Countryside Key in Oldsmar

Countryside Key Homes for Sale in Oldsmar, FL

Gated townhome community · Oldsmar, Pinellas County · ZIP 34677

A gated, guard-staffed townhome community in Oldsmar, a pool and tennis near Tampa Road.

Gated, 24-hour guardPool and tennisMaintenance-inclusive HOA
Live Market Pulse
50/100
Momentum
Buyer-Leaning Market (limited data)
Countryside Key is a gated, maintenance-inclusive townhome community, so the unit, the position, and the HOA, not a community average, decide the buy.
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Listings before the portals, true comps, and the renovation and carrying-cost math, before you tour.

Built fromLive Stellar MLS data14 years of closingsLocal renovation analysisUpdated twice daily
LiveMarket PulseStellar MLS
n/a
Median Price
0mo
Supply
n/a
Avg DOM
Soft
Seller Leverage
n/a
Median $/Sqft
n/a
1-Yr Price Change
0now
Distress
Jon Brooks, founder of Momentum Realty
Jon's Current Read

"Countryside Key is a gated, guard-staffed townhome community in Oldsmar built in the mid-to-late 1990s, so the read is by unit and position rather than one number: two-story block and frame townhomes of roughly 1,100 to 1,300 square feet, two to three bedrooms, sharing a pool, tennis, and a duck pond behind a 24-hour guard, with a maintenance-inclusive HOA. The unit, the position, the condition, and the HOA inclusions drive value. Your leverage is matching the unit and position to real comps and reading what the HOA covers, with the gated, low-maintenance Oldsmar location as the draw."

Jon Brooks, founder, Momentum Realty · Updated June 2026

The 60-Second Overview

Countryside Key is a gated townhome community in Oldsmar, Pinellas County, built between 1995 and 1998 near Tampa Road and the Countryside area (community and listing sources, 2026).

Homes are two-story block, stucco, and wood-frame townhomes of roughly 1,105 to 1,285 square feet, in two-bedroom and three-bedroom plans. The gated community has a pool, tennis courts, and a duck pond, with a 24-hour guard. The HOA, recently in the mid-four-hundreds monthly, is broadly inclusive, covering common-area and building maintenance, the community roads, the pool, the guard, water, sewer, trash, pest control, cable, and internet.

This is an established, maintenance-inclusive gated townhome market, so the money is made or lost on the unit, the position, the condition, and the HOA inclusions, not the headline price.

The pitch is gated, low-maintenance Oldsmar living with a pool and tennis behind a guard, near Tampa Road shopping and the Countryside area. The work is sorting the unit and position, reading exactly what the HOA covers, judging condition, and pricing against real comps before you offer.

Best for

  • Buyers who want a gated, low-maintenance townhome with a guard
  • Buyers who value a maintenance-inclusive HOA
  • Downsizers and lock-and-leave buyers
  • Buyers who want a convenient Oldsmar and Countryside location

Probably not for

  • Buyers who want a detached single-family home with a yard
  • Anyone who wants a no-HOA, low-fee structure
  • Buyers who want new construction with a warranty
  • Buyers who want a large private lot

How Countryside Key is performing right now

50/100
momentum
Buyer-Leaning Market (limited data)
Seller's marketBalancedBuyer's market
0Months of supplytight
72Median days on marketdays
0 : 0Under contract vs for salestrong demand
0Sold in last 12 monthsliquidity
+0%Asking vs recent sold $/sqftroom to negotiate

Tight supply and strong demand favor sellers here. Homes still take about two months to sell, though, and with asking prices running above recent sales per square foot, a prepared buyer has room on anything overpriced. Reading each home against the real comps, not the headline trend, is where the edge is.

Live from Stellar MLS, as of June 24, 2026. Refreshed twice daily. Months of supply, days on market, and the contract-to-listing ratio are computed from current Countryside Key listings and the trailing twelve months of closed sales.

