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Winchester, MA Homes for Rent

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  • /17

    $1,780 per month

    • 1 Bath
    • 350 Sq Ft
    • Condo for Rent

    200 Swanton St Unit 738, Winchester, MA 01890

    Studio apartment on the 7th floor in Winchester with a private balcony overlooking Duck Pond. Heat, hot water, AC, and electricity included. Building amenities include an elevator, outdoor swimming pool, visitor parking, and 1 free parking pass (additional parking available at extra cost to HOA). Convenient location close to shopping, restaurants, and major highways. Enjoy comfortable and

    Agent Photo

    Joan Powell

    Advisors Living - Merrimac

    (617) 579-6010

    200 Swanton St Unit 738, Winchester, MA 01890
  • /24

    $3,195 - $7,782 per month

    Sanctuary Winchester North

    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

    25-35 River St, Winchester, MA 01890
  • /7

    $2,500 per month

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

    6 Skillings Rd Unit 2, Winchester, MA 01890

    Great two bedroom with hardwood floors, super sunny, updated kitchen and bath, in unit laundry, central A/C, good size bedrooms, one off street parking spot. Great location. 9/1 move in no pets.

    Kristen Day RE/MAX Realty Plus

    6 Skillings Rd Unit 2, Winchester, MA 01890
  • /20

    $2,585 - $7,000 per month

    Sanctuary Winchester West

    Studio - 3 Beds

    416 Cambridge St, Winchester, MA 01890

    The Sanctuary at Winchester West makes living your best life as easy as walking through your front door. Contemporary design and state-of-the-art amenities offer modern luxury at your fingertips. With shopping and a Whole Foods right next door, this community provides convenience at every turn.

    416 Cambridge St, Winchester, MA 01890
  • /36

    $3,800 per month

    • 3 Beds
    • 1.5 Baths
    • 1,000 Sq Ft
    • House for Rent

    24 Clematis St, Winchester, MA 01890

    Stunning 3-bed, 1.5-bath apartment at 24 Clematis St, Unit 2, Winchester, MA. This renovated home features a modern kitchen with white cabinets, butcher block counters, and appliances (range, oven, dishwasher, fridge, washer, dryer). Enjoy a cozy living room, elegant dining area, and marble-tiled bathroom. The chic staircase leads to three bright bedrooms. Relax in a private backyard with a

    William Dynan Keller Williams Realty Evolution

    24 Clematis St, Winchester, MA 01890
  • /15

    $1,700 per month

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

    200 Swanton St, Winchester, MA 01890

    Studio apartment on the 7th floor in Winchester with a private balcony overlooking Duck Pond. Heat, hot water, AC, and electricity included. Building amenities include an elevator, outdoor swimming pool, visitor parking, and 1 free parking pass (additional parking available at extra cost to HOA). Convenient location close to shopping, restaurants, and major highways. Enjoy comfortable and

    200 Swanton St, Winchester, MA 01890
  • /6

    $2,300 per month

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

    200 Swanton St Unit T23, Winchester, MA 01890

    Lovely terrace level unit at Parkview available 9/1. This well cared for home includes dishwasher, on site laundry, parking, in an 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 a must see!. Sorry No pets.

    David Divecchia Berkshire Hathaway HomeServices Commonwealth Real Estate

    200 Swanton St Unit T23, Winchester, MA 01890
  • /4

    $1,750 per month

    • Studio
    • 1 Bath
    • Condo for Rent

    2 Elmwood Ave Unit 14, Winchester, MA 01890

    This nice Studio 1 Bath place in the WINCHESTER area is available for 09-05-2025.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 conditions at the time the information was

    2 Elmwood Ave Unit 14, Winchester, MA 01890
  • /41

    $11,500 per month

    • 5 Beds
    • 3.5 Baths
    • 3,474 Sq Ft
    • House for Rent

    211 Forest St, Winchester, MA 01890

    FURNISHED ONLY 3 MONTH WINTER RENTAL. If you’ve been thinking of a kitchen renovation or addition but dread the chaos of construction, or maybe you're visiting one of our world renowned hospitals, our stunning 5-bedroom, 3.5-bathroom, 3,500-square-foot home in the coveted Muraco school district is available for a 3-month winter rental (January through March) while my family snowbirds in Florida.

