18 Windsor Rd, Dover, MA 02030
Property image
Property image
OFF MARKET

18 Windsor Rd
Dover, MA 02030

  • 5 Beds
  • 3.5 Baths
  • 3,522 sqft (on 1.09 acres)

$1,777,900

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $10,585/mo*
Refinance Your Home

$1,777,900

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $10,585/mo*
Refinance Your Home
5 Beds
3.5 Baths
3,522 sqft
(on 1.09 acres)

Home Value

Trulia Estimate
$1.78M
Since last month
Decreased$11K (-0.6%)
Since last year
Increased$63K (+3.7%)
Since last sale
Increased$584K (+48.7%)
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 +58% in the last 10 years
MonthEstimated value
2026
August 2026$1.78M
July 2026$1.8M
June 2026$1.81M
May 2026$1.8M
April 2026$1.75M
March 2026$1.74M
February 2026$1.68M
January 2026$1.66M
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
36 Yorkshire Rd, Dover, MA
0.20
Single-Family Home
$1,225,000
07/27/26
4
3
3,358
25 Yorkshire Rd, Dover, MA
0.09
Single-Family Home
$1,050,000
12/15/25
4
2.5
2,864
5 Raleigh Rd, Dover, MA
0.21
Single-Family Home
$1,740,000
07/15/26
5
4
3,730
54 Yorkshire Rd, Dover, MA
0.16
Single-Family Home
$1,525,000
06/15/26
4
2.5
3,194
39 Indian Ridge Rd, Natick, MA
0.13
Single-Family Home
$932,500
12/17/25
4
2.5
2,488
12 Greystone Rd, Dover, MA
0.33
Single-Family Home
$1,750,000
07/21/26
4
2.5
3,669
2 Wildwood Rd, Dover, MA
0.37
Single-Family Home
$1,665,000
08/28/25
4
2.5
2,826
23 Indian Ridge Rd, Natick, MA
0.33
Single-Family Home
$975,000
10/28/25
4
2.5
2,298
44 Glen St, Dover, MA
0.39
Single-Family Home
$2,125,000
04/22/26
4
3.5
3,924
61 Glen St, Dover, MA
0.38
Single-Family Home
$2,495,000
05/01/26
4
4.5
5,813

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
25 Yorkshire Rd, Dover, MA 02030
0.09
$1,050,000
4
2.5
2,864
Recently Sold
19 Yorkshire Rd, Dover, MA 02030
0.11
$2,191,600
4
2.5
3,912
Off Market
39 Indian Ridge Rd, Natick, MA 01760
0.13
$932,500
4
2.5
2,488
Recently Sold
28 Yorkshire Rd, Dover, MA 02030
0.10
$1,563,300
4
2.5
2,437
Off Market
8 Raleigh Rd, Dover, MA 02030
0.14
$1,870,900
4
2.5
4,097
Off Market
10 Indian Ridge Rd, Natick, MA 01760
0.18
$1,247,400
4
2.5
2,850
Off Market
32 Indian Ridge Rd, Natick, MA 01760
0.19
$1,127,700
3
3
1,928
Off Market
5 Sherbrooke Dr, Dover, MA 02030
0.14
$2,007,200
5
3.5
4,488
Off Market
54 Yorkshire Rd, Dover, MA 02030
0.16
$1,525,000
4
2.5
3,194
Recently Sold
8 Sherbrooke Dr, Dover, MA 02030
0.16
$1,899,800
4
3.5
3,654
Off Market
50 Yorkshire Rd, Dover, MA 02030
0.18
$2,780,000
4
4
6,670
For Sale
6 Indian Ridge Rd, Natick, MA 01760
0.21
$1,256,000
4
3
2,680
Off Market

Local Information

  • Map ViewExplore the area around 18 Windsor Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1968
Lot Size
1.09 acres
Living Area
3,522 sqft
Price/Sqft
$505
Parking
Garage

About this House

$50,000 price improvement! In heart of beloved Dover neighborhood, 18 Windsor offers suburban living at its best. Inside, gracious, 2 story foyer opens to liv rm w/propane fireplace. Din rm and eat-in kitchen/fam rm both lead to sensational Trex deck overlooking spectacular heated pool. Charming built-ins, counter top seating, second staircase and sliders for everyday alfresco meals are just a few of the features of this main living space. Upstairs, main suite incl. renovated bath w/radiant heat and walk-in closet. Cozy "annex" ideal for nursery or Peloton. As households hunker down, the laundry rm w/ample open shelf storage and delux home office are welcome amenities. 3 generous bedrooms and a pretty double vanity family bath complete this floor. Walk-out LL includes media room, wet bar, abundant storage, ¾ bath and bonus rm. State-of the art Viessman boiler and hot h20 tank, newer AC unit and zero deferred maintenance offer the new owner a turn-key property to enjoy for years to come
18 Windsor Rd, Dover, MA 02030 is a 5 bedroom, 4 bathroom, 3,522 sqft single-family home built in 1968. It last sold for $1,200,000 on Nov 30, 2020. It is currently off market. The Trulia Estimate is $1,777,900, with a rent estimate of $7,160/month.

