38 Upwey Rd, Wellesley, MA 02481
Property image
Property image
FOR SALE
3D VIEW
0.31 ACRES

$2,295,000

Original price: $2,349,000
  • 4 Beds
  • 3.5 Baths
  • 3,776 sqft (on 0.31 acres)

38 Upwey Rd, Wellesley, MA 02481

Est. Mortgage $13,667/mo*
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Home Highlights

Single-Family Home
Built in 1993
0.31 acre lot
$608/sqft
Garage

Local Information

  • Map ViewExplore the area around 38 Upwey Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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.
Last check for updates: about 22 hours ago
Listing courtesy of Erica Lockberg, (339) 225-1342
Berkshire Hathaway HomeServices Town and Country Real Estate, (781) 237-8787
Source: MLS PIN, MLS#73546333
Also Listed on BHHS broker feed, MLS PIN.

Home Details for 38 Upwey Rd

Interior Features

Interior Details
Basement: Partial,FinishedNumber of Rooms: 9Types of Rooms: Master Bathroom
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3776 Square Feet
Heating & Cooling
Heating: Forced Air,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 2Has a FireplaceNo Spa

Exterior Features

Exterior Home Features
Foundation: Concrete Perimeter
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Open Parking Spaces: 4Has a GarageParking Spaces: 6Parking: Garage
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 2785Finished Area (below surface): 991

Days on Market

Days on Market: 62

Property Information

Year Built
Year Built: 1993
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Not Attached PropertyDoes Not Include Home Warranty
Property Information
Parcel Number: 260477

Price & Status

Price
List Price: $2,295,000Price Per Sqft: $608

Active Status

MLS Status: Active

Location

Direction & Address
City: Wellesley

Agent Information

Listing Agent
Listing ID: 73546333

Building

Building Area
Building Area: 3776 Square Feet

Community

Community Features: Public Transportation, Shopping, Highway Access, Public SchoolNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.31 acres

Miscellaneous

BasementMls Number: 73546333Above Grade Unfinished Area: 2785

Additional Information

Public TransportationShoppingHighway AccessPublic School

Around this home

What Locals Say about Wellesley

At least 124 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 87 % Say parking is easy

  • 85 % Say people would walk alone at night

  • 84 % Say yards are well-kept

  • 80 % Say car is needed

  • 79 % Say there are sidewalks

  • 76 % Say kids play outside

  • 75 % Say there's holiday spirit

  • 74 % Say streets are well-lit

  • 73 % Say there's wildlife

  • 72 % Say it's quiet

  • 70 % Say they plan to stay for at least 5 years

  • 67 % Say it's walkable to restaurants

  • 66 % Say neighbors are friendly

  • 65 % Say there are community events

  • 63 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Mike Holiday
    "Everyone walks their dogs and lets their dogs say hello, most often. People know each other. It’s a great community"
    0
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  • Emilyperrottet
    "Nothing. It’s a changing neighborhood with a mix of old and new homes. Most of the homes are old and run down. "
    0
    Flag
  • Emilyperrottet
    "I take the Commuter rail from Wellesley to the T subway. 1.5 hours to Cambridge from south station. "
    0
    Flag
  • Trulia User
    "Lots of trails and other dogs in the area, many pet stores in the area as well. Dogs are well behaved and friendly. "
    0
    Flag
  • Shirley L.
    "The walking paths and yearly town celebrations are wonderful! A great sense of community and great schools. "
    0
    Flag
  • Sdipietro369
    "I am a visitor to this area. The neighborhood seems very nice with Babson College right around the corner. Shops within a close distance. "
    3
    Flag
  • Katrina C.
    "You feel you're kids are safe here in town. Everyone is friendly and we're all neighbors. It's a lovely town with a community feeling. "
    2
    Flag
  • Jamie.solomon1
    "I lived in Weston for two years and it’s a delightful town, with gorgeous land and large houses. Usually at least an acre"
    1
    Flag
  • Cmt138
    "Great access to commuter rail from either Wellesley Square or Wellesley Hills. Easy 10-15 min walk. Better parking from Wellesley Square. Usually takes about 1/2 hour to Back Bay. Driving into Boston can take a little more time with traffic to cross town to Mass Pike."
    2
    Flag
  • Laura M.
    "There are lots of dogs in our neighborhood- people walk them all the time. Dogs are welcome at Morse’s pond in the off season. "
    1
    Flag
  • Bruce C.
    "Lots of other dog owners who walk their dogs all the time. Also plenty of space to run with dogs on a trail or away from streets. "
    1
    Flag
  • Keith S.
    "Lots of trails and public spaces. Nationally acclaimed colleges. Variety of great shops and restaurants."
    0
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  • Srodousakis
    "Wellesley is a beautiful but very privileged neighborhood. It is very safe and people are friendly. Schools are great! There is a cute downtown and generally it’s a great place to raise kids. "
    0
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  • Molly R.
    "i love my neighborhood. everyone is so kind and welcoming. we often times have little gatherings or block parties. everyone knows each other and we are a very close community. "
    0
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  • Victoria V.
    "That I live on route 16 and nobody lets me out of my driveway in the morning and I have to leave for work an hour early just because of that."
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Market trends in Wellesley

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.15M
$161KMoM
Sale-to-List Price
100.6%
0.4%MoM
Price per sq ft
$666
$18MoM
Available listings
87
25MoM

