14 Massasoit Rd, Wellesley, MA 02481
Property image
Property image
OFF MARKET

14 Massasoit Rd
Wellesley, MA 02481

  • 5 Beds
  • 5.5 Baths
  • 5,190 sqft (on 0.33 acres)

$2,732,900

Trulia Estimate
as of Aug 13, 2026
Est. Refi. Payment $16,347/mo*
Refinance Your Home

$2,732,900

Trulia Estimate
as of Aug 13, 2026
Est. Refi. Payment $16,347/mo*
Refinance Your Home
5 Beds
5.5 Baths
5,190 sqft
(on 0.33 acres)

Home Value

Trulia Estimate
$2.73M
Since last month
Decreased$43K (-1.6%)
Since last year
Increased$97K (+3.7%)
Since last sale
Increased$1M (+60.8%)
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 +46% in the last 10 years
MonthEstimated value
2026
August 2026$2.73M
July 2026$2.77M
June 2026$2.78M
May 2026$2.79M
April 2026$2.73M
March 2026$2.73M
February 2026$2.65M
January 2026$2.62M
2025
2024
2023
2022
2021
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
90 Elmwood Rd, Wellesley, MA
0.20
Single-Family Home
$1,902,500
04/30/26
4
3.5
3,428
23 Pilgrim Rd, Wellesley, MA
0.20
Single-Family Home
$2,628,000
05/12/26
4
3.5
4,102
11 Fisher Ave, Wellesley, MA
0.45
Single-Family Home
$3,000,000
06/29/26
5
4.5
5,384
51 Boulder Brook Rd, Wellesley, MA
0.38
Single-Family Home
$3,270,000
12/09/25
5
4.5
4,947
31 Martin Rd, Wellesley, MA
0.10
Single-Family Home
$1,740,000
04/17/26
4
2.5
2,214
15 Parker Rd, Wellesley, MA
0.51
Single-Family Home
$3,100,000
06/01/26
5
5
5,227
25 Mansfield Rd, Wellesley, MA
0.19
Single-Family Home
$1,665,000
04/06/26
4
2
3,091
27 Garrison Rd, Wellesley, MA
0.46
Single-Family Home
$3,100,000
06/01/26
5
5.5
5,926
53 Chesterton Rd, Wellesley, MA
0.48
Single-Family Home
$3,225,000
06/01/26
5
5.5
5,779
428 Weston Rd, Wellesley, MA
0.46
Single-Family Home
$1,497,200
12/09/25
5
3.5
2,558

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
7 Massasoit Rd, Wellesley, MA 02481
0.04
$3,195,000
5
4.5
4,936
For Sale
46 Pilgrim Rd, Wellesley, MA 02481
0.10
$3,110,800
5
4.5
4,591
Off Market
31 Martin Rd, Wellesley, MA 02481
0.10
$1,740,000
4
2.5
2,214
Recently Sold
14 Haven Rd, Wellesley, MA 02481
0.11
$2,760,000
5
5.5
4,229
Off Market
1 Brookfield Cir, Wellesley, MA 02481
0.12
$1,908,400
4
2.5
2,148
Off Market
90 Elmwood Rd, Wellesley, MA 02481
0.20
$1,902,500
4
3.5
3,428
Recently Sold
28 Mansfield Rd, Wellesley, MA 02481
0.17
$2,148,200
5
4.5
3,238
Off Market
97 Elmwood Rd, Wellesley, MA 02481
0.22
$2,016,200
5
3
3,133
Off Market
6 Earle Rd, Wellesley, MA 02481
0.16
$1,512,700
4
2.5
2,384
Off Market
96 Elmwood Rd, Wellesley, MA 02481
0.23
$2,204,900
4
2.5
2,809
Off Market
21 Mansfield Rd, Wellesley, MA 02481
0.18
$3,129,800
6
4.5
4,740
Off Market
10 Wilde Rd, Wellesley, MA 02481
0.19
$1,399,000
3
1.5
1,320
For Sale

Local Information

  • Map ViewExplore the area around 14 Massasoit Rd.
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2005
Lot Size
0.33 acres
Living Area
5,190 sqft
Price/Sqft
$527
Parking
Garage

About this House

Life in the neighborhood revolves around the Boulder Brook Reservation and Bates Elementary School. Everyone is within walking distance of this small and nurturing K-5 public school, creating a great sense of community. Convenience-- 4 miles from "The Golden Mile" shopping area including the Natick Mall, One mile from the shops and restaurants of Wellesley Square and a short drive to any of three commuter rail stops. Nature-- Rocky Ledge conservation land offers many acres of walking trails and meadows leading up into Weston. One can walk out the door and find so much peace and beauty it is hard to believe that you are only a 25 minute drive from Boston.
14 Massasoit Rd, Wellesley, MA 02481 is a 5 bedroom, 6 bathroom, 5,190 sqft single-family home built in 2005. It last sold for $1,700,000 on Jun 29, 2017. It is currently off market. The Trulia Estimate is $2,732,900, with a rent estimate of $9,671/month.

Home Details for 14 Massasoit Rd

Interior Features

Interior Details
BasementNumber of Rooms: 11
Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3
Fireplace & Spa
FireplaceJetted Bath Tub
Security
Security System

Property Information

Year Built
Year Built: 2005
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
Exterior: WoodLawnSprinkler System
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 0.33 acres

Price and Tax history

DateEventPrice
Jun 29, 2017
Source: N/A
Sold
$1,700,000
Aug 14, 2012
Source: N/A
Sold
$1,619,000
Jun 12, 2012
Source: Agent Provided
PriceChange
$1,649,000
Price decreased by 3%
May 18, 2012
Source: Agent Provided
PriceChange
$1,695,000
Price decreased by 6%
Mar 14, 2012
Source: Agent Provided
Listed For Sale
$1,795,000

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
Skip to last item
  • Results are loading
Skip to first item

Around this home

View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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."
    0
    Flag

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

14 pet-friendly rentals in Wellesley, MA

Explore by feature - Garage

14 rentals with a garage in Wellesley, MA

Explore by feature - Air Conditioning

24 rentals with air conditioning in Wellesley, MA

Explore by feature - Washer/dryer

29 rentals with a washer/dryer in Wellesley, MA

Explore by feature - Outdoor Space

6 rentals with an outdoor space in Wellesley, MA

Homes for sale near 14 Massasoit Rd

Skip to last item
Skip to first item

Off Market Homes Near 14 Massasoit Rd

Skip to last item
Skip to first item

Frequently asked questions about 14 Massasoit Rd

  • What is 14 Massasoit Rd estimated to be worth?
    Trulia's estimated value for 14 Massasoit Rd in Wellesley, MA is $2,732,900.
  • What is the price history for 14 Massasoit Rd?
    14 Massasoit Rd in Wellesley, MA last sold for $1,700,000 in June 2017.
  • Is Wellesley a buyer's or seller's market?
    Wellesley is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Wellesley?
    The median sale price in Wellesley is $2.15M. That is up $161K from the prior month.
  • How big is the lot at 14 Massasoit Rd?
    The lot at 14 Massasoit Rd in Wellesley, MA is about 0.33 acres (14,521 sq ft).
  • Does 14 Massasoit Rd have a garage?
    Yes, 14 Massasoit Rd in Wellesley, MA has a garage.