50 Hillside Dr Sturbridge — Photo 1 of 41
Recent Drop: $25,000
$1,075,000
50 Hillside Dr, Sturbridge, MA 01566
Sturbridge, MA 01566
Beds
4
Baths
2.5
SqFt
2,688
Style
Single Family
Built
2025
Behind a quiet cul-de-sac lies a custom-built retreat where luxury & nature exist in perfect balance! Built in 2025 & set on 26.8 private acres, this exceptional home blends refined craftsmanship w/ modern design. An open-concept layout features a chef's kitchen w/ custom cabinetry, quartzite countertops,14x6 island, walk-in pantry, & seamless flow into the living & dining area. The luxurious primary suite offers dual walk-in closets & a spa-inspired bath w/ an oversized wet room & soaking tub, complemented by three spacious bedrooms. Enjoy a 900+ sq. ft. deck, Alaskan white cedar porch, and an impressive 8-car garage w/ a 14-foot RV bay & 20-foot ceilings. Built with SIP construction, sound-insulated walls, dual-zone HVAC, & Super Stretch Code standards, this home delivers exceptional comfort & efficiency. Surrounded by protected woodland w/ direct access to the Grand Trunk Trail & easy access to Rt. 84 & the Mass Pike, this custom estate offers a truly exceptional living experience!
Key facts
It was listed on July 20, 2026. The price has come down from an original $1,100,000 to $1,075,000, most recently on September 1, 2026. The annual property taxes are $16,077 (2026 tax year). It sits on a 26.8-acre (1,167,582 sq ft) lot.
Market Value Analysis
* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Sturbridge, MA.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Water Heater • Range • Dishwasher • Disposal • Refrigerator
Neighborhood
Walk/Jog Trails • Medical Facility • Highway Access • House of Worship
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl Main,First26 x 16
Ceiling Fan(s), Flooring - Vinyl, Open Floorplan, Recessed Lighting
Dining Room
Lvl Main,First16 x 15
Flooring - Vinyl, Lighting - Pendant
Kitchen
Lvl Main,First22 x 14
Closet/Cabinets - Custom Built, Flooring - Vinyl, Dining Area, Pantry, Countertops - Upgraded, Kitchen Island, Open Floorplan, Recessed Lighting, Lighting - Pendant
Primary Bedroom
Lvl Second14 x 12
Bathroom - Full, Bathroom - Double Vanity/Sink, Ceiling Fan(s), Flooring - Wall to Wall Carpet, Closet - Double
Bedroom 2
Lvl Second12 x 12
Bedroom 3
Lvl Second12 x 10
Ceiling Fan(s), Flooring - Wall to Wall Carpet, Closet - Double
Bedroom 4
Lvl Second11 x 10
Ceiling Fan(s), Closet, Flooring - Wall to Wall Carpet
Bathroom 1
Lvl First8 x 7
Bathroom - Half, Flooring - Vinyl
Bathroom 2
Lvl Second23 x 10
Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - With Tub & Shower, Flooring - Vinyl
Bathroom 3
Lvl Second13 x 7
Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - With Tub & Shower, Flooring - Vinyl
Property History
$1,075,000
Was $1,100,000
Sep 1, 2026
MLS® 73552284
$1,100,000
Jul 20, 2026
MLS® 73552284
Questions about this home
When was 50 Hillside Dr, Sturbridge listed?
50 Hillside Dr, Sturbridge was listed on July 20, 2026.
Has the price of 50 Hillside Dr, Sturbridge changed?
The price has come down from an original $1,100,000 to $1,075,000, most recently on September 1, 2026.
What are the property taxes for 50 Hillside Dr, Sturbridge?
The annual property taxes for 50 Hillside Dr, Sturbridge are $16,077 (2026 tax year).
How big is the lot at 50 Hillside Dr, Sturbridge?
50 Hillside Dr, Sturbridge sits on a 26.8-acre (1,167,582 sq ft) lot.
What is the status of 50 Hillside Dr, Sturbridge?
50 Hillside Dr, Sturbridge is actively listed for sale.
Population
7,362
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
Median Household Income
$138K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
Renter-Occupied Homes
7.7%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
New Construction Permits — Worcester County
1,805 housing units permitted in the last 12 months (+1% vs the prior 12 months) — 1,007 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jul '26)
ADU Potential
Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 2,688 sq ft principal dwelling). Lot size: 1,167,582 sq ft.
Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.
Listing Agent: Jim Black Group
Listing Office: Real Broker MA, LLC
MLS® Number: 73552284
