587 High St Extension
Thomaston, Connecticut 06787
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 1,728
- Acres
- 0.48
- Year Built
- 2001
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Timeless Colonial style meets exceptional value under $500,000! Welcome to 587 High Street Extension in Thomaston's desirable Highwood Farms development. This original owner custom-built, well maintained and move in ready home offers 1,728 square feet of thoughtfully arranged living space. An inviting carpeted living room and formal dining room with hardwood flooring create a gracious setting for everyday living and entertaining. The eat-in kitchen features warm wood cabinetry, stainless steel appliances, double door oven, tile flooring and breakfast bar. Sliders lead to a new, expanded 12x24 deck overlooking the backyard-an ideal setting for alfresco dining, morning coffee or relaxing evenings. A half bath with pedestal sink & tile flooring completes the main level. Upstairs are three carpeted bedrooms including a spacious primary suite with walk-in closet and private full bath, a second full bathroom and landing overlooking the 2-story foyer complete this level. The full walkout basement offers laundry, generous storage and opportunities for future customization. An attached two car garage with an oversized interior provides added space for storage alongside your vehicles. Audio & Video on premises. Natural gas heat, central air, public water and sewer enhance the comfort and convenience of this welcoming home. Classic appeal, inviting outdoor living and room to make it your own. Schedule your private showing today!
Key Facts
- City/Town
- Thomaston
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 2001
- Days on Market
- 0 days
- Beds
- 3
- Baths
- 2 full · 1 half
- Living Area
- 1,728 sq ft
- Lot Size
- 0.48 acres
- Garage / Parking
- 2 garage · 6 total
- Property Taxes
- $7,844 / Annually
Market Snapshot
The Thomaston Market
Single Family · trailing 12 months
Active Listings
13
12 under contract
Median List Price
$399,900
13 active listings
Median Closed Price
$340,000
63 sales
Median Days on Market
17
13 active listings
Median $ / Sq Ft
$226
13 active listings
Sale-to-List Ratio
100.0%
63 sales
How this home compares
List Price
$475,000
vs $399,900 median
18.8% above median
Price / Sq Ft
$275
vs $226 median
21.7% above median
Days on Market
0 days
vs 17 days median
17 days fresher than median
Based on 13 active and 63 closed sales (trailing 12 mo) of single family in Thomaston. Source: SmartMLS · As of October 29, 2026.
Location
587 High St Extension, Thomaston, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 29, 2026per month
- Principal & Interest$2,590
- Property Taxes$654
- Insurance$158
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Thomaston
- Neighborhood
- N/A
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 2001
- New Construction
- No/Resale
- Living Area
- 1,728 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Natural Gas
- Cooling
- Central Air
- Laundry
- Lower Level
- Appliances
- Oven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- FullInterior AccessConcrete FloorFull With Walk-Out
- Interior Features
- Auto Garage Door OpenerSecurity System
Exterior & Lot
- Lot Size
- 0.48 acres
- Zoning
- RA80A
- Garage / Parking
- 2 garage spaces6 total parking spacesAttached GarageDrivewayPrivatePaved
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Color
- Sage
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- DeckGuttersLightingStone Wall
- Lot Description
- Lightly WoodedTreedLevel LotSloping Lot
Listing & Financials
- Property Taxes
- $7,844 / Annually
- Days on Market
- 0
- MLS #
- 24217821
- MLS Status
- Active
Similar Properties
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Co-Listed By
Lynn Weitzner
Showcase Realty, Inc.
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 10/29/2026. 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 10/29/2026 at 5:40 PM UTC.