366 COUNTRYSIDE KEY BOULEVARD, OLDSMAR, FL, 34677
Active1 days on marketListed Jul 31, 2026MLS #TB8534362
About this home
366 COUNTRYSIDE KEY BOULEVARD
Welcome to this 2-bedroom, 2.5-bath townhome located in the desirable gated community of Countryside Key in the heart of Oldsmar. This spacious floor plan features two primary suites upstairs, each with its own private bathroom, while the convenient half bath downstairs is perfect for guests. Enjoy an open living and dining area with plenty of natural light and a private screened patio ideal for relaxing or entertaining. The seller is offering a concession toward new flooring and/or appliances, providing a great opportunity to personalize the home to your own style. Residents of Countryside Key enjoy access to a community pool, tennis courts, and beautifully maintained grounds, all just minutes from shopping, dining, parks, top-rated schools, Tampa International Airport, and the beaches.
Facts & features
The home at a glance
2
Bedrooms
2.5
Bathrooms
1,110
Sqft
0.02 ac
Lot size
1997
Year built
Two
Levels
$207
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record and the real association fee — not generic estimates.
$2,356 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
Estimated payment
$2,356/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
−4%
$/sqft vs Oldsmar actives
$207 vs $229
Days on market
1 vs 43 typical
Where $207/sqft sits among the 148 Oldsmar actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Countryside Key
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Oldsmar. See the full Oldsmar guide →
Countryside Key — neighborhood snapshot
Population
384
Median age
48
Median income
$60,091
Median home value
$251,500
Avg household
2
Households w/ children
35%
For the school run
Pinellas County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Oldsmar market
$360K → $355K
Oldsmar median sold, yr/yr
96.3%
Sale-to-list ratio (12 mo)
95 of 148
Oldsmar actives have cut their price
Median sold price, Oldsmar, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 8% below the OLDSMAR 34677 median. See the full Oldsmar market guide →
Paper trail
This home's history
Reality check
What actually sold near 366 COUNTRYSIDE KEY BOULEVARD
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Sep ’25$227,500
309 COUNTRYSIDE KEY BOULEVARD · same community
2 bd · 2.5 ba · 1,110 sqft · $205/sqft · 101 DOM
Sold · Mar ’26$235,000
273 COUNTRYSIDE KEY BOULEVARD UNIT N/A · same community
2 bd · 2.5 ba · 1,110 sqft · $212/sqft · 117 DOM
Sold · Jul ’26$191,000
244 COUNTRYSIDE KEY BOULEVARD · same community
2 bd · 2.5 ba · 1,110 sqft · $172/sqft · 160 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
Rui Ma
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 366 COUNTRYSIDE KEY BOULEVARD — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 366 COUNTRYSIDE KEY BOULEVARD — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to Rui's phone and CRM.
Straight answers
366 COUNTRYSIDE KEY BOULEVARD FAQs
What would the monthly payment be for 366 COUNTRYSIDE KEY BOULEVARD?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $2,356/mo — principal and interest, the actual property-tax bill, the $454/mo association fee and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
How much are the HOA fees at 366 COUNTRYSIDE KEY BOULEVARD?+
The association fee works out to $454 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 366 COUNTRYSIDE KEY BOULEVARD?+
The most recent tax bill on record (2025) was $3,475. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 366 COUNTRYSIDE KEY BOULEVARD?+
The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Oldsmar?+
At $229,500, this home is listed about 33% below the Oldsmar median of $342,450. The market section on this page shows how the area is trending.
Which schools are assigned to 366 COUNTRYSIDE KEY BOULEVARD?+
Curlew Creek Elementary School (elementary), Joseph L. Carwise Middle School (middle), East Lake High School (high) — Pinellas County School District. Always verify school assignments with the district before relying on them.
The brief
Four things that matter here
01Under the OLDSMAR 34677 market on paper
$229,500 is 8% below the OLDSMAR 34677 median of $249,000, and at $207/sqft it sits under the Oldsmar average of $246.
02Water views
The water view is part of what you're buying — views hold value independently of the structure.
03Fresh on the market
Only 1 day on market in a Oldsmar market that averages 43 — if it fits, move quickly.
04Strong assigned schools
Curlew Creek Elementary School, Joseph L. Carwise Middle School, East Lake High School — Curlew Creek Elementary School rates 4 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of CENTURY 21 INTEGRA · Becki Server. MLS #TB8534362.
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.
Never miss a listing
New Oldsmar homes, in your inbox
Like 366 COUNTRYSIDE KEY BOULEVARD but not quite? A daily digest of every new listing in Oldsmar — straight from the MLS, hours after it goes live. Unsubscribe anytime.
Just watching this one home? Ask Rui to ping you on any price or status change →