271 Valley Rd, Cos Cob, CT 06807
OFF MARKET

271 Valley Rd
Cos Cob, CT 06807

Cos Cob
  • 5 Beds
  • 5.5 Baths
  • 5,932 sqft (on 0.39 acres)

$4,729,000

Trulia Estimate
as of Jul 12, 2026
Est. Refi. Payment $30,424/mo*
Refinance Your Home

$4,729,000

Trulia Estimate
as of Jul 12, 2026
Est. Refi. Payment $30,424/mo*
Refinance Your Home
5 Beds
5.5 Baths
5,932 sqft
(on 0.39 acres)

Local Information

  • Map ViewExplore the area around 271 Valley Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Water views like no other home in Cos Cob! This meticulously maintained imperial home is from a fairytale with its curved turret staircases, arches and rounded features. Rustic modern luxury is the theme as you step into a grand foyer. Majestic master wing with dual walk in closets, sitting area, & an awe-inspiring spa. 5 ensuite bedrooms. Custom kitchen with oversized island, breakfast nook with bay window and French doors to multi-level slate patio. Fantastic functionality with laundry on 1st and 2nd floors and spacious mudroom. Supreme lower level with 1 of 5 fireplaces, yoga room, and 1,532 square feet of additional space with gym & basketball court. Walk out lower level to water view patio with built in grill, boat house, and tool shed. Transport yourself to this pristine castle on the river.
271 Valley Rd, Cos Cob, CT 06807 is a 5 bedroom, 6 bathroom, 5,932 sqft single-family home in Cos Cob, built in 2008. It last sold for $2,750,000 on Mar 20, 2020. More recently, it was listed as a rental in December 2019 with an asking price of $22,500 per month. That rental listing was removed on December 13, 2019. It is currently off market. The Trulia Estimate is $4,729,000, with a rent estimate of $7,837/month.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 271 Valley Rd

Interior Features

Interior Details
BasementNumber of Rooms: 13
Heating & Cooling
Heating: RadiantAir ConditioningCooling System: CentralHeating Fuel: Radiant
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Wood
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 2008
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 0.39 acres

Price History for 271 Valley Rd

DatePriceEventSource
03/20/2020$2,750,000Sold
Greenwich MLS, Inc. #108094
01/06/2020$2,950,000PriceChange
Agent Provided
12/13/2019$22,500ListingRemovedAgent Provided
12/11/2019$22,500Listed For RentAgent Provided
11/04/2019$3,075,000PriceChange
Agent Provided
10/23/2019$3,245,000PriceChange
Agent Provided
10/16/2019$3,395,000Listed For SaleAgent Provided
10/26/2018$3,150,000Sold
Greenwich MLS, Inc. #103428
09/11/2018$3,295,000PendingAgent Provided
05/31/2018$3,295,000Listed For SaleAgent Provided
08/19/2005$860,000Sold
N/A
02/28/2002$422,000Sold
N/A

Market trends in Greenwich

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.1M
$340KMoM
Sale-to-List Price
102.7%
1.5%MoM
Price per sq ft
$801
$22MoM
Available listings
190
7MoM
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Property Tax and Assessment

Year2025
Tax$25,169
Assessment$2,036,510
Home facts updated by county records

Comparable Sales for 271 Valley Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
6 Fox Hollow Ln, Cos Cob, CT
0.11
Single-Family Home
$2,670,000
01/12/26
5
4
3,623
232 Valley Rd, Cos Cob, CT
0.14
Single-Family Home
$3,050,000
08/21/25
6
7
6,066
8 Fado Ln, Cos Cob, CT
0.14
Single-Family Home
$4,550,888
08/29/25
5
6.5
7,041
18 Cat Rock Rd, Cos Cob, CT
0.17
Single-Family Home
$3,600,000
07/18/25
6
6.5
6,272
552 River Rd, Cos Cob, CT
0.36
Single-Family Home
$2,691,500
03/27/26
4
4.5
4,078
74 Long Meadow Rd, Riverside, CT
0.47
Single-Family Home
$3,710,000
06/24/26
5
4.5
4,302
48 N Ridge Rd, Old Greenwich, CT
0.58
Single-Family Home
$3,900,000
07/02/26
5
5.5
4,627
16 Split Timber Pl, Riverside, CT
0.41
Single-Family Home
$2,420,000
08/15/25
5
3.5
3,243
551 River Rd, Cos Cob, CT
0.38
Single-Family Home
$2,285,000
10/27/25
5
3.5
3,634
112 Sheephill Rd, Riverside, CT
0.48
Single-Family Home
$4,350,000
07/06/26
6
7.5
6,447

Nearby homes

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Assigned Schools

These are the assigned schools for 271 Valley Rd.
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The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Cos Cob
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Cos Cob

At least 1 Trulia users voted on each feature.

  • 100 % Say neighbors are friendly

  • 100 % Say there are community events

  • 100 % Say there's holiday spirit

  • 100 % Say it's walkable to grocery stores

  • 100 % Say it's walkable to restaurants

  • 100 % Say parking is easy

  • 100 % Say car is needed

  • 100 % Say streets are well-lit

  • 100 % Say it's dog friendly

Sourced by Trulia users. Learn more about our methodology.

LGBTQ Local Legal Protections

Apartments for Rent

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Explore by feature - Pet Friendly

46 pet-friendly rentals in Cos Cob, CT

Explore by feature - Garage

63 rentals with a garage in Cos Cob, CT

Explore by feature - Air Conditioning

142 rentals with air conditioning in Cos Cob, CT

Explore by feature - Pool

24 rentals with a pool in Cos Cob, CT

Explore by feature - Washer/dryer

111 rentals with a washer/dryer in Cos Cob, CT

Explore by feature - Outdoor Space

28 rentals with an outdoor space in Cos Cob, CT

Homes for sale near 271 Valley Rd

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Off Market Homes Near 271 Valley Rd

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