39 Winthrop Road, Deep River, CT 06417
OFF MARKET

$2,406,000

Trulia Estimate
  • 3 Beds
  • 3.5 Baths
  • 3,478 sqft (on 12.45 acres)

39 Winthrop Road, Deep River, CT 06417

Est. Refi. Payment $16,755/mo*
Refinance Your Home
Currently Off Market - Sold Feb 14, 2025 for $2,200,000

Home Value

Trulia Estimate
$2.41M
Since last month
Increased$10K (+0.4%)
Since last year
Increased$155K (+6.9%)
Since last sale
Increased$212K (+9.6%)
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 +97% in the last 10 years
MonthEstimated value
2026
September 2026$2.41M
August 2026$2.4M
July 2026$2.43M
June 2026$2.37M
May 2026$2.35M
April 2026$2.38M
March 2026$2.4M
February 2026$2.36M
January 2026$2.32M
2025
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
47 Plains Road, Deep River, CT
0.45
Single-Family Home
$450,000
01/15/26
3
2
1,958
120 Warsaw Street, Deep River, CT
0.52
Single-Family Home
$441,000
05/21/26
3
1.5
2,283
89 Falls Landing Road, Deep River, CT
0.78
Single-Family Home
$826,000
08/31/26
4
2.5
3,204
129 Falls Landing Road, Deep River, CT
0.92
Single-Family Home
$640,000
12/19/25
4
2.5
2,550
92 Warsaw Street, Deep River, CT
0.49
Single-Family Home
$419,588
02/03/26
2
1
1,100
32 Pinewood Trail, Deep River, CT
1.24
Single-Family Home
$825,000
11/18/25
4
3.5
3,697
151 Bushy Hill Road, Deep River, CT
1.14
Single-Family Home
$775,000
04/15/26
3
4
2,611
41 Mitchel Terrace, Ivoryton, CT
1.22
Single-Family Home
$650,000
11/10/25
3
2.5
2,816
9 Brooks Lane, Ivoryton, CT
1.30
Single-Family Home
$775,000
08/21/26
3
3
2,887

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
4 Bahr Road, Deep River, CT 06417
0.29
-
4
1.5
1,744
Off Market
362 West Elm Street, Deep River, CT 06417
0.41
-
3
1
1,398
Off Market
47 Plains Road, Deep River, CT 06417
0.45
$450,000
3
2
1,958
Recently Sold
92 Warsaw Street, Deep River, CT 06417
0.49
$419,588
2
1
1,100
Recently Sold
120 Warsaw Street, Deep River, CT 06417
0.52
$441,000
3
1.5
2,283
Recently Sold
38 Rosemont Drive, Deep River, CT 06417
0.51
$626,900
3
2.5
2,400
Off Market
59 Rosemont Drive, Deep River, CT 06417
0.61
$500,600
3
2
2,332
Off Market
77 Falls Landing Road, Deep River, CT 06417
0.69
$749,900
4
2.5
3,143
For Sale
245-259 Kelsey Hill Road, Deep River, CT 06417
0.73
$688,900
3
1
1,150
Off Market
89 Falls Landing Road, Deep River, CT 06417
0.78
$826,000
4
2.5
3,204
Recently Sold
280 West Elm Street, Deep River, CT 06417
0.80
$654,000
3
1.5
2,040
Off Market

Local Information

  • Map ViewExplore the area around 39 Winthrop Road.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1985
12.45 acre lot
3,478 sqft
$692/sqft
Garage

