21 McGregory Rd, Sturbridge, MA 01566
Property image
Property image
OFF MARKET

$610,300

Trulia Estimate
  • 3 Beds
  • 1.5 Baths
  • 2,210 sqft (on 0.65 acres)

21 McGregory Rd, Sturbridge, MA 01566

Est. Refi. Payment $3,800/mo*
Refinance Your Home
Currently Off Market - Sold Apr 23, 2025 for $585,000

Home Value

Trulia Estimate
$610K
Since last month
Increased$6K (+1%)
Since last year
Increased$22K (+3.8%)
Since last sale
Increased$27K (+4.6%)
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 +132% in the last 10 years
MonthEstimated value
2026
August 2026$612K
August 2026$611K
July 2026$606K
June 2026$600K
May 2026$602K
April 2026$600K
March 2026$596K
February 2026$598K
January 2026$599K
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 McGregory Rd, Sturbridge, MA
0.09
Single-Family Home
$572,000
09/05/25
4
2.5
2,049
55 Fiske Hill Rd, Sturbridge, MA
0.16
Single-Family Home
$615,000
02/27/26
3
2.5
2,305
51 Fiske Hill Rd, Sturbridge, MA
0.11
Single-Family Home
$607,500
01/30/26
4
3
2,520
1 Leslie Ln, Sturbridge, MA
0.13
Single-Family Home
$425,000
12/31/25
3
1
1,341
75 Fairview Park Rd, Sturbridge, MA
0.19
Single-Family Home
$412,000
07/07/26
2
1
1,404
76 Fiske Hill Rd, Sturbridge, MA
0.46
Single-Family Home
$582,900
06/30/26
3
2.5
2,183
8 Blueberry Ln, Sturbridge, MA
0.66
Single-Family Home
$545,000
03/12/26
4
2
2,367
74 Fiske Hill Rd, Sturbridge, MA
0.43
Single-Family Home
$634,900
09/26/25
3
2.5
3,552
8 Old Farm Rd, Sturbridge, MA
0.70
Single-Family Home
$482,000
06/24/26
3
2
1,840
10 Blueberry Ln, Sturbridge, MA
0.64
Single-Family Home
$600,000
06/29/26
4
3
2,040

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 McGregory Rd, Sturbridge, MA 01566
0.09
$592,200
4
2.5
2,049
Off Market
3 Newton Pl, Sturbridge, MA 01566
0.13
$529,100
3
3
1,534
Off Market
32 McGregory Rd, Sturbridge, MA 01566
0.09
$589,900
3
2.5
2,205
For Sale
51 Fiske Hill Rd, Sturbridge, MA 01566
0.11
$607,500
4
3
2,520
Recently Sold
7 McGregory Rd, Sturbridge, MA 01566
0.17
$556,100
4
2
2,400
Off Market
38 McGregory Rd, Sturbridge, MA 01566
0.13
$606,800
4
3.5
2,016
Off Market
1 Leslie Ln, Sturbridge, MA 01566
0.13
$425,000
3
1
1,341
Recently Sold
42 Fairview Park Rd, Sturbridge, MA 01566
0.19
$533,600
4
2.5
1,938
Off Market
4 Williams Rd, Sturbridge, MA 01566
0.20
$549,900
4
3
2,586
For Sale
55 Fiske Hill Rd, Sturbridge, MA 01566
0.16
$615,000
3
2.5
2,305
Recently Sold
56 Fiske Hill Rd, Sturbridge, MA 01566
0.17
$667,400
4
2.5
2,223
Off Market

Local Information

  • Map ViewExplore the area around 21 McGregory Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1955
Lot Size
0.65 acres
Living Area
2,210 sqft
Price/Sqft
$276
Parking
2 Car Garage

About this House

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.
21 McGregory Rd, Sturbridge, MA 01566 is a 3 bedroom, 2 bathroom, 2,210 sqft single-family home built in 1955. It last sold for $585,000 on Apr 23, 2025 (8% above the $539,900 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $610,300, with a rent estimate of $3,017/month.
Last check for updates: about 24 hours ago
Listed by Lorraine Herbert, (508) 864-4232
RE/MAX Prof Associates, (508) 347-9595
Bought with: The Jarboe Group, (508) 322-1499, Keller Williams Pinnacle Central, (508) 754-3020
Source: MLS PIN, MLS#73350067

