1444 CHESAPEAKE DRIVE, ODESSA, FL, 33556
Active30 days on marketListed Jun 25, 2026MLS #TB8522437
About this home
1444 CHESAPEAKE DRIVE
4.14 ACRES • LAKE VIEWS • BUILDER/DEVELOPER OPPORTUNITY • PRIVATE ESTATE WITH EXISTING HOME ___ Rare opportunity to own 4.14 acres in the heart of Odessa with beautiful views of Lake Seminole. Whether you’re a builder, developer, investor, or buyer searching for a private estate, this property offers exceptional flexibility in one of Odessa’s most desirable acreage corridors. ___ For builders and developers, the property offers the potential to create a boutique luxury enclave with conceptual lot layouts already envisioned. With future land use designated as RES-3, it presents exciting possibilities for future development (buyer to verify with Pasco County). ___ For buyers looking to enjoy the property today, the existing home offers immediate value with an updated kitchen and bathrooms, along with well, septic, and electric already in place. Renovate, expand, or simply enjoy the home while planning your long-term vision. The expansive acreage provides plenty of room for a custom estate, resort-style pool, guest house, detached garage, workshop, or space for recreational vehicles and boats. ___ Located less than 10 minutes from the Suncoast Parkway, you’ll enjoy convenient access to Tampa International Airport, Downtown Tampa, shopping, dining, and entertainment while experiencing the privacy and beauty that make Odessa one of Tampa Bay’s premier luxury communities. ___ Builder/Developer package available upon request, including conceptual lot layouts, renderings, surveys, market analysis, and development insights.
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
1,578
Sqft
4.14 ac
Lot size
2
Garage
1973
Year built
One
Levels
$602
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 — not generic estimates.
$6,590 /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
$6,590/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.
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
+141.4%
$/sqft vs Odessa actives
$602 vs $271
Days on market
30 vs 38 typical
Where $602/sqft sits among the 202 Odessa 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 Keystone Park Colony
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Odessa. See the full Odessa guide →
Keystone Park Colony — neighborhood snapshot
Population
2,621
Median age
36
Median income
$132,769
Median home value
$535,520
Avg household
3
Households w/ children
334
For the school run
Pasco County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Odessa market
$655K → $682K
Odessa median sold, yr/yr
97.1%
Sale-to-list ratio (12 mo)
113 of 202
Odessa actives have cut their price
Median sold price, Odessa, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 40% above the ODESSA 33556 median. See the full Odessa market guide →
Paper trail
This home's history
Reality check
What actually sold near 1444 CHESAPEAKE DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Jun ’26$563,500
1444 CHESAPEAKE DRIVE · same community
3 bd · 2 ba · 1,578 sqft · $357/sqft · 0 DOM
Sold · May ’26$374,700
1346 BROOKE VIEW DRIVE
3 bd · 2 ba · 1,565 sqft · $239/sqft · 32 DOM
Sold · Sep ’25$725,000
7213 JONES ROAD
3 bd · 2 ba · 1,418 sqft · $511/sqft · 123 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
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 1444 CHESAPEAKE DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 1444 CHESAPEAKE DRIVE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
1444 CHESAPEAKE DRIVE FAQs
What would the monthly payment be for 1444 CHESAPEAKE DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $6,590/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 1444 CHESAPEAKE DRIVE?+
The most recent tax bill on record (2025) was $11,371. 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 Odessa?+
At $950,000, this home is listed about 27% above the Odessa median of $749,950. The market section on this page shows how the area is trending.
Which schools are assigned to 1444 CHESAPEAKE DRIVE?+
Odessa Elementary School (elementary), James W. Mitchell High School (high), Seven Springs Middle School (middle) — Pasco County School District. Always verify school assignments with the district before relying on them.
The brief
Three things that matter here
01Positioned at the premium end
$950,000 runs 40% above the ODESSA 33556 median.
02Waterfront living
This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.
03Strong assigned schools
Odessa Elementary School, James W. Mitchell High School, Seven Springs Middle School — Odessa Elementary School rates 4 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of COMPASS FLORIDA LLC · Stephanie Hessling. MLS #TB8522437.
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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