44 Macgregor Dr, Stamford, CT 06902
OFF MARKET

$1,486,100

Trulia Estimate
  • 4 Beds
  • 4 Baths
  • 3,366 sqft (on 1.01 acres)

44 Macgregor Dr, Stamford, CT 06902

Westover
Est. Refi. Payment $9,761/mo*
Refinance Your Home
Currently Off Market - Sold Feb 13, 2003 for $517,000

Home Value

Trulia Estimate
$1.49M
Since last month
Increased$36K (+2.5%)
Since last year
Increased$104K (+7.5%)
Since last sale
Increased$971K (+187.8%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +86% in the last 10 years
MonthEstimated value
2026
August 2026$1.49M
July 2026$1.45M
June 2026$1.48M
May 2026$1.48M
April 2026$1.43M
March 2026$1.41M
February 2026$1.36M
January 2026$1.33M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
42 Akbar Road, Stamford, CT
0.13
Single-Family Home
$975,000
08/14/26
4
3
2,642
133 Macgregor Drive, Stamford, CT
0.25
Single-Family Home
$980,000
09/02/25
3
2.5
2,970
90 Akbar Rd, Stamford, CT
0.29
Single-Family Home
$880,000
02/10/26
4
3
2,233
36 Carriage Dr, Stamford, CT
0.38
Single-Family Home
$1,000,000
05/22/26
3
3
3,112
45 Carriage Dr S, Stamford, CT
0.43
Single-Family Home
$1,260,000
07/13/26
4
2.5
2,893
244 Westwood Road, Stamford, CT
0.20
Single-Family Home
$845,000
04/17/26
4
2.5
1,852
75 Westwood Road, Stamford, CT
0.52
Single-Family Home
$820,000
07/07/26
4
2.5
2,496
887 Westover Road, Stamford, CT
0.54
Single-Family Home
$875,000
12/31/25
5
4.5
3,530
59 Westwood Road, Stamford, CT
0.53
Single-Family Home
$1,019,000
05/27/26
4
3
2,452
172 Roxbury Road, Stamford, CT
0.32
Single-Family Home
$680,000
09/26/25
3
1.5
1,506

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
42 Akbar Road, Stamford, CT 06902
0.13
$975,000
4
3
2,642
Recently Sold
7 Dancy Drive, Stamford, CT 06902
0.14
$1,384,100
4
3.5
3,238
Off Market
35 Drum Hill Lane, Stamford, CT 06902
0.13
$1,255,400
4
2.5
2,486
Off Market
244 Westwood Road, Stamford, CT 06902
0.20
$845,000
4
2.5
1,852
Recently Sold
677 West Hill Road, Stamford, CT 06902
0.19
$2,195,000
6
4.5
10,746
For Sale
517 West Hill Road, Stamford, CT 06902
0.26
-
5
3
2,760
Off Market
279 Westwood Road, Stamford, CT 06902
0.24
$1,294,200
3
2.5
2,544
Off Market
124 Akbar Rd, Stamford, CT 06902
0.25
$1,619,800
4
2.5
3,462
Off Market
133 Macgregor Drive, Stamford, CT 06902
0.25
-
3
2.5
2,970
Off Market
106 Akbar Rd, Stamford, CT 06902
0.26
-
3
2.5
2,427
Off Market
56 West Hill Lane, Stamford, CT 06902
0.25
$1,272,800
2
2.5
2,404
Off Market
54 West Hill Lane, Stamford, CT 06902
0.27
$1,981,800
4
4
4,767
Off Market

Local Information

  • Map ViewExplore the area around 44 Macgregor Dr.
  • 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
1.01 acres
Living Area
3,366 sqft
Price/Sqft
$442
Parking
Garage

About this House

This single-family home is located at 44 Macgregor Dr, Stamford, CT. 44 Macgregor Dr is in the Westover neighborhood in Stamford, CT and in ZIP code 06902. This property has 4 bedrooms, 5 bathrooms and approximately 3,366 sqft of floor space. This property has a lot size of 1.01 acres and was built in 1960.
44 Macgregor Dr, Stamford, CT 06902 is a 4 bedroom, 5 bathroom, 3,366 sqft single-family home in Westover, built in 1960. It last sold for $517,000 on Feb 13, 2003. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,486,100, with a rent estimate of $7,816/month.

Home Details for 44 Macgregor Dr

Interior Features

Interior Details
BasementAtticNumber of Rooms: 9Types of Rooms: Walk In Closet, Breakfast Nook, Family Room, Laundry Room, Master Bath, Office, Recreation RoomCeiling Fan
Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or Spa
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Shingle, WoodLawnPatioPorch
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1960Year Updated: 2010
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 1.01 acres

Price and Tax history

DateEventPrice
Feb 13, 2003
Source: Smart MLS #98138518
Sold
$517,000

Market trends in Stamford

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$679K
$48.83KMoM
Sale-to-List Price
102.7%
0.2%MoM
Price per sq ft
$403
$5MoM
Available listings
287
7MoM

Around this home

Neighborhood Overview

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

What Locals Say about Westover

At least 22 Trulia users voted on each feature.

  • 96 % Say car is needed

  • 92 % Say it's dog friendly

  • 90 % Say there's wildlife

  • 89 % Say yards are well-kept

  • 83 % Say it's quiet

  • 81 % Say parking is easy

  • 77 % Say there's holiday spirit

  • 59 % Say people would walk alone at night

  • 56 % Say neighbors are friendly

  • 53 % Say they plan to stay for at least 5 years

  • 42 % Say kids play outside

  • 32 % Say streets are well-lit

  • 25 % Say there are community events

  • 19 % Say there are sidewalks

  • 13 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Julia
    "It’s pretty, close to everything and very livable. He proximity to the Merritt is fabulous and we also love walking to Mianus State Park. "
    1
    Flag
  • Steve B.
    "Quit neighborhood with traffic only from locals and service people."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 44 Macgregor Dr

  • What is 44 Macgregor Dr estimated to be worth?
    Trulia's estimated value for 44 Macgregor Dr in Stamford, CT is $1,486,100.
  • What is the price history for 44 Macgregor Dr?
    44 Macgregor Dr in Stamford, CT last sold for $517,000 in February 2003.
  • Is Stamford a buyer's or seller's market?
    Stamford is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Stamford?
    The median sale price in Stamford is $679K. That is up $48.83K from the prior month.
  • Does 44 Macgregor Dr have air conditioning?
    Yes, 44 Macgregor Dr in Stamford, CT has air conditioning.
  • Does 44 Macgregor Dr have laundry facilities?
    Yes, 44 Macgregor Dr in Stamford, CT has in-unit laundry.

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