Chester Real Estate

Discover the perfect blend of rustic elegance and modern versatility at 34 Edwards Mill Road. Set on 3.89 expansive acres in the scenic countryside of Chester, NH, this stunning log home offers a serene lifestyle for any stage of life. Are you looking for a natural playground where you can explore the woods and the soothing waters of Towle Brook, or wanting a peaceful New Hampshire retreat with single-level living potential, this property delivers. The spacious interior has been thoughtfully maintained with fresh paint, featuring 9 spacious rooms including 4 bedrooms and 2 full bathrooms. The home’s flexible layout includes a first floor primary bedroom suite that opens directly into a gorgeous huge sunroom. For those prioritizing convenience, the first-floor separate laundry room facilitates true single-level living options. Recent updates ensure peace of mind, including log maintenance, new gutters, and freshly seal-coated driveway. Outdoor enthusiasts and hobbyists will fall in love with the substantial detached 3-car garage which features a brand-new roof, a convenient drive-through bay with heat and water access. Above, an enormous unfinished space presents incredible potential for a studio, storage, or an accessory dwelling unit (ADU), subject to approvals. Outside, the enormous 50 ft. deck provides the ultimate spot for hosting gatherings or simply relaxing to the sounds of the brook winding through your private acreage. Experience total privacy without sacrificing accessibility; this retreat is located just 25 minutes from the Massachusetts border and approximately one hour from the heart of Boston. This home has been lovingly cared for and is ready for its next chapter. Schedule your private tour today to experience the charm & serenity of this stunning Chester retreat. You won't want to leave.

34 Edwards Mill Rd, Chester

$100,000

5100755 MLS

Situated in the heart of Chester, Vermont, this 0.55-acre parcel offers approximately 254 feet of frontage on Depot Street and 254 feet of frontage on First Avenue - both public, paved roads with a sidewalk accessible on Depot Street. The land is open, landscaped, and dotted with apple trees, creating a welcoming setting for your future plans. Town water and town sewer are available at the street, adding convenience for development. A gravel driveway provides easy access from First Avenue, and a recent survey is available. An existing foundation remains on the property and may offer the potential to be repurposed for a garage, shed, or other accessory structure. Buyers should perform their own due diligence and consult with a qualified contractor regarding its condition and suitability, as no representations or guarantees are being made. Enjoy a convenient location just 0.6 miles from the Chester Farmers Market and The Common shopping plaza, where you'll find local shops and cafés. The nearest hospital is approximately 10 minutes away, and Boston MA is 2.5 hours away, making this an ideal location for a primary residence, vacation home, or investment opportunity. Whether you're looking to build now or invest for the future, this well-located lot combines accessibility, utilities, and small-town Vermont charm.

427 Depot St, Chester

$925,000

5 Beds ⋅ 3 Baths ⋅ 5099745 MLS

Escape to the charm of Vermont in this spacious 5-bedroom, 3-bath country home, perfectly set amidst open meadows with a picturesque swim pond and peaceful surroundings. Designed for both everyday living and entertaining, this inviting property offers the perfect balance of rustic character and modern comfort. Step inside through the practical mudroom, where you'll be welcomed by a dramatic family room featuring soaring vaulted ceilings, a cozy wood-burning stove, and a loft overlooking the space. The heart of the original 1860's home is the open-concept living area, complete with a well-appointed kitchen, dining area, and a warm, inviting living room centered around a classic wood-burning fireplace. The main level also features a convenient half bath and a private primary suite with a ¾ bath. From the primary bath, step directly onto the back deck and unwind in the sunken hot tub while taking in the tranquil country setting. Second level, you'll find four additional bedrooms, a full bath, and a comfortable den/loft overlooking the family room, offering flexible space for guests, a home office, or recreation. Outside, enjoy Vermont's beauty from the private covered porch, gather around the expansive yard, or relax by the stone firepit or scenic pond surrounded by open meadows. An attached garage provides ample storage, while the finished game room above creates the perfect space for entertaining, hobbies, or additional guest accommodations. The flat meadows were the perfect setting for the family's recent wedding... What event will you host in this incredible backyard? Ideally located just minutes from the charming village of Chester and within easy reach of Okemo Mountain Resort, this exceptional property offers year-round enjoyment, whether you're seeking a full-time residence, a vacation getaway, or an investment opportunity. Visit the Okemo real estate community today. Taxes are based on town assessment.

1470 Popple Dungeon Rd, Chester

$229,000

5098347 MLS

27.8 +/- acre wooded parcel close to Chester Village with potential long range views. Driveway has been cut and a clearing prepared at the entry to the land for a house site and a Vt state approved 4 bedroom wastewater Permit. Potential views from the plateau along the ridge accessed by an established logging road. Soil tests indicate a 3 bedroom home site is possible at the scenic viewpoint. Property has old stone walls and has gorgeous rocks and stone on site for landscaping. Adjoins town forest along the back property line. The 27.8 acres meets the minimum requirement for enrollment in the VT Current Use Forestry program for tax savings. Close to the charming village of Grafton for x-country skiing and dining at the historic Grafton Tavern. Okemo, Magic and Bromley Mountains are within easy reach. 15 min. to I91. Whether you are a summer recreational enthusiast, enjoy winter sports, or just want to chill in a small village atmosphere, this property is ready for your building plans!

