147 Boston Street
Guilford, Connecticut 06437
Reduced from $1,595,000
- Beds
- 4
- Baths
- 2 | 2
- SqFt
- 2,966
- Acres
- 0.95
- Year Built
- 1755
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Experience the perfect fusion of timeless distinction and modern elegance in this well-maintained home, where original architectural craftsmanship has been beautifully preserved, and recent updates have brought a fresh, stylish feel to the space. Inside, you'll discover an inviting and versatile residence with numerous unique features that make this property truly one-of-a-kind. Enjoy the warm ambiance created by wide plank wood floors, original woodwork, exposed beams, and multiple fireplaces across the family room, living room, dining area, and primary bedroom. The home features 4+ bedrooms, thoughtfully arranged across two levels for privacy and comfort. Two hall-accessed bathrooms-one with a tub and one with a shower-occupy the second floor, both easily accessible from the hallway. The updated kitchen is an entertainer's dream, featuring leathered granite counters, a Subzero refrigerator, and an LG gas stove. The four-season porch, with its well-placed windows providing a picturesque view of the backyard, offers a perfect space for relaxing, entertaining guests, or creating a media room. It is equipped with a modern-looking Rinnai heater, ensuring comfort year-round regardless of the weather Adjacent to the home is the spacious backyard, which features a fire pit, ample room for gardening or outdoor activities, and existing infrastructure ready for the easy addition of an inground pool.
Key Facts
- City/Town
- Guilford
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1755
- Days on Market
- 207 days
- Beds
- 4
- Baths
- 2 full · 2 half
- Living Area
- 2,966 sq ft
- Lot Size
- 0.95 acres
- Garage / Parking
- 2 garage · 8 total
- Property Taxes
- $16,095 / Annually
Market Snapshot
The Guilford Market
Single Family · trailing 12 months
Active Listings
37
33 under contract
Median List Price
$989,000
37 active listings
Median Closed Price
$652,500
218 sales
Median Days on Market
72
37 active listings
Median $ / Sq Ft
$382
37 active listings
Sale-to-List Ratio
101.0%
218 sales
How this home compares
List Price
$1.35M
vs $989,000 median
36.4% above median
Price / Sq Ft
$455
vs $382 median
19.1% above median
Days on Market
207 days
vs 72 days median
135 days longer than median
Based on 37 active and 218 closed sales (trailing 12 mo) of single family in Guilford. Source: SmartMLS · As of September 21, 2026.
Location
147 Boston Street, Guilford, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 17, 2026per month
- Principal & Interest$7,144
- Property Taxes$1,341
- Insurance$450
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Guilford
- Neighborhood
- N/A
- County
- New Haven
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1755
- New Construction
- No/Resale
- Living Area
- 2,966 sq ft
Schools
- Elementary
- Calvin Leete
- Middle
- Baldwin
- High
- Guilford
Interior
- Heating
- BaseboardHot Water
- Heat Fuel
- Natural GasPropaneSolar
- Cooling
- Ceiling FansWindow Unit
- Fireplaces
- 5
- Laundry
- Main Level
- Appliances
- Oven/RangeSubzeroDishwasherWasherDryer
- Basement
- FullUnfinishedFull With Hatchway
- In-Law Apartment
- PossibleDetached
- Additional Rooms
- Sitting Room
Exterior & Lot
- Lot Size
- 0.95 acres
- Zoning
- R-3
- Garage / Parking
- 2 garage spaces8 total parking spacesDetached GarageDrivewayPrivateCrushed StoneGravel
- Waterfront Details
- Beach RightsAccess
- Water Source
- Public Water Connected
- Sewer
- Septic
- Flood Zone
- No
- Construction
- Clapboard
- Roof
- Slate
- Foundation
- ConcreteMasonry
- Exterior Features
- ShedCabanaLightingPaddock
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $16,095 / Annually
- Days on Market
- 207
- MLS #
- 24155372
- MLS Status
- Active
Similar Properties
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Co-Listed By
Steve Sinapis
William Raveis Real Estate
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/21/2026. 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 9/21/2026 at 8:25 PM UTC.