You are viewing all VT listings NH Homes between $250000 and $500000 dollars.
Under Contract
$260,000 $208 per sq.ft. Cavendish VT Home »
3 Beds | 1 Baths | Total Sq. Ft. 1248 | Acres: 1.6Listed on Thursday May 28, 2026
Description: Welcome to 50 Bates Rd, a charming 1920s Vermont farmhouse perched above the village of Cavendish, offering a country setting with the convenience of being in town. The standout feature is the large covered porch -- the kind of welcoming outdoor space that feels from another era and invites you to slow down and take in the setting. This home is ready for updating, but the character is already here: original hardwood floors, a country kitchen, beautiful doors, classic woodwork, period lighting, and built-ins that add both charm and practical storage. Some of the less glamorous but important improvements are already underway, including a new furnace and water heater, allowing the next owner to focus on the more enjoyable parts of renovation and design. The property also offers space for future perennial gardens and a setting with a sense of local history. Just a short drive to Okemo Mountain Resort, area restaurants, shops, and recreation, this is a wonderful opportunity to restore a home with soul in a great village location. Visit the Okemo real estate community today. Taxes are based on town assessment. See Listing Details & 52 images.
$289,000 $235 per sq.ft. Village of Proctorsville in Town of Cavendish VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1232 | Acres: 0.26Listed on Thursday Jul 10, 2025
Description: This property must be seen in person to be appreciated. Very clean and move-in ready Vermont 3-bedroom, 2-bath home just minutes from Okemo Mountain Resort in Proctorsville Village. Ideal as a low-maintenance vacation retreat or full-time residence, this well-kept home on .26± acres features a new roof and combines comfort and convenience in one of the most desirable areas of the Okemo Valley. Enjoy a spacious living room and bright eat-in kitchen with breakfast nook, and a wonderful enclosed breezeway--the perfect spot to relax or entertain in 3 seasons. The living room offers generous space with picture windows creating plenty of light. The second floor spacious, primary bedroom is equipped with many outlets for charging devices. Two additional bedrooms and a 3/4 bath complete the second floor. House re-built in 70's. The two-car attached garage provides workshop and storage space off the paved driveway. A very neat, clean and dry basement with up newer oil tank, Thermopride furnace and bulkhead doors that open to the breezeway. Enjoy mountain views and a deep yard with space for gardening and winter fun tubing or sledding. Walk to Proctorsville Village for local dining, Singleton's General Store, or the elementary school. Whether you're hitting the slopes at Okemo, golfing at Fox Run Golf Course, or simply enjoying Vermont's four-season beauty, this is rare opportunity to own an affordable home in one of Southern Vermont's most popular destinations. Motivated sellers encouraging offers. See Listing Details & 33 images. Includes a Virtual Tour
$325,000 $192 per sq.ft. Cavendish VT Home »
4 Beds | 2 Baths | Total Sq. Ft. 1696 | Acres: 0.22Listed on Friday Jan 30, 2026
Description: Opportunity meets flexibility at this charming two-unit property in the heart of Proctorsville. Ideal for an owner who wants a vacation getaway with built-in income potential -- or as an easy, turnkey investment -- this well-kept duplex offers multiple paths to ownership. The downstairs unit features a three-season porch/mudroom entry, two bedrooms, an open-concept living, dining area, and kitchen, a full bath, and a dedicated laundry/storage room. It comes partially furnished and currently has a lease in place, providing immediate income. Upstairs, the second unit offers two bedrooms, a comfortable open living and dining room or home office, an eat-in kitchen, a full bath, a large three-seasons porch, and a private deck overlooking open meadow views. The upper unit is vacant and ready for personal use or rental. The location is unbeatable -- walk to shops, dining, and village amenities in Proctorsville, and enjoy being less than 10 minutes to Okemo Mountain. A rare opportunity to combine lifestyle and investment in one property. Visit the Okemo real estate community today. Taxes are based on the town assessment. See Listing Details & 44 images.