8.6A- score
Momentum intelligence
Momentum buy score

Our proprietary read on how a home in Countryside Key buys, holds, and resells. See the five factors.

Listing locations from Stellar MLS; lot type inferred from listing descriptions. Destination pins are approximate. Map data © OpenStreetMap, tiles © CARTO. Flood, school, and commute overlays are on the roadmap.

The Club & Membership

15-Second Take
  • A community pool and tennis courts
  • A duck pond within the gates
  • A 24-hour guard and gated entry
  • A broadly inclusive HOA
  • Funded through the maintenance-inclusive fee

Countryside Key is a gated, guard-staffed townhome community in Oldsmar built between 1995 and 1998, near Tampa Road and the Countryside area. It centers on a community pool, tennis courts, and a duck pond behind a 24-hour guard, with two-story block and frame townhomes of roughly 1,105 to 1,285 square feet in two- and three-bedroom plans. The HOA is broadly inclusive, covering building and common-area maintenance, the roads, the pool, the guard, water, sewer, trash, pest control, cable, and internet. Because the inclusive fee and the gated amenities are central, confirm the unit and position, the HOA inclusions and reserves, and the home's condition before you buy.

The takeaway

Countryside Key pairs a gated, guard-staffed townhome with a pool and tennis near Tampa Road and the Countryside area, the low-maintenance value case in Oldsmar.

Tampa Road~2 to 5 min · main corridor
Westfield Countryside (Clearwater)~5 to 12 min · retail
Downtown Oldsmar~5 to 10 min · shops and dining
Tampa International Airport~20 to 30 min · via Courtney Campbell
Honeymoon Island and the Gulf~20 to 30 min · beaches
Downtown Tampa~30 to 40 min · via Courtney Campbell
Pinellas Trail~5 to 12 min · biking and walking

Distances and drive times are approximate and vary with traffic. Confirm your real commute at your real departure time.

Nearby Communities

Explore more neighborhoods near Countryside Key Homes for Sale in Oldsmar, FL with Momentum Realty’s local guides.

BABay Arbor Homes for Sale in Oldsmar, FLOldsmar, FL · 0.2 miELEast Lake WoodlandsWoods Landing Townhomes in Oldsmar, FLOldsmar, FL · 0.4 miOCOldsmar CountryClub Estates Homes for SaleOldsmar, FL · 0.6 miEBEmerald Bay Homes for Sale in Oldsmar, FLOldsmar, FL · 0.7 miBMBayside Meadows Homes for Sale in Oldsmar, FLOldsmar, FL · 0.7 miOHOldsmar Homes for SaleOldsmar, FL · 0.8 miWOWest Oldsmar Homes for SaleOldsmar, FL · 0.9 miGAGull-Aire Village Homes for Sale in Oldsmar, FLOldsmar, FL · 0.9 miWOWoods ofForest Lakes Homes for Sale in Oldsmar, FLOldsmar, FL · 0.9 mi

Browse all Florida neighborhood guides →

Carrying cost · the no-CDD edge

No CDD bond means thousands less per year than newer master plans.

Typical CDD community~$2,500/yr
Countryside Key (no CDD)$0/yr

Roughly $25,000 saved over 10 years in carrying cost, before resale.

Illustrative. NE Florida CDD assessments commonly run $1,500-$3,500+/yr and vary by community; verify per property.

Schools

15-Second Take
  • Pinellas County Public Schools
  • Verify the zoned schools by address
  • Magnet and choice options may be available
  • Confirm current ratings before relying on them
  • Private and parochial options nearby

Countryside Key is served by Pinellas County Public Schools. Assignment is by address and can change, so confirm the exact zoned elementary, middle, and high schools for any specific home, plus any magnet or choice options. Treat published ratings as a starting point, not the full story.

Public

Pinellas County Schools (verify by address)

Verifyrating
By address

Confirm zoned elementary, middle, and high

Verifyrating

Buying with schools in mind? We can confirm the exact zoned schools for any Countryside Key address.

