173 Highwoods Drive
Guilford, Connecticut 06437
Reduced from $1,995,000
- Beds
- 5
- Baths
- 5 | 4
- SqFt
- 5,414
- Acres
- 3.93
- Year Built
- 1660
- Neighborhood
- North Guilford
- 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
A MAGNIFICENT REVIVAL & TIMELESS BLEND OF SOMETHING OLD & SOMETHING NEW. One of the finest restorations in New England, the Pitkin mansion is a true historical treasure. Carefully dismantled & moved to its current site in 1955, the property is nestled within nearly 4 acres of mature trees, manicured lawns, & magical gardens. This classic revival will be celebrated by the most discerning antique home enthusiasts & home lovers alike. Modern flair has been discreetly integrated to enhance function & enjoyment. Contemporary comforts include a poured concrete foundation, geothermal system, full house generator, humidifier, CENTRAL A/C, propane gas, Pella windows, security system, CITY WATER, underground utilities, NEW SEPTIC SYSTEMS, & much more. Significant additions include attached 2-car garage, detached 2-car garage w/half bath & upper bonus room, pool & pool house w/half bath & kitchenette, tennis court, garage barn w/FULL APARTMENT, all exemplifying a harmonious fusion of old & new & completely transformed for today's living. Interiors graciously unfold over more than 5,500sf of formal, casual, & whimsical living spaces. 8 tile-lined fireplaces. Central kitchen well appointed w/large island, granite countertops, double sink, double wall ovens, extensive custom wood cabinetry, butler's pantry, & quality appliances. Sunshine flows through skylights over an eat-in dining area. A 4-story dumbwaiter makes for easy transport of items. Can be modified to be a 1-person elevator.
Key Facts
- City/Town
- Guilford
- Neighborhood
- North Guilford
- Property / Style
- Single Family · Colonial,Antique
- Year Built
- 1660
- Days on Market
- 179 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
$1.90M
vs $989,000 median
91.6% above median
Price / Sq Ft
$350
vs $382 median
8.4% below median
Days on Market
179 days
vs 72 days median
107 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
173 Highwoods Drive, Guilford, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 17, 2026per month
- Principal & Interest$10,035
- Property Taxes$2,437
- Insurance$632
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Guilford
- Neighborhood
- North Guilford
- 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 - PrivacySecludedLightly WoodedLevel LotOn Cul-De-SacProfessionally Landscaped
Listing & Financials
- Property Taxes
- $29,240 / Annually
- Days on Market
- 179
- MLS #
- 24159985
- 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 7:45 PM UTC.