20 Upson Road, Wolcott, CT 06716
Property image
Property image
FOR SALE
36.14 ACRES

$1,100,000

  • 5 Beds
  • 3 Baths
  • 4,681 sqft (on 36.14 acres)

20 Upson Road, Wolcott, CT 06716

Est. Mortgage $7,912/mo*
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Home Highlights

Single-Family Home
Built in 1964
36.14 acre lot
$235/sqft
6 Car Garage

Local Information

  • Map ViewExplore the area around 20 Upson Road.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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.
Last check for updates: about 15 hours ago
Listing courtesy of Donald L. Orsini, (203) 525-5134
Don Orsini Realty, LLC, (203) 525-5134
Source: Smart MLS, MLS#24108031
Also Listed on Smart MLS.

Home Details for 20 Upson Road

Interior Features

Interior Details
Basement: FullNumber of Rooms: 18Types of Rooms: Master Bedroom, Bedroom, Bathroom, Dining Room, Kitchen, Library, Living Room, Sun Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 4Number of Bathrooms (full): 2Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 4681 Square Feet
Appliances & Utilities
Appliances: Oven/Range, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Lower Level,Mud RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,Forced Air,Radiant,OilHas CoolingAir Conditioning: Whole House Fan,Window Unit(s)Has HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 2Has a Fireplace
View
Has a ViewView: Water

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Enclosed, Porch, Deck, CoveredOther Structures: Barn(s), Guest House, Pool HouseExterior: Balcony, Stone WallFoundation: Concrete Perimeter, SlabHas a Private Pool
Parking & Garage
Number of Garage Spaces: 6Number of Covered Spaces: 6No CarportHas a GarageHas an Attached GarageParking Spaces: 6Parking: Attached,Detached
Pool
Pool: Gunite, In GroundPool
Frontage
WaterfrontWaterfront: Waterfront, Pond, Walk to WaterOn Waterfront
Water & Sewer
Sewer: Septic Tank
Farm & Range
Allowed to Raise Horses
Finished Area
Finished Area (above surface): 4681 Square Feet

Days on Market

Days on Market: 180+

Property Information

Year Built
Year Built: 1964
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Contemporary,Log
Building
Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 1443258

Price & Status

Price
List Price: $1,100,000Price Per Sqft: $235
Status Change & Dates
Possession Timing: Negotiable

Active Status

MLS Status: Active

Location

Direction & Address
City: WolcottCommunity: Woodtick
School Information
Elementary School: Per Board of EdHigh School: Wolcott

Agent Information

Listing Agent
Listing ID: 24108031

Building

Building Area
Building Area: 4681 Square Feet

HOA

No HOA

Lot Information

Lot Area: 36.14 Acres

Miscellaneous

BasementMls Number: 24108031Attic: Crawl Space, Walk-upWater ViewWater View: WaterAttribution Contact: (203) 525-5134Above Grade Unfinished Area: 4681

Around this home

What Locals Say about Wolcott

At least 63 Trulia users voted on each feature.

  • 92 % Say car is needed

  • 91 % Say yards are well-kept

  • 88 % Say parking is easy

  • 85 % Say there's holiday spirit

  • 81 % Say it's dog friendly

  • 79 % Say there's wildlife

  • 68 % Say it's quiet

  • 68 % Say kids play outside

  • 60 % Say they plan to stay for at least 5 years

  • 55 % Say people would walk alone at night

  • 54 % Say neighbors are friendly

  • 29 % Say streets are well-lit

  • 27 % Say it's walkable to grocery stores

  • 24 % Say it's walkable to restaurants

  • 22 % Say there are community events

  • 14 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "You have to drive but most stores are close by. The main roads have public transportation that will bring you into the downtown areas. "
    0
    Flag
  • Anthony deleon
    "It’s quiet peaceful you can get a bird chirping. everyone waves high neighbors are nice. feel safe in this area."
    0
    Flag
  • Frederick G Manteghian
    "There are no sidewalks in most of Wolcott. We expect you to bag the poooop. we expect you to bag your poooop. Seriously though, bag your poooop."
    0
    Flag
  • Jessica Ferguson
    "It’s very quiet and there is tons of beautiful scenery/nature and wildlife. I hate that the town isn’t walkable though and doesn’t have sidewalks."
    0
    Flag
  • Drewie111
    "it's a relatively quiet town, but has a ton of things to do! there is a local bowling alley, great local grocery stores, a BEAUTIFUL 3+ mile reservoir to walk, a well kept park, family fun baseball field, and an EXCELLENT school system."
    4
    Flag
  • Christina S.
    "Car , bike, walking. There is public buses but not frequently used from wolcott. Generally roads, highway. "
    1
    Flag
  • KimC
    "Dog friendly neighborhood. Neighbors always looking out for your pet if one gets loose they will join in the search! "
    2
    Flag
  • Drewie111
    "Wolcott is a great, small community town that welcomes everyone. The school system is fantastic and I can't wait to have my own house in my hometown neighborhood"
    3
    Flag
  • Ortizlindy0414
    "I lived here for 7months and it’s really nice here so far but I can’t afford it so I’m looking for a better place for my daughter and I"
    2
    Flag
  • Jacob P.
    "I grew up in wolcott and have always really liked this town. I am currently looking to buy a bigger house still in wolcott. "
    2
    Flag
  • Sara J.
    "Besides the roads needing to be paved (potholes) it’s fine, near a main road so traffic is heavy at times "
    1
    Flag
  • Cheryl b.
    "I think Wolcott has great schools. My son went to the schools here. They also have a great walking trail for kids and adults. Lots of after school sports with a nice football field at the high school. Park and recreational activities "
    1
    Flag
  • Heather G.
    "Very dog friendly in wolcott... most sections have large areas for the pets to do there business. Most owners pick up there dogs messes "
    0
    Flag
  • Matthew T.
    "I have live here 10 years and love it. small town feel with access to neighboring cities for everything you could want. privacy. freindly. "
    0
    Flag
  • Drewie111
    "small community with a FANTASTIC school system, local reservoir to walk your pets (3+ miles along the lake), and 3 dunkin donuts"
    2
    Flag
  • Cheryl M.
    "I've lived in Wolcott for over 40 years and I love it. Its grown a lot over the years but still has the small town feel. "
    0
    Flag
  • Cameron G.
    "small community of families whose grandparents and great grandparents built the houses we live in. with a community club that most enjoy"
    0
    Flag

