44 Roslyn Drive
Cheshire, Connecticut 06410
Original List Price $450,000
- Beds
- 3
- Baths
- 2
- SqFt
- 1,412
- Acres
- 0.46
- Year Built
- 1955
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
First time offered in 70 years! Impeccable pride of ownership shines throughout this spacious, well-maintained three-bedroom ranch. The main level living features a large, sun-filled living room that flows seamlessly into a gracious dining room. The eat-in kitchen boasts sliders leading to a newly installed composite deck-perfect for entertaining while overlooking the private backyard. The primary bedroom includes an en-suite full bath with a walk-in shower, complemented by two additional generously sized bedrooms and a central hall bath. Classic hardwood floors are preserved under the carpeting in the two rear bedrooms and hallway (and potentially the primary bedroom!).Downstairs, expand your living space in the finished recreation room complete with a dry bar, a fabulous workshop, and convenient access to the laundry area and one-car garage. Location is everything! You are just minutes away from local shopping and the scenic Farmington Canal Trail system. This home is being sold AS-IS, offering an incredible opportunity to bring your own personal touches to a rock-solid property. Newer Hot Water Heater and Roof was replaced in 2019!
Key Facts
- City/Town
- Cheshire
- Neighborhood
- N/A
- Property / Style
- Single Family · Ranch
- Year Built
- 1955
- Days on Market
- 2 days
- Beds
- 3
- Baths
- 2 full
- Living Area
- 1,412 sq ft
- Lot Size
- 0.46 acres
- Garage / Parking
- 1 garage · 3 total
- Property Taxes
- $6,289 / Annually
Market Snapshot
The Cheshire Market
Single Family · trailing 12 months
Active Listings
24
54 under contract
Median List Price
$642,000
24 active listings
Median Closed Price
$553,750
238 sales
Median Days on Market
33
24 active listings
Median $ / Sq Ft
$270
24 active listings
Sale-to-List Ratio
101.6%
238 sales
How this home compares
List Price
$450,000
vs $642,000 median
29.9% below median
Price / Sq Ft
$319
vs $270 median
18.1% above median
Days on Market
2 days
vs 33 days median
31 days fresher than median
Based on 24 active and 238 closed sales (trailing 12 mo) of single family in Cheshire. Source: SmartMLS · As of July 28, 2026.
Location
44 Roslyn Drive, Cheshire, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$2,294
- Property Taxes$524
- Insurance$150
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Cheshire
- Neighborhood
- N/A
- County
- New Haven
Residence
- Property Type
- Single Family
- Style
- Ranch
- Year Built
- 1955
- New Construction
- No/Resale
- Living Area
- 1,412 sq ft
Schools
- Elementary
- Norton
- Middle
- Per Board of Ed
- High
- Cheshire
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Central Air
- Laundry
- Lower Level
- Laundry Location
- Laundry is located in the work shop
- Appliances
- Electric RangeRefrigeratorDishwasherWasherDryer
- Basement
- FullHeatedSump PumpGarage AccessInterior AccessPartially Finished
Exterior & Lot
- Lot Size
- 0.46 acres
- Zoning
- R-20
- Garage / Parking
- 1 garage space3 total parking spacesAttached GarageUnder House GaragePavedDrivewayPrivatePaved
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- Block
- Exterior Features
- Deck
- Lot Description
- In SubdivisionSloping LotProfessionally Landscaped
Listing & Financials
- Property Taxes
- $6,289 / Annually
- Days on Market
- 2
- MLS #
- 24186652
- MLS Status
- Closed
- Closed Price
- $450,000
- Closed Date
- Jul 27, 2026
Similar Properties
Homes with a close match in area, property type, and price.
Co-Listed By
Amy Kirst
William Pitt Sotheby's Int'l
Buyer's Agent
Jessica Danard
Coldwell Banker Realty
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 5:20 AM UTC.