Is Essex, CT dog-friendly?

As of early 2026, 97% of users say it's dog friendly

Are yards well-kept in Essex, CT?

As of early 2026, 89% of users say yards are well-kept

Is a car needed in Essex, CT?

As of early 2026, 88% of users say car is needed

Does Essex, CT show holiday spirit?

As of early 2026, 88% of users say there's holiday spirit

Are neighbors friendly in Essex, CT?

As of early 2026, 80% of users say neighbors are friendly

Is parking easy in Essex, CT?

As of early 2026, 78% of users say parking is easy

Would people walk alone at night in Essex, CT?

As of early 2026, 77% of users say people would walk alone at night

Do residents of Essex, CT plan to stay at least 5 years?

As of early 2026, 76% of users say they plan to stay for at least 5 years

Is Essex, CT walkable to restaurants?

As of early 2026, 75% of users say it's walkable to restaurants

Is there wildlife in Essex, CT?

As of early 2026, 71% of users say there's wildlife

As of early 2026, 70% of users say it's quiet

Are the streets well-lit in Essex, CT?

As of early 2026, 62% of users say streets are well-lit

Does Essex, CT have sidewalks?

As of early 2026, 61% of users say there are sidewalks

Do kids play outside in Essex, CT?

As of early 2026, 50% of users say kids play outside

Are there community events in Essex, CT?

As of early 2026, 50% of users say there are community events

Is Essex, CT walkable to grocery stores?

As of early 2026, 16% of users say it's walkable to grocery stores

OFF MARKET

27 Old Deep River Rd
Centerbrook, CT 06409

3 Beds
1.5 Baths
1,383 sqft (on 0.69 acres)

$562,400

Trulia Estimate

as of May 30, 2026

Est. Refi. Payment $3,770/mo*

Refinance Your Home

$562,400

Trulia Estimate

as of May 30, 2026

Est. Refi. Payment $3,770/mo*

Refinance Your Home

3 Beds

1.5 Baths

1,383 sqft

(on 0.69 acres)

Local Information

-- mins to

Commute Destination

Description

Picture perfect antique farmhouse completely updated including central air conditioning. Gorgeous newer kitchen with sparkling granite counters, large sink with window above it to enjoy the views of the private yard. Open concept kitchen/dining room and living room are bright and sunny. Powder room on the first floor, pub room, laundry and storage in the partially finished basement. Three bedrooms and full bath on second floor along with bonus finished attic space for office/den. Fabulous 3 bay historic barn/garage. Brand new oversized wood patio for outdoor entertaining. Large level yard surrounded by mature trees offering privacy and yet extremely convenient to shopping, marinas, restaurants, art galleries and everything the three villages of Essex offers.

This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking

Garage

Outdoor

Deck

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

No Info

Home Details for 27 Old Deep River Rd

Interior Features
Interior Details BasementAtticNumber of Rooms: 6
Heating & Cooling Heating: Oil, OtherAir ConditioningCooling System: CentralHeating Fuel: Oil
Levels, Entrance, & Accessibility Stories: 2Floors: Hardwood
Appliances & Utilities Cable ReadyDishwasherDisposalDryerRefrigeratorWasher

Exterior Features
Exterior Home Features Roof: Asphalt, OtherDeckExterior: Other, WoodGardenLawn
Parking & Garage GarageParking: Garage Detached

Property Information
Year Built Year Built: 1890
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 0.69 acres

Price History for 27 Old Deep River Rd

Date	Price	Event	Source
11/10/2020	$397,000	Sold	Smart MLS #170328150
Recording Date 11/10/2020 County Transfer Tax N/A Total Transfer Tax N/A
10/14/2020	$409,900	Pending	Agent Provided

09/22/2020	$409,900	PriceChange	Agent Provided
Price Change $10,000 (-2%)
08/27/2020	$419,900	Listed For Sale	Agent Provided

09/11/2015	$335,000	Sold	Smart MLS #N10066227
Recording Date 09/11/2015 County Transfer Tax N/A Total Transfer Tax N/A
02/24/2014	$317,500	Sold	Smart MLS #M9145033
Recording Date 02/24/2014 County Transfer Tax N/A Total Transfer Tax N/A
02/11/2004	$220,000	Sold	N/A
Recording Date 02/11/2004 County Transfer Tax N/A Total Transfer Tax N/A
05/15/2001	$168,000	Sold	N/A
Recording Date 05/15/2001 County Transfer Tax N/A Total Transfer Tax N/A
09/20/1991	$150,000	Sold	N/A
Recording Date 09/20/1991 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2025
Tax	$4,004
Assessment	$214,900