The takeaway

What is actually shaping value at Countryside Key: steady demand for gated, low-maintenance product, the broadly inclusive HOA, and the condition dynamics of mid-1990s stock. Each item is sourced and linked.

Recent Developments in Countryside Key

Our read on what is being built around Countryside Key, scored for direction, significance, and how close the effect lands. The full sourced timeline follows below.

Net OutlookBullishThe gated, guard-staffed, inclusive-HOA format supports steady interest, with the watch items being older-stock condition and HOA reserves.

Gated, guard-staffed community

Ongoing
BullishNotable impact
SignificanceRadius: Community

A 24-hour guard and gated entry anchor the security and low-maintenance value buyers pay for.

Broadly inclusive HOA

Ongoing
BullishNotable impact
SignificanceRadius: Community

An HOA covering building maintenance, the pool, the guard, and utilities simplifies carrying costs for many buyers.

Pool, tennis, and duck pond

Ongoing
BullishNotable impact
SignificanceRadius: Community

A pool, tennis, and a duck pond add amenity value within the gates.

Convenient Oldsmar location

Ongoing
BullishNotable impact
SignificanceRadius: Area

A location near Tampa Road and the Countryside area supports demand among low-maintenance buyers.

Mid-1990s housing stock

Ongoing
NeutralNotable impact
SignificanceRadius: Community

Mid-1990s product means roof, systems, and updates are the swing factor, read unit by unit.

HOA reserves

Ongoing
NeutralMinor impact
SignificanceRadius: Community

On older stock with an inclusive fee, the reserve picture matters and should be verified per unit.

Direction, significance, and effect-radius ratings are Momentum's proprietary, qualitative read of the sourced items below, not investment advice or a prediction for any specific home.

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 June 2026.

Showing the latest, scroll for all updates ↓

  1. January 2026
    Market

    Countryside Key remains a gated Oldsmar townhome community

    Countryside Key is described as a gated Oldsmar townhome community built between 1995 and 1998 with two-story block and frame townhomes of roughly 1,100 to 1,300 square feet, a pool, tennis, a duck pond, and a 24-hour guard. Why it matters: A gated, guard-staffed, low-maintenance format keeps the community in steady demand. Source

  2. January 2025
    Community

    Countryside Key carries a broadly inclusive HOA

    Listing profiles describe the Countryside Key HOA as covering building and common-area maintenance, the roads, the pool, the guard, water, sewer, trash, pest control, cable, and internet in the gated Oldsmar community. Why it matters: The inclusive HOA is central to the value and must be verified per unit. Source

Development alerts for Countryside KeyGet a short monthly email when something new is approved, funded, or opens near Countryside Key.

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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.

If we were buying in Countryside Key, this is the order of operations we would run, and the one we run for our clients.

1

Pick the unit and position first. Countryside Key spans unit positions, which trade differently for light, view, and quiet.

2

Read exactly what the HOA covers. The fee is broadly inclusive, so confirm the inclusions, the reserves, and any rental restrictions.

3

Judge the home by condition. On mid-1990s stock, read the roof, systems, and any updates for the specific unit.

4

Confirm the gated and amenity standing. Verify the guard, pool, and tennis are well funded in the budget.

5

Use the Oldsmar context, and cross-shop other east-lake options such as East Lake Woodlands.

Best Buy
A well-kept unit in a quiet, well-positioned spot matched to comps
Biggest Risk
Underreading the HOA reserves and the unit position
Best Lot
A pond-view or quiet interior position over a parking-facing one
Smart Timing
Confirm the HOA inclusions and reserves before you offer
The takeaway

On mobile, tap any heading below to open it. This is the home by home, lot by lot, club and renovation detail, organized so you can jump straight to what matters to you.

