Is Deep River Center, Deep River, CT dog-friendly?

As of early 2026, 100% of users say it's dog friendly

Is there wildlife in Deep River Center, Deep River, CT?

As of early 2026, 94% of users say there's wildlife

Is a car needed in Deep River Center, Deep River, CT?

As of early 2026, 94% of users say car is needed

Is Deep River Center, Deep River, CT walkable to grocery stores?

As of early 2026, 86% of users say it's walkable to grocery stores

Are yards well-kept in Deep River Center, Deep River, CT?

As of early 2026, 85% of users say yards are well-kept

Is Deep River Center, Deep River, CT walkable to restaurants?

As of early 2026, 84% of users say it's walkable to restaurants

Are the streets well-lit in Deep River Center, Deep River, CT?

As of early 2026, 82% of users say streets are well-lit

Is parking easy in Deep River Center, Deep River, CT?

As of early 2026, 80% of users say parking is easy

Do kids play outside in Deep River Center, Deep River, CT?

As of early 2026, 76% of users say kids play outside

Would people walk alone at night in Deep River Center, Deep River, CT?

As of early 2026, 75% of users say people would walk alone at night

Does Deep River Center, Deep River, CT show holiday spirit?

As of early 2026, 75% of users say there's holiday spirit

Does Deep River Center, Deep River, CT have sidewalks?

As of early 2026, 73% of users say there are sidewalks

Are neighbors friendly in Deep River Center, Deep River, CT?

As of early 2026, 72% of users say neighbors are friendly

Do residents of Deep River Center, Deep River, CT plan to stay at least 5 years?

As of early 2026, 60% of users say they plan to stay for at least 5 years

Are there community events in Deep River Center, Deep River, CT?

As of early 2026, 42% of users say there are community events

Is Deep River Center, Deep River, CT quiet?

As of early 2026, 36% of users say it's quiet

OFF MARKET

27 High St
Deep River, CT 06417

Deep River Center

3 Beds
1.5 Baths
1,416 sqft

$417,800

Trulia Estimate

as of Jul 30, 2026

Est. Refi. Payment $2,885/mo*

Refinance Your Home

$417,800

Trulia Estimate

as of Jul 30, 2026

Est. Refi. Payment $2,885/mo*

Refinance Your Home

3 Beds

1.5 Baths

1,416 sqft

Local Information

Map ViewExplore the area around 27 High St.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1840

Living Area

1,416 sqft

Price/Sqft

$295

About this House

Location, Location, Location a short stroll to downtown to enjoy the parades, shopping, and restaurants. This home offers 3 bedrooms, 1 full bathroom on the 2nd floor and one-half on the first floor. Living room with bookshelves, formal dining room, wood floors, large kitchen perfect, with small fenced yard to enjoy family gatherings! Enjoy the front porch with your favorite book!

27 High St, Deep River, CT 06417 is a 3 bedroom, 2 bathroom, 1,416 sqft single-family home in Deep River Center, built in 1840. It last sold for $240,000 on Aug 25, 2020. It is currently off market. The Trulia Estimate is $417,800, with a rent estimate of $2,786/month.

Home Details for 27 High St

Interior Features
Interior Details BasementAtticNumber of Rooms: 6
Heating & Cooling Heating: Other, OtherHeating Fuel: Other
Levels, Entrance, & Accessibility Stories: 2Floors: Other

Exterior Features
Exterior Home Features Roof: OtherDeckExterior: Other

Property Information
Year Built Year Built: 1840
Property Type / Style Property Type: Single Family HomeArchitecture: Old Style

Community
Units in Building: 1

Lot Information
Lot Area: 5662 sqft

Price History for 27 High St

Date	Price	Event	Source
08/26/2020	$230,000	ListingRemoved	Agent Provided

08/26/2020	$230,000	Listed For Sale	Agent Provided

08/25/2020	$240,000	Sold	Smart MLS #170311362
Recording Date 08/25/2020 County Transfer Tax N/A Total Transfer Tax N/A
07/14/2020	$230,000	Pending	Agent Provided

