11

Winchester, MA Houses for Rent

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  • /25

    $1,500

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 300 Sq Ft
    • House for Rent

    353 Washington St, Arlington, MA 02474

    Hi there! We have two bedrooms in a stand-alone house on Washington St. in Arlington. I live here with my daughter. The kitchen and baths are well updated, and the house is surprisingly well-insulated against the heat and cold. Common areas are open for all to enjoy and fill and decorate as you like. Unless you have terrible taste. :)The basement room is half the footprint of the house,

    353 Washington St, Arlington, MA 02474
  • /14

    $4,625

    Total Monthly Price

    • 4 Beds
    • 2.5 Baths
    • 2,150 Sq Ft
    • House for Rent

    5 Stoneham St, Woburn, MA 01801

    4 Bedrooms | 2.5 Baths | Renovated Single Family Near Winchester & Commuter RailFreshly renovated single-family home located in a quiet, scenic neighborhood on the Winchester line. This spacious home offers 4 bedrooms, 2.5 bathrooms, central A/C, and an attached 1-car garage with EV charger hookup, plus ample off-street parking.The main level features a brand-new kitchen with

    5 Stoneham St, Woburn, MA 01801
  • /21

    $5,500 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,632 Sq Ft
    • House for Rent

    111 Highland Ave, Winchester, MA 01890

    Welcome to this spacious and charming Colonial offering beautiful architectural character, a flexible floor plan, and generous living space across multiple levels.Step into the welcoming foyer and discover a bright, inviting home featuring a fireplaced living room with beamed ceilings and oversized windows, complemented by a sun-filled adjoining sunroom.The beautiful kitchen features granite

    Michelle Li Zhensight Realty LLC

    111 Highland Ave, Winchester, MA 01890
  • /9

    $4,400 Per Month

    • 3 Beds
    • 1.5 Baths
    • 2,754 Sq Ft
    • House for Rent

    16 Nathaniel Rd, Winchester, MA 01890

    Available now, Spacious 3 bedroom, 1.5 bathroom single family home for rent in the heart of Winchester. This house offers a large first floor, an updated kitchen with ample cabinet space, and a private fenced backyard perfect for entertaining. The property also features a two car garage, providing additional storage and convenience. Enjoy the convenience of being just steps away from a top-rated

    Yu Li Blue Ocean Realty, LLC

    16 Nathaniel Rd, Winchester, MA 01890
  • /21

    $4,200 Per Month

    • 3 Beds
    • 2 Baths
    • 1,678 Sq Ft
    • House for Rent

    22 Baldwin St, Winchester, MA 01890

    Beautifully renovated single-family home on a quiet cul-de-sac in desirable Winchester. Situated on a spacious 9,500± sq. ft. lot, this move-in-ready home features newly finished hardwood floors throughout, an open-concept living and dining area, an updated kitchen with gas cooking, a cozy family room with a wood-burning fireplace, and a full bath on the main level. Upstairs offers three spacious

    Qian Han JW Real Estate Services, LLC

    22 Baldwin St, Winchester, MA 01890
  • /15

    $4,800 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,657 Sq Ft
    • House for Rent

    17 Russell Rd, Winchester, MA 01890

    Move in date: Now. Tenant pays all utilities (gas, heat, electricity, cold/hot water and trash disposal). Lead Paint: Certified Treated. 2 off street parking. Central AC ,Pets negotiable. Laundry in the unit. 12-month lease minimum Move-in costs: First month's rent, one month's rent as a security deposit, Last month rent Welcome to 17 Russell Road, a well-maintained single-family home tucked away

    KoKo Kwan Kwan Realty Inc.

