Existing Home on property - 1444 CHESAPEAKE DR, ODESSA
AI Rendering - 1444 CHESAPEAKE DR, ODESSA
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AI Rendering - 1444 CHESAPEAKE DR, ODESSA
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Fully updated Kitchen - 1444 CHESAPEAKE DR, ODESSA
AI Rendering - 1444 CHESAPEAKE DR, ODESSA
Fully updated interior - 1444 CHESAPEAKE DR, ODESSA
AI Rendering - 1444 CHESAPEAKE DR, ODESSA
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AI Rendering - 1444 CHESAPEAKE DR, ODESSA
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AI Rendering - 1444 CHESAPEAKE DR, ODESSA
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Master bedroom - 1444 CHESAPEAKE DR, ODESSA
Master Bath - fully renovated - 1444 CHESAPEAKE DR, ODESSA
Bedroom 2 - 1444 CHESAPEAKE DR, ODESSA
Bedroom 3 - 1444 CHESAPEAKE DR, ODESSA
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39 photos

$875,000

1444 CHESAPEAKE DR
ODESSA, FL 33556
Listed by Stephanie Hessling · COMPASS FLORIDA LLC
Bedrooms
3
Bathrooms
2
Living area
1,578 sqft
Year built
1973

About this home

OVERSIZED LOT - PRIVACY - BUILD YOUR DREAM HOME ___ A rare opportunity to own 4.14 beautiful acres in the heart of Odessa, offering an exceptional combination of privacy, natural beauty, and location. Tucked away among towering mature trees and lush, established landscaping, this property provides a peaceful, secluded setting with picturesque views of Lake Seminole. Opportunities to own acreage of this size in such a desirable Odessa location, especially at this price point, are becoming increasingly difficult to find. ___ Imagine creating your own private retreat, surrounded by nature, with room to bring your vision to life. Whether you're dreaming of a custom luxury estate with a resort-style pool, expansive outdoor entertaining spaces, or simply a place to enjoy the tranquility of having land and privacy, this property offers an incredible canvas for your future. ___ The existing residence provides the opportunity to enjoy the property today, featuring an updated kitchen and bathrooms, along with existing well, septic, and electrical service. Enjoy the home as it is, make it your own, or explore the possibilities of building a custom residence tailored to your lifestyle, subject to applicable approvals. ___ LOCATION, LOCATION, LOCATION! What truly sets this property apart is the ability to enjoy the feeling of being tucked away on your own private acreage without sacrificing convenience. Located approximately 10 minutes from the Suncoast Parkway, you're just a short drive from Tampa International Airport, International Plaza, Downtown Tampa, and some of Tampa Bay's best shopping, dining, entertainment, and everyday essentials. It's the best of both worlds: the space, privacy, and natural beauty of country-style living with the convenience of everything Tampa Bay has to offer. ___ Over four acres. Beautiful lake views. Mature trees. Endless possibilities. Whether you're looking for a peaceful place to call home today or envisioning your future custom estate, 1444 Chesapeake Drive presents a truly special opportunity to own a substantial piece of Odessa. *Buyer to verify all building possibilities, land use requirements, setbacks, and applicable approvals with the appropriate governing authorities.*

Highlights

Waterfront

Property details

MLS
Stellar MLS
MLS #
MFRTB8522437
Property type
Single Family Residence
Subdivision
LAKE ANNE ESTATES SUB
Status
Active
Days on market
117
On market date
June 25, 2026
Stories
N/A
Total bathrooms
2
Garage spaces
2
Parking spaces
N/A
Lot size
4.14 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
ODESSA ELEMENTARY SCHOOL
1.59 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
3.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
887
Student:teacher ratio
17.1:1
District
PASCO
Middle
MARTINEZ MIDDLE SCHOOL
2.99 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
2.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,145
Student:teacher ratio
20.1:1
District
HILLSBOROUGH
High
STEINBRENNER HIGH SCHOOL
2.99 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
1.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
2,506
Student:teacher ratio
24.1:1
District
HILLSBOROUGH

Walkability

Blended score for ODESSA's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

44
Somewhat walkable
out of 100
EPA National Walkability Index
6.3 / 20 -- Below average walkable
Google Places amenity density
63 / 100
Restaurants & cafes9
Grocery stores2
Parks0
Schools2
Transit stops5
Pharmacies3

Market position

How this listing compares to current activity in ODESSA, from live MLS data.

On the market 117 days -- 23 more days than ODESSA's current average of 94 days.
For reference, the median list price across 314 active listings in ODESSA right now is $669,000.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Adjust tax / insurance estimates
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Est. monthly payment
$5,419/mo
$175,000 down
$700,000 loan
Principal & interest$4,540
Property tax (est.)$729
Home insurance (est.)$150

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Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated 2 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.