07/01/2020	$230,000	Listed For Sale	Agent Provided

05/19/2011	$210,000	Sold	Smart MLS #M9127672
Recording Date 05/19/2011 County Transfer Tax N/A Total Transfer Tax N/A
05/01/2011	$206,427	Pending	Agent Provided

04/20/2011	$206,427	PriceChange	Agent Provided
Price Change $206,427 (0%)
04/16/2011	$0	Listed For Sale	Agent Provided

01/03/2010	$254,900	ListingRemoved	Agent Provided

08/18/2009	$254,900	PriceChange	Agent Provided
Price Change $4,100 (-2%)
07/18/2009	$259,000	PriceChange	Agent Provided
Price Change $15,900 (-6%)
03/01/2009	$274,900	PriceChange	Agent Provided
Price Change $99 (-0%)
01/24/2009	$274,999	PriceChange	Agent Provided
Price Change $10,000 (-4%)
10/24/2008	$284,999	PriceChange	Agent Provided
Price Change $14,901 (-5%)
10/16/2008	$299,900	PriceChange	Agent Provided
Price Change $20,000 (-6%)
08/23/2008	$319,900	Listed For Sale	Agent Provided

08/29/2003	$220,000	Sold	Smart MLS #M9073416
Recording Date 08/29/2003 County Transfer Tax N/A Total Transfer Tax N/A
09/30/1999	$155,500	Sold	N/A
Recording Date 09/30/1999 County Transfer Tax N/A Total Transfer Tax N/A
01/18/1991	$157,000	Sold	N/A
Recording Date 01/18/1991 County Transfer Tax N/A Total Transfer Tax N/A

Market trends in Deep River

Last updated June 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

7MoM

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Property Tax and Assessment

Year	2025
Tax	$5,440
Assessment	$170,100

Home facts updated by county records

Comparable Sales for 27 High St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
15 Prospect Street, Deep River, CT	0.11	Single-Family Home	$393,000	11/21/25	3	2	1,352
69 High Street, Deep River, CT	0.20	Single-Family Home	$407,000	11/24/25	2	1.5	1,440
152 Union Street, Deep River, CT	0.51	Single-Family Home	$379,000	11/26/25	3	1	1,144
2 Crescent Street, Deep River, CT	0.21	Single-Family Home	$421,000	12/19/25	4	1.5	1,878
111 Union St, Deep River, CT	0.44	Single-Family Home	$275,000	12/02/25	2	2	1,172
8 Prospect Hill, Deep River, CT	0.19	Single-Family Home	$345,000	07/24/26	2	1	912
15 Grove Street, Deep River, CT	0.35	Single-Family Home	$415,000	07/24/26	4	1.5	1,080
5 Mitchell Lane, Deep River, CT	0.63	Single-Family Home	$366,000	12/29/25	2	1.5	1,081
12 Jones Lane, Deep River, CT	0.50	Single-Family Home	$430,000	06/29/26	2	1	1,200
25 Union Street, Deep River, CT	0.48	Single-Family Home	$426,000	04/16/26	3	1.5	2,012

