20 Windsor Dr, Ashland, MA 01721
Property image
Property image
OFF MARKET

$732,300

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 2,005 sqft (on 0.35 acres)

20 Windsor Dr, Ashland, MA 01721

Est. Refi. Payment $4,589/mo*
Refinance Your Home
Currently Off Market - Sold Sep 30, 2024 for $699,500

Home Value

Trulia Estimate
$732K
Since last month
Decreased$16K (-2.1%)
Since last year
Increased$15K (+2.1%)
Since last sale
Increased$30K (+4.3%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +91% in the last 10 years
MonthEstimated value
2026
September 2026$730K
August 2026$730K
July 2026$745K
June 2026$739K
May 2026$733K
April 2026$719K
March 2026$711K
February 2026$717K
January 2026$704K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
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
32 Sherborne Cir, Ashland, MA
0.32
Single-Family Home
$907,500
06/30/26
3
2.5
2,209
54 Tri St, Ashland, MA
0.26
Single-Family Home
$610,000
05/11/26
3
1
2,108
373 Eliot St, Ashland, MA
0.18
Single-Family Home
$615,000
05/29/26
3
3.5
1,296
18 Sherborne Cir, Ashland, MA
0.35
Single-Family Home
$882,500
05/01/26
3
3.5
2,607
17 Sewell St, Ashland, MA
0.50
Single-Family Home
$643,000
11/25/25
3
2
2,191
44 Carriage House Path, Ashland, MA
1.05
Single-Family Home
$798,000
06/09/26
3
2
1,732
59 Turner Rd, Holliston, MA
1.11
Single-Family Home
$743,800
01/09/26
3
2
1,960
11 Curve St, Sherborn, MA
0.67
Single-Family Home
$730,000
09/15/26
3
1
1,264

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
12 Windsor Dr, Ashland, MA 01721
0.04
$832,400
3
3
2,128
Off Market
25 Sheffield Dr, Ashland, MA 01721
0.12
$695,000
4
2
1,586
Off Market
Caroline Rd, Ashland, MA 01721
0.08
-
-
-
-
Off Market
1 Adams Rd, Ashland, MA 01721
0.09
$641,200
3
1.5
1,500
Off Market
14 Adams Rd, Ashland, MA 01721
0.15
$657,600
4
4
2,017
Off Market
373 Eliot St, Ashland, MA 01721
0.18
$615,000
3
3.5
1,296
Recently Sold
24 Byron Rd, Ashland, MA 01721
0.18
$929,200
3
2.5
3,222
Off Market
25 Adams Rd, Ashland, MA 01721
0.18
$564,600
2
1
1,260
Off Market
369 Eliot St, Ashland, MA 01721
0.21
$562,000
3
1
1,040
Off Market
363 Eliot St, Ashland, MA 01721
0.21
$1,100,000
9
8
4,814
Recently Sold
37 Annetta Rd, Ashland, MA 01721
0.27
$969,400
4
2.5
2,842
Off Market

Local Information

  • Map ViewExplore the area around 20 Windsor Dr.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1955
0.35 acre lot
2,005 sqft
$365/sqft
4 Open Spaces

About this House

Welcome to this spacious Cape Style home. With 3 bedrooms, 2000 square feet and an incredible vaulted family room off the kitchen, this lovely property has all you are looking for in your new home. As you make your way through the mudroom/breezeway, enter in to the eat in kitchen which flows nicely out to the three season porch or possibly take yourself right in to the bright living room with pellet stove and hardwood floors. Rounding out the home, there are two expansive bedrooms located on the second level and one bedroom on the main level all conveniently located close to a full bath. Beautiful evenings can be spent in the three season porch overlooking the expansive fenced in yard. Run wild around the .35 acres that feel so much larger than that. A full basement w/laundry ensures that all your storage and household needs are taken care of. Property is about one mile from the elementary school and close to shopping and downtown areas of Framingham and Ashland.
20 Windsor Dr, Ashland, MA 01721 is a 3 bedroom, 2 bathroom, 2,005 sqft single-family home built in 1955. It last sold for $699,500 on Sep 30, 2024 (15% above the $607,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $732,300, with a rent estimate of $3,896/month.
Last check for updates: about 7 hours ago
Listed by Amy Uliss, (508) 341-1422
MDM Realty, Inc, (508) 879-8999
Bought with: Kevin Chase, (508) 414-5744, Keller Williams Boston MetroWest, (508) 877-6500
Source: MLS PIN, MLS#73278276

