You are viewing all VT listings NH Homes between $250000 and $500000 dollars.
New Listing!
$365,000 $197 per sq.ft. Chelsea VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1850 | Acres: 0.17Listed on Friday Jul 31, 2026
Description: Chelsea is quintessential small town Vermont - Main Street is lined with century homes, a general store, a natural foods store, a dance hall, and the beautiful town green. Just up the hill on the paved road sits this immaculate country cape! Built in 2017 with great attention to detail, you won't find a home this fresh and new for miles around. The main level offers a comfortable open layout, first floor laundry, essential drop space at the door, a gleaming country kitchen with sparkling butcher block counters, tile backsplash, and an island perfect for entertaining and everyday use. A large full bathroom and a bedroom/office round out this beautiful first floor. Upstairs, you have another updated full bathroom, gigantic freshly-painted primary bedroom, and another bedroom with great built-ins and plenty of light. The full unfinished basement offers excellent storage and work space, and stays bone dry. Outside, you have a picturesque front porch to relax and entertain on, with raised garden beds on the lawn ready for next spring. The trickling stream out back is tranquil and soothing on this stunning property. Come make your home in Chelsea! See Listing Details & 54 images.
$399,000 $283 per sq.ft. Chelsea VT Home »
Price Change! Reduced by $36,000 down 9% on July 14th 2026
3 Beds | 3 Baths | Total Sq. Ft. 1552 | Acres: 5.04
Listed on Sunday Jun 14, 2026
Description: Somewhere between the rolling hills of Chelsea and the rest of the world, there exists a place that feels borrowed from Tolkien's imagination, a real-life Shire where the land is green, the air is clean, and time moves at the pace of a babbling brook. This five-acre oasis is the kind of property you don't find; you stumble upon it and wonder how it escaped everyone else. Mature maples stand like quiet sentinels, a working apple orchard offers its seasonal gifts, and a brook winds softly through the grounds, bucolic, unhurried, alive. The 1991-built home offers 3 bedrooms and 3 bathrooms with a vaulted, skylit living room, a main-floor primary suite, and a generous kitchen and dining area that opens to a back deck and the woods beyond. Upstairs, a large landing for reading nook/office and a bedroom. Downstairs on the lower level you'll find another bedroom, bathroom and laundry with storage. The lower level walks out to the side yard for storage and access. A large detached shed offers space for the garden implements necessary to maintain your little apple orchard and the property at large. And unlike the Shire, this Eden comes with fiber optic internet, a standing seam roof, wood/oil combo boiler, and a whole-home generator. Even hobbits need WiFi. Your home. Your escape. Your Vermont. See Listing Details & 47 images. Includes a Virtual Tour
Under Contract
$445,000 $259 per sq.ft. Chelsea VT Home »
2 Beds | 2 Baths | Total Sq. Ft. 1718 | Acres: 21Listed on Thursday Aug 21, 2025
Description: Exceptionally well built classic cabin with soaring vaulted ceilings and stunning mountain views! Cozy radiant floor heat keeps the home comfortable year-round, while the thoughtful layout checks all the boxes. The full walkout basement is partially finished and offers endless possibilities create a home gym, craft room, family room, or additional living space (see virtually staged photos for inspiration). The lower level also features a spacious laundry room complete with a ¾ bath, making it ideal for guests and ready for your finishing touches. A separate staircase provides direct access to the deck and leads into a generous mudroom that flows seamlessly into the inviting living room, where abundant natural light and beautiful views create a warm and welcoming atmosphere. Step outside to the recently updated deck and enjoy exceptional privacy, surrounded by more than 20 acres of peaceful woodland. Upstairs, the spacious loft offers charming built-in storage and flexible space for sleeping, working, or relaxing. This is the perfect blend of rustic charm, comfort, and Vermont tranquility. Please, no drive-bys--shown by appointment only. See Listing Details & 38 images.
