Chester VT Real Estate & Homes for Sale

Bring Your Vision to Life in Beautiful Chester, Vermont! Discover the potential of this partially constructed A-frame home nestled on approximately 2 acres along VT Route 11 in scenic Chester, Vermont. Offering approximately 980 square feet of planned living space, this 3-bedroom, 2-bathroom property presents an exciting opportunity for investors, builders, contractors, or buyers looking to create a personalized Vermont retreat. The renovation is awaiting a complete build-out, including windows, doors, and all interior and exterior finish materials, allowing the next owner to take the project from its current stage to a finished home tailored to their vision. With its distinctive A-frame design and nearly 2 acres of land, the property offers a blank canvas for a weekend getaway, year-round residence, or investment opportunity. Enjoy the possibilities of owning a property in the charming town of Chester, surrounded by Vermont's natural beauty and four-season appeal. Bring your plans, creativity, and finishing expertise to transform this unfinished project into something special. Property is being sold in its current, unfinished condition. Buyers should perform their own due diligence regarding construction requirements, permits, utilities, and completion costs.

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!

Tucked away on a quiet country road, this well-maintained 4-bedroom Cape home offers the peaceful Vermont setting so many buyers are searching for. Set on 12.86 acres, the property has been a place where generations have gathered, and now it's ready for its next chapter. Thoughtfully updated and meticulously cared for, the home features a new roof along with numerous improvements that provide confidence and convenience for years to come. Inside, the practical floor plan includes a desirable first-floor primary bedroom and first-floor laundry, making everyday living comfortable and accessible. The remaining bedrooms offer flexibility for guests, a home office, hobbies, or creative space. Step outside to enjoy beautifully landscaped grounds, a spacious deck built around an above-ground pool, and the quiet surroundings that define rural Vermont living. Multiple barns and sheds provide exceptional versatility, whether you're looking for a workshop, tractor or recreational vehicle storage, equipment space, or even a former horse stall ready for new possibilities. Combining privacy, usable acreage, and a property that has been lovingly maintained over the years, this home offers the opportunity to enjoy country living without sacrificing comfort. Whether you're looking for room to spread out, space for projects, or simply a peaceful place to call home, this property is ready to welcome its next owners.

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.

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!

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.

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.

Located on the edge of the Historic Stone Village of Chester, this thoughtfully renovated and reimagined circa 1880 3 bedroom, 2 bath home has the character of a VT farmhouse while being totally updated. 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, that looks out over to a picturesque valley view. A spacious first-floor bedroom and full bath with laundry provides 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.

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

Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal style farmhouse set on 7.8 private acres just minutes from town. Rich in historic character and thoughtfully updated for modern living, this exceptional property offers the perfect blend of comfort, charm, and year-round recreation. Inside, you'll find four spacious bedrooms, wide plank wood floors, and inviting gathering spaces designed for relaxed country living. The heart of the home is the warm and welcoming country kitchen featuring soapstone counters, a center island, and ample room for entertaining. A large living room with a pellet stove creates a cozy retreat after a day on the slopes or trails, while the den offers an ideal space for a home office or quiet study. The screened front porch captures the essence of Vermont living perfect for morning coffee, evening conversations, and taking in the peaceful surroundings. Outdoors, enjoy evenings around the fire pit beneath star filled skies, surrounded by the natural beauty and privacy of the property. A standout feature is the remarkable multi-level 55' x 40' barn, full of rustic character and endless potential. Having hosted countless gatherings and celebrations, it offers incredible space for entertaining, hobbies, storage, or future creative use. Tucked away just two miles from town, this serene retreat offers both privacy and convenience, with easy access to skiing, snowmobiling, hiking, and all the outdoor adventure and small town charm that make Vermont so special.

Set on 18 private acres, Popple Fields is a very special Vermont property one that feels less like a house that was built and more like a home that was lovingly crafted. Built in 1989 by its owner, a true master craftsman, this Williamsburg saltbox reproduction reflects a lifelong appreciation for traditional architecture, fine woodworking, and the quiet beauty of things made by hand. The builder was a skilled Windsor chair maker whose work was featured in Yankee Magazine, and that same extraordinary attention to detail can be felt throughout the home. Inside, the craftsmanship is warm and beautifully understated. Wide plank wood floors, paneled walls, reclaimed beams, layered moldings, and custom woodwork give the rooms an authentic sense of age and character. The house has the gracious proportions and enduring appeal of an earlier era, while offering the comfort and livability of a thoughtfully designed modern home. Originally created as a bed and breakfast. There are inviting spaces for conversation and entertaining, along with quieter rooms that offer privacy and retreat. The result is a home that feels equally natural filled with family and friends. The land is every bit as evocative. Stone walls, established gardens, wildflowers, fruit trees, and a blueberry patch unfold across the 18 acres. There is a wonderful feeling of discovery here paths to wander, gardens to tend, places to sit, and changing views through every season. A woodworking barn adds another layer of possibility, A genuine space for woodworking, craftsmanship and other creative pursuits. Just outside the charming village of Chester, Popple Fields is ideally situated to enjoy skiing, hiking, and exploring the surrounding countryside. But what makes this property truly distinctive is something that is difficult to replicate: the hand of the maker. The home carries the mark of the craftsman who designed and built it. This is a private VT retreat to be enjoyed for generations.

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.

This property is a handy man's dream for someone who has a vision of finishing a house and turning it into their own sanctuary. The bones of the house are in place, furnace and piping for heat are in, rough plumping and wiring are done, and most sheet rock is completed. Gas fireplace is mounted and vented to outside and kitchen cabinets are on site. It boasts a little over 2000 square feet of living space 4 bedrooms, 2.5 bathrooms. It sits on the banks of the Williams River on a dead end street and treed backyard area. First floor consists of a large kitchen and livng room and a half bath. The second floor has a beautiful sized primary bedroom with ensuite bathroom. There are also 3 bedrooms and a 3/4 hallway bathroom.