18 Windsor Rd, Dover, MA 02030
OFF MARKET

18 Windsor Rd
Dover, MA 02030

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

$1,782,600

Trulia Estimate
as of May 22, 2026
Est. Refi. Payment $10,585/mo*
Refinance Your Home

$1,782,600

Trulia Estimate
as of May 22, 2026
Est. Refi. Payment $10,585/mo*
Refinance Your Home
5 Beds
3.5 Baths
3,522 sqft
(on 1.09 acres)

Local Information

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

Description

$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
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
Deck, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

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 History for 18 Windsor Rd

DatePriceEventSource
11/30/2020$1,200,000Sold
N/A
10/13/2020$1,225,000PendingAgent Provided
10/05/2020$1,225,000PriceChange
Agent Provided
09/18/2020$1,275,000Listed For SaleAgent Provided
06/29/2012$940,000Sold
N/A
04/25/2012$1,050,000Listed For SaleAgent Provided
09/29/2006$810,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$16,615
Assessment$1,474,300
Home facts updated by county records

Comparable Sales for 18 Windsor Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
25 Yorkshire Rd, Dover, MA
0.09
Single-Family Home
$1,050,000
12/15/25
4
2.5
2,864
5 Sherbrooke Dr, Dover, MA
0.14
Single-Family Home
$1,950,000
06/11/25
5
3.5
4,488
6 Indian Ridge Rd, Natick, MA
0.21
Single-Family Home
$1,250,000
05/28/25
4
3
2,680
39 Indian Ridge Rd, Natick, MA
0.13
Single-Family Home
$932,500
12/17/25
4
2.5
2,488
207 Glen St, Natick, MA
0.36
Single-Family Home
$1,493,000
05/23/25
5
4
4,277
2 Yorkshire Rd, Dover, MA
0.32
Single-Family Home
$1,725,000
08/08/25
4
3
4,275
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
11 Sassamon Rd, Natick, MA
0.61
Single-Family Home
$2,010,000
05/28/25
5
4
4,366

Nearby homes

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Assigned Schools

These are the assigned schools for 18 Windsor Rd.
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 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
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  • 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
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Apartments for Rent

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Homes for sale near 18 Windsor Rd

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Off Market Homes Near 18 Windsor Rd

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Homes for rent near 18 Windsor Rd

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18 Windsor Rd, Dover, MA 02030 is a 5 bedroom, 4 bathroom, 3,522 sqft single-family home built in 1968. This property is not currently available for sale. 18 Windsor Rd was last sold on Nov 30, 2020 for $1,200,000. The current Trulia Estimate for 18 Windsor Rd is $1,782,600.