42
$2,545,000
5 bd · 4 ba · 4,086 sqft
21 Elmwood Rd, Wellesley, MA
Declan O'Toole · SelectRE Boston
Est. $18,642/moGet pre-qualified$499/sqft · 574 days on Realty
6
Beds
6
Baths
5,806
Sqft
1933
Built
PROPERTY IS TEMPORARILY OFF THE MARKET, BUT CAN STILL BE SHOWN. Welcome home to this spacious and elegant colonial farmhouse nestled on its own private hill in the coveted Cliff Estates. The home perfectly blends the charm and character of an original farmhouse (including 8 original fireplaces) with modern features that suit today's lifestyle, such as multiple options for home office spaces. Five bedrooms (including primary suite) are located on the second floor. Sixth bedroom with full bathroom and bonus room on third floor is perfect for guests or in-laws to have privacy. Main level flows nicely with kitchen, butler's pantry, dining room, family room, office, sunroom, mudroom, laundry and 2 half baths. French doors from the kitchen and family room lead outside to a backyard oasis. A level yard with a lovely patio makes this a perfect place to relax outdoors on over 1/2 acre of private land.
Listing agent
Not provided
Courtesy of brokerage not provided
MLS Property Information Network (MLS PIN) · Listing 73344384
Range $2,745,404 – $3,244,596 · as of July 14, 2026
ATTOM automated valuation model · 53 published estimates over 6.5 years · shaded band is the model's own published low-to-high range
Highest reading $3,895,000 in September 2023; lowest $2,263,553 in April 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$579,800
Estimated monthly payment
$18,642/mo
Loan amount $2,319,200. Estimate only — your actual rate and payment depend on credit, location, and lender.
2025 roll
MLS Property Information Network (MLS PIN)This content last refreshed on 2026-10-07 11:10:48 UTC. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.
School ratings (A+ to F) from HJN community data.
Montessori Day School of Wellesley Hills
PK-TKG · Montessori
5 students · 1.6:1 student–teacher
Wellesley Middle School
6-8 · Regular · Wellesley School District
919 students · 9.0:1 student–teacher
Wellesley High School
9-12 · Regular · Wellesley School District
1,262 students · 10.8:1 student–teacher
Isaac Sprague Elementary School
KG-5 · Regular · Wellesley School District
289 students · 11.7:1 student–teacher
Katharine Lee Bates Elementary School
KG-5 · Regular · Wellesley School District
286 students · 12.9:1 student–teacher
Horatio H. Hunnewell Elementary School
KG-5 · Regular · Wellesley School District
294 students · 10.6:1 student–teacher
Dana Hall School
5-12 · Regular
483 students · 8.5:1 student–teacher
John D. Hardy Elementary School
KG-5 · Regular · Wellesley School District
280 students · 10.6:1 student–teacher
42$2,545,000
5 bd · 4 ba · 4,086 sqft
21 Elmwood Rd, Wellesley, MA
Declan O'Toole · SelectRE Boston
Price Reduced29$3,095,000
6 bd · 5 ba · 4,424 sqft
209 Bristol Rd, Wellesley, MA
Elisabeth Preis · Compass
16$3,195,000
5 bd · 5 ba · 5,044 sqft
16 Rockland Street, Wellesley, MA
Adler Connolly Squared Team · MGS Group Real Estate LTD - Wellesley
Price Reduced34$3,600,000
5 bd · 6 ba · 6,289 sqft
23 Bellevue, Wellesley, MA
Ritu Chawla · Coldwell Banker Realty - Wellesley
Price Reduced39$2,650,000
5 bd · 4 ba · 4,110 sqft
100 Albion Rd, Wellesley, MA
Debi Benoit · William Raveis R.E. & Home Services
Price Reduced34$3,450,000
5 bd · 6 ba · 5,800 sqft
144 Washington Street, Wellesley, MA
Patricia Bradley · Rutledge Properties
Within 2 miles of this home: 38+ restaurants and cafés, 3 grocery stores, 37+ parks and green spaces, and 14 transit stops.
Place data from OpenStreetMap.
Caffè Nero
Washington Street
Le Petit Four
Washington Street
Pho Station
Vietnamese restaurant · Washington Street
The Local
American restaurant · Forest Street
Singh's Cafe
Indian restaurant · Washington Street
Maugus Restaurant
Washington Street
Comella's
Italian restaurant · Washington Street
Coconut Thai Cafe
Thai restaurant · Washington Street
Whole Foods Market
Washington Street
Roche Bros
Linden Street
Fells Market
Weston Road
Devil's Slide
Abbott Pond Land
Rockridge Pond
Elm Park
Washington Street
Colburn Road Reservation
Phillips Park
Freinds of Phillips Park Playground
Brown Park Playground
Wellesley Hills
Whole Foods
Wellesley Senior Center
Wellesley Farms
Wellesley Farms (Outbound)
Wellesley Farms Inbound Platform
Wellesley Farms (Inbound)
Wellesley Square
Rings at ½ mile and 1 mile. Basemap © OpenMapTiles © OpenStreetMap contributors.
Open the Wellesley camera map2 devices mapped within ½ mile of this home: 1 license-plate reader and 1 CCTV camera; one of them identified as a Flock Safety device. Nearest: 0.4 mi east. Operators named in the data: Wellesley PD and Wellesley Police Department (?).
| Device type | Within ½ mi | Within 1 mi |
|---|---|---|
| License-plate readers | 1 | 1 |
| of which Flock Safety | 1 | 1 |
| CCTV cameras | 1 | 5 |
Community-reported via OpenStreetMap; may be incomplete. Data as of . © OpenStreetMap contributors (ODbL)
License-plate readers (ALPR) are fixed cameras that photograph passing vehicles and read their plates. Records are typically shared with the agency or association that operates the camera.
Flock Safety is a company whose plate-reader cameras are used by police departments, cities, HOAs and businesses. Its devices are usually solar-powered and pole-mounted.
CCTV cameras are fixed video cameras that record a street, building or other area.
