Properties Near 175 Pleasant Valley Road Springfield, VT

Tucked away at the end of a quiet cul-de-sac just one minute from the heart of town, this 4-bedroom retreat offers a rare blend of privacy, possibility, and connection to nature. Set on 3 mostly open acres with glimpses of the mountains and the soothing soundtrack of the nearby river, this is the kind of home that changes pace the moment you arrive. The heartbeat of the home comes from a bright and inviting great room that opens through sliding doors to an expansive deck where mornings begin with coffee and birdsong, and evenings end with the sound of rushing water under the stars. The flowing layout offers spaces that adapt beautifully to modern living — a dedicated office for remote work, room for a home gym, studio, creative retreat, media lounge, or whatever your lifestyle calls for next. The dining room is ready for gatherings both large and small, while the attached 2-bay garage and generous outdoor space make everyday living feel effortless. Whether you're hosting friends, growing a garden, creating art, working from home, or simply looking for a peaceful place to recharge, this property offers the flexibility to make it your own. Private yet convenient, peaceful yet connected — this home delivers a lifestyle that’s increasingly hard to find.

Located on 17 acres, but close to schools, shopping, medical services and recreation, this property offers privacy, views and a pond. This property also enjoys a beautiful guest house for visitors or a long-term rental. The main house is a traditional cape style with an abundance of porches for viewing wildlife. The entrance foyer and sitting area leads to the living room and the large dining room featuring built-ins. The oversized kitchen provides space for dining or perhaps an island, as well as family room space in front of the wood stove. The primary bedroom enjoys a private sitting area, office or perhaps your yoga space. With 2 more bedroom and 2 baths it is truly a delight. The detached garage hosts a studio/office space overhead. The second living space is located over the 2-car garage and is stunning with the interior done in wood, stonework, tile and more. The open concept living, dining and kitchen features plenty of cabinets and storage. The generous bedroom and bathroom are roomy and comfortable. The sunporch has room for the hot tub and offers views of the pond and mountains. The property has fruit trees, stone walls and some trails with land to develop more for walking or snowshoeing.

Set along a quiet country road, this inviting 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and Vermont charm. The open-concept layout features high ceilings and abundant natural light, creating a warm, airy feel throughout. A spacious primary suite includes a jetted tub and walk-in closet, providing a true retreat at day’s end. Step outside to a sunny, open lot with a peaceful pond, expansive deck ideal for entertaining, and a handsome shed for storage or hobbies. A recent fresh coat of interior paint and a newer high-efficiency boiler add modern reliability and make this home move-in ready. The large unfinished basement offers excellent potential for additional living space, a home gym, or a workshop. Ideally located near Okemo, Magic, and Stratton Mountains, with easy access to local dining, shops, and year-round recreation. This in a truly special location that is both private and practical.

Built in 1803, this home has lived many lives and still stands with purpose. Set within one of Chester’s historic districts, it sits naturally among period homes and the steady pace of village life. The lot is larger than what is typical in town, room for garden , 2 horse stalls and even a horse paddock near the river. It’s a property that allows you to live outwardly—work the land, keep animals, or simply enjoy open, private space. Inside, the home is warm and inviting, with a layout that supports both daily living and gathering. The large living room, anchored by two fireplaces, is a natural place to slow down. A formal dining room is ideal for hosting, and a generous room off the kitchen easily accommodates larger meals and celebrations. Original wood floors, exposed beams, and durable early craftsmanship add character throughout. A separate rental unit, currently occupied, provides steady income or flexible use for guests, family, or workspace. The barn offers storage, workshop potential, or agricultural use, expanding what the property can support. Chester’s shops and everyday conveniences are close by, and skiing, rivers, and trails are within easy reach. Okemo is just minutes away, with Stratton, Magic, and Bromley all within a short drive of 20-30 minutes. Several AT access point within similar distance. The Okemo Valley is on your doorstep, and it's magical! This is a historic home ready for its next chapter—solid, adaptable, and full of possibility. Come See Today!!

MOTIVATED SELLERS!!! This could be your escape to your own peaceful, private homestead. Set on 7.5 acres of wooded and open land this property is truly a respite from the stresses of the world. This multi-level 3-bedroom, 3 bath home offers convenience and options. The spacious living room with hardwood floors leads to a large eat-in kitchen with ample storage and room for an island if desired. Step into the Family room or a large dining room with access to one of the decks overlooking the pond. The primary bedroom on the third level has a convenient 3/4 bathroom as well as a deck to again enjoy the views of wildlife and the pond. An additional second floor bedroom also enjoys a deck to enjoy the view and wildlife. A full bathroom is convenient on level 3. On the lower level a large family/game room awaits with a wood stove to keep you warm on those chilly nights and offers full access to the back acreage. In addition, a 3rd bedroom and full bath/laundry room make this a true family home. Wait, there is more, an oversize 2 car garage, heated, for those cool nights, and also an attached work shed, for all the woodworking or hobbies one might enjoy, as well as 1/4 bath for convenience. Over the garage an open concept apartment features living room, kitchen, 1 bedroom and bath. It has been used as a rental, which one could continue or perhaps use as a guesthouse or Air B&B. The pond is a bonus and ready for enjoyment during the summer months. The property is located with easy access to Springfield and Chester for all your shopping, medical and recreation needs. Hiking, golfing, skiing, entertainment, movie theatre, arts and more.