Community Details at a Glance

The Homes

Type

Two-story townhomes

Size

Roughly 1,105 to 1,285 sq ft

Bedrooms

Two and three bedrooms

Era

Built 1995-1998

Costs & Fees

HOA

Broadly inclusive, mid-four-hundreds

Includes

Maintenance, pool, guard, utilities, cable

Worth noting

Verify inclusions, reserves, and rental rules

Amenities

Pool

Community pool

Courts

Tennis courts

Gated

24-hour guard and duck pond

Location

Near Tampa Road and Countryside

Location

Area

Oldsmar, Pinellas County, ZIP 34677

Access

Tampa Road and Courtney Campbell

Nearby

Countryside, the airport, and the Gulf

The takeaway

Three honest price bands. Condition and lot, not the square footage alone, decide where a home lands.

The Two-Bedroom Entry

The smaller two-bedroom plans, the attainable way into the gated, guard-staffed community.

Lowest entry
The Three-Bedroom Core

The larger three-bedroom plans, the heart of the resale market here.

Most inventory
The Top

The most updated units in the best, pond-view or quiet positions, the ones that hold value best.

Strongest resale

Approximate 2026 resale bands from third-party listing data and public records, not NEFAR statistics. Confirm pricing for a specific home.

The Two-Bedroom Entry
The smaller two-bedroom plans, the attainable way into the gated, guard-staffed community.
The Three-Bedroom Core
The larger three-bedroom plans, the heart of the resale market here.
The Top
The most updated units in the best, pond-view or quiet positions, the ones that hold value best.

Approximate 2026 resale bands from third-party listing data and public records, not NEFAR statistics. Confirm pricing for a specific home.

15-Second Take
  • Renovation math decides the deal
  • Golf and lake lots resell strongest
  • Roof and HVAC age drive the insurance quote
  • Interior lots are where buyers overpay
Jon Brooks, Momentum Realty
Operator Note

Most buyers overpay on interior lots in the back half of the community. A sharp renovation can distract you, but the weaker resale position follows the lot, not the finishes. We read the homesite before the kitchen.

Location within OldsmarStrong
Established communityPositive
HOA and CDD postureConfirm per parcel
Home condition and systemsVerify per home
Flood read per lotVerify per address

Momentum analysis based on the no-CDD structure, central location, built-out lot scarcity, the funded club plan, and the all-resale 1990s housing stock. Not a guarantee of future value.

Jon Brooks, Momentum Realty
Operator Note

The strongest value pocket is usually a renovated golf or lake home priced just under the next tier up. Buyers chasing the single biggest estate often pay estate prices for what is really a renovation project.

5 Mistakes Buyers Make in Countryside Key

15-Second Take
  • Calling the listing agent (who works for the seller)
  • Misjudging the renovation budget
  • Overpaying for an interior lot
  • Ignoring the optional club cost
  • Skipping the roof, HVAC, and systems check

In an all-resale, seven-figure, renovation-driven market, the same five mistakes cost buyers the most. Every one is avoidable with the right preparation before you tour.

The gates, the guard, the pool, and the inclusive HOA are priced into every unit. The deal is won or lost on the unit, the position, and the condition versus real comps.

Jon Brooks · Founder, Momentum Realty
7.0B · Buy Score
Resale Strength6.8/10
Renovation Risk4.4/10
Location Efficiency7.4/10
Long-Term Defensibility7.2/10
Carrying Cost Advantage5.8/10

Momentum Intelligence Scores are our proprietary, qualitative assessment based on the analysis on this page, on a 0 to 10 scale. They are a framework for comparing communities, not a guarantee of future value or advice on a specific home.

Why our read on Countryside Key is different.

Most pages on this community are an automated estimate wrapped in stock copy. This one is built from the live Stellar MLS feed, fourteen years of closed sales, and a renovation-by-renovation read of what actually moves value here, lot by lot. No Zestimate, no guesswork.

