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Gundersheim Group Real Estate

© 2026 Melanie Gundersheim. All rights reserved.
Equal Housing Opportunity. Information deemed reliable but not guaranteed.

  1. Home
  2. Listings
  3. 38 Upwey Rd, Wellesley, MA 02481
Active
43 Days on market
38 Upwey Rd Wellesley — Photo 1 of 42

38 Upwey Rd Wellesley — Photo 1 of 42

Recent Drop: $54,000

$2,349,000
$2,295,000

$2,295,000

38 Upwey Rd, Wellesley, MA 02481

Wellesley, MA 02481

Beds

4

Baths

3.5

SqFt

3,776

Style

Single Family

Built

1993

Welcome to 38 Upwey Road, offering generous living space, a flexible floor plan and an unbeatable Wellesley location. Built in 1993, this 4-bedroom, 3.5 bath home offers three finished levels, an oversized 2-car garage and a bright, open-concept floor plan. Newly refreshed, the kitchen features brand-new countertops and appliances, while recent roof and system updates offer added peace of mind. A dedicated home office provides the perfect work-from-home space. The walk-out lower level adds tremendous versatility with a spacious recreation area, full bath and wine storage room. Enjoy a private backyard while being just moments from Linden Square, Wellesley’s commuter rail, schools and major commuting routes. A wonderful opportunity to enjoy space, convenience and a prime Wellesley location.

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$608/sqft
Local Avg (Wellesley)$670/sqft
9% BelowMarket Average

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

Property Details

Financials

Original Price$2,349,000
Annual Taxes$19,193

Parking

Garage2
Off-Street6

Interior Specifications

Total Rooms9
Fireplaces2
Flooring--
BasementPartial, Finished

Climate & Utilities

HeatingForced Air, Natural Gas
CoolingCentral Air
WaterPublic
SewerPublic Sewer

Building & Exterior

Construction--
Roof--
FoundationConcrete Perimeter
ZoningSR10

Property & Lot

Acres0.31
SqFt Lot13,408
Lot FeaturesOther

Neighborhood

Public Transportation • Shopping • Highway Access • Public School

Geography

Property History

Price Drop
$2,295,000

Was $2,349,000

Jul 21, 2026

MLS® 73546333

Listed
$2,349,000

Jul 8, 2026

MLS® 73546333

Population

17,415

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

Median Household Income

$250K

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

Renter-Occupied Homes

12.7%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Norfolk County

1,189 housing units permitted in the last 12 months (+21% vs the prior 12 months) — 706 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 3,776 sq ft principal dwelling). Lot size: 13,408 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.

Full Wellesley, MA market report ZIP 02481 market data
Listing Provided By

Listing Agent: Erica Lockberg

Listing Office: Berkshire Hathaway HomeServices Town and Country Real Estate

MLS® Number: 73546333

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