You are viewing all listings Homes between $250000 and $500000 dollars.
$475,000 $171 per sq.ft. Charlestown NH Home »
6 Beds | 2 Baths | Total Sq. Ft. 2786 | Acres: 0.6Listed on Wednesday May 6, 2026
Description: Discover an exceptional multi-family opportunity at 52 Dell Street, ideally situated on a quiet dead-end street near the Connecticut River in Charlestown, NH. This spacious duplex offers two well appointed 3 bedroom, 1 bath units, each with separate entrances, private paved driveways, and individual garages making it an ideal option for investors, owner-occupants, or multi-generational living. Residents will appreciate the generous layouts, functional living spaces, and strong income potential. Outside, the beautifully maintained backyard features a stunning in-ground pool, creating a rare and highly desirable outdoor retreat that sets this property apart. Conveniently located near local amenities, recreation, and commuter routes, this property combines peaceful surroundings with practical convenience. Whether you're looking to expand your real estate portfolio, generate rental income, or secure a versatile residential investment, 52 Dell Street delivers outstanding value, flexibility, and lifestyle appeal in today's market. Don't miss this unique chance to own a standout duplex in the scenic Connecticut River region. See Listing Details & 35 images.
$499,000 $385 per sq.ft. Charlestown NH Home »
3 Beds | 3 Baths | Total Sq. Ft. 1297 | Acres: 0.43Listed on Thursday Feb 26, 2026
Description: Welcome to the Grove, a thoughtfully planned new construction community of energy-efficient homes set along the Connecticut River in scenic Charlestown. Built on land with a conservation-focused legacy, this neighborhood is designed to preserve a natural beauty while offering modern, comfortable living with a peaceful, rural feel. This brand-new 3-bedroom, 2.5-bath home features a bright, open-concept layout filled with natural light-perfect for everyday living and easy entertaining. The kitchen, dining and living areas flow seamlessly together, creating a warm and inviting main living space. Upstairs, you'll find three comfortable bedrooms, including spacious primary suite with a private bath. The home includes a full concrete basement offering excellent storage and future potential to finish for additional living space, a home gym or media room. A 1-car garage adds everyday convenience, while the level yard provides space to relax, garden or play. Enjoy the best of NH living with nearby walking trails and paths to the Connecticut River, ideal for peaceful strolls, outdoor recreation and soaking in the natural surroundings. Located in the scenic Sugar River Valley, you'll have easy access to Claremont, Keene and the Upper Valley while still enjoying a quiet country setting. Designed and built by Chinburg Builders, a trusted Energy Star builder for over 20 yers, these homes offer lower energy costs, enhanced comfort and quality construction verified by independent testing. The Grove delivers a rare opportunity to own a brand-new, energy-efficient home in a beautifully planned riverside community. See Listing Details & 29 images.
$499,000 $385 per sq.ft. Charlestown NH Home »
3 Beds | 3 Baths | Total Sq. Ft. 1297 | Acres: 0.44Listed on Thursday Feb 26, 2026
Description: Welcome to the Grove, a thoughtfully planned new construction community of energy-efficient homes set along the Connecticut River in scenic Charlestown. Built on land with a conservation-focused legacy, this neighborhood is designed to preserve a natural beauty while offering modern, comfortable living with a peaceful, rural feel. This brand-new 3-bedroom, 2.5-bath home features a bright, open-concept layout filled with natural light-perfect for everyday living and easy entertaining. The kitchen, dining and living areas flow seamlessly together, creating a warm and inviting main living space. Upstairs, you'll find three comfortable bedrooms, including spacious primary suite with a private bath. The home includes a full concrete basement offering excellent storage and future potential to finish for additional living space, a home gym or media room. A 1-car garage adds everyday convenience, while the level yard provides space to relax, garden or play. Enjoy the best of NH living with nearby walking trails and paths to the Connecticut River, ideal for peaceful strolls, outdoor recreation and soaking in the natural surroundings. Located in the scenic Sugar River Valley, you'll have easy access to Claremont, Keene and the Upper Valley while still enjoying a quiet country setting. Designed and built by Chinburg Builders, a trusted Energy Star builder for over 20 yers, these homes offer lower energy costs, enhanced comfort and quality construction verified by independent testing. The Grove delivers a rare opportunity to own a brand-new, energy-efficient home in a beautifully planned riverside community. See Listing Details & 36 images.
Under Contract
$349,900 $276 per sq.ft. Chatham NH Home »
Waterfront on Pond Lower Kimball Pond2 Beds | 1 Baths | Total Sq. Ft. 1268 | Acres: 0.35
Listed on Friday Jan 30, 2026
Description: This new construction features cathedral ceilings and an open floor plan, offering a bright and spacious feel. A prime short-term rental opportunity with no town restrictions, it's ideal for investors or vacation homeowners. Full-time residents enjoy access to Fryeburg Academy, Maine's oldest high school - a private school free to Chatham residents - known for rigorous academics, diverse extracurriculars, and a unique blend of local and international boarding students. The home also offers a private backyard and exceptional outdoor recreation, including a 5-minute drive to the Baldface Trailhead and Emerald Pool, a hidden gem of the White Mountain National Forest. Skiers will appreciate Pleasant Mountain, Cranmore, Attitash, and Sunday River all being within easy reach. Enjoy quick access to North Conway outlets, as well as the renowned Fryeburg Fair each fall. Final touches, like closet hardware, are waiting to be chosen. Whether you're seeking a primary residence, vacation retreat, or income-producing property, this home offers a rare combination of new construction, location, and lifestyle appeal. See Listing Details & 34 images.
Under Contract New Listing!
$285,000 $147 per sq.ft. Chelsea VT Home »
4 Beds | 2 Baths | Total Sq. Ft. 1940 | Acres: 1.28Listed on Thursday Jul 23, 2026
Description: Built in 1875, this classic Vermont home offers something that's becoming increasingly difficult to find, a beautifully preserved village property with original character, generous outdoor space, and a three stall barn. Whether you envision a workshop, hobby farm, antique car storage, creative studio, or simply a place to spread out, this property offers possibilities that extend well beyond the walls of the home. Inside, you'll discover wide pine floors, original built-ins, tall ceilings, spacious rooms, classic woodwork, and an inviting enclosed front porch perfect for morning coffee or watching the seasons change. Outside, a spacious covered porch, perennial gardens bloom throughout the property while the deep backyard and barn create an ideal setting for gardening, entertaining, or pursuing your favorite hobbies. Located in the heart of Chelsea, you'll enjoy the charm of village living while owning a true piece of Vermont history. See Listing Details & 41 images.
Under Contract
$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.
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.