$299,000 $167 per sq.ft. Chester VT Home »
Price Change! Reduced by $150,000 down 50% on July 29th 2026
3 Beds | 2 Baths | Total Sq. Ft. 1788 | Acres: 3.3
Listed on Wednesday Jan 14, 2026
Description: Set on 3.30 acres in the hills of Chester, Vermont, this 1900-built home delivers the kind of setting people move here for flowing water, open land, quiet roads, and easy access to the mountains. The property overlooks a gently moving brook and includes ownership on both sides of the water, giving you your own private stretch of stream and a natural buffer of woods and open space. A quiet paved road leads you home, winding past back woods and pastoral farmland before arriving at the property. The elevated deck becomes your front-row seat to the landscape below--perfect for morning coffee, summer dinners, or simply listening to the brook roll past. Inside, the home feels warm, functional, and comfortable. A large living room is anchored by a substantial woodstove that brings real Vermont heat and atmosphere through the colder months. The sunroom is a standout space, wrapped in windows and overlooking the brook, creating a peaceful place to read, work, or relax. From here, step directly onto the deck and into the outdoors. The layout offers three bedrooms and two bathrooms, including a ground-floor bedroom for easy everyday living. Storage is abundant throughout, making room for outdoor gear, tools, and seasonal equipment. The land itself adds real value. With acreage on both sides of the brook, there's room to garden, explore, build trails, or simply enjoy your own stretch of water and woods. The surrounding countryside delivers classic Vermont scenery--rolling fields, forested hills, and quiet country roads. Located just minutes from the village of Chester and close to Okemo, Stratton, and Magic Mountain, this is a true four-season basecamp for skiing, hiking, biking, fishing, and exploring Vermont's natural beauty. A property that offers privacy, water frontage, land, and mountain access--without giving up convenience. See Listing Details & 31 images.
Under Contract
$325,000 $98 per sq.ft. Chester VT Home »
Price Change! Reduced by $24,000 down 7% on June 14th 2026
4 Beds | 3 Baths | Total Sq. Ft. 3332 | Acres: 2
Listed on Friday May 8, 2026
Description: Some properties just radiate a certain warmth, charm and magic and this home is definitely one of them. Imagine sitting on the front porch and listening the soft rustle of the willow tree leaves and the babbling brook trickling by, then you step inside and feel that you have walked into a home that was truly loved. The large kitchen offers nice upgrades including tile floor, granite countertops and appliances. The main level offers a bedroom, dining room, office space and living room. All of the windows have been replaced (except in the attic), updated electric panel, insulation done by Efficiency VT, new stoves in the barn room and living room (see MLS docs for the complete list). This property is perfect for anyone looking for a TRUE Vermont home with loads of potential. Great natural light, large bedrooms, hardwood floors and attached garage. One of the features I personally love is the screened stone patio (barn room) off the back of the house. The rustic beams and barn boards with wood stove is a wonderful space to relax and entertain. Above is unfinished space ready for your ideas, work out space? yoga studio? game room? There are pretty perennials and gardens surrounding the home. The back yard is private with attached shed space and back deck. Chester is a wonderful community and this home is perfectly situated for easy access to I91, Grafton, ski resorts, shopping and walking to the village green. The sellers have loved owning this home and have created many many memories here. Don't miss your chance to be the next stewards of this truly special property. See Listing Details & 41 images.
New Listing!
$359,000 $399 per sq.ft. Chester VT Home »
2 Beds | 1 Baths | Total Sq. Ft. 900 | Acres: 11Listed on Wednesday Jul 29, 2026
Description: This well built log home packs quite the punch. The open concept first floor spills out onto the generous front deck, essentially doubling the first floor area to roam. Two nearly identical craftsman quality 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, and brand new LVL carrying beam and floor joists 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 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, this home is the perfect forever home or private getaway. The dog on the couch does not convey. See Listing Details & 27 images.
Under Contract
$390,000 $299 per sq.ft. Chester VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1304 | Acres: 1Listed on Thursday Apr 30, 2026
Description: Fully renovated from top to bottom, this Chester property offers the kind of peace of mind that's hard to find in an older Vermont home. Major systems including electrical, plumbing, heating, insulation, drywall, and windows, have all been updated, allowing the next owner to step in without a long to-do list. Inside, the home strikes a thoughtful balance between character and clean updates. Refinished wide plank floors bring warmth throughout, while the kitchen features granite countertops and a farmhouse sink. Upstairs, a vintage Martini pedestal sink adds a distinctive, curated touch to the bathroom. Outside, the level lawn provides usable space for everything from gardening to entertaining, and the substantial post-and-beam barn opens the door to a wide range of future uses, storage, workshop space, or potential expansion. Located just minutes from Chester's Stone Village, the Grist Mill, and Smitty's Market, and within easy reach of Okemo, Bromley, Killington, Stratton, and Mount Snow, this is a strong option for both full-time living and recreational use. Currently used as a long-term rental and previously operated as a successful Airbnb and personal vacation home, the property offers flexibility for a variety of ownership goals. See Listing Details & 51 images.