Home Value

Trulia Estimate
$2.21M
Since last month
Decreased$24K (-1.1%)
Since last year
Increased$18K (+0.8%)
Since last sale
Increased$2M (+235.3%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +51% in the last 10 years
MonthEstimated value
2026
September 2026$2.21M
August 2026$2.19M
July 2026$2.24M
June 2026$2.28M
May 2026$2.32M
April 2026$2.26M
March 2026$2.29M
February 2026$2.18M
January 2026$2.14M
2025
2024
2023
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
10 Kirkland Cir, Wellesley, MA
0.13
Single-Family Home
$2,480,000
08/14/26
4
3.5
3,610
345 Linden St, Wellesley, MA
0.19
Single-Family Home
$2,600,000
05/29/26
4
3.5
4,016
4 Arnold Rd, Wellesley, MA
0.12
Single-Family Home
$1,750,000
09/23/25
4
2.5
3,156
15 Clifton Rd, Wellesley, MA
0.24
Single-Family Home
$1,635,650
04/16/26
4
2.5
2,112
25 Shaw Rd, Wellesley, MA
0.18
Single-Family Home
$1,825,000
03/06/26
5
4.5
4,580
642 Worcester St, Wellesley, MA
0.35
Single-Family Home
$1,177,000
08/06/26
3
2.5
3,129
79 Alba Rd, Wellesley, MA
0.26
Single-Family Home
$2,450,000
06/04/26
4
4
4,676
35 Arnold Rd, Wellesley, MA
0.26
Single-Family Home
$2,525,000
06/26/26
4
3.5
3,497
45 Kingsbury St, Wellesley, MA
0.27
Single-Family Home
$1,913,000
05/20/26
6
3
2,980
53 Audubon Rd, Wellesley, MA
0.41
Single-Family Home
$2,325,000
08/05/26
4
3.5
3,406

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
33 Upwey Rd, Wellesley, MA 02481
0.04
$1,918,500
4
2.5
3,346
Off Market
37 Kirkland Cir, Wellesley, MA 02481
0.07
$1,687,400
4
2.5
2,346
Off Market
560 Worcester St, Wellesley, MA 02481
0.07
$1,395,000
4
2.5
1,800
For Sale
34 Upwey Rd, Wellesley, MA 02481
0.04
$2,220,300
4
3.5
3,286
Off Market
17 Upwey Rd, Wellesley, MA 02481
0.07
$2,587,900
3
1.5
1,764
Off Market
4 Arnold Rd, Wellesley, MA 02481
0.12
$1,844,700
4
2.5
3,156
Off Market
35 Windemere Rd, Wellesley, MA 02481
0.07
$1,322,100
3
2.5
1,774
Off Market
10 Kirkland Cir, Wellesley, MA 02481
0.13
$2,480,000
4
3.5
3,610
Recently Sold
61 Kirkland Cir, Wellesley, MA 02481
0.13
$1,692,600
4
2
2,808
Off Market
44 Windemere Rd, Wellesley, MA 02481
0.11
$1,500,000
3
3
2,447
For Sale
25 Shaw Rd, Wellesley, MA 02481
0.18
$1,825,000
5
4.5
4,580
Recently Sold

Price and Tax history

DateEventPrice
Jul 21, 2026
Source: MLS PIN #73546333
PriceChange
$2,295,000
Price decreased by 2%
Jul 8, 2026
Source: MLS PIN #73546333
Listed For Sale
$2,349,000
Aug 10, 1995
Source: N/A
Sold
$660,000
Sep 3, 1993
Source: N/A
Sold
$526,280

LGBTQ Local Legal Protections

Erica Lockberg, Berkshire Hathaway HomeServices Town and Country Real Estate, (781) 237-8787
Agent Phone: (339) 225-1342
The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing 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 or leasing. 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 set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.

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Frequently asked questions about 38 Upwey Rd

  • What is the estimated monthly payment for 38 Upwey Rd?
    Based on a $2,295,000 list price with 20% down at today's rates, the estimated monthly payment for 38 Upwey Rd in Wellesley, MA is approximately $14,173 (about $12,147 principal & interest, $1,951 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 38 Upwey Rd compare to homes in Wellesley?
    38 Upwey Rd in Wellesley, MA is listed at $2,295,000, about 7% above the $2.15M median sale price in Wellesley.
  • What do residents say about Wellesley?
    Residents describe Wellesley, MA as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See homes for sale in Wellesley, MA.
  • What are the closest schools to 38 Upwey Rd?
    The closest schools to 38 Upwey Rd in Wellesley, MA are Sprague Elementary School (rated 9/10), Wellesley High School (rated 10/10), Wellesley Middle School (rated 8/10).
  • Does 38 Upwey Rd have air conditioning?
    Yes, 38 Upwey Rd in Wellesley, MA has air conditioning.
  • How big is the lot at 38 Upwey Rd?
    The lot at 38 Upwey Rd in Wellesley, MA is about 0.31 acres (13,408 sq ft).
38 Upwey Rd, Wellesley, MA 02481 is a 4 bedroom, 4 bathroom, 3,776 sqft single-family home built in 1993. This property is currently available for sale and was listed by MLS PIN on Jul 8, 2026. The MLS # for this home is MLS# 73546333.