Single Family Residence at 8 Cypress Rd, Wellesley MA 02481
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25 photos

$1,799,000

8 Cypress Rd, Wellesley MA 02481
Wellesley, MA 02481
Listed by Osnat Levy
Bedrooms
4
Bathrooms
3.5
Living area
2,714 sqft
Year built
1895

About this home

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.

Highlights

Fireplace

Property details

MLS
MLS Property Information Network
MLS #
73574530
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
42
On market date
September 9, 2026
Stories
N/A
Total bathrooms
3.5
Garage spaces
2
Parking spaces
4
Lot size
0.17 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
Ernest F Upham
0.94 mi away · Grades 0-5
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
165
Student:teacher ratio
8.3:1
District
Wellesley
Middle
Wellesley Middle
0.92 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,008
Student:teacher ratio
9.4:1
District
Wellesley
High
Wellesley Sr High
0.99 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,406
Student:teacher ratio
11.9:1
District
Wellesley

Walkability

Blended score for Wellesley's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

50
Somewhat walkable
out of 100
EPA National Walkability Index
5.5 / 20 -- Least walkable
Google Places amenity density
83 / 100
Restaurants & cafes20
Grocery stores3
Parks18
Schools20
Transit stops1
Pharmacies1

Market position

How this listing compares to current activity in Wellesley, from live MLS data.

On the market 42 days -- 73 fewer days than Wellesley's current average of 115 days.
For reference, the median list price across 183 active listings in Wellesley right now is $1,747,200.

Mortgage calculator

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Est. monthly payment
$10,984/mo
$359,800 down
$1,439,200 loan
Principal & interest$9,335
Property tax (est.)$1,499
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated September 13, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.