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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OFF MARKET
Est. $358,600
2 bd
1 ba
1,129 sqft
42 River Street,
Deep River, CT 06417
Coldwell Banker Realty
OFF MARKET
Est. $283,500
5 bd
1 ba
2,330 sqft
3 Old River Street,
Deep River, CT 06417
Compass Connecticut, LLC
SOLD
NOV 21, 2025
$393,000
3 bd
2 ba
1,352 sqft
15 Prospect Street,
Deep River, CT 06417
Re/Max Valley Shore
OFF MARKET
Est. $404,800
3 bd
2 ba
1,619 sqft
17 River Street,
Deep River, CT 06417
Chiarito Real Estate LLC
OFF MARKET
Est. $473,800
4 bd
2 ba
1,675 sqft
40 High Street,
Deep River, CT 06417
Re/Max Valley Shore
OFF MARKET
Est. $349,900
2 bd
1 ba
1,080 sqft
22 Prospect Street,
Deep River, CT 06417
Coldwell Banker Realty
OFF MARKET
Est. $563,200
3 bd
2.5 ba
1,920 sqft
8 Read Street,
Deep River, CT 06417
William Raveis Real Estate
OFF MARKET
Est. $525,600
3 bd
2 ba
1,596 sqft
58 River Street,
Deep River, CT 06417
Re/Max Valley Shore
SOLD
MAY 19, 2026
$625,000
4 bd
2 ba
1,970 sqft
62 River Street,
Deep River, CT 06417
Houlihan Lawrence WD
SOLD
JUL 24, 2026
$345,000
2 bd
1 ba
912 sqft
8 Prospect Hill,
Deep River, CT 06417
Berkshire Hathaway NE Prop.
OFF MARKET
Est. $430,000
3 bd
2 ba
1,456 sqft
119 Main Street,
Deep River, CT 06417
Homes Plus of Connecticut
FOR SALE
$825,000
6 bd
3 ba
4,184 sqft
163-165 Main Street,
Deep River, CT 06417
VC Property Group, LLC

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Additional Cost

Assigned Schools

These are the assigned schools for 27 High St.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Deep River Center

14 Homes For You
Buy: $205k - $1.2m

See Local Highlights

Neighborhood stats provided by third party data sources.

What Locals Say about Deep River Center

At least 10 Trulia users voted on each feature.

100 % Say it's dog friendly
94 % Say there's wildlife
94 % Say car is needed
86 % Say it's walkable to grocery stores
85 % Say yards are well-kept
84 % Say it's walkable to restaurants
82 % Say streets are well-lit
80 % Say parking is easy
76 % Say kids play outside
75 % Say people would walk alone at night
75 % Say there's holiday spirit
73 % Say there are sidewalks
72 % Say neighbors are friendly
60 % Say they plan to stay for at least 5 years
42 % Say there are community events
36 % Say it's quiet

Sourced by Trulia users. Learn more about our methodology.

Timothy Ballantyne
Resident
1y ago
"Friendly helpful neighbors community support for different kinds of groups volunteer firefighters and ambulance "
0
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Dave M.
Resident
7y ago
"the deep river muster, all my friends and family, great community!! deep river day in September. Small town America in New England!!"
4
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LGBTQ Local Legal Protections

Apartments for Rent

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$1,390/mo
Fees may apply
1 bd
1 ba
160 Main St #11019781,
Deep River, CT 06417
Contact for price
1-2 bd
1-2 ba
3 S Wig Hill Rd #f320a52c6,
Chester, CT 06412
Contact for price
1-2 bd
1-2 ba
132 Main St #f320a52c6,
Chester, CT 06412
Contact for price
1-2 bd
1-2 ba
10 Prospect St #f320a52c6,
Deep River, CT 06417
Contact for price
1-2 bd
1-2 ba
63 Westbrook Rd #776f18ccb,
Centerbrook, CT 06409
NEW - 2 DAYS AGO
APPLY INSTANTLY
$2,000/mo
Total price
2 bd
1 ba
165 Main St #A,
Ivoryton, CT 06442
APPLY INSTANTLY
$2,000/mo
Total price
2 bd
1 ba
Address Not Disclosed,
Deep River, CT 06417
APPLY INSTANTLY
$10,000/mo
Total price
3 bd
3.5 ba
150 Ferry Rd #THE,
Old Lyme, CT 06371
PET FRIENDLY
$1,700/mo
Total price
1 bd
1 ba
26 Sunset Ter #C,
Essex, CT 06426
$2,750/mo
Fees may apply
1 bd
1 ba
107 W Main St #1-B,
Chester, CT 06412
See more homes for rent in
Deep River
Take a look

