21 Windsor Rd
Wellesley, MA 02481
6 Beds
4 Baths
4,954 sqft (on 0.54 acres)
6 Beds
4 Baths
4,954 sqft
(on 0.54 acres)
Local Information
© Google
-- mins to
Description
Built in 1913, this stately stucco colonial is located in the sought-after Country Club neighborhood and offers classic charm with modern day conveniences. 12 gracious rooms, 6 bedrooms, 3 full baths, and 2 half baths sit on more than a half-acre of land. The elegant first floor with high ceilings & exposed beams includes a renovated kitchen, large formal dining room, expansive front-to-back family room, and cozy sunroom. The second floor can be accessed via the front or back staircase and enjoys 4 bedrooms & 2 full baths. The fully finished third floor has an additional bedroom & full bath, plus a huge bonus room/6th bedroom. There’s ample storage in the basement as well as a private office. With close proximity to the middle school & high school, the Wellesley Hills train stop, and the Mass Pike & Rte 95, this timeless treasure is ideally located for today's urban/suburban lifestyle!
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. This description is from November 03, 2023
Home Highlights
Parking
Garage
Outdoor
Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
134 days ago
Home Details for 21 Windsor Rd
|
|---|
Interior Details Basement: Full,Partially Finished,Walk-Out Access,Sump PumpNumber of Rooms: 12Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Master Bathroom, Bathroom 1, Bathroom 2, Bathroom 3, Dining Room, Family Room, Kitchen, Living Room |
Beds & Baths Number of Bedrooms: 6Number of Bathrooms: 5Number of Bathrooms (full): 3Number of Bathrooms (half): 2 |
Dimensions and Layout Living Area: 4954 Square Feet |
Appliances & Utilities Utilities: for Gas Range, for Electric Dryer, Washer HookupAppliances: Gas Water Heater, Range, Dishwasher, Disposal, Refrigerator, Freezer, Washer, Dryer, Range HoodDishwasherDisposalDryerLaundry: In Basement,Electric Dryer Hookup,Washer HookupRefrigeratorWasher |
Heating & Cooling Heating: Baseboard,Natural Gas,Fireplace(s)Has CoolingAir Conditioning: Window Unit(s)Has HeatingHeating Fuel: Baseboard |
Fireplace & Spa Number of Fireplaces: 4Fireplace: Family Room, Living Room, BedroomHas a FireplaceNo Spa |
Windows, Doors, Floors & Walls Flooring: Tile, Carpet, Hardwood, Flooring - Hardwood |
Levels, Entrance, & Accessibility Floors: Tile, Carpet, Hardwood, Flooring Hardwood |
|
|---|
Exterior Home Features Roof: SlatePatio / Porch: PatioExterior: Patio, Professional Landscaping, Sprinkler System, Garden, Stone WallFoundation: Concrete PerimeterGardenSprinkler System |
Parking & Garage Number of Garage Spaces: 1Number of Covered Spaces: 1Open Parking Spaces: 6No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 7Parking: Detached,Paved Drive,Off Street |
Frontage Road Frontage: PublicNot on Waterfront |
Water & Sewer Sewer: Public Sewer |
|
|---|
Year Built Year Built: 1913 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial |
