44 Gregory Rd, Cos Cob, CT 06807
OFF MARKET

44 Gregory Rd
Cos Cob, CT 06807

Cos Cob
  • 4 Beds
  • 3.5 Baths
  • 3,000 sqft (on 0.28 acres)

$1,921,000

Trulia Estimate
as of Aug 3, 2026
Est. Refi. Payment $12,625/mo*
Refinance Your Home

$1,921,000

Trulia Estimate
as of Aug 3, 2026
Est. Refi. Payment $12,625/mo*
Refinance Your Home
4 Beds
3.5 Baths
3,000 sqft
(on 0.28 acres)

Local Information

  • Map ViewExplore the area around 44 Gregory Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1960
Lot Size
0.28 acres
Living Area
3,000 sqft
Price/Sqft
$640
Parking
Garage

About this House

This single-family home is located at 44 Gregory Rd, Cos Cob, CT. 44 Gregory Rd is in the Cos Cob neighborhood in Cos Cob, CT and in ZIP code 06807. This property has 4 bedrooms, 4 bathrooms and approximately 3,000 sqft of floor space. This property has a lot size of 0.28 acres and was built in 1960.
44 Gregory Rd, Cos Cob, CT 06807 is a 4 bedroom, 4 bathroom, 3,000 sqft single-family home in Cos Cob, built in 1960. It is currently off market. The Trulia Estimate is $1,921,000, with a rent estimate of $7,940/month.

Home Details for 44 Gregory Rd

Interior Features

Interior Details
BasementAdditional StorageAtticNumber of Rooms: 9Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Library, Master Bath, Office, Recreation Room, WorkshopStorageCeiling Fan
Heating & Cooling
Heating: Baseboard, GasAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Concrete, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: VinylLawnPatioPorchSprinkler System
Parking & Garage
GarageParking Spaces: 6Parking: Garage Attached, Off Street

Property Information

Year Built
Year Built: 1960Year Updated: 2010
Property Type / Style
Property Type: Single Family HomeArchitecture: Split-level

Community

Units in Building: 1

Lot Information

Lot Area: 0.28 acres

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$9,067
Assessment$733,670
Home facts updated by county records

Comparable Sales for 44 Gregory Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
70 Gregory Rd, Cos Cob, CT
0.15
Single-Family Home
$2,175,000
06/26/26
4
3
3,142
37 Windsor Lane, Cos Cob, CT
0.12
Single-Family Home
$1,359,000
08/06/25
3
3
2,332
420 Valley Rd, Cos Cob, CT
0.17
Single-Family Home
$1,300,000
04/14/26
4
2.5
1,601
98 Hillcrest Park Rd, Cos Cob, CT
0.34
Single-Family Home
$2,610,000
05/29/26
4
3.5
3,298
350 Valley Rd, Cos Cob, CT
0.23
Single-Family Home
$1,530,000
11/21/25
4
3
1,982
552 River Rd, Cos Cob, CT
0.34
Single-Family Home
$2,691,500
03/27/26
4
4.5
4,078
551 River Rd, Cos Cob, CT
0.36
Single-Family Home
$2,285,000
10/27/25
5
3.5
3,634
56 Cognewaugh Rd, Cos Cob, CT
0.37
Single-Family Home
$1,100,000
04/10/26
4
3
1,800
92 Hillcrest Park Rd, Old Greenwich, CT
0.33
Single-Family Home
$2,950,000
12/15/25
5
3.5
3,339
120 Florence Rd, Riverside, CT
0.73
Single-Family Home
$1,280,000
06/01/26
4
3
2,068

Nearby homes

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Assigned Schools

These are the assigned schools for 44 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

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Explore by feature - Pet Friendly

42 pet-friendly rentals in Cos Cob, CT

Explore by feature - Garage

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Explore by feature - Air Conditioning

122 rentals with air conditioning in Cos Cob, CT

Explore by feature - Pool

20 rentals with a pool in Cos Cob, CT

Explore by feature - Washer/dryer

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

Explore by feature - Outdoor Space

27 rentals with an outdoor space in Cos Cob, CT

Homes for sale near 44 Gregory Rd

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Off Market Homes Near 44 Gregory Rd

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