Live Stellar MLS feed14 years of closed salesRenovation-premium analysisLot-by-lot, no automated estimates
Jon Brooks, founder of Momentum Realty. A housing economist with a background in real estate investment banking at Deutsche Bank and consulting at Ernst & Young, who has built and analyzed Northeast Florida real estate from the ground up.

Which Lots & Views Hold Value Best

Where the value actually sits. Each home is shaded by its price per square foot (a value read, not just a price) and ringed by lot type, so you can see at a glance which pockets carry a real, durable premium and where a renovation play makes sense.

Value ($/sqft)
$261 value$401 premium
Lake / waterPreserveInterior

Fill = price per square foot; ring = lot type, inferred from listing descriptions. Sold homes are shown by realized $/sqft (lot type not always recorded). Asking and recent-sold figures from Stellar MLS; for orientation, not an appraisal.

15-Second Take
  • Pond-view and quiet positions hold value best
  • Parking-facing positions trade at a discount
  • The inclusive HOA covers many bills
  • Reserves matter on mid-1990s stock
  • Read the position and condition before the finishes

In a gated, maintenance-inclusive townhome community, the unit, the position, and the HOA are the part of your money the market protects. Well-kept units in quiet, pond-view positions hold value better than parking-facing or dated units, and the gates, the guard, the pool, and the inclusive HOA are durable draws. The home can be updated; the gated, guard-staffed setting cannot. Read the position and the HOA inclusions and reserves first, then price the condition against comparable townhome sales.

Countryside Key in 15 seconds.

Best forBuyers who want a gated, low-maintenance Oldsmar townhome with a guard, pool, and tennis.
Biggest advantageA 24-hour guard, pool, tennis, and a broadly inclusive HOA in a convenient location.
Biggest riskMid-1990s condition and HOA reserves to verify per unit.
Sweet spotA well-kept unit in a quiet, well-positioned spot, matched to comps.
Avoid ifYou want a detached home with a yard, a low-fee structure, or new construction.

HOA, Fees & What It Covers

15-Second Take
  • A broadly inclusive HOA covers most of the bills
  • Building maintenance, pool, and guard included
  • Water, sewer, trash, cable, and internet included
  • Reserves matter on mid-1990s stock
  • Confirm the fee, inclusions, and rules per unit

Countryside Key carries a broadly inclusive HOA, recently in the mid-four-hundreds monthly, that has covered common-area and building maintenance, the community roads, the pool, the 24-hour guard, water, sewer, trash, pest control, cable, and internet. Confirm the current fee, the exact inclusions, the reserves, and any rental restrictions for the specific unit, because the inclusive fee is central to the value.

The HOA funds building and common-area maintenance, the roads, the pool, the guard, water, sewer, trash, pest control, cable, and internet. Verify the exact amount, the inclusions, and the reserves for the specific unit.

The takeaway

Selling here is won on condition and view, not the Zestimate. The right number comes from closed comps matched to your renovation level and lot.

Momentum listings (YTD)
97.98%
Sold-to-list ratio across our market for our agents, sellers keeping more of their price.
Market average (YTD)
96.73%
The broader metro average sold-to-list ratio over the same period.
Momentum days on market
64 days
Median days on market for our listings, faster sales mean less carrying cost and stronger leverage.
Market days on market
72 days
The broader metro median over the same period.

Sold-to-list and days-on-market figures reflect Momentum Realty listings versus our market average, year to date. Your home's result depends on pricing, condition, lot, view, and preparation.

In Countryside Key, condition and view decide your number

Because buyers here are weighing your home against renovated comps and cross-shopping East Lake Woodlands, a home priced to the community average instead of its true condition and view either leaves money on the table or sits. A renovated kitchen, newer roof and HVAC, and a golf or lake view all deserve to show up in your price, and a buyer pool reading renovation math needs to be shown why your home is worth it. We build that case with real comps and a pricing strategy for the current market.

What is your Countryside Key home worth?

