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Newest Homes for Rent in Winchester, MA

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  • 416 Cambridge St, Winchester, MA 01890
    416 Cambridge St, Winchester, MA 01890
    416 Cambridge St, Winchester, MA 01890
    /20

    Starting at $2,410 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
  • 25-35 River St, Winchester, MA 01890
    25-35 River St, Winchester, MA 01890
    25-35 River St, Winchester, MA 01890
    /24

    Starting at $2,925 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
  • 225 Fallon Rd, Stoneham, MA 02180
    225 Fallon Rd, Stoneham, MA 02180
    225 Fallon Rd, Stoneham, MA 02180
    /44

    Starting at $2,695

    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
  • 5 Stoneham St, Woburn, MA 01801
    5 Stoneham St, Woburn, MA 01801
    5 Stoneham St, Woburn, MA 01801
    /14

    $4,625

    Total Monthly Price

    • 4 Beds
    • 2.5 Baths
    • 2,150 Sq Ft
    • House for Rent

    5 Stoneham St, Woburn, MA 01801

    4 Bedrooms | 2.5 Baths | Renovated Single Family Near Winchester & Commuter RailFreshly renovated single-family home located in a quiet, scenic neighborhood on the Winchester line. This spacious home offers 4 bedrooms, 2.5 bathrooms, central A/C, and an attached 1-car garage with EV charger hookup, plus ample off-street parking.The main level features a brand-new kitchen with

    5 Stoneham St, Woburn, MA 01801
  • 35 Loring Ave Unit 1L, Winchester, MA 01890
    35 Loring Ave Unit 1L, Winchester, MA 01890
    35 Loring Ave Unit 1L, Winchester, MA 01890
    /5

    $1,895

    Total Monthly Price

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

    35 Loring Ave Unit 1L, Winchester, MA 01890

    Unit is located don the fist floor of a multi family home. Kitchen with gas cooking, (no dishwasher) Living room , dining room, pantry and a cedar closet. Unit is older but great charm! w/d unit in basement, 2 off street parking spots, close to Winchester hospital, ctr, bus.transfer station sticker required for trashFirst and security, tenant at willno pets

    35 Loring Ave Unit 1L, Winchester, MA 01890
  • 200 Swanton St Unit 705, Winchester, MA 01890
    200 Swanton St Unit 705, Winchester, MA 01890
    200 Swanton St Unit 705, Winchester, MA 01890
    /14

    $2,800 Plus Fees

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

    200 Swanton St Unit 705, Winchester, MA 01890

    Property Id: 2813835 All utilities included (heat, hot water, and electricity) in this top-floor 2-bedroom, 1-bath condo with stunning views over the treetops and duck pond. Its 7th-floor perch offers exceptional privacy, quiet, and floor-to-ceiling, south-facing windows that fill the home with natural light. One cat allowed. The kitchen and bath were fully renovated several years ago, and

    200 Swanton St Unit 705, Winchester, MA 01890
  • 35 Loring Ave Unit 1L, Winchester, MA 01890
    35 Loring Ave Unit 1L, Winchester, MA 01890
    35 Loring Ave Unit 1L, Winchester, MA 01890
    /5

    $1,895

    Total Monthly Price

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

    35 Loring Ave Unit 1L, Winchester, MA 01890

    Unit is located don the fist floor of a multi family home. Kitchen with gas cooking, (no dishwasher) Living room , dining room, pantry and a cedar closet. Unit is older but great charm! w/d unit in basement, 2 off street parking spots, close to Winchester hospital, ctr, bus.transfer station sticker required for trashFirst and security, tenant at willno pets

    35 Loring Ave Unit 1L, Winchester, MA 01890
  • 200 Swanton St Unit 705, Winchester, MA 01890
    200 Swanton St Unit 705, Winchester, MA 01890
    200 Swanton St Unit 705, Winchester, MA 01890
    /14

    $2,800 Plus Fees

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

    200 Swanton St Unit 705, Winchester, MA 01890

    Property Id: 2813835 All utilities included (heat, hot water, and electricity) in this top-floor 2-bedroom, 1-bath condo with stunning views over the treetops and duck pond. Its 7th-floor perch offers exceptional privacy, quiet, and floor-to-ceiling, south-facing windows that fill the home with natural light. One cat allowed. The kitchen and bath were fully renovated several years ago, and

    200 Swanton St Unit 705, Winchester, MA 01890
  • 200 Swanton St Unit 738, Winchester, MA 01890
    200 Swanton St Unit 738, Winchester, MA 01890
    200 Swanton St Unit 738, Winchester, MA 01890
    /7

    $1,880 Per Month

    • 1 Bath
    • 350 Sq Ft
    • Condo for Rent

    200 Swanton St Unit 738, Winchester, MA 01890

    Welcome to 200 Swanton Street, Unit 738—a top-floor studio condominium offering comfortable, convenient, and low-maintenance living. All utilities are included, making monthly expenses simple. Enjoy laundry facilities in the building, additional storage downstairs for an extra fee, and a pool.