Home Details for 20 Windsor Dr

Interior Features

Interior Details
Basement: FullNumber of Rooms: 6Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Master Bathroom, Bathroom 1, Bathroom 2, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 2005 Square Feet
Appliances & Utilities
Utilities: for Electric Range, for Electric Dryer, Washer HookupAppliances: Electric Water Heater, Range, Dishwasher, Microwave, Refrigerator, Washer, DryerDishwasherDryerLaundry: Electric Dryer Hookup,Washer HookupMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,OilHas CoolingAir Conditioning: Window Unit(s)Has HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Living RoomHas a FireplaceNo Spa
Windows, Doors, Floors & Walls
Flooring: Wood, Tile, Vinyl
Levels, Entrance, & Accessibility
Floors: Wood, Tile, Vinyl

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Porch - EnclosedFencing: FencedExterior: Porch - Enclosed, Fenced YardFoundation: Concrete Perimeter
Parking & Garage
Open Parking Spaces: 4No GarageHas Open ParkingParking Spaces: 4Parking: Paved Drive,Off Street
Frontage
Road Frontage: PublicNot on Waterfront
Water & Sewer
Sewer: Private Sewer

Property Information

Year Built
Year Built: 1955
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape
Building
Construction Materials: FrameNot Attached PropertyDoes Not Include Home Warranty
Property Information
Parcel Number: M:026.0 B:0116 L:0000.0, 3296269

Price & Status

Price
List Price: $607,000
Status Change & Dates
Off Market Date: Sun Sep 01 2024

Active Status

MLS Status: Sold

Location

Direction & Address
City: Ashland
School Information
Elementary School: MindessJr High / Middle School: Ashland MiddleHigh School: Ashland High

Building

Building Area
Building Area: 2005 Square Feet

Community

Community Features: Public Transportation, Shopping, Tennis Court(s), Medical Facility, Laundromat, Conservation Area, House of Worship, Public School, T-StationNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.35 acres

Offer

Contingencies: InspectionListing Terms: Contract

Miscellaneous

BasementMls Number: 73278276

Additional Information

Public TransportationShoppingTennis Court(s)Medical FacilityLaundromatConservation AreaHouse of WorshipPublic SchoolT-Station

Price and Tax history

DateEventPrice
Sep 30, 2024
Source: MLS PIN #73278276
Sold
$699,500
Aug 19, 2024
Source: MLS PIN #73278276
Contingent
$607,000
Aug 15, 2024
Source: MLS PIN #73278276
Listed For Sale
$607,000
Aug 19, 2020
Source: N/A
Sold
$482,500
Jun 24, 2020
Source: Agent Provided
PriceChange
$489,900
Price decreased by 2%

Market trends in Ashland

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
52
5MoM

Around this home

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
    Flag
  • 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

LGBTQ Local Legal Protections

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.

Frequently asked questions about 20 Windsor Dr

  • What is 20 Windsor Dr estimated to be worth?
    Trulia's estimated value for 20 Windsor Dr in Ashland, MA is $732,300.
  • What is the price history for 20 Windsor Dr?
    20 Windsor Dr in Ashland, MA last sold for $699,500 in September 2024.
  • Is Ashland a buyer's or seller's market?
    Ashland is currently a balanced market, based on recent for-sale activity.
  • What do residents say about Ashland?
    Residents describe Ashland, MA as dog-friendly, easy to park in, and pedestrian-friendly. See recently sold homes in Ashland, MA.
  • Does 20 Windsor Dr have air conditioning?
    Yes, 20 Windsor Dr in Ashland, MA has air conditioning.
  • Does 20 Windsor Dr have laundry facilities?
    Yes, 20 Windsor Dr in Ashland, MA has in-unit laundry.

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