Off market jan 2020 for $1.3M

$2,799,463

Est. refi paymentEst. refi $736/mo

•

4,089

sq ft

369 River Rd, Deep River, CT 06417

About this home

Perched directly on the banks of the Connecticut River, "Sunnyside" is a stunning Shingle style residence with wonderful contemporary flair, originally designed by Centerbrook Architects and recently renovated and expanded under the guidance of noted architect Stephen Lloyd. A meandering private drive leads to this exceptional waterfront estate, with beautiful lawns sloping gently to the waterside, incorporating a pool complex overlooking the protected boat basin and riverfront, as well as mature shade trees and lush gardens. Comfortable and versatile, the interior design offers an open floor plan featuring vaulted ceilings and rooms filled with natural light from walls of windows, all flowing to outdoor entertaining areas with stone terrace, boardwalks and custom decking. A newly designed first floor master suite with fireplace, commodious dressing room and sumptuous marble bath leads to the dramatic library with vaulted ceiling and custom cabinetry. And, if the main house isn't enough, the Boat House lies just beyond on the riverfront...with all the amenities for guests...including a two story Great Room, kitchen and bath and loft bedroom with views that cannot be described! Enjoy languid summer days of swimming, boating or just admiring the remarkable view from your own private retreat!

Please note there is a .13 acre strip of land incorporating the boat basin and owned under Moosehead Ventures Inc which is owned by James Scala. It is assessed at $80,080 and is included in the sale.

Single-familyProperty Type

1979Year Built

4.66 acresLot Size

$685Est. Price/Sq.Ft.

3 car garageParking

Listed by Jennifer Caulfield • William Pitt Sotheby's Int'l

Bought with Jennifer Caulfield • William Pitt Sotheby's Int'l

Source:Smart MLS #170231557

Redfin Estimate

$2,799,463

$1.4M since sold in January 2020$70K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 6.7% higher than the average sale price ($2.62M) of 6 comparable homes.

SOLD OCT 8, 2026
$3,650,000
A
5 beds4.5 baths4,769 sq ft
409 River Rd, Deep River, CT 06417
SOLD MAY 13, 2026
$1,825,000
B
4 beds3.5 baths5,362 sq ft
66 Cove Rd, Lyme, CT 06371
SOLD OCT 14, 2026
$845,000
C
4 beds2.5 baths2,756 sq ft
78 Meadow Woods Rd, Deep River, CT 06417
SOLD OCT 29, 2026
$4,872,480
D
4 beds4.5 baths5,459 sq ft
77 Joshua Ln, Lyme, CT 06371
SOLD SEP 11, 2026
$3,795,000
E
3 beds3.5 baths4,383 sq ft
7 Hanna Ln, Essex, CT 06426
SOLD APR 24, 2026
$750,000
F
4 beds4 baths2,800 sq ft
16 Navy Ln, Essex, CT 06426

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

Earn from this home

Sell

$1,703,689

Est. take-home

List your home with Redfin and save $27,995

Refinance

Est. cash available

Get cash now or lower your monthly rate

Market trends in 06417, CT

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

104.6%

2.2% MoM

Median sale price

$475K

$45K MoM

Avg. days on market

27d

14 days MoM

Recently sold homes

0 MoM

New listings for sale

$198,000
2 beds1 bath864 sq ft
77 Scenic View Dr #23, Deep River, CT 06417
$299,900
4 beds1 bath1,274 sq ft
147 River St, Deep River, CT 06417
$299,500
1 bed1.5 baths935 sq ft
92 Main St #410, Deep River, CT 06417
See all

Provided by Redfin

Sale history for 369 River Rd

Date

Event

Price

Public Records

Jan 13, 2020

Sold

$1,240,000

$303/sq ft

Public Records

Jan 13, 2020

Sold

$110,000

$27/sq ft

Smart MLS #170231557

Jan 10, 2020

Sold

$1,350,000

$330/sq ft

Oct 31, 2019

Pending

—

Sep 5, 2019

Listed

$1,500,000

$367/sq ft

Smart MLS #170028255

Nov 1, 2018

Listing Removed

—

Apr 2, 2018

Price Changed

$1,900,000

$465/sq ft

Nov 3, 2017

Listed

$2,490,000

$609/sq ft

Smart MLS #M9094126

Jun 30, 2006

Listing Removed

—

Feb 2, 2006

Listed

$2,850,000

$697/sq ft

Smart MLS #98249168

Dec 31, 2005

Listing Removed

—

Aug 16, 2005

Listed

$2,997,500

$733/sq ft

Smart MLS #98213460

Aug 1, 2005

Listing Removed

—

Sep 25, 2004

Listed

$2,797,500

$684/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$27,425 (+4.0%)

$570,850 + $346,990

$917,840

2022

$26,366 (−2.0%)

