21 Chiltern Rd
Weston, MA 02493
4 Beds
4 Baths
4,520 sqft (on 0.71 acres)
4 Beds
4 Baths
4,520 sqft
(on 0.71 acres)
Homes for sale near 21 Chiltern Rd
OFF MARKET- OFF MARKET
- OFF MARKET
- OFF MARKET
- OFF MARKETThe Lara & Chelsea Collaborative, Coldwell Banker Realty - Wellesley
- OFF MARKET
- Donahue Maley and Burns Team, Compass
- OFF MARKET
- OFF MARKET
- OFF MARKET
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Apartments for Rent
- NEW - 1 DAY AGOPET FRIENDLYTotal price$2,935 - $8,832/moStudio-3 bd1-2 baThe Nines | 40 William St #656,
Wellesley Hills, MA 02481 - PET FRIENDLYINCOME RESTRICTED$3,670 - $6,741/moFees may apply1-3 bd1-3 baWoodland Station Apartments | 1940 Washington St #120,
Auburndale, MA 02466 - PET FRIENDLYTotal price$3,928 - $4,559/mo2 bd2-3 baHastings Village | 66 Hastings St #205,
Wellesley Hills, MA 02481 - PET FRIENDLY$2,250 - $2,700/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 baPhillip's Park | 324 Washington St #208,
Wellesley Hills, MA 02481 - PET FRIENDLY$2,700 - $2,900/moFees may apply2 bd1 baHamilton Highlands | 757 Highland Ave #309S,
Needham Heights, MA 02494 - PET FRIENDLY$2,250 - $2,650/moFees may apply1-2 bd1 baLexington St Apartments | 89 Lexington St #6ce1f48ab,
Auburndale, MA 02466 - APPLY INSTANTLYPET FRIENDLY
- APPLY INSTANTLYPET FRIENDLY
- APPLY INSTANTLYPET FRIENDLY
- APPLY INSTANTLYPET FRIENDLY
- APPLY INSTANTLYPET FRIENDLY
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Local Information
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Description
executive ranch with oversized rooms
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.
Home Highlights
Parking
Garage
Outdoor
Patio, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info
Home Details for 21 Chiltern Rd
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Interior Details BasementAtticNumber of Rooms: 12Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Master Bath, Office, Recreation Room |
Heating & Cooling Heating: Baseboard, Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Baseboard |
Levels, Entrance, & Accessibility Stories: 2Floors: Tile, Hardwood |
Appliances & Utilities Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher |
Fireplace & Spa Fireplace |
Windows, Doors, Floors & Walls Double Paned Windows |
Security Security System |
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Exterior Home Features Roof: AsphaltDeckExterior: BrickLawnPatioSprinkler System |
Parking & Garage GarageParking Spaces: 2Parking: Garage Attached, Off Street |
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Year Built Year Built: 1957Year Updated: 2016 |
Property Type / Style Property Type: Single Family HomeArchitecture: Ranch / Rambler |
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Units in Building: 1 |
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Lot Area: 0.71 acres |
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Sport Court |
Price History for 21 Chiltern Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 07/08/2016 | $1,259,300 | Sold | N/A |
| 05/07/2016 | $1,339,000 | Pending | Agent Provided |
| 03/29/2016 | $1,339,000 | PriceChange | Agent Provided |
| 02/10/2016 | $1,379,000 | Listed For Sale | Agent Provided |
| 09/27/2015 | $1,379,000 | ListingRemoved | Agent Provided |
| 09/19/2015 | $1,379,000 | PriceChange | Agent Provided |
| 08/15/2015 | $1,450,000 | Listed For Sale | Agent Provided |
| 02/15/2013 | $725,000 | Sold | N/A |
| 12/21/2012 | $829,000 | Listed For Sale | Agent Provided |
| 12/02/2011 | $899,000 | ListingRemoved | Agent Provided |
| 04/12/2011 | $899,000 | Listed For Sale | Agent Provided |
| 11/04/2010 | $985,000 | ListingRemoved | Agent Provided |
| 08/19/2010 | $985,000 | Listed For Sale | Agent Provided |
| 07/03/2010 | $1,289,000 | ListingRemoved | Agent Provided |
| 06/26/2009 | $1,289,000 | PriceChange | Agent Provided |
| 02/20/2009 | $1,379,900 | Listed For Sale | Agent Provided |
| 12/06/2008 | $1,379,900 | ListingRemoved | Agent Provided |
| 10/05/2008 | $1,379,900 | Listed For Sale | Agent Provided |
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $19,815 |
| Assessment | $1,785,100 |
Home facts updated by county records
Comparable Sales for 21 Chiltern Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.20 | Single-Family Home | $2,960,000 | 05/15/25 | 4 | 5 | 4,624 | |
0.31 | Single-Family Home | $2,050,000 | 09/03/25 | 4 | 5 | 4,442 | |
0.14 | Single-Family Home | $1,975,000 | 01/06/26 | 5 | 4 | 2,614 | |
0.31 | Single-Family Home | $2,299,000 | 11/10/25 | 4 | 3.5 | 4,200 | |
0.21 | Single-Family Home | $2,800,000 | 07/02/25 | 5 | 5.5 | 4,361 | |
0.40 | Single-Family Home | $1,880,000 | 07/16/25 | 4 | 2.5 | 2,713 | |
0.43 | Single-Family Home | $2,100,000 | 10/15/25 | 4 | 3.5 | 3,220 | |
0.64 | Single-Family Home | $1,200,000 | 08/27/25 | 5 | 3.5 | 2,864 | |
0.49 | Single-Family Home | $3,475,000 | 07/31/25 | 5 | 5.5 | 5,359 | |
0.50 | Single-Family Home | $2,205,000 | 08/14/25 | 5 | 3.5 | 3,241 |
Assigned Schools
These are the assigned schools for 21 Chiltern Rd.
