20 Rolling Ln, Dover, MA 02030
Property image
Property image
PENDING
1 ACRE

$2,339,999

  • 4 Beds
  • 3.5 Baths
  • 6,153 sqft (on 1 acre)

20 Rolling Ln, Dover, MA 02030

Est. Mortgage $15,243/mo*
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Home Highlights

Single-Family Home
Built in 1975
1 acre lot
$380/sqft
3 Car Garage

Local Information

  • Map ViewExplore the area around 20 Rolling Ln.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:Sophisticated living spacesClassic architectureSpa-like bathGorgeous stone wallsWood-paneled libraryTwo stone patios
Nestled on a private cul-de-sac, this lovely Colonial impresses with its classic architecture, sophisticated living spaces, ideal floor plan and custom millwork throughout. Renovated down to the studs in 2005, the home offers a grand, two-story foyer that leads to an elegant living room and a well-appointed office / study with a fireplace. The eat-in, chef’s kitchen, featuring stainless appliances, white cabinetry and quartz counters, opens to the family room with cathedral ceilings and a wall of windows with views of the lush, professionally-landscaped grounds. A spacious dining room, wood-paneled library, light-filled sun room, large pantry and powder room complete this level. Upstairs the primary suite serves as a true sanctuary with a spa-like bath and walk-in closet. There are three additional bedrooms, two full baths and laundry on this floor. The recently-updated lower level offers additional space for play and exercise, a mud room, access to the three-car garage and ample storage. The exterior boasts a sizable front and back yard, gorgeous stone walls, two stone patios and an outdoor fireplace - ideal for outdoor entertaining and enjoyment. All this plus a new roof, driveway, insulation, EV charger and more! A perfect blend of grand scale, beautiful updates and intimate charm.
Last check for updates: about 7 hours ago
Listing courtesy of Beyond Boston Properties Group, (617) 383-7810
Compass, (781) 365-9954
Source: MLS PIN, MLS#73568111
Also Listed on MLS PIN.

Home Details for 20 Rolling Ln

Interior Features

Interior Details
Basement: Full,Partially Finished,Interior Entry,Garage Access,Radon Remediation SystemNumber of Rooms: 12Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Master Bathroom, Bathroom 1, Bathroom 2, Bathroom 3, Dining Room, Family Room, Kitchen, Living Room, Office
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 6153 Square Feet
Appliances & Utilities
Utilities: for Gas Range, for Electric Dryer, Washer Hookup, Icemaker ConnectionAppliances: Water Heater, Oven, Dishwasher, Microwave, Range, Refrigerator, Washer, Dryer, Wine Refrigerator, Vacuum System, Plumbed For Ice MakerDishwasherDryerLaundry: Flooring - Stone/Ceramic Tile,Electric Dryer Hookup,Recessed Lighting,Washer Hookup,Sink,Second FloorMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,Oil,Fireplace(s),FireplaceHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 3Has a FireplaceNo Spa
Gas & Electric
Electric: Circuit Breakers
Windows, Doors, Floors & Walls
Window: ScreensDoor: French DoorsFlooring: Tile, Carpet, Hardwood, Flooring - Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Wall to Wall Carpet, Flooring - Vinyl
Levels, Entrance, & Accessibility
Floors: Tile, Carpet, Hardwood, Flooring Hardwood, Flooring Stone Ceramic Tile, Flooring Wall To Wall Carpet, Flooring Vinyl
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Porch, PatioFencing: Fenced/Enclosed, FencedExterior: Porch, Patio, Rain Gutters, Professional Landscaping, Sprinkler System, Decorative Lighting, Screens, Fenced Yard, Stone WallFoundation: Concrete PerimeterSprinkler System
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3Open Parking Spaces: 6No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 9Parking: Attached,Garage Door Opener,Workshop in Garage,Paved Drive,Off Street,Driveway,Paved
Frontage
Road Frontage: PublicResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Private Sewer
Finished Area
Finished Area (above surface): 5153Finished Area (below surface): 1000

