Cheshire Homes under $250,000

Welcome to Cheshire, Connecticut – a charming town nestled in the heart of New Haven County, where picturesque landscapes meet a vibrant community spirit. Known for its lush parks, excellent schools, and friendly neighborhoods, Cheshire offers a perfect blend of suburban tranquility and easy access to urban amenities. With a rich history dating back to the 17th century, this town boasts a quaint New England charm that captivates residents and visitors alike.

For those seeking their dream home without breaking the bank, Cheshire presents an exciting opportunity with a selection of homes priced under $250,000. Whether you are a first-time homebuyer, a growing family, or looking to downsize, Cheshire has something for everyone. The real estate market here features a variety of options, including cozy single-family homes, charming townhouses, and well-maintained condominiums, all offering excellent value in this desirable area.

Imagine waking up in a beautiful neighborhood surrounded by tree-lined streets and friendly neighbors, all while enjoying the conveniences of local shopping, dining, and recreational activities. Cheshire is also known for its commitment to community, with numerous events and festivals throughout the year that bring residents together.

With its affordable housing options and welcoming atmosphere, Cheshire, CT, is not just a place to live – it’s a place to thrive. Discover the possibilities that await you in this delightful town, where your dream home is just around the corner, waiting to welcome you to the community!

Newest Cheshire Homes under $250,000

$199,000

2 Beds ⋅ 1 Baths ⋅ 24203224 MLS ⋅ Birchwood BLDG.

Stylish, beautifully renovated and filled with natural light, this end-unit condominium is located in the well-maintained Birchwood community, surrounded by expansive green space and ample parking. Beautiful, move in condition! The open floor plan offers two spacious bedrooms, a large living room, and a stylish white kitchen with granite countertops, self-closing cabinets with lighting and stainless steel appliances. The beautifully remodeled bathroom features modern tile, a contemporary vanity, and a glass-enclosed shower. Additional amenities include a large private storage unit and shared laundry in the basement. The HOA fee covers water, heat, hot water, management, grounds and road maintenance - truly exceptional value. With no current special assessments and strong association reserves, this home provides peace of mind and affordability. Enjoy a prime Cheshire location with access to Farmington Canal Trail just minutes from excellent restaurants and charming cafes. New Stonebridge shopping center features Whole Foods, Barnes & Noble, TJ Maxx, J. Crew and other popular retailers. This is a wonderful opportunity to own a truly beautiful home and enjoy easy, no-maintenance living in one of Connecticut's most desirable towns with very good school system.

502 Oak Ave Unit 17, Cheshire

$160,000

1 Beds ⋅ 1 Baths ⋅ 24202177 MLS ⋅ Cheshire Hillside Village BLDG.

Welcome to easy, one-level living in Cheshire Hillside Village, a desirable 62+ active adult community. The standout feature of this inviting one-bedroom condo is its large, open floor plan with generously sized rooms and a beautiful vaulted ceiling in the living room, creating a spacious, airy setting that is ideal for entertaining and everyday living. Located on the upper level, this sought-after style unit has no neighbors above, allowing for added privacy and helping create the wonderful sense of openness and natural brightness throughout. Despite being an upper-level unit, there are no stairs to enter the building, thanks to the convenient layout of the complex. Brand-new flooring throughout, fresh paint, in-unit washer and dryer and a slider that leads from the living room to the private deck with convenient exterior storage add to the appeal. The monthly HOA fee includes heat and hot water, offering added convenience and helping make monthly expenses more predictable. Ideally located in the center of Cheshire, near the Stop & Shop plaza, with easy access to I-84, I-91, and Route 691, and just a quick ride down Route 10 to the new shops at Stonebridge Crossing. Nearby recreational facilities are also easily accessible, making this a wonderful opportunity for comfortable, convenient, and low-maintenance living in the heart of Cheshire.

459 E Mitchell Ave Unit 459, Cheshire

$199,900

1 Beds ⋅ 1 Baths ⋅ 24201442 MLS ⋅ Cheshire Hillside Village BLDG.

This beautifully renovated condo features a versatile flex/bonus room and is located in a desirable 62+ community nestled within the town of Cheshire. The bright and inviting first floor unit has been completely updated from top to bottom, featuring brand-new stainless-steel appliances, tiled backsplash, crown molding, modern fixtures, new flooring, paint, a custom feature wall, and a fully refreshed kitchen and bathroom. Hardwood flooring is throughout this condo. The primary bedroom includes a well-designed closet system offering ample storage. The spacious flex room offers endless possibilities perfect for a home office, guest space, hobby room, or second bedroom. Your new sliders open to a back patio where you can relax with your morning coffee and watch the birds. The HOA includes heat and hot water, making this a truly affordable, and complete turnkey living within the town of Cheshire. There is easy parking and mailbox access. Just pack your suitcases and enjoy comfortable, low maintenance living in this well-kept community designed for active adults. Welcome home!!!

443 E Mitchell Ave Unit 443, Cheshire

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.