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Newest Homes for Rent in Winchester, MA

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  • /44

    Starting at $2,680

    Total Monthly Price

    • 1 - 2 Beds

    225 Fallon Rd, Stoneham, MA 02180

    Here, smart design imbues modern comforts with alfresco joys. Quartz countertops, glass-enclosed showers, and quality stainless steel appliances add to your quality of life. Energy-efficient windows stream in sunlight while wood-style flooring inspires your next jaunt outside. But with thoughtful features like our enhanced fitness center and cyber studio, you won't have to wander far to activate

    The Mave

    (781) 430-4385

    225 Fallon Rd, Stoneham, MA 02180
  • /20

    Starting at $2,773 Plus Fees

    • Studio - 3 Beds

    416 Cambridge St, Winchester, MA 01890

    The Sanctuary at Winchester West is crafted to elevate every moment of your day—from morning workouts in the fully equipped fitness center to productive afternoons in private work-from-home pods and inviting gathering spaces. Whether you're entertaining in the chef-inspired kitchen and lounge, relaxing by the fire with neighbors, or enjoying the convenience of Whole Foods and local shops just

    Sanctuary Winchester West

    (339) 214-9536

    416 Cambridge St, Winchester, MA 01890
  • /24

    Starting at $3,205 Plus Fees

    • 1 - 3 Beds

    25-35 River St, Winchester, MA 01890

    The Sanctuary at Winchester North is designed for the way you live - casual fireside gatherings in the Den, a game of billiards in the Hive, a meal with friends prepared in the Nest's Chef's Kitchen. Maybe you prefer to make a splash in the pool, or stay on track with personal health goals in the fitness and health facility. With meticulously appointed common spaces designed for work, play, and

    Sanctuary Winchester North

    (781) 776-5329

    25-35 River St, Winchester, MA 01890
  • /10

    $2,150

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 635 Sq Ft
    • Condo for Rent

    200 Swanton St Unit T28, Winchester, MA 01890

    NO BROKER FEES. Bright 1-bedroom condo with UTILITIES INCLUDED available for rent in Winchester's desirable Parkview community. This recently refreshed unit offers a well-designed layout with a spacious living area, comfortable bedroom with a walk-in closet, and full bathroom.This home offers convenient ground-level access to beautifully landscaped outdoor space and a serene pond right

    200 Swanton St Unit T28, Winchester, MA 01890
  • /20

    $4,800 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,560 Sq Ft
    • Condo for Rent

    22 Grove Place Unit 6, Winchester, MA 01890

    Don't miss this opportunity to lease a beautifully appointed 3-bedroom, 2.5-bath townhome-style condo in the sought-after White Horse Commons community. Spanning 1,560sqft, this home features gleaming hardwood floors, a warm fireplace, and an abundance of natural light. The open kitchen offers generous counter and cabinet space, while in-unit washer/dryer, central A/C, and a full appliance suite

    The McLaren D'Agostino Team Compass

    22 Grove Place Unit 6, Winchester, MA 01890
  • /29

    $5,500 Per Month

    • 4 Beds
    • 3.5 Baths
    • 1,928 Sq Ft
    • Apartment for Rent

    48 Spruce St Unit 1, Winchester, MA 01890

    Spacious 4-bedroom, 3.5-bath townhouse ideally located within walking distance to the town center, schools, and commuter rail. This well-maintained home features beautiful hardwood flooring throughout, a bright and functional layout, and generous living space perfect for everyday living and entertaining. Enjoy outdoor living with a private fenced-in patio. Landscaped yard space. Additional

    Dylan Archambault Archambault Real Estate

    48 Spruce St Unit 1, Winchester, MA 01890
  • /18

    $3,600 Per Month

    • 3 Beds
    • 2 Baths
    • 2,400 Sq Ft
    • Apartment for Rent

    16 Richardson St Unit 18, Winchester, MA 01890

    3 bedroom 2 bathroom colonial style duplex house in the center of Winchester for rent. Colonial style with spacious living room and kitchen room on the first floor. Second floor master bedroom has an office/exercise room attached. Full basement provides tons of storage spaces. Walking distance to schools, shops, bus stop and commuter rail station. Big backyard provides a great private space for

    Weidong Li WINN Real Estate & Consulting

    16 Richardson St Unit 18, Winchester, MA 01890
  • /17

    $3,200 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,460 Sq Ft
    • Condo for Rent