Home Details for 21 McGregory Rd

Interior Features

Interior Details
Basement: Full,Finished,Interior Entry,Bulkhead,ConcreteNumber of Rooms: 8Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bathroom 1, Bathroom 2, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Main Level Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (half): 1Number of Bathrooms (main level): 2
Dimensions and Layout
Living Area: 2210 Square Feet
Appliances & Utilities
Utilities: for Electric Range, for Electric Oven, Washer Hookup, Icemaker Connection, Generator ConnectionAppliances: Water Heater, Range, Dishwasher, Microwave, Refrigerator, Plumbed For Ice MakerDishwasherLaundry: In Basement,Washer HookupMicrowaveRefrigerator
Heating & Cooling
Heating: Baseboard,Electric Baseboard,Oil,Leased Propane TankHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Living RoomHas a FireplaceNo Spa
Gas & Electric
Electric: Circuit Breakers, Generator Connection
Windows, Doors, Floors & Walls
Window: Insulated Windows, ScreensFlooring: Wood, Tile
Levels, Entrance, & Accessibility
Floors: Wood, Tile
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Porch - Enclosed, Deck - Composite, PatioFencing: FencedExterior: Porch - Enclosed, Deck - Composite, Patio, Rain Gutters, Screens, Fenced Yard, Garden, Stone WallFoundation: Concrete PerimeterGarden
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Open Parking Spaces: 4No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 6Parking: Attached,Garage Door Opener,Storage,Workshop in Garage,Paved Drive,Off Street,Paved
Frontage
Road Frontage: PublicResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Farm & Range
Frontage Length: 160.00
Finished Area
Finished Area (above surface): 1599Finished Area (below surface): 611

Property Information

Year Built
Year Built: 1955
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape,Ranch
Building
Construction Materials: FrameNot Attached PropertyDoes Not Include Home Warranty
Property Information
Not Included in Sale: Window Treatments, Area Rugs And Fireplace Tools ExcludedParcel Number: M:434 B:000 L:3531021, 1703841

Price & Status

Price
List Price: $539,900
Status Change & Dates
Off Market Date: Sat Apr 05 2025

Active Status

MLS Status: Sold

Location

Direction & Address
City: SturbridgeCommunity: McGregory Rd Neighborhood
School Information
Elementary School: BurgessJr High / Middle School: Tantasqua Jr HiHigh School: Tantasqua Sr Hi

Building

Building Area
Building Area: 2210 Square Feet

Community

Community Features: Shopping, Walk/Jog Trails, Golf, Medical Facility, Conservation Area, Highway AccessNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.65 acres

Miscellaneous

BasementMls Number: 73350067Above Grade Unfinished Area: 1599

Additional Information

ShoppingWalk/Jog TrailsGolfMedical FacilityConservation AreaHighway Access

Price and Tax history

DateEventPrice
Apr 23, 2025
Source: MLS PIN #73350067
Sold
$585,000
Mar 31, 2025
Source: MLS PIN #73350067
Listed For Sale
$539,900

Market trends in Sturbridge

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
29
2MoM

Around this home

What Locals Say about Sturbridge

At least 52 Trulia users voted on each feature.