    Michael Gilbert Stuart St James, Inc.

    211 Forest St, Winchester, MA 01890
  • /10

    $2,680 per month

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

    200 Swanton St, Winchester, MA 01890

    HEAT, HOT WATER, AC and ELECTRIC included. Enjoy scenic pond views from this beautifully updated second-floor condo, perfectly situated overlooking the pond. This two-bedroom unit features an inviting open-concept layout that flows seamlessly onto a spacious private balcony—ideal for relaxing or entertaining outdoors. Generous closet space is found throughout the home, with additional storage

    200 Swanton St, Winchester, MA 01890
  • /42

    $13,500 per month

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

    54 Wedgemere Ave, Winchester, MA 01890

    Exceptional living in this stunning Wedgemere Ave home w/ spectacular resort style back yard surrounded by mature plants and trees encompassing the gorgeous yard/setting. Completely updated throughout w/ custom high end finishes, open floor plan, wonderful chefs kitchen w/ Sub Zero- Wolf appliances, sunny breakfast/dining area w/ a wall of windows overlooking expansive back yard featuring

    Kim Covino Compass

    54 Wedgemere Ave, Winchester, MA 01890
  • /11

    $2,475 per month

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

    200 Swanton St, Winchester, MA 01890

    2-Bedroom Apartment with Pond Views – Available Now!This sunny 2-bedroom, 1-bathroom apartment offers beautiful views of the pond and a private balcony to enjoy them. Rent includes heat, hot water, electricity, and A/C for added convenience. Additional amenities include access to a pool, bike parking, storage, and one included parking spot, with the option to purchase extra parking

    200 Swanton St, Winchester, MA 01890
  • /42

    $6,500 per month

    • 4 Beds
    • 3.5 Baths
    • 3,516 Sq Ft
    • Apartment for Rent

    192 Cross St, Winchester, MA 01890

    Discover elegant living in this stunning Winchester duplex offering exceptional space and comfort across four thoughtfully designed levels. Ideal for both relaxation and entertaining, the home boasts an expansive kitchen flowing seamlessly into inviting dining and spacious family areas. Retreat upstairs to generously sized bedrooms, each designed for restful privacy, including the ensuite primary

    Anne Spry Barrett Sotheby's International Realty

    192 Cross St, Winchester, MA 01890
  • /30

    $2,750 per month

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

    6 Skillings Rd Unit 2j, Winchester, MA 01890

    Two bedroom one bath unit located right out of Winchester Center. Open loft style living room and kitchen. Two good size bedrooms and full bath with w/d in unit. Hardwood floors throughout unit. Lots of natural sun light, gas heat and gas cooking, central ac, attic storage, 1 or 2 car parking. Walk to many shops, restaurants, commuter rail, duck pond, library, etc. Close to Winchester Hospital.

    6 Skillings Rd Unit 2j, Winchester, MA 01890
  • /33

    $7,750 per month

    • 4 Beds
    • 3.5 Baths
    • 3,500 Sq Ft
    • House for Rent

    10 Farrow St, Winchester, MA 01890

    Single Family Home rental in Winchester. NO BROKERS FEE. Available 8/5, 8/15, 9/1. Completely rebuilt from ground up in 2019 w/Attached 1 Car Garage. 4 Beds, 3.5 baths & 3500SF w/ 2 dedicated home offices. Modern kitchen w/Quartz Countertops, Stainless Steel Appliances & Venting for cooking. Open concept has an Island connecting dining & living spaces. Sundrenched Living Room offers a wood

    Collin Bray Century 21 Cityside

    10 Farrow St, Winchester, MA 01890
  • /23

    $3,600 per month

    • 3 Beds
    • 2 Baths
    • 2,100 Sq Ft
    • Condo for Rent

    40 Florence St Unit 2, Winchester, MA 01890

    (All is just repainted, brand new kitchen floor and countertops - Ready to rent out) 3-Bed / 2 Full-bath apartment in a desirable Winchester neighborhood for rent. Situated at a quiet street, this three-bedroom and two-bathroom in a two-family house setting has a nice floor plan and decent flow. Hardwood floor throughout. It has a spacious eat-in kitchen with a pantry and with stainless

