2 Cypress Rd, Wellesley, MA 02481
OFF MARKET

2 Cypress Rd
Wellesley, MA 02481

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

$4,746,900

Trulia Estimate
as of May 30, 2026
Est. Refi. Payment $27,492/mo*
Refinance Your Home

$4,746,900

Trulia Estimate
as of May 30, 2026
Est. Refi. Payment $27,492/mo*
Refinance Your Home
6 Beds
7 Baths
5,972 sqft
(on 0.46 acres)

Local Information

Map showing home location
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-- mins to
Commute Destination

Description

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
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
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A/C
Heating & Cooling
HOA
None
Price/Sqft
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Listed
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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 History for 2 Cypress Rd

DatePriceEventSource
11/01/2023$4,495,000ListingRemovedMLS PIN #73172069
10/19/2023$4,495,000Listed For SaleMLS PIN #73172069
05/02/2017$2,900,000Sold
N/A
08/03/2015$1,290,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$40,205
Assessment$3,911,000
Home facts updated by county records

Comparable Sales for 2 Cypress Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
10 Lanark Rd, Wellesley, MA
0.17
Single-Family Home
$4,400,000
07/10/25
6
3.5
6,996
12 Cypress Rd, Wellesley, MA
0.04
Single-Family Home
$2,610,000
06/02/25
5
3.5
3,390
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
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
36 Old Farm Rd, Wellesley, MA
0.45
Single-Family Home
$3,475,000
07/31/25
5
5.5
5,359
7 Garden Rd, Wellesley, MA
0.36
Single-Family Home
$2,059,981
09/25/25
5
3.5
4,643
5 Cliff Rd, Wellesley, MA
0.37
Single-Family Home
$3,200,000
07/02/25
5
4.5
5,210
1 Clock Tower Dr, Wellesley, MA
0.57
Single-Family Home
$2,500,000
04/13/26
5
4.5
5,261

Nearby homes

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Assigned Schools

These are the assigned schools for 2 Cypress Rd.
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
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  • 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."
    0
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2 Cypress Rd, Wellesley, MA 02481 is a 6 bedroom, 7 bathroom, 5,972 sqft single-family home built in 2016. This property is not currently available for sale. 2 Cypress Rd was last sold on May 2, 2017 for $2,900,000. The current Trulia Estimate for 2 Cypress Rd is $4,746,900.