Chester Homes under $500,000

Welcome to Chester, a vibrant city steeped in history and charm, located in the heart of Cheshire, England. Known for its stunning medieval architecture, picturesque streets, and the iconic Chester Cathedral, this city offers a unique blend of the old and the new. With its rich heritage, Chester is a place where you can explore ancient Roman ruins, stroll along the beautiful River Dee, and enjoy the bustling atmosphere of its renowned shopping districts and delightful eateries.

For those looking to make Chester their home, there is an exciting range of properties available, particularly under $500,000. This price range offers a fantastic opportunity to invest in a variety of homes, from quaint cottages nestled in the city’s historic quarters to modern family houses in welcoming neighborhoods. Whether you're a first-time buyer, a growing family, or looking to downsize, Chester’s real estate market has something to suit every taste and lifestyle.

Imagine living in a charming Victorian terrace just a stone's throw from the city center, or perhaps a contemporary apartment with stunning views of the picturesque Chester cityscape. With excellent schools, parks, and a strong sense of community, Chester is an ideal place to set down roots.

Explore the possibilities of finding your dream home in this enchanting city, where history meets modern living, and every day feels like a new adventure. With homes under $500,000, Chester is not just a place to live; it's a place to thrive. Come and discover the charm of Chester for yourself!

Newest Chester Homes under $500,000

$39,000

73586614 MLS

Unique Property with Multiple Outbuildings and Versatile Use Potential Discover a rare opportunity in Chester — a property offering multiple outbuildings, upgraded utilities, and flexible space for storage, recreation, or future development.The land includes two well-built sheds:Utility Shed — insulated, equipped with electric heat, and houses the well pump, providing reliable year-round functionality. Cabin-Style Shed — transformed into a comfortable retreat with 200-amp electrical service, electric heat, and full insulation, making it ideal as a workshop or hobby space.A metal shipping container on the property adds substantial secure storage for equipment, tools, or recreational gear. Whether you’re looking for a getaway spot, a base for outdoor activities, or a property with ready-made utility structures, this location offers exceptional versatility.

2 Taft Rd, Chester

$229,000

2 Beds ⋅ 1 Baths ⋅ 5112828 MLS

Sometimes, just the right amount of space is exactly what you need. Set on two pleasant acres in Chester, this tidy 2-bedroom, ¾-bath home offers comfortable, efficient one-level living with a practical layout that makes everyday life easy. Inside, the home is bright and well cared for, with a modern kitchen, comfortable living space, two nicely sized bedrooms, laundry, and the convenience of everything on one floor. Propane heat keeps things simple and efficient, while the manageable footprint means less house to maintain and more time to enjoy Vermont. Outside, the level lawn provides plenty of usable space for gardening, pets, a fire pit, or simply relaxing outdoors without taking on an overwhelming property. A detached two-car garage offers excellent parking, storage, and room for the tools and gear that come with Vermont living. Whether you're looking for a first home, ready to simplify, or searching for a comfortable retirement property with minimal stairs and manageable upkeep, this Chester home checks a lot of boxes. Simple, practical, and easy to maintain, it is a home that makes perfect sense.

547 Andover Rd, Chester

$189,000

2 Beds ⋅ 1 Baths ⋅ 73585530 MLS

First Showings start Sunday 10/4 at the Open House, 11am-12:30pm on this great starter home. If you have been looking for an affordable opportunity to buy a home, then this is it. The home has an open layout with a large living room, dining room and a full bath all on the first level. There is also a sizable country kitchen that leads to a deck with a pleasant view of the hills of Chester. There is a laundry off the kitchen as well. The second floor has another bedroom and an open area that is presently used as a guest/bed loft. Off the back deck is a yard with enough room for the kids or entertaining. There is also a barn shed on the property for workshop or storage. This home is the perfect starter home on a quiet dead end street and walking distance to all Chester has to offer.

