59

Winchester, MA Homes for Rent

Section Image Section Image
  • /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
  • /20

    Starting at $2,828 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

    416 Cambridge St, Winchester, MA 01890
  • /9

    $2,675 Per Month

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

    200 Swanton St Unit T37, Winchester, MA 01890

    Available now! Bright and spacious terrace-level 2-bedroom apartment offering exceptional value with heat, hot water, electricity, and air conditioning all included in the rent. This well-maintained home features an updated kitchen with dishwasher, generous living space, ample closet storage, and comfortable bedrooms. Enjoy the convenience of one assigned parking space included, with the option

    Agent Photo

    Joan Powell

    REMAX Andrew Realty Services

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

    225 Fallon Rd, Stoneham, MA 02180
  • /24

    Starting at $3,187 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

    25-35 River St, Winchester, MA 01890
  • /13

    $4,550 Plus Fees

    • 3 Beds
    • 2.5 Baths
    • 1,826 Sq Ft
    • Townhouse for Rent

    171 Swanton St, Winchester, MA 01890

    Property Id: 2604314Welcome home to this rare opportunity to reside in the highly sought after " Village" community in Winchester. This sunny & spacious Townhome boasts of fresh paint, newer floors, updated kitchen with stainless steel appliances, oversized rooms with an abundance of windows perfect for natural light, 2.5 baths one in with primary suite with a walk in closet, washer/dryer

    171 Swanton St, 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

    2 Elmwood Ave 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
  • /15

    $2,000

    Total Monthly Price

    • Studio
    • 1 Bath
    • 300 Sq Ft
    • Condo for Rent

    219 Washington St Unit 2, Winchester, MA 01890

    Amazing location right in the heart of Winchester! Close walking distance to downtown. - Utilities INCLUDED! - Off-street parking available- Laundry on-site- Close to public transportation

    219 Washington St Unit 2, 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
  • /15

    $3,100 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
  • /19

    $3,800 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,500 Sq Ft
    • House for Rent

    33 Nelson St, Winchester, MA 01890

    Wonderful single family home for rent! Located in nice quiet neighborhood close by acclaimed Winchester High School. House is certified lead paint compliant! Walking distance to train, shops and restaurants in beautiful downtown Winchester. Recently updated kitchen and baths. Granite counters and stainless steel appliances. New windows, gas heating and new central air conditioning make for energy

    Russell Hulteen Coldwell Banker Realty - Lexington

    33 Nelson St, Winchester, MA 01890
  • /42

    $4,500 Per Month

    • 4 Beds
    • 2 Baths
    • 2,085 Sq Ft
    • House for Rent

    41 Cross St, Winchester, MA 01890

    Available August 1st — a freshly painted side-entrance Colonial offering space, flexibility, and a prime Winchester location. The expansive eat-in kitchen flows into the dining area and family room, ideal for everyday living. The main level offers a bedroom or home office, full bath, and mudroom with laundry — perfect for one-level living. Upstairs are three generous bedrooms and a full bath,

    Andersen Group Realty Keller Williams Realty Boston Northwest

    41 Cross 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
  • /25

    $4,200 Per Month

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

    67 Church St, Winchester, MA 01890

    DOWNTOWN WINCHESTER! Enjoy this beautiful recently renovated home right outside Winchester center! Direct entry 2 bedroom 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

    Kim Covino Compass

    67 Church 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
  • /38

    $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
  • /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
  • /9

    $2,495 Per Month

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

    200 Swanton St Unit 507, Winchester, MA 01890

    Owner hosts open house this Sunday 6/28 at 5PM. Don’t miss this spacious 2-bedroom condo near the heart of Winchester, in one of the top public school districts in MA. Prime location: walk to shops, schools, restaurants, parks, and the T. Enjoy easy access to I-93, I-95, and the commuter rail—just 8 miles north of Downtown Boston.The unit features an open-concept living, dining, and kitchen area

    Sophia Xu Blue Ocean Realty, LLC

    200 Swanton St Unit 507, Winchester, MA 01890
  • /14

    $2,250 Per Month

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

    200 Swanton St Unit 416, Winchester, MA 01890

    The sought after Parkview Condominium! Prime Winchester Location ! Living room with glass sliders to balcony overlooking a calming and picturesque landscaped wildlife garden and pond with ducks & swans. Rent includes ALL utilities - heat, cold & hot water, electricity and 1 gated parking space! Amenities: swimming pool and on-site laundry facilities! No pets. No smoking of any substances.

    Ai Cheng Goh Z. Realty

    200 Swanton St Unit 416, Winchester, MA 01890
  • /14

    $4,550 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,826 Sq Ft
    • Apartment for Rent

    171 Swanton St Unit 77, Winchester, MA 01890

    Welcome home to this rare opportunity to reside in the highly sought after " Village" community in Winchester. This sunny & spacious Townhome boasts of fresh paint, newer floors, updated kitchen with stainless steel appliances, oversized rooms with an abundance of windows perfect for natural light, 2.5 baths one in with primary suite with a walk in closet, washer/dryer in unit, Central AC, a

    Alex Connor Capital Realty Group

    171 Swanton St Unit 77, Winchester, MA 01890
  • /32

    $6,600 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
  • /30

    $3,900 Per Month

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

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

    **NOT A SINGLE FAMILY HOME** 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

    Ryan Kelly Real Broker MA, LLC

    10-12 Webster St Unit 1, 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
  • /8

    $1,800 Per Month

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

    200 Swanton St Unit T34, Winchester, MA 01890

    Parkview Condominiums 1st flr Studio Suite with UTILITIES INCLUDED! Condo w/Patio view of the Gardens. Laundry room and Pool ; Avail 8/1! Close to Winchester Center and Purple line Train! View our 3D Tour - hardwood floors- PARKING! Patio that overlooks the Garden and the Pool!!! No pets, No smokers. First and Security. Application online.

