33 Circle Drive, Stratford, CT 06614
Property image
Property image
NEW
COMING SOON 10/2

$375,000

  • 1 Bed
  • 1 Bath
  • 588 sqft

33 Circle Drive, Stratford, CT 06614

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Home Highlights

Single-Family Home
Built in 1935
$638/sqft
Open Parking

Local Information

  • Map ViewExplore the area around 33 Circle Drive.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:Waterfront propertyWood burning fireplaceCentral airDeck overlooking the waterDirect pond frontageMove-in-ready space
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.
Last check for updates: about 7 hours ago
Listing courtesy of Alan T. Hamilton, (203) 952-8880
William Raveis Real Estate, (203) 952-8880
Co-Listing Agent: Melissa Hamilton, (203) 581-4985
William Raveis Real Estate, (203) 227-4343
Source: Smart MLS, MLS#24209753
Also Listed on Smart MLS.

Open House

Saturday, October 03
1:00 PM to 3:00 PM

Home Details for 33 Circle Drive

Interior Features

Interior Details
Basement: Full,Unfinished,Storage Space,Walk-Out Access,ConcreteNumber of Rooms: 4Types of Rooms: Master Bedroom, Bathroom, Kitchen, Living Room, Office
Beds & Baths
Number of Bedrooms: 1Number of Bathrooms: 1Number of Bathrooms (full): 1
Dimensions and Layout
Living Area: 588 Square Feet
Appliances & Utilities
Appliances: Oven/Range, Microwave, Refrigerator, Dishwasher, Water HeaterDishwasherLaundry: Main LevelMicrowaveRefrigerator
Heating & Cooling
Heating: Forced Air,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
View
Has a ViewView: Water

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: DeckOther Structures: Shed(s)Exterior: Rain GuttersFoundation: StoneNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageHas Open ParkingParking Spaces: 2Parking: On Street
Frontage
WaterfrontWaterfront: Waterfront, Lake, Water Community, AccessOn Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 588 Square Feet

Days on Market

Days on Market: <1 day on Trulia

Property Information

Year Built
Year Built: 1935
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cottage
Building
Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Not Included in Sale: See AddendumParcel Number: 366236

Price & Status

Price
List Price: $375,000Price Per Sqft: $638
Status Change & Dates
Possession Timing: Immed

Active Status

MLS Status: Coming Soon

Location

Direction & Address
City: StratfordCommunity: North End
School Information
Elementary School: Per Board of EdHigh School: Per Board of Ed

Agent Information

Listing Agent
Listing ID: 24209753

Building

Building Area
Building Area: 588 Square Feet

Community

Community Features: Golf, Health Club, Lake, Medical Facilities

HOA

No HOA

Lot Information

Lot Area: 4791.6 sqft

Miscellaneous

BasementMls Number: 24209753Attic: Access Via HatchWater ViewWater View: WaterAttribution Contact: (203) 952-8880Above Grade Unfinished Area: 588Activation Date: Fri Oct 02 2026

Additional Information

GolfHealth ClubLakeMedical Facilities

Around this home

What Locals Say about Stratford

At least 557 Trulia users voted on each feature.

