21 Madison Rd
Wellesley, MA 02481
4 Beds
3.5 Baths
2,609 sqft (on 0.29 acres)
4 Beds
3.5 Baths
2,609 sqft
(on 0.29 acres)
Local Information
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Description
Beautifully renovated and thoughtfully updated, this stunning four-bedroom home offers the perfect blend of timeless charm and modern comfort. Nestled on a picturesque setting the property enjoys exceptional privacy, peaceful views, and a true connection to nature. Sun-filled interiors feature spacious living areas, refined finishes, and an inviting floor plan designed for both everyday living and effortless entertaining. The renovated kitchen opens seamlessly to warm and welcoming family spaces, while oversized windows bring the outdoors in at every turn. Generously sized bedrooms, updated baths, and flexible living areas provide comfort and versatility for today’s lifestyle. Outside, expansive outdoor spaces create the ideal backdrop for relaxing, dining, or enjoying the tranquil natural surroundings. Rarely does a home combine such beautiful renovations with an idyllic setting, all while remaining close to top schools, commuting routes & all Wellesley has to offer.
Home Highlights
Parking
1 Car Garage
Outdoor
Porch, Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
$765
Listed
5 days ago
Home Details for 21 Madison Rd
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Interior Details Basement: Full,Partially FinishedNumber 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 |
Beds & Baths Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 2609 Square Feet |
Appliances & Utilities Utilities: for Gas Range, Washer HookupAppliances: Range, Refrigerator, Wine RefrigeratorLaundry: Washer Hookup,Second FloorRefrigerator |
Heating & Cooling Heating: Forced Air,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air |
Fireplace & Spa Number of Fireplaces: 2Fireplace: Dining RoomHas a FireplaceNo Spa |
Windows, Doors, Floors & Walls Window: Insulated WindowsDoor: Storm Door(s)Flooring: Carpet, Hardwood, Flooring - Wall to Wall Carpet, Laminate |
Levels, Entrance, & Accessibility Floors: Carpet, Hardwood, Flooring Wall To Wall Carpet, Laminate |
View Has a ViewView: Scenic View(s) |
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Exterior Home Features Roof: ShinglePatio / Porch: Porch, PatioExterior: Porch, Patio, Professional LandscapingFoundation: Concrete Perimeter |
Parking & Garage Number of Garage Spaces: 1Number of Covered Spaces: 1Open Parking Spaces: 4No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 5Parking: Attached,Off Street,Paved |
Frontage Road Frontage: PublicResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: PavedNot on Waterfront |
Water & Sewer Sewer: Public Sewer |
Finished Area Finished Area (above surface): 2109Finished Area (below surface): 500 |
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Days on Market: 5 |
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Year Built Year Built: 1940 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Garrison |
Building Construction Materials: FrameNot Attached PropertyDoes Not Include Home Warranty |
Property Information Parcel Number: M:016 R:028 S:, 257142 |
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Price List Price: $1,995,000Price Per Sqft: $765 |
Status Change & Dates Off Market Date: Fri Jun 05 2026 |
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MLS Status: Under Agreement |
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Direction & Address City: Wellesley |
School Information Elementary School: WellesleyJr High / Middle School: WmsHigh School: Whs |
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Listing Agent Listing ID: 73529338 |
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Building Area Building Area: 2609 Square Feet |
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Community Features: Public Transportation, Shopping, Park, Walk/Jog Trails, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Public School, UniversityNot Senior Community |
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No HOA |
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Lot Area: 0.29 acres |
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BasementMls Number: 73529338Above Grade Unfinished Area: 2109 |
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Public TransportationShoppingParkWalk/Jog TrailsMedical FacilityBike PathConservation AreaHighway AccessHouse of WorshipPublic SchoolUniversity |
Last check for updates: about 3 hours ago
Listing courtesy of The Lara & Chelsea Collaborative, (617) 852-7018
Coldwell Banker Realty - Wellesley, (781) 237-9090
The Lara & Chelsea Collaborative, (617) 852-7018
Source: MLS PIN, MLS#73529338
Also Listed on MLS PIN.
