Active
26 Days on market
165 East St Upton — Photo 1 of 40

165 East St Upton — Photo 1 of 40

$1,079,000

165 East St, Upton, MA 01568

Upton, MA 01568

Beds

4

Baths

3.5

SqFt

3,350

Style

Single Family

Built

1986

Pride of ownership abounds at this exceptional 4-bedroom, 3.5 bath custom contemporary home set on 3.50 beautifully maintained acres offering privacy and endless opportunities to enjoy the outdoors. Enter through the two-story foyer and be greeted by sunlight pouring into the home through an abundance of windows, skylights, and sliders creating a bright and welcoming atmosphere throughout. The kitchen includes two pantry closets, Sub Zero refrigerator and stylish concrete sink and flows to a step-down dining/living area with gorgeous stone fireplace and slider access to the peaceful screened in porch and amazing deck. A laundry room, half bath and vaulted ceiling living room with French doors complete the floor. Upstairs a large bedroom with en-suite bath acts as a second primary and is complemented by two additional bedrooms and full bath on the way to the huge primary bedroom with vaulted ceilings, double closets, a separate room currently being used as a makeup area and an exquisite bathroom with jetted tub and separate shower. The walk out lower level includes a climate controlled wine cellar and access to the heated two car garage. Outdoor living is truly a highlight, with a beautiful stone patio featuring a pizza oven, pergola and a fire pit, plus a deck with newer composite decking and railings and high end built-in grill and additional pergola—perfect for entertaining, dining, or relaxing. Additional features include a new roof with solar panels, a beautifully repaved driveway with a distinctive paver border, and lushly landscaped grounds. With its combination of generous living space, unique amenities, and spectacular indoor-outdoor living, this Upton property offers a rare opportunity to enjoy comfort, in a serene environment yet only a short distance to Routes 495 and 90 and the shops and restaurants nearby.

Key facts

It was listed on September 9, 2026. The annual property taxes are $10,770 (2025 tax year). It sits on a 3.5-acre (152,460 sq ft) lot.

Immersive Experience

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$322/sqft
Local Avg (Upton)$319/sqft
1% AboveMarket Average

* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Upton, MA.

Property Details

Financials

Original Price$1,079,000
Annual Taxes$10,770

Parking

Garage2
Off-Street8

Interior Specifications

Total Rooms9
Fireplaces1
FlooringTile, Carpet, Hardwood, Flooring - Hardwood, Flooring - Stone/Ceramic Tile
BasementFull, Partially Finished, Interior Entry

Climate & Utilities

HeatingBaseboard, Oil
CoolingCentral Air
WaterPrivate
SewerPrivate Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationConcrete Perimeter, Irregular
Zoning5

Property & Lot

Acres3.5
SqFt Lot152,460
Lot FeaturesWooded, Gentle Sloping

Amenities & Appliances

Water Heater • Range • Dishwasher • Microwave • Refrigerator • Plumbed For Ice Maker

Neighborhood

Walk/Jog Trails • Highway Access • Public School

Geography

Floorplan Breakdown

Structural Layout

Second
Primary BedroomBedroom 2Bedroom 3Bedroom 4Bathroom 2Bathroom 3
Main,First
Living RoomDining RoomKitchenFamily RoomBathroom 1
Main
Office
Living Room
Lvl Main,First

13.25 x 15.333333333

Skylight, Vaulted Ceiling(s), Flooring - Hardwood, French Doors

Dining Room
Lvl Main,First

14 x 19

Ceiling Fan(s), Flooring - Hardwood, Deck - Exterior, Slider, Lighting - Overhead

Kitchen
Lvl Main,First

23 x 9.25

Flooring - Hardwood, Dining Area, Pantry, Countertops - Stone/Granite/Solid, Breakfast Bar / Nook, Recessed Lighting, Stainless Steel Appliances, Peninsula

Office
Lvl Main

13.25 x 11.166666666

Flooring - Hardwood, Deck - Exterior, Slider, Lighting - Overhead

Family Room
Lvl Main,First

14.416666666 x 21

Ceiling Fan(s), Flooring - Hardwood, Recessed Lighting, Lighting - Overhead

Primary Bedroom
Lvl Second

28 x 22.083333333

Bathroom - Full, Ceiling Fan(s), Vaulted Ceiling(s), Walk-In Closet(s), Flooring - Hardwood, Dressing Room, Recessed Lighting, Lighting - Overhead, Closet - Double

Bedroom 2
Lvl Second

9.916666666 x 10

Bedroom 3
Lvl Second

11.416666666 x 11.333333333

Ceiling Fan(s), Closet, Flooring - Hardwood, Lighting - Overhead

Bedroom 4
Lvl Second

14.916666666 x 14.666666666

Bathroom - Full, Skylight, Ceiling Fan(s), Vaulted Ceiling(s), Closet, Flooring - Hardwood, Lighting - Overhead

Bathroom 1
Lvl Main,First

7.416666666 x 4.916666666

Bathroom - Half, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Lighting - Overhead

Bathroom 2
Lvl Second

11 x 8

Bathroom - Full, Bathroom - With Shower Stall, Bathroom - With Tub, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Lighting - Overhead

Bathroom 3
Lvl Second

7.916666666 x 10

Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - With Tub & Shower, Flooring - Stone/Ceramic Tile, Lighting - Overhead

Questions about this home

When was 165 East St, Upton listed?

165 East St, Upton was listed on September 9, 2026.

Has the price of 165 East St, Upton changed?

The price hasn't changed since it was listed at $1,079,000.

What are the property taxes for 165 East St, Upton?

The annual property taxes for 165 East St, Upton are $10,770 (2025 tax year).

How big is the lot at 165 East St, Upton?

165 East St, Upton sits on a 3.5-acre (152,460 sq ft) lot.

What is the status of 165 East St, Upton?

165 East St, Upton is actively listed for sale.

Population

8,011

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$160K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

13.7%

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 3,350 sq ft principal dwelling). Lot size: 152,460 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: Michael Stein

Listing Office: Redfin Corp.

MLS® Number: 73574514