00 Quarry Rd, Chester

$199,000

2 Beds ⋅ 1 Baths ⋅ 5098053 MLS

Set on 18 forested acres along quiet, dead-end Potash Brook Road in Chester, this peaceful cabin offers a simple and inviting Vermont retreat with no through traffic and a true sense of calm. Well suited for a hunting camp, recreational getaway, or quiet place to unwind, the property provides privacy, natural surroundings, and easy access to the outdoor lifestyle Southern Vermont is known for. The cabin includes propane heat, a spring well, septic, and an inviting and cozy living space for weekends, seasonal use, or time away from the noise of everyday life. The structure will require new footings and is being sold as is, offering an opportunity for the next owner to make needed improvements while enjoying the land, setting, and existing cabin. The property is wooded and rustic in feel, with room to explore, observe wildlife, and enjoy the changing seasons. A brook runs through the land, adding natural character to the setting. Whether used as a base for hunting, hiking, snowmobiling, skiing, or simply relaxing in the woods, this property offers a practical and appealing Vermont escape. Ski areas, trail networks, fishing, and year-round recreation are all within reach, while the setting itself remains quiet, private, and refreshingly simple. If you are looking for land, privacy, and a modest cabin with key systems already in place, this Chester retreat is well worth a look.

1372 Potash Brook Rd, Chester

$850,000

4 Beds ⋅ 3 Baths ⋅ 5097911 MLS

Looking for a 4-bed colonial in Chester with space, privacy, and an ideal layout for entertaining? Welcome to 43 Emerson Road Where timeless Colonial charm meets comfortable everyday living. This well-maintained home set on two private acres is in a desirable cul-de-sac neighborhood. Enjoy spacious living areas, inviting outdoor spaces. Nestled on 2 private acres in a peaceful cul-de-sac neighborhood, this 4-bedroom, 3-bathroom Colonial offers the perfect balance of privacy, community, and convenience. The open and inviting first floor is designed for both daily living and entertaining, featuring a spacious kitchen, formal dining room, and an expansive family room with a soaring vaulted ceiling and cozy gas fireplace. New carpeting adds a fresh touch, making this home move-in ready. Step outside to your own backyard retreat featuring a multi-tiered deck, sparkling pool, and a private outdoor oasis designed for summer gatherings, barbecues, and relaxing evenings with family and friends. The generous two-acre lot provides room to play, garden, or simply enjoy the peaceful natural surroundings. Not far from shopping, dining, recreation, and major commuter routes while still offering the charm and tranquility that make Chester one of southern New Hampshire's desirable communities. Served by the highly regarded Pinkerton Academy school district. Whether you're hosting memorable celebrations or enjoying quiet evenings at home, this property delivers the lifestyle you've been searching for. Come experience everything 43 Emerson Road has to offer and discover why so many are proud to call Chester home. Schedule your private showing today. Showings begin Monday July 6, 2026

43 Emerson Rd, Chester

$649,000

3 Beds ⋅ 2 Baths ⋅ 5097737 MLS

Welcome to your private gated mini-estate...an enchanting sanctuary where every detail delights the eye. Nestled adjacent to meticulously manicured woods, this one-of-a-kind residence blends storybook charm with thoughtful, high-end finishes. A sweeping entry leads past intimate outdoor living spaces centered around a dramatic floor-to-ceiling exterior fireplace, perfect for cool evenings and quiet reflection. Step inside to discover warm, curated interiors where a matching floor-to-ceiling indoor fireplace anchors a cozy great room...an ideal focal point for gatherings and quiet nights in. The custom kitchen is a chef’s and designer's showcase making meal prep effortless and stylish. Cute, artful decor and exceptional millwork accentuate every room..every little detail has been considered and executed with eye-popping precision. Natural light pours through thoughtfully placed windows, highlighting textures, finishes, and curated vignettes around nearly every corner. In addition to the four private bedrooms, the special loft above the second-floor den offers a “fun” sleeping area and great retreat for the “kids”. Unique sightlines and charming nooks reveal something special at every turn.unexpected architectural details, refined accents, and cozy gathering spots create a home rich in personality and comfort. The floorplan flows intuitively while offering distinct spaces for entertaining and everyday living. Practicality meets luxury with a spacious second garage providing room for toys, workshop space, or secure storage perfect for multi-vehicle households or hobbyists. The gated setting ensures peace of mind and exclusivity, while the manicured wooded grounds offer a serene backdrop and a strong connection to nature. Come see how every corner captures your attention and inspires a sense of wonder at home. This mini-estate is only 10 miles from world-class skiing at Okemo and golf at Fox Run...then enjoy the 5 lakes of Okemo Valley and the nearby VAST trails!

