FeaturesFlooring - Hardwood, Pantry, Countertops - Stone/Granite/Solid, Kitchen Island, Open Floorplan, Recessed Lighting
LevelMain,First
27 Hillside Dr, Sturbridge MA 01566
Sturbridge, MA 01566 • Shepard Hills Neighborhood
$479,900
Est. $3,192/month
Estimate assumptions
20% down, a 30-year loan at 6.5%, and $200/month estimated insurance.
Includes the supplied property-tax and HOA inputs; missing inputs contribute $0. HOA fees with an unspecified frequency are treated as monthly. PMI and closing costs are excluded.
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Open House Schedule
27
Sep
Sunday, September 27
12:00 PM - 2:00 PM EDT
26
Sep
Saturday, September 26
11:00 AM - 1:00 PM EDT
About this home
Check out this gorgeous large sunny back yard with inviting IG pool! Welcome home to this spacious 3 BR 2 BA Home located in the desirable Hillside Drive Neighborhood! Situated on a quiet cul-de-sac street, this home offers a convenient location for commuters while being just minutes to shopping, dining and everyday amenities. The spacious main living level features all hardwood flooring and an inviting open-concept layout, for the Living Rm, Dining Area and Kitchen with a center island-perfect for entertaining. The Primary BR enjoys direct access to the recently renovated full Bath, while 2 additional Bedrooms complete this floor. The finished lower level offers additional living area with a Family Rm, and the 2nd Full Bath, ideal for guests, at home office or recreation area. Double French Doors from the main living area lead to an expansive 14 x 24 Deck overlooking the amazing level backyard. Additional highlights include a fire pit, brick walkway & a 2 car garage.
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Recently Sold Nearby
Property History
Market Insights
Property Timeline
Back On Market
Sep 21, 2026
Active
Pending Sale
Jul 4, 2026
Offer accepted, sale pending
Listed for Sale
Jun 26, 2026
$479,900
Original listing
Agent: Lorraine Herbert
Office: RE/MAX Prof Associates
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 09/21/2026 | • Back On Market | - | - | - | Active |
| 07/04/2026 | ⏳ Pending Sale | - | - | - | Offer accepted, sale pending |
| 06/26/2026 | 🏠 Listed for Sale | $479,900 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2026 | $6,788 | $435,100 |
Financial Details
Annual Property Tax
$6,788
Tax Year 2026
Assessed Value
$435,100
Facts & Features
2 Car Garage
Home Facts
Type
Residential
Style
Single Family Residence
Year Built
1970
Living Area
2,209 sq ft
Lot Size
0.95 acres
Bedrooms
3
Full Baths
2
Total Rooms
7
Interior
Heating
Electric Baseboard, Electric
Cooling
Window Unit(s)
Flooring
Wood, Tile, Carpet, Hardwood
Appliances
Electric Water Heater, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer
Fireplace
Family Room, Living Room
Fireplaces
2
Basement
Finished, Walk-out Access, Interior Entry, Garage Access, Concrete
Laundry
In Basement, Electric Dryer Hookup, Washer Hookup
Features
Central Vacuum
Exterior
Construction
Frame
Architecture
Split Entry
Roof
Shingle
Features
Deck, Pool - Inground, Rain Gutters, Screens
Pool
In Ground
Spa
None
Fencing
None
Patio/Porch
Deck
Parking
Garage Spaces
2
Has Garage
Yes
Features
Under, Garage Door Opener, Paved Drive, Off Street, Paved
Total Spaces
8
Utilities
Electric
Circuit Breakers
Water
Private
Sewer
Private Sewer
Gas
None
Other
For Electric Range, For Electric Dryer, Washer Hookup
Financial
Annual Tax
$6,788
Assessed Value
$435,100
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
Down Payment Resource
Eligible
MA Disclosures
Lead Paint
Unknown
Seller Disclosures
All Offers Subject To Complete Release Of First Buyer. Riding Lawn Mower, All Pool Equipment Inc 2 Robotic Cleaners, 3 Window Ac Units, Window Treatments Stay. No Buyer Letters, Depositlink For All Deposits. Both Pellet Stove Inserts Are Nonfunctional.
