33 Circle Drive
Stratford, Connecticut 06614
- Beds
- 1
- Baths
- 1
- SqFt
- 588
- Acres
- 0.11
- Year Built
- 1935
- Neighborhood
- North End
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
69
81 under contract
Median List Price
$560,000
69 active listings
Median Closed Price
$480,000
428 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 24, 2026per 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
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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.