    60 Lake St Unit D, Winchester, MA 01890

    LOCATION! LOCATION! LOCATION! Here is your opportunity to live in a quiet and beautifully renovated townhouse in the heart of Winchester, MA. Walking distance to all local schools, parks, downtown shops and restaurants, the commuter rail, tennis courts, and right next to Wedge Pond; where you can enjoy year round fun whether it’s swimming in the summer, or ice skating in the winter. The first

    Clara Wu United Real Estate, LLC

    60 Lake St Unit D, 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
  • /36

    $3,400 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,332 Sq Ft
    • Condo for Rent

    7 Conant Rd Unit 11, Winchester, MA 01890

    Available 8/1/2026! Highly Desirable The Willows Condominiums.... Sunny 2 bedrooms and 2.5 bathrooms second floor unit... Open layout living room, dining room, kitchen & sliding door leads to private deck.... In-unit laundry, Stainless Steel Appliances, Gas fireplace, Hardwood floors... Gas heating with Central AC... Spacious master bedroom with large walk-in closet and bathroom in suite...

    Young Wang Phoenix Real Estate Partners, LLC

    7 Conant Rd Unit 11, Winchester, MA 01890
  • /14

    $7,900

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • Condo for Rent

    18 Grant Rd, Winchester, MA 01890

    An exceptional 4-bedroom, 2.5 bath home offers both comfort and versatility. The expansive family room, located just off the kitchen, creates a welcoming setting for entertaining or relaxing. Kitchen is equipped with modern appliances and sliding glass doors that open to rear deck. First floor laundry room and bedroom (or office) enhance practicality. The impressive primary suite includes 2

    18 Grant Rd, Winchester, MA 01890
  • /8

    $2,400

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 900 Sq Ft
    • Condo for Rent

    3 Glengarry Rd Unit 3, Winchester, MA 01890

    This 900 sq. ft. property at 3 Glengarry Rd features 1 bedroom, 1 bathroom, and a home office area. This property can be rented furnished or unfurnished. The living room offers ample space for relaxation. The kitchen includes a dishwasher for convenience and is adjacent to the dining area. The bedroom provides a comfortable living space with sufficient closet storage. Additional amenities include

    3 Glengarry Rd Unit 3, Winchester, MA 01890
  • /10

    $2,725

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • Condo for Rent

    35 Vine St Unit 303, Winchester, MA 01890

    Immaculate 2 bedroom, 2 full bath apartment on upper floor of brick building with heat and hot water included. Excellent location just steps to Winchester Center and Commuter Rail. Central A/C, dishwasher & disposal. 2 car, assigned parking spots included! 1 spot in garage under and 1 spot in lot. Elevator in building. Laundry in building. Available now or June-September 1st. No pets/no smoking.

    35 Vine St Unit 303, Winchester, MA 01890
  • /18

    $2,250 Per Month

    • 1 Bed
    • 1 Bath
    • 606 Sq Ft
    • Condo for Rent

    200 Swanton St Unit 222, Winchester, MA 01890

    Available now 6/1, currently being painted and cleaned for first of the month occupancy. You’ll love this updated one-bedroom unit in the sought-after Parkview Complex, with its access to outdoor space, including private deck, and seasonal pool and barbeque area for residents and guests. Updated kitchen with stainless appliances, including dishwasher. Other building amenities include laundry

    Pirani & Wile Group Gibson Sotheby's International Realty

    200 Swanton St Unit 222, Winchester, MA 01890
  • /42

    $5,500 Per Month

    • 3 Beds
    • 3.5 Baths
    • 3,090 Sq Ft
    • Apartment for Rent

    17 Cardinal St Unit 17, Winchester, MA 01890

    Situated on a peaceful cul-de-sac, this beautiful, townhouse offers privacy and modern amenities. It features hardwood floors, high-end finishes, and two-zone control. The main level includes a bright living room with a gas fireplace, a spacious dining area, and a gourmet kitchen with marble countertops and stainless steel appliances. Additional highlights include a sunlit office with French

