279 COUNTRYSIDE KEY BOULEVARD, OLDSMAR, FL, 34677
Active24 days on marketListed Aug 27, 2026MLS #TB8542613
About this home
279 COUNTRYSIDE KEY BOULEVARD
Virtually Staged. Welcome home to this beautiful END UNIT & FULLY UPDATED 2BR/1.5BA townhome in the gated Countryside Key community, offering the rare benefit of an extra-large side yard for addl. outdoor space & privacy. Even better, assoc. fees INCLUDE water, trash, cable & internet! With extensive improvements, an enclosed patio, reserved parking directly in front, & an outstanding Pinellas County location (NON-FLOOD ZONE), this home is truly move-in ready. Step inside to an inviting open first floor designed for comfortable everyday living & entertaining. The kitchen features quartz countertops, custom cabinetry installed in '22, including larger cabinets providing excellent storage. The owners thoughtfully removed the upper cabinetry around the sink & counter area, creating a more open feel and better connection between the kitchen & adjoining living space. Updated appliances, lighting & ceiling fans complement the space, while no popcorn ceilings on either the first or second floor give the home a clean, updated look. Fresh interior paint was completed in August '26. Just beyond the main living area, the enclosed patio creates additional flexible space to relax, entertain, work from home, or just enjoy throughout the year. As an end unit, this home also possesses an extra-large side yard, providing additional outdoor space & separation rarely found with townhome living. Upstairs, the spacious primary suite features large dual closets, built-in bookshelves (providing both character & functional storage), while the generous windows bring an abundance of natural light into the space. Relax in the large private upgraded bathroom to complete the suite! The home has also benefited from an impressive list of improvements. HVAC, water heater & appliances were replaced in '22, along with new attic insulation in '22, washer & dryer in '24, & new light fixtures & ceiling fans. A new impact-rated rear door window was added in '22 for enhanced security, & exterior doorknobs, deadbolts & keys were also replaced. More recently, the home received new exterior paint in '26 & new interior paint in '26. Enjoy the everyday convenience of reserved parking directly in front of the unit's door, along with ample guest parking throughout the gated community & specifically near this unit! Countryside Key also offers a community pool overlooking the pond, tennis courts, & a designated storage area for camper vehicles, boats, trailers, &/or commercial vehicles (subject to association requirements - see HOA). This INCREDIBLE LOCATION is conveniently positioned near the Hillsborough County line & just minutes from the charm, restaurants, waterfront parks & activities of Safety Harbor. You're also only 8.7 miles from beautiful Honeymoon Island State Park and its Gulf beaches, with convenient access to Tampa International Airport, shopping, dining, entertainment and major roadways connecting you throughout the Tampa Bay area (all points). This Countryside Key townhome offers an exceptional combination of privacy, convenience, value & move-in-ready living.
Facts & features
The home at a glance
2
Bedrooms
1.5
Bathrooms
1,105
Sqft
0.02 ac
Lot size
1996
Year built
Two
Levels
$249
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.
$2,701 /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
$2,701/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
+30.5%
$/sqft vs Oldsmar actives
$249 vs $228
Days on market
24 vs 56 typical
Where $249/sqft sits among the 158 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
$400K → $415K
Oldsmar median sold, yr/yr
96.5%
Sale-to-list ratio (12 mo)
80 of 158
Oldsmar actives have cut their price
Median sold price, Oldsmar, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 6% above the OLDSMAR 34677 median. See the full Oldsmar market guide →
Paper trail
This home's history
Reality check
What actually sold near 279 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 · Jul ’26$225,000
382 COUNTRYSIDE KEY BOULEVARD · same community
2 bd · 1.5 ba · 1,105 sqft · $204/sqft · 42 DOM
Sold · Dec ’25$235,000
367 COUNTRYSIDE KEY BOULEVARD · same community
2 bd · 1.5 ba · 1,105 sqft · $213/sqft · 126 DOM
Sold · Jul ’26$234,000
388 COUNTRYSIDE KEY BOULEVARD · same community
2 bd · 1.5 ba · 1,105 sqft · $212/sqft · 63 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
Bridget McLennon
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 279 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 279 COUNTRYSIDE KEY BOULEVARD — before you fall in love.
See it in person
Schedule a tour
Live availability from Bridget's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
279 COUNTRYSIDE KEY BOULEVARD FAQs
What would the monthly payment be for 279 COUNTRYSIDE KEY BOULEVARD?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $2,701/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 279 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 279 COUNTRYSIDE KEY BOULEVARD?+
The most recent tax bill on record (2025) was $4,152. 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 279 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 $275,000, this home is listed about 15% below the Oldsmar median of $324,900. The market section on this page shows how the area is trending.
Which schools are assigned to 279 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.
Keep looking
Similar homes nearby
Listing courtesy of REAL ESTATE FIRM OF FLORIDA, LLC · Charlie Bodine. MLS #TB8542613.
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 279 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 Bridget to ping you on any price or status change →