20 Upson Road
Wolcott, CT 06716
5 Beds
3 Baths
4,681 sqft (on 36.14 acres)
5 Beds
3 Baths
4,681 sqft
(on 36.14 acres)
Local Information
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Description
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.
Home Highlights
Parking
6 Car Garage
Outdoor
Porch, Deck, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
$198
Listed
180+ days ago
Home Details for 20 Upson Road
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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 |
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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 |
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Days on Market: 180+ |
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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 |
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Price List Price: $925,000Price Per Sqft: $198 |
Status Change & Dates Possession Timing: Negotiable |
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MLS Status: Active |
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Direction & Address City: WolcottCommunity: Woodtick |
School Information Elementary School: Per Board of EdHigh School: Wolcott |
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Listing Agent Listing ID: 24108031 |
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Building Area Building Area: 4681 Square Feet |
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No HOA |
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Lot Area: 36.14 Acres |
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BasementMls Number: 24108031Attic: Crawl Space, Walk-upWater ViewWater View: WaterAttribution Contact: (203) 525-5134Above Grade Unfinished Area: 4681 |
Last check for updates: about 5 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.
Price History for 20 Upson Road
| Date | Price | Event | Source |
|---|---|---|---|
| 06/30/2025 | $925,000 | Listed For Sale | Smart MLS #24108031 |
| 06/04/2025 | $900,000 | ListingRemoved | Smart MLS #24082706 |
| 03/24/2025 | $900,000 | Listed For Sale | Smart MLS #24082706 |
| 03/23/2025 | $900,000 | ListingRemoved | Smart MLS #24066421 |
| 01/28/2025 | $900,000 | PriceChange | Smart MLS #24066421 |
| 01/02/2025 | $1,100,000 | Listed For Sale | Smart MLS #24066421 |
| 04/30/2024 | ListingRemoved | Smart MLS #170603647 | |
| 03/01/2024 | $999,000 | PriceChange | Smart MLS #170603647 |
| 10/11/2023 | $1,100,000 | Listed For Sale | Smart MLS #170603647 |
| 10/10/2023 | ListingRemoved | Smart MLS #170472962 | |
| 10/06/2022 | $1,100,000 | PriceChange | Smart MLS #170472962 |
| 05/31/2022 | $1,200,000 | PriceChange | Smart MLS #170472962 |
| 03/11/2022 | $1,100,000 | Listed For Sale | Smart MLS #170472962 |
| 12/02/2021 | ListingRemoved | Smart MLS #170404924 | |
| 05/28/2021 | $350,000 | Listed For Sale | Smart MLS #170404924 |
| 11/05/2019 | $490,000 | ListingRemoved | Agent Provided |
| 06/06/2019 | $490,000 | PriceChange | Agent Provided |
| 12/17/2018 | $899,000 | Listed For Sale | Agent Provided |
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $11,713 |
| Assessment | $326,000 |
Home facts updated by county records
Comparable Sales for 20 Upson Road
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.20 | Single-Family Home | $520,000 | 02/11/26 | 3 | 2.5 | 2,372 | |
0.46 | Single-Family Home | $700,000 | 09/26/25 | 3 | 3.5 | 4,075 | |
0.32 | Single-Family Home | $324,000 | 05/15/25 | 3 | 1.5 | 1,682 | |
0.78 | Single-Family Home | $850,000 | 07/22/25 | 4 | 3.5 | 4,310 | |
0.61 | Single-Family Home | $550,000 | 03/03/26 | 3 | 2.5 | 2,188 | |
0.65 | Single-Family Home | $530,000 | 01/22/26 | 3 | 2.5 | 2,362 | |
0.66 | Single-Family Home | $446,900 | 05/12/25 | 3 | 2.5 | 2,360 | |
0.65 | Single-Family Home | $572,900 | 01/16/26 | 3 | 2 | 2,043 | |
0.77 | Single-Family Home | $489,000 | 12/12/25 | 3 | 2.5 | 1,954 |
Assigned Schools
These are the assigned schools for 20 Upson Road.
- Tyrrell Middle School
- 6-8
- Public
- 510 Students
5/10GreatSchools RatingParent Rating AverageI have never met a student who is happy at tms. As a former student, teachers always say they are there for you, but are not understanding of students and their conditions at all! Kids here are ruthless, and there is no control over the school.Other Review5y ago - Alcott School
- PK-5
- Public
- 298 Students
7/10GreatSchools RatingParent Rating AverageAlcott School is a terrific school. I recommend it highly. It was also recently named the Most Outstanding Elementary School in CT.Parent Review10y ago - Wolcott High School
- 9-12
- Public
- 649 Students
6/10GreatSchools RatingParent Rating AverageI moved here from New York during my junior year, and I can honestly say I do not like this school at all. Starting with safety it’s terrible. At my old school in Long Island, we had to scan our student IDs just to get in the building. Here? Anyone can walk right in with the crowd in the morning, no questions asked. We even had an incident where a student from another school came in and no one noticed until an actual student pointed it out. If you care about school security, this is not the place. Academics are just okay. If you’re expecting one of the top schools, this isn’t it. Coming from one of the best public schools in Long Island, I had high expectations and they weren’t met. If you're looking for a school where most students go off to top colleges or even just college in general, this probably won’t be a great fit. Some teachers are great and supportive, but like every school, some really aren’t.What really brings this school down is how overly strict they are with policies, especially lateness and attendance. You’re allowed only six excused latenesses a year. After that, even if you have a doctor’s note or verified reason, they give you detention. I personally got detention for being late because of migraines, even though I’m on medication and the school is aware. They just don’t care.Same goes for attendance, if you miss too many days (even with a valid excuse), they can make you retake the class. As a senior, it’s frustrating trying to meet unrealistic expectations while dealing with college applications and senioritis.Overall, I wouldn’t recommend this school. If I could switch, I would. There are way better options out there, don’t settle. You’d only be making things harder for yourself and your child.Student Review11mo ago 
Check out schools near 20 Upson Road.
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
80 % 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
56 % Say people would walk alone at night
53 % 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
13 % Say there are sidewalks
Learn more about our methodology.
LGBTQ Local Legal Protections
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.
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.