20 Upson Road
Wolcott, Connecticut 06716
- Beds
- 5
- Baths
- 2 | 2
- SqFt
- 4,681
- Acres
- 36.14
- Year Built
- 1964
- Neighborhood
- Woodtick
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Stunning property consisting of a contemporary 4,680 SF home with 18 rooms on 36+/- acres that are sub-dividable with 16+/- building lots in Wolcott, CT. Country living at its finest at this resort type property with surrounding private woods. Perfect for equestrian, hiking, motorsports and entertaining. From the main house you enter the original 1800's log cabin with exquisite hand polished interior logs which is setup as an entertaining area with a bar, fireplace and pool table. From there you proceed thru the relaxing glassed in porch with flagstone flooring which takes you to the large concrete terrace. There is the expansive view overlooking the 20 x 50 Gunite pool adjacent to the large spring fed natural pond that's stocked with many types of fish where you can launch a boat and go fishing. You have 5 bedrooms, 2 full baths, 2 half baths an oversized 2 car garage, 2nd garage/barn, summer guest house. There is a Unique Roof Top Deck you access from the top floor and also a two and a half story glass tower that brightens the front of the home with sunshine. This home has 2 fireplaces, radiant floor heat in the master bedroom, piano room, kitchen and dining room and two levels of decking. A new roof, skylights, gutters and leaf guards were installed in 2023. New siding and a dog pen with cement flooring and wrought iron fencing was installed in 2020.The owners will be present during viewings. Pre-approval required.
Key Facts
- City/Town
- Wolcott
- Neighborhood
- Woodtick
- Property / Style
- Single Family · Contemporary,Log
- Year Built
- 1964
- Days on Market
- 444 days
- Beds
- 5
- Baths
- 2 full · 2 half
- Living Area
- 4,681 sq ft
- Lot Size
- 36.14 acres
- Garage / Parking
- 6 garage
- Property Taxes
- $13,441 / Annually
Market Snapshot
The Wolcott Market
Single Family · trailing 12 months
Active Listings
34
25 under contract
Median List Price
$549,950
34 active listings
Median Closed Price
$405,000
159 sales
Median Days on Market
39
34 active listings
Median $ / Sq Ft
$235
34 active listings
Sale-to-List Ratio
100.5%
159 sales
How this home compares
List Price
$1.10M
vs $549,950 median
2.0× the median
Price / Sq Ft
$235
vs $235 median
In line with median
Days on Market
444 days
vs 39 days median
405 days longer than median
Based on 34 active and 159 closed sales (trailing 12 mo) of single family in Wolcott. Source: SmartMLS · As of September 17, 2026.
Location
20 Upson Road, Wolcott, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$5,714
- Property Taxes$1,120
- Insurance$367
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Wolcott
- Neighborhood
- Woodtick
- County
- New Haven
Residence
- Property Type
- Single Family
- Style
- Contemporary,Log
- Year Built
- 1964
- New Construction
- No/Resale
- Living Area
- 4,681 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Wolcott
Interior
- Heating
- BaseboardHot AirRadiant
- Heat Fuel
- Oil
- Cooling
- Whole House FanWindow Unit
- Fireplaces
- 2
- Laundry
- Lower Level
- Appliances
- Oven/RangeMicrowaveRange HoodRefrigeratorDishwasherWasherDryer
- Basement
- Full
- In-Law Apartment
- Possible
- Additional Rooms
- Bonus RoomMud RoomSitting Room
Exterior & Lot
- Lot Size
- 36.14 acres
- Zoning
- R-40
- Garage / Parking
- 6 garage spacesAttached GarageDetached Garage
- Waterfront
- Direct waterfront
- Waterfront Details
- PondWalk to Water
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- GunitePool HouseIn Ground Pool
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- ConcreteSlab
- Exterior Features
- Porch-EnclosedBalconyPorchBarnDeckGuest HouseCovered DeckStone Wall
- Lot Description
- TreedProfessionally LandscapedWater ViewOpen Lot
Listing & Financials
- Property Taxes
- $13,441 / Annually
- Days on Market
- 444
- MLS #
- 24108031
- 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 9/17/2026. 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 9/17/2026 at 7:40 PM UTC.