27 Circle Drive
Ashford, Connecticut 06278
- Beds
- 2
- Baths
- 1
- SqFt
- 1,070
- Acres
- 0.19
- Year Built
- 1959
- Property Type
- Single Family

Matt Caiola
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About This Home
Welcome to 27 Circle Drive, a charming 2-bedroom, 1-bath home nestled in the desirable Lake Chaffee community! Offering a wonderful blend of comfort, character, and potential, this inviting home features a spacious living room with an open layout, creating a warm and welcoming atmosphere for everyday living and entertaining. The generously sized kitchen offers ample space for cooking and gathering, along with a separate dining area. The main-level bathroom features both a separate shower and whirlpool tub, providing the perfect place to relax and unwind. Upstairs, you'll find two spacious bedrooms, including one with the potential to be reconfigured to accommodate an additional room, ideal for a home office, nursery, or guest space. While the home offers a comfortable and functional layout, it also presents a wonderful opportunity for buyers to bring their own style and personal touches through cosmetic updates and improvements. Step outside to enjoy the deck overlooking the expansive yard, with property extending to the opposite side of Circle Drive, offering plenty of room for outdoor activities, gardening, and entertaining. Enjoy all that the Lake Chaffee community has to offer, including access to two beaches and a boat launch, perfect for swimming, kayaking, and enjoying the outdoors. Conveniently located near I-84, approximately 30 minutes to Hartford and 35 minutes to Worcester, this property offers a wonderful balance of peaceful lake community living.
Key Facts
- City/Town
- Ashford
- Neighborhood
- N/A
- Property / Style
- Single Family · Cottage
- Year Built
- 1959
- Days on Market
- 0 days
- Beds
- 2
- Baths
- 1 full
- Living Area
- 1,070 sq ft
- Lot Size
- 0.19 acres
- Property Taxes
- $3,643 / Annually
Market Snapshot
The Ashford Market
Single Family · trailing 12 months
Active Listings
21
12 under contract
Median List Price
$477,999
21 active listings
Median Closed Price
$430,000
40 sales
Median Days on Market
38
21 active listings
Median $ / Sq Ft
$241
21 active listings
Sale-to-List Ratio
100.0%
40 sales
How this home compares
List Price
$225,000
vs $477,999 median
52.9% below median
Price / Sq Ft
$210
vs $241 median
12.9% below median
Days on Market
0 days
vs 38 days median
38 days fresher than median
Based on 21 active and 40 closed sales (trailing 12 mo) of single family in Ashford. Source: SmartMLS · As of November 14, 2026.
Location
27 Circle Drive, Ashford, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Nov 12, 2026per month
- Principal & Interest$1,211
- Property Taxes$304
- Insurance$75
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Ashford
- Neighborhood
- N/A
- County
- Windham
Residence
- Property Type
- Single Family
- Style
- Cottage
- Year Built
- 1959
- New Construction
- No/Resale
- Living Area
- 1,070 sq ft
Schools
- Elementary
- Ashford
- High
- Smith
Interior
- Heating
- Hot Air
- Heat Fuel
- OilOther
- Cooling
- Ceiling Fans
- Fireplaces
- 1
- Laundry
- Main Level
- Appliances
- Oven/RangeRefrigeratorWasherDryer
- Basement
- Crawl SpaceUnfinished
- Interior Features
- Cable - AvailableOpen Floor Plan
Exterior & Lot
- Lot Size
- 0.19 acres
- Zoning
- RA
- Waterfront Details
- Walk to WaterBeach RightsAccess
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Vinyl Siding
- Color
- yellow
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- Deck
- Lot Description
- Lightly WoodedLevel Lot
Listing & Financials
- Property Taxes
- $3,643 / Annually
- Days on Market
- 0
- MLS #
- 24221377
- MLS Status
- Active
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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 11/14/2026. 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 11/14/2026 at 5:45 AM UTC.