8 Cypress Rd, Wellesley, MA 02481
Property image
Property image
FOR SALE
NEW
OPEN THU, 11-12PM

$1,799,000

  • 4 Beds
  • 3.5 Baths
  • 2,714 sqft

8 Cypress Rd, Wellesley, MA 02481

Est. Mortgage $10,729/mo*
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Home Highlights

Single-Family Home
Built in 1895
$663/sqft
Garage

Local Information

  • Map ViewExplore the area around 8 Cypress Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Perched atop Wellesley's prestigious Cliff Estates, this beautifully renovated Victorian blends timeless architectural charm with modern comfort. Offering 4 bedrooms and 3.5 baths, the home has been thoughtfully updated while preserving its original character and period details. The sun-filled kitchen features a breakfast nook overlooking the landscaped backyard, while elegant living, dining, and music rooms provide ideal spaces for everyday living and entertaining. The second floor includes three spacious bedrooms, including a serene primary suite. The third level offers an additional bedroom, full bath, and a flexible bonus room perfect for a family room, home office, gym, or playroom. Enjoy a private patio, oversized detached two-car garage, and a picturesque setting in one of Wellesley's most sought-after area. A rare opportunity to own a home where historic elegance meets modern living.
Last check for updates: about 1 hour ago
Listing courtesy of Osnat Levy, (617) 833-1055
eXp Realty LLC - Corporate Office, (888) 854-7493
Source: MLS PIN, MLS#73574530
Also Listed on MLS PIN, eXp Realty.

Open House

Thursday, September 10
11:00 AM to 12:00 PM

Home Details for 8 Cypress Rd

Interior Features

Interior Details
Basement: FullNumber of Rooms: 9Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Master Bathroom, Bathroom 1, Bathroom 2, Bathroom 3, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2714 Square Feet
Appliances & Utilities
Utilities: for Gas Range, for Gas DryerAppliances: Gas Water Heater, Oven, Dishwasher, Disposal, Microwave, Range, Refrigerator, Washer, Dryer, Vacuum SystemDishwasherDisposalDryerLaundry: In Basement,Gas Dryer HookupMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Living RoomHas a FireplaceNo Spa
Gas & Electric
Electric: 200+ Amp Service
Windows, Doors, Floors & Walls
Door: French DoorsFlooring: Wood, Flooring - Stone/Ceramic Tile, Flooring - Hardwood
Levels, Entrance, & Accessibility
Floors: Wood, Flooring Stone Ceramic Tile, Flooring Hardwood

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Porch, PatioExterior: Porch, PatioFoundation: Stone
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Open Parking Spaces: 2No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 4Parking: Detached,Paved Drive,Off Street
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 2714

Days on Market

Days on Market: 1

Property Information

Year Built
Year Built: 1895
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial,Victorian
Building
Not Attached PropertyDoes Not Include Home Warranty
Property Information
Parcel Number: M:084 R:030 S:, 259791

Price & Status

Price
List Price: $1,799,000Price Per Sqft: $663

Active Status

MLS Status: New

Location

Direction & Address
City: Wellesley
School Information
Elementary School: SpragueJr High / Middle School: WmdHigh School: Whs

Agent Information

Listing Agent
Listing ID: 73574530

Building

Building Area
Building Area: 2714 Square Feet

Community

Community Features: Public Transportation, Shopping, Park, Walk/Jog Trails, Medical Facility, Highway Access, House of Worship, T-StationNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 7604 sqft

Miscellaneous

BasementMls Number: 73574530Above Grade Unfinished Area: 2714

Additional Information

Public TransportationShoppingParkWalk/Jog TrailsMedical FacilityHighway AccessHouse of WorshipT-Station