Market trends in Wellesley
Last updated April 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
108 6MoM
Price History for 21 Madison Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 06/05/2026 | $1,995,000 | Pending | MLS PIN #73529338 |
| 06/03/2026 | $1,995,000 | Listed For Sale | MLS PIN #73529338 |
| 08/12/2024 | $1,800,000 | Sold | MLS PIN #73248316 |
| 06/08/2024 | $1,675,000 | Contingent | MLS PIN #73248316 |
| 06/06/2024 | $1,675,000 | Listed For Sale | MLS PIN #73248316 |
| 05/03/2018 | $1,299,000 | Sold | N/A |
| 02/26/2018 | $1,299,000 | Pending | Agent Provided |
| 02/19/2018 | $1,299,000 | Listed For Sale | Agent Provided |
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $18,031 |
| Assessment | $1,754,000 |
Home facts updated by county records
Comparable Sales for 21 Madison Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.15 | Single-Family Home | $1,660,000 | 06/25/25 | 4 | 2.5 | 2,514 | |
0.08 | Single-Family Home | $1,680,000 | 06/09/25 | 5 | 2.5 | 2,028 | |
0.30 | Single-Family Home | $1,625,000 | 06/04/26 | 3 | 2.5 | 1,996 | |
0.38 | Single-Family Home | $1,600,000 | 07/02/25 | 5 | 4 | 3,272 | |
0.23 | Single-Family Home | $1,180,000 | 02/18/26 | 3 | 2 | 2,421 | |
0.27 | Single-Family Home | $2,295,000 | 09/17/25 | 4 | 4.5 | 3,560 | |
0.40 | Single-Family Home | $1,925,000 | 08/13/25 | 4 | 4.5 | 4,300 | |
0.55 | Single-Family Home | $1,880,000 | 06/05/26 | 4 | 3 | 2,332 | |
0.27 | Single-Family Home | $2,600,000 | 03/30/26 | 4 | 4 | 3,282 | |
0.39 | Single-Family Home | $2,165,000 | 11/05/25 | 4 | 4.5 | 4,691 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
OFF MARKETChristine Lawrence, Rutledge Properties
OFF MARKETThe Varano Realty Group, Keller Williams Realty
OFF MARKETWilliam Concannon, Louise Condon Realty
OFF MARKETDonahue Maley and Burns Team, Compass
FOR SALE1.42 ACRESChristine Norcross & Partners, William Raveis R.E. & Home Services
OFF MARKETMelissa Dailey, Coldwell Banker Realty - Wellesley
OFF MARKETThe Shulkin Wilk Group, Compass
OFF MARKETChristine Lawrence, Rutledge Properties
OFF MARKETEvanthia Nassios, Asteri Real Estate
OFF MARKETChristine Norcross & Partners, William Raveis R.E. & Home Services
OFF MARKETMelissa Dailey, Coldwell Banker Realty - Wellesley
OFF MARKETTeri Adler, MGS Group Real Estate LTD - Wellesley
Assigned Schools
These are the assigned schools for 21 Madison Rd.
- Joseph E. Fiske Elementary School
- K-5
- Public
- 263 Students
9/10GreatSchools RatingParent Rating AverageFiske Elementary School in Wellesley, Massachusetts, provides an extremely positive learning environment, where progress, hard work, and personal effort are observed, commented on, and valued. Principal Anthony Colannino is a tremendous addition to the staff who personally learns the name of every child , encourages a positive outlook, and promotes (via dialogues and book groups) learning a la "Mindset" (author: Carol Dweck), offering the perspective that every child can learn and grow--with study and practice. The "Fiske Fundamentals" -- Fair, Inclusive, Safe, Kind, Encouraging -- are promoted. Kids get comment cards from students and staff when they are "caught" demonstrating FISKE fundamentals. The PTO is active and the Kids Care Club -- 15+ year old service organization -- is vibrant and active, introducing kids to social service opportunities via the Food Pantry, Bristol Lodge, and green initiatives. I have had two daughters with very different personalities attend the school and thrive. Opportunities for development: more standard math education (i.e., long division) and improved infrastructure (i.e., roof, health room, cafeteria, newer playground).Parent Review12y ago - Wellesley Middle School
- 6-8
- Public
- 910 Students
8/10GreatSchools RatingParent Rating AverageAfter an amazing experience at Wellesley public schools for elementary school, I entered middle school optimistic and excited. However, I was incredibly disappointed to find that Wellesley Middle School did not at all live up to my expectations. Most teachers seemed disinterested in their work and in teaching students. Little effort was given to support students who had difficulty learning material. Administrators were harsh and unkind to students. Students experiencing discrimination or bullying received next to no help from the school. The unfortunate reality is that Wellesley Middle School is a three year hell, and many other students and parents I have spoken to agree.Other Review1y ago - Wellesley High School
- 9-12
- Public
- 1231 Students
10/10GreatSchools RatingParent Rating AverageThis High School is excellent in that the teaching staff is top notch. There are so many courses to choose from and the individual departments and teacher encourage student to challenge themselves, stretch themselves and not limit them to mid-level course offerings. There seems to be a lot of communication between families, teachers and administration. The communication is open and the atmosphere is positive. Our kids all got great educations and had their choice of top tier colleges. The principal is very open to talking with parents and makes sure that the faculty adopts a similar open policy. I feel like they are concerned with your child and work with the student to achieve success.Parent Review12y ago 
Check out schools near 21 Madison Rd.
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.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
The Lara & Chelsea Collaborative, Coldwell Banker Realty - Wellesley, (781) 237-9090
Agent Phone: (617) 852-7018
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.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.
21 Madison Rd, Wellesley, MA 02481 is a 4 bedroom, 4 bathroom, 2,609 sqft single-family home built in 1940. This property is currently available for sale and was listed by MLS PIN on Jun 3, 2026. The MLS # for this home is MLS# 73529338.