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Homes for sale near 27 High St

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0.52 ACRES
$399,900
2 bd
1 ba
1,817 sqft
79 River Street,
Deep River, CT 06417
Compass Connecticut, LLC
COMING SOON 7/31
0.58 ACRES
$325,000
2 bd
1.5 ba
1,061 sqft
17&21 Winter Avenue,
Deep River, CT 06417
Re/Max Valley Shore
NEW
OPEN SAT, 3-5PM
COMING SOON 8/1
0.61 ACRES
$259,000
3 bd
3 ba
1,836 sqft
72 Winter Avenue,
Deep River, CT 06417
Coldwell Banker Realty
1.47 ACRES
$650,000
4 bd
3 ba
2,560 sqft
38 Main Street,
Deep River, CT 06417
RE/MAX on the Bay
0.45 ACRES
$1,199,999
9 bd
9 ba
4,982 sqft
209 Main Street,
Deep River, CT 06417
William Pitt Sotheby's Int'l
$489,999
3 bd
2 ba
1,608 sqft
89 Book Hill Road,
Essex, CT 06426
RE/MAX RISE
0.27 ACRES
$299,900
3 bd
1 ba
1,217 sqft
92 Water Street,
Chester, CT 06412
SSG Real Estate LLC
$400,000
3 bd
2.5 ba
1,572 sqft
93 Book Hill Road,
Essex, CT 06426
Innovation Propeties, LLC
3.9 ACRES
$924,000
4 bd
2.5 ba
2,774 sqft
15 Pent Road,
Deep River, CT 06417
Ki Property Group
0.68 ACRES
$499,000
3 bd
2 ba
1,188 sqft
135 Middlesex Avenue,
Chester, CT 06412
Re/Max Valley Shore
See more homes for sale in
Deep River
Take a look

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Off Market Homes Near 27 High St

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SOLD
JUL 28, 2026
$245,000
2 bd
1.5 ba
1,080 sqft
391 Main Street #308,
Deep River, CT 06417
Team Jermainne Real Estate Services, LLC
SOLD
JUL 27, 2026
$515,000
3 bd
3 ba
2,971 sqft
12 Meadow Lane,
Chester, CT 06412
Puorro Realty Group
SOLD
JUL 24, 2026
$345,000
2 bd
1 ba
912 sqft
8 Prospect Hill,
Deep River, CT 06417
Berkshire Hathaway NE Prop.
SOLD
JUL 24, 2026
$415,000
4 bd
1.5 ba
1,080 sqft
15 Grove Street,
Deep River, CT 06417
William Raveis Real Estate
SOLD
JUL 24, 2026
$625,000
4 bd
2.5 ba
2,550 sqft
22 Ebony Lane,
Ivoryton, CT 06442
Compass Connecticut, LLC
SOLD
JUL 23, 2026
$233,600
2 bd
2 ba
1,344 sqft
3 KIRTLAND Avenue,
Chester, CT 06412
Realhome Services & Solutions
SOLD
JUL 21, 2026
$331,500
2 bd
1 ba
912 sqft
8 Phelps Lane,
Deep River, CT 06417
Real Broker CT, LLC
SOLD
JUL 21, 2026
$580,000
3 bd
2 ba
1,880 sqft
7 Mitchel Terrace,
Ivoryton, CT 06442
Re/Max Valley Shore
SOLD
JUL 17, 2026
$371,500
2 bd
1 ba
806 sqft
19 Blake Street,
Ivoryton, CT 06442
Berkshire Hathaway NE Prop.
SOLD
JUL 14, 2026
$616,000
2 bd
2.5 ba
1,726 sqft
16 Sypher Road,
Chester, CT 06412
Coldwell Banker Realty
See more homes for sale in
Deep River
Take a look

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27 High St
Deep River, CT 06417

$417,800

$417,800