- Field Elementary School
- 4-5
- Public
- 337 Students
8/10GreatSchools RatingParent Rating AverageMy daughter has completed the first half of fourth grade, and we've been impressed with the principal, her homeroom teacher, teacher specialists, and the beautiful school facility itself. Field Elementary has some of the highest math scores in the state, and we particularly like the emphasis on social- emotional learning, which leverages the Responsive Classroom approach. The engagement of parents, in support of the teachers, is extremely strong.Parent Review6y ago - Weston Middle School
- 6-8
- Public
- 454 Students
8/10GreatSchools RatingParent Rating AverageWeston is amazing. They give so many resources to students. Not only that, there are a lot of after-school activities you can do, and they also offer transportation till 5:30. For example, there is a swimming pool at the Weston Middle School where the Weston swim teams train in every weekOther Review7mo ago - Country Elementary School
- PK-3
- Public
- 335 Students
10/10GreatSchools RatingParent Rating AverageOur kids have had an extremely positive experience at Country. We love the teachers and the principal.Parent Review2y ago - Weston High School
- 9-12
- Public
- 651 Students
10/10GreatSchools RatingParent Rating AverageThis school keeps declining due to a SC that continues to be comprised of parents who only want to please school administration. The relationship between the school committee and the superintendent is troubling, to say the least. The superintendent is completely uninterested in doing what is best for the students and Only rains to do what is easiest for her and for the teachers. She was unqualified and hastily appointed when no other candidates accepted the job. Think twice before moving here for the school system. Things look good on the surface but all parents here have their children individually tutored and/or send them to enrichment classes to keep them up to speed. It’s a town and a school system with a lot of money but not a lot of academic rigor. Simply look at some of the department heads and how pedestrian they are. It seems if you have enough years as a teacher you automatically get promoted and are responsible for running a department ( with no experience!) and making important decisions that negatively impact the student community. There are many good school systems out there: Wellesley, Newton, Brookline and Wayland to name a few. Do your research. Don’t bother talking to school committee members because they will just feed you some tired, prepared line. Look very closely at the test scores. Weston falls short.Parent Review3y ago - Woodland Elementary School
- PK-3
- Public
- 302 Students
10/10GreatSchools RatingParent Rating AverageGreat school with supportive teachers and parents.Parent Review5y ago 
Check out schools near 21 Chiltern Rd.
What Locals Say about Weston
At least 28 Trulia users voted on each feature.
90 % Say car is needed
85 % Say it's dog friendly
82 % Say it's quiet
80 % Say parking is easy
77 % Say people would walk alone at night
76 % Say there's holiday spirit
74 % Say they plan to stay for at least 5 years
73 % Say yards are well-kept
71 % Say there's wildlife
52 % Say kids play outside
50 % Say neighbors are friendly
44 % Say there are community events
38 % Say there are sidewalks
33 % Say it's walkable to grocery stores
29 % Say streets are well-lit
26 % Say it's walkable to restaurants
Learn more about our methodology.
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Homes for rent near 21 Chiltern Rd
- APPLY INSTANTLYFURNISHED
- NEW - 3 HRS AGO
- NEW - 2 DAYS AGOPET FRIENDLY
- APPLY INSTANTLY
- APPLY INSTANTLY
- PET FRIENDLY
- See more homes for rent inWeston
Off Market Homes Near 21 Chiltern Rd
- SOLDMAY 8, 2026Migdol Moore Team, Gibson Sotheby's International Realty
- SOLDMAY 8, 2026The Varano Realty Group, Keller Williams Realty
- SOLDMAY 8, 2026Rob and Meaghan, Hawthorn Properties
- SOLDMAY 8, 2026Zack Harwood Real Estate Group, Berkshire Hathaway HomeServices Warren Residential
- SOLDMAY 7, 2026Anya Kogan, Luxury Realty Partners
- SOLDMAY 7, 2026Simon Gray, Coldwell Banker Realty - Newton
- SOLDMAY 6, 2026Patrick Mulligan, Northeast Realty + Co.
- SOLDMAY 6, 2026Paul Neavyn, Gibson Sotheby's International Realty
- SOLDMAY 6, 2026Denise Mosher, Coldwell Banker Realty - Weston
- SOLDMAY 6, 2026Dean Wilde, Berkshire Hathaway HomeServices Commonwealth Real Estate
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21 Chiltern Rd, Weston, MA 02493 is a 4 bedroom, 4 bathroom, 4,520 sqft single-family home built in 1957. This property is not currently available for sale. 21 Chiltern Rd was last sold on Jul 8, 2016 for $1,259,300. The current Trulia Estimate for 21 Chiltern Rd is $2,201,000.