    17 Russell Rd, Winchester, MA 01890
  • /28

    $7,500 Per Month

    • 6 Beds
    • 3 Baths
    • 3,000 Sq Ft
    • House for Rent

    161 Highland Ave Unit n/a, Winchester, MA 01890

    Enjoy the best of Winchester living in this beautifully maintained six-bedroom, two-and-a-half-bath Colonial, ideally situated just moments from the Middlesex Fells Reservation. Available August 1, this spacious home offers a versatile layout designed for comfortable everyday living, with generous room sizes, abundant natural light, and central HVAC for year-round comfort. Outside, the

    Lisa Godwin Gibson Sotheby's International Realty

    161 Highland Ave Unit n/a, Winchester, MA 01890
  • /39

    $13,000 Per Month

    • 6 Beds
    • 5.5 Baths
    • 6,400 Sq Ft
    • House for Rent

    52 N Border Rd, Winchester, MA 01890

    Grand and masterfully crafted, this exceptional residence sits on a private road abutting the Fells conservation land, offering rare privacy and natural surroundings. The spacious home features 6 bedrooms and 6 bathrooms, beginning with a stunning foyer that opens to a sprawling first floor. Sun-filled rooms showcase exquisite custom craftsmanship throughout. The gourmet kitchen is equipped with

    Dylan Archambault The Archambault Group

    52 N Border Rd, Winchester, MA 01890
  • /38

    $6,500 Per Month

    • 3 Beds
    • 3 Baths
    • 2,443 Sq Ft
    • House for Rent

    25 Berkshire Dr, Winchester, MA 01890

    This beautifully renovated home offers over 2,400 sq ft of thoughtfully designed living space across two levels. The home blends modern finishes with functional comfort, making it ideal for today's lifestyle. Step inside to find a spacious open layout enhanced by high-quality updates throughout. The kitchen, baths, and mudroom feature custom cabinetry with high end Spanish panels, dovetail

    Nadia Mounsif McCaul & Mounsif Real Estate Group LLC

    25 Berkshire Dr, Winchester, MA 01890
  • /34

    $6,000 Per Month

    • 4 Beds
    • 4 Baths
    • 2,700 Sq Ft
    • House for Rent

    270 Cross St Unit SF, Winchester, MA 01890

    Beautifully renovated 4BR/4BA home in Winchester’s desirable Lynch School District offering three levels of modern living. The main floor features a dedicated office, hardwood floors, mini-split cooling, a wood-burning fireplace, 2-zone Nest heating, and a spacious kitchen with quartz countertops and stainless steel appliances. The walkout lower level is perfect for an in-law or au-pair suite

    The Abundant Group Real Broker MA, LLC

    270 Cross St Unit SF, Winchester, MA 01890
  • /20

    $4,250 Per Month

    • 4 Beds
    • 1.5 Baths
    • 1,700 Sq Ft
    • House for Rent

    488 Washington St, Winchester, MA 01890

    Charming, updated Colonial filled with character. This beautiful home features an updated kitchen that is bright and open and offers granite counter tops, stainless steel appliances, frameless maple cabinets & recessed lights. Updated bathrooms. Hardwood floors throughout the 1st & 2nd floors. Access the stone and granite patio through French doors in the dining room. The patio is fenced in and

    Matthew Pierce True North Realty

    488 Washington St, Winchester, MA 01890

Frequently Asked Questions

How much does it cost to rent a single-family home in Winchester, MA?
The median rent for a single-family home in Winchester, MA is $5,600 per month, though prices vary by neighborhood, size, and property type. As of August 2026, condos tend to be the most affordable option while single-family homes and townhouses are currently more expensive.
How much do you need to make to afford rent in Winchester, MA?
To comfortably afford the median rent in Winchester, MA, a household needs to earn roughly $176,000 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $4,400 per month in Winchester, MA, renters typically need to show $13,200 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Winchester, MA?
In Winchester, MA, the price-to-rent ratio is 32.2, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.
What neighborhoods in Winchester, MA are best for renting a single-family home?
The best neighborhood for renting in Winchester, MA depends on your priorities: commute, walkability, budget, and lifestyle all play a role. Popular areas for renting a single-family home include Winchester Highlands, Arlington Center, West Medford, Arlington Heights and Countryside, each with its own character and price range.

Rental Home Trends

Number of Houses for Rent
11
Median Single Family Home Rent
$5,600
Median 3 Bedroom Single Family Home Rent
$4,200
Median 4 Bedroom Single Family Home Rent
$6,550
Median 5 Bedroom Single Family Home Rent
$7,550
How to Rent a Home