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Winchester, MA Homes for Rent

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  • /9

    $1,890 per month

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

    200 Swanton St Unit 708, Winchester, MA 01890

    Available Oct 1Bright and inviting top-floor studio condo at the sought-after Parkview community. This unit features a private balcony overlooking the pond, perfect for enjoying peaceful views. Rent includes heat, hot water, electricity, and air conditioning for added convenience. Residents benefit from on-site laundry, parking, and access to the community pool. A well-maintained building in a

    Agent Photo

    Joan Powell

    Advisors Living - Merrimac

    (781) 653-7188

    200 Swanton St Unit 708, Winchester, MA 01890
  • /17

    $1,780 per month

    • 1 Bath
    • 350 Sq Ft
    • Condo for Rent

    200 Swanton St Unit 738, Winchester, MA 01890

    Available now! All utilities included! 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

    Agent Photo

    Joan Powell

    Advisors Living - Merrimac

    (617) 579-6010

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

    $3,195 - $7,845 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
  • /34

    $11,000 per month

    • 6 Beds
    • 4.5 Baths
    • 5,000 Sq Ft
    • House for Rent

    52 N Border Rd Unit 52, Winchester, MA 01890

    Grand and masterfully crafted home on this private road abutting 2200 acre Fells conservation land. This spacious home has 6 bedrooms, and 5 bathrooms. The stunning foyer welcomes you to the sprawling first floor. The custom work throughout each sun filled room is exquisite. Gourmet kitchen with top of the line appliances. Generous sized rooms to entertain guests. A private home office with built

    Dylan Archambault Archambault Real Estate

    52 N Border Rd Unit 52, 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
  • /20

    $4,400 per month

    • 3 Beds
    • 2.5 Baths
    • 1,830 Sq Ft
    • Apartment for Rent

    171 Swanton St Unit 65, Winchester, MA 01890

    Newly renovated Town home at The Village in Winchester offers an idyllic condominium community nestled near conservation land and the Aberjona River. This 3-bedroom home features a spacious living room with a gas fireplace and a dining area leading to a private patio. The kitchen was renovated in 2023. The main level includes a half bath and ample storage. Upstairs, the master bedroom has plenty

    Yuanming Cheng Dreamega International Realty LLC

    171 Swanton St Unit 65, Winchester, MA 01890
  • /30

    $2,695 per month

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

    6 Skillings Rd Unit 2-J, 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 2-J, Winchester, MA 01890
  • /3

    $4,800 per month

    • 3 Beds
    • 2.5 Baths
    • 2,339 Sq Ft
    • House for Rent

    12 Trinity Rd, Winchester, MA 01890

    Don’t miss the opportunity to lease this beautifully maintained multi-level single-family home, nestled on a quiet and private dead-end street. Recently updated with fresh interior paint and refinished hardwood floors, this spacious residence offers over 2,300 square feet of comfortable living space. Enjoy central A/C, a generous kitchen with an open-concept dining area—perfect for both everyday

    Michael Rauseo Better Homes and Gardens Real Estate - The Shanahan Group

    12 Trinity Rd, 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
  • /7

    $2,200 per month

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

    200 Swanton St Unit 713, Winchester, MA 01890

    Spacious top floor 1 bedroom with private deck with stunning pond views. Convenient location to public transportation, shopping and restaurants. Heat, hot water and electricity included. Laundry and extra storage in the building. 1 parking spot. No smoking and no pets.

    Brunna Henrique Keller Williams Realty Boston-Metro | Back Bay

    200 Swanton St Unit 713, 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
  • /19

    $8,000 per month

    • 4 Beds
    • 3 Baths
    • 2,666 Sq Ft
    • House for Rent

    10 Hillcrest Pkwy, Winchester, MA 01890

    An elegant property on one of Winchester's most beautiful residential side streets, facing the Middlesex Fells, with breathtaking seasonal views of the reservoir. Feels like a wooded retreat! Features 4 BR, 3 full BA; granite & stainless kitchen; a huge open-concept living area with 10ft+ ceilings, grand fireplace & wet bar; secluded screened patio, deck. Hardwood floors, designer light fixtures.

