249 Dover Rd, Westwood, MA 02090
OFF MARKET

249 Dover Rd
Westwood, MA 02090

  • 4 Beds
  • 2.5 Baths
  • 2,574 sqft (on 2.24 acres)

$1,722,000

Trulia Estimate
as of Jun 15, 2026
Est. Refi. Payment $10,093/mo*
Refinance Your Home

$1,722,000

Trulia Estimate
as of Jun 15, 2026
Est. Refi. Payment $10,093/mo*
Refinance Your Home
4 Beds
2.5 Baths
2,574 sqft
(on 2.24 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Distinctive Colonial atop a 2.24 acre private retreat built by premier Westwood builders- Howard bros.Charming century old features such as; leaded glass arched transom entry, architectural staircase, elegant millwork, crystal doorknobs, Butlers pantry all meld perfectly with a modern familys desires; plenty of storage, gorgeous granite counters, high end appliances, decorative lighting, central A/C, newer roof & AMAZING outdoor entertaining space. Gather in the generous Dining Room connected to the stylish Kitchen with custom hutch, upper glass front cabinets, polished ceramic backsplash, lower shaker cabinets with a bright & cozy Breakfast Nook. Curl up to the wood burning stove in the Living Room or relax in the sun drenched Family Room. Enjoy the view from the window seat in the Primary Bedroom complete with Ensuite & WIC. Bedrooms 2 & 3 are joined or separated by a pocket door,4th bdr. on second floor and additional bdr. or flex space on 3rd floor. Open House 5/1 12-1:30.
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
No Info
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 249 Dover Rd

Interior Features

Heating & Cooling
Heating: Forced Air, OilAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 9
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1922
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 2.24 acres

Price History for 249 Dover Rd

DatePriceEventSource
06/29/2022$1,431,000Sold
MLS PIN #72973206
05/04/2022$1,199,000PendingRE/MAX International #72973206
05/04/2022$1,199,000ContingentMLS PIN #72973206
04/28/2022$1,199,000Listed For SaleMLS PIN #72973206
01/31/2008$895,000Sold
N/A

Market trends in Westwood

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
44
3MoM
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Property Tax and Assessment

Year2025
Tax$15,085
Assessment$1,177,600
Home facts updated by county records

Homeowner tools

Estimated monthly rent$6,277/mo
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Homes for rent near 249 Dover Rd

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Comparable Sales for 249 Dover Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
186 Conant Rd, Westwood, MA
0.40
Single-Family Home
$1,342,500
09/26/25
4
2.5
2,273
365 Dover Rd, Westwood, MA
0.31
Single-Family Home
$1,239,000
04/16/26
3
2.5
2,276
47 Dover Rd, Westwood, MA
0.44
Single-Family Home
$1,380,000
05/08/26
4
2.5
2,381
134 High Rock Ln, Westwood, MA
0.14
Single-Family Home
$3,000,000
06/18/25
4
5.5
5,595
360 Dover Rd, Westwood, MA
0.31
Single-Family Home
$1,550,000
07/14/25
6
3.5
4,032
20 Gay St, Westwood, MA
0.54
Single-Family Home
$1,500,000
06/12/26
4
2.5
3,952
162 Mayfair Dr, Westwood, MA
0.91
Single-Family Home
$1,650,000
03/06/26
4
3
3,257
489 High St, Westwood, MA
0.45
Single-Family Home
$876,000
09/30/25
3
2
1,548
29 Summer St, Westwood, MA
0.87
Single-Family Home
$3,000,000
08/04/25
4
3.5
4,237
4 Shoestring Ln, Westwood, MA
0.64
Single-Family Home
$2,150,500
12/12/25
5
3.5
6,091

Nearby homes

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Assigned Schools

These are the assigned schools for 249 Dover Rd.
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The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Westwood

At least 75 Trulia users voted on each feature.