    Kelly Catallo Realty ONE Group Cosmopolitan

    200 Swanton St Unit T34, Winchester, MA 01890
  • /22

    $3,400 Per Month

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Apartment for Rent

    63-65 Harvard St Unit 2, Winchester, MA 01890

    Three bedrooms and an office in this two floor, second floor unit in Winchester. Open kitchen with pantry, spacious living room. Two bedrooms on this main level. Upstairs two more rooms. Two full baths and laundry in the basement. One car garage parking and plenty of space for several cars. Shareable backyard. All of this in the Muraco School District.

    Beth Sager Group Keller Williams Realty Boston Northwest

    63-65 Harvard St Unit 2, 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
  • /5

    $2,250 Per Month

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

    200 Swanton St Unit 318, Winchester, MA 01890

    Beautifully renovated oversized one-bedroom condo at Parkview Condominium featuring an open floor plan and private balcony overlooking a serene Japanese garden and duck pond. Spacious primary bedroom offers room for a king-size bed and includes a walk-in closet. Updated kitchen, bathroom, and flooring provide years of low-maintenance living. Amenities include swimming pool, cabana, picnic

    Mike Huang Lewis & Joyce Real Estate

    200 Swanton St Unit 318, 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
  • /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
  • /9

    $3,500 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! This beautifully renovated 2-bedroom, 1-bath townhome offers the perfect blend of classic charm and modern updates, featuring hardwood floors throughout, recessed lighting, freshly painted interiors, and a stunning new kitchen with quartz countertops and stainless steel appliances. The updated bathroom showcases a walk-in tiled shower with a custom glass

    Issam Dib Skyline Realty

    63 Holland St Unit 63, Winchester, MA 01890
  • /31

    $5,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,420 Sq Ft
    • Apartment for Rent

    129 Washington St Unit 131, Winchester, MA 01890

    Prime Winchester location just moments from Winchester Center, within walking distance to elementary, middle, high school, downtown and commuter rail. Ideal for commuters and locals alike. This townhouse-style condo lives like a single-family, offering space, flow, and flexibility across four finished levels. The main living area is designed for how you actually live, with an open layout that

    Thomas Cote Leading Edge Real Estate

    129 Washington St Unit 131, 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
  • /29

    $5,200 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
  • /25

    $3,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,370 Sq Ft
    • Condo for Rent

    4 Stratton Dr Unit 408, Woburn, MA 01801

    Exceptional 2 bed/2 bath condo located on the top floor of 2023 built condo community in Woburn. Enjoy scenic sunset views from the living room balcony, effortlessly blending indoor & outdoor spaces for serene mornings or relaxing evenings. This thoughtfully designed residence features 2 spacious bedrooms & 2 full bathrooms, each with expansive walk-in closets and sunlit windows. The kitchen

    Noha Soliman Leading Edge Real Estate

    4 Stratton Dr Unit 408, Woburn, MA 01801

Why Live in Winchester

Winchester, MA, a peaceful Greater Boston suburb, has evolved from a rural farming community to a primarily residential town with a population of nearly 23,000. Located 8 miles north of Boston, Winchester is known for its grand New England homes, ranging from historic Colonial Revivals to modern Cape Cods and ranch styles. The town boasts one of the best school districts in the state, with Winchester Public Schools serving over 4,300 students and receiving high ratings. The private Acera School also offers quality education. Outdoor enthusiasts can enjoy Mystic Lakes State Park, Middlesex Fells Reservation, and the Tri-Community Greenway, which connects Winchester with Woburn and Stoneham. The town's downtown area, bordered by Wedge and Mill Ponds, features a variety of markets, restaurants, boutiques, and service shops. Community events such as Winchester Town Day, PRIDEFest, and summer concerts at Town Common foster a strong sense of community. Wright-Locke Farm, a 383-year-old sustainable conservancy, provides fresh organic produce and nature-based activities. Winchester is accessible via U.S. Route 3 and Interstates 93 and 95, with public transit options including the MBTA bus and commuter rail. Logan International Airport is about 11 miles away. The town has a lower crime risk compared to the national average, with recent data indicating a decrease in violent crimes.

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 $4,900 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 $196,000 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 $4,900 per month in Winchester, MA, renters typically need to show $14,700 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 26.7, 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 Downtown Woburn, Winchester Highlands, Arlington Center, Cummingsville and Arlington Heights, each with its own character and price range.

Rental Home Trends

Number of Homes for Rent
35
Median Rent
$4,900
Median Single Family Home Rent
$4,850
Median Townhouse Rent
$6,898
Median Condo Rent
$2,650
How to Rent a Home