$570,850 + $338,940

$909,790

2021

$26,912 (−19.6%)

$570,850 + $338,940

$909,790

2020

$33,457 (+1.9%)

$690,270 + $425,320

$1,115,590

2019

$32,841

$690,270 + $426,020

$1,116,290

2018

$32,841 (+1.7%)

$690,270 + $426,020

$1,116,290

2017

$32,283 (+5.1%)

$690,270 + $426,020

$1,116,290

2016

$30,731 (−4.8%)

$690,270 + $426,020

$1,116,290

2014

$32,265 (+3.2%)

$760,830 + $485,870

$1,246,700

2011

$31,267

$760,830 + $485,870

$1,246,700

Tax history for 369 River Rd

Year

Property tax

Land + Additions

Assessment*

2023

$27,425 (+4.0%)

$570,850 + $346,990

$917,840

2022

$26,366 (−2.0%)

$570,850 + $338,940

$909,790

2021

$26,912 (−19.6%)

$570,850 + $338,940

$909,790

2020

$33,457 (+1.9%)

$690,270 + $425,320

$1,115,590

2019

$32,841

$690,270 + $426,020

$1,116,290

2018

$32,841 (+1.7%)

$690,270 + $426,020

$1,116,290

2017

$32,283 (+5.1%)

$690,270 + $426,020

$1,116,290

2016

$30,731 (−4.8%)

$690,270 + $426,020

$1,116,290

2014

$32,265 (+3.2%)

$760,830 + $485,870

$1,246,700

2011

$31,267

$760,830 + $485,870

$1,246,700

*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

4.66 Acres

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Other

County

Middlesex County

APN

962916

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Property details

Parking

Garage Information
Garage & Parking: Detached Garage
Garages Number: 3

Interior

Interior Information
Total Rooms: 9
Laundry Room Location: Main level
Laundry Room Info: Main Level
Interior Features: Auto Garage Door Opener, Cable - Pre-wired, Open Floor Plan, Security System
In-Law Apartment: Yes
In-Law Access: Detached
Fireplaces Total: 2
Cooling System: Central Air, Zoned
Appliances Included: Gas Cooktop, Wall Oven, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer

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

Bedroom Information
Beds Total: 4

Room Information
Rooms Additional: Foyer, Mud Room
Room Count: 9
Basement Description: Crawl Space, Concrete Floor, Sump Pump
Has Attic
Attic Description: Pull-Down Stairs, Floored, Storage Space

Exterior

Exterior Features
Roof Information: Wood Shingle
Exterior Siding: Shingle, Shake
Exterior Features: Barn, French Doors, Fruit Trees, Garden Area, Guest House, Lighting, Patio, Porch, Underground Sprinkler

Lot Information
Lot Description: Some Wetlands, Cleared, Secluded, Water View, Professionally Landscaped

Land Information
Encumbrances Restrictions: Inland-Wetland Restrictions

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

Building Information
Foundation Type: Concrete
Construction Description: Frame
Color: Gray

Property Information
Waterfront Description: Direct Waterfront, Frontage, River, Dock or Mooring
Property Type: Single Family For Sale
Driveway Type: Paved, Crushed Stone

Financial

Assessments Information
Assessed Value: $1,116,290

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Propane
Heat Type: Hydro Air, Zoned
Heat Fuel Type: Oil
Fuel Tank Location: Above Ground
Energy Features: Passive Solar, Generator, Thermopane Windows

Location

School Information
Middle Jr High School: Regional District 4
Intermediate School: Per Board of Ed
High School: Valley
Elementary School: Deep River

Location Information
State: Connecticut
Nearby Amenities: Commuter Bus, Golf Course, Health Club, Library, Medical Facilities, Shopping/Mall, Tennis Courts
Flood Zone
Directions: River Road to # 369 River Road. DO NOT GO DOWN DRIVEWAY WITHOUT APPOINTMENT!
Direct Waterfront
County: Middlesex

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 4.66 acres
Style: Other
Year Built: —
Year Renovated: —
County: Middlesex County
APN: 962916

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 5

Around this home

Schools

K - 12
Preschool & daycare

Deep River Elementary School

Public PreK-6 • Assigned • 2.2mi

7/10

John Winthrop Middle School

Public 7-8 • Assigned • 3.6mi

6/10

Valley Regional High School

Public 9-12 • Assigned • 3.1mi

7/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

10/10 Flood Factor

Estimated 80%+ chance of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

6/10 Heat Factor

7 days above 94° expected this year, 17 days in 30 years

8/10 Wind Factor

80% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

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

$2.66M – $3.22M

Reach more buyers when you sell with Redfin. Save up to $27,995 in fees. 3 minutes to get started.

