285 Winthrop Rd, Deep River, CT 06417
OFF MARKET

$505,900

Trulia Estimate
  • 2 Beds
  • 2 Baths
  • 1,320 sqft (on 31 acres)

285 Winthrop Rd, Deep River, CT 06417

Est. Refi. Payment $3,582/mo*
Refinance Your Home

Home Value

Trulia Estimate
$506K
Since last month
Decreased$12K (-2.3%)
Since last year
Increased$58K (+13.3%)
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 +118% in the last 10 years
MonthEstimated value
2026
September 2026$499K
August 2026$510K
July 2026$489K
June 2026$499K
May 2026$487K
April 2026$488K
March 2026$506K
February 2026$463K
January 2026$437K
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
365 Winthrop Road, Deep River, CT
0.48
Single-Family Home
$568,000
08/14/26
3
2
1,984
36 Laurel Wood Dr, Deep River, CT
0.63
Single-Family Home
$450,000
05/22/26
3
2
1,789
32 Pinewood Trail, Deep River, CT
0.33
Single-Family Home
$825,000
11/18/25
4
3.5
3,697
16 Glen Grove Road, Deep River, CT
0.53
Single-Family Home
$850,000
09/09/26
4
2.5
2,782
200 Westbrook Road, Deep River, CT
0.87
Single-Family Home
$414,900
12/23/25
3
1.5
1,432
7 Bushy Hill Road, Deep River, CT
0.52
Single-Family Home
$700,000
10/29/25
4
2.5
2,828
28 Bahr Rd, Deep River, CT
1.02
Single-Family Home
$600,000
12/22/25
3
2
1,414
47 Plains Road, Deep River, CT
1.02
Single-Family Home
$450,000
01/15/26
3
2
1,958
112 Cedar Swamp Road, Deep River, CT
0.74
Single-Family Home
$605,000
04/29/26
4
3
2,969
179 Bushy Hill Road, Deep River, CT
0.91
Single-Family Home
$385,000
11/04/25
3
2.5
2,179

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
39 Pinewood Trail, Deep River, CT 06417
0.13
$779,200
3
2.5
2,566
Off Market
273 Winthrop Road, Deep River, CT 06417
0.17
$314,700
2
1
948
Off Market
32 Pinewood Trail, Deep River, CT 06417
0.33
$888,600
4
3.5
3,697
Off Market
2 Pinewood Trail, Deep River, CT 06417
0.36
$698,000
3
3.5
2,403
Off Market
Westbrook Road, Deep River, CT 06417
0.45
-
-
-
-
Off Market
365 Winthrop Road, Deep River, CT 06417
0.48
$568,000
3
2
1,984
Recently Sold
7 Bushy Hill Road, Deep River, CT 06417
0.52
$756,900
4
2.5
2,828
Off Market
103 Bushy Hill Road, Deep River, CT 06417
0.54
$769,000
3
2.5
1,716
For Sale
16 Glen Grove Road, Deep River, CT 06417
0.53
$850,000
4
2.5
2,782
Recently Sold
22 Nature Trail, Deep River, CT 06417
0.65
$708,700
3
2.5
2,284
Off Market
20 Glen Grove Road Extension, Deep River, CT 06417
0.74
$411,200
3
1.5
1,284
Off Market
Cedar Swamp Road, Deep River, CT 06417
0.74
$175,000
-
-
-
Recently Sold

Local Information

  • Map ViewExplore the area around 285 Winthrop Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1971
31 acre lot
1,320 sqft
$383/sqft
Garage

About this House

This single-family home is located at 285 Winthrop Rd, Deep River, CT. 285 Winthrop Rd is in Deep River, CT and in ZIP code 06417. This property has 2 bedrooms, 2 bathrooms and approximately 1,320 sqft of floor space. This property has a lot size of 31.00 acres and was built in 1971.
285 Winthrop Rd, Deep River, CT 06417 is a 2 bedroom, 2 bathroom, 1,320 sqft single-family home built in 1971. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $505,900, with a rent estimate of $2,611/month.

Home Details for 285 Winthrop Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 5
Heating & Cooling
Heating: OilHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 1

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1971
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 31.00 acres

Price and Tax history

YearProperty taxTax assessment
2025
$5,782
$180,790
Home facts updated by county records

Market trends in Deep River

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
20

Around this home

What Locals Say about Deep River

At least 15 Trulia users voted on each feature.

  • 100 % Say it's dog friendly

  • 95 % Say car is needed

  • 90 % Say there's wildlife

  • 87 % Say yards are well-kept

  • 83 % Say parking is easy

  • 81 % Say there's holiday spirit

  • 80 % Say kids play outside

  • 76 % Say people would walk alone at night

  • 76 % Say it's walkable to grocery stores

  • 74 % Say it's walkable to restaurants

  • 74 % Say streets are well-lit

  • 70 % Say neighbors are friendly

  • 57 % Say there are sidewalks

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

  • 53 % Say it's quiet

  • 46 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Timothy Ballantyne
    "Friendly helpful neighbors community support for different kinds of groups volunteer firefighters and ambulance "
    0
    Flag
  • Dave M.
    "the deep river muster, all my friends and family, great community!! deep river day in September. Small town America in New England!!"
    4
    Flag
  • Timothy B.
    "friendly neighborhood people helping each other out in bad weather. good support when things go bad. A nice place to live."
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 285 Winthrop Rd

  • What is 285 Winthrop Rd estimated to be worth?
    Trulia's estimated value for 285 Winthrop Rd in Deep River, CT is $505,900.
  • Is Deep River a buyer's or seller's market?
    Deep River is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Deep River?
    Residents describe Deep River, CT as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See recently sold homes in Deep River, CT.
  • What are the closest schools to 285 Winthrop Rd?
    The closest schools to 285 Winthrop Rd in Deep River, CT are Deep River Elementary School (Pre-K, rated 7/10), John Winthrop Middle School (rated 4/10), Valley Regional High School (rated 7/10).
  • Does 285 Winthrop Rd have a pool?
    Yes, 285 Winthrop Rd in Deep River, CT has a pool.
  • How big is the lot at 285 Winthrop Rd?
    The lot at 285 Winthrop Rd in Deep River, CT is about 31 acres.

Apartments for Rent

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Off Market Homes Near 285 Winthrop Rd

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