    Agent Photo

    Joan Powell

    REMAX Andrew Realty Services

    200 Swanton St Unit 738, Winchester, MA 01890
  • 79 Church St Unit 1, Winchester, MA 01890
    79 Church St Unit 1, Winchester, MA 01890
    79 Church St Unit 1, Winchester, MA 01890
    /19

    $4,400 Per Month

    • 3 Beds
    • 1.5 Baths
    • 2,000 Sq Ft
    • Apartment for Rent

    79 Church St Unit 1, Winchester, MA 01890

    Rare opportunity to rent an exceptionally spacious home on historic Church Street in the heart of Winchester! Offering over 2000 sq. ft. of living space, this charming Victorian features 3 generous bedrooms, 1.5 baths, a grand foyer, spacious living and dining rooms, and an eat-in kitchen with granite countertops and gas cooking. High ceilings, hardwood floors, original architectural details and

    Anna Mean AC Realty

    79 Church St Unit 1, Winchester, MA 01890
  • 7 Park Ave Unit 7, Winchester, MA 01890
    7 Park Ave Unit 7, Winchester, MA 01890
    7 Park Ave Unit 7, Winchester, MA 01890
    /37

    $4,200 Per Month

    • 4 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • Apartment for Rent

    7 Park Ave Unit 7, Winchester, MA 01890

    This luxurious townhome is now available for immediate occupancy. Spanning two floors, it boasts an exceptional layout. The main floor is particularly impressive, featuring a primary bedroom, an additional bedroom, Open Concept living room and dining area, and a bright, inviting eat-in kitchen. The kitchen is equipped with ample cabinets, counter space, and stainless steel appliances. Natural

    Chris Barnard Barnard Real Estate Advisors, LLC

    7 Park Ave Unit 7, Winchester, MA 01890
  • 303 Washington St Unit 1, Winchester, MA 01890
    303 Washington St Unit 1, Winchester, MA 01890
    303 Washington St Unit 1, Winchester, MA 01890
    /18

    $3,700 Per Month

    • 3 Beds
    • 1 Bath
    • 1,700 Sq Ft
    • Apartment for Rent

    303 Washington St Unit 1, Winchester, MA 01890

    Prime location close to town! Spacious and beautifully maintained 3-bedroom unit in the heart of Winchester, offering a blend of classic character and thoughtful updates. This condo features generously sized rooms with high ceilings, oversized windows, hardwood floors, beautiful original woodwork, crown molding, and timeless architectural details. The layout includes a welcoming living room with

    Kim Covino Compass

    303 Washington St Unit 1, Winchester, MA 01890
  • 16 Lochwan St Unit 16, Winchester, MA 01890
    16 Lochwan St Unit 16, Winchester, MA 01890
    16 Lochwan St Unit 16, Winchester, MA 01890
    /25

    $2,600 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,120 Sq Ft
    • Apartment for Rent

    16 Lochwan St Unit 16, Winchester, MA 01890

    Enjoy all that Winchester has to offer from this well located two-bedroom, one and a half bath rental at 16 Lochwan Street in Winchester, MA. This home offers a comfortable, practical layout with living and dining space, a functional kitchen, two bedrooms, and both a full and half bath. Two off-street parking spaces add wonderful convenience, and the location provides easy access to Winchester’s

    Melanie Lentini Leading Edge Real Estate

    16 Lochwan St Unit 16, Winchester, MA 01890
  • 115 Washington St Unit 1B, Winchester, MA 01890
    115 Washington St Unit 1B, Winchester, MA 01890
    115 Washington St Unit 1B, Winchester, MA 01890
    /21