  • 94 % Say car is needed

  • 88 % Say parking is easy

  • 83 % Say there's holiday spirit

  • 82 % Say it's dog friendly

  • 79 % Say yards are well-kept

  • 75 % Say it's quiet

  • 72 % Say there's wildlife

  • 67 % Say people would walk alone at night

  • 61 % Say kids play outside

  • 52 % Say they plan to stay for at least 5 years

  • 51 % Say neighbors are friendly

  • 44 % Say streets are well-lit

  • 38 % Say there are community events

  • 35 % Say it's walkable to restaurants

  • 28 % Say there are sidewalks

  • 25 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Pbbw9dhf4k
    "Farmers markets and social family events. Fun competitions. Music bingo. Trivia nights. Holiday events. "
    0
    Flag
  • Jim Meskauskas
    "You have to drive everywhere. There is no public transportation. I also work from home. There’s nothing else to say."
    0
    Flag
  • James Esterbrook
    "It’s an upper middle class area where people have pets and they walk them….nothing more, nothing less."
    0
    Flag
  • Betsy L.
    "Good town to raise kids in, school system is top notch. Been here for 25 years, never regretted our decision to move here."
    0
    Flag
  • Jfclancey
    "Excellent highway access. Can get to the Pike and i-84 in minutes. Easy to get to Hartford, Worcester, Marlboro, Boston and Springfield. "
    2
    Flag
  • Eyren L.
    "Very quiet, but close to the highway for the commuters. No public transportation beyond school buses, which isn't good for anyone who doesn't drive. Mainly restaurants and hotels are what keep the town thriving, but there are some great hole in the wall shops."
    2
    Flag
  • James E.
    "I love living here, moving here was one of the best decisions I’ve made. Great schools, restaurants, sense of community and lots of young families moving to the area. Excellent amenities like farmers market, farms, outdoor recreation spaces..... "
    0
    Flag
  • Jfgannon1
    "I don’t commute anymore. Work from home. Is an ideal location, though, at the junction of 2 interstate highways, 1US Route 20, SR 131."
    0
    Flag
  • Eva G.
    "Farmers market every Sunday on the Common during the Summer through early Fall. Senior Center on Main Street is well organized and offers daily exercise classes at minimal cost, linch everyday and a fantastic newsletter which outlines the month’s events."
    0
    Flag
  • Jfgannon1
    "Friendly families. Cup d sac. Well maintained yards. Rural. Wildlife abounds. Children in the neighborhood."
    0
    Flag
  • Elizabethlouisepotter
    "There’s a dance studio and a paint-and-sip. The school district is competitive and well-run. Great commuter town."
    0
    Flag
  • Carrina G.
    "Great school, and friendly people. Lots of walking trails. And amazing restaurants. And lots of history "
    1
    Flag
  • Carrina G.
    "Not much Francisco during the day. But a little bit of Traffic during morning and afternoon hours. Busses can be an issue during commute to work. "
    0
    Flag
  • Robert d.
    "Great restaurants. Extremely high taxes and very business unfriendly community. I think maintaining a high tax rate with little to no business opportunities helps to ensure that only the right type of demographic lives here!"
    0
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  • Robert d.
    "Incredibly high taxes & a generally snobby attitude from most of the townspeople. The town is not at all business friendly."
    0
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  • skiross
    "This area, known as Walker Pond, is an "association" development centered on one side of a lake with a state park on the other side. The neighborhood is the greatest around for several reasons. The association dues are approx. $200/year and includes resident use of two beaches with playground equipment for children, boat docks, dedicated swimming areas, volleyball, a ball field, tennis courts, and a horse stable. The area has approx 125 homes and is extremely safe for chidren playing outside. (Cars do not pass through to get to anywhere else.) It is a wonderful family neighborhood! The association is also quite active with 4th of July events, lobster bakes, children's Christmas parties and last day of school picnics, neighborhood yard sales, etc. It is quiet, idyllic, friendly, and happy!"
    0
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LGBTQ Local Legal Protections

The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.

Frequently asked questions about 21 McGregory Rd

  • What is 21 McGregory Rd estimated to be worth?
    Trulia's estimated value for 21 McGregory Rd in Sturbridge, MA is $610,300.
  • What is the price history for 21 McGregory Rd?
    21 McGregory Rd in Sturbridge, MA last sold for $585,000 in April 2025.
  • Is Sturbridge a buyer's or seller's market?
    Sturbridge is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Sturbridge?
    Residents describe Sturbridge, MA as easy to park in, dog-friendly, and well-kept. Most residents say you need a car. See recently sold homes in Sturbridge, MA.
  • Does 21 McGregory Rd have air conditioning?
    Yes, 21 McGregory Rd in Sturbridge, MA has air conditioning.
  • Does 21 McGregory Rd have laundry facilities?
    Yes, 21 McGregory Rd in Sturbridge, MA has laundry facilities.

Explore by feature - Air Conditioning

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Off Market Homes Near 21 McGregory Rd

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