    40 Florence St Unit 2, Winchester, MA 01890
  • /18

    $2,000 per month

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

    200 Swanton St Unit L25, Winchester, MA 01890

    The sought after Parkview Condominium! Prime Winchester Location ! All newly PAINTED ! 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

    Ai Cheng Goh Z. Realty

    200 Swanton St Unit L25, Winchester, MA 01890
  • /10

    $2,600 per month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • House for Rent

    343 Washington St, Winchester, MA 01890

    343 Washington St, Winchester, MA 01890
  • /24

    $4,000 per month

    • 3 Beds
    • 1.5 Baths
    • 1,542 Sq Ft
    • House for Rent

    104 Wendell St, Winchester, MA 01890

    3-Bedroom single colonial house in Winchester for rent. Situated at a quiet neighborhood, this 3-bedroom and 1.5 bathroom single family house has a nice floor plan with a good kitchen. Hardwood floor throughout. The first floor has a spacious living room, an open concept kitchen and dining area. Kitchen is equipped with stainless appliances, granite counter tops and a slider that leads to the

    Weidong Li WINN Real Estate & Consulting

    104 Wendell St, Winchester, MA 01890
  • /4

    $2,250 per month

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

    7 Salem St, Winchester, MA 01890

    Charming "doll house" cottage. Lovely, historic one-bedroom home situated on conveniently located lot in beautiful Winchester. Walk to restaurants, MBTA buses & trains. 2 Off street Parking spaces.

    7 Salem St, Winchester, MA 01890
  • /20

    $2,950 per month

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

    37-39 Spruce St Unit 37, Winchester, MA 01890

    Welcome to this beautifully home in a prime Winchester location! Recently gut renovated and in pristine condition, this unit is truly move-in ready.The open floor plan features gleaming hardwood floors, a spacious living area, and a stunning chef’s kitchen with granite countertops, stainless steel appliances, new cabinetry, and a charming breakfast nook with wet bar. Enjoy the convenience of

    Kim Covino Compass

    37-39 Spruce St Unit 37, Winchester, MA 01890
  • /10

    $3,300 per month

    • 2 Beds
    • 2.5 Baths
    • 1,634 Sq Ft
    • Condo for Rent

    3 Conant Rd Unit 1, Winchester, MA 01890

    2 bed and 2.5 bath located in Winchester. Easy access to downtown and public transportation!

    3 Conant Rd Unit 1, Winchester, MA 01890
  • /26

    $8,800 per month

    • 4 Beds
    • 3.5 Baths
    • 3,500 Sq Ft
    • House for Rent

    35 Thornberry Rd, Winchester, MA 01890

    Large Sun-filled Windows, Contemporary, Minimalist, and Modern Design. A truly rare opportunity to rent this magnificent single-family home in one of Winchester’s most desirable neighborhoods. The home was ground-up construction in 2010 with over 3,500 square feet of living space. Its open concept, large loft-style office / second living room area, four bedrooms, three and a half bathrooms,

    Frank Celeste Gibson Sotheby's International Realty

    35 Thornberry Rd, Winchester, MA 01890
  • /12

    $3,200 per month

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

    65 Highland Ave Unit 1, Winchester, MA 01890

    1 bed and 1 bath located in Winchester Highlands. Easy access to downtown and public transportation!

    65 Highland Ave Unit 1, Winchester, MA 01890
  • /26

    $5,995 per month

    • 2 Beds
    • 2.5 Baths
    • 2,173 Sq Ft
    • Condo for Rent

    23 Elmwood Ave Unit C, Winchester, MA 01890

    Incredible opportunity to live carefree in vibrant downtown Winchester. Recently built condo featuring almost 2,200 interior SqFt of beautifully designed space, open concept living, hardwood floors and over sized windows. Three generous bedrooms, two full and one half bath, in-unit laundry, gas fireplace and two off-street parking makes this condo a true joy. A rare find in the heart of downtown

