205 CHESTNUT STREET, OLDSMAR, FL, 34677
Active6 days on marketListed Aug 8, 2026MLS #TB8537182
About this home
205 CHESTNUT STREET
Presenting a rare opportunity to acquire a well-positioned property in the heart of Oldsmar. This offering combines excellent visibility with approximately 300ft frontage on SR 580 and is easily accessible with the signalized corner and permitted DOT ingress and egress. The location benefits from continued development along retail corridors and continually growing residential communities in the area. The property features multiple zonings allowing for a variety of potential uses spanning office, retail, restaurant and residential. This property provides the flexibility to meet a range of investment strategies along with the potential for seller financing making it more accessible for a wide range of investors.
Facts & features
The home at a glance
1.14 ac
Lot size
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 — not generic estimates.
$9,017 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
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
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$9,017/mo
Includes estimated PMI — it drops off once you reach 20% equity. 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.
Where it sits
Inside Oldsmar
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Oldsmar. See the full Oldsmar guide →
OLDSMAR 34677 — neighborhood snapshot
Population
22,337
Median age
47.3
Median income
$85,389
Median home value
$352,200
Avg household
2.49
Households w/ children
2,157
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)
Median sold price, Oldsmar, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 500% above the OLDSMAR 34677 median. See the full Oldsmar market guide →
Paper trail
This home's history
Reality check
What actually sold near 205 CHESTNUT STREET
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Jan ’26$335,000
303 SHORE DRIVE W · same community
2 bd · 2 ba · 1,106 sqft · $303/sqft · 189 DOM
Sold · Nov ’25$199,000
313 JEFFERSON AVENUE S · same community
3 bd · 2 ba · 1,271 sqft · $157/sqft · 158 DOM
Sold · Aug ’25$435,000
510 PINE AVENUE S · same community
3 bd · 2 ba · 1,287 sqft · $338/sqft · 86 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
Julian Rivera
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 205 CHESTNUT STREET — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 205 CHESTNUT STREET — before you fall in love.
See it in person
Schedule a tour
Live availability from Julian's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
205 CHESTNUT STREET FAQs
What would the monthly payment be for 205 CHESTNUT STREET?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $9,017/mo — principal and interest, the actual property-tax bill 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.
What are the property taxes on 205 CHESTNUT STREET?+
The most recent tax bill on record (2025) was $2,480. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
How does the price compare to other homes in Oldsmar?+
At $1,499,000, this home is listed about 361% above the Oldsmar median of $325,000. The market section on this page shows how the area is trending.
Which schools are assigned to 205 CHESTNUT STREET?+
Oldsmar 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
01Positioned at the premium end
$1,499,000 runs 500% above the OLDSMAR 34677 median.
02City views
The city view is part of what you're buying — views hold value independently of the structure.
03Fresh on the market
Only 6 days on market in a Oldsmar market that averages 59 — if it fits, move quickly.
04Strong assigned schools
Oldsmar Elementary School, Joseph L. Carwise Middle School, East Lake High School — Oldsmar Elementary School rates 4 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of SUNSHINE REALTY COMPANY LLC · Allison Daigle. MLS #TB8537182.
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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