2 Cypress Rd, Wellesley, MA 02481
Property image
Property image
OFF MARKET

$4,581,400

Trulia Estimate
  • 6 Beds
  • 7 Baths
  • 5,972 sqft (on 0.46 acres)

2 Cypress Rd, Wellesley, MA 02481

Est. Refi. Payment $27,232/mo*
Refinance Your Home
Currently Off Market - Sold May 2, 2017 for $2,900,000

Home Value

Trulia Estimate
$4.58M
Since last month
Decreased$105K (-2.2%)
Since last year
Increased$10K (+0.2%)
Since last sale
Increased$2M (+57.1%)
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 +171% in the last 10 years
MonthEstimated value
2026
August 2026$4.56M
July 2026$4.66M
June 2026$4.7M
May 2026$4.71M
April 2026$4.69M
March 2026$4.69M
February 2026$4.49M
January 2026$4.49M
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
10 Lanark Rd, Wellesley, MA
0.17
Single-Family Home
$4,400,000
06/29/26
6
3.5
7,404
101 Edmunds Rd, Wellesley, MA
0.25
Single-Family Home
$3,200,000
07/07/26
5
4.5
4,010
44 Bradford Rd, Wellesley, MA
0.20
Single-Family Home
$3,100,000
06/02/26
5
5.5
4,785
99 Old Colony Rd, Wellesley, MA
0.42
Single-Family Home
$5,097,250
05/15/26
6
6
8,100
56 Ledgeways, Wellesley, MA
0.33
Single-Family Home
$4,400,000
12/01/25
6
8
7,000
33 Hundreds Cir, Wellesley, MA
0.24
Single-Family Home
$3,900,000
08/14/26
5
3.5
5,074
3 Garden Rd, Wellesley, MA
0.32
Single-Family Home
$2,500,000
03/05/26
4
3.5
4,870
40 Chestnut St, Wellesley, MA
0.14
Single-Family Home
$2,450,000
05/06/26
5
3.5
3,369
7 Garden Rd, Wellesley, MA
0.36
Single-Family Home
$2,059,981
09/25/25
5
3.5
4,643
22 Valley Rd, Wellesley, MA
0.40
Single-Family Home
$5,250,000
06/15/26
5
7
7,285

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
12 Cypress Rd, Wellesley, MA 02481
0.04
$2,686,100
5
3.5
3,390
Off Market
11 Cypress Rd, Wellesley, MA 02481
0.06
$3,356,500
6
5
4,665
Off Market
21 Cushing Rd, Wellesley, MA 02481
0.11
$3,814,100
5
5
4,558
Off Market
14 Rockridge Rd, Wellesley, MA 02481
0.09
$4,524,900
6
5.5
5,030
Off Market
21 Rockridge Rd, Wellesley, MA 02481
0.11
-
5
3.5
3,423
Off Market
40 Chestnut St, Wellesley, MA 02481
0.14
$2,450,000
5
3.5
3,369
Recently Sold
15 Rockridge Rd, Wellesley, MA 02481
0.12
$3,360,800
4
3.5
4,100
Off Market
37 Cypress Rd, Wellesley, MA 02481
0.15
$6,039,400
6
7.5
7,932
Off Market
39 Cypress Rd, Wellesley, MA 02481
0.16
$5,762,200
6
7.5
8,522
Off Market
44 Bradford Rd, Wellesley, MA 02481
0.20
$3,100,000
5
5.5
4,785
Recently Sold
10 Lanark Rd, Wellesley, MA 02481
0.17
$4,400,000
6
3.5
7,404
Recently Sold
47 Cypress Rd, Wellesley, MA 02481
0.21
$3,609,100
5
6
7,300
Off Market

Local Information

  • Map ViewExplore the area around 2 Cypress Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2016
Lot Size
0.46 acres
Living Area
5,972 sqft
Price/Sqft
$767

About this House

Stunning new Shingle Style Gambrel just completed in the Olde Cliff Estates. Sophisticated and warm, this 7300 square foot masterpiece by an award-winning custom builder leaves nothing off your "must have" list. Stylish living room with fireplace and generous dining room featuring with custom trim and beautiful butler's pantry offer incredible entertaining space for holidays and gatherings. Bright and airy kitchen featuring oversized island, huge walk-in storage pantry and breakfast room opens to sun-splashed family room with fireplace and double doors to private patio with roaring outdoor brick fireplace, and private play yard. Serene master suite w/luxurious spa-like bath and his & her walk-in closets + 4 additional en suite family bedrooms on the second floor. 6th en suite bedroom on private third floor. Killer mudroom with light-filled open back staircase connects family room to yard, three car garage, and fully finished LL w/all the bells & whistles. Walk to Wellesley Hills Train
2 Cypress Rd, Wellesley, MA 02481 is a 6 bedroom, 7 bathroom, 5,972 sqft single-family home built in 2016. It last sold for $2,900,000 on May 2, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $4,581,400, with a rent estimate of $6,559/month.

Home Details for 2 Cypress Rd

Interior Features

Heating & Cooling
Heating: GasAir ConditioningHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 3
Interior Details
Number of Rooms: 15Types of Rooms: Recreation Room
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 2016
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
Exterior: Wood

Community

Units in Building: 1

Lot Information

Lot Area: 0.46 acres

Price and Tax history

DateEventPrice
Nov 1, 2023
Source: MLS PIN #73172069
ListingRemoved
$4,495,000
Oct 19, 2023
Source: MLS PIN #73172069
Listed For Sale
$4,495,000
May 2, 2017
Source: N/A
Sold
$2,900,000
Aug 3, 2015
Source: N/A
Sold
$1,290,000

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

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
    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
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LGBTQ Local Legal Protections

Frequently asked questions about 2 Cypress Rd

  • What is 2 Cypress Rd estimated to be worth?
    Trulia's estimated value for 2 Cypress Rd in Wellesley, MA is $4,581,400.
  • What is the price history for 2 Cypress Rd?
    2 Cypress Rd in Wellesley, MA last sold for $2,900,000 in May 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 2 Cypress Rd?
    The lot at 2 Cypress Rd in Wellesley, MA is about 0.46 acres (20,037 sq ft).

Explore by feature - Pet Friendly

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Off Market Homes Near 2 Cypress Rd

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