66 Gregory Rd, Cos Cob, CT 06807
Property image
Property image
OFF MARKET

66 Gregory Rd
Cos Cob, CT 06807

Cos Cob
  • 5 Beds
  • 4.5 Baths
  • 5,559 sqft (on 0.31 acres)

$3,579,000

Trulia Estimate
as of Jul 9, 2026
Est. Refi. Payment $23,043/mo*
Refinance Your Home

$3,579,000

Trulia Estimate
as of Jul 9, 2026
Est. Refi. Payment $23,043/mo*
Refinance Your Home
5 Beds
4.5 Baths
5,559 sqft
(on 0.31 acres)

Local Information

  • Map ViewExplore the area around 66 Gregory Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Summer is coming and this magnificent home offers a beautiful outdoor oasis with heated swimming pool and large patio for entertaining. Upon entering the light filled colonial you are greeted by a 2 story gracious entry, open floor plan with a living room, formal dining room, eat-in gourmet kitchen adjacent to the lovely family room with fireplace and sliders out to the large patio. The second floor features a master bedroom suite with fireplace, luxurious master bath and 2 generous walk-in closets, 3 additional large bedrooms, 2 baths (1 en-suite and 1 Jack & Jill and the laundry room. The finished lower level with an oversized playroom/media room plus gym/ 5th bedroom with en-suite full bath and wine room continues to impress.
66 Gregory Rd, Cos Cob, CT 06807 is a 5 bedroom, 5 bathroom, 5,559 sqft single-family home in Cos Cob, built in 2009. It last sold for $2,330,000 on Jul 19, 2021. More recently, it was listed as a rental in July 2018 with an asking price of $10,750 per month. That rental listing was removed on August 2, 2018. It is currently off market. The Trulia Estimate is $3,579,000, with a rent estimate of $16,408/month.

Home Highlights

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

Home Details for 66 Gregory Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 10
Heating & Cooling
Heating: RadiantAir ConditioningCooling System: CentralHeating Fuel: Radiant
Levels, Entrance, & Accessibility
Stories: 2
Appliances & Utilities
DishwasherDryerMicrowaveWasher
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Wood
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 2009Year Updated: 2009
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.31 acres

Price History for 66 Gregory Rd

DatePriceEventSource
07/19/2021$2,330,000Sold
Smart MLS #170374697
05/24/2021$2,375,000PendingBerkshire Hathaway HomeServices New England Properties #170374697
05/24/2021$2,375,000ContingentSmart MLS #170374697
03/04/2021$2,375,000Listed For SaleAgent Provided
11/07/2019$2,145,000ListingRemovedAgent Provided
08/06/2019$2,145,000PriceChange
Agent Provided
05/08/2019$2,195,000PriceChange
Agent Provided
02/07/2019$2,245,000Listed For SaleAgent Provided
12/19/2018$2,295,000ListingRemovedAgent Provided
08/02/2018$10,750ListingRemovedAgent Provided
07/28/2018$10,750Listed For RentAgent Provided
05/02/2018$2,295,000PriceChange
Agent Provided
03/15/2018$2,390,000Listed For SaleAgent Provided
07/01/2011$1,825,000Sold
Smart MLS #98491099
08/07/2000$505,000Sold
N/A

Market trends in Greenwich

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.76M
$257KMoM
Sale-to-List Price
101.2%
1.0%MoM
Price per sq ft
$779
$4MoM
Available listings
183
8MoM
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$18,331
Assessment$1,483,230
Home facts updated by county records

Comparable Sales for 66 Gregory Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
70 Gregory Rd, Cos Cob, CT
0.02
Single-Family Home
$2,175,000
06/26/26
4
3
3,142
552 River Rd, Cos Cob, CT
0.47
Single-Family Home
$2,691,500
03/27/26
4
4.5
4,078
551 River Rd, Cos Cob, CT
0.48
Single-Family Home
$2,285,000
10/27/25
5
3.5
3,634
98 Hillcrest Park Rd, Cos Cob, CT
0.45
Single-Family Home
$2,610,000
05/29/26
4
3.5
3,298
2 Daffodil Ln, Cos Cob, CT
0.34
Single-Family Home
$3,314,000
06/26/26
5
4
4,777
420 Valley Rd, Cos Cob, CT
0.18
Single-Family Home
$1,300,000
04/14/26
4
2.5
1,601
37 Windsor Lane, Cos Cob, CT
0.23
Single-Family Home
$1,359,000
08/06/25
3
3
2,332
6 Fox Hollow Ln, Cos Cob, CT
0.67
Single-Family Home
$2,670,000
01/12/26
5
4
3,623
150 N Old Stone Bridge Rd, Cos Cob, CT
0.42
Single-Family Home
$2,550,000
05/15/26
4
4.5
4,161
29 Old Stone Bridge Rd, Cos Cob, CT
0.33
Single-Family Home
$3,000,000
05/21/26
4
4.5
3,734

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 66 Gregory 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.

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

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

39 pet-friendly rentals in Cos Cob, CT

Explore by feature - Garage

61 rentals with a garage in Cos Cob, CT

Explore by feature - Air Conditioning

137 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

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

Explore by feature - Outdoor Space

26 rentals with an outdoor space in Cos Cob, CT

Homes for sale near 66 Gregory Rd

Skip to last item
Skip to first item

Off Market Homes Near 66 Gregory Rd

Skip to last item
Skip to first item