Building Construction Materials: FrameNot Attached PropertyDoes Not Include Home Warranty |
Property Information Not Included in Sale: Excludes Sunroom Chandelier, Mounted Tvs, Washers, Dryer & Refrigerator In Basement.Parcel Number: M:056 R:036 S:, 258720 |
|
|---|
Price List Price: $2,565,000 |
Status Change & Dates Off Market Date: Mon Aug 28 2023 |
|
|---|
MLS Status: Sold |
|
|---|
Direction & Address City: WellesleyCommunity: Country Club |
School Information Elementary School: WpsJr High / Middle School: WmsHigh School: Whs |
|
|---|
Building Area Building Area: 4954 Square Feet |
|
|---|
Community Features: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Golf, Conservation Area, Highway Access, Private School, Public School, T-Station, UniversityNot Senior Community |
|
|---|
No HOA |
|
|---|
Lot Area: 0.54 acres |
|
|---|
Contingencies: Financing |
|
|---|
BasementMls Number: 73146566 |
|
|---|
Public TransportationShoppingTennis Court(s)ParkWalk/Jog TrailsGolfConservation AreaHighway AccessPrivate SchoolPublic SchoolT-StationUniversity |
Last check for updates: about 11 hours ago
Listed by The Madden David Real Estate Group, (617) 610-5057
Coldwell Banker Realty - Wellesley, (781) 237-9090
Bought with: The Lara & Chelsea Collaborative, (617) 852-7018, Gibson Sotheby's International Realty, (781) 237-8181
Source: MLS PIN, MLS#73146566
Price History for 21 Windsor Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 11/03/2023 | $2,335,000 | Sold | MLS PIN #73146566 |
| 08/15/2023 | $2,565,000 | Contingent | MLS PIN #73146566 |
| 08/09/2023 | $2,565,000 | Listed For Sale | MLS PIN #73146566 |
| 06/07/2019 | $1,875,000 | Sold | N/A |
| 03/30/2019 | $1,995,000 | Pending | Agent Provided |
| 02/06/2019 | $1,995,000 | Listed For Sale | Agent Provided |
| 12/04/2018 | $1,995,000 | ListingRemoved | Agent Provided |
| 09/05/2018 | $1,995,000 | Listed For Sale | Agent Provided |
- Results are loading
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $24,405 |
| Assessment | $2,374,000 |
Home facts updated by county records
Comparable Sales for 21 Windsor Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.19 | Single-Family Home | $2,600,000 | 01/09/26 | 4 | 3.5 | 3,705 | |
0.31 | Single-Family Home | $2,335,000 | 07/01/25 | 5 | 3.5 | 4,635 | |
0.15 | Single-Family Home | $2,900,000 | 07/24/25 | 4 | 4.5 | 3,272 | |
0.36 | Single-Family Home | $2,625,000 | 11/03/25 | 4 | 3.5 | 4,720 | |
0.40 | Single-Family Home | $2,354,000 | 12/24/25 | 4 | 4.5 | 4,211 | |
0.39 | Single-Family Home | $3,300,000 | 08/08/25 | 6 | 5.5 | 4,897 | |
0.14 | Single-Family Home | $6,187,500 | 11/12/25 | 6 | 7 | 7,037 | |
0.42 | Single-Family Home | $2,700,000 | 09/03/25 | 6 | 4.5 | 7,830 | |
0.39 | Single-Family Home | $2,625,000 | 04/30/26 | 4 | 3.5 | 3,433 | |
0.67 | Single-Family Home | $2,500,000 | 04/13/26 | 5 | 4.5 | 5,261 |
Assigned Schools
These are the assigned schools for 21 Windsor 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 Review11y 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 Windsor Rd.
