107 Old School House Rd Oakham — Photo 1 of 42
Recent Drop: $50,000
$749,900
107 Old School House Rd, Oakham, MA 01068
Oakham, MA 01068 — Longview Estates
Beds
5
Baths
3.5
SqFt
3,165
Style
Single Family
Built
2006
Warm, welcoming & beautifully cared for, this Longview Estates Colonial offers space, flexibility & possibilities! Set on 5.4 private acres in an established neighborhood, this approx. 3,165 sq ft home features 5 bedrooms & 3.5 baths. The main home offers hardwood floors, an inviting kitchen with breakfast bar, dining nook & charming window seat, plus flexible upstairs space for an office, media room or playroom. A standout feature is the spacious first-floor 2-bedroom second living area with its own kitchen, full bath, laundry, cathedral ceilings, skylights & private deck—ideal for multigenerational living, extended family, adult children or potential rental income to help offset the mortgage. Beautiful backyard, 2-car garage, 2x6 construction, irrigation, generator-ready setup & Buderus heating. One property with so many ways to make it work for you!
Key facts
It was listed on August 26, 2026. The price has come down from an original $799,900 to $749,900, most recently on September 17, 2026. The annual property taxes are $7,287 (2025 tax year). It sits on a 5.4-acre (235,224 sq ft) lot.
Market Value Analysis
* Analysis is based on 9 actively listed and recently sold comparable properties strictly within Oakham, MA.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Water Heater • Tankless Water Heater • Range • Dishwasher • Microwave • Refrigerator • Freezer • Washer • Dryer • Water Treatment
Neighborhood
Walk/Jog Trails • Stable(s) • Golf • Medical Facility • Conservation Area • House of Worship
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl FirstWood / Coal / Pellet Stove, Flooring - Hardwood, Deck - Exterior
Dining Room
Lvl FirstFlooring - Hardwood, Chair Rail
Kitchen
Lvl FirstFlooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Breakfast Bar / Nook, Recessed Lighting, Window Seat
Primary Bedroom
Lvl SecondBathroom - Full, Walk-In Closet(s), Flooring - Wall to Wall Carpet
Bedroom 2
Lvl SecondBedroom 3
Lvl SecondFlooring - Wall to Wall Carpet
Bathroom 1
Lvl FirstBathroom - Half, Flooring - Stone/Ceramic Tile
Bathroom 2
Lvl SecondBathroom - Full, Flooring - Stone/Ceramic Tile
Bathroom 3
Lvl SecondBathroom - Full, Flooring - Stone/Ceramic Tile
Property History
$749,900
Was $799,900
Sep 17, 2026
MLS® 73568386
$799,900
Aug 26, 2026
MLS® 73568386
Questions about this home
When was 107 Old School House Rd, Oakham listed?
107 Old School House Rd, Oakham was listed on August 26, 2026.
Has the price of 107 Old School House Rd, Oakham changed?
The price has come down from an original $799,900 to $749,900, most recently on September 17, 2026.
What are the property taxes for 107 Old School House Rd, Oakham?
The annual property taxes for 107 Old School House Rd, Oakham are $7,287 (2025 tax year).
How big is the lot at 107 Old School House Rd, Oakham?
107 Old School House Rd, Oakham sits on a 5.4-acre (235,224 sq ft) lot.
What is the status of 107 Old School House Rd, Oakham?
107 Old School House Rd, Oakham is actively listed for sale.
Population
1,639
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
Median Household Income
$102K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
Renter-Occupied Homes
8.4%
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 3,165 sq ft principal dwelling). Lot size: 235,224 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: Worcester County Homes Team
Listing Office: RE/MAX Vision
MLS® Number: 73568386
