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Pet-Friendly Homes for Rent in Winchester, MA

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    $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
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    $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
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    $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
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    $3,700 Per Month

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

    303 Washington St Unit 1, Winchester, MA 01890

    Flexible lease terms! 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 unit has always been owner occupied and is in meticulous condition .. featuring generously sized rooms with high ceilings, oversized windows, hardwood floors, beautiful original woodwork, crown

    Kim Covino Compass

    303 Washington St Unit 1, Winchester, MA 01890
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    $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
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    $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
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    $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
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    $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
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    $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
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    $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 The Archambault Group

    52 N Border Rd, Winchester, MA 01890
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    $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
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    $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
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    $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
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    $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
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    $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
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    $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
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    $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
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    $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

Rental Home Trends

Number of Homes for Rent
18
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