What Locals Say about Wellesley
At least 123 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
76 % 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
62 % Say it's walkable to grocery stores
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Apartments for Rent
PET FRIENDLYTotal price$2,530 - $8,104/moStudio-3 bd1-2 baThe Nines | 40 William St #460,
Wellesley Hills, MA 02481
NEW - 1 DAY AGOPET FRIENDLYTotal price$2,590 - $5,450/moStudio-3 bd1-2 baThe Kendrick | 275 2nd Ave #5089,
Needham Heights, MA 02494
$2,375 - $3,300/moFees may applyStudio-2 bd1-2 baHamilton Highlands | 757 Highland Ave #124N,
Needham Heights, MA 02494
PET FRIENDLY$2,607 - $6,244/moFees may applyStudio-3 bd1-2 baThe Aven at Newton Highlands | 99 Needham St #1107,
Newton Highlands, MA 02461
PET FRIENDLYINCOME RESTRICTED$3,740 - $6,401/moFees may apply1-3 bd1-3 baWoodland Station Apartments | 1940 Washington St #120,
Auburndale, MA 02466
PET FRIENDLYFURNISHEDTotal price$2,900 - $4,138/mo1-2 bd1-2 baCharles River Landing | 300 2nd Ave #4172,
Needham Heights, MA 02494
$2,250 - $2,800/moFees may applyStudio-2 bd1 baWoodland Park | 264 Grove St #2,
Auburndale, MA 02466
APPLY INSTANTLYPET FRIENDLYTotal price$3,500 - $3,995/mo2 bd1-2 baPhilips' Park | 324 Washington St #208,
Wellesley Hills, MA 02481
PET FRIENDLYTotal price$4,078 - $4,559/mo2 bd2-3 baHastings Village | 66 Hastings St #205,
Wellesley Hills, MA 02481
NEW - 2 DAYS AGOAPPLY INSTANTLYPET FRIENDLY
APPLY INSTANTLYPET FRIENDLY
See more homes for rent inWellesley
Explore by feature
- SPECIAL OFFERPET FRIENDLYTotal price$2,530 - $8,104/moStudio-3 bd1-2 baThe Nines | 40 William St #460,
Wellesley Hills, MA 02481 - SPECIAL OFFERPET FRIENDLYTotal price$4,078 - $4,559/mo2 bd2-3 baHastings Village | 66 Hastings St #205,
Wellesley Hills, MA 02481 - APPLY INSTANTLYSPECIAL OFFERPET FRIENDLYTotal price$3,500 - $3,995/mo2 bd1-2 baPhilips' Park | 324 Washington St #208,
Wellesley Hills, MA 02481 - NEW - 2 DAYS AGOAPPLY INSTANTLYPET FRIENDLY
PET FRIENDLY
PET FRIENDLY
PET FRIENDLY
NEW - 2 DAYS AGOAPPLY INSTANTLYPET FRIENDLYFURNISHED
APPLY INSTANTLYPET FRIENDLY
PET FRIENDLYFURNISHED
Homes for sale near 21 Windsor Rd
OFF MARKETThe Pinnacle Group, Douglas Elliman Real Estate - Wellesley
1.15 ACRESBeth Dickerson, Gibson Sotheby's International Realty
FORECLOSURE0.46 ACRESTimothy E. Driscoll, South Shore Sotheby's International Realty
0.56 ACRESChristine Norcross & Partners, William Raveis R.E. & Home Services
0.31 ACRESJohn Saleh, Centre Realty Group
0.54 ACRESThe Shahani Group, Compass
0.64 ACRESChristine Norcross & Partners, William Raveis R.E. & Home Services
OPEN WED, 5:30-6:30PM0.47 ACRESCara Rogers, NorthStar Real Estate, LLC
See more homes for sale inWellesley
Off Market Homes Near 21 Windsor Rd
SOLDMAY 19, 2026The Kennedy Lynch Team, Hammond Residential Real Estate
SOLDMAY 19, 2026Betsy Kessler, Rutledge Properties
SOLDMAY 19, 2026Carina Bittar-Doyle, William Raveis R. E. & Home Services
SOLDMAY 18, 2026The Morgan Franklin Group, Coldwell Banker Realty - Boston
SOLDMAY 18, 2026Brenda van der Merwe, Hammond Residential Real Estate
SOLDMAY 18, 2026Chaplin Partners, Compass
SOLDMAY 18, 2026Steve Leavey, Keller Williams Realty
SOLDMAY 18, 2026Maura Cutting, Charlesgate Realty Group LLC
SOLDMAY 15, 2026The Denman Group, eXp Realty
SOLDMAY 15, 2026Ezra Stillman, Hammond Residential Real Estate- See more homes for sale inWellesley
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.
Homes for rent near 21 Windsor Rd
- Results are loading
21 Windsor Rd, Wellesley, MA 02481 is a 6 bedroom, 5 bathroom, 4,954 sqft single-family home built in 1913. This property is not currently available for sale. 21 Windsor Rd was last sold on Nov 3, 2023 for $2,335,000 (9% lower than the asking price of $2,565,000). The current Trulia Estimate for 21 Windsor Rd is $2,978,500.