23 Jefferson Rd

3,100 Sq. Ft.
$37 / Sq. Ft.
3,100
Sq. Ft.
$37
per Sq. Ft.

Description

Stunning home situated in one of Winchester's most sought-after neighborhoods available for rare 1 or 2 year rental. Enter the elegant foyer to find large living room, sun-drenched playroom and dining room next to generous kitchen which overlooks the large, private back yard. Laundry in side entry mud room offers convenience and a front-facing home office overlooks the picturesque neighborhood. Upstairs you'll find a generous primary suite plus 3 additional bedrooms and family bath. Third floor features...Stunning home situated in one of Winchester's most sought-after neighborhoods available for rare 1 or 2 year rental. Enter the elegant foyer to find large living room, sun-drenched playroom and dining room next to generous kitchen which overlooks the large, private back yard. Laundry in side entry mud room offers convenience and a front-facing home office overlooks the picturesque neighborhood. Upstairs you'll find a generous primary suite plus 3 additional bedrooms and family bath. Third floor features 2 large bedrooms and an additional full bath. Two car detached garage and rear patio ideal for entertaining in the warmer months. Exceptional storage and updated systems, this home is ideal for the discerning guest.

Listing Agent

Property Details for 23 Jefferson Road

Town
Winchester
MLS Area
Winchester Highlands
Area
MA-Winchester-Winchester Highlands, MA-Winchester
Garage Spaces
2
Open Parking Spaces
8.00
Parking Spaces Total
8
LISTING UPDATED: 03/05/2026 10:41 AM

Property Details for 23 Jefferson Road

StatusActive
MLS #73481047
Days on Market20
Rental Incentives-
Costs & Fees-
Available Date03/20/2026
Furnished-
Compass TypeRental
MLS TypeRental / Single Family
Year Built1929
CountyMiddlesex County
Add your commute

Building Information for 23 Jefferson Road

Building/Complex23 Jefferson RdFloor-Stories-Pet Policy-Pet Policy DetailsYes w/ RestrictionsYear Built1929Building Size-Lot Size0.37 AC / 16,000 SF

Property Information for 23 Jefferson Road

General Details
Property Details
  • Building Area Units: Square Feet
  • Community Features: Public Transportation, Walk/Jog Trails, Conservation Area, Highway Access, Public School
  • Living Area: 3100.0
  • SqFt with Basement: No
  • Single Family Type: Single Family Residence
  • Waterfront: No
  • Water View: No
  • Year Built Details: Approximate,Renovated Since
  • Year Built Source: Public Records
Location/School
  • Grade School: Lincoln
  • High School: Whs
  • Middle School: Mccall
Features
Interior Features
  • Appliances: Range, Dishwasher, Disposal, Refrigerator, Freezer, Washer, Dryer
  • Num of Baths: 5.0
  • Num of Full Baths: 4
  • Num of Half Baths: 1
  • Bathrooms Total Decimal: 4.50
  • Bathrooms Total Integer: 5
  • FireplaceYN: Yes
  • Fireplaces: 1
  • Interior Features: Office, Play Room
  • Laundry Features: First Floor, In Unit
  • Primary Bath: Yes
  • SpaYN: No
Exterior Features
  • Exterior Features: Patio, Professional Landscaping
  • Exterior Features: Professional Landscaping, Patio
  • Patio And Porch Features: Patio
Parking Features
  • Covered Spaces: 2.00
  • Garage: Yes
Utilities
  • Cooling: Yes
  • Heating: Natural Gas, Forced Air
  • Heating: Yes
Room Information
Primary Bedroom
  • Primary Bedroom Level: Second Floor
Bedroom 2
  • Bedroom2 Level: Second
Bedroom 3
  • Bedroom3 Level: Second
Bedroom 4
  • Bedroom4 Level: Second
Bedroom 5
  • Bedroom5 Level: Third
Bathroom 1
  • Bathroom1 Level: Third
Other Room 1
  • Room Office Level: First
Property Information
Property Info
  • Year Round: Yes
  • Farm Land Area Units: Square Feet
  • WARRANTY: No
  • Lot Size Units: Acres
  • Disclosures: Beautifully furnished,start date and pets negotiable.
Tax Information
  • Tax ID: 895505
Building / Association Information
Living Characteristics
  • Beds Total: 6
Other Building Characteristics
  • Accessibility Features: No
Income / Expenses
  • Insurance Required: Yes
Complex & Association Information
  • Adult Community: No
Unit Information
Unit Information
  • Unit Floor Level Integer: 1.0
Rental Info
Rental Info
  • Availability Date: 03-20-2026
  • Available Now: No

Property History for 23 Jefferson Road

DateEvent & SourcePriceAppreciation
Feb 28, 2026

Listed (Active)

MLS PIN #73481047

$9,500—
Jul 14, 2025

Expired

MLS PIN #73359523

$9,500—
Jul 14, 2025

Temporarily Withdrawn

MLS PIN #73359523

$9,500—
Apr 14, 2025

Listed (Active)

MLS PIN #73359523

$9,500—
DateEvent & SourcePrice
02/28/2026

Listed (Active)

MLS PIN #73481047

$9,500
07/14/2025

Expired

MLS PIN #73359523

$9,500
07/14/2025

Temporarily Withdrawn

MLS PIN #73359523

$9,500
04/14/2025

Listed (Active)

MLS PIN #73359523

$9,500

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Schools near 23 Jefferson Road

This home is within Winchester School District.
Rating
School
Type
Grades
Distance
Public - K to 5
Public - 6 to 8
Public - 9 to 12
Rating
School
Distance
Lincoln Elementary School
PublicK to 5

McCall Middle School
Public6 to 8

Winchester High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

23 Jefferson Road is available for rent in Winchester, MA 01890. This property was listed on February 28, 2026 by Compass, it's currently listed at $9,500. This listing's school district is Winchester School District. Nearby schools include Lincoln Elementary School, McCall Middle School and Winchester High School. 23 Jefferson Road is a 6-bed, 5-bath, 3,100 sqft a property built in 1929.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the owner. No financial or legal advice provided. Equal Housing Opportunity.

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, 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., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.