Google street view image for 14 McGregory Rd, Sturbridge, MA 01566

Off market jun 1987 for $250K

$623,356

Est. refi paymentEst. refi $1,618/mo

•

2 ba

•

2,544

sq ft

14 McGregory Rd, Sturbridge, MA 01566

About this home

14 McGregory Rd is a 2,544 square foot house on a 1.22 acre lot with 3 bedrooms and 2 bathrooms. - it last sold on June 30, 1987 for $250,000. Based on Redfin's Sturbridge data, we estimate the home's value is $623,356.

Single-familyProperty Type

1776Year Built

1.22 acresLot Size

$245Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$623,356

$373K since sold in June 1987$7,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 23.2% higher than the average sale price ($506K) of 6 comparable homes.

SOLD OCT 16, 2026
$575,000
A
3 beds2.5 baths2,205 sq ft
32 Mcgregory Rd, Sturbridge, MA 01566
BOUGHT WITH REDFIN FEB 27, 2026
$615,000
B
3 beds2.5 baths2,305 sq ft
55 Fiske Hill Rd, Sturbridge, MA 01566
SOLD JUN 30, 2026
$582,900
C
3 beds2.5 baths2,183 sq ft
76 Fiske Hill Rd, Sturbridge, MA 01566
SOLD JUL 21, 2026
$430,000
D
3 beds2 baths2,050 sq ft
20 Marc Ave, Southbridge, MA 01550
SOLD JUN 24, 2026
$482,000
E
3 beds2 baths1,840 sq ft
8 Old Farm Rd, Sturbridge, MA 01566
BOUGHT WITH REDFIN OCT 28, 2026
$350,000
F
3 beds1.5 baths1,982 sq ft
23 Oakes Ave, Southbridge, MA 01550

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Earn from this home

Sell

$591,462

Est. take-home

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Est. cash available

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Rent

$3,123/mo

Redfin rental estimate

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Market trends in 01566, MA

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

99.8%

0.8% MoM

Median sale price

$520K

$153 MoM

Avg. days on market

29d

8 days MoM

Recently sold homes

4 MoM

New listings for sale

OPEN TODAY, 11AM TO 1PM
$1,100,000
3 beds2.5 baths2,315 sq ft
7 Cove Dr, Sturbridge, MA 01566
OPEN TODAY, 12PM TO 2PM
$439,000
3 beds1.5 baths1,958 sq ft
25 Wallace Rd, Sturbridge, MA 01566
$729,000
2 beds1 bath1,670 sq ft
33 Adams Rd, Sturbridge, MA 01566
See all

Provided by Redfin

Sale history for 14 McGregory Rd

Year

Property tax

Land + Additions

Assessment*

2023

$8,777 (+16.4%)

$97,800 + $387,900

$485,700

2021

$7,541

$88,400 + $354,300

$442,700

2020

$7,541 (+13.0%)

$84,300 + $312,200

$396,500

2019

$6,672 (+4.2%)

$86,700 + $261,700

$348,400

2018

$6,405 (+5.1%)

$82,500 + $247,000

$329,500

2017

$6,097 (+6.0%)

$79,600 + $234,700

$314,300

2015

$5,751 (+7.2%)

$77,200 + $221,700

$298,900

2014

$5,363 (+5.4%)

$77,200 + $202,100

$279,300

2013

$5,089 (+1.3%)

$88,600 + $194,900

$283,500

2012

$5,023 (+0.8%)

$88,600 + $196,300

$284,900

2011

$4,985 (+4.4%)

$88,600 + $219,300

$307,900

2010

$4,775 (+4.5%)

$95,100 + $233,100

$328,200

2009

$4,570

$111,800 + $249,200

$361,000

Tax history for 14 McGregory Rd

Year

Property tax

Land + Additions

Assessment*

2023

$8,777 (+16.4%)

$97,800 + $387,900

$485,700

2021

$7,541

$88,400 + $354,300

$442,700

2020

$7,541 (+13.0%)

$84,300 + $312,200

$396,500

2019

$6,672 (+4.2%)

$86,700 + $261,700

$348,400

2018

$6,405 (+5.1%)

$82,500 + $247,000

$329,500

2017

$6,097 (+6.0%)

$79,600 + $234,700

$314,300

2015

$5,751 (+7.2%)

$77,200 + $221,700

$298,900

2014

$5,363 (+5.4%)

$77,200 + $202,100

$279,300

2013

$5,089 (+1.3%)

$88,600 + $194,900

$283,500

2012

$5,023 (+0.8%)

$88,600 + $196,300

$284,900

2011

$4,985 (+4.4%)

$88,600 + $219,300

$307,900

2010

$4,775 (+4.5%)

$95,100 + $233,100

$328,200

2009

$4,570

$111,800 + $249,200

$361,000

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Property details

Interior

Basement Information
Basement Sq. Ft: 1,271

Bathroom Information
# of Full Baths: 2

Heating & Cooling
Heating Type: Forced Hot Water

Room Information
# of Rooms: 8

Exterior

Exterior Information
Physical Condition: Good
Building Style Type: Antique/Historic
Exterior Wall: Wood Siding/Shingle
Roof Shape Type: Gable

Property Information
Living Sq. Ft: 2,544
Gross Sq. Ft: 5,337
# of Units: 1
# of Stories: 2

Lot Information
# of Buildings: 1
Land Sq. Ft: 53,143
Municipality Name: STURBRIDGE
Acres: 1.22
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 3
Baths: 2.0
Sq. Ft.: 2,544
Stories: 2.0
Lot Size: 1.22 acres
Style: Single Family Residential
Year Built: 1776
Year Renovated: —
County: Worcester County
APN: 1703847