Home facts updated by county records

Comparable Sales for 27 Old Deep River Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
3 Donald Rd Extension, Essex, CT	0.61	Single-Family Home	$580,000	04/17/26	3	1.5	1,510
17 Charles Street, Centerbrook, CT	0.69	Single-Family Home	$415,000	04/23/26	3	2	960
15 Cedar Street, Centerbrook, CT	0.69	Single-Family Home	$455,000	12/22/25	3	2	1,934
126 Main Street, Centerbrook, CT	0.67	Single-Family Home	$850,000	12/02/25	3	2.5	1,863
41 Woodland Drive, Centerbrook, CT	1.00	Single-Family Home	$498,000	07/30/25	3	1.5	1,742
7 Earl Street, Centerbrook, CT	0.68	Single-Family Home	$185,000	12/02/25	3	1	1,060
7 Dogwood Drive, Centerbrook, CT	0.90	Single-Family Home	$430,000	08/26/25	4	1.5	1,750
32 Sunset Ter, Essex, CT	0.96	Single-Family Home	$450,000	03/31/26	3	2	1,370
19 West Hills Road, Ivoryton, CT	0.80	Single-Family Home	$605,000	09/22/25	3	2.5	2,648
6 Birch Circle, Centerbrook, CT	1.16	Single-Family Home	$370,000	10/27/25	3	1.5	1,670

Nearby homes

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

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FOR SALE
0.74 ACRES
$829,000
4 bd
4 ba
7,309 sqft
33 Deep River Road,
Centerbrook, CT 06409
William Pitt Sotheby's Int'l
OFF MARKET
Est. $651,000
3 bd
2.5 ba
2,208 sqft
22 Eagle Ridge Drive,
Essex, CT 06426
Coldwell Banker Realty
OFF MARKET
Est. $714,200
4 bd
2.5 ba
2,080 sqft
27 Eagle Ridge Drive,
Essex, CT 06426
Coldwell Banker Realty
OFF MARKET
Est. $1,141,200
4 bd
2.5 ba
2,801 sqft
77 Main Street,
Essex, CT 06426
Seabury Hill REALTORS
OFF MARKET
Est. $733,900
3 bd
2.5 ba
1,931 sqft
85 Main Street,
Essex, CT 06426
Century 21 AllPoints Realty
OFF MARKET
Est. $803,600
3 bd
2.5 ba
2,848 sqft
77 Dennison Road,
Essex, CT 06426
Higgins Group Real Estate
OFF MARKET
Est. $777,300
3 bd
4.5 ba
2,250 sqft
0 Lot 10 Eagle Ridge,
Essex, CT 06426
William Raveis Real Estate
FOR SALE
NEW
OPEN SAT, 1-3PM
0.48 ACRES
$769,900
3 bd
3 ba
2,400 sqft
112 Main Street,
Centerbrook, CT 06409
Century 21 Classic Homes
OFF MARKET
Est. $402,600
3 bd
2 ba
1,996 sqft
36 Westbrook Road,
Centerbrook, CT 06409
William Raveis Real Estate
OFF MARKET
Est. $632,300
3 bd
2.5 ba
2,337 sqft
7 Cedar Street,
Centerbrook, CT 06409
Coldwell Banker Realty
SOLD
APR 17, 2026
$580,000
3 bd
1.5 ba
1,510 sqft
3 Donald Rd Extension,
Essex, CT 06426
William Raveis Real Estate

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Additional Cost

Assigned Schools

These are the assigned schools for 27 Old Deep River Rd.

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.

What Locals Say about Essex

At least 26 Trulia users voted on each feature.

97 % Say it's dog friendly
89 % Say yards are well-kept
88 % Say car is needed
88 % Say there's holiday spirit
80 % Say neighbors are friendly
78 % Say parking is easy
77 % Say people would walk alone at night
76 % Say they plan to stay for at least 5 years
75 % Say it's walkable to restaurants
71 % Say there's wildlife
70 % Say it's quiet
62 % Say streets are well-lit
61 % Say there are sidewalks
50 % Say kids play outside
50 % Say there are community events
16 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.