$495,000 $215 per sq.ft. Village of Proctorsville in Town of Cavendish VT Home »
4 Beds | 4 Baths | Total Sq. Ft. 3356 | Acres: 0.15Listed on Friday May 22, 2026
Description: If you're looking for the ultime village ski house look no more! This four bedroom three and a half bath TURN KEY home is nestled in the village of Proctorsville. Home to Singletons Store, Outer Limits Brewery, Murdoch's On The Green and much more walking distance away. Step into this lovely well appointed home and you'll feel right at home. The kitchen boasts granite counters with a large breakfast bar. Oak cabinetry, mostly stainless steel appliances, tile backsplash and under counter lighting. You'll love the open concept of the kitchen and dining room, with a granite two sided fireplace. Mozie on into the large living room with space for the whole crew and cozy up to the other side of the fireplace. The first floor is completed with an en-suite bedroom with a beautiful view of Hawks Mountain, the bathroom is finished with a tiled shower and a natural wood vanity. Rounding off the main floor with a half bath laundry room combo and a convenient corner nook for gear storage. Upstairs you find another en-suite bedroom with double sink, natural wood vanity and tiled shower. The two other large bedrooms share a full bath. One bedroom with a balcony overlooking Hawks Mountain State Forest which is a healthy walk away for recreating. Now down the the lower level where the fun begins. Pool table, foosball or a game of cards, pick your favorite. This Ultimate Village Ski House is priced to sell! Come take a look today! See Listing Details & 59 images.
Under Contract
$315,000 $136 per sq.ft. Chelsea VT Home »
Waterfront on River First Branch White River4 Beds | 1 Baths | Total Sq. Ft. 2322 | Acres: 1.03
Listed on Tuesday Feb 10, 2026
Description: Step into timeless New England charm with this beautifully maintained farmhouse, perfectly set in the heart of a quaint small town. Rich wide pine floors and classic details create a warm, welcoming feel. The home offers 4 nicely sized bedrooms, one conveniently located on the main floor across from the full bathroom. Upstairs you'll find the primary and two additional bedrooms. Each with ample walk in closet space. A dedicated office--ideal for remote work or creative pursuits sits just off the large dining room and kitchen. Step out onto the covered front porch to enjoy a morning cup of coffee or a cozy afternoon read. Lovingly cared for over the years, this home blends historic character with move in ready comfort. Outside, you'll find a one-car garage, versatile attached workshop space, and a level riverfront lawn that invites relaxing afternoons by the water. Established garden areas provide the perfect setting for those with a green thumb or dreams of farm-to-table living. Your next chapter starts with this truly special property! See Listing Details & 54 images.
Under Contract
$325,000 $146 per sq.ft. Chelsea VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 2230 | Acres: 1.06Listed on Monday May 4, 2026
Description: Nestled in the heart of the historic Chelsea District, this beautifully maintained 1850 Colonial offers the perfect blend of timeless charm and modern comfort. Step onto the inviting front porch and into the foyer that welcomes you with traditional grace. On the first level, you'll find a thoughtfully laid-out kitchen with ample cabinetry, a formal dining room, a study featuring built-in storage for a library or personal decor, and a double sized living room all with large windows that bathe the spaces in natural light. Upstairs, all three bedrooms are generously sized, and the over-sized full bathroom includes a large linen closet and laundry hook-ups for convenience. The primary suite boasts an additional office or seating area, ideal for remote work or a cozy reading nook. Completing the property is additional storage or workshop space, attached to the back of the house, and lastly on the third floor is a very large walk-up attic. This classic Chelsea home is a rare opportunity to own a piece of Vermont history, just steps from local amenities and attractions. A few doors down is the Free Verse Farm Shop which is a quaint community-centered general store with alfresco seating. It's a great place to dine from their daily menu or simply enjoy a tea or coffee outside. The Free Verse Farm shop supports local farmers, artisans, and features a full selection of herbs and apothecary products. Once you step inside, you'll fall in love with the ambiance of old world America. See Listing Details & 60 images.