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

Nearby similar homes

$499,900

4 beds3 baths2,148 sq ft

60 Town Woods Rd, Old Lyme, CT 06371

Finished lower level • Large yard • Secluded setting

VIDEO TOUR

$3,750,000

5 beds5.5 baths5,557 sq ft

323 River Rd, Deep River, CT 06417

Deep-water dock • Panoramic views • Natural light

$699,900

3 beds3 baths2,456 sq ft

45 Main St, Essex, CT 06426

Granite countertops • Hardwood floors • 1.61 acre lot

$1,150,000

3 beds4.5 baths3,308 sq ft

9 Ingham Hill Rd, Essex, CT 06426

Historic colonial • Sunny breakfast nook • Private living space

$3,495,000

6 beds5.5 baths5,806 sq ft

150 Joshuatown Rd, Lyme, CT 06371

Over 30 acres • Cathedral ceiling • Exposed cedar beams

$389,000

2 beds1.5 baths948 sq ft

28 Blake St, Ivoryton, CT 06442

Hardwood floors • Updated bathrooms • Back deck

New listings for sale in 06417

$198,000

2 beds1 bath864 sq ft

77 Scenic View Dr #23, Deep River, CT 06417

One floor living • Outdoor space • Private deck

$299,900

4 beds1 bath1,274 sq ft

147 River St, Deep River, CT 06417

First floor bedroom • Full bath • Generator hook up

$299,500

1 bed1.5 baths935 sq ft

92 Main St #410, Deep River, CT 06417

Remodeled kitchen • Renovated bathrooms • Hardwood flooring

Home values near 369 River Rd

Data from public records.

Address	Redfin Estimate
350 River Road, Deep River, CT 5 Beds \| 4.5 Baths \| 4551 Sq. Ft.	$1,780,801
409 River Road, Deep River, CT 5 Beds \| 4.5 Baths \| 4769 Sq. Ft.	$3,358,160
335 River Road, Deep River, CT 4 Beds \| 2.5 Baths \| 2104 Sq. Ft.	$1,002,883
381 River Road, Deep River, CT 5 Beds \| 4.5 Baths \| 5293 Sq. Ft.	$3,036,276
21 Brockway Ferry Road, Deep River, CT 3 Beds \| 3.5 Baths \| 3941 Sq. Ft.	$2,693,285
38 Brockway Ferry Road, Deep River, CT 4 Beds \| 3.5 Baths \| 4900 Sq. Ft.	$3,175,958
7 Winterberry Road, Deep River, CT 4 Beds \| 4.5 Baths \| 5205 Sq. Ft.	$2,163,281

Address	Redfin Estimate
414 River Road, Deep River, CT 4 Beds \| 6.5 Baths \| 4684 Sq. Ft.	$1,264,576
391 River Road, Deep River, CT 3 Beds \| 3 Baths \| 2443 Sq. Ft.	$1,772,340
349 River Road, Deep River, CT 4 Beds \| 3.5 Baths \| 2816 Sq. Ft.	$1,121,937
16 Brockway Ferry Road, Deep River, CT 2 Beds \| 3 Baths \| 3294 Sq. Ft.	$1,338,431
1 Brockway Ferry Road, Deep River, CT 3 Beds \| 4.5 Baths \| 4322 Sq. Ft.	$1,419,018
28 Winterberry Road, Deep River, CT 4 Beds \| 4.5 Baths \| 5443 Sq. Ft.	$1,478,999
49 Winterberry Road, Deep River, CT 4 Beds \| 6 Baths \| 7042 Sq. Ft.	$1,661,188

Address	Redfin Estimate
401 River Road, Deep River, CT 2 Beds \| 3.5 Baths \| 3994 Sq. Ft.	$1,948,177
357 River Road, Deep River, CT 4 Beds \| 4.5 Baths \| 3907 Sq. Ft.	$3,697,367
357 River Road #A, Deep River, CT 2 Beds \| 2 Baths \| 1295 Sq. Ft.	$1,180,976
15 Brockway Ferry Road, Deep River, CT 4 Beds \| 4 Baths \| 6537 Sq. Ft.	$2,657,899
25 Brockway Ferry Road, Deep River, CT 4 Beds \| 5 Baths \| 8092 Sq. Ft.	$3,445,511
17 Winterberry Road, Deep River, CT 4 Beds \| 5 Baths \| 5162 Sq. Ft.	$1,444,598
35 Winterberry Road, Deep River, CT 4 Beds \| 5 Baths \| 6061 Sq. Ft.	$2,430,063

Property information provided by Smart MLS when last listed in 2019. 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.

Redfin Brokerage Licenses

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	Westport, 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	Norwalk, CT homes for sale	CT New Listings

Fairfield County homes for sale
Suffolk County homes for sale
New Haven 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 369 River Rd

Tax history for 369 River Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06417

Home values near 369 River Rd

More real estate resources