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33 Circle Drive

Stratford, Connecticut 06614

COMING SOON - NEW$375,000
Beds
1
Baths
1
SqFt
588
Acres
0.11
Year Built
1935
Matt Caiola

Matt Caiola

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Waterfront1 Fireplace

About This Home

Morning coffee overlooking the lake, an afternoon paddle, and evenings by the fireplace...welcome to life at 33 Circle Drive. Set directly on Cook's Pond in Stratford's North End, this charming year-round cottage offers a waterfront escape with everyday conveniences close by. Updated throughout, including a newer roof and mechanicals, this inviting home features one bedroom plus an additional room with potential as a second bedroom or home office. A remodeled kitchen and full bath complement the welcoming living space with its wood-burning fireplace. Central air provides summer comfort, while a full unfinished basement offers additional storage. Step onto the waterside deck for outdoor dining or quiet moments overlooking the pond. Direct waterfront access invites kayaking, fishing, and paddle sports right from home. For adventures on land, nearby Roosevelt Forest offers woodland walks and hiking accessed through the Pumpkin Ground trailhead. Shopping, restaurants, beaches, and Boothe Memorial Park add to the appeal, with convenient access to I-95 and the Merritt Parkway. Midtown Manhattan is approximately 60 miles from Stratford by car, with driving time dependent on traffic. Whether enjoyed as a full-time home or a weekend getaway, this beautifully updated cottage delivers waterfront charm and a refreshing change of pace.

Key Facts

City/Town
Stratford
Neighborhood
North End
Property / Style
Single Family · Cottage
Year Built
1935
Days on Market
0 days
Beds
1
Baths
1 full
Living Area
588 sq ft
Lot Size
0.11 acres
Garage / Parking
2 total
Property Taxes
$4,040 / Annually

Market Snapshot

The Stratford Market

Single Family · trailing 12 months

Median Days on Market

28

69 active listings

Median $ / Sq Ft

$300

69 active listings

Sale-to-List Ratio

101.6%

428 sales

How this home compares

List Price

$375,000

vs $560,000 median

33.0% below median

Price / Sq Ft

$638

vs $300 median

2.1× the median

Days on Market

0 days

vs 28 days median

28 days fresher than median

Based on 69 active and 428 closed sales (trailing 12 mo) of single family in Stratford. Source: SmartMLS · As of September 25, 2026.

Location

33 Circle Drive, Stratford, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,464

per month

  • Principal & Interest$2,002
  • Property Taxes$337
  • Insurance$125
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Stratford
Neighborhood
North End
County
Fairfield

Residence

Property Type
Single Family
Style
Cottage
Year Built
1935
New Construction
No/Resale
Living Area
588 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hot Air
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
1
Laundry
Main Level
Laundry Location
In Full Bath - Separate Closet
Appliances
Oven/RangeMicrowaveRefrigeratorDishwasher
Basement
FullUnfinishedStorageWalk-outConcrete Floor
In-Law Apartment
No

Exterior & Lot

Lot Size
0.11 acres
Zoning
RS-3
Garage / Parking
2 total parking spacesOn Street Parking
Waterfront
Direct waterfront
Waterfront Details
LakeWater CommunityViewAccess
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Flood Zone
Yes
Construction
Vinyl Siding
Color
Grey/ Blue
Roof
Asphalt Shingle
Foundation
Stone
Exterior Features
ShedDeckGutters
Lot Description
Lightly WoodedTreedSloping LotWater View

Listing & Financials

Property Taxes
$4,040 / Annually
Days on Market
0
MLS #
24209753
MLS Status
Coming Soon

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Alan Hamilton

(203) 952-8880

William Raveis Real Estate

(203) 227-4343

Co-Listed By

Melissa Hamilton

William Raveis Real Estate

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 9/25/2026. This information is provided 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 or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 9/25/2026 at 3:15 PM UTC.