$399,000 $186 per sq.ft. Chester VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 2148 | Acres: 1.5Listed on Tuesday Jan 6, 2026
Description: 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. See Listing Details & 37 images.
$419,900 $212 per sq.ft. Chester VT Home »
Price Change! Reduced by $5,100 down 1% on July 31st 2026
5 Beds | 2 Baths | Total Sq. Ft. 1982 | Acres: 0.27
Listed on Friday Apr 10, 2026
Description: Welcome to this beautifully updated raised ranch, thoughtfully designed for both relaxed day-to-day living and effortless entertaining. Step inside to an open-concept main level bathed in natural light, anchored by rich hickory hardwood floors that flow throughout. At the heart of the home, the renovated kitchen shines with modern finishes, a classic apron-front farmhouse sink, and stainless steel appliances. Relax by the gas fireplace in the inviting living room, highlighted by soaring vaulted ceilings and rustic exposed wood beams. Accommodating family and guests with ease, the layout features 5 generous bedrooms and 2 updated baths. The primary suite acts as your own private sanctuary, complete with an ensuite bath featuring a double vanity, and a private balcony. The flexible lower-level bonus space easily adapts to your lifestyle - ideal for a home gym, media room, or private office. Outdoor living is a breeze while you're relaxing bug-free on the screened porch! Tucked away on a quiet dead-end street, this turn-key residence pairs privacy with convenience with an easy walk to the vibrant Chester Green. Additional highlights include the boiler replaced in 2021, the freshly painted interior in 2022, new windows installed throughout the house in 2021 and 2025, a new sump pump installed in 2023, and a newly paved driveway in 2024. Electrical updates and a full foundation restoration have been completed in 2026 for long-term structural integrity (inquire for more information or see under Attached Documents), providing peace of mind for years to come. Don't miss your chance to own this move-in ready gem in a prime Chester location! See Listing Details & 43 images.
$450,000 $116 per sq.ft. Chester VT Home »
Price Change! Reduced by $25,000 down 6% on July 20th 2026
5 Beds | 4 Baths | Total Sq. Ft. 3865 | Acres: 0.44
Listed on Thursday Jun 18, 2026
Description: 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. See Listing Details & 58 images. Includes a Virtual Tour
$469,000 $193 per sq.ft. Chester VT Home »
Price Change! Reduced by $10,000 down 2% on July 6th 2026
3 Beds | 3 Baths | Total Sq. Ft. 2676 | Acres: 2
Listed on Tuesday May 5, 2026
Description: Located in the village of Chester, this 3-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! See Listing Details & 60 images. Includes a Virtual Tour
$489,000 $301 per sq.ft. Chester VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1626 | Acres: 0.33Listed on Thursday Jun 18, 2026
Description: Located in the Historic Stone Village of Chester, this thoughtfully renovated and reimagined circa 1880 home combines modern minimalist style with artisan craftsmanship. Set on .33± acres, this light-filled property features wide-pine floors, exposed beams, and a Vermont Castings woodstove anchoring an inviting open-concept living space. The kitchen/dining area showcases country cabinets with butcher block counters, attractive center island with Vermont marble counter, stainless steel sink and dishwasher framed by a wall of windows with a picturesque valley view. A spacious first-floor bedroom, full bath and convenient laundry area 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, offering peace of mind for full-time residents, second-home owners, or investors. Offered fully furnished, this turnkey Vermont property has a proven history as a successful seasonal rental. Experience the vibrant community of Chester, with its charming village shops and restaurants, town pool, recreation area, premier disc golf course, pickleball and tennis courts, snowmobile club, and thriving artisan culture. Ideally located near Okemo Mountain Resort and Magic Mountain ski areas. This quintessential Vermont home is equally suited as a primary residence, ski getaway, vacation home, or income-producing investment property. See Listing Details & 34 images. Includes a Virtual Tour
Under Contract
$495,000 $275 per sq.ft. Chester VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1800 | Acres: 2Listed on Wednesday Jun 17, 2026
