Pet Friendly Homes for Rent in Winchester, MA (146 Rentals)

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Homes for rent in Winchester that love your dogs or cats as much as you do!

property at 10 Farrow St

10 Farrow St

WinchesterMA01890
property at 40 Brattle St

40 Brattle St

ArlingtonMA02476
property at 22 James St

22 James St

WoburnMA01801

Explore Like a Local: The Insider's Guide to Boston

Explore Boston like a local with our guide to neighborhoods, history, and hidden gems. Discover the city's best apartments, from historic brownstones to modern high-rises, and find your perfect Boston home.

property at 86 Orchard St

86 Orchard St, Unit #1

86 Orchard St
MedfordMA02155
property at 993 Massachusetts Ave

993 Massachusetts Ave, Unit 212

993 Massachusetts Ave
ArlingtonMA02476
property at 1 Watermill Pl

1 Watermill Pl, Unit 1 Watermill Place

1 Watermill Pl
ArlingtonMA02476
property at 995 Massachusetts Ave

995 Massachusetts Ave, Unit 403

995 Massachusetts Ave
ArlingtonMA02476
property at 995 Massachusetts Ave

995 Massachusetts Ave, Unit 403

995 Massachusetts Ave
ArlingtonMA02476
property at 37 Westminster Ave

37 Westminster Ave, Unit 2

37 Westminster Ave
ArlingtonMA02474
property at 19 Newland Rd

19 Newland Rd, Unit 2

19 Newland Rd
ArlingtonMA02474
property at 104 Forest St

104 Forest St, Unit 104

104 Forest St
ArlingtonMA02474

The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

property at 132 Broadway

132 Broadway, Unit 1

132 Broadway
ArlingtonMA02474
property at 116 Medford St

116 Medford St, Unit 1

116 Medford St
ArlingtonMA02474
property at 47 Webster St

47 Webster St, Unit 47

47 Webster St
ArlingtonMA02474
property at 40 Campbell St

40 Campbell St

WoburnMA01801
property at 10 Harvard Street Ext
property at 2012 Symmes Cir

2012 Symmes Cir, Unit 1

2012 Symmes Cir
ArlingtonMA02474
property at 33 Rublee St

33 Rublee St

ArlingtonMA02476
property at 13 Garfield Ave

13 Garfield Ave

WoburnMA01801
property at 133 Park Ave

133 Park Ave

ArlingtonMA02476
property at 271 Ridge St

271 Ridge St

ArlingtonMA02474

Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

property at 35 Bowdoin St

35 Bowdoin St, Unit 35

35 Bowdoin St
ArlingtonMA02474
property at 422 High St

422 High St, Unit 10

422 High St
MedfordMA02155
property at 14 Cotting St

14 Cotting St, Unit 3

14 Cotting St
MedfordMA02155
property at 9 Circuit St

9 Circuit St, Unit 1

9 Circuit St
MedfordMA02155
property at 17 Usher Rd

17 Usher Rd, Unit 3

17 Usher Rd
MedfordMA02155
property at 40 Hamilton St

40 Hamilton St, Unit 1

40 Hamilton St
MedfordMA02155
property at 26 Bradlee Rd

26 Bradlee Rd, Unit 1

26 Bradlee Rd
MedfordMA02155
property at 260 Boston Ave

260 Boston Ave, Unit 1

260 Boston Ave
MedfordMA02155
property at 258 Boston Ave

258 Boston Ave, Unit 3

258 Boston Ave
MedfordMA02155
property at 23 Curtis St

23 Curtis St

MedfordMA02155

The Art of the Rental Viewing: What to look for during a property tour

Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

property at 227 Boston Ave

227 Boston Ave, Unit 1

227 Boston Ave
MedfordMA02155
property at 165 Sharon St

165 Sharon St

MedfordMA02155
property at 21 Jerome St

21 Jerome St

MedfordMA02155
property at 5 Harris Rd

5 Harris Rd, Unit 1

5 Harris Rd
MedfordMA02155
property at 293 Boston Ave

293 Boston Ave, Unit 2

293 Boston Ave
MedfordMA02155
property at 119 Burget Ave

119 Burget Ave, Unit 2

119 Burget Ave
MedfordMA02155
property at 119 Burget Ave

119 Burget Ave, Unit 2

119 Burget Ave
MedfordMA02155
property at 20 Bellevue St

20 Bellevue St

MedfordMA02155
property at 5 Harris Rd

5 Harris Rd

MedfordMA02155
property at 69 Arlington St

69 Arlington St

MedfordMA02155
property at 10 Greenleaf Ave

10 Greenleaf Ave, Unit 1

10 Greenleaf Ave
MedfordMA02155
property at 217 Arlington St

217 Arlington St

MedfordMA02155

Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

property at 480 Fulton St

480 Fulton St, Unit 478

480 Fulton St
MedfordMA02155

Winchester, MA Local Guide

Quick Rent Budget Calculator

How much rent can you afford?

The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.

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Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Winchester, MA Rentals by Map

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Frequently Asked Questions about Winchester

What type of rentals are currently available in Winchester?

There are currently 636 Apartments for Rent in Winchester, MA with pricing that ranges from $1,550 to $9,300. There are also 405 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,200 to $40,000.

What is the current price range for Rental Homes in Winchester?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Winchester ranges from $1,200 to $40,000 with an average monthly rent of $4,804.

How much are larger Three and Four Bedroom Rentals in Winchester?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Winchester range from $2,250 to $7,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,850 to $20,000. Four Bedroom Single-Family rentals are also available starting from $3,425 and Four Bedroom Apartments start at $3,200.

Expert Rental Resources

Helpful Apartment Articles, How-To's and Tips

The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.

decorative image for The 10 Best Affordable Neighborhoods in Boston, MA article

The 10 Best Affordable Neighborhoods in Boston, MA

Written by: Amelia Ramstead

Boston is known for its exciting combination of early American history and modern high-tech universities and employers.

decorative image for The Rental Move-In Inspection Checklist: A Guide for Renters article

The Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.

decorative image for Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between article

Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Written by: Christine Leonard, Esq.

For many people, obstacles can arise during the rental application process for a variety of issues.

decorative image for The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro article

The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Written by: Christine Leonard, Esq.

Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.