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243 Upland AveNewton, MA 02461

For Sale

$2,200,000

Smart Buyer Rebate $11,000

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. Numerous updates throughout preserve historic charm while providing modern comfort, including a new architectural shingle roof. In-law or home office suite potential

Listed by Adam Kotkin

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Red Tree Real Estate

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617-694-7356

Listed by Maxim Rosenberg

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Red Tree Real Estate

Listed by Daniel Bedjanov

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Red Tree Real Estate

Last updated April 27, 2026

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Source: MLSPin #73488294

Listing Facts

  • TypeSingle-family
  • NeighborhoodNewton Highlands
  • Bedrooms4
  • Bathrooms5
  • Days on Prevu44
  • Taxes$15,477/year
  • Size3,847 sqft
  • Price per sqft$572

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Washer/Dryer
  • Air Conditioning
  • Parking

Location

Mortgage Calculator

Listing History

04/27/2026
Price Decreased
$2,200,000
04/14/2026
Price Decreased
$2,250,000
03/31/2026
Price Decreased
$2,350,000
03/18/2026
Listed by Red Tree Real Estate
$2,500,000

Property Details for 243 Upland Ave

Association

Amenities

  • Community Features: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, House Of Worship, Private School, Public School, T-Station

Exterior

Construction

  • Roof: Shingle, Rubber
  • Window Features: Insulated Windows
  • Year Built: 1914
  • Year Built Details: Actual
  • Architectural Style: Colonial
  • Construction Materials: Frame
  • Exterior Features: Porch - Enclosed, Deck - Wood, Rain Gutters, Storage, Fenced Yard

Features

  • Fencing: Fenced
  • Patio And Porch Features: Porch - Enclosed, Deck - Wood
  • Road Frontage Type: Public, Private Road

Measurements

  • Building Area Total: 3,847
  • Building Area Units: Square Feet
  • Lot Features: Wooded, Level, Sloped
  • Lot Size Acres: 0.60
  • Lot Size Area: 0
  • Lot Size Square Feet: 26,250
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: S:83 B:027 L:0027,707518
  • Tax Annual Amount: $15,477.00
  • Tax Assessed Value: $1,579,300.00
  • Tax Year: 2025

Interior

Features

  • Appliances: Gas Water Heater, Range, Dishwasher, Disposal, Trash Compactor, Refrigerator, Freezer, Washer, Dryer
  • Fireplace Features: Dining Room, Kitchen, Living Room, Master Bedroom
  • Fireplace: Yes
  • Fireplaces Total: 4
  • Flooring: Tile, Hardwood

Measurements

  • Living Area: 3,847
  • Living Area Source: Measured

Rooms

  • Basement: Full, Partially Finished, Walk-Out Access
  • Bathrooms Full: 3
  • Bathrooms Half: 2
  • Bathrooms Total Integer: 5
  • Bedrooms Total: 4
  • Rooms Total: 10

Parking

Parking

  • Attached Garage: Yes
  • Covered Spaces: 2
  • Garage Spaces: 2
  • Garage: Yes
  • Open Parking Spaces: 5
  • Open Parking: Yes
  • Parking Features: Attached, Paved Drive, Off Street
  • Parking Total: 7

Schools

Elementary School

  • Elementary School: Countryside

High School

  • High School: Newton South

Middle or Junior School

  • Middle Or Junior School: Brown

Utilities

Equipment

  • Cooling: Central Air
  • Has Cooling: Yes
  • Heating: Central, Forced Air, Natural Gas
  • Has Heating: Yes
  • Laundry Features: Closet - Linen, Flooring - Stone/Ceramic Tile, Main Level, First Floor
  • Sewer: Public Sewer
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 4 bedrooms and 5 bathrooms in this single-family home at 243 Upland Ave.

What schools are nearby to 243 Upland Ave?

Nearby schools include the Countryside Elementary School, Brown Middle School, and Newton South High School.

Does this single-family home have parking?

Yes, there are 2 parking spaces available for 243 Upland Ave.

What are the annual taxes for 243 Upland Ave?

Annual taxes for this single-family home are estimated at $15,477.

How does 243 Upland Ave compare to other single-family homes in Newton Highlands?

This single-family home is listed 7% below the average price for single-family homes in Newton Highlands and has been on the market for 1 less day than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 3,847 sqft.

243 Upland Ave is a 4-bedroom, 5-bath single-family home for sale in Newton MA 02461. On Prevu for 44 days at $2,200,000. This includes a recent price decrease of $50,000. This residence features 3,847 square feet of living space, located in Newton Highlands. The median listing price for single-family homes in this area is $1,699,000. Nearby schools include Countryside Elementary School, Brown Middle School, and Newton South High School. Additional amenities include private outdoor space, dishwasher, air conditioning, parking, and washer/dryer. Browse more single-family home listings in Newton.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.