Home Details for 18 Windsor Rd

Interior Features

Interior Details
BasementNumber of Rooms: 11
Heating & Cooling
Heating: Baseboard, Radiant, Gas, OilAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Wood
Pool
Pool
Parking & Garage
GarageParking Spaces: 8Parking: Garage Attached

Property Information

Year Built
Year Built: 1968Year Updated: 1972
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 1.09 acres

Building

Fitness & Sports
Tennis Court

Price and Tax history

DateEventPrice
Nov 30, 2020
Source: N/A
Sold
$1,200,000
Oct 13, 2020
Source: Agent Provided
Pending
$1,225,000
Oct 5, 2020
Source: Agent Provided
PriceChange
$1,225,000
Price decreased by 4%
Sep 18, 2020
Source: Agent Provided
Listed For Sale
$1,275,000
Jun 29, 2012
Source: N/A
Sold
$940,000

Market trends in Dover

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
24
6MoM

Around this home

What Locals Say about Dover

At least 16 Trulia users voted on each feature.

  • 100 % Say there's holiday spirit

  • 100 % Say car is needed

  • 96 % Say parking is easy

  • 95 % Say there's wildlife

  • 94 % Say yards are well-kept

  • 90 % Say it's dog friendly

  • 89 % Say it's quiet

  • 89 % Say people would walk alone at night

  • 76 % Say they plan to stay for at least 5 years

  • 74 % Say neighbors are friendly

  • 71 % Say there are community events

  • 67 % Say kids play outside

  • 28 % Say it's walkable to grocery stores

  • 25 % Say it's walkable to restaurants

  • 21 % Say streets are well-lit

  • 20 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • James T.
    "The fresh air due to the abundant amount green space, property size and highest rated high school..."
    4
    Flag
  • Jaymz N.
    "Dover is visually beautiful but not a place to live if you are looking for thriving community of shops and restaurants. We only live here to access great public schools. "
    0
    Flag
  • Robin B.
    "I loved visiting my Aunt and Uncle in their beautiful well kept rustic home on this property the few occasions I had to visit my home state. I love the new home even though it is weird for me to imagine that being the property with all of the beautiful trees I had visited. When I was in Dover the whole area was beautiful and safe feeling. It held a lot of my families history. I am not rich, I am disabled and still in my 40's so I probably won't be getting rich but if I were to win tonight's Florida Mega ball I would buy this home and keep it in my family forever, even if I did need to return to Florida during the winter. I love that the area is clean, safe, quiet, and animal friendly, I know at one time a lot of people had horses, one of my aunt's neighbors had sheep, and according to my mom my grandfather had his horses in a nearby stable, he was in the English Hunt Club, I don't have many details about that, My Aunt had a Basset Hound "Ruby" when I was there as a teenager, me and Ruby had found one of my cousins old softballs while roaming in the woods from when they were kids in that home. Ruby tore it up all over the living room and I had to clean it up but it was great fun, that was the only time I got to meet Ruby in her life. I have to mixed breed dogs and if I lived there I would definitely get a horse. I did inherit my families love of animals. I feel that whomever gets this home or any in the area will have a lifetime of priceless memories. "
    5
    Flag
  • lydiaaustin7
    "I live here. It is an open and wooded area, It is fairly remote, but it is a very nice small community. "
    0
    Flag
  • Mary C.
    "Dover MA is the most wonderful town with their #1 School System, great town services, low tax rate, proximity to Boston, safety and cleanliness of the town!"
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 18 Windsor Rd

  • What is 18 Windsor Rd estimated to be worth?
    Trulia's estimated value for 18 Windsor Rd in Dover, MA is $1,777,900.
  • What is the price history for 18 Windsor Rd?
    18 Windsor Rd in Dover, MA last sold for $1,200,000 in November 2020.
  • Is Dover a buyer's or seller's market?
    Dover is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Dover?
    Residents describe Dover, MA as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See recently sold homes in Dover, MA.
  • Does 18 Windsor Rd have air conditioning?
    Yes, 18 Windsor Rd in Dover, MA has air conditioning.
  • Does 18 Windsor Rd have a pool?
    Yes, 18 Windsor Rd in Dover, MA has a pool.

Apartments for Rent

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Off Market Homes Near 18 Windsor Rd

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