12

Winchester, MA Houses for Rent

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  • /36

    $15,000 Per Month

    • 6 Beds
    • 7 Baths
    • 8,866 Sq Ft
    • House for Rent

    20 Amberwood Dr, Winchester, MA 01890

    New construction 6 bedrooms and 7 full baths, 2 Car garage. Located in a highly desirable neighborhood just steps from VO Elementary School. The expansive 1st floor welcomes you with soaring ceilings and an elegant layout, including a sophisticated living room, family room, and private home office. The chef’s kitchen is a true centerpiece, boasting premium Thermador appliances, custom cabinetry,

    Agent Photo

    Wei Wang

    WW Real Estate LLC

    (781) 992-2320

    20 Amberwood Dr, Winchester, MA 01890
  • /27

    $10,000 Per Month

    • 6 Beds
    • 4.5 Baths
    • 6,583 Sq Ft
    • House for Rent

    282 High St, Winchester, MA 01890

    Fabulous 6 month rental opportunity with full additional in-law suite with private kitchen, bedroom, bath, and laundry. Very generous in size and scale.Light filled,modern all brick home abundant in space and comfort.Unrivaled privacy at end of cul-de-sac.Masterfully built staircase presents the two story great room with double sided fireplace.Spacious kitchen with island, double gas range, and

    Anthony Marino The Marino Group Collection

    282 High St, Winchester, MA 01890
  • /9

    $4,900 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
  • /22

    $6,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 3,500 Sq Ft
    • House for Rent

    40 Church St Unit B, Winchester, MA 01890

    One of a kind 3 bed, 2.5 bath, luxury townhouse in the heart of Winchester Center! Don’t miss out on this home with both luxury & convenience. Top of the line Viking appliances and French doors in the kitchen which draw in natural sunlightthat enhances the hardwood floors & granite countertops. The spacious master bedroom is sure to impress, with its highlighted wall-to-wall fireplace. Each

    Sarkis Kavlakian Real Estate by Hughes & Assoc. Inc.

    40 Church St Unit B, Winchester, MA 01890
  • /15

    $5,000 Per Month

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

    17 Russell Rd, Winchester, MA 01890

    Move in date: 6/15/2025. 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 minimumMove-in costs: First month's rent, one month's rent as a security deposit, Last month rentWelcome to 17 Russell Road, a well-maintained single-family home tucked

    KoKo Kwan Kwan Realty Inc.

    17 Russell Rd, Winchester, MA 01890
  • /28

    $15,000 Per Month

    • 5 Beds
    • 4.5 Baths
    • 5,820 Sq Ft
    • House for Rent

    186 Ridge St, Winchester, MA 01890

    Stunning 2020-built residence, fully furnished, beautifully maintained and located atop a hill on the West Side of Town, proudly situated on over an acre of land and offering gorgeous panoramic views. 5 bedroom 4.5 bath, 5,820SF custom built colonial with three-car attached garage with side entrance into oversized mudroom. Main level features gourmet kitchen with high-end appliances, oversized

    Anzor Sidamonidze Skylight Real Estate, LLC

    186 Ridge St, Winchester, MA 01890
  • /26

    $6,500 Per Month

    • 4 Beds
    • 4 Baths
    • 3,436 Sq Ft
    • House for Rent

    37 Emerson Rd, Winchester, MA 01890

    This sunlit, upgraded Winchester single-family home offers a perfect blend of comfort and elegance. The versatile 4-bedrooms & 4-Bathrooms layout features a convenient 1st-floor full bath alongside a formal living room, dining room, office, and spacious family room. The primary suite is located on the 2nd floor with a private ensuite. Skylights brighten the living areas, which open to a wide

    Hao Wang Dreamega International Realty LLC

    37 Emerson Rd, 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 Archambault Real Estate

    52 N Border Rd, Winchester, MA 01890
  • /32

    $12,000 Per Month

    • 4 Beds
    • 3.5 Baths
    • 4,300 Sq Ft
    • House for Rent

    59 Wedgemere Ave, Winchester, MA 01890

    Beautifully maintained home in one of Winchester’s most desirable family neighborhoods, the Flats..This spacious home full of charm offers generous living spaces, with 4-5 bedrooms, 3 full updated baths, eat in kitchen, freshly painted interior, gleaming hardwood floors, and abundant natural light throughout. The first floor features a large living room, formal dining room, kitchen, family room,

    Kim Covino Compass

    59 Wedgemere Ave, Winchester, MA 01890
  • /40

    $11,500 Per Month

    • 7 Beds
    • 3.5 Baths
    • 3,300 Sq Ft
    • House for Rent

    34 Glen Rd, Winchester, MA 01890

    TOP location! Beautifully renovated single family colonial in Ambrose elementary district, situated on a gorgeous lot with oversized new 2 car garage, This 6-7 bedroom 3.5 bath home has been tastefully updated & redesigned offering desirable open concept living w/ central air & all new systems. This home features a welcoming front porch, spacious foyer, beautiful custom chefs kitchen w/

    Kim Covino Compass

    34 Glen Rd, Winchester, MA 01890
  • /22

    $8,000 Per Month

    • 3 Beds
    • 2 Baths
    • 3,500 Sq Ft
    • House for Rent

    31 Fells Rd, Winchester, MA 01890

    Available for short term rental through October 2025 with flexible lease options. Prime location on desirable Fells Road with easy access to Middlesex Fells trails and conservation land. This charming home sits on a beautiful lot and offers a spacious first floor featuring a large family room, updated kitchen, and a den or optional first floor bedroom. Enjoy the screened porch overlooking the

    Kim Covino Compass

    31 Fells Rd, Winchester, MA 01890
  • /20

    $4,850 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 $4,925 per month, though prices vary by neighborhood, size, and property type. As of June 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 $208,000 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 $5,200 per month in Winchester, MA, renters typically need to show $15,600 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 25.0, 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 West Side, Downtown Woburn, Winchester Highlands, Arlington Heights and Arlington Center, each with its own character and price range.

Rental Home Trends in Winchester, MA

Rental Home Trends

Number of Houses for Rent
12
Median Single Family Home Rent
$4,925
Median 3 Bedroom Single Family Home Rent
$4,550
Median 4 Bedroom Single Family Home Rent
$6,500
Median 5 Bedroom Single Family Home Rent
$7,550
How to Rent a Home