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

$2,660,400

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

27 Ledyard Rd, Winchester, MA 01890

Est. Refi. Payment $16,246/mo*
Refinance Your Home
Currently Off Market - Sold Sep 4, 2024 for $1,380,000

Home Value

Trulia Estimate
$2.66M
Since last month
Increased$57K (+2.2%)
Since last year
Decreased$64K (-2.3%)
Since last sale
Increased$1M (+92.8%)
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 +227% in the last 10 years
MonthEstimated value
2026
August 2026$2.66M
August 2026$2.65M
July 2026$2.6M
June 2026$2.73M
May 2026$2.57M
April 2026$2.57M
March 2026$2.44M
February 2026$2.36M
January 2026$2.42M
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
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
17 Cranston Rd, Winchester, MA
0.05
Single-Family Home
$1,560,000
04/30/26
4
2.5
2,578
17 Dennett Rd, Winchester, MA
0.30
Single-Family Home
$1,500,000
10/09/25
3
2.5
2,283
4 Oakland Cir, Winchester, MA
0.51
Single-Family Home
$1,651,000
10/17/25
3
2
2,368
71 Sargent Rd, Winchester, MA
0.35
Single-Family Home
$1,399,000
06/30/26
3
3.5
2,936

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
29 Allen Rd, Winchester, MA 01890
0.04
$1,834,300
4
2.5
2,810
Off Market
4 Sargent Rd, Winchester, MA 01890
0.07
$1,355,000
4
2.5
2,865
Recently Sold
428 Highland Ave, Winchester, MA 01890
0.08
$1,280,000
3
1.5
2,072
Off Market
17 Cranston Rd, Winchester, MA 01890
0.05
$1,560,000
4
2.5
2,578
Recently Sold
10 Allen Rd, Winchester, MA 01890
0.09
$1,197,500
3
1.5
1,520
Off Market
437 Highland Ave, Winchester, MA 01890
0.11
$1,185,400
3
2
1,589
Off Market
446 Highland Ave, Winchester, MA 01890
0.10
$940,000
2
1.5
2,033
Recently Sold
50 Allen Rd, Winchester, MA 01890
0.09
$1,712,800
3
2
2,769
Off Market
20 Stowell Rd, Winchester, MA 01890
0.13
$1,781,400
3
2
2,314
Off Market
445 Highland Ave, Winchester, MA 01890
0.13
$2,148,000
4
3.5
3,588
Off Market
16 Marshall Rd, Winchester, MA 01890
0.15
$1,925,400
4
3
2,866
Off Market

Local Information

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

Home Highlights

Single-Family Home
Built in 1940
0.28 acre lot
2,364 sqft
$1,125/sqft
1 Car Garage

About this House

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. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,660,400, with a rent estimate of $4,776/month.
Last check for updates: about 7 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

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

Price and Tax history

DateEventPrice
Sep 4, 2024
Source: MLS PIN #73268304
Sold
$1,380,000
Jul 31, 2024
Source: MLS PIN #73268304
Contingent
$1,200,000
Jul 23, 2024
Source: MLS PIN #73268304
Listed For Sale
$1,200,000
Jan 13, 2018
Source: Agent Provided
ListingRemoved
$2,950
Dec 11, 2017
Source: Agent Provided
Listed For Rent
$2,950

Market trends in Winchester

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
62
2MoM

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 27 Ledyard Rd

  • What is 27 Ledyard Rd estimated to be worth?
    Trulia's estimated value for 27 Ledyard Rd in Winchester, MA is $2,660,400.
  • What is the price history for 27 Ledyard Rd?
    27 Ledyard Rd in Winchester, MA last sold for $1,380,000 in September 2024.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Winchester?
    Residents describe Winchester, MA as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See recently sold homes in Winchester, MA.
  • Does 27 Ledyard Rd have air conditioning?
    Yes, 27 Ledyard Rd in Winchester, MA has air conditioning.
  • Does 27 Ledyard Rd have laundry facilities?
    Yes, 27 Ledyard Rd in Winchester, MA has in-unit laundry.

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Off Market Homes Near 27 Ledyard Rd

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