You are viewing all listings Homes with 4 or more Bedrooms between $0 and $30000000 dollars.
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.
$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
Under Contract
$549,000 $223 per sq.ft. Chester VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 2464 | Acres: 2.13Listed on Wednesday Apr 29, 2026
Description: 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. See Listing Details & 47 images.
$789,000 $215 per sq.ft. Chester VT Home »
Price Change! Reduced by $60,000 down 8% on July 24th 2026
5 Beds | 3 Baths | Total Sq. Ft. 4388 | Acres: 11.24
Listed on Wednesday Jul 1, 2026
Description: Exceptional design, enduring craftsmanship, and an unrivaled Vermont setting define this remarkable custom residence on 11± beautifully landscaped acres just a short stroll from the village of Chester. Offering more than 3,600 square feet of thoughtfully designed living space, the home was built to an exacting standard where quality materials, timeless architecture, and exceptional attention to detail create a residence as enduring as it is beautiful. A flexible floor plan offers five bedrooms and three baths, including an elegant first-floor primary suite with ensuite bath, complemented by additional main-level bedroom options ideal for guests, multi-generational living, or a dedicated home office. Upstairs, two spacious bedrooms each feature adjoining bonus rooms perfectly suited as executive offices, dressing rooms, studios, or generous walk-in closets, while additional unfinished space presents exciting opportunities for future expansion. Designed for effortless entertaining and comfortable everyday living, the heart of the home is an open-concept kitchen, dining, and living area filled with natural light. A handsome library offers a quiet retreat, while integrated whole-home audio enhances the experience throughout. An oversized laundry and mudroom connects seamlessly to the attached two-car garage, delivering exceptional convenience without compromising design. Outside, mature gardens, specimen trees, and thoughtfully curated outdoor living spaces create a setting of remarkable beauty and privacy. Relax beneath the covered porch, entertain with family and friends, or simply enjoy the peaceful surroundings. Ideally located just minutes from Okemo, Stratton, Magic, and endless four-season recreation, yet within walking distance of Chester's vibrant village, this exceptional property offers a rare combination of privacy, convenience, and refined Vermont living. A home of lasting quality, exceptional versatility, and unmistakable character! See Listing Details & 44 images.
$925,000 $325 per sq.ft. Chester VT Home »
5 Beds | 3 Baths | Total Sq. Ft. 2850 | Acres: 14.1Listed on Tuesday Jul 14, 2026
Description: Escape to the charm of Vermont in this spacious 5-bedroom, 3-bath country home, perfectly set amidst open meadows with a picturesque swim pond and peaceful surroundings. Designed for both everyday living and entertaining, this inviting property offers the perfect balance of rustic character and modern comfort. Step inside through the practical mudroom, where you'll be welcomed by a dramatic family room featuring soaring vaulted ceilings, a cozy wood-burning stove, and a loft overlooking the space. The heart of the original 1860's home is the open-concept living area, complete with a well-appointed kitchen, dining area, and a warm, inviting living room centered around a classic wood-burning fireplace. The main level also features a convenient half bath and a private primary suite with a ¾ bath. From the primary bath, step directly onto the back deck and unwind in the sunken hot tub while taking in the tranquil country setting. Second level, you'll find four additional bedrooms, a full bath, and a comfortable den/loft overlooking the family room, offering flexible space for guests, a home office, or recreation. Outside, enjoy Vermont's beauty from the private covered porch, gather around the expansive yard, or relax by the stone firepit or scenic pond surrounded by open meadows. An attached garage provides ample storage, while the finished game room above creates the perfect space for entertaining, hobbies, or additional guest accommodations. The flat meadows were the perfect setting for the family's recent wedding... What event will you host in this incredible backyard? Ideally located just minutes from the charming village of Chester and within easy reach of Okemo Mountain Resort, this exceptional property offers year-round enjoyment, whether you're seeking a full-time residence, a vacation getaway, or an investment opportunity. Visit the Okemo real estate community today. Taxes are based on town assessment. See Listing Details & 58 images.