    CardinalRE Group Hooli Homes Boston

    17 Cardinal St Unit 17, Winchester, MA 01890
  • /25

    $4,400 Per Month

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Apartment for Rent

    67 Church St, Winchester, MA 01890

    Enjoy this beautiful recently renovated home right outside Winchester center! Direct entry unit completely updated all new high end gorgeous kitchen & bath, hardwood floors, new heating system with central air, new windows, electric, very high ceilings, washer & dryer in unit, 2 car parking driveway in rear, exclusive patio area great for grilling! Beautifully finished lower level offers a large

    Kim Covino Compass

    67 Church 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
  • /8

    $4,100 Per Month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Apartment for Rent

    63 Holland St Unit 63, Winchester, MA 01890

    Welcome to 63 Holland St in Winchester! A beautifully renovated 2-bedroom, 1-bath apartment offering a perfect mix of charm and modern updates. This bright and inviting first-floor unit features hardwood floors throughout, recessed lighting, freshly painted interiors, and a stunning new kitchen with quartz countertops and stainless steel appliances. The updated bathroom includes a walk-in tiled

    Issam Dib Skyline Realty

    63 Holland St Unit 63, 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
  • /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
  • /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

    $3,150 Per Month

    • 2 Beds
    • 1 Bath
    • 1,172 Sq Ft
    • Condo for Rent

    31 Irving St Unit 1, Winchester, MA 01890

    Bright and sunny 1st floor unit is ready to move in. Large sun drenched living with newer hardwood and large windows; modern kitchen equipped with stainless appliances and plenty of cabinets connects with the dinning room to create an open floor plan. Both good sized bedrooms are with hard floors and double door closets. Full bath on the same living level is complete with tile floors and tub.

    Amy Guo Phoenix Real Estate

    31 Irving St Unit 1, 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
  • /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
  • /17

    $2,195

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft
    • Condo for Rent

    19 Irving St Unit 3, Winchester, MA 01890

    Top Floor (3rd floor) 2 Bedroom 1 Bathroom located minutes from Winchester Center & Commuter Rail. Fully carpeted Livingroom, bedrooms hallway ,with kitchen and bathroom ceramic tile. Private deck overlooking yard. gas cooking, gas heat. Great kitchen with dishwasher, washer dryer in unit.Tenant pays gas & electric (and trash at Winchester Transfer Station. Transfer station ticket for

    19 Irving St Unit 3, 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
  • /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
  • /14

    $2,600 Per Month

    • 2 Beds
    • 1 Bath
    • 822 Sq Ft
    • Condo for Rent

    200 Swanton St Unit 237, Winchester, MA 01890

    Sunny & Bright 2-Bedroom Condo in Winchester Park View – Available 05/15. Enjoy comfortable living in this updated and sunny 2-bedroom, 1-bathroom condo. Private balcony. Heat, electricity, hot water, and more included in rent. 2 parking spaces. Ground maintenance and trash removal included. Conveniently located near shopping, restaurants, and Winchester Town Center. Just a short walk to the

    Agent Photo

    Wei Wang

    WW Real Estate LLC

    (781) 734-6553

    200 Swanton St Unit 237, Winchester, MA 01890
  • /15

    $2,675 Per Month

    • 2 Beds
    • 1 Bath
    • 850 Sq Ft
    • Condo for Rent

    200 Swanton St Unit T37, Winchester, MA 01890

    ALL UTILITIES INCLUDED!!!! Ground Level with Private Entrance. NO STAIRS! Lovely terrace level unit at Parkview available 5/1 This immaculate and well cared for home includes dishwasher, on site laundry, parking,Situated in a very convenient location, near everything! Enjoy the beautifully landscaped common area with pool, cabana and picnic table. Super Value with ALL UTILITIES INCLUDED make this

    Mary Doyle Berkshire Hathaway HomeServices Commonwealth Real Estate

    200 Swanton St Unit T37, Winchester, MA 01890
  • /37

    $2,495

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    19 Irving St Unit 3-J, Winchester, MA 01890

    Top Floor (3rd floor) Lovely 2 Bedroom 1 Bathroom located minutes from Winchester Center & Commuter Rail. Fully carpeted Livingroom, bedrooms hallway ,with kitchen and bathroom ceramic tile. Private deck overlooking yard. gas cooking, gas heat; All new dishwasher. In unit laundry! Plush carpet freshly cleaned!Tenant pays gas & electric (and trash at Winchester Transfer Station). Transfer