Home facts updated by county records on Jul 21, 2023

Around this home

Schools

K - 12
Preschool & daycare

Burgess Elementary School

Public PreK-6 • Assigned • 2.2mi

7/10

Tantasqua Regional Junior High School

Public 7-8 • Assigned • 5.7mi

5/10

Tantasqua Regional Senior High School

Public 9-12 • Assigned • 5.9mi

8/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

3/10 Heat Factor

7 days above 93° expected this year, 16 days in 30 years

6/10 Wind Factor

27% chance of strong winds in next 30 years

2/10 Air Factor

2 unhealthy days expected this year, 2 days in 30 years

Provided by First Street

Historical weather

Sturbridge, MA • 01566

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.9 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

8.9 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$593,000 – $717,000

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Nearby similar homes

$139,900

Land— sq ft

29 Whittemore Rd, Sturbridge, MA 01566

Large parcel • Fisk hill area • Water and sewer

$451,900

2 beds2 baths1,440 sq ft

2 Rose Ln, Sturbridge, MA 01566

Customize • Open-concept layout • Modern kitchen

$1,100,000

5 beds3.5 baths2,546 sq ft

11 Cove Dr, Sturbridge, MA 01566

Waterfront • Lakefront deck • Updated kitchen

$749,900

3 beds3.5 baths2,900 sq ft

70 Ellis Rd, Southbridge, MA 01550

Heated lower level • Custom theater • Media room

$399,000

3 beds2 baths1,150 sq ft

12 Fairground Rd, Sturbridge, MA 01566

Electrical updates • Serene setting • 7,405 sq ft lot

$260,000

3 beds2 baths1,471 sq ft

23 Charlton St, Southbridge, MA 01550

8,276 sq ft lot • 2 parking spots • Built 1925

New listings for sale in 01566

OPEN TODAY, 11AM TO 1PM

$1,100,000

3 beds2.5 baths2,315 sq ft

7 Cove Dr, Sturbridge, MA 01566

Waterfront retreat • Lake frontage • Private dock

OPEN TODAY, 12PM TO 2PM

$439,000

3 beds1.5 baths1,958 sq ft

25 Wallace Rd, Sturbridge, MA 01566

Finished den • Fenced in back yard • Rural setting

$729,000

2 beds1 bath1,670 sq ft

33 Adams Rd, Sturbridge, MA 01566

Waterfront living • Heated sunroom • First floor primary

Home values near 14 McGregory Rd

Data from public records.

Address	Redfin Estimate
1 McGregory Rd, Sturbridge, MA 6 Beds \| 3 Baths \| 3600 Sq. Ft.	$656,631
5 McGregory Rd, Sturbridge, MA 4 Beds \| 3 Baths \| 2350 Sq. Ft.	$581,357
18 McGregory Rd, Sturbridge, MA 4 Beds \| 2.5 Baths \| 2808 Sq. Ft.	$642,602
21 McGregory Rd, Sturbridge, MA 3 Beds \| 1.5 Baths \| 2210 Sq. Ft.	$607,558
10 McGregory Rd, Sturbridge, MA 4 Beds \| 2.5 Baths \| 2200 Sq. Ft.	$574,041
4 Williams Rd, Sturbridge, MA 4 Beds \| 3 Baths \| 2586 Sq. Ft.	$543,547
40 Fiske Hill Rd, Sturbridge, MA 4 Beds \| 2.5 Baths \| 2200 Sq. Ft.	$545,176

Address	Redfin Estimate
7 McGregory Rd, Sturbridge, MA 4 Beds \| 2 Baths \| 2400 Sq. Ft.	$566,879
22 McGregory Rd, Sturbridge, MA 2 Beds \| 1.5 Baths \| 1700 Sq. Ft.	$486,745
17 McGregory Rd, Sturbridge, MA 3 Beds \| 2 Baths \| 1717 Sq. Ft.	$465,253
44 McGregory Rd, Sturbridge, MA 4 Beds \| 3 Baths \| 2800 Sq. Ft.	$644,714
11 McGregory Rd, Sturbridge, MA 4 Beds \| 2.5 Baths \| 2024 Sq. Ft.	$540,741
3 Newton Pl, Sturbridge, MA 3 Beds \| 3 Baths \| 1534 Sq. Ft.	$507,060
36 Fiske Hill Rd, Sturbridge, MA 4 Beds \| 1 Baths \| 1757 Sq. Ft.	$393,887

Address	Redfin Estimate
6 McGregory Rd, Sturbridge, MA 4 Beds \| 2 Baths \| 2233 Sq. Ft.	$637,170
19 McGregory Rd, Sturbridge, MA 3 Beds \| 2.5 Baths \| 2436 Sq. Ft.	$524,691
50 McGregory Rd, Sturbridge, MA 4 Beds \| 2.5 Baths \| 2080 Sq. Ft.	$571,942
13 McGregory Rd, Sturbridge, MA 4 Beds \| 2.5 Baths \| 2200 Sq. Ft.	$577,059
9 McGregory Rd, Sturbridge, MA 4 Beds \| 2.5 Baths \| 2024 Sq. Ft.	$570,763
6 Newton Pl, Sturbridge, MA 6 Beds \| 5.5 Baths \| 3506 Sq. Ft.	$615,888
46 Fiske Hill Rd, Sturbridge, MA 4 Beds \| 2 Baths \| 1771 Sq. Ft.	$622,030

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GreatSchools Ratings provided by GreatSchools.org.

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