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20 Upson Road

Wolcott, Connecticut 06716

ACTIVE$1,100,000
Beds
5
Baths
2 | 2
SqFt
4,681
Acres
36.14
Year Built
1964
Matt Caiola

Matt Caiola

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WaterfrontGuest HousePool6-Car Garage2 Fireplaces

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$7,201

per 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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Listed By

Donald Orsini

Don Orsini Realty, LLC

(203) 525-5134

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.