1 William St, Chester

$433,900

2 Beds ⋅ 2 Baths ⋅ 5112444 MLS

At The Villages at Chester, a private townhouse community, you come home to quiet private roads and a wooded recreation area, and the Association takes care of it all right down to the home’s exterior and even plowing your driveway and shoveling your walkway. Walk the wooded trails, spend summer at the pool, and book the clubhouse for your party. This end-unit townhouse has three finished levels, with hardwood throughout the first and second floors. The living room centers on a gas fireplace with a stacked-stone surround, prewired for a TV above. The dining room has a built-in corner cabinet and a slider out to a deck that runs the full width of the house, and nearly every window has a wooded view. The kitchen has knotty wood cabinets with a built-in wine rack, granite, stainless appliances, a five-burner gas stove and a peninsula with seating. The attached garage opens into a mudroom with a half bath and first-floor laundry. Upstairs, the large primary bedroom runs nearly the full depth of the house, with a vaulted ceiling, a skylight and a walk-in closet fitted out by California Closets with floor-to-ceiling shelving and drawers. The second bedroom is generous with two large windows, a ceiling fan and a double closet. A full bath with a double vanity connects the two, and a window seat in the hall looks out over your garden. Downstairs is the surprise. The finished lower level is carpeted and bigger than you'd expect, with a bonus room that stretches nearly the width of the house, full-size windows and a slider out to a patio and backyard. A separate room makes space for guests, or a workout area and another space ideal for an office or hobby room, and there’s the utility room and many closets for storage. Newer Andersen windows and a tankless water heater are already done. The HOA fee also covers trash, water and sewer. Pet-friendly community, and Chester keeps its small-town feel with horses and orchards nearby, and Pinkerton Academy for high school.

25 Villager Rd, Chester

$249,900

2 Beds ⋅ 1 Baths ⋅ 5110600 MLS

Enjoy the beauty and charm of Vermont with this mobile home set on approximately 1 acre in Chester. Located across the road from a peaceful river, this property offers a wonderful setting for enjoying the outdoors and the natural beauty of the area. The property features an oversized 2 car garage with plenty of room for vehicles, recreational equipment, tools, and hobbies. Above the garage is finished bonus space, offering flexibility for a home office, studio, recreation room, guest area, or additional storage. This lot provides room to enjoy the outdoors, garden, entertain, or simply relax and take in the surrounding Vermont scenery. With the river just across the road, the property offers a special location for those looking to enjoy the tranquility and character of Chester. Come see what makes this Chester property special!

3537 Popple Dungeon Rd, Chester

$129,900

1 Baths ⋅ 73579781 MLS

Escape to the scenic hills of Chester with this unique 5.2-acre property offering the opportunity to create your year-round country home. Two major infrastructure investments are already in place with the well and three bedroom septic system. Giving you the head start on your new home. The existing 560-square-foot cottage provides a comfortable retreat while you plan and develop your vision for the property. Surrounded by wooded acreage, the setting offers privacy, natural beauty, and plenty of room to enjoy the outdoors. In the meantime, the existing cottage makes an excellent weekend getaway, hunting lodge, or recreational retreat. Built in 2011 with a metal roof, wood exterior, the cottage provides a solid starting point. A special opportunity to build a year-round home in a peaceful Western Massachusetts setting while enjoying the property today. Buyer to perform all due diligence regarding zoning, permitting, building requirements, and future use.

93 Crane Rd, Chester

$489,000

3 Beds ⋅ 1 Baths ⋅ 5107622 MLS

Wait until you see this charming, light and bright one-level Ranch with direct access to the Exeter River! Enjoy fishing or launching a canoe right from your own backyard, all while being located outside of a flood zone. Tucked away on a private lot in Chester with no neighbors visible on either side, this home offers a peaceful setting surrounded by nature. Inside, you’ll find a light-filled and inviting interior, 2–3 bedrooms, an updated kitchen, a full bathroom, and a basement offering plenty of storage. A cozy wood stove will keep you toasty during those chilly New Hampshire winters. Step outside onto the spacious deck overlooking the river, the perfect place to relax, entertain, or simply take in the beautiful natural surroundings. Outdoor enthusiasts will love the abundant birds and wildlife, fishing, and opportunities for canoeing or boating when water levels allow. A storage shed, additional she-shed, and extra parking add even more versatility. If you’ve been dreaming of a light, bright and peaceful home where you can enjoy the outdoors right from your own backyard, this one is a must-see! Quick close possible!

56 Shepard Home Rd, Chester

$255,000

3 Beds ⋅ 2 Baths ⋅ 5106226 MLS

Welcome to 159 Lower Bartonsville Road, a charming carriage house nestled along a scenic country farm road in Rockingham, Vermont, just moments from the picturesque restored Bartonsville covered bridge. This 3 bed, 1.5 bath property features authentic 1830s architecture and timeless rustic character, offering a solid structural foundation with much of its original detail preserved. Seamlessly blending old-world appeal with boundless equity-building potential, this quintessential New England abode serves as the perfect canvas for your personal touch. It is entirely ready for cosmetic enhancements, custom modern finishes, and tailored design choices that will allow you to completely personalize the space to match your unique vision. Just 15 minutes from I-91 and Springfield VT, 35 minutes to Keene, NH and 40 minutes to Lebanon NH. Stop on by and see it for yourself!

