20 Grayson Rd, Winchester, MA 01890
Property image
Property image
OFF MARKET

$1,995,600

Trulia Estimate
  • 5 Beds
  • 4.5 Baths
  • 3,825 sqft

20 Grayson Rd, Winchester, MA 01890

Est. Refi. Payment $11,877/mo*
Refinance Your Home
Currently Off Market - Sold Sep 16, 2025 for $1,945,000

Home Value

Trulia Estimate
$2M
Since last month
Increased$1K (+0.1%)
Since last year
Increased$136K (+7.3%)
Since last sale
Increased$51K (+2.6%)
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 +162% in the last 10 years
MonthEstimated value
2026
August 2026$2M
August 2026$1.98M
July 2026$1.99M
June 2026$1.96M
May 2026$1.96M
April 2026$1.94M
March 2026$1.94M
February 2026$1.96M
January 2026$1.93M
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
18 Grayson Rd, Winchester, MA
0.01
Single-Family Home
$1,738,000
07/28/26
3
2.5
2,992
10 Bonad Rd, Winchester, MA
0.05
Single-Family Home
$1,620,000
07/06/26
4
2.5
2,233
7 Appalachian Rd, Winchester, MA
0.17
Single-Family Home
$2,150,000
02/02/26
4
4.5
3,263
112 Highland Ave, Winchester, MA
0.19
Single-Family Home
$2,400,000
08/31/26
6
3.5
5,121
15 Englewood Rd, Winchester, MA
0.11
Single-Family Home
$1,425,000
05/07/26
4
3
1,903
9 Wilson St, Winchester, MA
0.26
Single-Family Home
$1,950,000
07/29/26
4
3.5
2,943
6 Abby Rd, Winchester, MA
0.33
Single-Family Home
$2,895,000
10/30/25
5
4.5
5,716
2 Abby Rd, Winchester, MA
0.32
Single-Family Home
$2,575,000
05/14/26
4
4.5
5,614
40 Englewood Rd, Winchester, MA
0.10
Single-Family Home
$1,218,000
05/20/26
4
2
1,841

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 Grayson Rd, Winchester, MA 01890
0.01
$1,738,000
3
2.5
2,992
Recently Sold
14 Bonad Rd, Winchester, MA 01890
0.05
$1,731,800
3
2.5
2,516
Off Market
10 Bonad Rd, Winchester, MA 01890
0.05
$1,620,000
4
2.5
2,233
Recently Sold
32 Grayson Rd, Winchester, MA 01890
0.04
$1,570,400
3
1.5
1,996
Off Market
19 Kenwin Rd, Winchester, MA 01890
0.04
$1,448,400
3
2
1,875
Off Market
29 Kenwin Rd, Winchester, MA 01890
0.07
$1,600,300
4
2
2,132
Off Market
18 Englewood Rd, Winchester, MA 01890
0.08
$1,774,500
5
2.5
2,597
Off Market
40 Englewood Rd, Winchester, MA 01890
0.10
$1,218,000
4
2
1,841
Recently Sold
25 Englewood Rd, Winchester, MA 01890
0.11
$1,785,600
4
4
3,061
Off Market
15 Englewood Rd, Winchester, MA 01890
0.11
$1,425,000
4
3
1,903
Recently Sold
41 Englewood Rd, Winchester, MA 01890
0.12
$1,038,500
3
1.5
1,683
Recently Sold

