33 Circle Drive
Stratford, Connecticut 06614
- Beds
- 1
- Baths
- 1
- SqFt
- 576
- Acres
- 0.11
- Year Built
- 1935
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Stratford is the PERFECT balance between suburban living and commuter convenience. The best things come in small packages and this WATERFRONT property is proof! 33 Circle Dr is a unique waterfront year round cottage on Cook's Pond in Stratford's North End. This charming home offers 1 bedroom with a secondary sleeping area, direct pond frontage, a deck overlooking the water and private access for kayaking, fishing and paddle sports. Offering a move-in-ready space with CENTRAL AIR and WOOD BURNING FIREPLACE designed to maximize comfort while keeping maintenance to a minimum. Whether you're searching for a peaceful weekend escape, a year-round waterfront retreat, or exploring investment opportunities, this unique property offers exceptional potential. Full unfinished basement for extra storage. Though the neighborhood feels secluded, it is only minutes from I95, Merritt Parkway, Metro-North Railroad, Shopping, Restaurants, Beaches & Golf. Close proximity to Boothe Memorial Park, Short Beach, and Long Beach. ** INVESTOR Airbnb Short Term Rental POTENTIAL **
Key Facts
- City/Town
- Stratford
- Neighborhood
- N/A
- Property / Style
- Single Family · Cottage
- Year Built
- 1935
- Days on Market
- 25 days
- Beds
- 1
- Baths
- 1 full
- Living Area
- 576 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
88 under contract
Median List Price
$575,000
69 active listings
Median Closed Price
$475,000
417 sales
Median Days on Market
33
69 active listings
Median $ / Sq Ft
$303
69 active listings
Sale-to-List Ratio
101.3%
417 sales
How this home compares
List Price
$349,900
vs $575,000 median
39.1% below median
Price / Sq Ft
$607
vs $303 median
2.0× the median
Days on Market
25 days
vs 33 days median
8 days fresher than median
Based on 69 active and 417 closed sales (trailing 12 mo) of single family in Stratford. Source: SmartMLS · As of July 28, 2026.
Location
33 Circle Drive, Stratford, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$1,784
- Property Taxes$337
- Insurance$117
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Stratford
- Neighborhood
- N/A
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Cottage
- Year Built
- 1935
- New Construction
- No/Resale
- Living Area
- 576 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 bathroom
- Appliances
- Oven/RangeMicrowaveRefrigerator
- Basement
- FullUnfinishedFull With Walk-Out
Exterior & Lot
- Lot Size
- 0.11 acres
- Zoning
- RS-3
- Garage / Parking
- 2 total parking spacesOff Street ParkingDrivewayPrivate
- Waterfront
- Direct waterfront
- Waterfront Details
- PondWalk to WaterViewAccess
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- Yes
- Construction
- Vinyl Siding
- Color
- Blue/Gray
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Exterior Features
- ShedDeckStone Wall
- Lot Description
- Water View
Listing & Financials
- Property Taxes
- $4,040 / Annually
- Days on Market
- 25
- MLS #
- 24188441
- MLS Status
- Active
- Financing
- FHA,VA,CHFA
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. 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 7/28/2026 at 7:01 AM UTC.