414 Winthrop Rd, Deep River, CT 06417
OFF MARKET

$311,100

Trulia Estimate
  • 2 Beds
  • 1 Bath
  • 1,290 sqft (on 1 acre)

414 Winthrop Rd, Deep River, CT 06417

Est. Refi. Payment $2,232/mo*
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Home Value

Trulia Estimate
$311K
Since last month
Decreased$8K (-2.6%)
Since last year
Increased$12K (+4%)
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 +48% in the last 10 years
MonthEstimated value
2026
September 2026$315K
August 2026$323K
July 2026$314K
June 2026$322K
May 2026$319K
April 2026$297K
March 2026$304K
February 2026$283K
January 2026$285K
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
0.23
Single-Family Home
$568,000
08/14/26
3
2
1,984
36 Laurel Wood Dr, Deep River, CT
0.41
Single-Family Home
$450,000
05/22/26
3
2
1,789
200 Westbrook Road, Deep River, CT
0.82
Single-Family Home
$414,900
12/23/25
3
1.5
1,432
538 Winthrop Road, Deep River, CT
0.58
Single-Family Home
$300,000
04/30/26
2
1
650
51 Witch Hazel Drive, Deep River, CT
0.59
Single-Family Home
$750,000
07/13/26
3
3
2,231
16 Glen Grove Road, Deep River, CT
0.29
Single-Family Home
$850,000
09/09/26
4
2.5
2,782
57 Witch Hazel Drive, Deep River, CT
0.70
Single-Family Home
$610,000
05/12/26
3
2.5
1,887
112 Cedar Swamp Road, Deep River, CT
0.51
Single-Family Home
$605,000
04/29/26
4
3
2,969
7 Bushy Hill Road, Deep River, CT
0.63
Single-Family Home
$700,000
10/29/25
4
2.5
2,828
32 Pinewood Trail, Deep River, CT
0.38
Single-Family Home
$825,000
11/18/25
4
3.5
3,697

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
51 Cedar Lake Road, Deep River, CT 06417
0.20
$853,700
2
2
2,123
Off Market
460 Winthrop Road, Deep River, CT 06417
0.19
$410,500
3
1.5
1,626
Off Market
Cedar Lake Road, Deep River, CT 06417
0.26
-
-
-
-
Off Market
365 Winthrop Road, Deep River, CT 06417
0.23
$568,000
3
2
1,984
Recently Sold
61 Cedar Lake Road, Deep River, CT 06417
0.27
$1,075,000
3
3.5
3,864
Off Market
16 Glen Grove Road, Deep River, CT 06417
0.29
$850,000
4
2.5
2,782
Recently Sold
Cedar Swamp Road, Deep River, CT 06417
0.35
$175,000
-
-
-
Recently Sold
20 Glen Grove Road Extension, Deep River, CT 06417
0.33
$411,200
3
1.5
1,284
Off Market
2 Pinewood Trail, Deep River, CT 06417
0.37
$693,800
3
3.5
2,403
Off Market
32 Pinewood Trail, Deep River, CT 06417
0.38
$888,600
4
3.5
3,697
Off Market
Westbrook Road, Deep River, CT 06417
0.45
-
-
-
-
Off Market
112 Cedar Swamp Road, Deep River, CT 06417
0.51
$605,000
4
3
2,969
Recently Sold

Local Information

  • Map ViewExplore the area around 414 Winthrop Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1955
1 acre lot
1,290 sqft
$241/sqft
Garage

About this House

This single-family home is located at 414 Winthrop Rd, Deep River, CT. 414 Winthrop Rd is in Deep River, CT and in ZIP code 06417. This property has 2 bedrooms, 1 bathroom and approximately 1,290 sqft of floor space. This property has a lot size of 1 acre and was built in 1955.
414 Winthrop Rd, Deep River, CT 06417 is a 2 bedroom, 1 bathroom, 1,290 sqft single-family home built in 1955. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $311,100, with a rent estimate of $2,417/month.

Home Details for 414 Winthrop Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 6
Heating & Cooling
Heating: GasHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 1

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: OtherPatio
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1955
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 1 acre

Price and Tax history

YearProperty taxTax assessment
2025
$4,435
$138,670
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 414 Winthrop Rd

  • What is 414 Winthrop Rd estimated to be worth?
    Trulia's estimated value for 414 Winthrop Rd in Deep River, CT is $311,100.
  • 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 414 Winthrop Rd?
    The closest schools to 414 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).
  • How big is the lot at 414 Winthrop Rd?
    The lot at 414 Winthrop Rd in Deep River, CT is about 1 acre.
  • Does 414 Winthrop Rd have a garage?
    Yes, 414 Winthrop Rd in Deep River, CT has a garage.

Apartments for Rent

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Off Market Homes Near 414 Winthrop Rd

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