You are viewing Upper Valley Homes with 4 or more Bedrooms between $0 and $30000000 dollars.
$295,000 $148 per sq.ft. Sharon VT Home »
4 Beds | 2 Baths | Total Sq. Ft. 1992 | Acres: 10.5Listed on Wednesday Apr 1, 2026
Description: Looking to start your investment portfolio? This property is a great place to start, with opportunity to purchase two additional units that share the septic. In a quiet Sharon cul-de-sac, this property has two, two-bedroom units, one on each floor. Newer roof, newer shared septic, poured concrete foundation. Lot includes 10 acres of land that abuts land owned by the VT Dept. of Fish & Wildlife, which abuts the White River. Usability/buildability of the land to be confirmed by purchaser. PRE-INSPECTION AVAILABLE UPON REQUEST - Owner corrected a lot of the issues that were discovered at the inspection. Leaving mostly cosmetic fixes for the new owners. One unit is rented month-to-month, and one has a 12-month lease. Purchaser could potentially buy out lease, or request building vacant at closing. Owner would consider adding right of first refusal on doublewide which abuts the subject property duplex. Putting you in control of the entire septic system, with 4 rental units on one property. So much potential for an investor to build sweat equity in this property. Video tours of each unit available upon request. 48-hours notice required for showings as both units are occupied. See Listing Details & 24 images. Includes a Virtual Tour
$154,000 $68 per sq.ft. Thetford VT Home »
5 Beds | 3 Baths | Total Sq. Ft. 2280 | Acres: 0.47Listed on Saturday Apr 26, 2025
Description: Mixed-use property (two apartments and commercial or studio space) in the charming village of Post Mills. Originally single-family home, has been converted into a 3-unit building, offering a range of potential uses: fully residential or multi-family investment; single-family home; combination of both commercial and residential spaces. Grants available for exterior and interior improvements. Top Unit > the largest area, with demo already started (kitchen and bath removed) offering an opportunity to complete renovation to your specs. This unit could be transformed into a spacious 2-bedroom apartment, with potential for views of the surrounding area. The open layout gives you a blank canvas to create a stunning living space. Downstairs > Long term tenant just moved out of the 2-bedroom main level, so the space is ready for renovation and paint. Offering excellent opportunity to modernize and find your own tenant. It's ready to go! Back Unit > This small studio space is in need of work but offers potential to be a cozy, income-generating rental. With the right renovations, it could be a charming unit with its own appeal. Could also be used for small commercial rental space, as well. Basement > interior access, needs attention for storage use. See Listing Details & 4 images.
$425,000 $141 per sq.ft. Thetford VT Home »
6 Beds | 3 Baths | Total Sq. Ft. 3024 | Acres: 0.48Listed on Thursday Mar 26, 2026
Description: Versatile 3-Unit Property in Convenient Thetford Location Located along scenic and accessible Route 5 in Thetford, this well-maintained 3-unit property offers a great opportunity for investors. One unit features direct access to both garages, providing convenience and privacy, while the two additional units--each on separate levels--offer consistent rental income to help offset expenses. Recent updates include a brand-new roof, and the property boasts a history of happy, long-term tenants. With ample off-street parking, a nice level yard for outdoor enjoyment, and just a quick 20-minute commute to the Upper Valley, this is a smart investment in a highly desirable location. Whether you're looking to live in one unit and rent the others, or fully invest, this flexible property checks all the boxes. All units are currently rented See Listing Details & 19 images.
Under Contract
![Thetford VT Home for sale $689,000 $298 per sq.ft.]()
$689,000 $298 per sq.ft. Thetford VT Home »
4 Beds | 4 Baths | Total Sq. Ft. 2315 | Acres: 5.61Listed on Tuesday Mar 24, 2026
Description: Set on 5.6 private acres in East Thetford, this property was simply just "done right." With mountain views, privacy, and proximity to Upper Valley amenities, this is the full package. The home features soaring cathedral ceilings, beautiful hardwood floors, a large kitchen, and an open and inviting layout with handicap accessible doorways and spaces. The main level also offers a primary bedroom/bathroom and laundry for added convenience. With a total of 4 bedrooms, and 3.5 bathrooms, this home provides flexibility for a variety of living needs. Enjoy the balance of peaceful Vermont living with easy access to Hanover and Lebanon, NH, home to Dartmouth College and Dartmouth-Hitchcock Medical Center, along with shopping, dining, and services. Outdoor recreation abounds with nearby hiking, skiing, and river access. A rare opportunity to enjoy space, views, and convenience in a sought-after location. Showings begin Friday 3/27/26. See Listing Details & 47 images.
Under Contract
![Thetford VT Home for sale $795,000 $322 per sq.ft.]()
$795,000 $322 per sq.ft. Thetford VT Home »
4 Beds | 2 Baths | Total Sq. Ft. 2472 | Acres: 4Listed on Wednesday Apr 15, 2026
Description: Located at the end of a quiet dirt road, this beautifully crafted Classic Saltbox Style Colonial Reproduction Home features period millwork, custom cabinetry, wainscot and wide pine plank floors throughout. Oversized 8/8 sash windows fill the rooms with sunlight. Enter the mudroom with tile floor connecting the two-car garage with bonus playroom above, a private screened porch and spacious kitchen with butcher block counters and new stainless steel appliances. A lovely flow of space and light make the common areas comfortable and inviting. One bedroom, laundry and ¾ bath complete the first level. Moving upstairs there is a generous Primary Bedroom with walk in closet, two additional bedrooms, and a full bathroom with a clawfoot tub. The full basement has great potential for playroom, or workshop. Huge, private level yard for play or gardening, and an ideal pond site at the woods edge. New propane boiler. Optional Tarm wood boiler if wood heat is your preference. All systems, roof and septic are new. Easy access to the Interstate. Quick commute to DHMC and Dartmouth College. High speed EC Fiber for remote working. No drive-bys please. See Listing Details & 45 images.