Local Information

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

Home Highlights

Single-Family Home
Built in 2025
3,825 sqft
$522/sqft
4 Open Spaces

About this House

Another Tree Top Group masterpiece—where natural light, luxury finishes, & thoughtful design come together in perfect harmony. This 5-bed, 4.5-bath new construction home boasts 9+ ft ceilings, exceptional light fixtures, and a stunning waterfall center island that anchors the designer kitchen w/ custom cabinetry that extends to the ceiling. Custom built-ins & storage throughout. A sleek linear fireplace adds warmth to the open-concept family room. With two primary suites to choose from, flexibility meets luxury. The third-floor primary feels like a private hotel retreat w/ a sitting area, dual walk-in closets, & a spa-inspired bath. The second-floor primary offers a spacious en-suite & walk-in closet. Finished lower level includes a fifth bedroom, full bath, wet bar, & bonus living space. Additional highlights: mudroom, EV-charger ready setup, & a rear deck with a spacious backyard. Located minutes from Winchester Center, commuter rail and top-rated schools—this is a rare opportunity!
20 Grayson Rd, Winchester, MA 01890 is a 5 bedroom, 5 bathroom, 3,825 sqft single-family home built in 2025. It last sold for $1,945,000 on Sep 16, 2025 (2% above the $1,899,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,995,600, with a rent estimate of $5,161/month.
Last check for updates: about 13 hours ago
Listed by The Marrocco Group, (781) 799-0666
Coldwell Banker Realty - Lexington, (781) 862-2600
Bought with: Domingo Medina, (617) 610-0050, Coldwell Banker Realty - Lexington, (781) 862-2600
Source: MLS PIN, MLS#73408155

Home Details for 20 Grayson Rd

Interior Features

Interior Details
Basement: Full,Finished,Interior Entry,Sump PumpNumber of Rooms: 15Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Master Bathroom, Bathroom 1, Bathroom 2, Bathroom 3, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3825 Square Feet
Appliances & Utilities
Utilities: for Electric DryerAppliances: Gas Water Heater, Tankless Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Wine CoolerDishwasherDisposalLaundry: In Basement,Electric Dryer HookupMicrowaveRefrigerator
Heating & Cooling
Heating: Forced Air,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Family RoomHas a FireplaceNo Spa
Gas & Electric
Electric: Circuit Breakers, 200+ Amp Service
Windows, Doors, Floors & Walls
Window: Insulated WindowsDoor: Insulated DoorsFlooring: Wood, Tile, Flooring - Stone/Ceramic Tile, Flooring - Hardwood
Levels, Entrance, & Accessibility
Floors: Wood, Tile, Flooring Stone Ceramic Tile, Flooring Hardwood

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Porch, DeckExterior: Porch, DeckFoundation: Concrete Perimeter
Parking & Garage
Open Parking Spaces: 4No GarageHas Open ParkingParking Spaces: 4Parking: Paved Drive,Off Street,Paved
Frontage
Road Frontage: PublicResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 3104Finished Area (below surface): 721

Property Information

Year Built
Year Built: 2025
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: FrameNot Attached PropertyDoes Not Include Home Warranty
Property Information
Parcel Number: M:002 B:0047 L:0, 894595

Price & Status

Price
List Price: $1,899,000
Status Change & Dates
Off Market Date: Tue Aug 12 2025

Active Status

MLS Status: Sold

Location

Direction & Address
City: Winchester
School Information
Elementary School: MuracoJr High / Middle School: MccallHigh School: Whs

Building

Building Area
Building Area: 3825 Square Feet

Community

Community Features: Public Transportation, Walk/Jog Trails, Bike Path, Conservation Area, Highway Access, House of Worship, Public School, T-Station, SidewalksNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 6700 sqft

Offer

Contingencies: Pending P&S

Energy

Energy Efficiency Features: Thermostat

Miscellaneous

BasementMls Number: 73408155Above Grade Unfinished Area: 3104

Additional Information

Public TransportationWalk/Jog TrailsBike PathConservation AreaHighway AccessHouse of WorshipPublic SchoolT-StationSidewalks

Price and Tax history

DateEventPrice
Sep 16, 2025
Source: MLS PIN #73408155
Sold
$1,945,000
Jul 30, 2025
Source: MLS PIN #73408155
Contingent
$1,899,000
Jul 23, 2025
Source: MLS PIN #73408155
Listed For Sale
$1,899,000

Market trends in Winchester

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.47M
$62.83KMoM
Sale-to-List Price
101.9%
0.2%MoM
Price per sq ft
$574
$3MoM
Available listings
64
13MoM

