$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
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 MLS Property & Listing Details & 44 images.

$900,000 $321 per sq.ft. Chester VT Home »

Price Change! Reduced by $25,000 down 3% on August 13th 2026
5 Beds | 3 Baths |   Total Sq. Ft. 2800  |  Acres: 14.1
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 MLS Property & Listing Details & 58 images.

$1,200,000 $363 per sq.ft. Chester VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 3308  |  Acres: 7.8
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 MLS Property & 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: 18
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 MLS Property & Listing Details & 53 images. Includes a Virtual Tour

$629,000 $293 per sq.ft. Chesterfield NH Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2147  |  Acres: 7.5
Thursday Aug 27, 2026
Description: Open houses Sat and Sunday pm. Located conveniently between Brattleboro and Keene, this unique 4 bedroom contemporary home has been lovingly remodeled with quality upgrades while preserving its original charm. Enter through an airy enclosed porch/mudroom into a beautifully updated kitchen featuring a Wolf dual fuel professional range, large pantry, custom counters with breakfast bar, tile backsplash, and cherry hardwood floors that continue into the open dining and living areas. The dining room includes a custom built in bench with glass front storage cabinets. A cozy living room with propane stove complements the home's mini split heating and A/C system. The peaceful 3 season porch overlooks the side yard and is perfect for reading, relaxing, or enjoying a sunset. With a playful Seinfeld theme, the Elaine bedroom is located off the living room. Moving from the original home into the 1974 addition, you'll find a welcoming room with laundry and a custom full bath featuring a tiled shower and separate soaking tub. The large timber-frame family room offers a wood burning stove and access to a spacious two-level deck, complete with a vintage soapstone sink for outdoor entertaining. The peaceful primary bedroom, Jerry, is off the family room, with an adjoining storage room offering potential for a future ensuite bath. Upstairs, the George bedroom features charming nooks, a large built-in dresser, and a stained glass window. A small sewing room makes an ideal office. A vintage-inspired custom bath with porcelain pedestal sink separates George from the slightly quirky Kramer bedroom and its adjoining sitting room overlooking the living room below. Outside, stone walkways wind through beautiful gardens to a newer 2-car garage. Farther up the drive, a small barn has been transformed into a fabulous conditioned man-cave with heat and A/C, a wonderful gathering space for family and friends. Welcome Hill is especially known for its spectacular spring display of daffodils. See MLS Property & Listing Details & 60 images.

$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
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. See MLS Property & Listing Details & 60 images.

$888,000 $324 per sq.ft. Chesterfield NH Home »

4 Beds | 3 Baths |   Total Sq. Ft. 3188  |  Acres: 0.73
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 MLS Property & Listing Details & 60 images.

$899,000 $599 per sq.ft. Chesterfield NH Home »

Price Change! Reduced by $76,000 down 8% on August 22nd 2026
32 Ft. of Waterfront on Lake Spofford
4 Beds | 2 Baths |   Total Sq. Ft. 1500  |  Acres: 0.22
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 MLS Property & Listing Details & 40 images.

$800,000 $297 per sq.ft. Chichester NH Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2691  |  Acres: 2.17
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 MLS Property & Listing Details & 58 images.

$850,000 $130 per sq.ft. Chichester NH Home »

5 Beds | 6 Baths |   Total Sq. Ft. 6534  |  Acres: 2.1
Thursday Aug 13, 2026
Description: Rare opportunity to own a spacious, fully remodeled two-family compound offering 6,534 finished sq. ft. of flexible living space in the heart of Chichester! Unlike a traditional duplex, this thoughtfully designed T-shaped layout connects the two residences through a central hallway, creating zero shared living walls for exceptional privacy and sound separation. Each two-story residence offers generous living space, making this property ideal for multi-generational living, owner-occupants seeking rental income, corporate housing, or investors looking for a unique income-producing property. The home is delivered vacant, giving the new owner the flexibility to occupy, lease, or customize to fit their needs. Recent updates include a brand-new roof, updated heating systems, new kitchen sink, stainless steel range,granite countertops in the primary bath, updated lighting, and numerous plumbing improvements. The property is serviced by private septic, a shared private well,separate furnaces, and 200-amp electrical service, offering convenience and functionality for both residences. Need even more space? The 3,466 sq. ft. walkout lower level provides incredible potential for storage, workshop space, or future expansion (subject to local approvals). Conveniently located just 5 minutes to Concord, 30 minutes to Manchester, 20-30 minutes to the Lakes Region, and approximately 68 minutes to Boston, this one-of-a-kind property combines privacy, versatility, and outstanding value in a prime commuter location. OPEN HOUSE Saturday 8/15 from 11 AM to 12:30 PM. See MLS Property & Listing Details & 59 images.