    $2,700 Per Month

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

    115 Washington St Unit 1B, Winchester, MA 01890

    Best rental on the market in Winchester! This Beautifully updated one bedroom and one bathroom condo is avaiable for rent. The enter island kitchen opens up to a bright living and dining room area. This home boasts of all new kitchen appliances, heat pump (heat and AC), efinished hardwood floors, & recessed dimmable lighting. California closets in both closets in the bedroom, laundry room with

    Leah Pennini Gamut Group LLC

    115 Washington St Unit 1B, Winchester, MA 01890
  • 10 Winchester Place Unit 102, Winchester, MA 01890
    10 Winchester Place Unit 102, Winchester, MA 01890
    10 Winchester Place Unit 102, Winchester, MA 01890
    /66

    $4,200

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,707 Sq Ft
    • Condo for Rent

    10 Winchester Place Unit 102, Winchester, MA 01890

    Spacious and sunny corner unit condo at Winchester Place - Beautifully appointed unit with custom stenciled paint, "gold" dining room ceiling, living room with custom built-ins and gas fireplace, hardwood flooring throughout, new kitchen appliances, large walk in closet in main bedroom; oversized shower and large soaking tub in main bathroom which was recently renovated. Private balcony for your

    10 Winchester Place Unit 102, Winchester, MA 01890
  • 24 Lebanon St Unit 1, Winchester, MA 01890
    24 Lebanon St Unit 1, Winchester, MA 01890
    24 Lebanon St Unit 1, Winchester, MA 01890
    /16

    $2,650 Per Month

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • Apartment for Rent

    24 Lebanon St Unit 1, Winchester, MA 01890

    This great first floor 2 bedroom home is bright and spacious. The entry hall leads to living room, dining room, and kitchen The full bath is flanked by 2 bedrooms. Eat in kitchen with pantry is spacious enough to have a dining table. Tenant pays for gas heat, electricity, hot water, snow removal & refuse removal. Landlord pays for landscaping (grounds maintenance), water, sewer & provides laundry

    Anne Spry Barrett Sotheby's International Realty

    24 Lebanon St Unit 1, Winchester, MA 01890
  • 5 Quigley Ct Unit 5, Winchester, MA 01890
    5 Quigley Ct Unit 5, Winchester, MA 01890
    5 Quigley Ct Unit 5, Winchester, MA 01890
    /14

    $3,400 Per Month

    • 3 Beds
    • 1.5 Baths
    • Apartment for Rent

    5 Quigley Ct Unit 5, Winchester, MA 01890

    Great opportunity to rent this spacious 3-bedroom duplex offering three levels of living space, tucked away on a quiet dead-end street. Freshly painted throughout, the unit features new flooring, an updated kitchen equipped with a stove, dishwasher, and refrigerator, three generously sized bedrooms, and 1.5 bathrooms. The basement offers additional storage space, with a washer and dryer available

    Anna Mean AC Realty

    5 Quigley Ct Unit 5, Winchester, MA 01890
  • 10 Winchester Place Unit 102, Winchester, MA 01890
    10 Winchester Place Unit 102, Winchester, MA 01890
    10 Winchester Place Unit 102, Winchester, MA 01890
    /66

    $4,200

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,707 Sq Ft
    • Condo for Rent

    10 Winchester Place Unit 102, Winchester, MA 01890

    Spacious and sunny corner unit condo at Winchester Place - Beautifully appointed unit with custom stenciled paint, "gold" dining room ceiling, living room with custom built-ins and gas fireplace, hardwood flooring throughout, new kitchen appliances, large walk in closet in main bedroom; oversized shower and large soaking tub in main bathroom which was recently renovated. Private balcony for your

    10 Winchester Place Unit 102, Winchester, MA 01890
  • 353 Washington St, Arlington, MA 02474
    353 Washington St, Arlington, MA 02474
    353 Washington St, Arlington, MA 02474
    /25

    $1,500

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 300 Sq Ft
    • House for Rent

    353 Washington St, Arlington, MA 02474

    Hi there! We have two bedrooms in a stand-alone house on Washington St. in Arlington. I live here with my daughter. The kitchen and baths are well updated, and the house is surprisingly well-insulated against the heat and cold. Common areas are open for all to enjoy and fill and decorate as you like. Unless you have terrible taste. :)The basement room is half the footprint of the house,

    353 Washington St, Arlington, MA 02474
  • 666 Main St Unit 315-3, Winchester, MA 01890
    666 Main St Unit 315-3, Winchester, MA 01890
    666 Main St Unit 315-3, Winchester, MA 01890
    /37