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
House Color
brick/bge
Sq Ft Source
Public Record
Sq Ft Disclosures
Includes finished LL with full Bath
Documents
None
County
Worcester
Total market time (incl. prior listings)
8 days
Property Overview
Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1970
Bedrooms
3
Full Bathrooms
2
Living Area
2,209 sq ft
Total Rooms
7
Floor Layout
Interactive room guide
Floor Layout
Finished Area
1,397 sq ft above grade
812 sq ft below grade
FeaturesCloset, Flooring - Hardwood
LevelFirst
FeaturesCloset, Flooring - Hardwood
LevelFirst
FeaturesBathroom - Full, Closet - Linen, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Remodeled
LevelMain,First
FeaturesFlooring - Hardwood, French Doors, Deck - Exterior, Exterior Access, Open Floorplan
LevelMain,First
FeaturesFlooring - Hardwood, Window(s) - Bay/Bow/Box, Open Floorplan, Recessed Lighting
LevelMain,First
FeaturesBathroom - Full, Cedar Closet(s), Closet, Flooring - Hardwood
LevelFirst
FeaturesBathroom - Full, Flooring - Stone/Ceramic Tile, Countertops - Upgraded
LevelBasement
FeaturesBathroom - Full, Flooring - Wall to Wall Carpet
LevelBasement
Display Options
Outdoor Areas
PoolIn Ground
Patio & porchDeck
Room Markers
OOffice (1)
KKitchen (1)
BRBedroom (5)
BABathroom (4)
DDining (1)
LLiving (2)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Wood, Tile, Carpet, Hardwood
Appliances:
Electric Water Heater, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer
Interior Features:
Central Vacuum
Windows:
Insulated Windows, Screens
Basement:
Finished, Walk-Out Access, Interior Entry, Garage Access, Concrete
Laundry:
In Basement, Electric Dryer Hookup, Washer Hookup
Security:
Construction & Materials
Style:
Split Entry
Year Built:
1970
Structure Type:
Exterior Materials:
Frame
Roof:
Shingle
Foundation:
Concrete Perimeter
Heating, Cooling & Utilities
Heating:
Electric Baseboard, Electric
Cooling:
Window Unit(s)
Hot Water:
Water Source:
Private
Sewer:
Private Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Deck, Pool - Inground, Rain Gutters, Screens
Patio & Porch:
Deck
Fencing:
Other Structures:
Lot Features:
Cul-De-Sac, Cleared
Road Frontage:
150.00 ft
Road Surface:
Paved
Parking & Garage
Garage Spaces:
2
Garage Type:
Attached
Total Parking Spaces:
8
Parking Features:
Under, Garage Door Opener, Paved Drive, Off Street, Paved
Special Features
Fireplaces:
2
Fireplace Type:
Family Room, Living Room
Pool:
Private Pool
Pool Features:
In Ground
Community Amenities:
Nearby Schools
School District
Sturbridge School District local
B
School Safety
2024-25
0.0%
Very Low (Safest)
5.5% below state avg
Elementary Schools
3 schools
C-
West Street School
1.2 mi
|
#719 of 825
|
Score: 34.5
Improved 23 spots from last year
-23.7 below state avg
324 students
Moderate
Rising School
Grades 01-05
Trinity Catholic Academy
1.9 mi
Grades PK-08
Eastford Road School
1.9 mi
368 students
Diverse
Grades PK-01
Middle Schools
2 schools
C
Southbridge Middle School
3.5 mi
|
#283 of 352
|
Score: 33.2
Same rank as last year
-25 below state avg
398 students
Diverse
Grades 06-08
B+
Tantasqua Regional Junior High School
4.0 mi
|
#142 of 352
|
Score: 45.1
Dropped 9 spots from last year
-13.1 below state avg
528 students
Less Diverse
Grades 07-08
High Schools
2 schools
Southbridge Academy
1.7 mi
22 students
Diverse
Grades 06-12
D
Southbridge High School
3.5 mi
|
#316 of 346
|
Score: 35.1
Improved 16 spots from last year
-23.1 below state avg
404 students
Moderate
12 sports
• 498 athletes
Early College Program
College Ready Curriculum
Grades 09-12
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Monthly Payment Breakdown
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Property Tax
$566
Homeowners Insurance
$200
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Loan Summary
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Payment Over Time
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
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Location
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Neighborhood
Shepard Hills Neighborhood
27 Hillside Dr, Sturbridge MA 01566
Sturbridge, MA 01566
Listing Information
Listing Agent
Lorraine Herbert
Listing Office
RE/MAX Prof Associates
Office Phone
508-347-9595
Agent MLS ID
K0001572
Office MLS ID
K01527
Listing Data Updated
Sep 21, 2026 12:06 PM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
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