OFF MARKET

Off Market Apr 2025 for $585K

$606,153

•

2,210

sq ft

21 Mcgregory Rd, Sturbridge, MA 01566

About this home

Sunday Open House Canceled. From the charming cupola to the stunning lot with gorgeous perennial gardens, this home in the sought after McGregory Road Neighborhood is amazing! Gracious one level living, lovingly maintained and loaded with upgrades. Features include classic formals with hardwoods, Dining Room with built in corner cupboard, Living Room with propane fireplace, fully applianced custom renovated Kitchen and Guest Bath. The main level Bedroom wing includes hardwood floors and a renovated main Bath with a heated floor! There is a 2nd Floor multi purpose Bonus Room and a huge walk-in Attic. The finished lower level Family Room is designed with lots of built-ins including a desk and a wet Bar with cabinets. Focusing on quiet enjoyment or entertaining possibilities is a striking 3 season glassed in Sun Room and deck overlooking the wonderful level backyard. The convenient neighborhood location off of Fiske Hill offers ease of highway access for commuters.

Single-familyProperty Type

1955Year Built

0.65 acresLot Size

$274Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Lorraine Herbert • RE/MAX Prof Associates

Bought with The Jarboe Group • Keller Williams Pinnacle Central

Redfin checked: a few seconds ago

•Source:MLS PIN #73350067

Redfin Estimate

$606,153

$21K since sold in April 2025$6,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 40.9% higher than the average sale price ($430K) of 6 comparable homes.

SOLD AUG 28, 2026
$385,000
A
3 beds1 bath2,184 sq ft
60 Pinedale St, Southbridge, MA 01550
SOLD JUL 14, 2026
$435,000
B
3 beds1.5 baths1,735 sq ft
46 Willard Rd, Sturbridge, MA 01566
SOLD OCT 29, 2025
$555,000
C
3 beds2 baths2,263 sq ft
6 Hillside Dr, Sturbridge, MA 01566
SOLD JUN 24, 2026
$482,000
D
3 beds2 baths1,840 sq ft
8 Old Farm Rd, Sturbridge, MA 01566
SOLD AUG 19, 2026
$370,000
E
3 beds1.5 baths944 sq ft
50 Roosevelt Dr, Southbridge, MA 01550
SOLD JUL 31, 2026
$355,000
F
3 beds2 baths2,160 sq ft
585 Charlton St, Southbridge, MA 01550

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Earn from this home

Sell

$118,112

Est. take-home

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Rent

$2,927/mo

Redfin rental estimate

List your home for rent

Market trends in 01566, MA

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

100.6%

0.0% MoM

Median sale price

$520K

$15K MoM

Avg. days on market

21d

0 days MoM

Recently sold homes

2 MoM

New listings for sale

OPEN TODAY, 12PM TO 2PM
$389,900
3 beds1 bath912 sq ft
44 New Boston Rd, Sturbridge, MA 01566
OPEN TODAY, 1PM TO 3PM
$800,000
4 beds4 baths3,146 sq ft
3 Goodrich Rd, Sturbridge, MA 01566
$375,000
2 beds2 baths1,788 sq ft
92 Colonial Dr #92, Sturbridge, MA 01566
See all

Provided by Redfin

Sale history for 21 Mcgregory Rd

Year

Property tax

Land + Additions

Assessment*

2023

$6,534 (+12.7%)

$89,100 + $272,500

$361,600

2021

$5,799

$80,800 + $248,000

$328,800

2020

$5,799 (+7.8%)

$77,000 + $227,900

$304,900

2019

$5,377 (+4.0%)

$79,300 + $201,500

$280,800

2018

$5,171 (+5.0%)

$75,600 + $190,400

$266,000

2017

$4,924 (+4.5%)

$72,600 + $181,200

$253,800

2015

$4,710 (+6.8%)

$70,400 + $174,400

$244,800

2014

$4,410 (−11.7%)

$70,400 + $159,300

$229,700

2013

$4,994 (+0.9%)

$82,500 + $195,700

$278,200

2012

$4,951 (+7.2%)

$82,500 + $198,300

$280,800

2011

$4,619 (+3.5%)

$82,500 + $202,800

$285,300

2010

$4,462 (+3.5%)

$88,300 + $218,400

$306,700

2009

$4,313

$103,900 + $236,800

$340,700

Tax history for 21 Mcgregory Rd

Year

Property tax

Land + Additions

Assessment*

2023

$6,534 (+12.7%)

$89,100 + $272,500

$361,600

2021

$5,799

$80,800 + $248,000

$328,800

2020

$5,799 (+7.8%)

$77,000 + $227,900

$304,900

2019

$5,377 (+4.0%)

$79,300 + $201,500

$280,800

2018

$5,171 (+5.0%)

$75,600 + $190,400

$266,000

2017

$4,924 (+4.5%)

$72,600 + $181,200

$253,800

2015

$4,710 (+6.8%)

$70,400 + $174,400

$244,800

2014

$4,410 (−11.7%)

$70,400 + $159,300

$229,700

2013

$4,994 (+0.9%)

$82,500 + $195,700

$278,200

2012

$4,951 (+7.2%)

$82,500 + $198,300

$280,800

2011

$4,619 (+3.5%)

$82,500 + $202,800

$285,300

2010

$4,462 (+3.5%)

$88,300 + $218,400

$306,700

2009

$4,313

$103,900 + $236,800

$340,700

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

Public record

Beds

Baths

1.5

Stories

Lot width

—

Lot depth

—

Lot size

0.65 Acres

Year renovated

—

Sq. Ft.