Trulia User
Resident
2y ago
"Adult community. People younger than 55 not allowed. So children falls into that. Sorry but that is the rule. "
0
Flag
Bersingj
Resident
7y ago
"Quiet, relaxed. A lot of money in this area! Schools are great, and there are many shops and great places to eat. Plus Essex steam train and Ivoryton play house!! Just very expensive to live here!!!! "
3
Flag
Jennyw7669
Resident
7y ago
"I’m very close to major highways and local shopping (grocery store ) are easy to get to. We’re happy with the are"
0
Flag
Jennyw7669
Resident
7y ago
"Essex is a great community, with wonderful schools and activities. Fun town events to look forward to throughout the year. Essex’s has such deep history, so much to learn about this town. "
0
Flag
Salbert13
11y ago
"The Essex area including Ivoryton and centerbrook is very unique and charming. The Essex steam train whistle brings you back to the past. The downtown centers of each village provides local art shops and local cuisine. The overall location to other major shopping areas is very convenient. Lastly, the schools are listed as top performing schools. "
0
Flag
Keith B.
11y ago
"Ivoryton (Essex) area has many land bank plus Nature Conservancy areas open to the public. We have 10 marinas within 5 miles with access to LIS and CT River. There are 2 outlet malls within 8 miles, a 12 theater cinema within 5 miles, 4 grocery stores within 10 miles, live local theater. Amtrak and commuter rail within 10 miles. Access to I-95 five miles away. Clean, quiet small community."
0
Flag
Louisa K.
12y ago
"I grew up in the next town and went to the public schools. Returned to Essex 23 years ago, and my children attended the public schools. The town has lovely parks, hiking trails, shops, restaurants and terrific neighborhoods. Water access for kayaks and boating is abundant. Local tourist sites include Essex Steam Train, Ivoryton Playhouse, CT River Museum and the Griswold Inn."
4
Flag

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
10 Prospect St #f320a52c6,
Deep River, CT 06417
Contact for price
1-2 bd
1-2 ba
30 Bokum Rd #f320a52c6,
Essex, CT 06426
Contact for price
1-2 bd
1-2 ba
63 Westbrook Rd #776f18ccb,
Centerbrook, CT 06409
Contact for price
1-2 bd
1-2 ba
59 S Main St #f320a52c6,
Essex, CT 06426
Contact for price
1-2 bd
1-2 ba
27 Plains Rd #776f18ccb,
Essex, CT 06426
$2,400/mo
Total price
1 bd
1 ba
95R Saybrook Rd #95,
Essex, CT 06426
$2,000/mo
Total price
2 bd
1 ba
26 Sunset Ter #B2,
Essex, CT 06426
See more homes for rent in
Centerbrook
Take a look

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Explore by feature

$2,400/mo
Total price
1 bd
1 ba
1,140 sqft
95R Saybrook Rd #95,
Essex, CT 06426
$2,000/mo
Total price
2 bd
1 ba
700 sqft
26 Sunset Ter #B2,
Essex, CT 06426
NEW - 1 DAY AGO
1.58 ACRES
$3,200/mo
Fees may apply
3 bd
2.5 ba
1,750 sqft
31 Deer Ln,
Ivoryton, CT 06442
NEW - 1 DAY AGO
FURNISHED
$3,900/mo
Fees may apply
3 bd
2 ba
2,176 sqft
32 West Ave,
Essex, CT 06426
PET FRIENDLY
FURNISHED
$9,000/mo
Fees may apply
3 bd
3.5 ba
3,078 sqft
29 New City St,
Essex, CT 06426
$1,900/mo
Fees may apply
2 bd
1 ba
950 sqft
70 Pond Meadow Rd,
Ivoryton, CT 06442
6 rentals with air conditioning in Centerbrook, CT

