
10
Median days on market
Countryside Key is a tidy, gated pocket of Oldsmar in northern Pinellas County, the kind of neighborhood where the floor plans are efficient and the commute math actually works. Homes here run smaller and smarter — a median of around 1,110 square feet — which appeals to buyers who want a manageable space near the East Lake corridor. You're a short hop from established neighbors like East Lake Woodlands and Country Club, with the golf-and-club scene of that area within easy reach.
The market reality is simple: inventory is thin. Right now there's a single active listing at $229,500, and over the past year 11 homes sold at a median of $235,000 — with sellers collecting about 97% of asking. When something comes up it tends to move fast (median one day on market), so pre-approval and a decisive plan matter here. Buyers comparing options should keep an eye on the broader Oldsmar homes for sale and nearby communities like Harbor Palms and Gull Aire Village.
Countryside Key is a community in Oldsmar, Florida.
Quick facts
$229,500 – $275K price range
1,108 sqft median home
$454/mo median HOA
$1,998/mo median rent
10 sold in 12 months
Drive times
On the market now
Homes for sale in Countryside Key
$229,500
366 COUNTRYSIDE KEY BOULEVARD, OLDSMAR
2 bd · 2.5 ba · 1,110 sqft
$275,000
279 COUNTRYSIDE KEY BOULEVARD, OLDSMAR
2 bd · 1.5 ba · 1,105 sqft
Every active listing inside the Countryside Key boundary
Open full map search →Find your fit
Browse Countryside Key
By feature — on the live map
The numbers that matter
The Countryside Key market
10
Sold, last 12 months
$235,000
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
66 days
Median time to sell
Countryside Key vs Oldsmar
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 14.3% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Countryside Key boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Countryside Key is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Countryside Key home
≈ $2,311/mo
$252,250 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$454/mo
Median HOA
From current listings inside the boundary
$1,998/mo
Median rent
Homes for rent inside the boundary
Population
384
Median age
48
Median income
$60,091
Median home value
$251,500
Beyond the listings
Living in Countryside Key
Entertainment
Top 4% in the U.S.Film Lovers
Movie buffs and binge watchers expressing their love for movies, storytelling, and the film making process.
Hobbies & Interests
Top 9% in the U.S.Engine Enthusiast
This population loves working on and showing off their cars, trucks and motorcycles. You can find them researching car shows and the hottest models on the lot.
Active
Top 11% in the U.S.Fitness Obsession
Passionate about strength training, this population relies heavily on the encouragement of the exercise community. While these people seek the latest fitness techniques, they're also interested in supplements and equipment.
Entertainment
Top 14% in the U.S.Competitive Nature
These folks have their head in the game. Whether it's creating a card game tournament with friends or cheering on the home team, these people want to win.
Active
Top 15% in the U.S.Functional Fitness
Looking good and reaching fitness goals is all about discipline: Eat right. Work hard. No excuses. This population is more likely to view working out as a means to an end.
Relationships
Top 15% in the U.S.Girl Squad
From girls night out to a movie night in with their closest gal pals, this population is all about getting the girls together for an evening of fun.
Straight answers
Countryside Key FAQs
Is Countryside Key a good place to live?+
It's a gated, low-maintenance neighborhood in northern Pinellas that works well for buyers who value a short commute and a manageable home size. Tampa International Airport is about 29 minutes out, and assigned schools include Curlew Creek Elementary, Joseph L. Carwise Middle, and East Lake High School. The nearby Country Club area adds a golf-and-club dimension to the surrounding lifestyle.
Is Countryside Key expensive?+
No — it's one of the more accessible pockets in the East Lake area, with a median list price of $229,500 and homes averaging about $207 per square foot. That's driven partly by smaller floor plans, with a median home size near 1,110 square feet. Compare it against the wider Oldsmar homes for sale to see where it fits your budget.
What do homes cost in Countryside Key?+
The single active listing is priced at $229,500, and over the past 12 months 11 homes sold at a median of $235,000. At roughly $207 per square foot, pricing reflects the neighborhood's compact, efficient layouts.
How is the market in Countryside Key?+
It's fast and tight. Homes have a median of just one day on market, only one is active right now, and sellers have been getting about 97% of asking over the past year. If you want to compete here, come pre-approved and ready to move quickly.
What are the HOA fees and property taxes like?+
The median HOA runs about $454 per month, which is typical for a gated community with shared maintenance. Median property taxes come in around $3,475 per year, and for renters the median rent is about $1,895 per month.
Keep exploring
More Oldsmar neighborhoods
Neighborhood boundary by edgeAI; listings matched to the polygon. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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