Chester Homes under $500,000

Welcome to Chester, a charming city that beautifully blends historic allure with modern convenience. Nestled in the heart of Cheshire, England, Chester is renowned for its stunning architecture, vibrant culture, and rich history that dates back to Roman times. With its iconic city walls, the majestic Chester Cathedral, and the picturesque River Dee, this city offers a unique living experience that captivates both residents and visitors alike.

Chester is not just a feast for the eyes; it’s also a thriving community with a lively arts scene, bustling markets, and an array of dining options that cater to every palate. Whether you’re strolling through the quaint streets lined with Tudor-style buildings or indulging in a shopping spree at the historic Rows, you’ll find that Chester has something for everyone.

For those looking to call this enchanting city home, there’s a fantastic selection of homes available for under $500,000. From charming terraced houses in the heart of the city to modern family homes in quieter neighborhoods, Chester’s real estate market offers a diverse range of options to suit various lifestyles and budgets. Many of these properties boast beautiful gardens, spacious interiors, and easy access to local amenities, making them ideal for first-time buyers, families, or anyone seeking a peaceful retreat.

Living in Chester means embracing a lifestyle rich in history while enjoying the conveniences of contemporary living. With homes under $500,000, your dream of residing in this picturesque city is more attainable than ever. Explore Chester today and discover the perfect place to create lasting memories!

Newest Chester Homes under $500,000

$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

$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

$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

$225,000

3 Beds ⋅ 2 Baths ⋅ 5102142 MLS

Nestled on 10 private acres between the towns of Chester and Springfield Vermont, this property offers an exceptional opportunity to build your dream home in a peaceful country setting. A driveway has already been installed, providing easy access to the center of the property where several potential homesites offer the possibility of beautiful mountain and valley views with selective clearing. An existing trailer on the property provides a convenient place to live or use as a base while planning and constructing your new home. With a blend of privacy, natural beauty, and existing improvements, this property is ready for you to bring your vision to life while remaining just minutes from shopping, dining, and year-round outdoor recreation. Selling as-is and needing at least 60 days to close. Also listed under MLS #5102143.

3781 Flamstead Rd, Chester

$249,500

5097621 MLS

Entrepreneurs and investors take note! This commercially zoned property offers exceptional potential for a home-based business, investment opportunity, or live/work lifestyle. The property features an oversized barn, multiple outbuildings, and ample space to support a wide variety of business ventures, workshops, storage, or hobby pursuits. The home is currently configured as two charming apartments, each showcasing timeless character with features such as stained-glass windows, soaring ceilings, and abundant natural light. The first-floor apartment boasts a beautiful brick fireplace with a classic hearth in the kitchen and opens directly onto a private patio, creating a warm and inviting living space. The impressive barn includes a heated workshop area, making it ideal for artisans, contractors, mechanics, or anyone needing year-round workspace. Whether you're looking to establish a small business, expand your existing operation, or simply enjoy the flexibility of extensive storage and workspace, this property offers endless possibilities. Conveniently located on Route 103 between Chester, Springfield, and Ludlow, the property provides excellent visibility, easy access, and ample parking for customers, clients, and guests.

3668 Vt Route 103 N, Chester

$229,500

4 Beds ⋅ 3 Baths ⋅ 5097620 MLS

3668 Vt Route 103 N, Chester

$445,000

5 Beds ⋅ 4 Baths ⋅ 5095551 MLS

Step into a piece of Chester's history with this sprawling Folk Victorian offering over 3,800 square feet of living space, five bedrooms, and four bathrooms. Rich in character and architectural detail, this home offers the space and flexibility to accommodate a variety of lifestyles. Inside, you'll find generously sized rooms throughout, including a spacious living room anchored by a wood-burning fireplace and a large entertainment room complete with a wet bar, creating an ideal setting for gatherings, celebrations, or relaxing at home. The thoughtfully designed primary suite features a beautiful en-suite bathroom, while first-floor laundry adds everyday convenience. The flexible floor plan provides abundant space for family, guests, remote work, hobbies, or multi-generational living. Outside, a paved driveway leads to a detached one-car garage, and the level backyard offers plenty of room for recreation, gardening, pets, or outdoor entertaining. Mature trees and established landscaping create a natural buffer from the road, providing a sense of privacy while remaining just moments from Chester's village amenities, shops, restaurants, and community events. Combining historic character, generous living space, and a highly desirable location, this is a rare opportunity to own one of Chester's classic homes. Conveniently located just minutes from I-91 and within easy reach of Okemo Mountain Resort, Magic Mountain, Bromley Mountain, Stratton Mountain, and other Southern Vermont outdoor destinations, this property offers year-round access to skiing, hiking, recreation, and travel throughout the region.

81 Main St, Chester

$449,000

3 Beds ⋅ 2 Baths ⋅ 5095486 MLS

Located on the edge of the Historic Stone Village of Chester, this thoughtfully renovated and reimagined circa 1880 home combines modern style with artisan craftsmanship. Set on .33± acres, this light-filled property features wide-pine floors, exposed beams, and a Vermont Castings woodstove enhancing an inviting open-concept living space. The kitchen/dining has butcher block counters, attractive center island with Vermont slate/stone counter, framed by a wall of windows with a picturesque valley view. A spacious first-floor bedroom and full bath with laundry provide easy one-level living. Upstairs, two additional bedrooms with generous closets share a stylish full bath finished with classic subway tile. Recent upgrades include energy efficient systems and a new four-bedroom leach field. Walk to the market and charming village shops, antique stores and restaurants. Enjoy the recreation area, with its disc golf course, pickleball/tennis courts and sledding hill. Ideally located within 20 min. of Okemo Mountain Resort and Magic Mountain and within 40 min to Stratton or Bromley. This easy maintenance Vermont home is equally suited as a primary residence or second home.

3208 Green Mountain Tpke, Chester

$75,000

2 Beds ⋅ 1 Baths ⋅ 5093286 MLS

Nice country spot with older mobile home on it. Property is located in a flood zone so if removed could not be replaced with a permanent structure. Power, septic and electric on sight along with a 1 car garage. Home could be repaired, would also make a great spot for a snowbird wanting a spot in Vermont or anyone looking to park an RV. Property is sold AS IS CASH ONLY

1144 Potash Brook Rd, Chester

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