Located in the village of Chester, this 4-bedroom, 3-bath property offers a rare amount of space and flexibility for an in-town setting. You’ll enter through the heated attached two-car garage into a layout that’s both functional and easy to live in, with room to spread out when you need it and gather when you want to. The kitchen features warm wood cabinetry, a breakfast bar, and a flexible area that works just as well for casual dining as it does for a home office setup. The dining space flows easily into a sunken living room, where the pellet stove becomes a natural gathering spot. Two bedrooms on the main level, each with their own bath, make this a great fit for a variety of living situations. Upstairs, you’ll find a spacious bedroom, a separate flex room currently used as a movie room, and an unfinished bonus area ready for whatever you have in mind. Storage is not an issue here, between the closets and full basement, there’s plenty of space to keep things organized. The home is equipped with a new furnace and four heating zones, offering efficiency and control throughout. Outside, a wide back patio gives you a great place to relax, while the barn and oversized three-bay garage offer serious utility for storage, equipment, or hobbies. The detached garage is currently rented for $500 per month, and the tenant would be open to continuing that arrangement with the next owner. The property borders Lovers Lane Brook, adding to the natural setting and privacy, all just minutes to Chester’s shops, dining, and village amenities. If you’ve been looking for an in-town property with more space and versatility than most, this one is worth a look. Furnishings are negotiable for anyone looking for a truly turn-key property!

Welcome to a property where Vermont’s natural beauty meets a lifestyle of quiet productivity and potential. Situated on 18.45+/- private acres in Springfield, this 1988-built home spans 2,548 square feet of living space designed to celebrate its surroundings. The heart of the residence is defined by its exceptional southern exposure; several sliding glass doors line the south-facing side of the home, flooding the interior with an abundance of natural light and creating a seamless connection to the expansive grounds outside. The thoughtful layout offers long-term versatility, featuring a spacious primary bedroom suite conveniently located on the first floor, while the second story houses three additional bedrooms and a full bathroom, providing plenty of room for guests, a home office, or a growing household. For those who value functional workspace, the extra-tall garage is a standout feature, offering the rare vertical clearance necessary for storing heavy machinery, tractors, or creating a professional-grade workshop for equipment maintenance and creative projects. The land itself is a dream for the outdoor enthusiast, offering prime sun exposure and acreage that is perfect for gardening or establishing a light homestead. Whether you envision sprawling vegetable beds, small-scale agriculture, or simply enjoying the privacy of the acreage, the infrastructure is in place to support your vision. Inside, the home continues to offer room for growth and relaxation; the full basement currently houses a private hot tub—a perfect sanctuary for unwinding after a day spent outdoors—and remains unfinished, providing a straightforward opportunity to easily add significant finished square footage to the home. This property is more than just a house; it is a canvas for a sustainable, light-filled life in southern Vermont, offering the perfect balance of immediate comfort and the space to build your own legacy.

The Best of Both Worlds: Modern Comfort Meets Village Charm! Discover the perfect blend of contemporary upgrades and serene neighborhood. This meticulously updated raised ranch offers an expansive layout designed for both effortless entertaining and comfortable daily living. Step inside to find a light-filled open-concept living and dining area, anchored by stunning hickory hardwood floors that flow throughout the main level. The heart of the home is the fully renovated kitchen, featuring modern finishes, apron front farmhouse sink and outfitted with stainless steel appliances. With 5 spacious bedrooms, 2 updated bathrooms, there is no shortage of space. Enjoy cozy evenings in the living room featuring a vaulted ceiling and exposed wood beams and a gas fireplace. The primary suite serves as a retreat complete with a private balcony, and an ensuite bath featuring a double vanity. On the lower level, a large bonus room provides the flexible space you’ve been looking for-ideal for a gym, playroom or office! Enjoy the fresh air without the bugs in your screened-in porch, or host summer gatherings in the peaceful yard. Located on a quiet dead-end street, this home offers privacy while remaining incredibly convenient. Additional highlights include an easy walk to the vibrant Chester Green, peace of mind with a new boiler in 2021, freshly painted interior in 2022, sump pump installed in 2023, a 1 car garage, a paved driveway done in 2024, and new windows installed throughout most of the house in 2025. Don't miss your chance to own this move-in-ready gem in a prime Chester location!

No words describe this property better than peaceful, rural, convenient and historic. Throughout its long life, the top of Elm Hill exudes country. The rugged stone walls, lower barn, tool shed and upper barn reveal an agricultural past. The upper barn has been converted to a 2-car garage and workshop, complete with a half-ton hoist. The upstairs hayloft (attic type storage) is easily accessible by stairs in the back and double doors on the front. The carriage port has been enclosed to store wood for the Defiant woodstove in the sitting room, adjoining the kitchen. On the south side are a five-tree apple orchard and a garden plot each producing for residents and neighbors alike. Sunshine and natural light define the yard, the views and interior, Foundation plantings thrive in the morning sun. The back hills and fields light up in midday and evening sun. During foliage, the hills across the valley blaze in the sunset. Multiple windows flood the house interior with natural light. Convenience doesn't negate peace. A mere mile from the town central square, where one will find a variety of unique shops, restaurants and even a movie theatre. The house is but a 1.1 mile from the shopping plaza and 1.5 miles from the hospital and with a golf course, ski areas and multiple hiking venues nearby, one can easily get back to nature. In the early morning and evening turkey and deer come from the back hill to feed in the adjoining meadows as well as a variety of colorful songbirds to enjoy. A classic post and beam 4 bedroom, 2 bath home on 1.2 acres was built by James Litchfield when he settled the top of Elm Hill. The original axe-cut post and sturdy beams exposed on the main floor living room, dining room and office attest to its structure and history. Since the first family made this their home in the early 1790s, it has sheltered and nurtured eight families of several generations each. Yours can be the next family to make history here. Come experience the peaceful setting.