FeaturesBathroom - Full, Closet - Linen, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Remodeled
LevelMain,First
27 Hillside Dr, Sturbridge MA 01566
Sturbridge, MA 01566 • Shepard Hills Neighborhood
$479,900
Est. $3,192/month
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About this home
Pool Opening Soon! 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 main living level features all hardwood flooring and an inviting open-concept layout, including the FPLD Living Rm, with cozy pellet stove insert, 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, also with pellet stove, 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 large, sunny backyard and IG pool! 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
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 |
|---|---|---|---|---|---|
| 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, Pellet Stove
Cooling
Window Unit(s)
Flooring
Wood, Tile, Carpet, Hardwood
Appliances
Electric Water Heater, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer, Vacuum System
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, Fenced Yard
Pool
In Ground
Spa
None
Fencing
Fenced
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
Seller Disclosures
Pool Opening Soon, 2025 Pool Photo. Riding Lawn Mower, All Pool Equipment Inc 2 Robotic Cleaners, 3 Window Ac Units, Window Treatments Stay. Sellers Have Not Used The Bsmt Pellet Stove Insert. Title V Inspection Is Scheduled. No Buyer Letters, Depositlink For All Deposits.
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
Sale Pending
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
FeaturesFlooring - Hardwood, French Doors, Deck - Exterior, Exterior Access, Open Floorplan
LevelMain,First
FeaturesFlooring - Hardwood, Pantry, Countertops - Stone/Granite/Solid, Kitchen Island, Open Floorplan, Recessed Lighting
LevelMain,First
FeaturesCloset, Flooring - Hardwood
LevelFirst
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
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
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, Vacuum System
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, Pellet Stove
Cooling:
Window Unit(s)
Hot Water:
Water Source:
Private
Sewer:
Private Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Deck, Pool - Inground, Rain Gutters, Screens, Fenced Yard
Patio & Porch:
Deck
Fencing:
Fenced
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
|
#724 of 824
|
Score: 34.0
Improved 18 spots from last year
-24.2 below state avg
323 students
Moderate
Grades 01-05
Trinity Catholic Academy
1.9 mi
Grades PK-08
Eastford Road School
1.9 mi
397 students
Moderate
Grades PK-01
Middle Schools
2 schools
C
Southbridge Middle School
3.5 mi
|
#282 of 352
|
Score: 33.3
Improved 1 spots from last year
-24.9 below state avg
380 students
Diverse
Grades 06-08
B+
Tantasqua Regional Junior High School
4.0 mi
|
#143 of 352
|
Score: 44.9
Dropped 10 spots from last year
-13.3 below state avg
576 students
Less Diverse
Grades 07-08
High Schools
2 schools
Southbridge Academy
1.7 mi
21 students
Diverse
Grades 06-12
C-
Southbridge High School
3.5 mi
|
#310 of 346
|
Score: 35.8
Improved 22 spots from last year
-22.5 below state avg
419 students
Moderate
12 sports
• 498 athletes
Early College Program
Rising School
College Ready Curriculum
Grades 09-12
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95% Interest
Year 15
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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
Jul 7, 2026 3:30 AM 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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