$349,000 $163 per sq.ft. Chelsea VT Home »
4 Beds | 2 Baths | Total Sq. Ft. 2142 | Acres: 0.6Listed on Monday Jun 1, 2026
Description: Rich in character and timeless appeal, this classic home offers the perfect blend of historic charm, flexible living space, and modern convenience. Situated on a level 0.60-acre in-town lot, the property provides a spacious setting with easy access to local amenities, schools, and community services. A welcoming covered front porch invites you inside, where you'll find bright, comfortable living spaces filled with natural light and classic architectural charm. The home's thoughtful layout offers inviting gathering areas, including a spacious living room and dining area ideal for everyday living and entertaining. The flexible floor plan includes three bedrooms on the second level, along with a main-level bedroom and full bath. A thoughtfully designed first-floor addition features a spacious bonus room and handicap-accessible ¾ bath, offering excellent options for guests, multi-generational living, or convenient single-level living. A lovely rear deck extends the living space outdoors and offers the perfect spot for morning coffee, summer cookouts, or relaxing while overlooking the backyard. Adding to the property's appeal is an impressive three-bay garage with an attached workshop, offering abundant space for vehicles, equipment, hobbies, storage, or projects. Whether you're a craftsman, collector, or simply need extra room to spread out, this versatile space is sure to impress. A true piece of American architectural history, this home was originally built as a Sears Roebuck kit home known as "The Kilbourne." Celebrated for their quality craftsmanship and innovative design, Sears homes remain highly sought after today. Distinctive architectural features--including dormer windows, built-in cabinetry, wide overhangs, and classic bungalow detailing--enhance the home's character while providing lasting curb appeal. Rich in charm and full of potential, this property offers the perfect opportunity to enjoy historic style with modern possibilities. See Listing Details & 43 images.
Under Contract
$250,000 $219 per sq.ft. Chester VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1140 | Acres: 0.25Listed on Wednesday May 13, 2026
Description: There's something quietly reassuring about a home that's stood the test of time--and this classic dormered Cape in Chester delivers just that, with a clean, updated feel that suits today's lifestyle. Built circa 1945, the home offers three comfortable bedrooms--including a convenient ground-floor bedroom--and 1.5 baths, giving you flexibility for guests or single-level living. The layout is practical and easy to live in, and the enclosed rear entry porch adds everyday function--perfect for muddy boots, groceries, or easing into the house after a long Vermont day. Out back, the porch doubles as a relaxed hangout space, or step out onto the sun-filled deck for a bit more light and fresh air. It's an easy, inviting setup for morning coffee or winding down at the end of the day. Downstairs, a full basement provides solid storage or workspace potential, while the detached two-car garage--with workshop space and automatic openers--offers flexibility for projects, hobbies, or extra gear. The paved driveway, standing seam metal roof, and straightforward systems like the oil-fired hot water setup all point toward low-maintenance ownership--something buyers appreciate more and more. The home is being offered with key appliances already in place, including an electric range, refrigerator, microwave, washer, dryer, and dehumidifier, making for an easy transition whether you're just starting out or simplifying your next chapter. Set in one of Southern Vermont's most loved villages, this is the kind of property that works just as well as a first home as it does for downsizing. Simple, solid, and well-located--if Chester's been on your radar, this one's worth a closer look before it slips by. See Listing Details & 20 images.
Under Contract
$269,000 $230 per sq.ft. Chester VT Home »
3 Beds | 1 Baths | Total Sq. Ft. 1168 | Acres: 0.5Listed on Monday Apr 6, 2026
Description: This cozy gambrel style home tucked away on a nice level 1/2-acre lot just on the outskirts of Chester village offers lots of yard space, lots of storage space and is an easy keeper. This cute home offers hardwood floors on the first floor, has lots of natural light, an enclosed porch that could work as a home office, dining area, mud room or just a place to hang out. 2nd floor features three bedrooms with the primary leading out to a deck overlooking the yard. Nice high ceilings on the second floor make the rooms very open and bright. There's an attached storage room allowing room for freezers, storage or a second mud/entry room. Large 2 bay garage with second floor storage, a side shed that would be perfect for a garden shed and a separate space for lawn and snow blowers. The owners have done lots of upgrades, including a full house generator. So, if you are looking, be sure to add this home to your list. See Listing Details & 34 images.
