75 Woolson Street, Watertown, CT 06795
OFF MARKET

$354,000

Trulia Estimate
  • 2 Beds
  • 2 Baths
  • 1,182 sqft (on 0.25 acres)

75 Woolson Street, Watertown, CT 06795

Est. Refi. Payment $2,409/mo*
Refinance Your Home
Currently Off Market - Sold Dec 23, 2024 for $320,000

Home Value

Trulia Estimate
$354K
Since last month
Increased$2K (+0.5%)
Since last year
Increased$22K (+6.5%)
Since last sale
Increased$32K (+9.9%)
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 +149% in the last 10 years
MonthEstimated value
2026
August 2026$352K
July 2026$350K
June 2026$344K
May 2026$342K
March 2026$345K
February 2026$341K
January 2026$337K
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
56 Baldwin Street, Watertown, CT
0.23
Single-Family Home
$304,000
12/19/25
2
1.5
1,287
122 Chestnut Grove Road, Watertown, CT
0.20
Single-Family Home
$365,000
07/31/26
3
1.5
1,376
28 Wilder Street, Watertown, CT
0.23
Single-Family Home
$275,000
08/27/26
2
2
1,832
15 Roberts Avenue, Watertown, CT
0.15
Single-Family Home
$337,000
01/02/26
3
2
1,192
14 Northfield Road, Watertown, CT
0.14
Single-Family Home
$285,000
12/12/25
3
1.5
1,543
27 Baldwin Street, Watertown, CT
0.20
Single-Family Home
$427,000
12/02/25
3
1.5
1,480
111 Woolson Street, Watertown, CT
0.07
Single-Family Home
$325,000
08/19/26
1
1
1,116
101 Cutler Street, Watertown, CT
0.25
Single-Family Home
$375,000
12/22/25
3
2
1,728
27 Roberts Avenue, Watertown, CT
0.14
Single-Family Home
$450,000
03/31/26
4
2
1,620
33 Chestnut Grove Road, Watertown, CT
0.15
Single-Family Home
$285,000
07/10/26
4
2
1,499

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
55 Woolson Street, Watertown, CT 06795
0.04
$485,300
4
2.5
2,553
Off Market
111 Woolson Street, Watertown, CT 06795
0.07
$325,000
1
1
1,116
Recently Sold
12 Woolson Street, Watertown, CT 06795
0.11
$477,033
4
1.5
2,022
Recently Sold
55 Roberts Street, Watertown, CT 06795
0.13
$333,400
4
1.5
1,600
Off Market
Lot#14D Litchfield Road, Watertown, CT 06795
0.12
$90,000
-
-
-
Recently Sold
54 Litchfield Road, Watertown, CT 06795
0.10
$279,900
4
1
1,461
For Sale
19 Roberts Street, Watertown, CT 06795
0.14
$276,000
2
1.5
820
Off Market
52 Chestnut Grove Road, Watertown, CT 06795
0.09
$336,000
4
2
1,351
Off Market
27 Roberts Avenue, Watertown, CT 06795
0.14
$450,000
4
2
1,620
Recently Sold
66 Litchfield Road, Watertown, CT 06795
0.11
$431,100
3
1.5
1,632
Off Market
15 Roberts Avenue, Watertown, CT 06795
0.15
$337,000
3
2
1,192
Recently Sold

Local Information

  • Map ViewExplore the area around 75 Woolson Street.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1830
Lot Size
0.25 acres
Living Area
1,182 sqft
Price/Sqft
$299
Parking
1 Car Garage

About this House

As you travel through the renowned Taft School neighborhood the history of the area reveals itself to you; there are the homes such as those on Woolson Street that were built over the town's first century of settlement, modest and charming - highlighting a time when practical and purposeful were the goals in constructing an American home. It is in this historic village that you find 75 Woolson Street; an unassuming colonial set into the hillside. Each passing steward seems to have respected the importance of preserving the homes two hundred year history; with no modifications having been made to the structure, the modern mechanical updates have been made including central air conditioning, natural gas conversion, and a functional wood burning fireplace. Interestingly, because of this, one can design to a multitude of tastes since the traditional layout is one of simplicity; again highlighting the practicality of this era of construction. In this vein you can reconsider the use of the first floors second living room, which with few modifications, can be altered to a bedroom. Additionally, the manageable parcel has two driveways, one that runs alongside the home with a plateued parking area and the second directly in front of the foundation level garage. History, charm, and convenience are what define Woolson Street. A must see.
75 Woolson Street, Watertown, CT 06795 is a 2 bedroom, 2 bathroom, 1,182 sqft single-family home built in 1830. It last sold for $320,000 on Dec 23, 2024 (3% below the $329,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $354,000, with a rent estimate of $2,170/month.
Last check for updates: about 13 hours ago
Listed by Michael Caporizzo, (203) 644-5228
William Pitt Sotheby's Int'l, (860) 868-6600
Erin Caporizzo, (860) 868-6600
William Pitt Sotheby's Int'l, (860) 868-6600
Bought with: Erika Henkel, (203) 947-2059, Coldwell Banker Realty, (860) 354-4111
Source: Smart MLS, MLS#24053552