    Catherine Albiani Better Homes and Gardens Real Estate - The Shanahan Group

    23 Elmwood Ave Unit C, Winchester, MA 01890
  • /33

    $4,000 per month

    • 4 Beds
    • 1.5 Baths
    • 1,300 Sq Ft
    • Townhouse for Rent

    848 Main St, Winchester, MA 01890

    **Elegant Winchester Home Near Wright Pond and Downtown Amenities**Spacious 4-bedroom, 1.5-bathroom townhouse style unit - located close to Winchester Center, with a park across the street and Wright Pond and Park nearby.Enjoy top rated Winchester schools nearby.Open-concept kitchen with granite countertops, island, pantry, and space for your table, plus hardwood floors, central

    848 Main St, Winchester, MA 01890
  • /13

    $3,200 per month

    • 2 Beds
    • 1.5 Baths
    • 1,331 Sq Ft
    • Condo for Rent

    29 Vine St Unit 3, Winchester, MA 01890

    Two-level apartment with two bedrooms, two baths, and a parking space. Possible second parking space - negotiable. Large kitchen space with stainless steel appliances. Spacious off-living room, fenced porch. In-unit laundry. Walk-in closet. Dream location: t-station, shops, bike path, cafes, and much more, all within a 5-minute walk. Beautiful views of the Fells. First month and security deposit.

    Jasmina Cesic Danehy Realty Corp.

    29 Vine St Unit 3, Winchester, MA 01890
  • /6

    $2,600 per month

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

    343 Washington St Unit 343, Winchester, MA 01890

    Beautiful, charming 5-room, 2 bedrooms 1 bath apartment with 2 car parking (tandem, 1 in the garage) in 2 Family home. Hardwood floors throughout, 2 porches, a yard, and a washer and dryer hookup in basement. Close to Winchester Town center and commuter rail and easy access to Route 2, Route 3, Route 93, and Route 95. No pets and smoking. First, last and security deposit. Must have good credit

    343 Washington St Unit 343, Winchester, MA 01890
  • /35

    $7,500 per month

    • 3 Beds
    • 2.5 Baths
    • 2,900 Sq Ft
    • Apartment for Rent

    846 Main St Unit III, Winchester, MA 01890

    No equal. Stunning, newer construction luxury Penthouse available for rent. Elevator access steps from private, heated, two (2) car garage parking completes the 2,900 square feet of open, fabulous, three (3) bedroom, two and half (2-1/2) bath space. Ten (10') foot ceilings throughout this airy, bright, light filled remarkable residence. Exquisite hardwood floors compliment the generous white trim

    Anthony Marino The Marino Group Collection

    846 Main St Unit III, Winchester, MA 01890
  • /11

    $2,200 per month

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

    253 Swanton St Unit 428, Winchester, MA 01890

    1 bed and 1 bath located in Winchester Highlands. Easy access to downtown and public transportation!

    253 Swanton St Unit 428, Winchester, MA 01890
  • /36

    $7,500 per month

    • 3 Beds
    • 2.5 Baths
    • 2,900 Sq Ft
    • Apartment for Rent

    846 Main St Unit IV, Winchester, MA 01890

    No equal. Stunning, newer construction luxury Penthouse available for rent. Elevator access steps from private, heated, two (2) car garage parking completes the 2,900 square feet of open, fabulous, three (3) bedroom, two and half (2-1/2) bath space. Ten (10') foot ceilings throughout this airy, bright, light filled remarkable residence. Exquisite hardwood floors compliment the generous white trim

    Anthony Marino The Marino Group Collection

    846 Main St Unit IV, Winchester, MA 01890
  • /23

    $4,000 per month

    • 2 Beds
    • 2.5 Baths
    • 1,700 Sq Ft
    • Condo for Rent

    41 Church St Unit 1, Winchester, MA 01890

    2 bed and 2.5 bath located in Winchester. Easy access to downtown and public transportation!