    $3,300 Per Month

    • 2 Beds
    • 2 Baths
    • 1,025 Sq Ft
    • Condo for Rent

    666 Main St Unit 315-3, Winchester, MA 01890

    Enjoy easy living at Wedgewood Place, a sought-after condominium community in the heart of Winchester Center. This spacious 2-bedroom, 2-bath home offers a bright, open layout with a wood-burning fireplace and a great balcony. The updated kitchen flows seamlessly into the living and dining areas, creating an inviting space for everyday living and entertaining. The generous primary suite features

    Kim Covino Compass

    666 Main St Unit 315-3, Winchester, MA 01890
  • 79 Bacon St Unit 79, Winchester, MA 01890
    79 Bacon St Unit 79, Winchester, MA 01890
    79 Bacon St Unit 79, Winchester, MA 01890
    /41

    $4,950 Per Month

    • 5 Beds
    • 2 Baths
    • 2,174 Sq Ft
    • Apartment for Rent

    79 Bacon St Unit 79, Winchester, MA 01890

    Welcome to this spacious 3-story Colonial, where timeless curb appeal meets modern living. A bluestone path invites you to the main entry, setting the tone for a home designed for both comfort and sophistication. Inside, expansive living and dining rooms showcase wood trim and custom built-ins, while hardwood floors and oversized replacement windows flood the space with natural light. The heart

    Gayle Winters Compass

    79 Bacon St Unit 79, Winchester, MA 01890
  • 28 East St, Winchester, MA 01890
    28 East St, Winchester, MA 01890
    28 East St, Winchester, MA 01890
    /12

    $3,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,620 Sq Ft
    • Apartment for Rent

    28 East St, Winchester, MA 01890

    Spacious and well-maintained 3-bedroom, 2-bath townhouse featuring three levels of living space, with a large private yard and a storage shed. Enjoy hardwood floors throughout, a fully equipped kitchen with stainless steel appliances, and a finished basement with laundry and abundant storage space. The property includes 4 off-street parking spaces on a paved driveway. Conveniently located with an

    Jennifer Zhao HMW Real Estate, LLC

    28 East St, Winchester, MA 01890
  • 7 Ridge St, Winchester, MA 01890
    7 Ridge St, Winchester, MA 01890
    7 Ridge St, Winchester, MA 01890
    /28

    $3,200 Per Month

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

    7 Ridge St, Winchester, MA 01890

    Welcome to this charming 2-bedroom, 1.5-bath rental located on the desirable west side of Winchester. Offering three levels of living space, this home provides plenty of room to spread out and enjoy a comfortable, flexible layout. Beautiful hardwood floors add warmth and character throughout, while the level, partially fenced backyard provides a wonderful private outdoor space for relaxing,

    Shannon Jenkins RE/MAX Realty Experts

    7 Ridge St, Winchester, MA 01890
  • 159 Cross St Unit 159, Winchester, MA 01890
    159 Cross St Unit 159, Winchester, MA 01890
    159 Cross St Unit 159, Winchester, MA 01890
    /19

    $3,900 Per Month

    • 3 Beds
    • 3 Baths
    • 1,900 Sq Ft
    • House for Rent

    159 Cross St Unit 159, Winchester, MA 01890

    Wonderful opportunity to rent a single family home in Winchester. Main level welcomes you in to a fireplaced Livingroom with hardwood floors and formal dining room with direct access to Eat-in Kitchen featuring granite counters, tile floor and good storage. Second floor offers an over sized full bath with tile floor and three bedrooms all with hardwood floors. Lower level is finished with tile

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

    159 Cross St Unit 159, Winchester, MA 01890
  • 10-12 Webster St Unit 1, Winchester, MA 01890
    10-12 Webster St Unit 1, Winchester, MA 01890
    10-12 Webster St Unit 1, Winchester, MA 01890
    /31

    $3,700 Per Month

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

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

    Spacious 4-bedroom, 2-bath apartment available for immediate occupancy in a two-family home just minutes from Winchester Center. Please note: This is NOT a single-family home. This unique unit occupies the entire first floor and finished lower level. The main level features hardwood floors throughout, a living room, dining room, two spacious bedrooms, a full bath, and an eat-in kitchen with a new

    Ryan Kelly Real Broker MA, LLC

    10-12 Webster St Unit 1, Winchester, MA 01890
  • 25 Berkshire Dr, Winchester, MA 01890
    25 Berkshire Dr, Winchester, MA 01890
    25 Berkshire Dr, Winchester, MA 01890
    /38