Market trends in Wolcott

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
49
7MoM

Home Value

Trulia Estimate
$1.03M
Since last month
$300 (0%)
Since last year
Increased$163K (+18.8%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +172% in the last 10 years
MonthEstimated value
2026
September 2026$1.03M
August 2026$1.03M
July 2026$1.04M
June 2026$1.03M
May 2026$1.04M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
29 Cole Drive, Wolcott, CT
0.36
Single-Family Home
$695,000
07/24/26
4
3
3,277
352 Center Street, Wolcott, CT
0.18
Single-Family Home
$495,000
08/17/26
3
2.5
2,588
120 Catering Road, Wolcott, CT
0.33
Single-Family Home
$635,000
06/24/26
4
2.5
2,375
1038 Woodtick Road, Wolcott, CT
0.20
Single-Family Home
$520,000
02/11/26
3
2.5
2,372
11 Cole Drive, Wolcott, CT
0.46
Single-Family Home
$700,000
09/26/25
3
3.5
4,075
8 Lindsley Drive, Wolcott, CT
0.25
Single-Family Home
$555,000
09/16/26
3
2
2,317
26 Lindsley Drive, Wolcott, CT
0.33
Single-Family Home
$535,000
06/25/26
3
2
2,081
109 Ransom Hall Road, Wolcott, CT
0.61
Single-Family Home
$550,000
03/03/26
3
2.5
2,188
1209 Woodtick Road, Wolcott, CT
0.65
Single-Family Home
$530,000
01/22/26
3
2.5
2,362
50 Kalko Drive, Wolcott, CT
0.69
Single-Family Home
$515,000
08/21/26
5
2
2,041

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
971 Woodtick Road, Wolcott, CT 06716
0.18
$546,600
4
2.5
2,335
Off Market
352 Center Street, Wolcott, CT 06716
0.18
$495,000
3
2.5
2,588
Recently Sold
1038 Woodtick Road, Wolcott, CT 06716
0.20
$520,000
3
2.5
2,372
Recently Sold
969 Woodtick Road, Wolcott, CT 06716
0.20
$390,000
2
1
1,198
Recently Sold
8 Lindsley Drive, Wolcott, CT 06716
0.25
$555,000
3
2
2,317
Recently Sold
90 Harrison Drive, Wolcott, CT 06716
0.27
$1,399,700
6
5.5
8,947
Off Market
15 Catering Road, Wolcott, CT 06716
0.28
$233,100
1
1
640
Off Market
270 Center Street, Wolcott, CT 06716
0.30
$337,600
4
2
1,652
Off Market
20 Lindsley Drive, Wolcott, CT 06716
0.31
$474,999
4
2.5
2,726
For Sale
111 Catering Road, Wolcott, CT 06716
0.32
$392,600
3
1
1,099
Off Market
120 Catering Road, Wolcott, CT 06716
0.33
$635,000
4
2.5
2,375
Recently Sold

Price and Tax history

DateEventPrice
May 19, 2026
Source: Smart MLS #24108031
PriceChange
$1,100,000
Price increased by 19%
Jun 30, 2025
Source: Smart MLS #24108031
Listed For Sale
$925,000
Jun 4, 2025
Source: Smart MLS #24082706
ListingRemoved
$900,000
Mar 24, 2025
Source: Smart MLS #24082706
Listed For Sale
$900,000
Mar 23, 2025
Source: Smart MLS #24066421
ListingRemoved
$900,000

LGBTQ Local Legal Protections

Donald L. Orsini, Don Orsini Realty, LLC, (203) 525-5134
Agent Phone: (203) 525-5134
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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Frequently asked questions about 20 Upson Road

  • What is the estimated monthly payment for 20 Upson Road?
    Based on a $1,100,000 list price with 20% down at today's rates, the estimated monthly payment for 20 Upson Road in Wolcott, CT is approximately $8,025 (about $5,997 principal & interest, $1,953 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • What do residents say about Wolcott?
    Residents describe Wolcott, CT as well-kept, easy to park in, and dog-friendly. Most residents say you need a car. See homes for sale in Wolcott, CT.
  • What are the closest schools to 20 Upson Road?
    The closest schools to 20 Upson Road in Wolcott, CT are Alcott School (Pre-K/Elementary, rated 8/10), Tyrrell Middle School (rated 6/10), Wolcott High School (rated 6/10).
  • What is 20 Upson Road estimated to be worth?
    Trulia's estimated value for 20 Upson Road in Wolcott, CT is $1,032,100.
  • Does 20 Upson Road have air conditioning?
    Yes, 20 Upson Road in Wolcott, CT has air conditioning.
  • Does 20 Upson Road have a pool?
    Yes, 20 Upson Road in Wolcott, CT has a pool.
20 Upson Road, Wolcott, CT 06716 is a 5 bedroom, 4 bathroom, 4,681 sqft single-family home built in 1964. This property is currently available for sale and was listed by Smart MLS on Jun 30, 2025. The MLS # for this home is MLS# 24108031.