168 Chandler Rd, Chester

$750,000

3 Beds ⋅ 2 Baths ⋅ 5097722 MLS

Tucked away on a quiet country road in one of Chester’s most coveted areas, this striking contemporary home offers the ultimate Vermont lifestyle, just miles from the Okemo Mountain base lodge. Embraced by nature and thoughtful landscape, the property seamlessly connects refined indoor living with the natural beauty of its private riverfront, complete with your own summer swimming hole. Inside, the main level centers around a commanding, floor-to-ceiling fieldstone wood-burning fireplace, beautifully complemented by rich hardwood floors and a bespoke custom kitchen. Designed for privacy, the primary suite features a spa-like ensuite bath, while two additional guest bedrooms and a 3/4 bath provide plenty of space for family or weekend visitors. Intelligently designed for flexible living, the upper-level loft serves as an inspiring home office or studio, while the bright, walk-out lower level offers incredible potential for a game room, home gym, or ski lounge. Transition effortlessly outdoors to the oversized front deck for morning coffee, or unwind in the expansive screened porch out back listening to the sound of the river. The detached, insulated, oversized, 2-bay, 2-level barn has full electrical service, electric garage doors, and a workshop with extra storage space. There is a greenhouse perfect for gardening. With direct access to nearby VAST trails for winter recreation, this is a true four-season retreat. Visit the Okemo real estate today. Taxes are based on the current town assessment.

955 Smokeshire Rd, Chester

$875,000

4 Beds ⋅ 3 Baths ⋅ 5097711 MLS

50K PRICE CUT! OPEN HOUSE | 11AM to 1PM | Sunday, July 26th, 2026 Welcome to 88 Crawford Road, a breathtaking residential haven nestled in the heart of Chester, New Hampshire. The Property This exquisite colonial estate seamlessly blends sophisticated architectural design with the tranquil beauty of its lush, private surroundings. Offering an expansive 3,675 square feet of meticulously crafted living space, the residence features 4 generously appointed bedrooms and 2.5 elegant bathrooms. From the grand, winding driveway to the majestic facade framed by mature trees, every detail of this home exudes luxury. The interior promises unparalleled comfort with expansive room layouts, high-end finishes, and an abundance of natural light pouring through magnificent feature windows. Location & Drivability Perfectly situated for those who demand both privacy and convenience, 88 Crawford Road offers an idyllic retreat without sacrificing accessibility. Located in the charming, historic town of Chester, you are mere minutes from top-rated local schools, pristine parks, and boutique community dining. For commuters, the property provides seamless access to major regional routes, putting the bustling commercial hubs of Manchester and Salem within easy driving distance, while offering a straightforward, scenic commute to downtown Boston and the gorgeous New Hampshire seacoast.

88 Crawford 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

$249,500

4 Beds ⋅ 3 Baths ⋅ 5097620 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

$789,000

5 Beds ⋅ 3 Baths ⋅ 5097600 MLS

Exceptional design, enduring craftsmanship, and an unrivaled Vermont setting define this remarkable custom residence on 11± beautifully landscaped acres just a short stroll from the village of Chester. Offering more than 3,600 square feet of thoughtfully designed living space, the home was built to an exacting standard where quality materials, timeless architecture, and exceptional attention to detail create a residence as enduring as it is beautiful. A flexible floor plan offers five bedrooms and three baths, including an elegant first-floor primary suite with ensuite bath, complemented by additional main-level bedroom options ideal for guests, multi-generational living, or a dedicated home office. Upstairs, two spacious bedrooms each feature adjoining bonus rooms perfectly suited as executive offices, dressing rooms, studios, or generous walk-in closets, while additional unfinished space presents exciting opportunities for future expansion. Designed for effortless entertaining and comfortable everyday living, the heart of the home is an open-concept kitchen, dining, and living area filled with natural light. A handsome library offers a quiet retreat, while integrated whole-home audio enhances the experience throughout. An oversized laundry and mudroom connects seamlessly to the attached two-car garage, delivering exceptional convenience without compromising design. Outside, mature gardens, specimen trees, and thoughtfully curated outdoor living spaces create a setting of remarkable beauty and privacy. Relax beneath the covered porch, entertain with family and friends, or simply enjoy the peaceful surroundings. Ideally located just minutes from Okemo, Stratton, Magic, and endless four-season recreation, yet within walking distance of Chester's vibrant village, this exceptional property offers a rare combination of privacy, convenience, and refined Vermont living. A home of lasting quality, exceptional versatility, and unmistakable character!

223 Coach Rd, Chester

Chester Real Estate

Newest Listings in Chester