173 Highwoods Drive
Guilford, Connecticut 06437
- Beds
- 5
- Baths
- 5 | 4
- SqFt
- 5,414
- Acres
- 3.93
- Year Built
- 1660
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
A LEGENDARY GUILFORD ESTATE-where extraordinary history, artistry, architecture, & modern luxury converge. One of New England's most exceptional restorations, the Pitkin House is a remarkable 18th-century treasure set privately on nearly 4 acres of mature trees, stone walls, manicured lawns, enchanting gardens, & extraordinary recreational amenities. Originally constructed in East Hartford, the principal 1764 residence incorporates a circa-1660 ell & was meticulously dismantled & reassembled at this coveted Guilford setting in 1955. Recognized on the National Register of Historic Places, this remarkable property has been lovingly transformed for today's lifestyle while preserving its irreplaceable character & craftsmanship. Inside, more than 5,500sf unfolds across three levels w/ an exceptional collection of architectural details, including original wide-plank floors, massive hand-hewn beams, exquisite paneling, period millwork, & 8 fireplaces. The sophisticated kitchen blends custom cabinetry, granite countertops, center island, double ovens, skylights, breakfast area, built-in hutches, & butler's pantry. Formal dining & living rooms provide elegant settings for entertaining, while the extraordinary family room features 18-inch-wide original hemlock floorboards, monumental beams, French doors to the grounds, & a spectacular copper-hooded fireplace. Perhaps the home's most magical spaces are the garden room & 440sf octagonal solarium. ***CONTINUED***
Key Facts
- City/Town
- Guilford
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial,Antique
- Year Built
- 1660
- Days on Market
- 0 days
- Beds
- 5
- Baths
- 5 full · 4 half
- Living Area
- 5,414 sq ft
- Lot Size
- 3.93 acres
- Garage / Parking
- 8 garage
- Property Taxes
- $29,240 / 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
$1.82M
vs $989,000 median
84.5% above median
Price / Sq Ft
$337
vs $382 median
11.8% below median
Days on Market
0 days
vs 72 days median
72 days fresher 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
173 Highwoods Drive, Guilford, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 17, 2026per month
- Principal & Interest$9,664
- Property Taxes$2,437
- Insurance$608
- 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,Antique
- Year Built
- 1660
- New Construction
- No/Resale
- Living Area
- 5,414 sq ft
Schools
- Elementary
- Guilford Lakes
- Middle
- Baldwin
- High
- Guilford
Interior
- Heating
- BaseboardHot AirHot WaterZoned
- Heat Fuel
- GeothermalOilPropane
- Cooling
- Central AirZoned
- Fireplaces
- 8
- Laundry
- Upper Level
- Laundry Location
- In closet in 2nd floor bathroom.
- Appliances
- Electric CooktopWall OvenMicrowaveRefrigeratorFreezerIcemakerDishwasherDisposalInstant Hot Water TapWasherDryer
- Basement
- PartialStorageInterior AccessLiveable SpacePartial With HatchwayConcrete Floor
- In-Law Apartment
- YesDetachedSeparate Entry
- Interior Features
- Auto Garage Door OpenerCable - AvailableHumidifierSecurity System
- Additional Rooms
- Bonus RoomFoyerMud RoomSitting RoomSolariumStaff QuartersWorkshop
- Accessibility
- Accessible Bath
Exterior & Lot
- Lot Size
- 3.93 acres
- Zoning
- R-5
- Garage / Parking
- 8 garage spacesBarnAttached GarageDetached Garage
- Waterfront
- Direct waterfront
- Waterfront Details
- PondViewAccess
- Water Source
- Public Water Connected
- Sewer
- Septic
- Flood Zone
- No
- Pool
- Pool HouseVinylSalt WaterIn Ground Pool
- Construction
- ClapboardHardie Board
- Color
- Slate Blue
- Roof
- Shake
- Foundation
- Concrete
- Exterior Features
- BarnGuest HousePatioShedTennis CourtPorchGarden AreaStone WallUnderground Sprinkler
- Lot Description
- Fence - PartialFence - StoneFence - Electric PetFence - PrivacyLightly WoodedLevel LotOn Cul-De-SacProfessionally LandscapedWater View
Listing & Financials
- Property Taxes
- $29,240 / Annually
- Days on Market
- 0
- MLS #
- 24208638
- 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 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 7:00 PM UTC.