  • 85 % Say parking is easy

  • 83 % Say it's dog friendly

  • 82 % Say yards are well-kept

  • 81 % Say car is needed

  • 76 % Say there's holiday spirit

  • 72 % Say there are sidewalks

  • 65 % Say people would walk alone at night

  • 63 % Say kids play outside

  • 62 % Say streets are well-lit

  • 61 % Say it's quiet

  • 58 % Say they plan to stay for at least 5 years

  • 56 % Say neighbors are friendly

  • 54 % Say it's walkable to restaurants

  • 54 % Say there's wildlife

  • 44 % Say it's walkable to grocery stores

  • 33 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Ellie
    "You need a car to get around. Everyone minds their own business for the most part. "
    0
    Flag
  • Maria Cintron
    "it is very quiet nice neighborhood, friendly neighbors. Nice looks quite clean. it is very quiet nice neighborhood, friendly neighbors."
    0
    Flag
  • Trulia User
    "Easy access to major highways and routes and public transportation and commuter trains and airports!"
    0
    Flag
  • Bigdaye
    "High school isn’t too great. There are lots of stores to get your needs. People’s around here are generally friendly. "
    0
    Flag
  • Ellie
    "There are many community events like fairs and music events. The neighborhood is clean and most neighbors are respectful of one another for the most part. "
    0
    Flag
  • Hmmm Bon
    "100% need a vehicule to get around Town. Rt 8 is nearby, so not far from all ammineties. That is it"
    0
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  • Jerryyambo2
    "Great commute you have 95 and metro north take all away to grand central. You also have Merritt parkways "
    0
    Flag
  • Keshamariamcclain
    "It is quiet and pet friendly. The neighborhood comes alive on holidays. Everyone looks out for their neighbors "
    0
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  • Boyd238
    "There is city bus from Bridgeport that comes thru my area. The train station is about 2 miles from my house in Stratford."
    0
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  • Keshamariamcclain
    "Everyone seems to have a dog. Very pet friendly neighborhood. For the most part everyone picks up after their dog. "
    0
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  • Boyd238
    "There are neighbors who walk there dogs in my neighborhood. Also there is a large dog park near my home. "
    0
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  • Giof777
    "It is a community with a lot of security and tranquility and very peaceful A very happy city and I like that I feel very happy for my children because it’s a very good place for them to grow up"
    4
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  • Trulia User
    "I don’t know I always visited over there and it’s not a lot of grass or land it’s just sidewalks and the road "
    1
    Flag
  • Nancyamilan
    "Plenty of grassy areas near sidewalks for bathroom breaks must keep leashed due to traffic on main roads great dog park in town"
    0
    Flag
  • Solebo.kristeena
    "I enjoy living jn Stratford. It is a central location with everything you need within a 5 minute drive."
    1
    Flag
  • Shannon M.
    "There’s a lot of parks & beaches to visit. Tons of pedestrian friendly main roads & neighborhoods. Some parts might not have sidewalks but roads are usually not too narrow. "
    15
    Flag
  • Anna
    "I’ve lived here for 3 years plus and it’s a great neighborhood to start/have a family and walking distance for necessities"
    3
    Flag
  • Laura G.
    "Family friendly close to elementary school and high school park nearby shopping close short distance to major highways"
    5
    Flag
  • Yevgeni G.
    "Good schools in this little town. Kids are nice as well. Most owners of dogs pick up after their pets."
    0
    Flag
  • Anna
    "Music on the green during the summer and movie night at short beach Farmers market on Monday’s And tons of church fairs and animal adoption fairs Lots of outdoor eating with music a perfect way to enjoy summer to its fullest "
    4
    Flag
  • Keshamariamcclain
    "not big on public transportation in this area. Metro north train is the main transportation. People drive everywhere. "
    1
    Flag
  • Keshamariamcclain
    "All dogs are welcomed and everyone picks up after their dog. Dog owners are friendly. Almost every household seems to have a dog."
    3
    Flag
  • Tgbadamassi
    "Great place to live ... I move here recently fron NYC and think I made a great decision. I am enjoying my house and I feel very safe "
    9
    Flag
  • Diane P.
    "Safe family neighborhood surrounded by 3 beautiful beaches, fun get together,and everyone looks out for each other,their children and elderly. Very caring community"
    1
    Flag
  • Staceyannhenry223
    "I love living here! This s a friendly neighborhood with quite streets and a pond in my backyard. Great times!"
    3
    Flag
  • Janick C.
    "I’ve lived in Stratford for over four years now I am glad to say that I am moving this month you must be very careful where in Stratford do you live one side is very close to a bad part of the city of Bridgeport we are gunshots on a regular basis our cars have been robbedOver four times in the last two years the police officers or department are sticklers and no help and I am very glad that I am moving this month living in Stratford you may as well be living in the middle of Bridgeport"
    0
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  • Michael H.
    "I've live in Stratford for nearly a decade and its exactly what I like in a town.. not to much traffic, good rated schools for my children, convenient shopping, clean streets, nice people.. There's plenty more but I wont drone on."
    0
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  • Staceyannhenry223
    "I love my neighborhood people are great and I feel safe. I know my neighbors and we all get along well. The schools are great and the neighborhood is clean. We plan on purchasing a house somewhere in this neighborhood very soon. "
    4
    Flag
  • Passmb9
    "It’s an all around well diverse area, many local shops to eat as well as large chain retailers not to far out of the way"
    1
    Flag
  • Alexa H.
    "Stratford day is held in June then there’s the 4th of July at short beach and they have the fireworks there "
    1
    Flag
  • Deborah H.
    "There are many folks in the neighborhood walking their dogs. The neighbors are friendly and look out for one another. "
    1
    Flag
  • Mayra A.
    "No events that I know of. Should be more for kids and elderly. There is one event for pets. That’s all I can recall "
    0
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  • Samantha S.
    "Good neighborhood. quiet. pretty. safe. I lived here my whole life. Neighbors are also dependable. schools are closeby"
    0
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  • Hope W.
    "Me & my husband just moved to Stratford one year ago & so far we love the area. With his job relocating him to Stamford we decided to move to Stratford which was a great move."
    0
    Flag
  • Danishmoe77
    "There are weekly farmers markets and free community concerts at the town green. Neighbors are also friendly and help each other."
    1
    Flag
  • Aracelis V.
    "It’s a nice and peaceful place to live... schools shopping trains stations everything you need for living "
    0
    Flag
  • Erin K.
    "Overall nice place to raise a family. Schools need improvement but it's worth the investment. Great local amenities like new local businesses and restaurants show the area is only getting better. "
    0
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  • Cynthia D.
    "It’s location is great because it borders other towns and is close to highway and other transportation "
    0
    Flag
  • Alexa
    "Carnivals on Main Street are nice as well as special beach access for residents to the beach for 4th of July"
    0
    Flag
  • Kimberly L.
    "Events on the green. Due to it being near 4th of July, a nearby beach also hosts a band/ fireworks show. "
    0
    Flag