Description: This well-maintained property in Chester is in close proximity to many of Vermont's best ski mountains. It is not likely that you would drive by this property without it catching your eye. From the meticulous grounds with beautiful trees to the Vermont native stone wall lining the road, to the established perennial beds to the paved driveway leading back to this pleasing home with an attached garage. This light-filled home with two floors of living (plus a multi-room lower-level walkout ready to finish) has great open space on the main level. The kitchen with updated granite counters is open to the dining area which has a sliding door to the large back deck. This is the perfect space to have dinner overlooking the landscaped back yard. Try your green thumb in the vegetable garden that is ready for planting. The living room is also connected to the dining area making this space perfect for friends and family to gather. A convenient bedroom and bathroom complete this level. Upstairs are two generous bedrooms, a bonus room for a home office or more plus space above the garage that is currently being used as an amazing walk-in closet. Come and take a look at this low-maintenance home in a park-like setting with berry bushes, fruit trees, a gazebo, and a combination garden and wood shed. The stone firepit could be a favorite spot for relaxing by the fire after a day on the slopes. There is a third bay workshop next to the attached garage and an additional detached garage that has a vent pipe for a wood stove and can be of multiple uses. This property will check boxes that you didn't even know you had! See Listing Details & 60 images.
Under Contract
$339,000 $226 per sq.ft. Chittenden VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1498 | Acres: 0.72Listed on Thursday Jun 11, 2026
Description: This quintessential Vermont retreat offers the perfect balance of mountain solitude and modern comfort, perfectly positioned for those who love the great outdoors. Step inside to a light-filled, inviting main level featuring stylish and durable vinyl plankboard flooring throughout--ideal for dropping your gear after a day of adventure. A private primary suite rests at the end of the home with a walk in closet and a luxurious soaking tub awaits to melt away the day's fatigue. Outside, the property boasts a spacious detached garage, offering plenty of room for vehicles, a workshop, or storing your skis, kayaks, and bikes. Speaking of gear, your backyard is a recreational paradise. You are just moments away from the pristine waters of the Chittenden Reservoir, a local treasure for kayaking, paddleboarding, and scenic hiking trails. When winter arrives, the world-class slopes of Pico and Killington Mountain Ski Resorts are just a twenty-minute drive from your front door, making it effortless to catch first tracks on a powder day. Conveniently located a short drive from the vibrant shops, dining, and amenities of Rutland, this home represents a rare opportunity to own a piece of the classic Vermont lifestyle. The unfinished upstairs has insulation, roughed in plumbing and electrical already installed, ready for you to customize this extra living space. If you are looking to customize a full-time residence this property is ready to welcome its next chapter. See Listing Details & 41 images.
New Listing!
$349,000 $133 per sq.ft. Chittenden VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 2620 | Acres: 66Listed on Saturday Aug 1, 2026
Description: Abutting the Green Mountain National Forest and surrounded by pristine wilderness, this executive Cape on 66 acres offers a rare opportunity to restore an exceptional Vermont estate. Custom built for its original owners in 1975, the home features a surprisingly modern floor plan with amenities still prized by today's discerning buyer, including four bedrooms, a spacious eat-in kitchen plus formal dining room, a first-floor primary suite, first-floor laundry, an elegant living room with fireplace, a comfortable family room anchored by a rustic fieldstone fireplace, an attached garage, and a full basement. Step onto the expansive rear deck and you'll discover the property's greatest treasure - sweeping panoramic views across an unspoiled landscape that inspire in every season. Whether you envision a private country estate, family retreat, or legacy property, the setting simply cannot be replicated. The home will likely require a comprehensive renovation, but its generous proportions, thoughtful design, and solid bones provide an outstanding foundation for your vision. Opportunities to acquire a property of this caliber - with substantial acreage, direct access to the Green Mountain National Forest, remarkable privacy, and breathtaking views - have become increasingly scarce. Bring your imagination and craftsmanship, and transform this hidden gem into a home that will be cherished for generations to come. See Listing Details & 39 images. Includes a Virtual Tour
