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Apartments for Rent in Winchester, MA

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Cutter Village - Photo 1 of 1

2d ago

9

Excellent

Cutter Village

778 Main St, Winchester, MA 01890

In-unit laundry | Air conditioning | On-site laundry

2 beds

1 bath

$2,999

The price shown reflects a 12-month lease. Fees may apply.

Apartment for rent

Inviting Home with Easy Commuting & Modern Comforts

Residents of Cutter Village enjoy a fantastic third-floor living space featuring hardwood floors and a cozy gas fireplace. This pet-friendly unit includes in-unit washer/dryer hookups, an elevator for convenience, and off-street parking options. Walking distance to the commuter rail station and local shopping enhances the appeal, making it easy to explore Winchester Town Center and beyond. Fresh paint and recessed lighting await in this inviting home!

6365 Harvard St #2 - Photo 1 of 1

5d+ ago

Winchester Highlands apartment for rent in Winchester

CONDO - Winchester, MA

6365 Harvard St #2, Winchester, MA 01890

Garage parking | On-site laundry | Outdoor space

3 beds

2 baths

$3,300

$3,200

Price drop

The price shown reflects a 12-month lease. Fees may apply.

Apartment for rent

3-bed Winchester condo with garage and office

Quietly set in Winchester Highlands, this 3-bed, 2-bath condo spans two floors with 1,200 sqft of living space. The main level features an open kitchen with pantry, spacious living room, and two bedrooms, while upstairs adds two more rooms including a dedicated office. Garage parking, shared backyard, and basement laundry complete the unit in the Muraco School District.

270 Cross St #NA - Photo 1 of 1

5d+ ago

Winchester Town Center house for rent in Winchester

Winchester Gorgeous SF Home w/ Garage 4 Prkng, Big Deck, Yard

270 Cross St #NA, Winchester, MA 01890

In-unit laundry | Garage parking | Assigned parking

4 beds

4 baths

$6,000

The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.

House for rent

Available Sep 1

Expansive Renovated Home with Versatile Spaces

This stunning 4-bedroom, 4-bathroom home offers three levels of living space, ideal for remote work or family life. Enjoy modern finishes throughout, including a chef’s kitchen with quartz countertops and stainless steel appliances. The basement features a walkout suite perfect for guests or in-laws. A large private backyard and deck are perfect for entertaining. Located in the desirable Lynch School District and walking distance to parks and amenities, this home is the perfect blend of comfort and convenience.

161 Highland Ave #NA - Photo 1 of 1

5d+ ago

Winchester Highlands house for rent in Winchester

$8,500 - 6 Bedroom 2.5 Bathroom House In Winchester With Great Amenities

161 Highland Ave #NA, Winchester, MA 01890

In-unit laundry | Air conditioning | Balcony

6 beds

2.5 baths

$8,500

The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.

House for rent

Available Aug 1

171 Swanton St #77 - Photo 1 of 1

5d+ ago

Winchester Town Center townhouse for rent in Winchester

Renovated 3 bed 2.5 bath townhome in the heart of Winchester

171 Swanton St #77, Winchester, MA 01890

In-unit laundry | Air conditioning | Garage parking

3 beds

2.5 baths

$4,550

The price shown reflects a 12-month lease. Fees may apply.

House for rent

Available Jul 1

3-bed townhouse with garage and commuter rail

This 1,826 square-foot townhouse in Winchester Town Center includes 3-bed, 2.5-bath layout with updated kitchen, stainless appliances, and in-unit laundry. The private driveway fits 2 cars plus a 1-car garage, while the landscaped patio opens to a large yard. Community pool and tennis court add recreation, with Winchester commuter rail just a mile away.

Cross St #B - Photo 1 of 1

5d+ ago

Winchester Highlands apartment for rent in Winchester

Cross St #B, Winchester, MA 01890

In-unit laundry | On-site laundry | Walk-in closets

2 beds

1 bath

$2,300

The price shown reflects a 12-month lease. Fees may apply.

Apartment for rent

Available Aug 1

2-bed Winchester apartment with deck & laundry

This 2-bed, 1-bath apartment in Winchester Highlands features in-unit laundry, high ceilings, and a private deck. Central air, walk-in closet, and ceramic tile flooring complement the sunny layout, while building amenities include a roof deck and storage space.

Nearby rental good for wellness

Nearby rental good for wfh

200 Swanton St - Photo 1 of 1

5d+ ago

Winchester Town Center condo for rent in Winchester

Furnished | Air conditioning | On-site laundry

1 bed

1 bath

$2,250

The price shown reflects a 12-month lease. Fees may apply.