    41 Church St Unit 1, Winchester, MA 01890
  • /41

    $9,400 per month

    • 5 Beds
    • 4.5 Baths
    • 5,016 Sq Ft
    • House for Rent

    22 Amberwood Dr, Winchester, MA 01890

    Fabulous rental opportunity with full wing of an additional in-law suite for multi-generational living at its best. Beautiful designers’ grade high-end finishes throughout! Features separate side entry with inviting south-facing covered porch, a dramatic two-story foyer/ceiling, and the main kitchen that flows into an additional meal prep kitchen area with integrated appliances – Thermador

    Anita Lin Coldwell Banker Realty - Lexington

    22 Amberwood Dr, Winchester, MA 01890
  • /11

    $3,500 per month

    • 3 Beds
    • 1 Bath
    • 1,400 Sq Ft
    • Condo for Rent

    534 Washington St Unit 2, Winchester, MA 01890

    Welcome to this 3-bedroom spacious and bright apartment near the North Reservoir and Middlesex Fells Reservation!!! With many windows, the unit is flooded with natural light. The open-concept living space features a hardwood floor and recessed lighting. Cook with joy in a kitchen that includes granite countertops, a 5-burner stainless steel gas cooktop, and abundant cabinetry. All 3 bedrooms

    534 Washington St Unit 2, Winchester, MA 01890
  • /14

    $2,800 per month

    • 2 Beds
    • 2 Baths
    • 1,452 Sq Ft
    • Apartment for Rent

    273 Cross St Unit 273, Winchester, MA 01890

    Available September 1, 2025! Don’t miss this charming and spacious 6-room duplex townhouse—ready for you to move right in! This well-maintained home features a bright and airy living room and formal dining area, perfect for relaxing or entertaining. The renovated kitchen boasts granite countertops, modern finishes, and a walk-out to your private fenced yard—ideal for seamless indoor-outdoor

    coldown jx Phoenix Real Estate Partners, LLC

    273 Cross St Unit 273, Winchester, MA 01890
  • /45

    $2,845 - $5,235 per month

    The Mave

    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

    225 Fallon Rd, Stoneham, MA 02180
  • /34

    $15,000 per month

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

    20 Amberwood Dr, Winchester, MA 01890

    Stunning 8800 sq ft brand-new contemporary in one of Winchester's favorite neighborhoods. A gracious foyer w/ high ceiling welcomes you to this elegant home loaded with natural light and architectural detail. Custom features include a gourmet eat-in kitchen w/ granite countertops, high-end appliances, secondary prep area, and fabulous outside dining options from the oversized deck. The

    Dan Li Keller Williams Realty

    20 Amberwood Dr, Winchester, MA 01890
  • /39

    $3,500 per month

    • 3 Beds
    • 1 Bath
    • 9,999 Sq Ft
    • Condo for Rent

    10 Cross St Unit 1, Woburn, MA 01801

    Welcome to this charming 3-bedroom, 1.5-bathroom apartment in Woburn! This delightful home boasts two off-street parking spaces. Enjoy the comfort of a spacious back yard and the ease of a dishwasher in the kitchen. With laundry facilities located in the basement, managing chores becomes a breeze. The apartment offers three large bedrooms, a cozy living room, and a lovely dining room, ensuring

    10 Cross St Unit 1, Woburn, MA 01801
  • /38

    $7,450 per month

    • 4 Beds
    • 4 Baths
    • 4,650 Sq Ft
    • House for Rent

    31 Coolidge Rd, Winchester, MA 01890

    Available now! Welcome to this beautifully renovated and maintained colonial at a very quiet street in a desirable neighborhood with easy commute to schools, Boston, highways and MBTA train stations. The 1st floor offers a foyer with formal dining room and living room in either sides. The kitchen, with island and full breakfast/dining area, flows into a family room that transitions to a private

    Carlos Xu Lexwin Realty

    31 Coolidge Rd, Winchester, MA 01890
  • /26

    $3,300 per month

    • 3 Beds
    • 1.5 Baths
    • 9,999 Sq Ft
    • Condo for Rent

    8 Cross St Unit 1, Woburn, MA 01801

    8 Cross St Unit 1, Woburn, MA 01801

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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

What are the most popular neighborhoods in Winchester, MA for renters?
The most popular neighborhoods in Winchester, MA for renters are The Flats, North Main, West Side, Downtown Woburn and Winchester Highlands.
What are the most popular zip codes in Winchester, MA for renters?
The most popular zip codes in Winchester, MA for renters include 01890, 01801, 02155, 02474 and 02420.
How to Rent a Home