    Robyn Bonnett Coldwell Banker Realty - Lexington

    10 Hillcrest Pkwy, Winchester, MA 01890
  • /19

    $1,550 per month

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

    219 Washington St Unit 3, 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

    219 Washington St Unit 3, Winchester, MA 01890
  • /16

    $2,575 per month

    • 2 Beds
    • 2 Baths
    • 900 Sq Ft
    • Apartment for Rent

    35 Vine St Unit 306, Winchester, MA 01890

    Located at 35 Vine Street U:306, Winchester, MA, this residential property offers a superb opportunity to enjoy refined living. Situated on floor number 3, this home presents a wonderful chance to live in a comfortable residence in a vibrant community just steps to Winchester Center and Commuter Rail. The residence features two full bathrooms, providing convenience and privacy for yourself and

    Jill Shanley CJL Rentals & Property Management Co., Inc.

    35 Vine St Unit 306, Winchester, MA 01890
  • /13

    $2,695 per month

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

    6 Skillings Rd Unit 2, Winchester, MA 01890

    6 Skillings Rd Unit 2, Winchester, MA 01890
  • /24

    $6,900 per month

    • 4 Beds
    • 4 Baths
    • 3,639 Sq Ft
    • House for Rent

    31 Coolidge Rd, Winchester, MA 01890

    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 office with

    Carlos Xu Lexwin Realty

    31 Coolidge Rd, Winchester, MA 01890
  • /22

    $3,750 per month

    • 2 Beds
    • 1.5 Baths
    • 1,464 Sq Ft
    • Townhouse for Rent

    60 Lake St, Winchester, MA 01890

    Pond views just steps from your door! This move-in ready 2-bed, 1.5-bath townhouse at Wedge Pond Condominiums offers Winchester living at its best. The main level features hardwood floors, a bright living room, dining room with bow window, half bath, and a renovated kitchen. Upstairs you’ll find two bedrooms and a full bath, while the finished lower level provides flexible space for an office,

    60 Lake St, Winchester, MA 01890
  • /12

    $1,800 per month

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

    200 Swanton St Unit L6, Winchester, MA 01890

    A lobby level studio / one bedroom condo in the center of Winchester to rent. Beautiful views of the courtyard and many updates over the past few years, including granite countertops, sink and appliances. Well managed building has gone through some recent renovations and upgrades including new landscape, paved driveways and walkways. This Back Unit is overlooking The Pond. ALL utilities (heat,

    Weidong Li WINN Real Estate & Consulting

    200 Swanton St Unit L6, 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
  • /22

    $3,400 per month

    • 2 Beds
    • 1.5 Baths
    • 1,464 Sq Ft
    • Apartment for Rent

    60 Lake St Unit I, Winchester, MA 01890

    Pond views just steps from your door! This move-in ready 2-bed, 1.5-bath townhouse at Wedge Pond Condominiums offers Winchester living at its best. The main level features hardwood floors, a bright living room, dining room with bow window, half bath, and a renovated kitchen. Upstairs you’ll find two bedrooms and a full bath, while the finished lower level provides flexible space for an office,

    Yuwei Liao Hooli Homes Boston

    60 Lake St Unit I, 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
  • /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
  • /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
  • /6

    $2,150 per month

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

    200 Swanton St Unit T23, Winchester, MA 01890

    *NO FEE! $$$ PRICE BREAK and ALL UTILITIES INCLUDED!!!! Ground Level with Private Entrance. NO STAIRS! Lovely terrace level unit at Parkview available 9/1. This well cared for home includes dishwasher, on site laundry, parking,Situated in an very convenient location, near everything! Enjoy the beautifully landscaped common area with pool, cabana and picnic table. Super Value with ALL

    David Divecchia Berkshire Hathaway HomeServices Commonwealth Real Estate

    200 Swanton St Unit T23, Winchester, MA 01890
  • /7

    $2,375 per month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    35 Vine St Unit 302, Winchester, MA 01890

    Enjoy the ease of living in this stunning 1 bedroom apartment on upper floor of brick building with elevator and garage covered, 1 car parking. Conveniently located just steps to Winchester Center and Commuter Rail. Heat and hot water included. Central A/C. Dishwasher/disposal/over-the-stove microwave. Newly carpeted throughout. Laundry in building. Storage unit included. No pets/nos smoking.

    35 Vine St Unit 302, Winchester, MA 01890
  • /41

    $10,000 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
  • /4

    $2,000 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
  • /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
  • /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
  • /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
  • /45

    $2,800 - $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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /26

    $8,800 per month

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

    35 Thornberry Rd, Winchester, MA 01890

    One Month Free and No Broker Fee! 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,

    Frank Celeste Gibson Sotheby's International Realty

    35 Thornberry Rd, 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
  • /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
  • /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

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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.

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