Condo for rent

1-bed Winchester condo with utilities included

Located in Winchester Town Center, this 1-bed, 1-bath condo at Parkview Condominiums offers scenic views and an open layout with generous natural light. The 613 sqft partially furnished unit includes heat, hot water, AC, and electric in rent. Building amenities feature an in-ground pool, elevator, on-site laundry, and assigned parking, with easy access to Winchester Center shopping and commuter routes.

43 Harvard St - Photo 1 of 1

5d+ ago

Winchester Highlands apartment for rent in Winchester

1 bed

1 bath

$2,400

The price shown reflects a 12-month lease. Fees may apply.

Apartment for rent

Remodeled 1-bed Winchester apartment with parking

1-bed apartment in Winchester Highlands, completely remodeled 5 years ago with hardwood floors throughout and a stained glass window highlighting original details. The 825 sqft first-floor unit includes off-street parking and sits close to Winchester center with a top-rated elementary school just 0.09 miles away.

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Residences @ Malden Station - Photo 1 of 1
Highly rated

1d ago

9.6

Excellent

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Residences @ Malden Station

138 Pleasant St, Malden, MA 02148

In-unit laundry | Garage parking | Balcony

Studio–2 beds

1–2 baths

$3,011–$4,580

The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.

Apartment for rent

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Heritage at Stone Ridge - Photo 1 of 1
Highly rated
3D tour

1d ago

9.9

Excellent

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Heritage at Stone Ridge

2 Littles Brook Ct, Burlington, MA 01803

In-unit laundry | Air conditioning | Garage parking

1–2 beds

1–2 baths

$2,595–$4,110

Price drop

The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.

Apartment for rent

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74 Sharon St #1 - Photo 1 of 1

5d+ ago

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Personal bedroom in immense renovated house and

74 Sharon St #1, Medford, MA 02155

In-unit laundry | Balcony | Hardwood floor

1 bed

3 baths

$1,050

The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.

House for rent

Available Jul 1

2d ago

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167 Summer St #2, Arlington, MA 02474

Air conditioning | Hardwood floor | Dishwasher

5 beds

2 baths

$5,000

The price shown reflects a 12-month lease. Fees may apply.

Apartment for rent

Available Sep 1

2d ago

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167 Summer St #1, Arlington, MA 02474

In-unit laundry | Air conditioning | Hardwood floor

4 beds

2.5 baths

$5,500

The price shown reflects a 12-month lease. Fees may apply.

Apartment for rent

Available Jul 31

286 Salem St - Photo 1 of 1

5d+ ago

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Beautiful Townhouse style 2 BR on two floors * Close Medford Sq, I-93

286 Salem St, Medford, MA 02155

Deck | Dishwasher

1 bed

1 bath

$2,400

The price shown reflects a 12-month lease. Fees may apply.

Apartment for rent

Available Sep 1

53 Oakland St #2 - Photo 1 of 1

1d ago

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Medford Sq 3 Bedroom - 2 BATHS!!! Huge!

53 Oakland St #2, Medford, MA 02155

In-unit laundry | On-site laundry | Dishwasher

3 beds

2 baths

$4,000

$3,600

Price drop

The price shown reflects a 12-month lease. Fees may apply.

Apartment for rent

Available Sep 1

2500 Mystic Valley Pkwy #805 - Photo 1 of 1

5d+ ago

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8th floor condo in Elevator Building * Parking * AC * Porch * Pool

2500 Mystic Valley Pkwy #805, Medford, MA 02155

In-unit laundry | Air conditioning | Assigned parking

2 beds

2 baths

$3,200

The price shown reflects a 12-month lease. Fees may apply.

Condo for rent

Available Aug 15

Find sweet deals near Winchester

These rentals are 10%-30% cheaper than the local average price for similar rentals.

28 Park Ave - Photo 1 of 1

5d+ ago

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Awesome Single Family Home * Medford * No fee! Parking! Pets!

28 Park Ave, Medford, MA 02155

In-unit laundry | Air conditioning | Garage parking

3 beds

3.5 baths

$5,900

$5,700

Price drop

The price shown reflects a 12-month lease. Fees may apply.

Apartment for rent

Available Sep 1

308 Spring Street Ext - Photo 1 of 1

5d+ ago

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Medford 3+/4 Bedroom - Parking - Renovated Kitchen

308 Spring Street Ext, Medford, MA 02155

Hardwood floor | Dishwasher | Outdoor space

3 beds

1 bath

$3,200

The price shown reflects a 12-month lease. Fees may apply.