    $6,500 Per Month

    • 3 Beds
    • 3 Baths
    • 2,443 Sq Ft
    • House for Rent

    25 Berkshire Dr, Winchester, MA 01890

    This beautifully renovated home offers over 2,400 sq ft of thoughtfully designed living space across two levels. The home blends modern finishes with functional comfort, making it ideal for today's lifestyle. Step inside to find a spacious open layout enhanced by high-quality updates throughout. The kitchen, baths, and mudroom feature custom cabinetry with high end Spanish panels, dovetail

    Nadia Mounsif McCaul & Mounsif Real Estate Group LLC

    25 Berkshire Dr, Winchester, MA 01890
  • 60 Graystone Cir Unit 60, Winchester, MA 01890
    60 Graystone Cir Unit 60, Winchester, MA 01890
    60 Graystone Cir Unit 60, Winchester, MA 01890
    /39

    $6,500 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,947 Sq Ft
    • Apartment for Rent

    60 Graystone Cir Unit 60, Winchester, MA 01890

    Meticulously maintained, 2/3-bedroom, 2.5-bath townhome with 2 car garage. The kitchen features custom cabinets, granite countertops, high-end stainless steel appliances and gleaming hardwood floors. The living/dining room combo features hardwood floors, gas fireplace, cathedral ceilings along with french doors that open to a private patio with gas grill. Spacious first floor primary suite boasts

    Pirani & Wile Group Gibson Sotheby's International Realty

    60 Graystone Cir Unit 60, Winchester, MA 01890
  • 111 Highland Ave, Winchester, MA 01890
    111 Highland Ave, Winchester, MA 01890
    111 Highland Ave, Winchester, MA 01890
    /21

    $5,500 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,632 Sq Ft
    • House for Rent

    111 Highland Ave, Winchester, MA 01890

    Welcome to this spacious and charming Colonial offering beautiful architectural character, a flexible floor plan, and generous living space across multiple levels.Step into the welcoming foyer and discover a bright, inviting home featuring a fireplaced living room with beamed ceilings and oversized windows, complemented by a sun-filled adjoining sunroom.The beautiful kitchen features granite

    Michelle Li Zhensight Realty LLC

    111 Highland Ave, Winchester, MA 01890
  • 4 Border St Unit 4, Woburn, MA 01801
    4 Border St Unit 4, Woburn, MA 01801
    4 Border St Unit 4, Woburn, MA 01801
    /12

    $2,300 Per Month

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

    4 Border St Unit 4, Woburn, MA 01801

    Available September 1st! A two bedroom, kitchen, living room and full bath. This unit has hardwood floors and many windows letting in plenty of sunlight. Basement has laundry hook ups and 1 spot for parking. Convenient to Shopping, Schools, Restaurants, Library, Horn Pond and Major Highway access. S.howings will begin August 18th

    Robin Griffiths J. Mulkerin Realty

    4 Border St Unit 4, Woburn, MA 01801
  • 161 Highland Ave Unit n/a, Winchester, MA 01890
    161 Highland Ave Unit n/a, Winchester, MA 01890
    161 Highland Ave Unit n/a, Winchester, MA 01890
    /28

    $7,500 Per Month

    • 6 Beds
    • 3 Baths
    • 3,000 Sq Ft
    • House for Rent

    161 Highland Ave Unit n/a, Winchester, MA 01890

    Enjoy the best of Winchester living in this beautifully maintained six-bedroom, two-and-a-half-bath Colonial, ideally situated just moments from the Middlesex Fells Reservation. Available August 1, this spacious home offers a versatile layout designed for comfortable everyday living, with generous room sizes, abundant natural light, and central HVAC for year-round comfort. Outside, the

    Lisa Godwin Gibson Sotheby's International Realty

    161 Highland Ave Unit n/a, Winchester, MA 01890
  • 270 Cross St Unit SF, Winchester, MA 01890
    270 Cross St Unit SF, Winchester, MA 01890
    270 Cross St Unit SF, Winchester, MA 01890
    /34

    $6,000 Per Month

    • 4 Beds
    • 4 Baths
    • 2,700 Sq Ft
    • House for Rent

    270 Cross St Unit SF, Winchester, MA 01890

    Beautifully renovated 4BR/4BA home in Winchester’s desirable Lynch School District offering three levels of modern living. The main floor features a dedicated office, hardwood floors, mini-split cooling, a wood-burning fireplace, 2-zone Nest heating, and a spacious kitchen with quartz countertops and stainless steel appliances. The walkout lower level is perfect for an in-law or au-pair suite