Homes for sale near 27 Old Deep River Rd

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NEW
OPEN SAT, 1-3PM
0.48 ACRES
$769,900
3 bd
3 ba
2,400 sqft
112 Main Street,
Centerbrook, CT 06409
Century 21 Classic Homes
NEW
OPEN SAT, 11-2PM
0.61 ACRES
$439,900
4 bd
2 ba
1,884 sqft
16 Main Street,
Essex, CT 06426
William Pitt Sotheby's Int'l
1.37 ACRES
$584,400
3 bd
2 ba
1,880 sqft
7 Mitchel Terrace,
Ivoryton, CT 06442
Re/Max Valley Shore
1.26 ACRES
$1,250,000
3 bd
3.5 ba
2,467 sqft
45 Falls River Drive,
Essex, CT 06426
William Raveis Real Estate
0.84 ACRES
$899,000
3 bd
3 ba
2,515 sqft
16 Parker Terrace,
Essex, CT 06426
William Pitt Sotheby's Int'l
0.74 ACRES
$1,595,000
3 bd
2.5 ba
2,708 sqft
46 West Avenue,
Essex, CT 06426
Wollman Realty
1.61 ACRES
$759,900
3 bd
3 ba
2,456 sqft
45 Main Street,
Essex, CT 06426
William Pitt Sotheby's Int'l
$450,000
3 bd
2.5 ba
1,572 sqft
93 Book Hill Road,
Essex, CT 06426
Innovation Propeties, LLC
0.84 ACRES
$1,795,000
4 bd
3.5 ba
3,724 sqft
101 North Main Street,
Essex, CT 06426
William Pitt Sotheby's Int'l
NEW
COMING SOON 6/4
2 ACRES
$1,125,000
3 bd
3 ba
1,905 sqft
49 River Road,
Essex, CT 06426
William Pitt Sotheby's Int'l
See more homes for sale in
Centerbrook
Take a look

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Off Market Homes Near 27 Old Deep River Rd

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SOLD
MAY 28, 2026
$600,000
4 bd
3 ba
2,062 sqft
5 Rosewood Lane,
Ivoryton, CT 06442
Compass Connecticut, LLC
SOLD
MAY 21, 2026
$800,000
4 bd
2.5 ba
2,896 sqft
185 Ingham Hill Road,
Old Saybrook, CT 06475
Compass Connecticut, LLC
SOLD
MAY 21, 2026
$441,000
3 bd
1.5 ba
2,283 sqft
120 Warsaw Street,
Deep River, CT 06417
Coldwell Banker Realty
SOLD
MAY 19, 2026
$625,000
4 bd
2 ba
1,970 sqft
62 River Street,
Deep River, CT 06417
Houlihan Lawrence WD
SOLD
MAY 14, 2026
$735,000
3 bd
2.5 ba
2,218 sqft
1 Verona Street,
Ivoryton, CT 06442
William Pitt Sotheby's Int'l
SOLD
MAY 14, 2026
$456,850
4 bd
2.5 ba
1,777 sqft
22 Summit Street,
Ivoryton, CT 06442
RE/MAX Alliance
SOLD
MAY 12, 2026
$610,000
3 bd
2.5 ba
1,887 sqft
57 Witch Hazel Drive,
Deep River, CT 06417
Waterhouse Realty LLC
SOLD
MAY 8, 2026
$560,000
3 bd
2 ba
1,398 sqft
167 Ingham Hill Road,
Old Saybrook, CT 06475
William Raveis Real Estate
SOLD
MAY 8, 2026
$500,000
2 bd
1 ba
1,040 sqft
9 2nd Avenue,
Old Saybrook, CT 06475
Coldwell Banker Realty
SOLD
MAY 1, 2026
$635,000
4 bd
3 ba
2,242 sqft
1 Ferry Rd,
Chester, CT 06412
See more homes for sale in
Centerbrook
Take a look

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Homes for rent near 27 Old Deep River Rd

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$3,600/mo
Total price
3 bd
2.5 ba
2,095 sqft
131 Hemlock Dr,
Deep River, CT 06417
NEW - 1 DAY AGO
1.58 ACRES
$3,200/mo
Fees may apply
3 bd
2.5 ba
1,750 sqft
31 Deer Ln,
Ivoryton, CT 06442
NEW - 1 DAY AGO
FURNISHED
$3,900/mo
Fees may apply
3 bd
2 ba
2,176 sqft
32 West Ave,
Essex, CT 06426
PET FRIENDLY
FURNISHED
$9,000/mo
Fees may apply
3 bd
3.5 ba
3,078 sqft
29 New City St,
Essex, CT 06426
1.2 ACRES
$3,500/mo
Fees may apply
3 bd
2 ba
2,946 sqft
958 Middlesex Tpke,
Old Saybrook, CT 06475
$2,500/mo
Fees may apply
2 bd
1 ba
1,250 sqft
3A Main St,
Essex, CT 06426
See more homes for rent in
Centerbrook
Take a look

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27 Old Deep River Rd, Centerbrook, CT 06409 is a 3 bedroom, 2 bathroom, 1,383 sqft single-family home built in 1890. This property is not currently available for sale. 27 Old Deep River Rd was last sold on Nov 10, 2020 for $397,000. The current Trulia Estimate for 27 Old Deep River Rd is $562,400.

27 Old Deep River Rd
Centerbrook, CT 06409

$562,400

$562,400

Local Information