$289,000 $196 per sq.ft. Chester VT Home »
2 Beds | 3 Baths | Total Sq. Ft. 1475 | Acres: 9Listed on Tuesday Nov 18, 2025
Description: Sweet! An just in time for the holidays. This cabin has been lived in year round and has a drilled well, septic and electric. The basement has been partially finished with the fixtures of a 3/4 bath but no wall coverings, so the square footage is not counted here. The tenant does not have internet so it is best to check on phone/tv and internet from the providers. The property is being divided from the parcel across the street and they may be purchased together. See MLS #5069927 This is a nice level to rolling lot with some open and some woods, has a 2 car garage, 2 enclosed porches and is well put together inside. The outside needs some finish work, so not likely to go a federal program. With some TLC this will be a fab get away. The town maintains the road to the house...such a benefit! This is a must see for location See Listing Details & 14 images.
$299,000 $201 per sq.ft. Chester VT Home »
Price Change! Reduced by $100,000 down 33% on June 2nd 2026
3 Beds | 2 Baths | Total Sq. Ft. 1488 | Acres: 0.25
Listed on Saturday Sep 13, 2025
Description: Welcome to your dream home - This meticulously maintained and efficient New England-style gem is bursting with charm and modern convenience. Extra insulation, new windows and new hot water heater make this home as energy-efficient as it is beautiful. Picture yourself whipping up meals in a kitchen with custom Hugh Pennell solid wood cabinets, upgraded appliances and solid countertops. Be wowed by the gorgeous hardwood floors that add warmth and character to every room. Bask in the great natural light that fills every corner of this lovely abode, making every day feel bright and inviting. This home includes a main level bedroom, dining room and family room. In addition there is an attached garage and a barn for all your hobbies. This home is perfect for families and outdoor enthusiasts alike. Imagine being just a short stroll away from the village store for all your essentials and enjoying nearby skiing adventures in winter, along with shopping and restaurants year-round! Don't miss out on this incredible opportunity to own a piece of paradise in the heart of it all! Schedule your visit today and get ready to fall in love - your perfect home awaits! See Listing Details & 30 images.
$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.
Under Contract
$340,000 $162 per sq.ft. Chester VT Home »
3 Beds | 1 Baths | Total Sq. Ft. 2096 | Acres: 1.69Listed on Friday Mar 20, 2026
Description: Welcome to a charming village retreat in the heart of Chester, perfectly situated on Main Street in the historic Chester Stone Village. This inviting home blends classic Vermont character with comfortable, year-round living. Enter through a practical mudroom with ample space for all your seasonal gear--ideal for embracing Vermont's four-season lifestyle. To the right, at the front of the home, you'll find a bright and open living space featuring a spacious kitchen with a large island, seamlessly connected to the dining area and living room. A glass door leads to a covered porch, creating the perfect spot for morning coffee or relaxing evenings. The main level also offers a dedicated office, a full bathroom, and a convenient laundry room. Toward the back of the home, two bedrooms provide comfortable accommodations, and a stunning family room showcases vaulted ceilings, exposed beams, and walls of windows that fill the space with natural light. A glass slider opens to the back deck, where you'll find an above-ground pool--perfect for summer enjoyment. Experience the charm of Vermont living in this village home, just moments from local shops, dining, and all that Chester has to offer. Visit the Okemo real estate community today. Taxes are based on town assessment. See Listing Details & 55 images.
$349,000 $195 per sq.ft. Chester VT Home »
Price Change! Reduced by $100,000 down 29% on May 7th 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.
$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.