    The Abundant Group Real Broker MA, LLC

    270 Cross St Unit SF, Winchester, MA 01890
  • 22 Baldwin St, Winchester, MA 01890
    22 Baldwin St, Winchester, MA 01890
    22 Baldwin St, Winchester, MA 01890
    /21

    $4,200 Per Month

    • 3 Beds
    • 2 Baths
    • 1,678 Sq Ft
    • House for Rent

    22 Baldwin St, Winchester, MA 01890

    Beautifully renovated single-family home on a quiet cul-de-sac in desirable Winchester. Situated on a spacious 9,500± sq. ft. lot, this move-in-ready home features newly finished hardwood floors throughout, an open-concept living and dining area, an updated kitchen with gas cooking, a cozy family room with a wood-burning fireplace, and a full bath on the main level. Upstairs offers three spacious

    Qian Han JW Real Estate Services, LLC

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

    $1,950 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! No pets. No smoking of any substances. Large bedroom for a king-size bed or twins and includes a

    Ai Cheng Goh Z. Realty

    200 Swanton St Unit 416, Winchester, MA 01890
  • 63-65 Harvard St Unit 2, Winchester, MA 01890
    63-65 Harvard St Unit 2, Winchester, MA 01890
    63-65 Harvard St Unit 2, Winchester, MA 01890
    /22

    $3,200 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
  • 48 Spruce St Unit 1, Winchester, MA 01890
    48 Spruce St Unit 1, Winchester, MA 01890
    48 Spruce St Unit 1, Winchester, MA 01890
    /29

    $5,000 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 The Archambault Group

    48 Spruce St Unit 1, Winchester, MA 01890
  • 60 Lake St Unit D, Winchester, MA 01890
    60 Lake St Unit D, Winchester, MA 01890
    60 Lake St Unit D, 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
  • 63 Holland St Unit 63, Winchester, MA 01890
    63 Holland St Unit 63, Winchester, MA 01890
    63 Holland St Unit 63, 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

    Agent Photo

    Issam Dib

    Skyline Realty

    63 Holland St Unit 63, Winchester, MA 01890
  • 16 Nathaniel Rd, Winchester, MA 01890
    16 Nathaniel Rd, Winchester, MA 01890
    16 Nathaniel Rd, Winchester, MA 01890
    /9

    $4,400 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
  • 488 Washington St, Winchester, MA 01890
    488 Washington St, Winchester, MA 01890
    488 Washington St, Winchester, MA 01890
    /20

    $4,495 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
  • 17 Russell Rd, Winchester, MA 01890
    17 Russell Rd, Winchester, MA 01890
    17 Russell Rd, Winchester, MA 01890
    /15

    $4,800 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,657 Sq Ft
    • House for Rent

    17 Russell Rd, Winchester, MA 01890

    Move in date: Now. Tenant pays all utilities (gas, heat, electricity, cold/hot water and trash disposal). Lead Paint: Certified Treated. 2 off street parking. Central AC ,Pets negotiable. Laundry in the unit. 12-month lease minimum Move-in costs: First month's rent, one month's rent as a security deposit, Last month rent Welcome to 17 Russell Road, a well-maintained single-family home tucked away

    KoKo Kwan Kwan Realty Inc.

    17 Russell Rd, Winchester, MA 01890

Showing Results 1 - 40, Page 1 of 2

Massachusetts Middlesex County

Newest Homes for Rent in Winchester, MA

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 $4,447 per month, though prices vary by neighborhood, size, and property type. As of August 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 $177,880 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 $4,447 per month in Winchester, MA, renters typically need to show $13,341 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 31.8, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.
What neighborhoods in Winchester, MA are best for renting a 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, West Medford and Arlington Heights, each with its own character and price range.

Rental Trends in Winchester, MA

There are currently 45 homes available for rent in Winchester, MA. The median rent is $4,447 per month, with single-family homes renting at $5,700, townhouses at $6,000 and condos at $2,875.

Rental Home Trends

Number of Homes for Rent
45
Median Rent
$4,447
Median Single Family Home Rent
$5,700
Median Townhouse Rent
$6,000
Median Condo Rent
$2,875
How to Rent a Home

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