About this House

A Rare Find! An amazing home in a special setting! Totally redone and updated 3,500 sqft. home, set upon a hill overlooking 3 ponds, 2 covered bridges, and a waterwheel. The main house has an open floor plan, huge eat-in kitchen, 5 fireplaces, generous Primary Suite with custom bath, spacious walk-in closet, and "Silo" sitting area or home office. The lower level has been finished with a Gym, or Cardio Room, Sauna & Full bath which could easily become additional bedrooms or other living area. An abundance of outdoor entertainment is available with a large Stone & Brick patio with a built-in fireplace, and a heated in-ground pool with Gazebo and Cabana. Additional features include Central air, Central Vac, Irrigation System, and a whole house generator system. 2 beautiful garages. One 3,000 sqft. 5 car garage with spacious shop area and a 1,000 sqft. apartment above. One 1,400 sqft. 4 car garage with 700 sqft. apartment above. Each apartment can be guest accommodations, an in law apartment or provide rental income. All privately set on over 12 acres.
39 Winthrop Road, Deep River, CT 06417 is a 3 bedroom, 4 bathroom, 3,478 sqft single-family home built in 1985. It last sold for $2,200,000 on Feb 14, 2025 (12% below the $2,495,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,406,000, with a rent estimate of $5,204/month.
Last check for updates: about 1 hour ago
Listed by Craig Milton, (860) 391-3811
Re/Max Valley Shore, (860) 388-1228
Bought with: Amber Bova, (860) 801-3474, William Raveis Real Estate, (203) 453-0391
Source: Smart MLS, MLS#24037674

Home Details for 39 Winthrop Road

Interior Features

Interior Details
Basement: Full,FinishedNumber of Rooms: 9Types of Rooms: Master Bedroom, Bedroom, Bathroom, Dining Room, Family Room, Kitchen, Living Room, Other, Rec Play Room, Sun Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3478 Square Feet
Appliances & Utilities
Appliances: Oven/Range, Refrigerator, Washer, Dryer, Wine Cooler, Water HeaterDryerLaundry: Upper LevelRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,PropaneHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 5Has a Fireplace
Windows, Doors, Floors & Walls
Window: Thermopane Windows
View
Has a ViewView: Water

Exterior Features

Exterior Home Features
Roof: Asphalt FiberglassPatio / Porch: Enclosed, Porch, PatioOther Structures: Gazebo, CabanaFoundation: Concrete PerimeterHas a Private Pool
Parking & Garage
Number of Garage Spaces: 9Number of Covered Spaces: 9No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 9Parking: Barn,Detached,Paved,Driveway
Pool
Pool: Heated, In GroundPool
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 3478 Square Feet

Property Information

Year Built
Year Built: 1985
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 2644594

Price & Status

Price
List Price: $2,495,000
Status Change & Dates
Off Market Date: Fri Feb 14 2025Possession Timing: .

Active Status

MLS Status: Closed

Media

Location

Direction & Address
City: Deep RiverCommunity: Winthrop
School Information
Elementary School: Deep RiverHigh School: Per Board of Ed

Agent Information

Buyer Agent
Buyer Company Name: The One Team At William Raveis Real Estate

Building

Building Area
Building Area: 3478 Square Feet

HOA

No HOA

Lot Information

Lot Area: 12.45 Acres

Energy

Energy Efficiency Features: Windows

Miscellaneous

BasementMls Number: 24037674Attic: NoneWater ViewWater View: WaterAbove Grade Unfinished Area: 3478

Price and Tax history

DateEventPrice
Feb 14, 2025
Source: Smart MLS #24037674
Sold
$2,200,000
Oct 7, 2024
Source: Smart MLS #24037674
PriceChange
$2,495,000
Price decreased by 15%
Sep 13, 2024
Source: Smart MLS #24037674
PriceChange
$2,950,000
Price decreased by 8%
Aug 19, 2024
Source: Smart MLS #24037674
Listed For Sale
$3,200,000

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

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 39 Winthrop Road

  • What is 39 Winthrop Road estimated to be worth?
    Trulia's estimated value for 39 Winthrop Road in Deep River, CT is $2,406,000.
  • What is the price history for 39 Winthrop Road?
    39 Winthrop Road in Deep River, CT last sold for $2,200,000 in February 2025.
  • 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.
  • Does 39 Winthrop Road have air conditioning?
    Yes, 39 Winthrop Road in Deep River, CT has air conditioning.
  • Does 39 Winthrop Road have a pool?
    Yes, 39 Winthrop Road in Deep River, CT has a pool.

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