    19 Irving St Unit 3-J, 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
  • /30

    $2,800 Per Month

    • 2 Beds
    • 1 Bath
    • 810 Sq Ft
    • Apartment for Rent

    200 Swanton St Unit T35, Winchester, MA 01890

    SPRING TIME IS COMING! Welcome to this Stunning 2 BR unit on Terrace level with amazing view of duck pond and flowering garden area from private outdoor patio at Parkview Condominiums. Spacious open LR/DR with updated kitchen and bath. Kitchen to include stainless steel appliances, glass tile backsplash, very nice countertops and huge peninsula great for parties. 2 huge bedrooms with lots of

    Nuri Tirana Tirana Real Estate Group

    200 Swanton St Unit T35, 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
  • /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
  • /30

    $4,150 Per Month

    • 4 Beds
    • 2 Baths
    • 1,967 Sq Ft
    • Apartment for Rent

    10-12 Webster St Unit 1, Winchester, MA 01890

    Amazing 4 bed 2 bath available 2/1/26 located within close proximity of Winchester Center! This spacious apartment takes up the first floor and lower level of a 2 family, but it has a single-family feel to it! Inside on the first floor, you'll find hardwood floors throughout, a living room, a dining room, two spacious bedrooms, and a great eat-in kitchen featuring a new dishwasher and

    Ryan Kelly Real Broker MA, LLC

    10-12 Webster St Unit 1, Winchester, MA 01890
  • /32

    $4,000

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 1,967 Sq Ft
    • Condo for Rent

    10 Webster St Unit 1, Winchester, MA 01890

    Amazing 4 bed 2 bath located within close proximity of Winchester Center! This spacious apartment takes up the first floor and lower level of a 2 family, but it has a single-family feel to it! Inside on the first floor, you'll find hardwood floors throughout, a living room, a dining room, two spacious bedrooms, and a great eat-in kitchen featuring a new dishwasher and refrigerator. Downstairs

    10 Webster St Unit 1, Winchester, MA 01890
  • /4

    $2,000

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    200 Swanton St Unit 310, Winchester, MA 01890

    NO BROKER FEE TO TENANT OWNER PAYS!Move-In Costs Fees:Last Month Rent: $2,000First Month Rent: $2,000Security Deposit: $1,000Disclaimer: Contact EDGE for more information on this listing, and hundreds of our other listings! See why more people are choosing the highest and most-reviewed real estate firm in Massachusetts. Brokerage fee applies. EDGE Realty Advisors is

    (781) 604-1321

    200 Swanton St Unit 310, Winchester, MA 01890
  • /7

    $2,050 Plus Fees

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    2 Elmwood Ave Unit 1, Winchester, MA 01890

    This nice 1 Bedroom 1 Bath place in the Winchester area is available for 08-02-2026. Included Features are: Laundry in Basement.Boston Pads is not responsible for any errors, omissions and change in price, prior sale, rent and withdrawal without notice. All information from sources reliable but not guaranteed. Photographs, videos, description and information about the properties reflect

    (781) 604-1904

    2 Elmwood Ave Unit 1, Winchester, MA 01890
  • /21

    $2,100

    Total Monthly Price

    • 1 Bed
    • 1.5 Baths
    • 660 Sq Ft
    • Condo for Rent

    269 Cambridge Rd Unit undisclosed, Woburn, MA 01801

    Affordable, highly coveted one-bedroom condo available in the much sought after Crescent Park Condominiums! A+ location in Woburn opposite Horn Pond Shopping Center near a Whole Foods, restaurants and lots of shopping. Dedicated parking spot and storage unit. Access to pool, clubhouse with fireplace, kitchen, pool table, piano and workout room. New washer and dryer. Extra storage in basement.

    269 Cambridge Rd Unit undisclosed, Woburn, MA 01801

Frequently Asked Questions

How much does it cost to rent a home in Winchester, MA?
The median rent for a home in Winchester, MA is $5,200 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 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 home include The Flats, West Side, Downtown Woburn, Winchester Highlands and Shakerhill, each with its own character and price range.

Rental Trends in Winchester, MA

Rental Home Trends

Number of Homes for Rent
39
Median Rent
$5,200
Median Single Family Home Rent
$4,925
Median Townhouse Rent
$6,400
Median Condo Rent
$2,625
How to Rent a Home