2 Bedroom Apartments for Rent in Windsor, VT (65 Rentals)

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5 Acme St
2 Bedroom Apartments

5 Acme St

5 Acme StWindsor, VT 05089
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27 Maple Street
2 Bedroom Apartments

27 Maple Street

27 Maple StWindsor, VT 05089
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77 Union St
2 Bedroom Apartments

77 Union St

77 Union StWindsor, VT 05089
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Union Square
2 Bedroom Apartments

Union Square

1-17 Union StWindsor, VT 05089
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24 State Street
2 Bedroom Apartments

24 State Street

24 State StWindsor, VT 05089
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63 Main Street
2 Bedroom Apartments

63 Main Street

55 Depot AveWindsor, VT 05089

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

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

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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.

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property at 20 Wolf Rd

20 Wolf Rd

LebanonNH03766
property at 50 Doc's Dr

50 Doc's Dr

GranthamNH03753

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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.

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Abenaki Springs
2 Bedroom Apartments

Abenaki Springs

17 Avery LnWalpole, NH 03608
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35-53-79 Meadow Ln
2 Bedroom Apartments

35-53-79 Meadow Ln

35 Meadow LnCastleton, VT 05735
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38 West
2 Bedroom Apartments

38 West

38 West StFair Haven, VT 05743

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.

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Showing Results 1-50, Page 1 of 2

Windsor, VT Local Guide

Largest Available Windsor and Nearby 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Windsor, VT is found at Timberwood Commons and is 1,006 square feet priced from $2,809. 58 Sullivan Street has the second largest 2 Bedroom, which is sized at 1,000 square feet and currently listed start at $1,750. Here is today’s list of the largest available 2 Bedroom units in Windsor:

Apartment ListingModel NameSquare FootagePriced From
Timberwood CommonsPine1,006 Sq Ft$2,809
58 Sullivan Street1 x 11,000 Sq Ft$1,750
Woolen Mills2BA1BR925 Sq Ft$1,243
Stone FarmPine875 Sq Ft$2,495
Oak Creek ApartmentsOak Creek 2 Bedroom850 Sq Ft$1,675
The Pines Apartments2 Bedrooms, 1 Bathroom771 Sq Ft$1,534
Maple Leaf Apartments2 Bedroom750 Sq Ft$1,475
Colony Mill2 Bed 1 Bath749 Sq Ft$2,155
333 Giddings St2 bed/1 bath700 Sq Ft$1,400
16 Union St2 Beds, 1 bath600 Sq Ft$1,450

Cheapest Available Windsor and Nearby 2 Bedroom Apartments

As of September 09, 2025 the lowest priced 2 Bedroom apartment unit in Windsor, VT is the 2 Beds, 1 bath Model starting from $1,069 at Gile Hill Rental Community . The second most affordable Windsor 2 Bedroom is the 2BA1BR Model at Woolen Mills starting at $1,243 . The average price for all 2 Bedroom apartments in Windsor is currently $2,276. Here is today’s list of the cheapest available 2 Bedroom options in Windsor:

Apartment ListingModel NamePriced From
Gile Hill Rental Community2 Beds, 1 bath$1,069
Woolen Mills2BA1BR$1,243
333 Giddings St2bed/bath$1,400
17 Sullivan St2BR/1.0BA$1,422
16 Union St2 Beds, 1 bath$1,450
Maple Leaf Apartments2 Bedroom$1,475
The Pines Apartments2 Bedrooms, 1 Bathroom$1,534
Oak Creek ApartmentsOak Creek 2 Bedroom$1,675
241 S Main St2 Bedroom$1,700
58 Sullivan Street1 x 1$1,750

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

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Getting Around Windsor, VT

Walk Score®

42 / 100

Car-Dependent

Most errands require a car

Bike Score®

28 / 100

Somewhat Bikeable

Minimal bike infrastructure

What Are Walk Score®, Transit Score®, and Bike Score® Ratings?

  • Walk Score® measures the walkability of any address.
  • Transit Score® measures access to public transit.
  • Bike Score® measures the bikeability of any address.

Frequently Asked Questions about 2 Bedroom Windsor Apartments

What is the Cheapest apartment in Windsor with 2 Bedroom?

Currently the most affordable 2 Bedroom in Windsor is at Gile Hill Rental Community listed at $1,069.

How much is the average rent for a 2 Bedroom Windsor Apartment?

The average rent for a 2 Bedroom Apartment in Windsor is $2,276.

What is the largest available 2 Bedroom Windsor Apartment for rent?

Today's apartment with the most square footage in Windsor is a 1,006 square feet unit starting from $2,809 at Timberwood Commons.

What is the average size for Windsor 2 Bedroom Apartments for rent?

The average size for a 2 Bedroom rental in Windsor is currently 1,159 sq ft.

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.

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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.

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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.

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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.

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

Written by: Christine Leonard, Esq.

Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.