$579,000 $229 per sq.ft. Chittenden VT Home »

Price Change! Reduced by $80,000 down 14% on August 26th 2026
Waterfront on River East Creek
4 Beds | 2 Baths |   Total Sq. Ft. 2532  |  Acres: 1.2
Thursday Jun 18, 2026
Description: Must see, new price! Welcome to 275 Chittenden Road, a classic Vermont Farmhouse fully refinished set on 1.2 level acres with frontage along East Creek. Offering 4 bedrooms, 2 full baths, and 2,532 finished square feet, this 1850 home blends historic charm with warm, updated living spaces and flexible options for today's lifestyle. This fully remodeled home from the studs must be seen in person to fully enjoy. Featuring exposed beams, refinished wide plank wood flooring, tiling in the kitchen and all baths no detail was missed. The additional rec room with vaulted ceilings offers the space for all of your entertaining needs. The kitchen is well appointed with marble countertops and attached dining. Step onto the screened in seasonal porch to enjoy the sound of the East Creek rolling by. Enjoy single level living with a bedroom, bath and laundry on the main floor. The property also includes a versatile accessory unit with one bedroom, its own kitchen, and a living room, offering excellent flexibility for guests, extended household needs, a private work-from-home setup, or other uses subject to local approvals. Outdoor living is just as inviting, with a covered porch, screened porch, open yard space, and the sights and sounds of the creek. Located in scenic Chittenden, Vermont, this Rutland County setting is known for its peaceful rural character and access to year-round recreation. Enjoy proximity to hiking, fishing, snowshoeing, within 30 minutes of skiing, Chittenden Reservoir, Chittenden Brook, and the broader Green Mountain region, while still having local conveniences and nearby Rutland-area amenities within reach. This home has it all, nice finishes, low maintenance with heating systems and electrical all updated, beautiful landscaping, porches and decks to enjoy, a beautiful flowing creek in the back yard and flexibility in living accommodations. The property is offered fully furnished less a few personal items. This is a must see to fully appreciate! See MLS Property & Listing Details & 60 images. Includes a Virtual Tour

$275,000 $162 per sq.ft. Claremont NH Home »

4 Beds | 1 Baths |   Total Sq. Ft. 1701  |  Acres: 0.19
Thursday Jul 30, 2026
Description: Spacious and well-maintained 4-bedroom, 1-bath home with a 1-car garage in the heart of Claremont. This charming home features an updated kitchen and full bath, beautiful hardwood floors, and two main-level bedrooms for added convenience. Upstairs, both bedrooms offer large walk-in closets. Recent updates include wood stove, updated appliances, countertops, renovated bathroom, water heater, and a Roth oil tank. Conveniently located near shopping, restaurants, local amenities, and riding trails, this move-in-ready home offers comfort, character, and convenience. Open House 8/7/2026 at 5-7pm See MLS Property & Listing Details & 28 images.

$289,000 $156 per sq.ft. Claremont NH Home »

4 Beds | 1 Baths |   Total Sq. Ft. 1850  |  Acres: 1.04
Wednesday Aug 12, 2026
Description: OPEN HOUSE August 22nd 11:30AM - 1:00PM. Showings start August 20th. INTERIOR PICTURE ON MONDAY 17TH. Welcome home to this charming property featuring numerous updates while maintaining its timeless character, nestled in a sought-after neighborhood. The updated kitchen features durable vinyl flooring and newer appliances, creating a functional and inviting space for everyday living. Beautiful hardwood floors add warmth throughout much of the home, while oversized living room windows fill the space with abundant natural light. Cozy up on cooler days with pellet stoves in both the living room and dining room. The first floor offers the convenience of a remodeled full bathroom with laundry and two bedrooms, making single-level living a possibility. Upstairs, you'll find two additional bedrooms with charming sloped ceilings, ideal for children or a home office. Situated on 1.04± acres, the outdoor space is just as appealing with established perennial gardens, a storage shed, and a metal roof. Whether you're looking for comfort, convenience, or room to enjoy nature, this well-maintained home offers it all and is ready for its next owners to make it their own. See MLS Property & Listing Details & 26 images.

$320,000 $277 per sq.ft. Claremont NH Home »

Price Change! Reduced by $25,000 down 8% on August 13th 2026
4 Beds | 2 Baths |   Total Sq. Ft. 2088  |  Acres: 0.3
Wednesday May 13, 2026
Description: OPEN HOUSE AUGUST 22nd @ 2pm-3:30pm. NEW PRICE ADJUSTMENT!! Come check out this beautifully 4-bedroom, 2-bath ranch located on a corner lot in a neighborhood setting. The previous owner completed a full kitchen remodel featuring KraftMaid cabinets, stainless steel appliances, tile flooring, newer windows, and updated light fixtures. This lovely home offers a bright living room with a large window allowing for abundant natural light, along with built-in shelving and cabinets for added charm and functionality. The main level also includes a full bathroom, hallway closet, and three bedrooms with wood flooring. The fully finished lower level was also remodeled by the previous owner and features a spacious family room with walk-out access to a composite deck, an additional bedroom with a stylish shiplap accent wall, walk-in closet, half bath with laundry, and additional closet space. Additional features include an attached garage and attached shed for extra storage. See MLS Property & Listing Details & 26 images.

$340,000 $127 per sq.ft. Claremont NH Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2673  |  Acres: 0.12
Wednesday May 20, 2026
Description: Don't miss this opportunity to own a spacious and well maintained home offering over 2,600 square feet of living space on a desirable corner lot in Claremont. Inside, you'll find 4 generously sized bedrooms, 2 full bathrooms, and a beautifully updated kitchen featuring stainless steel appliances, ample cabinetry, and a center island that's perfect for meal preparation and entertaining. The home's flexible floor plan offers multiple living and gathering spaces to accommodate today's lifestyle, whether you're hosting family and friends, working from home, or simply enjoying everyday living. Outside, relax on the covered front or side porch, entertain in the fully fenced backyard, or take advantage of the additional storage and outdoor space this property provides. Conveniently located just minutes from downtown Claremont, shopping, restaurants, schools, parks, and major commuting routes to the Upper Valley and Vermont, this home combines classic New England charm with modern updates and exceptional value. Schedule your private showing today and see everything this inviting property has to offer. See MLS Property & Listing Details & 28 images.