$1,200,000 $363 per sq.ft. Chester VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 3308 | Acres: 7.8Listed on Monday May 11, 2026
Description: 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. See Listing Details & 39 images. Includes a Virtual Tour
$1,490,000 $276 per sq.ft. Chester VT Home »
5 Beds | 5 Baths | Total Sq. Ft. 5400 | Acres: 18Listed on Friday May 8, 2026
Description: Set on 18 private acres, Popple Dungeon is a distinctive Vermont property offering the feel of a true country retreat. Owned by one family and designed and built by its owner, the Williamsburg style reproduction Saltbox reflects a deep appreciation for traditional craftsmanship and enduring design. Inside, the home is defined by warm, handcrafted details wide plank wood floors, paneled walls, layered moldings, and reclaimed beams create a sense of comfort and authenticity throughout. The scale and layout offer a balance of inviting gathering spaces and quieter rooms, well suited for both everyday living and hosting. Originally operated as a bed and breakfast, the home was thoughtfully designed to welcome guests while maintaining a natural flow and sense of privacy. The surrounding land provides a peaceful and private setting, with stone walls, established gardens, wildflowers, fruit trees, and a blueberry patch woven into the natural landscape. Open areas and wooded sections create a property that feels both curated and comfortably natural, offering space to explore, relax, and enjoy Vermont's changing seasons. A guest house and dedicated woodworking barn add to the property's appeal, offering flexibility for hosting, hobbies, or creative pursuits. Ideally located near the charming village of Chester, the property offers convenient access to year-round outdoor recreation, including skiing, hiking, biking, fishing, and scenic trails. Throughout the home, the builder's attention to detail is unmistakable, with thoughtfully crafted custom woodwork and timeless finishes that reflect a genuine commitment to quality and design. Quiet, private, and rooted in tradition, this is a property well suited for those seeking a classic Vermont retreat and lifestyle. See Listing Details & 53 images. Includes a Virtual Tour
$665,000 $223 per sq.ft. Chesterfield NH Home »
Price Change! Reduced by $10,000 down 2% on July 28th 2026
4 Beds | 3 Baths | Total Sq. Ft. 2984 | Acres: 1.83
Listed on Thursday Jun 25, 2026
Description: Welcome to the heart of Spofford, where small-town charm meets one of New Hampshire's most desirable lake communities. Just minutes from Spofford Lake, this classic Cape offers a lifestyle that's increasingly hard to find. Start your mornings with coffee on the balcony overlooking the lake's peaceful inlet, spend summer afternoons at the town beach, and unwind in the hot tub at day's end. A standout feature is the stunning office in the barn. Warm wood walls still carry the welcoming scent of natural timber, creating an inspiring workspace with a private balcony overlooking the lake inlet. Inside, history and modern updates blend beautifully. The eat-in kitchen features granite countertops, an island, large pantry, and access to the private deck. Enjoy a bright sunroom, curl up with a book in the library with built-in bookshelves, formal dining room with fireplace, and convenient first-floor office and half bath. Upstairs offers three bedrooms, two full baths, laundry room, walk-in attic storage, and a flexible office or fourth bedroom. The level yard is bordered by classic stone walls and includes the lot across the street with apple and pear trees plus overflow parking. Improvements include triple-pane windows, well, septic system, oil tank, mini-splits, wood stove, sunroom, updated kitchen, EV charger, and a security system. Residents enjoy access to the Spofford Lake town beach, known for its clear waters, boating, fishing, and swimming. Conveniently located just 10 minutes to Keene and 15 minutes to Brattleboro, VT, this home offers the perfect balance of peaceful lake living with easy access to shopping, dining, healthcare, and entertainment. Rich in history, full of character, and thoughtfully updated for today's lifestyle, this is more than a home--it's a place to put down roots and enjoy everything the Spofford community has to offer. Open house Fri 6/26 4-6 & Sat 6/27 1-3. See Listing Details & 59 images.
Under Contract
$888,000 $324 per sq.ft. Chesterfield NH Home »
4 Beds | 3 Baths | Total Sq. Ft. 3188 | Acres: 0.73Listed on Tuesday Jun 2, 2026
Description: A truly exceptional home offering quality craftsmanship, generous living space, and a private setting with breathtaking mountain views. Thoughtfully designed and impeccably maintained, this stunning property combines elegance, comfort, and functionality throughout. The heart of the home is a chef's dream kitchen, featuring premium stainless-steel appliances, including a Wolf range and Sub-Zero refrigerator, abundant cabinetry, and beautiful finishes. The kitchen flows seamlessly into the sun-filled great room, where gleaming hardwood floors and a cozy fireplace create a warm and inviting atmosphere for everyday living and entertaining. Step outside to the expansive deck and take in the peaceful mountain views an ideal setting for morning coffee, outdoor dining, or simply relaxing and enjoying the tranquility of your surroundings. The home offers four generously sized bedrooms, including a luxurious primary suite complete with a spacious walk-in closet and a well-appointed en-suite bath. The walkout lower level provides additional finished living space, perfect for a home office, media room, gym, or guest accommodations, along with ample storage space. An oversized garage offers plenty of room for vehicles, recreational equipment, and all your outdoor gear. Located in one of the area's most desirable neighborhoods, just minutes from beautiful Spofford Lake, this home also provides convenient access to both Brattleboro, Vermont, and Keene, New Hampshire. Enjoy nearby shopping, restaurants, healthcare facilities, cultural attractions, theaters, museums, churches, and several colleges, all within easy reach. This remarkable property offers the perfect balance of luxury, privacy, and convenience an extraordinary place to call home. See Listing Details & 60 images.
New Listing!