Home Details for 75 Woolson Street

Interior Features

Interior Details
Basement: FullNumber of Rooms: 6Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Living Room, Sun Room
Beds & Baths
Number of Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1182 Square Feet
Appliances & Utilities
Appliances: Electric Range, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Lower LevelRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Deck, CoveredOther Structures: Shed(s)Foundation: StoneNo Private Pool
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageHas an Attached GarageParking Spaces: 1Parking: Attached
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1182 Square Feet

Property Information

Year Built
Year Built: 1830
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: ClapboardNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 917770

Price & Status

Price
List Price: $329,000
Status Change & Dates
Off Market Date: Wed Nov 06 2024Possession Timing: Negotiable

Active Status

MLS Status: Closed

Location

Direction & Address
City: WatertownCommunity: Taft School
School Information
Elementary School: Per Board of EdHigh School: Per Board of Ed

Building

Building Area
Building Area: 1182 Square Feet

Community

Community Features: Lake, Park, Private School(s), Stables/Riding, Tennis Court(s)

HOA

No HOA

Lot Information

Lot Area: 10890 sqft

Miscellaneous

BasementMls Number: 24053552Attic: NoneAbove Grade Unfinished Area: 1182

Additional Information

LakeParkPrivate School(s)Stables/RidingTennis Court(s)

Price and Tax history

DateEventPrice
Dec 23, 2024
Source: Smart MLS #24053552
Sold
$320,000
Oct 31, 2024
Source: Smart MLS #24053552
PriceChange
$329,000
Price decreased by 4%
Oct 17, 2024
Source: Smart MLS #24053552
Listed For Sale
$343,000
Jun 29, 2018
Source: Smart MLS #170077287
Sold
$161,000
May 4, 2018
Source: Agent Provided
Pending
$169,900

Market trends in Watertown

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$374K
Sale-to-List Price
—
Price per sq ft
$236
Available listings
54
1MoM

Around this home

What Locals Say about Watertown

At least 160 Trulia users voted on each feature.