Market trends in Stratford

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$475K
$20.83KMoM
Sale-to-List Price
102.5%
0.6%MoM
Price per sq ft
$303
$11MoM
Available listings
160
2MoM

Home Value

Trulia Estimate
$346K
Since last month
$100 (0%)
Since last year
Decreased$6K (-1.7%)
Since last sale
Increased$106K (+44.2%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +97% in the last 10 years
MonthEstimated value
2026
September 2026$346K
August 2026$346K
July 2026$349K
June 2026$371K
May 2026$379K
April 2026$376K
March 2026$369K
February 2026$364K
January 2026$354K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1462 Cutspring Road, Stratford, CT
0.16
Single-Family Home
$475,000
10/31/25
3
2
1,447
160 Cheshire Street, Stratford, CT
0.20
Single-Family Home
$450,000
12/12/25
3
2
2,025
170 Pumpkin Ground Road, Stratford, CT
0.14
Single-Family Home
$569,900
03/30/26
3
1.5
2,340
15 Tavern Rock Road, Stratford, CT
0.16
Single-Family Home
$574,186
05/04/26
4
3
2,454
290 Pumpkin Ground Road, Stratford, CT
0.22
Single-Family Home
$585,000
01/16/26
3
2.5
2,036
85 Euclid Avenue, Stratford, CT
0.50
Single-Family Home
$500,000
09/02/26
2
1.5
2,004
105 Meadow Wood Road, Stratford, CT
0.17
Single-Family Home
$680,000
08/11/26
5
3
2,530
175 Twin Oaks Terrace, Stratford, CT
0.29
Single-Family Home
$579,000
11/24/25
4
2
2,018
45 Bulmer Drive, Stratford, CT
0.55
Single-Family Home
$505,000
08/07/26
3
1.5
1,335
35 Eureka Avenue, Stratford, CT
0.39
Single-Family Home
$562,000
07/30/26
3
1.5
1,564

