27 Ledyard Rd, Winchester, MA 01890
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Property image
OFF MARKET

27 Ledyard Rd
Winchester, MA 01890

  • 3 Beds
  • 1.5 Baths
  • 2,364 sqft (on 0.28 acres)

$2,608,600

Trulia Estimate
as of Jul 9, 2026
Est. Refi. Payment $15,544/mo*
Refinance Your Home

$2,608,600

Trulia Estimate
as of Jul 9, 2026
Est. Refi. Payment $15,544/mo*
Refinance Your Home
3 Beds
1.5 Baths
2,364 sqft
(on 0.28 acres)

Local Information

  • Map ViewExplore the area around 27 Ledyard Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Discover the endless potential of this charming 3-bedroom, 1.5-bathroom home, perfectly positioned on a sought-after Winchester lot with excellent frontage and a generously sized yard. The finished lower level features a convenient walkout to a private backyard, creating additional living space and ample opportunities for outdoor enjoyment. This property presents a fantastic opportunity for a full renovation or teardown, allowing you to design and construct your dream home from the ground up. Situated near top-tier schools, a variety of convenient amenities, and the scenic Middlesex Fells Conservation area, this location offers the best of both worlds—serenity and accessibility. Don't miss the chance to create a custom living space in a prime location that caters to your lifestyle and preferences. Embrace this unique opportunity to bring your vision to life and make this desirable Winchester address your own.
27 Ledyard Rd, Winchester, MA 01890 is a 3 bedroom, 2 bathroom, 2,364 sqft single-family home built in 1940. It last sold for $1,380,000 on Sep 4, 2024 (15% above the $1,200,000 asking price). More recently, it was listed as a rental in December 2017 with an asking price of $2,950 per month. That rental listing was removed on January 13, 2018. It is currently off market. The Trulia Estimate is $2,608,600, with a rent estimate of $4,955/month.

Home Highlights

Parking
1 Car Garage
Outdoor
Porch
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 27 Ledyard Rd

Interior Features

Interior Details
Basement: Full,Finished,Walk-Out Access,Garage AccessNumber of Rooms: 7Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bathroom 1, Bathroom 2, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (half): 1Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 2364 Square Feet
Appliances & Utilities
Utilities: for Electric Range, for Electric DryerAppliances: Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, DryerDishwasherDisposalDryerLaundry: Flooring - Stone/Ceramic Tile,Main Level,Lighting - Overhead,First Floor,Electric Dryer HookupMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Central,Forced Air,Natural GasHas CoolingAir Conditioning: Window Unit(s)Has HeatingHeating Fuel: Central
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Living RoomHas a FireplaceNo Spa
Gas & Electric
Electric: 110 Volts
Windows, Doors, Floors & Walls
Window: Insulated Windows, ScreensDoor: Insulated DoorsFlooring: Wood
Levels, Entrance, & Accessibility
Floors: Wood

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Porch, Porch - Enclosed, ScreenedExterior: Porch, Porch - Enclosed, Porch - Screened, Rain Gutters, Professional Landscaping, Decorative Lighting, Screens, Stone WallFoundation: Concrete Perimeter, Block
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1Open Parking Spaces: 4No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 5Parking: Attached,Under,Paved Drive,Off Street,Paved
Frontage
Road Frontage: PublicRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Property Information

Year Built
Year Built: 1940
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape
Building
Construction Materials: FrameNot Attached PropertyDoes Not Include Home Warranty
Property Information
Not Included in Sale: NoneParcel Number: M:006 B:0281 L:0, 896035

Price & Status

Price
List Price: $1,200,000
Status Change & Dates
Off Market Date: Tue Aug 13 2024

Active Status

MLS Status: Sold

Location

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

Building

Building Area
Building Area: 2364 Square Feet

Community

Community Features: Public Transportation, Shopping, Park, Walk/Jog Trails, Medical Facility, Conservation Area, Highway Access, Public School, T-StationNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.28 acres

Offer

Contingencies: Pending P&S

Miscellaneous

BasementMls Number: 73268304

Additional Information

Public TransportationShoppingParkWalk/Jog TrailsMedical FacilityConservation AreaHighway AccessPublic SchoolT-Station
Last check for updates: about 2 hours ago
Listed by Andersen Group Realty, (781) 729-2329
Keller Williams Realty Boston Northwest, (781) 862-2800
Bought with: Andersen Group Realty, (781) 729-2329, Keller Williams Realty Boston Northwest, (781) 862-2800
Source: MLS PIN, MLS#73268304

Price History for 27 Ledyard Rd

DatePriceEventSource
09/04/2024$1,380,000Sold
MLS PIN #73268304
07/31/2024$1,200,000ContingentMLS PIN #73268304
07/23/2024$1,200,000Listed For SaleMLS PIN #73268304
01/13/2018$2,950ListingRemovedAgent Provided
12/11/2017$2,950Listed For RentAgent Provided

Market trends in Winchester

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
75
7MoM
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Property Tax and Assessment

Year2025
Tax$14,211
Assessment$1,281,400
Home facts updated by county records

Comparable Sales for 27 Ledyard Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
6 Marchant Rd, Winchester, MA
0.17
Single-Family Home
$1,325,000
04/22/26
3
2.5
2,153
446 Highland Ave, Winchester, MA
0.10
Single-Family Home
$940,000
12/23/25
2
1.5
2,033
4 Sargent Rd, Winchester, MA
0.07
Single-Family Home
$1,355,000
11/20/25
4
2.5
2,865
40 Sargent Rd, Winchester, MA
0.16
Single-Family Home
$1,290,000
12/05/25
3
1.5
1,492
6 Alden Ln, Winchester, MA
0.21
Single-Family Home
$1,275,000
06/25/26
3
2
1,511
89 Main St, Winchester, MA
0.19
Single-Family Home
$1,150,000
11/14/25
3
2.5
2,648
48 Winford Way, Winchester, MA
0.27
Single-Family Home
$1,115,000
07/15/25
3
2
1,978
17 Cranston Rd, Winchester, MA
0.05
Single-Family Home
$1,560,000
04/30/26
4
2.5
2,578
163 Main St, Winchester, MA
0.19
Single-Family Home
$1,175,000
08/18/25
4
2.5
2,335
17 Dennett Rd, Winchester, MA
0.30
Single-Family Home
$1,500,000
10/09/25
3
2.5
2,283

Nearby homes

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Assigned Schools

These are the assigned schools for 27 Ledyard 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 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

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Apartments for Rent

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Explore by feature - Pet Friendly

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Homes for sale near 27 Ledyard Rd

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Off Market Homes Near 27 Ledyard Rd

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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.