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
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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
    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
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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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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
$1.74M
Since last month
Increased$13K (+0.7%)
Since last year
Increased$15K (+0.9%)
Since last sale
Increased$1M (+269.1%)
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 +35% in the last 10 years
MonthEstimated value
2026
September 2026$1.73M
August 2026$1.69M
July 2026$1.72M
June 2026$1.71M
May 2026$1.75M
April 2026$1.74M
March 2026$1.72M
February 2026$1.64M
January 2026$1.66M
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
40 Chestnut St, Wellesley, MA
0.16
Single-Family Home
$2,450,000
05/06/26
5
3.5
3,369
2 Woodlawn Oval, Wellesley, MA
0.58
Single-Family Home
$2,100,000
07/31/26
4
3.5
2,953
92 Woodlawn Ave, Wellesley, MA
0.45
Single-Family Home
$1,953,000
06/03/26
4
2.5
2,627
54 Colburn Rd, Wellesley, MA
0.41
Single-Family Home
$1,655,000
01/30/26
4
2.5
2,204
15 Clifton Rd, Wellesley, MA
0.48
Single-Family Home
$1,635,650
04/16/26
4
2.5
2,112
35 Arnold Rd, Wellesley, MA
0.35
Single-Family Home
$2,525,000
06/26/26
4
3.5
3,497
22 Kimlo Rd, Wellesley, MA
0.48
Single-Family Home
$830,000
10/01/25
3
2
1,466
10 Kirkland Cir, Wellesley, MA
0.58
Single-Family Home
$2,480,000
08/14/26
4
3.5
3,610
26 Kimlo Rd, Wellesley, MA
0.45
Single-Family Home
$1,065,800
12/02/25
3
2
1,505
36 Kimlo Rd, Wellesley, MA
0.43
Single-Family Home
$1,130,000
08/14/26
3
2
1,431

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
0.01
$2,701,100
5
3.5
3,390
Off Market
11 Cypress Rd, Wellesley, MA 02481
0.04
$3,326,200
6
5
4,665
Off Market
21 Cushing Rd, Wellesley, MA 02481
0.10
$3,834,900
5
5
4,558
Off Market
14 Rockridge Rd, Wellesley, MA 02481
0.11
$4,494,000
6
5.5
5,030
Off Market
21 Rockridge Rd, Wellesley, MA 02481
0.13
$2,933,800
5
3.5
3,423
Off Market
40 Chestnut St, Wellesley, MA 02481
0.16
$2,450,000
5
3.5
3,369
Recently Sold
15 Rockridge Rd, Wellesley, MA 02481
0.14
$3,346,500
4
3.5
4,100
Off Market
37 Cypress Rd, Wellesley, MA 02481
0.13
$6,027,200
6
7.5
7,932
Off Market
39 Cypress Rd, Wellesley, MA 02481
0.14
$5,762,200
6
7.5
8,522
Off Market
44 Bradford Rd, Wellesley, MA 02481
0.18
$3,100,000
5
5.5
4,785
Recently Sold
10 Lanark Rd, Wellesley, MA 02481
0.19
$4,400,000
6
3.5
7,404
Recently Sold

Price and Tax history

DateEventPrice
Sep 9, 2026
Source: MLS PIN #73574530
Listed For Sale
$1,799,000
Feb 24, 1997
Source: N/A
Sold
$470,000

LGBTQ Local Legal Protections

Osnat Levy, eXp Realty LLC - Corporate Office, (888) 854-7493
Agent Phone: (617) 833-1055
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 8 Cypress Rd

  • What is the estimated monthly payment for 8 Cypress Rd?
    Based on a $1,799,000 list price with 20% down at today's rates, the estimated monthly payment for 8 Cypress Rd in Wellesley, MA is approximately $11,196 (about $9,592 principal & interest, $1,529 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 8 Cypress Rd compare to homes in Wellesley?
    8 Cypress Rd in Wellesley, MA is listed at $1,799,000, about 16% below 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 8 Cypress Rd?
    The closest schools to 8 Cypress Rd in Wellesley, MA are Sprague Elementary School (rated 9/10), Wellesley High School (rated 10/10), Wellesley Middle School (rated 8/10).
  • Does 8 Cypress Rd have air conditioning?
    Yes, 8 Cypress Rd in Wellesley, MA has air conditioning.
  • Does 8 Cypress Rd have laundry facilities?
    Yes, 8 Cypress Rd in Wellesley, MA has in-unit laundry.
8 Cypress Rd, Wellesley, MA 02481 is a 4 bedroom, 4 bathroom, 2,714 sqft single-family home built in 1895. This property is currently available for sale and was listed by MLS PIN on Sep 9, 2026. The MLS # for this home is MLS# 73574530.