Around this home

What Locals Say about Winchester

At least 93 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 88 % Say yards are well-kept

  • 87 % Say people would walk alone at night

  • 85 % Say parking is easy

  • 79 % Say there are sidewalks

  • 79 % Say car is needed

  • 77 % Say it's walkable to restaurants

  • 77 % Say kids play outside

  • 75 % Say streets are well-lit

  • 74 % Say there's holiday spirit

  • 67 % Say they plan to stay for at least 5 years

  • 67 % Say there's wildlife

  • 66 % Say neighbors are friendly

  • 65 % Say it's walkable to grocery stores

  • 64 % Say it's quiet

  • 54 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Diana P.
    "Winchester is the cutest town, perfect for families. There is Town Say, and Enka, and everything is very family oriented. We even have great pubs/restaurants as well as sub shops, Greek food, nail salons, anything you could want in a home town!"
    7
    Flag
  • Dominic
    "Phenomenal public school system beginning from Kindergarten and extremely welcoming to new residents transferring in."
    0
    Flag
  • Stacie
    "Very family oriented. Not a great neighborhood if you don’t have children. Great, easy commute into the city. Not enough good restaurants that aren’t overpriced though. "
    0
    Flag
  • Yjchoi7
    "Very safe neighborhood.there are often summer events on the common. Teenagers can take train into Boston area fairly easily as there are two stops within Winchester. Fells is a great place for summer walks. "
    2
    Flag
  • Luis B.
    "perfect for my family It is livable stores Closer to me Barbershop computer store Restaurants I will love to buy a house in this area "
    2
    Flag
  • Yjchoiyjchoi
    "It’s very quiet and safe generally. Yet it’s close to Boston and Cambridge city life within a few stops of the commuter from Winchester. "
    0
    Flag
  • Tara
    "I have lived in this neighborhood for 25 years. I love it. Everybody is friendly and kind. The crime is minimal and it’s very quiet. "
    2
    Flag
  • Katie41287
    "I’m not afraid to walk home at 11pm, the town is clean and has plenty of events around town, the people are friendly and it is near public transportation. "
    1
    Flag
  • Anna S.
    "Excellent school Easy commute to Boston Downtown Great parks and pond nearby"
    0
    Flag
  • tod g.
    "Lovely town with easy access to Boston and easy getaway to northern New England."
    0
    Flag
  • jfrancis6
    "Family community built around three streets that form a circle that only has traffic of residents. The area borders the Town of Winchester forest that is great for walks and snow shoeing in winter. All homes are large and attract families were children can safely play and bike in the neighborhood. Many homes have residents who grow up in the neighborhood as children and returned to raise their families. A short walk 4/10 of a mile to train station for those who work in Boston a trip that takes 12 minutes with only one stop. Schools in Winchester are among the best in Massachusetts, a primary attraction to the Town. The Town center is only one mile away and has an addition train station there as well. The Mystic lakes are just beyond the train station with a Town beach and boating opportunities. The Town also borders a 2500 acre forest known as the Fells consisting of the Town water supply and miles of hiking or mountain biking."
    0
    Flag
  • marta3467
    "Can see kids playing ball in street; people walking their dog and Horn Pond and several nice restaurants all within walking distance"
    1
    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 Grayson Rd

  • What is 20 Grayson Rd estimated to be worth?
    Trulia's estimated value for 20 Grayson Rd in Winchester, MA is $1,995,600.
  • What is the price history for 20 Grayson Rd?
    20 Grayson Rd in Winchester, MA last sold for $1,945,000 in September 2025.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winchester?
    The median sale price in Winchester is $1.47M. That is up $62.83K from the prior month.
  • Does 20 Grayson Rd have air conditioning?
    Yes, 20 Grayson Rd in Winchester, MA has air conditioning.
  • Does 20 Grayson Rd have laundry facilities?
    Yes, 20 Grayson Rd in Winchester, MA has laundry facilities.

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