YOUR NEIGHBORHOOD GUIDE · OLDSMAR, FL

Get to know
Countryside Key.

Explore Countryside Key in Oldsmar, FL: nearby homes, schools and everyday places.

Find a local agent Explore the neighborhood ↓

Countryside Key Boulevard · Oldsmar

LIFE IN COUNTRYSIDE KEY

Get a feel for Countryside Key.

Countryside Key is a neighborhood in Oldsmar, FL. This guide brings together a housing snapshot and places to explore in and around the community.

LOCAL KNOWLEDGE MAKES A DIFFERENCE

Top real estate agents in Countryside Key

FastExpert agents

Ranked FastExpert agents serving Oldsmar, FL. Rankings are citywide, not specific to Countryside Key.

Vanessa Leonard

Keller Williams

Palm Harbor, FL

5.0 (140 reviews)

29 Years of Experience

Cynthia Fazzini

ReMax Realtec

Palm Harbor, FL

5.0 (37 reviews)

34 Years of Experience

Jennifer Richards

Homefront Realty

Dunedin, FL

5.0 (16 reviews)

18 Years of Experience

View all top agents in Oldsmar, FL

A LOOK AT THE MARKET

Homes & housing in Countryside Key

See homes for sale ↓

Median asking price$133,950Midpoint of listing prices

Asking price / sq ft—Median across listings with home size

Recorded sales · past year0Homes with a matching sale record

Nearby schools · estimatedB6.7/10 · 3 schools

Asking prices come from active listings. Recorded sales cover 2025-10-07 to 2026-10-07. A dash means that figure was not available.

What kinds of homes are here?

1 residential property records give a broader picture of Countryside Key, including homes that aren’t for sale.

Updated 2026-10-07. 39 land or other records are excluded from this housing mix. These are property classifications, not a census of individual homes.

Single-family · 1

How does Countryside Key compare?

Compare median asking prices across Oldsmar neighborhoods.

Median asking price from the discovery sample
Neighborhood	Median asking price	Compared with Countryside Key	Sale price / sq ft	Recorded sales
Countryside Key This neighborhood	$133,950	—	—	0
Oldsmar	$294,900	120% higher	—	3
Eastlake Oaks	$295,000	120% higher	—	1
Bay Arbor	$332,450	148% higher	—	3
Shoreview	$279,900	109% higher	—	2
West Oldsmar	$60,000	55% lower	—	2

Median asking price and price per square foot come from the same listing sample as the neighborhood cards. Recorded sales cover 2025-10-07 to 2026-10-07. A dash means that figure was not available.

Explore nearby neighborhoods in Oldsmar

Oldsmar ↗
Median asking price
$294,900
/ sq ft
—
Active listings
Not available
properties in discovery sample
98
B
Nearby schools · estimated
6.3/10 · 3 schools
Eastlake Oaks ↗
Median asking price
$295,000
/ sq ft
—
Active listings
Not available
properties in discovery sample
61
B
Nearby schools · estimated
6.3/10 · 3 schools
Bay Arbor ↗
Median asking price
$332,450
/ sq ft
—
Active listings
Not available
properties in discovery sample
60
B
Nearby schools · estimated
6.3/10 · 3 schools
Shoreview ↗
Median asking price
$279,900
/ sq ft
—
Active listings
Not available
properties in discovery sample
58
B
Nearby schools · estimated
6.3/10 · 3 schools
West Oldsmar ↗
Median asking price
$60,000
/ sq ft
—
Active listings
Not available
properties in discovery sample
21
B
Nearby schools · estimated
6.3/10 · 3 schools

Median asking price is the midpoint of listing prices in the discovery sample. A dash means that figure was not available. Photos show community or nearby landmarks.

See all featured Oldsmar neighborhoods →

MAKE TIME FOR OUTSIDE

Parks, lakes & recreation nearby

Find a place for a walk, a swim or an afternoon in the park. Some pools and lake facilities are private or for association members; check access before visiting.

Data not available for this view yet. Explore on Google Maps ↗

Places, ratings and photos from Google Maps. Saved results come from an approved snapshot. This page does not call Places API while you view it. Drives are estimates from Countryside Key’s center, without live traffic. Nearby results may extend beyond neighborhood boundaries.

YOUR EVERYDAY STOPS

Shopping & dining nearby

Discover restaurants for dining out and shopping centers in and around Countryside Key.

Restaurants for dining out, ranked using Google ratings and review counts. Fast-food and convenience-store results are filtered out.

Data not available for this view yet. Explore on Google Maps ↗

LEARNING CLOSE TO HOME

Nearby schools

Estimated grade B · 6.7/10

Public schools returned for sampled Countryside Key properties. Attendance depends on the specific address.

Loading map…

C marks Countryside Key’s center. Shading shows a half-mile radius around that point, not a neighborhood boundary. Numbered pins match the places below.

1Joseph L. Carwise Middle School6/10

2East Lake High School6/10

3Curlew Creek Elementary School8/10

School ratings · 2026-10-07. Grade methodology is below.

THE CITY AROUND YOU

Oldsmar demographics & households

Citywide context for a move to Countryside Key. These figures describe Oldsmar as a whole.

15,061Population

39.7Median Age

3.21Average family size

$57,283Median Household Income

66.6%Home Ownership

Explore Oldsmar’s age distribution

Median Age

39.7

Under 10 years old

11.1%

Age 10-19

12.2%

Age 20s

14.8%

Age 30s

12.4%

Age 40s

12.2%

Age 50s

16.4%

Age 60s

11.6%

Age 70s

5.9%

Age Over 80

3.4%

From FastExpert’s existing Oldsmar city-data source, retrieved 2026-10-07; source year was not supplied. Explore all Oldsmar city data →

FIND YOUR PLACE HERE

Homes for sale in Countryside Key

No listings returned by our provider right now. Explore current homes using the link above.

Listing data: Redfin. Photos and listing links: Redfin. Open a listing for its current status and full details.

KEEP EXPLORING

Get to know Oldsmar.

Explore the broader area’s housing and demographic context.

Explore Oldsmar city data →

Sources, dates & how we calculate estimates

Nearby places and photos come from an approved snapshot. Viewing this page does not call Google Places. A controlled refresh can still search within 5 km of the center. Recreation combines park, lake, trail and club searches, removes duplicates and keeps results within 5 miles. Restaurant ranking balances star ratings with review counts; fast-food, convenience stores and places marked as not offering dine-in are excluded.

Housing mix uses residential property records, including homes that are not for sale. Market prices use the most recent recorded qualifying sale per property within 2025-10-07 to 2026-10-07. Transfers identified as non-market transactions and records without a positive sale amount are excluded. Medians appear with at least 10 sales; price per square foot also requires a recorded home size. Property classifications and neighborhood definitions may differ from local usage. These are dated snapshots, not a complete transaction history or live inventory feed.

School grades are FastExpert estimates based on the mean available ratings for unique public schools found across 4 Countryside Key property samples: A = 8–10, B = 6–under 8, C = 4–under 6, D = 2–under 4, F = 1–under 2. Unrated schools are excluded. Grades do not confirm attendance eligibility.

Oldsmar demographics come from the existing FastExpert city-data source. The city’s source year was not supplied. Top agents use FastExpert’s existing Oldsmar ranking; a Countryside Key-specific ranking is not available yet.