  • 88 % Say car is needed

  • 86 % Say yards are well-kept

  • 80 % Say parking is easy

  • 77 % Say it's dog friendly

  • 73 % Say there's holiday spirit

  • 63 % Say it's quiet

  • 60 % Say kids play outside

  • 60 % Say people would walk alone at night

  • 56 % Say neighbors are friendly

  • 56 % Say they plan to stay for at least 5 years

  • 55 % Say there's wildlife

  • 49 % Say streets are well-lit

  • 48 % Say there are sidewalks

  • 42 % Say it's walkable to restaurants

  • 35 % Say it's walkable to grocery stores

  • 31 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Colette.dobkins
    "They would love it. Very nice and quiet. Friendly . I lived here 16 years . Raised my daughter here. "
    0
    Flag
  • Dashmurtishi
    "Well manicured with a bunch of well versed designed homes Beautiful neighborhood by a winery with beautiful views and privacy "
    0
    Flag
  • Eric Brown
    "Walks through the neighborhood and chats with neighbors while walking the dog. Meeting up with neighbors for cookouts. "
    0
    Flag
  • Lily Retallick
    "There is a lot of dog owners in Watertown and they are always taking them for walks and clean up after their dogs. The dogs are people friendly too! "
    0
    Flag
  • Trulia User
    "I don’t have a dog so I’m not sure but they have a park where you can walk dogs and everyone seems to have pets. "
    0
    Flag
  • Minicucci.erica
    "Main Street can get busy at popular hours of the day but there are ways to get around town to avoid traffic"
    2
    Flag
  • Emily L. R.
    "Lots of side walks, and they’re building a dog park but I’m not sure how far along in the process they are. "
    1
    Flag
  • Emily L. R.
    "There are downtown block parties in the summer, there are fundraisers, there’s a community theater, there are several churches, there is Halloween trunk trick or treating, there are seasonal parades through town and festivals at veterans park!"
    0
    Flag
  • Browna57
    "My neighborhood is an old Italian family-oriented area of Watertown. Everyone is very friendly, and my street is quiet. "
    2
    Flag
  • Scorpionrkg
    "It’s friendly quaint and quiet not too much stress very economicalGuess it’s a good safe neighborhood to raise your kids and go to school go shopping good quiet community I would be happy to live here I was just visiting hope it was helpful to everybody thank you have a great day"
    12
    Flag
  • Hiredjkg
    "People walk their dogs all the time up and down the street. There are also some parks nearby. From what I see they are all leashed and the people normally carry a bag for the feces. "
    1
    Flag
  • Em T.
    "great for young families! try fino pizza, it’s a great restaurant. people are friendly and trick or treating is huge. nice place to grow up in"
    2
    Flag
  • Arroyorosie
    "they would live the fact that there is a dog park here in Watertown, the Oriole are friendly. it is a quaint little town"
    0
    Flag
  • Dashmurtishi
    "Everyone has their dog on a leash on the daily walks Dogs are friendly and not barking at you when you stop n say hi to your walking neighbors Have a sidewalk for the kids and the dogs to walk on one side of the street and still feel safe around the dogs Remember it’s not the dog it’s the owners control of the dog "
    0
    Flag
  • C. Nicole
    "I've lived here in town my whole life. I loved growing up here and am glad I'm able to now taise my own family here. It's truly a great location!! "
    0
    Flag
  • Cat T.
    "Watertown is pretty good. It’s next to Waterbury which has a mall and other places to visit. My nerighborhood is amazing here, the neighbors are all very close and I even walk one of my neighbor’s dogs for her lol. I haven’t had any troubles with the public schools here either. Main Street has lots of things to visit. "
    0
    Flag
  • Cat T.
    "The side walks are great and they’re always shoveled in the winter. The traffic is very light and cars hardly pass by so it’s pretty nice. "
    2
    Flag
  • Csrelyea
    "Quiet and friendly. Neighbors wave and kids play freely. Lots of birds, and great sunrise and sunsets. "
    15
    Flag
  • Val3487
    "it's ok I don't go to far !!! I work about 4 minutes from my home !! nice and quiet the roads here are bad need to be repaired "
    2
    Flag
  • Rick M.
    "Safe & beautiful neighborhood, good neighbors. Family friendly activities available. Good schools nearby "
    0
    Flag
  • Esson
    "Live here and love it been here forever. My neighbors are so awesome. Always kind and quiet since day one I moved here."
    1
    Flag
  • Daniellerdesjardins
    "I’ve lived here since I was a kid. It will always be home despite the changes occurring in the neighborhood. "
    0
    Flag
  • Matthewbarnes873
    "It’s the first place I’ve lived on my own and I raise my son here. Everything great is around such as schools, work, and places to eat"
    0
    Flag
  • Sammygood81
    "Great place to live with children and family love taking walks to the park with the beautiful beach "
    0
    Flag
  • Carlim54
    "I've livin in the neighborhood for a little over 3 years and I can really say is a great area to live in. Is quite and peaceful and great for raising a family. The school system is fantastic. Oakville is overall a great area."
    0
    Flag

LGBTQ Local Legal Protections

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.

Frequently asked questions about 75 Woolson Street

  • What is 75 Woolson Street estimated to be worth?
    Trulia's estimated value for 75 Woolson Street in Watertown, CT is $354,000.
  • What is the price history for 75 Woolson Street?
    75 Woolson Street in Watertown, CT last sold for $320,000 in December 2024.
  • Is Watertown a buyer's or seller's market?
    Watertown is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Watertown?
    The median sale price in Watertown is $374K.
  • Does 75 Woolson Street have air conditioning?
    Yes, 75 Woolson Street in Watertown, CT has air conditioning.
  • Does 75 Woolson Street have laundry facilities?
    Yes, 75 Woolson Street in Watertown, CT has in-unit laundry.

Explore by feature - Pet Friendly

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