You are viewing all VT listings NH Homes between $250000 and $500000 dollars.
$429,000 $547 per sq.ft. Castleton VT Home »
Waterfront on Lake Bomoseen2 Beds | 2 Baths | Total Sq. Ft. 784 | Acres: 0.93
Listed on Thursday Feb 5, 2026
Description: Don't miss this rare opportunity to own a reasonably priced year-round lakefront property on beautiful Lake Bomoseen. This charming 2014 single wide offers 2 bedrooms and 1½ bathrooms with an open-concept living space and a 3-season porch overlooking the water--perfect for relaxing and taking in the views. Set on a level lot with approximately 190 feet of lake frontage, the property provides easy access to the lake and plenty of yard space for summer activities, gardening, kids, and pets. Enjoy year-round recreation, including boating, kayaking, paddleboarding, and swimming in the summer, and ice skating, fishing, snowmobiling, and cross-country skiing in the winter. The original camp remains on the property and offers ample storage or could be removed to create additional yard space and uninterrupted lake views. A wonderful opportunity to enjoy lake living in every season. See Listing Details & 32 images.
Under Contract
$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 & 34 images. Includes a Virtual Tour
Under Contract
$325,000 $129 per sq.ft. Cavendish VT Home »
4 Beds | 2 Baths | Total Sq. Ft. 2520 | Acres: 0.4Listed on Thursday Apr 16, 2026
Description: Terrific village home with bright, open living spaces! This property offers the perfect backdrop for sun-drenched days, featuring charming gingerbread trim and a unique, versatile room above the porch. As you enter through the welcoming sunroom, you'll immediately enjoy the airy, open layout that connects the sunroom, dining room, and kitchen--perfect for breezy, seasonal gatherings. The first floor provides great flexibility with a comfortable living room, a family room with convenient laundry hookups, a workshop, a bedroom, and a three-quarter bathroom. Whether you're looking for single-floor living or extra space for guests, this home adapts to your needs. The second floor features two guest bedrooms, a three-quarter bathroom, and a spacious primary bedroom with a walk-in closet. If you need even more room to grow, both walk-up attics are ready to be transformed into bright studio or hobby spaces. When you're ready to enjoy the beautiful Vermont weather, step outside to the expansive, partially fenced yard. It is the ideal setting for gardening, hosting lawn games, or relaxing on the patio for al fresco dining during long, warm summer evenings. The property also includes a two-story barn, providing plenty of storage for bikes, kayaks, and all your outdoor gear. Located in the heart of Cavendish, you'll be just moments away from local favorites like Singleton's Store and the Vermont Apple Pie Bakery. With summer recreation in mind, you are only 6-8 miles from world-class golf courses, pristine lakes for swimming and boating, and the scenic trails surrounding Okemo. Schedule a showing today to see how this charming village home can be your perfect summer retreat! See Listing Details & 50 images.
$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 & 42 images.
$390,000 $197 per sq.ft. Cavendish VT Home »
Price Change! Reduced by $25,000 down 6% on March 16th 2026
5 Beds | 3 Baths | Total Sq. Ft. 1976 | Acres: 0.4
Listed on Tuesday Oct 21, 2025
Description: Welcome to this charming home nestled in a small neighborhood along the scenic Black River in Cavendish, Vermont. This inviting property combines classic Vermont character with versatile living spaces, all within walking distance of the town green, shops, restaurants, and more. Step inside through the mudroom. The kitchen offers a warm, welcoming space with a sunny dining area perfect for morning coffee or casual meals. A formal dining room provides space for larger gatherings, while the living room, bathed in morning light, creates a cozy setting to relax and unwind. A first-floor bedroom adds convenience and flexibility for guests or main-level living. Upstairs, you'll find three additional bedrooms and a full bathroom, providing plenty of room for family or friends. The property also includes an attached two-car garage and a studio apartment -- ideal for guests, rental income, or a private home office. The studio features a full kitchen and dining area, a full bathroom, and a comfortable sleeping space. Enjoy life along the river with easy access to outdoor recreation, and the charm of a small Vermont village right outside your door. This Cavendish home is a wonderful opportunity to experience the best of Vermont living -- convenient, comfortable, and full of character. Visit the Okemo real estate community today. Taxes are based on current town assessment. See Listing Details & 58 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
$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.
New Listing!
$270,000 $263 per sq.ft. Chester VT Home »
2 Beds | 1 Baths | Total Sq. Ft. 1026 | Acres: 0.32Listed on Wednesday Apr 29, 2026
Description: Not your cookie cutter home, this charming 2 BR home is located on the outskirts of Chester. One floor living for those wanting an easy keeper and carefree living. Hardwood floors throughout, large living room, formal dining room, galley kitchen and 2 roomy bedrooms. And let's not forget the spacious breezeway/entry. This area is perfect for hosting a gathering of friends and neighbors under shade or away from summer rains. Current owners have spent three years developing extensive perennial beds ensuring that there is always a flower in bloom. Along with perennials, owners have added lots of specialty trees-hardwood and fruit trees and bushes along with raised and in-ground beds and a new garden shed to store your tools. All this and there is still lawn to play on. See Listing Details & 37 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.
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 $235 per sq.ft. Chester VT Home »
Price Change! Reduced by $50,000 down 14% on March 19th 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 & 29 images.
Under Contract
$359,900 $224 per sq.ft. Chester VT Home »
Price Change! Reduced by $65,100 down 18% on March 19th 2026
3 Beds | 1 Baths | Total Sq. Ft. 1608 | Acres: 0.25
Listed on Wednesday Nov 26, 2025
Description: Welcome to this delightful 3-bedroom, 1-bath home nestled in the picturesque village of Chester, Vermont. Perfectly situated within walking distance to local shops, schools, and restaurants, this property offers the ideal blend of convenience and small-town charm. Step inside to find a spacious mudroom and laundry area -- a practical entryway for Vermont living. The open kitchen and dining area provide plenty of room for gatherings, while the cozy living room invites relaxation after a long day. A full bathroom completes the main level for easy accessibility. Upstairs, you'll find three comfortable bedrooms filled with natural light. The attached back barn offers exciting potential for additional living space, a workshop, or studio. Outside, enjoy your private fenced backyard with garden space, a fire pit, and even a bar area -- perfect for entertaining family and friends. This inviting village home combines charm, functionality, and opportunity -- come experience all that Chester has to offer! Visit the Okemo real estate community today. Taxes are based on current town assessment. See Listing Details & 53 images.
New Listing!
$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.
$399,000 $223 per sq.ft. Chester VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1788 | Acres: 3.3Listed 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.