1,599

Year built

1955

Style

Single Family Residential

County

Worcester County

APN

1703841

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 21, 2023.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 2
# of Covered Spaces: 2
Parking Spaces: 4
AttachedGarageYN: Yes
Parking Features: Attached, Garage Door Opener, Storage, Workshop in Garage, Paved Drive, Off Street, Paved

Interior

Bedroom Information
Main Level Bedrooms: 3

Master Bedroom Information
Level: Main,First
Features: Closet,Flooring - Hardwood

Bedroom #2 Information
Level: Main,First
Features: Closet,Flooring - Hardwood

Bedroom #3 Information
Level: Main,First
Features: Closet,Flooring - Hardwood

Bathroom Information
# of Bathrooms (Full): 1
# of Bathrooms (Half): 1
Main Level Bathrooms: 2

Bathroom #1 Information
Level: Main,First
Features: Bathroom - Full,Closet - Linen,Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid,Remodeled

Bathroom #2 Information
Level: Main,First
Features: Bathroom - Half,Flooring - Stone/Ceramic Tile,Remodeled,Pedestal Sink

Living Room Information
Level: Main,First
Features: Flooring - Hardwood,Exterior Access

Family Room Information
Level: Basement
Features: Closet/Cabinets - Custom Built,Flooring - Wall to Wall Carpet,Wet Bar

Dining Room Information
Level: Main,First
Features: Closet/Cabinets - Custom Built,Flooring - Hardwood,Window(s) - Picture,Chair Rail

Kitchen Information
Level: Main,First
Features: Flooring - Stone/Ceramic Tile,Pantry,Countertops - Stone/Granite/Solid,Kitchen Island,Cabinets - Upgraded,Exterior Access

Basement Information
Basement: Full, Finished, Interior Entry, Bulkhead, Concrete

Laundry Information
Laundry Features: In Basement, Washer Hookup

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 1
Fireplace Features: Living Room

Interior Features
# of Rooms (Total): 8
Window Features: Insulated Windows, Screens
Flooring: Wood, Tile
Interior Features: Bonus Room, Sun Room, Walk-Up Attic

Exterior

Building Information
Building Area (Total): 2,210
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Actual
Color: white

Exterior Features
Fencing: Fenced
Roof: Shingle
Patio And Porch Features: Porch - Enclosed, Deck - Composite, Patio
Exterior Features: Porch - Enclosed, Deck - Composite, Patio, Rain Gutters, Screens, Fenced Yard, Garden, Stone Wall

Property Information
PropertySubType: Single Family Residence
Security Features: Security System

Lot Information
Lot Size (Acres): 0.65
Lot Features: Corner Lot
Frontage Length: 160
Road Surface Type: Paved
Road Frontage Type: Public
Road Responsibility: Public Maintained Road

Financial

Tax Information
Tax Annual Amount: $7,196
Tax Year: 2025

Utilities

Utility Information
Utilities: for Electric Range, for Electric Oven, Washer Hookup, Icemaker Connection, Generator Connection
Sewer: Public Sewer
Water Source: Public
Electric: Circuit Breakers, Generator Connection

Heating & Cooling
Has Heating
Has Cooling
Heating: Baseboard, Electric Baseboard, Oil, Leased Propane Tank
Cooling: Central Air

Location

Location Information
Directions: Rt 20 or Rt 131 to Fiske Hill Rd to McGregory, sign
UnparsedAddress: 21 Mcgregory Rd, Sturbridge MA 01566

Community Information
Senior CommunityYN: No
Community Features: Shopping, Walk/Jog Trails, Golf, Medical Facility, Conservation Area, Highway Access

Public facts

Beds: 3
Baths: 1.5
Sq. Ft.: 1,599
Stories: 1.0
Lot Size: 0.65 acres
Style: Single Family Residential
Year Built: 1955
Year Renovated: —
County: Worcester County
APN: 1703841

Home facts updated by county records on Jul 21, 2023

Other

Miscellaneous Information
Heat Zones: 3

Listing Information
Exclusions: Window Treatments, Area Rugs And Fireplace Tools Excluded
StandardStatus: Closed

Around this home

Schools

Burgess Elementary School

Public PreK-6 • Assigned • 2.1mi

7/10

Tantasqua Regional Junior High School

Public 7-8 • Assigned • 5.6mi

5/10

Tantasqua Regional Senior High School

Public 9-12 • Assigned • 5.8mi

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

$576,000 – $698,000

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OPEN TODAY, 12PM TO 2PM

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OPEN TODAY, 1PM TO 3PM

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Home values near 21 Mcgregory Rd

Data from public records.

Address	Redfin Estimate
43 McGregory Road, Sturbridge, MA 4 Beds \| 2.5 Baths \| 2997 Sq. Ft.	$709,230
22 McGregory Road, Sturbridge, MA 2 Beds \| 1.5 Baths \| 1700 Sq. Ft.	$482,661

Address	Redfin Estimate
45 McGregory Road, Sturbridge, MA 3 Beds \| 1.5 Baths \| 2382 Sq. Ft.	$568,951
19 McGregory Road, Sturbridge, MA 3 Beds \| 2.5 Baths \| 2436 Sq. Ft.	$535,565

Address	Redfin Estimate
46 McGregory Road, Sturbridge, MA 4 Beds \| 2.5 Baths \| 2600 Sq. Ft.	$679,697
18 McGregory Road, Sturbridge, MA 4 Beds \| 2.5 Baths \| 2808 Sq. Ft.	$634,295

Property information provided by MLS PIN when last listed in 2025. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 01566, MA

Sale history for 21 Mcgregory Rd

Tax history for 21 Mcgregory Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 01566

Home values near 21 Mcgregory Rd

More real estate resources