21 McGregory Rd, Sturbridge, MA 01566
OFF MARKET

21 McGregory Rd
Sturbridge, MA 01566

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

$597,000

Trulia Estimate
as of Jun 8, 2026
Est. Refi. Payment $3,729/mo*
Refinance Your Home

$597,000

Trulia Estimate
as of Jun 8, 2026
Est. Refi. Payment $3,729/mo*
Refinance Your Home
3 Beds
1.5 Baths
2,210 sqft
(on 0.65 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from May 01, 2025

Home Highlights

Parking
2 Car Garage
Outdoor
Porch, Patio, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
138 days ago

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
Last check for updates: about 2 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

Price History for 21 McGregory Rd

DatePriceEventSource
04/23/2025$585,000Sold
MLS PIN #73350067
03/31/2025$539,900Listed For SaleMLS PIN #73350067

Market trends in Sturbridge

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
32
7MoM
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Property Tax and Assessment

Year2025
Tax$7,196
Assessment$451,700
Home facts updated by county records

Comparable Sales for 21 McGregory Rd

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
3 Gedeon Ave, Sturbridge, MA
0.27
Single-Family Home
$425,000
07/09/25
4
2
1,980
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
6 McGilpin Rd, Sturbridge, MA
0.63
Single-Family Home
$393,000
12/04/25
3
2.5
1,888
6 Hillside Dr, Sturbridge, MA
1.00
Single-Family Home
$555,000
10/29/25
3
2
2,263

Nearby homes

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Assigned Schools

These are the assigned schools for 21 McGregory 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.

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
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  • Jfgannon1
    "Friendly families. Cup d sac. Well maintained yards. Rural. Wildlife abounds. Children in the neighborhood."
    0
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  • Elizabethlouisepotter
    "There’s a dance studio and a paint-and-sip. The school district is competitive and well-run. Great commuter town."
    0
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  • 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
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  • 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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Homes for sale near 21 McGregory Rd

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Off Market Homes Near 21 McGregory Rd

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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.

Homes for rent near 21 McGregory Rd

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21 McGregory Rd, Sturbridge, MA 01566 is a 3 bedroom, 2 bathroom, 2,210 sqft single-family home built in 1955. This property is not currently available for sale. 21 McGregory Rd was last sold on Apr 23, 2025 for $585,000 (8% higher than the asking price of $539,900). The current Trulia Estimate for 21 McGregory Rd is $597,000.