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
LOT 4 Pumpkin Ground Road, Stratford, CT 06497
0.04
$652,400
4
2.5
2,572
Off Market
40 Pumpkin Ground Road, Stratford, CT 06614
0.05
$684,100
3
2.5
1,822
Off Market
65 Pumpkin Ground Road, Stratford, CT 06614
0.09
$474,900
3
1
2,041
Off Market
1725 Cutspring Road, Stratford, CT 06614
0.11
$619,200
3
2.5
2,250
Off Market
1725 Cutspring Road, Stratford, CT 06497
0.11
$625,400
3
2.5
2,200
Off Market
52 Circle Drive, Stratford, CT 06614
0.09
$859,900
4
2.5
2,000
For Sale
40 Tavern Rock Road, Stratford, CT 06614
0.14
$529,100
3
1.5
2,475
Off Market
75 Pumpkin Ground Road, Stratford, CT 06614
0.14
$621,800
3
3.5
2,103
Off Market
50 Oak Ridge Road, Stratford, CT 06614
0.14
$799,900
3
3
2,103
For Sale
170 Pumpkin Ground Road, Stratford, CT 06614
0.14
$569,900
3
1.5
2,340
Recently Sold
15 Tavern Rock Road, Stratford, CT 06614
0.16
$655,900
4
3
2,454
Foreclosure

Price and Tax history

DateEventPrice
Aug 27, 2026
Source: Smart MLS #24188441
ListingRemoved
$349,900
Jul 10, 2026
Source: Smart MLS #24188441
Listed For Sale
$349,900
Apr 29, 2022
Source: Smart MLS #170462109
Sold
$239,900
Mar 8, 2022
Source: Smart MLS #170462109
Contingent
$239,900
Feb 17, 2022
Source: RE/MAX International #170462109
Pending
$239,900

LGBTQ Local Legal Protections

Alan T. Hamilton, William Raveis Real Estate, (203) 952-8880
Agent Phone: (203) 952-8880
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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Frequently asked questions about 33 Circle Drive

  • What is the estimated monthly payment for 33 Circle Drive?
    Based on a $375,000 list price with 20% down at today's rates, the estimated monthly payment for 33 Circle Drive in Stratford, CT is approximately $2,709 (about $2,106 principal & interest, $528 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 33 Circle Drive compare to homes in Stratford?
    33 Circle Drive in Stratford, CT is listed at $375,000, about 21% below the $475K median sale price in Stratford.
  • What do residents say about Stratford?
    Residents describe Stratford, CT as easy to park in, dog-friendly, and well-kept. Most residents say you need a car. See homes for sale in Stratford, CT.
  • What are the closest schools to 33 Circle Drive?
    The closest schools to 33 Circle Drive in Stratford, CT are Bunnell High School (rated 8/10), Chapel School (Elementary, rated 4/10), Harry B. Flood Middle School (rated 4/10).
  • Does 33 Circle Drive have air conditioning?
    Yes, 33 Circle Drive in Stratford, CT has air conditioning.
  • Does 33 Circle Drive have laundry facilities?
    Yes, 33 Circle Drive in Stratford, CT has laundry facilities.
33 Circle Drive, Stratford, CT 06614 is a 1 bedroom, 1 bathroom, 588 sqft single-family home built in 1935. This property is currently available for sale and was listed by Smart MLS on Sep 25, 2026. The MLS # for this home is MLS# 24209753.