$975,000 $650 per sq.ft. Chesterfield NH Home »
32 Ft. of Waterfront on Lake Spofford4 Beds | 2 Baths | Total Sq. Ft. 1500 | Acres: 0.22
Listed on Tuesday Jul 28, 2026
Description: YES!!!! that's right, TWO homes on 1 Parcel. Imagine the possibilities of having 2 homes on beautiful Spofford Lake. Come see the Rustic Charm of these classic, seasonal cottages. There certainly aren't many original vacation homes left on the lake, take advantage of owning (2) of your very own. The "Lakeside Cottage" is just a few feet from the water's edge where you can walk across the sand and dip your toes in the pristine, sandy bottom, clear water. Enjoy waterfront views and easterly sunrises from your enclosed porch as you enjoy your morning coffee. The lake front cottage also offers all the necessities of a cozy kitchen, living room with stone fireplace, 3/4 bathroom and two upstairs bedrooms to re-energize for the next day's lake excitement/activities. The "Roadside Cottage" sets only a few feet behind and is equally as charming. It also has views to the lake, use it as a guest home, rental property, or extra family space. This cottage features an enclosed porch, vaulted ceilings, brick fireplace, a loft, one downstairs bedroom, 3/4 bathroom and an upstairs bedroom. Each cottage features a time capsule of history, just waiting for your family to make more memories at Spofford Lake. Brand new septic system installed 2023 servicing both homes, updated 100amp electrical services, and new retaining wall on lake front cottage. Did I mention the convenient location? Easy access from Rte91, and just minutes from major shopping, restaurants, and grocery stores and more. See you at the Lake! See Listing Details & 40 images.
$1,995,000 $359 per sq.ft. Chesterfield NH Home »
Waterfront on River Connecticut River6 Beds | 6 Baths | Total Sq. Ft. 6476 | Acres: 18.06
Listed on Monday Oct 27, 2025
Description: ***SUBSTANTIAL PRICE IMPROVEMENT! Never before lived in, this extraordinary Connecticut River estate offers a rare opportunity to own 18± private acres and 1,200± feet of pristine river frontage, complete with a sandy beach and breathtaking views. One of the last remaining undivided waterfront parcels of its kind, this newly constructed 6,400± sq ft residence blends luxury, privacy, and natural beauty in an irreplaceable setting. Designed for both everyday living and exceptional entertaining, the home features 6 bedrooms, 6.5 baths, and an accessory dwelling unit with a private entrance--ideal for multigenerational living, guests, or extended stays. Thoughtful craftsmanship is evident throughout, including 3/4" oak flooring, Marvin windows, porcelain-tiled baths, and custom cabinetry. Whether launching a boat from your shoreline, enjoying sunsets over the river, or hosting family and friends in a truly remarkable setting, this property delivers an unparalleled lifestyle rarely found in New England. A one-of-a-kind waterfront estate offering a legacy property for generations to come. A seller credit will be provided at closing for kitchen, bathroom, and closet accoutrements, offering the opportunity to personalize the finishing touches to suit your own taste and style. Competitive seller financing options available. Just 5 minutes from Brattleboro and I-91 and only 15 minutes from Keene. See Listing Details & 60 images.
$800,000 $297 per sq.ft. Chichester NH Home »
4 Beds | 3 Baths | Total Sq. Ft. 2691 | Acres: 2.17Listed on Saturday Jul 18, 2026
Description: Exceptionally maintained 4 bedroom, 3 bath home located in one of Chichester's most desirable neighborhoods, built by Cherry Hill Homes and showcasing quality craftsmanship throughout. The thoughtfully designed first-floor layout offers an open concept feel while maintaining distinct spaces, including a home office and a study that can serve as a bedroom. The eat-in kitchen features natural wood cabinetry, elegant lighting, and a walk-in pantry, creating a timeless and functional space. Hardwood flooring extends throughout the main living areas, adding warmth and character. The inviting family room, complete with a cozy gas fireplace, overlooks the pergola and in-ground pool perfect for entertaining or relaxing. The primary suite includes a private bath and walk-in closet. Two additional bedrooms and a large bonus space over the garage share a full bath. Additional highlights include second-floor laundry, a fenced backyard, a spacious two-car garage, and a utility shed. Conveniently located with easy access to Concord and offering a walkable neighborhood ideal for biking, strolling, and enjoying community living. See Listing Details & 58 images.
$879,900 $135 per sq.ft. Chichester NH Home »
5 Beds | 6 Baths | Total Sq. Ft. 6534 | Acres: 2.1Listed on Saturday May 2, 2026
Description: Premium 6,534 sq.ft. Luxury Colonial Smart-Designed as an Independent 2 Family Compound. Separated by a private front-to-back egress hallway, this architectural T- shape features two entirely autonomous, highly finished living Wings under a single roof. Zero shared living walls guarantees total acoustic privacy without structural compromise. Priced aggressively at just $135/sq.ft. compared to Chichester's $250/sq.ft. average, this estate offers massive instant equity. Ideal for high-end multi-generational living or a premium corporate home-office retreat with a pristine, zero-damage vacant secondary wing. Bring your best clean offer! It's 5 minutes to Concord, 30 minutes to Manchester, 20-30 min.to the Lakes Region attractions. and 68 minutes to Boston, MA. See Listing Details & 57 images.
