Off Market Feb 2025 for $2.2M

$2,510,958

•

3,478

sq ft

39 Winthrop Rd, Deep River, CT 06417

About this home

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.

Single-familyProperty Type

1985Year Built

12.45 acresLot Size

$722Est. Price/Sq.Ft.

9 car garageParking

Listed by Craig Milton • Re/Max Valley Shore

Bought with Amber Bova • William Raveis Real Estate

Source:Smart MLS #24037674

Redfin Estimate

$2,510,958

$311K since sold in February 2025$286K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 192.4% higher than the average sale price ($859K) of 6 comparable homes.

SOLD JUN 25, 2026
$847,000
A
3 beds3.5 baths3,476 sq ft
74 Bushy Hill Rd, Ivoryton, CT 06442
SOLD AUG 7, 2026
$1,400,000
B
3 beds3.5 baths2,467 sq ft
45 Falls River Dr, Ivoryton, CT 06442
SOLD JUL 29, 2026
$730,000
C
3 beds2.5 baths2,848 sq ft
56 Shailer Pond Rd, Deep River, CT 06417
SOLD JUL 13, 2026
$750,000
D
3 beds3 baths2,231 sq ft
51 Witch Hazel Dr, Deep River, CT 06417
SOLD NOV 21, 2025
$650,000
E
3 beds2.5 baths3,354 sq ft
91 Main St, Ivoryton, CT 06442
SOLD APR 15, 2026
$775,000
F
3 beds4 baths2,611 sq ft
151 Bushy Hill Rd, Deep River, CT 06417

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$652,744

Est. take-home

List your home with Redfin and save $25,110

Market trends in 06417, CT

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

103.9%

+3.0% MoM

Median sale price

$435K

$2K MoM

Avg. days on market

32d

47 days MoM

Recently sold homes

4 MoM

New listings for sale

$329,900
2 beds1 bath1,015 sq ft
16 Jones Ln, Deep River, CT 06417
$684,900
4 beds2.5 baths2,126 sq ft
29 Union St, Deep River, CT 06417
$399,900
3 beds1 bath1,104 sq ft
49 Essex St, Deep River, CT 06417
OPEN SUN, 12PM TO 2PM
$635,000
4 beds2.5 baths2,196 sq ft
73 Long Hill Rd, Deep River, CT 06417
See all

Provided by Redfin

Sale history for 39 Winthrop Rd

Year

Property tax

Land + Additions

Assessment*

2023

$27,304 (+3.1%)

$146,440 + $767,340

$913,780

2022

$26,481 (−2.0%)

$146,440 + $767,340

$913,780

2021

$27,030 (−5.9%)

$146,440 + $767,340

$913,780

2020

$28,710 (+2.7%)

$183,260 + $774,060

$957,320

2019

$27,944

$183,260 + $766,570

$949,830

2018

$27,944 (+4.1%)

$183,260 + $766,570

$949,830

2017

$26,854 (+5.1%)

$174,930 + $753,620

$928,550

2016

$25,563

$174,930 + $753,620

$928,550

Tax history for 39 Winthrop Rd

Year

Property tax

Land + Additions

Assessment*

2023

$27,304 (+3.1%)

$146,440 + $767,340

$913,780

2022

$26,481 (−2.0%)

$146,440 + $767,340

$913,780

2021

$27,030 (−5.9%)

$146,440 + $767,340

$913,780

2020

$28,710 (+2.7%)

$183,260 + $774,060

$957,320

2019

$27,944

$183,260 + $766,570

$949,830

2018

$27,944 (+4.1%)

$183,260 + $766,570

$949,830

2017

$26,854 (+5.1%)

$174,930 + $753,620

$928,550

2016

$25,563

$174,930 + $753,620

$928,550

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

—

Baths

—

Stories

—

Lot width

—

Lot depth

—

Lot size

12.45 Acres

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Other

County

Middlesex County

APN

2644594

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Property details

Parking

Garage Information
Garage & Parking: Barn, Detached Garage, Paved, Driveway
Garages Number: 9

Parking Information
Parking Total Spaces: 9

Interior

Virtual Tour Information

Interior Information
Total Rooms: 9
Laundry Room Location: 2nd Floor
Laundry Room Info: Upper Level
In-Law Apartment: Yes
In-Law Access: Detached
Fireplaces Total: 5
Cooling System: Central Air
Appliances Included: Oven/Range, Refrigerator, Washer, Dryer, Wine Chiller

Bathroom Information
# of Baths (Full): 3
# of Baths (Half): 1

Bedroom Information
Beds Total: 3

Room Information
Rooms Additional: Exercise Room, Sauna, Sitting Room, Workshop
Basement Description: Full, Fully Finished

