1389 CHESTERFIELD DRIVE CLEARWATER FL 33756 MLS #TB8504519

1389 CHESTERFIELD DRIVE
CLEARWATER, FL, 33756
$575,000
3 Beds
2 Baths
1,414 SqFt
0.19 Acres
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MLS #TB8504519 image #0
Under contract-accepting backup offers. Whether you’re searching for your forever home, a sun-soaked Florida retreat, or a savvy investment property — 1389 Chesterfield Drive has you covered. This stunning coastal gem checks every box, and then some.
MOVE-IN READY | NEWLY RENOVATED | NO FLOOD ZONE | NO HOA
The hard work is already done: Roof (2023), water heater (2023), 125-amp electrical panel (2022), HVAC (2019), screened lanai (2023), gutters (2023), irrigation pump (2023), and appliances (2023). Pack your bags and start living — this home is ready when you are. A recently completed four-point inspection is available upon request, giving you even greater peace of mind.
Tucked into a wonderful, established neighborhood within the city limits of Largo, this beautifully designed 3-bedroom, 2-bath coastal home sits just 10 minutes from the beach. From the moment you step through the front door, something shifts — the coastal vibe wraps around you, and it immediately feels like home with a bright open layout.
Luxury vinyl plank flooring flows seamlessly throughout, anchoring the open-concept design. The updated kitchen features spectacular quartz countertops, handcrafted tile backsplash, new stainless steel appliances, a designer range hood, and floating shelves that are equal parts functional and gorgeous. Step through to the screened-in lanai and let Florida do its thing. A heated in-ground pool glistens over a paver patio, surrounded by a fully fenced, private backyard complete with a pool shed. A great space for gathering with friend and family, this outdoor space was made for making memories.
The primary suite is your personal sanctuary, featuring an en-suite bath and a generous sitting area large enough for a dedicated home office. Both bathrooms have been refreshed with new vanities. The two-car garage offers built-in shelving to keep life organized. And a lawn with a fully automated irrigation system that runs off a private well, without the added water bill.
The flexibility here is truly rare. Approved for short-term rentals by the City of Largo, this home works beautifully as a primary residence, a second home escape, or an income-generating investment property. Turnkey setup. Furniture negotiable with a strong offer.
All of this, just minutes from the Gulf beaches, top-rated restaurants, shopping, and everything the Coast has to offer.
Homes like this don’t wait. Neither should you.

Property Details

Price:
$575,000
MLS #:
TB8504519
Status:
Pending
Beds:
3
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
CHESTERFIELD HEIGHTS
Neighborhood:
33756clearwaterbelleair
Listed Date:
May 3, 2026
Finished Sq Ft:
1,414
Total Sq Ft:
1,924
Lot Size:
8,294 sqft / 0.19 acres (approx)
Year Built:
1962
PoolPrimary Bedroom Main Floor33756 – Clearwater/belleair33756clearwaterbelleairChesterfield HeightsPonce De Leon Elementary-pnLargo Middle-pnLargo High-pnAs Per County Codes1-7 DaysPets Allowed

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Schools

Elementary School:
Ponce de Leon Elementary-PN
Middle School:
Largo Middle-PN
High School:
Largo High-PN

Interior

Appliances
Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Range Hood, Refrigerator, Washer
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Luxury Vinyl, Tile
Heating
Central, Electric, Heat Pump
Interior Features
Ceiling Fan(s), Eating Space In Kitchen, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Thermostat, Window Treatments
Laundry Features
Electric Dryer Hookup, In Garage, Washer Hookup
Levels
One

Exterior

Architectural Style
Coastal, Ranch
Attached Garage YN
1
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
West
Exterior Features
Garden, Irrigation System, Private Yard, Rain Gutters
Fencing
Wood
Garage Spaces
2
Lot Features
Cleared, Landscaped, Near Golf Course
Patio And Porch Features
Covered, Enclosed, Front Porch, Patio, Rear Porch, Screened
Roof
Shingle
View
City, Pool
Window Features
Blinds

Financial

Tax Year
2025
Taxes
$6,700

Map

Community

Subdivisions in CLEARWATER

Market Summary

Current real estate data for Single Family in CLEARWATER as of May 16, 2026
557
Single Family Listed
92
Avg DOM
324
Avg $ / SqFt
$601,336
Avg List Price

Property Summary

    Located in the CHESTERFIELD HEIGHTS subdivision, 1389 CHESTERFIELD DRIVE CLEARWATER FL is a Single Family for sale in CLEARWATER, FL, 33756. It is listed for $575,000 and features 3 beds, 2 baths, and has approximately 1,414 square feet of living space, and was originally constructed in 1962. The current price per square foot is $407. The average price per square foot for Single Family listings in CLEARWATER is $324. The average listing price for Single Family in CLEARWATER is $601,336. To schedule a showing of MLS#tb8504519 at 1389 CHESTERFIELD DRIVE in CLEARWATER, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.

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1389 CHESTERFIELD DRIVE
CLEARWATER, FL