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

    20 Amberwood Dr, Winchester, MA 01890
  • /9

    $4,600 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
  • /18

    $8,500

    Total Monthly Price

    • 6 Beds
    • 2.5 Baths
    • 3,800 Sq Ft
    • House for Rent

    161 Highland Ave, Winchester, MA 01890

    Beautiful Colonial House in Prime Winchester Location steps from Middlesex Fells ReservationExperience comfort, space, and nature in this stunning 6-bedroom Colonial home in Winchester, MA, available August 1. Perfect for families or professionals seeking a peaceful retreat with convenient access to Boston.Nestled just steps from the Middlesex Fells Reservation (2,575 acres of hiking and

    161 Highland Ave, Winchester, MA 01890
  • /42

    $6,995 Per Month

    • 4 Beds
    • 2.5 Baths
    • 4,253 Sq Ft
    • House for Rent

    18 Grant Rd, Winchester, MA 01890

    Located in a favorite Winchester neighborhood, this spacious and thoughtfully designed home offers an ideal layout for today's lifestyle. The oversized family room flows seamlessly from the kitchen, creating a perfect space for entertaining and everyday living. The kitchen features modern appliances and a slider to the back deck for easy indoor-outdoor enjoyment. A first-floor bedroom or home

    Kim Covino Compass

    18 Grant Rd, 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
  • /40

    $15,000 Per Month

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

    186 Ridge St, Winchester, MA 01890

    Stunning 6,000 Sq Ft 5 bedroom 4.5 bath custom built colonial residence proudly situated on over an acre of land and offering gorgeous panoramic views. This beautifully maintained home located atop a hill on the West Side of Town, with three-car attached garage with side entrance into oversized mudroom. Main level features gourmet kitchen with high-end appliances, oversized island, dining area,

    Anzor Sidamonidze Skylight Real Estate, LLC

    186 Ridge St, Winchester, MA 01890
  • /32

    $5,750 Per Month

    • 5 Beds
    • 3.5 Baths
    • 3,404 Sq Ft
    • House for Rent

    17 Churchill Rd, Winchester, MA 01890

    Be the first to name this expansive property home nestled in a desirable Winchester neighborhood. This residence offers the perfect blend of comfort, convenience and modern updates. With 5 spacious bedrooms, 4 bathrooms, 2 car garage perfect for those harsh winters, ample off-street parking and large level and private yard. There have been numerous updates in recent years, mini split AC units

    Matthew Pierce True North Realty

    17 Churchill 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
  • /41

    $6,500 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,800 Sq Ft
    • House for Rent

    46 Loring Ave, Winchester, MA 01890

    Move right into this spacious newer construction home with a great layout, hardwood floors, high ceilings, spacious bedrooms, located near Macdonald Field with playground, tennis etc.. kitchen is fully applianced with gas stove & granite countertop opens into family room w access to rear yard and patio, formal living room and dining room. Direct entry 2 car garage- The oversized primary bedroom

    Kim Covino Compass

    46 Loring Ave, Winchester, MA 01890
  • /22

    $6,000 Per Month

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

    31 Fells Rd, Winchester, MA 01890

    Available 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 private

    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 $5,725 per month, though prices vary by neighborhood, size, and property type. As of July 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 $235,000 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 $5,875 per month in Winchester, MA, renters typically need to show $17,625 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 22.8, 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
12
Median Single Family Home Rent
$5,725
Median 3 Bedroom Single Family Home Rent
$4,300
Median 4 Bedroom Single Family Home Rent
$6,600
Median 5 Bedroom Single Family Home Rent
$7,575
How to Rent a Home