  • 93 % Say car is needed

  • 90 % Say it's dog friendly

  • 90 % Say parking is easy

  • 88 % Say people would walk alone at night

  • 84 % Say yards are well-kept

  • 79 % Say it's quiet

  • 76 % Say there's holiday spirit

  • 73 % Say there's wildlife

  • 71 % Say kids play outside

  • 69 % Say there are sidewalks

  • 68 % Say streets are well-lit

  • 66 % Say they plan to stay for at least 5 years

  • 61 % Say neighbors are friendly

  • 54 % Say there are community events

  • 48 % Say it's walkable to restaurants

  • 42 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Witsele
    "I live in the neighborhood for 5 years and it is very private here. We know some neighbors and they’re very nice."
    0
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  • Arnold_t_pants
    "Plenty of other dog owners in the neighborhood. Definitely a dog friendly neighborhood (although we don’t have dogs, nor like dogs very much). "
    1
    Flag
  • Nikolova68
    "I work in residential houses I love Westwood is safe and fun . Everything is good and I enjoy everything about Westwood "
    0
    Flag
  • Cc
    "Love our Weatherbee neighborhood!!! Quiet wide streets. Accessible to stores / highway : commuter rail."
    1
    Flag
  • Tina A.
    "Easy streets to walk your dog, quiet friendly neighborhood, safe environment. May not like lack of lights in certain neighborhoods"
    1
    Flag
  • Danielle.drayton
    "Good schools, safe, easy highway access. Close to neighboring city centers of Dedham, Medfield, and Norwood"
    1
    Flag
  • Emilee.a.donovan
    "I don’t commute, I work from home so I can’t comment but if I did I would take the train from Norwood into the city."
    0
    Flag
  • Melissa_mips
    "Memorial Day parade, Seniors night, Westwood day, farmers market, Hale reservation, community classes, "
    0
    Flag
  • Chris P.
    "Great schools. Great neighbors. Close to major highways and commuter rail. Recently added shopping centers are great. "
    0
    Flag
  • Emilee.a.donovan
    "Westwood Day every year is very fun and has a lot of local vendors! Great for families. There is a play area and petting zoo for kids. Great way to experience the community! We also have a lot of small farmers markets in the summer. "
    1
    Flag
  • Chris P.
    "I don’t commute to work. I work from home. From what I heard/saw, rush hour traffic can be pretty hectic. "
    0
    Flag
  • Meri T.
    "The area is convenient to highways and shopping, library and parks for kids. Ice cream and food. Lovely area for any age"
    1
    Flag
  • Melissa_mips
    "Great schools, growing businesses opportunities and balance of conservation/protected land. Less than 15 miles from Boston "
    0
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  • Melissa_mips
    "Close to great schools and Hale reservation. Beautiful homes close to Boston but you would never know it’s only 12 miles from town."
    0
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  • hayhelen
    "I've lived in Westwood for almost 30 years. Excellent public school system. Friendly neighborhoods. Hop onto Rte. 128 or I-95. Only 15 minutes from Massachusetts Turnpike. Commuter Rail to Boston gets you there in 20 minutes. Can't beat that! Good restaurants and shopping minutes away at Legacy Place in Dedham."
    0
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  • trulyapain
    "I have lived here over 25 yrs.. Pretty, peaceful, lots of greenery, though no sidewalks on most streets ,many lights out at night. Not safe for walking-very few crossing lights in high traffic areas. Be aware of inflated property estimates by town assessor, thus high taxes on all homes. Suitable for those with school age children as schools are the main focus here. Library is incredible and is being rebuilt. People in general are friendly and helpful and good neighbors. It is fine for couples and retirees with deep pockets. Boring for singles. "
    0
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Homes for sale near 249 Dover Rd

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Off Market Homes Near 249 Dover Rd

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249 Dover Rd, Westwood, MA 02090 is a 4 bedroom, 3 bathroom, 2,574 sqft single-family home built in 1922. This property is not currently available for sale. 249 Dover Rd was last sold on Jun 29, 2022 for $1,431,000. The current Trulia Estimate for 249 Dover Rd is $1,722,000.