4 Windsor Dr, Ashland, MA 01721
OFF MARKET

4 Windsor Dr
Ashland, MA 01721

  • 3 Beds
  • 2 Baths
  • 1,142 sqft (on 0.33 acres)

$641,100

Trulia Estimate
as of Jul 4, 2026
Est. Refi. Payment $3,773/mo*
Refinance Your Home

$641,100

Trulia Estimate
as of Jul 4, 2026
Est. Refi. Payment $3,773/mo*
Refinance Your Home
3 Beds
2 Baths
1,142 sqft
(on 0.33 acres)

Local Information

  • Map ViewExplore the area around 4 Windsor Dr.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This single-family home is located at 4 Windsor Dr, Ashland, MA. 4 Windsor Dr is in Ashland, MA and in ZIP code 01721. This property has 3 bedrooms, 2 bathrooms and approximately 1,142 sqft of floor space. This property has a lot size of 0.33 acres and was built in 1958.
4 Windsor Dr, Ashland, MA 01721 is a 3 bedroom, 2 bathroom, 1,142 sqft single-family home built in 1958. It last sold for $371,000 on Nov 6, 2017. It is currently off market. The Trulia Estimate is $641,100, with a rent estimate of $3,529/month.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 4 Windsor Dr

Interior Features

Heating & Cooling
Heating: OilAir ConditioningHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 6
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1958Year Updated: 1975
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Lot Information

Lot Area: 0.33 acres

Price History for 4 Windsor Dr

DatePriceEventSource
11/06/2017$371,000Sold
N/A
05/04/2010$285,000Sold
N/A
09/01/2009$227,000Sold
N/A

Market trends in Ashland

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
48
4MoM
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Property Tax and Assessment

Year2025
Tax$6,845
Assessment$536,000
Home facts updated by county records

Comparable Sales for 4 Windsor Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1 Adams Rd, Ashland, MA
0.16
Single-Family Home
$630,000
07/18/25
3
1.5
1,500
12 Windsor Dr, Ashland, MA
0.04
Single-Family Home
$810,000
09/29/25
3
3
2,128
16 Sherborne Cir, Ashland, MA
0.36
Single-Family Home
$724,000
10/30/25
3
2
2,097
373 Eliot St, Ashland, MA
0.23
Single-Family Home
$615,000
05/29/26
3
1.5
1,296
32 Sherborne Cir, Ashland, MA
0.34
Single-Family Home
$907,500
06/30/26
3
2.5
2,209
14 Adams Rd, Ashland, MA
0.22
Single-Family Home
$645,000
07/30/25
4
4
2,017
54 Tri St, Ashland, MA
0.32
Single-Family Home
$610,000
05/11/26
3
1
2,108
18 Sherborne Cir, Ashland, MA
0.36
Single-Family Home
$882,500
05/01/26
3
3.5
2,607
37 Annetta Rd, Ashland, MA
0.22
Single-Family Home
$950,000
08/06/25
4
2.5
2,842
17 Sewell St, Ashland, MA
0.58
Single-Family Home
$643,000
11/25/25
3
2
2,191

Nearby homes

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Assigned Schools

These are the assigned schools for 4 Windsor Dr.
View nearby schools on GreatSchools
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 Ashland

At least 91 Trulia users voted on each feature.

  • 92 % Say car is needed

  • 92 % Say it's dog friendly

  • 87 % Say parking is easy

  • 77 % Say people would walk alone at night

  • 75 % Say there's wildlife

  • 74 % Say there are sidewalks

  • 73 % Say there's holiday spirit

  • 73 % Say it's quiet

  • 71 % Say kids play outside

  • 66 % Say neighbors are friendly

  • 62 % Say yards are well-kept

  • 56 % Say it's walkable to restaurants

  • 53 % Say they plan to stay for at least 5 years

  • 43 % Say streets are well-lit

  • 38 % Say it's walkable to grocery stores

  • 30 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Christine.f.graham
    "Kids playing outside every day! Great walkable neighborhoods and outdoor spaces. Farmer's market, The Corner Spot, School & Halloween events. "
    2
    Flag
  • Stephanie
    "There are a lot of irresponsible dog owners that don’t pick up their dogs poop. Some people think they’re dog is friendly and think it’s ok to let them come up to your dog with no control. "
    3
    Flag
  • Kellia E.
    "Quiet friendly community. Close enough to major shopping but just far enough to feel like a getaway from city life. "
    0
    Flag
  • Misssueshair
    "None that I know of It’s a very quiet area Great for walking or running or even riding your bike I think if we had a community pool it would make this area perfect "
    0
    Flag
  • Krisna
    "I’m finding it’s a wonderful little community, here. People look you in the eyes here, are patient and listen and are welcoming. It’s the kind of place where if you’re carrying groceries to your door, but start to your drop bags, someone will offer to help carry them inside for you... and then leave afterwards without hurting you. "
    0
    Flag
  • Christinaandrade100
    "I live in this neighborhood for two years and I loved it. Here is safe, quiet and good for children. The schools are great, because they're a good place and excellent staff. We have too amazing water, square and green spaces to go out."
    0
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  • Sontay
    "The town is very safe and diverse. Plenty of parks for your pet or children. Great schools and plenty of activities to do with your children during warmer months. It’s also fairly close to major highways for a speedy way to get to the city or other locations. Overall great and friendly town. "
    0
    Flag
  • yancen li
    "The ashland mbta and framingham mbta is not far. Bus is nearby also. Generally speaking commute is not a problem. But a car is strongly recommended."
    2
    Flag
  • Nadia
    "Safe, familiar and very good area for children. Schools are very good also. "
    0
    Flag
  • Ducktapedebbie
    " lived here for 25 years the neighborhood is nice and clean people follow the rules and lots of dogs and kids and lots of different ethnic groups and we cohabitate very well. "
    1
    Flag
  • Davis0569 s.
    "I just moved to this area. I really enjoy the life here in Ashland and the people. I have seen some wild Turkey's in the area. "
    1
    Flag
  • Amy
    "It's a lovely neighborhood that's we'll maintained by the condo association. there are beautiful perrenials everywhere. The little avenues and cul de sacs make it feel like a little cape cod village. It is quiet and safe."
    2
    Flag
  • Marabout79
    "Love Ashland, community is tight knit, friendly neighbors quiet neighborhoods. Great school system. "
    0
    Flag
  • Tim M.
    "Ashland is only 25 west of Boston, very easy to get there by car or commuter rail. You also get the feel of a small town that is very easy to get around, plus the schools are rated in the top 50 in Massachusetts. The Ashland Reservior is a gem - swimming, sailing, fishing, and a very nice public beach. Very safe town that is investing in itself even more in the coming years with the Pond Street Project."
    0
    Flag

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Apartments for Rent

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Explore by feature - Pet Friendly

6 pet-friendly rentals in Ashland, MA

Explore by feature - Garage

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Explore by feature - Air Conditioning

14 rentals with air conditioning in Ashland, MA

Explore by feature - Washer/dryer

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Homes for sale near 4 Windsor Dr

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Off Market Homes Near 4 Windsor Dr

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