Days on Market

Days on Market: 28

Property Information

Year Built
Year Built: 1975
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: FrameNot Attached PropertyDoes Not Include Home Warranty
Property Information
Not Included in Sale: Wine Refrigerator In Dining Room Is Available For Purchase.Parcel Number: M:0018 B:00080 L:0000, 79507

Price & Status

Price
List Price: $2,339,999Price Per Sqft: $380
Status Change & Dates
Off Market Date: Sat Sep 12 2026

Active Status

MLS Status: Under Agreement

Location

Direction & Address
City: Dover
School Information
Elementary School: Chickering SchoolJr High / Middle School: Dover Sherborn Middle SchoolHigh School: Dover Sherborn High School

Agent Information

Listing Agent
Listing ID: 73568111

Building

Building Area
Building Area: 6153 Square Feet

Community

Community Features: Shopping, Tennis Court(s), Park, Walk/Jog Trails, Stable(s), Conservation AreaNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 1 Acres

Offer

Contingencies: Pending P&SListing Terms: Contract

Energy

Energy Efficiency Features: Thermostat

Miscellaneous

BasementMls Number: 73568111Above Grade Unfinished Area: 5153

Additional Information

ShoppingTennis Court(s)ParkWalk/Jog TrailsStable(s)Conservation Area

Around this home

What Locals Say about Dover

This October

Trick-or-Treat Score

Built from what locals say about this neighborhood.
  • 100% say there's holiday spirit
  • 74% say neighbors are friendly
  • 71% say there are community events
Trulia Trick or TreatStart Ghost Hunt
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.
  • Ajbellmd
    "Great schools, fantastic library. Not much diversity. "
    0
    Flag
  • 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

Market trends in Dover

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

Home Value

Trulia Estimate
$2.32M
Since last month
Decreased$41K (-1.7%)
Since last year
Increased$173K (+8%)
Since last sale
Increased$221K (+10.5%)
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 +63% in the last 10 years
MonthEstimated value
2026
October 2026$2.32M
September 2026$2.32M
August 2026$2.36M
July 2026$2.25M
June 2026$2.21M
May 2026$2.16M
March 2026$2.14M
February 2026$2.17M
January 2026$2.15M
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
29 Rolling Ln, Dover, MA
0.16
Single-Family Home
$1,360,000
04/10/26
4
3.5
3,305
62 Walpole St, Dover, MA
0.37
Single-Family Home
$1,690,000
07/17/26
4
3.5
5,260
25 Cedar Hill Rd, Dover, MA
0.47
Single-Family Home
$1,550,000
05/07/26
4
3
3,680
5A Valley Rd, Dover, MA
0.17
Single-Family Home
$2,150,000
10/17/25
5
5
7,578
65 Walpole St, Dover, MA
0.31
Single-Family Home
$1,349,000
05/28/26
4
2
2,991
49 Walpole St, Dover, MA
0.36
Single-Family Home
$1,520,000
09/09/26
4
3.5
3,876
5 Bretton Rd, Dover, MA
0.67
Single-Family Home
$1,950,000
07/01/26
4
4
4,452
69 Walpole St, Dover, MA
0.33
Single-Family Home
$1,400,000
07/28/26
3
2
2,512
146 Pine St, Dover, MA
0.69
Single-Family Home
$2,125,000
04/30/26
5
5.5
7,211
5 Powissett St, Dover, MA
0.81
Single-Family Home
$1,700,000
10/17/25
4
3.5
4,848

