39 Winthrop Road

Closed 2/14/25Virtual Tour
Closed 2/14/25Virtual Tour
Gallery Image 1
Last Sold Price
$2,200,000
3 beds3,478 sqft$633/sqft
39 Winthrop Rd, Deep River, CT 06417

Description

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...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.
LISTING CLOSED: 02/14/2025 12:00 AM

  1. Listed by Craig Milton • Re/Max Valley Shore
    P: (860) 391-3811 C: (860) 388-4663 craigmilton@remax.net

Property Details for 39 Winthrop Road

Status
Closed
MLS #
24037674
Days on Market
152
Taxes
$28,674 / year
HOA Fees
-
Condo/Co-op Fees
-
Property Type
Single Family
MLS Type
Residential
Year Built
1985
Lot Size
12.45 AC / 542,322 SF
County
Middlesex County
Basement Description
Full, Fully Finished
Direct Waterfront
No
Expected Active Date
08-19-2024
Garages Number
9
Neighborhood
Winthrop
Style
Colonial
Garage Parking Info
Barn, Detached Garage, Paved, Driveway
Swimming Pool
Yes
Expected On Market Date
08-19-2024

Recent comparable sales

Median sold price

$730,000

Avg days on market

60

Sale-to-list ratio

100.6%

Deep River, CT

9 comparable properties found

$825,000 | 32 Pinewood Trail, Deep River, CT 06417
1

$825,000

Sold 11/18/25

4
Bedrooms
3,697
Square Feet
3.54
Acres

32 Pinewood Trail, Deep River, CT 06417

$730,000 | 56 Shailer Pond Road, Deep River, CT 06417
2

$730,000

Sold 07/29/26

3
Bedrooms
2,848
Square Feet
1.84
Acres

56 Shailer Pond Road, Deep River, CT 06417

a front view of a house with a yard
3

$775,000

Sold 04/15/26

3
Bedrooms
2,611
Square Feet
1.8
Acres

151 Bushy Hill Road, Deep River, CT 06417

$810,000 | 641 Winthrop Road, Deep River, CT 06417
4

$810,000

Sold 04/04/25

3
Bedrooms
2,584
Square Feet
1.6
Acres

641 Winthrop Road, Deep River, CT 06417

$750,000 | 51 Witch Hazel Drive, Deep River, CT 06417
5

$750,000

Sold 07/13/26

3
Bedrooms
2,231
Square Feet
2.18
Acres

51 Witch Hazel Drive, Deep River, CT 06417

6

$500,000

Sold 04/25/25

3
Bedrooms
3
Bathrooms
1,951
Square Feet
3.57
Acres

109 Witch Hazel Drive, Deep River, CT 06417

$605,000 | 112 Cedar Swamp Road, Deep River, CT 06417
7

$605,000

Sold 04/29/26

4
Bedrooms
2,969
Square Feet
2.45
Acres

112 Cedar Swamp Road, Deep River, CT 06417

$726,500 | 220 Bushy Hill Road, Deep River, CT 06417
8

$726,500

Sold 07/08/25

4
Bedrooms
3,133
Square Feet
2.3
Acres

220 Bushy Hill Road, Deep River, CT 06417

9

$343,688

Sold 06/17/25

3
Bedrooms
2.5
Bathrooms
2,130
Square Feet
3.26
Acres

6 Westbrook Road, Deep River, CT 06417

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Location

Listing Courtesy of Re/Max Valley Shore, Craig Milton

Sold By William Raveis Real Estate, Amber Bova

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Virtual Tour

Building Information for 39 Winthrop Road

Stories-Year Built1985Building Size-Lot Size12.45 AC / 542,322 SF

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$13,572 per month

30 year fixed, 6.55% Interest

Principal and Interest

$11,182

Property Taxes

$2,390

HOA Dues

$0

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Property Information for 39 Winthrop Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: GPS Friendly
  • Elementary School: Deep River
  • High School: Per Board of Ed
  • Latitude: 41.365639
  • Longitude: -72.460159
  • State: Connecticut
Parking
  • Parking Total Spaces: 9
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2024-June 2025
  • Property Tax: $28,674
Interior and Exterior Features
Exterior Features
  • Exterior Features: Porch-Enclosed, Gazebo, Porch, Cabana, Patio
  • Pool Description: Heated, In Ground Pool
  • Waterfront Description: View
Interior Features
  • Appliances Included: Oven/Range, Refrigerator, Washer, Dryer, Wine Chiller
  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Attic YN: No
  • Fireplaces Total: 5
  • Laundry Room Info: Upper Level
  • Laundry Room Location: 2nd Floor
  • Rooms Additional: Exercise Room, Steam/Sauna, Sitting Room, Workshop
  • Rooms Total: 9
Room 1
  • Room Entry Order: 1
  • Room Features: Fireplace
  • Room Length: 19.0