Exterior

Exterior Features
Roof Information: Asphalt Shingle, Fiberglass Shingle
Exterior Siding: Vinyl Siding
Exterior Features: Porch-Enclosed, Gazebo, Porch, Cabana, Patio

Lot Information
Lot Description: Water View

Pool Information
Swimming Pool
Pool Description: Heated, In Ground Pool

Building Information
Foundation Type: Concrete
Construction Description: Concrete
Color: Tan

Property Information
Waterfront Description: View
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 0
Driveway Type: Paved

Financial

Assessments Information
Assessed Value: $913,780

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Other
Heat Type: Hot Air
Heat Fuel Type: Propane
Fuel Tank Location: In Ground
Energy Features: Generator, Thermopane Windows

Location

School Information
High School: Per Board of Ed
Elementary School: Deep River

Location Information
State: Connecticut
Directions: GPS Friendly
County: Middlesex

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 12.45 acres
Style: Other
Year Built: —
Year Renovated: —
County: Middlesex County
APN: 2644594

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 12

Around this home

Schools

Deep River Elementary School

Public PreK-6 • Assigned • 1.9mi

7/10

John Winthrop Middle School

Public 7-8 • Assigned • 0.2mi

4/10

Valley Regional High School

Public 9-12 • Assigned • 0.7mi

7/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Historical weather

Deep River, CT • 06417

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

Try the sun simulator tool to see how light moves across the property at different times of day and year.

Provided by Shadowmap

Estimated sale price

$2.39M – $2.89M

Reach more buyers when you sell with Redfin. Save up to $25,110 in fees. 3 minutes to get started.

Get a free, detailed breakdown of how we calculated your estimate.

Nearby similar homes

$329,900

2 beds1 bath1,015 sq ft

16 Jones Ln, Deep River, CT 06417

3D WALKTHROUGH

$126,000

2 beds1 bath672 sq ft

5 Cook Ter, Westbrook, CT 06498

$625,000

4 beds3 baths2,560 sq ft

38 Main St, Deep River, CT 06417

$449,999

2 beds2 baths1,252 sq ft

46 Main St, Centerbrook, CT 06409

NEW CONSTRUCTION

$2,200,000

5 beds4.5 baths4,750 sq ft

Lot 2 - 160 Saybrook Rd, Essex, CT 06426

VIDEO TOUR

$1,295,000

4 beds4 baths4,937 sq ft

53 Oakridge Dr, Westbrook, CT 06498

New listings for sale in 06417

$329,900

2 beds1 bath1,015 sq ft

16 Jones Ln, Deep River, CT 06417

$684,900

4 beds2.5 baths2,126 sq ft

29 Union St, Deep River, CT 06417

$399,900

3 beds1 bath1,104 sq ft

49 Essex St, Deep River, CT 06417

OPEN SUN, 12PM TO 2PM

$635,000

4 beds2.5 baths2,196 sq ft

73 Long Hill Rd, Deep River, CT 06417

Home values near 39 Winthrop Rd

Data from public records.

Address	Redfin Estimate
21 Winthrop Rd, Deep River, CT 3 Beds \| 2 Baths \| 3344 Sq. Ft.	$1,014,866
27 Bahr Rd, Deep River, CT 4 Beds \| 1.5 Baths \| 1844 Sq. Ft.	$530,517

Address	Redfin Estimate
12 Winthrop Rd, Deep River, CT 4 Beds \| 1 Baths \| 1728 Sq. Ft.	$399,050
5 Warsaw St, Deep River, CT 2 Beds \| 2 Baths \| 1270 Sq. Ft.	$400,385

Address	Redfin Estimate
41 Winthrop Rd, Deep River, CT 3 Beds \| 2.5 Baths \| 3656 Sq. Ft.	$1,087,906
4 Bahr Rd, Deep River, CT 4 Beds \| 1.5 Baths \| 1744 Sq. Ft.	$518,877

Property information provided by Smart MLS when last listed in 2024. This data may not match . Learn more.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

Houses for rent in Middlesex County	Agents near me	Norwalk, CT homes for sale	Middlesex County Housing Market
Houses for sale near me	Greenwich, CT homes for sale	New Haven, CT homes for sale
Land for sale near me	Stamford, CT homes for sale	Milford, CT homes for sale
Open Houses near me	West Hartford, CT homes for sale	Middlesex County Property Records
Condos for sale near me	Westport, CT homes for sale	CT New Listings

Fairfield County homes for sale
Hartford County homes for sale
Suffolk County homes for sale

Clinton homes for sale
Meriden homes for sale
Middletown homes for sale

About this home

Redfin Estimate

Earn from this home

Market trends in 06417, CT

Sale history for 39 Winthrop Rd

Tax history for 39 Winthrop Rd

Public record

Property details

Around this home

Schools

Lifestyle

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06417

Home values near 39 Winthrop Rd

More real estate resources