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
18 Rolling Ln, Dover, MA 02030
0.03
$1,583,300
4
3
3,471
Off Market
22 Rolling Ln, Dover, MA 02030
0.03
$1,416,900
4
2.5
3,193
Off Market
17 Rolling Ln, Dover, MA 02030
0.05
$1,474,600
4
2.5
2,849
Off Market
6 Bryant Ln, Dover, MA 02030
0.06
$2,080,100
5
4
5,392
Off Market
24 Rolling Ln, Dover, MA 02030
0.06
$1,231,800
3
3
2,188
Off Market
19 Rolling Ln, Dover, MA 02030
0.06
$1,786,900
4
4
3,931
Off Market
4 Bryant Ln, Dover, MA 02030
0.07
$1,281,200
3
3
2,662
Off Market
15 Rolling Ln, Dover, MA 02030
0.07
$1,499,500
3
4
3,306
Off Market
26 Rolling Ln, Dover, MA 02030
0.09
$1,280,000
4
3
2,924
Off Market
15 Valley Rd, Dover, MA 02030
0.10
$1,703,800
4
3
3,429
Off Market
21 Rolling Ln, Dover, MA 02030
0.10
$1,475,800
4
2.5
3,365
Off Market
7 Bryant Ln, Dover, MA 02030
0.10
$1,342,200
4
3
2,600
Off Market
23 Rolling Ln, Dover, MA 02030
0.10
$1,786,500
4
3.5
5,107
Off Market
16 Rolling Ln, Dover, MA 02030
0.10
$4,411,200
6
7
9,719
Off Market
17 Valley Rd, Dover, MA 02030
0.11
$1,220,100
4
2
2,866
Off Market
19 Valley Rd, Dover, MA 02030
0.12
$1,312,900
3
3
2,715
Off Market
25 Rolling Ln, Dover, MA 02030
0.12
$1,698,000
3
3
3,369
Off Market
5 Bryant Ln, Dover, MA 02030
0.12
$1,515,300
4
3
3,608
Off Market
13 Valley Rd, Dover, MA 02030
0.13
$1,325,800
3
3
1,842
Off Market
74 Pine St, Dover, MA 02030
0.14
$2,394,300
4
4
5,336
Off Market

Price and Tax history

DateEventPrice
Sep 12, 2026
Source: MLS PIN #73568111
Pending
$2,339,999
Sep 1, 2026
Source: MLS PIN #73568111
Contingent
$2,339,999
Aug 26, 2026
Source: MLS PIN #73568111
Listed For Sale
$2,339,999
Dec 10, 2024
Source: MLS PIN #73265817
Sold
$2,100,000
Oct 31, 2024
Source: William Raveis Real Estate, Mortgage & Insurance #73265817
Pending
$2,199,000

LGBTQ Local Legal Protections

Beyond Boston Properties Group, Compass, (781) 365-9954
Agent Phone: (617) 383-7810
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.

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Frequently asked questions about 20 Rolling Ln

  • What is the estimated monthly payment for 20 Rolling Ln?
    Based on a $2,339,999 list price with 20% down at today's rates, the estimated monthly payment for 20 Rolling Ln in Dover, MA is approximately $15,277 (about $13,213 principal & interest, $1,989 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • 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 homes for sale in Dover, MA.
  • What are the closest schools to 20 Rolling Ln?
    The closest schools to 20 Rolling Ln in Dover, MA are Chickering Elementary School (Pre-K, rated 8/10), Dover-Sherborn Regional High School (rated 10/10), Dover-Sherborn Regional Middle School (rated 9/10).
  • What is 20 Rolling Ln estimated to be worth?
    Trulia's estimated value for 20 Rolling Ln in Dover, MA is $2,317,900.
  • Does 20 Rolling Ln have air conditioning?
    Yes, 20 Rolling Ln in Dover, MA has air conditioning.
  • Does 20 Rolling Ln have laundry facilities?
    Yes, 20 Rolling Ln in Dover, MA has in-unit laundry.
20 Rolling Ln, Dover, MA 02030 is a 4 bedroom, 4 bathroom, 6,153 sqft single-family home built in 1975. This property is currently available for sale and was listed by MLS PIN on Aug 26, 2026. The MLS # for this home is MLS# 73568111.