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 22.0
Room 2
  • Room Entry Order: 10
  • Room Features: Steam/Sauna
  • Room Length: 30.0
  • Room Level: Lower
  • Room Type: Rec/Play Room
  • Room Width: 33.0
Room 3
  • Room Entry Order: 11
  • Room Length: 12.0
  • Room Level: Lower
  • Room Type: Other
  • Room Width: 19.0
Room 4
  • Room Entry Order: 12
  • Room Level: Lower
  • Room Type: Full Bath
Room 5
  • Listing Key: 1EF32E9173481EA5E0631401100AA098
  • Room Entry Order: 13
  • Room Length: 7.0
  • Room Level: Lower
  • Room Type: Other
  • Room Width: 6.0
Room 6
  • Room Entry Order: 2
  • Room Features: Breakfast Bar,Breakfast Nook
  • Room Length: 19.0
  • Room Level: Main
  • Room Type: Eat-In Kitchen
  • Room Width: 21.0
Room 7
  • Room Entry Order: 3
  • Room Features: Fireplace
  • Room Length: 12.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 22.0
Room 8
  • Room Entry Order: 4
  • Room Length: 9.0
  • Room Level: Main
  • Room Type: Sun Room
  • Room Width: 15.0
Room 9
  • Listing Key: 1EF32E9173481EA5E0631401100AA098
  • Room Entry Order: 5
  • Room Length: 6.0
  • Room Level: Main
  • Room Type: Half Bath
  • Room Width: 5.0
Room 10
  • Room Entry Order: 6
  • Room Features: Fireplace
  • Room Length: 17.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 23.0
Room 11
  • Room Entry Order: 7
  • Room Features: Bedroom Suite,Built-Ins,Fireplace,Full Bath,Walk-In Closet
  • Room Length: 28.0
  • Room Level: Upper
  • Room Type: Primary BR Suite
  • Room Width: 17.0
Room 12
  • Room Entry Order: 8
  • Room Features: Jack & Jill Bath
  • Room Length: 17.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 13.0
Room 13
  • Room Entry Order: 9
  • Room Features: Jack & Jill Bath
  • Room Length: 13.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 13.0
Property
Property and Assessments
  • Color: Tan
  • Construction Description: Concrete
  • Driveway Type: Paved
  • Exterior Siding: Vinyl Siding
  • Foundation Type: Concrete
  • Fuel Tank Location: In Ground
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle, Fiberglass Shingle
  • Year Built: 1985
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: Detached
  • In Law Apartment: Yes
  • Living Area SQFT Per Public Records: 0
Lot Information
  • Lot Description: Water View
  • Parcel Number: 2644594
  • Sq Ft Est Heated Above Grade: 3478.0
  • Sq Ft Total: 3478.0
  • Zoning: R80
Utilities
  • Energy Features: Generator, Thermopane Windows
  • Heat Fuel Type: Propane
  • Hot Water Description: Other
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Tenant

Property History for 39 Winthrop Road

DateEvent & SourcePriceAppreciation
Feb 8, 2025

Closed (Public Record)

Public Record #1551762972

$2,200,000—
DateEvent & SourcePrice
02/08/2025

Closed (Public Record)

Public Record #1551762972

$2,200,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 39 Winthrop Road

Taxable ValueLand$146,440Additions$792,680Total$939,120
Tax Record2024$30,033 ($2,503 / month)
Home Facts
Lot Size542,322 SqFtStyleMulti-Family Dwelling (2-4)ZoningR80CountyLOWER CONNECTICUT RIVERAPNDEEP M:38 L:7-3

Schools near 39 Winthrop Road

This home is within Regional School District 04.
Rating
School
Type
Grades
Distance
Deep River Elementary School
Public - PK to 6
John Winthrop Middle School
Public - 7 to 8
Valley Regional High School
Public - 9 to 12
Rating
School
Distance
Deep River Elementary School
PublicPK to 6

John Winthrop Middle School
Public7 to 8

Valley Regional High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 39 Winthrop Road, Deep River, CT 06417
$2,200,000
3
3,478
542,322
410 Winthrop Road, Deep River, CT 06417
$325,000
3
3,036
78,408
384 Winthrop Road, Deep River, CT 06417
–
4
1
1,834
74,923
Lot 9 Cedar Swamp Road, Deep River, CT 06417
$80,000
–
–
–
208,652
Lot 7 Cedar Swamp Road, Deep River, CT 06417
$110,000
–
–
–
207,781
10 Westbrook Road, Deep River, CT 06417
–
4
1
1,152
10,890

Explore Nearby Homes

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Re/Max Valley Shore, Craig Milton

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.