Apartment for rent

Available Aug 1

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126 Auburn St #1 - Photo 1 of 1

5d+ ago

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Medford 3 Bedroom

126 Auburn St #1, Medford, MA 02155

In-unit laundry | On-site laundry | Dishwasher

3 beds

1 bath

$3,900

The price shown reflects a 12-month lease. Fees may apply.

Apartment for rent

Available Aug 1

32 Walnut St - Photo 1 of 1

5d+ ago

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Renovated * DW * Granite * Tandem parking * Porch *

32 Walnut St, Arlington, MA 02476

On-site laundry | Dishwasher

2 beds

1 bath

$2,950

The price shown reflects a 12-month lease. Fees may apply.

Apartment for rent

Available Jun 15

30 Mill St - Photo 1 of 1

5d+ ago

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30 Mill St, Arlington, MA 02476

In-unit laundry | Air conditioning | Garage parking

1 bed

1 bath

$2,381

The price shown reflects a 12-month lease. Fees may apply.

Apartment for rent

Available Mar 5

Average rent

The average rent in Winchester, as of August 2026, is up 18.63% compared to last month and up 15.96% year-over-year.
$3,577
increased by16%

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3 Chapel Way - Photo 1 of 1

5d+ ago

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3 Chapel Way, Stoneham, MA 02180

Furnished | Air conditioning | Garage parking

5 beds

3 baths

$9,470

$8,332

Price drop

The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.

Apartment for rent

92 Sylvia St - Photo 1 of 1

5d+ ago

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Arlington Heights 3 Bed - Parking Included

92 Sylvia St, Arlington, MA 02476

On-site laundry | Hardwood floor | Dishwasher

3 beds

1 bath

$3,000

The price shown reflects a 12-month lease. Fees may apply.

Apartment for rent

Available Apr 5

Showing 1 - 25 of 25 results
Home > Apartments in Winchester
Updated: August 3, 2026

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Learn more about renting in Winchester, MA

Local insights: What it's like to live in Winchester, MA

Winchester offers a blend of suburban tranquility and easy access to urban amenities, which residents appreciate. Many enjoy the picturesque neighborhoods and well-maintained parks, making it ideal for families. The local schools receive high marks, adding to the appeal for those with children. However, some residents express concerns about the high cost of living and limited entertainment options, suggesting that when it comes to dining and nightlife, the options can feel somewhat lacking. Overall, life in Winchester is characterized by its residential feel and accessibility to Boston.

What are the best neighborhoods to rent an apartment in Winchester, MA?

Winchester Town Center and Winchester Highlands stand out as the city's premier rental neighborhoods, offering strong community appeal with high walk scores and excellent transit access. Winchester Town Center dominates the market with 80% of the city's rental inventory and draws nearly 86% of consumer interest.

What areas of Winchester, MA are best for budget-conscious renters?

Based on our current listings data, Winchester Town Center has a median rent of around $2,730, representing the primary rental option in the city with 80% of available inventory.

Are there pet-friendly apartments in Winchester, MA?

Winchester Town Center and Winchester Highlands are exceptionally pet-friendly, featuring apartments with pet-safe windows, dedicated pet spaces, and outdoor areas for daily walks. Many properties offer on-site pet grooming services, maintain no breed restrictions, and host regular pet events to build community among animal lovers.

Are utilities usually included in rent in Winchester, MA?

Based on our current listings, utilities-included rentals are extremely rare in Winchester, appearing in only 0.05% of available apartments across all bedroom types.

Are most apartments in Winchester, MA largely older buildings or new developments?

Based on our current listings data, Winchester apartments blend classic and modern features, with 65% offering hardwood floors while many properties incorporate sustainable construction materials and contemporary amenities like rainwater harvesting systems.

Methodology: How we got this data

Zumper’s proprietary rental data fuels our analysis. Rent and market trends, availability, neighborhood popularity, and lifestyle scores are all calculated using real-time and 2026 rental inventory and prices.

Our Lifestyle Categories ("great for eco-living," "great for social life," "great for pet owners," etc.) are determined by set criteria, against which we score each listing and its available features. At the neighborhood level, we calculate the listing count for each category to determine which lifestyles best fit each area.

Zumper, founded in 2012, is North America’s largest privately-owned rental platform, offering over 1 million listings across the U.S. and Canada. Stay informed on the latest trends and shifts in the rental market with our monthly National Rent Report, your go-to resource for key insights into the evolving rental landscape.

Looking for apartments in Winchester, MA near you?

🔑Available apartment rentals25
💰Best rent deal74 Sharon St #1
Popular amenities, ,
🧦In-unit laundry
🍽With dishwasher
🏠With photos