2 Bedroom Apartments for Rent in Winchester, NH (55 Rentals)

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130 Main St
2 Bedroom Apartments

130 Main St

130 Main StWinchester, NH 03470
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77 Richmond Rd
2 Bedroom Apartments

77 Richmond Rd

77 Richmond RdWinchester, NH 03470
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2-20 Keen Rd
2 Bedroom Apartments

2-20 Keen Rd

2-20 Keen RdWinchester, NH 03470
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11 Ashuelot St
2 Bedroom Apartments

11 Ashuelot St

11 Ashuelot StWinchester, NH 03470

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 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.

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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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Navigating the Rental Market: Tips for First-Time Renters

Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

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property at 26 Elm St

26 Elm St

KeeneNH03431
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Winchester, NH Local Guide

Largest Available Winchester and Nearby 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Winchester, NH is found at Rolling Green Apartments and is 1,158 square feet priced from $2,520. Monadnock Place in the Base Hill Coop neighborhood has the second largest 2 Bedroom, which is sized at 1,090 square feet and currently listed start at $2,720. Here is today’s list of the largest available 2 Bedroom units in Winchester:

Apartment ListingModel NameSquare FootagePriced From
Rolling Green Apartments2 Bedroom Townhouse1,158 Sq Ft$2,520
Monadnock PlaceB21,090 Sq Ft$2,720
North 116 FlatsB4 Shared910 Sq Ft$850
Sugarloaf EstatesThe Corporate850 Sq FtCall for Rates
The BouldersRenovated 2 Bedroom850 Sq Ft$1,995
11 E Pleasant StTwo Bedroom Premium810 Sq Ft$3,570
Jaffwood Apartments2 Bedroom800 Sq Ft$1,600
Meadowview ApartmentsRenovated 2 Bedroom Townhome777 Sq Ft$2,450
The Fitchburg Arts CommunityWorkforce Two Bedroom694 Sq Ft$1,934
Orchard Overlook2 Bedroom 2 Bath Corner0 Sq Ft$2,275

Cheapest Available Winchester and Nearby 2 Bedroom Apartments

As of June 27, 2025 the lowest priced 2 Bedroom apartment unit in Winchester, NH is the 2 Bedroom Model starting from $1,600 at Jaffwood Apartments . The second most affordable Winchester 2 Bedroom is the Two Bedroom Model at Lantern Court Apartments starting at $1,650 . The average price for all 2 Bedroom apartments in Winchester is currently $2,145. Here is today’s list of the cheapest available 2 Bedroom options in Winchester:

Apartment ListingModel NamePriced From
Jaffwood Apartments2 Bedroom$1,600
Lantern Court ApartmentsTwo Bedroom$1,650
Cliffside Apartments2x1$1,750
The Fitchburg Arts CommunityWorkforce Two Bedroom$1,934
The BouldersClassic 2 Bedroom$1,995
Meadowview ApartmentsRenovated 2 Bedroom$2,000
Orchard Overlook2 Bedroom 2 Bath$2,125
Rolling Green Apartments2 Bedroom$2,330
Monadnock PlaceB2$2,720
11 E Pleasant StTwo Bedroom Premium$3,570

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Getting Around Winchester, NH

Walk Score®

17 / 100

Car-Dependent

Almost all errands require a car

Bike Score®

20 / 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 Winchester Apartments

What is the Cheapest apartment in Winchester with 2 Bedroom?

Currently the most affordable 2 Bedroom in Winchester is at Jaffwood Apartments listed at $1,600.

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

The average rent for a 2 Bedroom Apartment in Winchester is $2,145.

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

Today's apartment with the most square footage in Winchester is a 1,158 square feet unit starting from $2,520 at Rolling Green Apartments.

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

The average size for a 2 Bedroom rental in Winchester is currently 1,002 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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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

Written by: Cheryl Bowman

A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.

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

Written by: Marie Brown

You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

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Know Your Budget: Calculating What You Can Realistically Afford When Renting

Written by: Lauren Harrington

Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.

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The Freedom of Short-Term Leases: Exploring the Advantages for Renters

Written by: Bobbi Jackson

If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.