Active
101 Days on market
243 Upland Ave Newton — Photo 1 of 40
Recent Drop: $150,001
$2,150,000$1,999,999
$1,999,999
243 Upland Ave, Newton, MA 02461
Newton, MA 02461 — Newton Highlands
Beds
4
Baths
4
SqFt
3,847
Style
Single Family
Built
1914
This is a rare opportunity atop one of Newton’s most coveted hilltop locations. Winner of the Newton Beautification Award and featured in a local design magazine, this original farmhouse—held by fewer than five owners—blends timeless character with thoughtful modern updates and exceptional future potential. Surrounded by $5–$6.5M homes, the setting is truly premier. The residence offers 4 bedrooms, 3 full baths, and 2 half baths, including two fully renovated designer baths featuring a slipper tub and Italian marble vanity. The chef’s kitchen boasts a Sub-Zero refrigerator, chefs 6-burner gas convection range with center griddle, wine fridge, and powered skylight. Enjoy two level deck, three wood-burning fireplaces plus a gas fireplace. The grand primary suite includes a spa-like bath, large walk-in closet +Accessory room. Updates throughout preserve historic charm while providing modern comfort, including a new architectural shingle roof. In-law or home office suite potential.
Immersive Experience
Market Value Analysis
This Property
Size (SqFt) →Price →This Property$520/sqft
Local Avg (Newton)$560/sqft
7% BelowMarket Average
* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Newton, MA.
Property Details
Financials
Original Price$2,150,000
Annual Taxes$15,477
Parking
Garage2
Off-Street7
Interior Specifications
Total Rooms10
Fireplaces4
FlooringTile, Hardwood
BasementFull, Partially Finished, Walk-Out Access
Climate & Utilities
HeatingCentral, Forced Air, Natural Gas
CoolingCentral Air
WaterPublic
SewerPublic Sewer
Building & Exterior
ConstructionFrame
RoofShingle, Rubber
FoundationConcrete Perimeter
ZoningSR2
Property & Lot
Acres0.6
SqFt Lot26,250
Lot FeaturesWooded, Level, Sloped
Amenities & Appliances
Gas Water Heater • Range • Dishwasher • Disposal • Trash Compactor • Refrigerator • Freezer • Washer • Dryer
Neighborhood
Public Transportation • Shopping • Tennis Court(s) • Park • Walk/Jog Trails • Golf
Geography
Floorplan Breakdown
Structural Layout
Second
Master BedroomBedroom 2Bedroom 3
Main,First
Living RoomDining RoomKitchenFamily Room
Living Room
Lvl Main,First13 x 22.916666666
Flooring - Hardwood, Window(s) - Bay/Bow/Box, Open Floorplan, Recessed Lighting, Lighting - Sconce, Breezeway
Dining Room
Lvl Main,First13 x 12
Wood / Coal / Pellet Stove, Flooring - Hardwood, Lighting - Pendant, Decorative Molding
Kitchen
Lvl Main,First13.666666666 x 18.333333333
Skylight, Balcony / Deck, Kitchen Island, Wet Bar, Cabinets - Upgraded, Cable Hookup, Deck - Exterior, Exterior Access, High Speed Internet Hookup, Recessed Lighting, Remodeled, Stainless Steel Appliances, Wine Chiller, Gas Stove, Lighting - Pendant, Crown Molding, Decorative Molding, Flooring - Engineered Hardwood
Family Room
Lvl Main,First13 x 17
Flooring - Laminate, Balcony / Deck, High Speed Internet Hookup, Recessed Lighting
Master Bedroom
Lvl Second13 x 21.583333333
Wood / Coal / Pellet Stove, Skylight, Ceiling Fan(s), Walk-In Closet(s), Flooring - Hardwood, Window(s) - Bay/Bow/Box, Hot Tub / Spa, Cable Hookup, High Speed Internet Hookup, Recessed Lighting, Remodeled, Closet - Double
Bedroom 2
Lvl Second13 x 10.583333333
Bedroom 3
Lvl Second13 x 11.25
Ceiling Fan(s), Flooring - Wall to Wall Carpet, Decorative Molding
Property History
Price Drop
$1,999,999
Was $2,050,000
Jul 23, 2026
MLS® 73516643
Price Drop
$2,050,000
Was $2,099,888
Jul 16, 2026
MLS® 73516643
Price Drop
$2,099,888
Was $2,100,000
Jun 24, 2026
MLS® 73516643
Listed
$10,000
Jun 12, 2026
MLS® 73535311
Price Drop
$2,100,000
Was $2,150,000
Jun 9, 2026
MLS® 73516643
Listed
$1,999,999
Jun 9, 2026
MLS® 73532809
Listed
$2,150,000
May 12, 2026
MLS® 73516643
Terminated
$2,200,000
May 6, 2026
MLS® 73488294
Listed
$2,200,000
Mar 18, 2026
MLS® 73488294
Population
6,975
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
Median Household Income
$224K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
Renter-Occupied Homes
23.8%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
New Construction Permits — Middlesex County
2,667 housing units permitted in the last 12 months (-2% vs the prior 12 months) — 1,709 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jun '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 3,847 sq ft principal dwelling). Lot size: 26,250 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 Provided By
Listing Agent: Adam Kotkin
Listing Office: Red Tree Real Estate
MLS® Number: 73516643
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