159 Lower Bartonsville Rd, Chester

$289,900

3 Beds ⋅ 3 Baths ⋅ 5106191 MLS

Extremely well maintained and thoughtfully updated, this spacious three bedroom, two and a half bath home is privately nestled on 2.6 acres on a quiet dead end. Offering the convenience of single level living, the property has been meticulously cared for over the years, with numerous improvements that make it comfortable, efficient, and move in ready. Inside you’ll find generously sized rooms throughout, offering plenty of space for everyday living and entertaining. The home features a primary suite with its own private full bathroom with a soaking tub, two additional good sized bedrooms, another full bath, and a convenient half bath. The functional single level layout makes the home easy to enjoy, while the main living areas offer plenty of natural light and comfortable gathering space. The home has seen an impressive list of recent updates, including new kitchen flooring in 2021, a new roof and skylights in 2022, newer kitchen appliances, and a mini-split system installed in 2023. Additionally, a new hot water heater in 2025. Set on 2.6 acres, the property offers a peaceful and private setting while still providing convenient access to Chester and the surrounding area. With its spacious rooms, primary suite, 2.5 baths, single level living, extensive recent improvements, and exceptionally well-maintained condition, this is a home that has been cared for with attention to detail and is ready for its next owners to enjoy.

3713 Trebo Rd, Chester

$225,000

2 Beds ⋅ 1 Baths ⋅ 73563768 MLS

Welcome home to your little slice of a rural countryside community. This property is situated on the west branch of the Westfield River in a quiet but convenient location. Enjoy your coffee on the porch and get lost in the sounds of nature. Inside you will find an open floor plan, a newer primary first floor bedroom, and three rooms upstairs with closets. This home is a hidden gem with tons of potential. Book your showing and bring your vision. Water heater purchased in 2021. Roof on addition was put on this year APO. Roof on main part of house is about 12 years old. 500 gal propane tank is owned. Buyer to do due diligence. Sale is contingent on resolving prior contract. Property appraised for 239k.

23 Maple St, Chester

$100,000

2 Beds ⋅ 2 Baths ⋅ 73561688 MLS

Investors take note of the potential offered by this charming colonial home. Property is being sold as-is. The seller prefers a 60-day closing to allow sufficient time for removal of personal items from the house, yard, and barn. Title V has failed and will be the buyer’s responsibility. The home features partially updated plumbing and electrical systems, including an electrical panel and hot water tank installed approximately three years ago.

166 Route 20, Chester

$330,000

2 Beds ⋅ 1 Baths ⋅ 5102316 MLS

If you're looking for your forever home or the perfect mountain getaway, take a peek at this locally built Green Mountain Log Home. Davidson Hill Road is home to many craftsman quality homes perched above Chester, overlooking Mt. Ascutney. The open concept first floor spills out onto the generous front deck, essentially doubling the first floor area to roam. Two nearly identical wooden clad bedrooms make up the second floor. The home has a new roof, new on-demand hot water system, fresh stain on the log exterior, updated electrical, brand new LVL carrying beam and floor joists, new interior trap door basement access and stairs, and new laundry station in the basement. Many other practical upgrades and extensive landscaping has been made and this home is in mint condition. The sellers recently did a drinking water test, had the septic pumped, and did a home inspection, leaving no stone unturned. The 11 acre parcel transitions from a large sunny open yard to old stone walls and hemlock-hardwood forest and rises nearly to the humble summit of Davidson Hill (1053' elevation). The owners let a neighboring property tap most of the maple trees in exchange for maple syrup. The house is located just feet from Trail #5 of the Hawks Mountain Ridge Riders VAST trail network, and is minutes from downtown Springfield and Chester. Just 15 minutes from I-91 and Okemo. While surrounded by forest and situated for optimum privacy, this home does have seasonal views of Mt. Ascutney and there is a good possibility of spectacular views higher up on the property. The height of the property would make an awesome camping or gazebo spot. Many logging roads and four wheeler trails throughout the property. The dog on the couch does not convey.

302 Davidson Hill Rd, Chester

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