Get a no-obligation home value based on real comparable sales in Countryside Key matched to your condition, lot, and view, 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 homes for sale in Countryside Key on the map →
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Real comps, not a Zestimate.

Countryside Key Market Scorecard

Strong seller's market

Countryside Key is currently a strong seller's market. About 1.8 months of supply, a median asking price of $1,019,500, and homes go under contract in about 79 days.

1.8
Months supply
$1,019,500
Median list
$847,500
Median sold
$313
Per sqft
79
Days on mkt
6/8/41
Active/Pend/Sold

Typical home value in the 32224 ZIP is $456,759, about 13.7% above the Florida norm (Zillow Home Value Index).

Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.

Live data: Stellar MLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.

Frequently Asked Questions

Where is Countryside Key?
Countryside Key is a gated townhome community in Oldsmar, Pinellas County, near Tampa Road and the Countryside area, ZIP 34677.
What kind of homes are in Countryside Key?
Two-story block, stucco, and wood-frame townhomes of roughly 1,105 to 1,285 square feet, in two- and three-bedroom plans, built between 1995 and 1998.
Is Countryside Key gated?
Yes. It is a gated community with a 24-hour guard, a pool, tennis courts, and a duck pond.
What does the Countryside Key HOA cover?
The broadly inclusive HOA has covered common-area and building maintenance, the roads, the pool, the guard, water, sewer, trash, pest control, cable, and internet. Confirm the current fee and inclusions for the specific unit.
What amenities does Countryside Key have?
A community pool, tennis courts, a duck pond, and a 24-hour guard, near Tampa Road shopping.
What schools serve Countryside Key?
It is part of Pinellas County Schools. Assignment is by address and can change, so confirm the exact zoned schools.
Are rentals allowed at Countryside Key?
Rentals have been available in the community; confirm the current rental restrictions and any minimum lease terms with the association for the specific unit.
Is Countryside Key new construction?
No. It is an established community built between 1995 and 1998, so read each unit's condition.
Does Countryside Key flood?
Exposure is parcel specific. Run the FEMA flood zone and an insurance quote for the exact address.
Is Countryside Key a good value?
A gated, guard-staffed, low-maintenance townhome with an inclusive HOA in a convenient Oldsmar location supports demand, with value driven by the unit, position, condition, and HOA inclusions. This is not a guarantee of future value.
What should I check before buying in Countryside Key?
The unit and position, the HOA fee, inclusions, reserves, and rental rules, the home's condition, and the flood zone.
Buyers who want a gated, low-maintenance townhome with a guardExcellent fit
Buyers who value a maintenance-inclusive HOAExcellent fit
Downsizers and lock-and-leave buyersExcellent fit
Buyers who want a convenient Oldsmar and Countryside locationExcellent fit
Buyers who will verify the HOA inclusions and reservesExcellent fit
Buyers who want a detached single-family home with a yardProbably not
Anyone who wants a no-HOA, low-fee structureProbably not
Buyers who want new construction with a warrantyProbably not
Buyers who want a large private lotProbably not
Buyers unwilling to read condition on mid-1990s stockProbably not

Get the inside read on Countryside Key

Whether you are buying a renovation project, comparing the lots and views, weighing the optional club, or selling your Countryside Key home, tell us what you need. Every inquiry comes straight to us. We represent you, not the seller, and what your agent is paid is negotiable and set in a written buyer agreement up front. No obligation, no spam, no high-pressure follow-up.

We respond personally, usually the same day.

You are all set.

A Momentum Realty Countryside Key specialist will reach out personally, usually the same day.

Thinking about hiring an agent here? How to find the best real estate agent in Countryside Key — what to look for, questions to ask, and your local expert.
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Photography on this page is sourced from active and recently sold MLS listings in this community and remains the property of the listing brokerage and/or photographer. Listings courtesy of Stellar MLS as distributed by MLS GRID. 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; deemed reliable but not guaranteed by MLS GRID.

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