$329,000 $154 per sq.ft. Windsor VT Home »
Price Change! Reduced by $10,000 down 3% on April 29th 2026
4 Beds | 2 Baths | Total Sq. Ft. 2142 | Acres: 0.25
Listed on Friday Apr 3, 2026
Description: Discover space, flexibility, and everyday convenience in this charming 4-bedroom, 2-bath home in the heart of Windsor. Thoughtfully designed with a spacious floor plan, the main living area features warm hardwood floors and abundant natural light, creating a bright and welcoming atmosphere throughout. The formal dining area flows seamlessly into the living room, perfect for both everyday living and entertaining. A main-level bedroom and full bath, along with convenient first-floor laundry, offer ideal single-level living options or guest accommodations. Upstairs, you'll find three generously sized bedrooms, providing plenty of space for family, guests, or a home office setup. Set on a quarter-acre lot, the property offers ample parking and a detached one-car garage, perfect for storage, hobbies, or a workshop. Centrally located and easy access to town, grab your morning coffee just a short walk away or head to the nearby pond for a relaxing swim. A wonderful opportunity to own a well-located home with space, charm, and versatility in Windsor! See Listing Details & 25 images.
$413,900 $143 per sq.ft. Windsor VT Home »
Price Change! Reduced by $10,100 down 2% on April 28th 2026
4 Beds | 3 Baths | Total Sq. Ft. 2888 | Acres: 1.22
Listed on Tuesday Mar 24, 2026
Description: Motivated seller! Price drop! A rare piece of Vermont history, thoughtfully preserved for modern living. Dating to 1790, this distinguished brick and frame Colonial stands as a testament to early New England craftsmanship -- and it's ready for its next chapter. Meticulously maintained over the centuries and updated where it counts, this two-story home offers the warmth of wide-plank hardwood and softwood floors, the peace of mind of updated electrical and heating systems, and the curb appeal of a classic standing seam roof and fresh paint throughout. Recent windows flood the interior with natural light while preserving the home's timeless character. Whether you're drawn by the historic details or the practical updates, this property is move-in ready from day one. The kitchen is showstopping with a seamless blend repurposed materials. It exudes character and charm. The attached 1 car garage -- complete with a dedicated storage room/workshop area and a massive open attic accessible from both levels -- offers flexible space for a workshop, studio, or expansion. A property of this age rarely offers this much functional square footage. Positioned conveniently off Exit 9, commuting to the Upper Valley and beyond is effortless. The commercial zoning potential makes this an exceptional opportunity for buyers seeking a live-work arrangement, professional office space, or a savvy investment in one of Vermont's most storied small towns. Historic character. Modern comfort. Extraordinary potential. See Listing Details & 38 images.
$395,000 $244 per sq.ft. Woodstock VT Home »
4 Beds | 2 Baths | Total Sq. Ft. 1617 | Acres: 0.65Listed on Wednesday Oct 1, 2025
Description: Classic Vermont farmhouse just minutes from the heart of Woodstock. This charming 4 bedroom , 2 bath home offers the character of a traditional New England property with comfortable , move in ready living spaces. The home features a bright eat-in kitchen, spacious dining room, and a welcoming living room with a wood-burning fireplace--perfect for cozy Vermont evenings. Freshly painted interiors and updated flooring provide a clean , inviting feel while preserving the home's classic farmhouse charm. An attached barn/ garage offers excellent storage and flexible space for outdoor gear , a workshop, or hobby area--ideal for those who enjoy Vermont's year-round outdoor lifestyle. Located just a short drive to the Village Green in Woodstock, the property also provides convenient access to hiking, biking, and skiing at nearby Killington Resort. Whether you are seeking a full time residence or a Vermont getaway , this property offers an excellent opportunity to enjoy one of Vermont's most desirable areas at an attractive price point. Call today for a private viewing. See Listing Details & 47 images.
New Listing!
![Village of Taftsville in Town of Woodstock VT Home for sale $527,000 $289 per sq.ft.]()
$527,000 $289 per sq.ft. Village of Taftsville in Town of Woodstock VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 1824 | Acres: 0.42Listed on Friday Apr 24, 2026
Description: Step into a rare offering where timeless New England charm meets contemporary comfort. Originally built in 1846 and thoughtfully reimagined, this exceptional Taftsville, Vermont residence is set along Happy Valley Brook, creating a private sanctuary defined by peace, beauty, and understated elegance. Historic character is beautifully complemented by carefully curated upgrades, including energy-efficient heat pumps, enhanced electrical systems, basement insulation, and newer windows--ensuring comfort and efficiency in every season. Recent capital improvements, such as updated siding, a newer drilled well, and new oil and propane tanks, underscore the home's turnkey reliability, while generator-ready capability provides an added layer of confidence. Enjoy a kitchen built for making memories anchored by a newly installed and sleek granite island perfect for connection and celebration. Outdoors, the revitalized grounds invite both quiet relaxation and effortless entertaining, all framed by the natural splendor of this picturesque village setting. Positioned on coveted Happy Valley Road, the property offers a lifestyle as desirable as the home itself--where morning strolls and evening bike rides become part of your daily rhythm. Just minutes from the boutiques, dining, and charm of Woodstock, as well as convenient access to Interstate 89, this location perfectly balances a charming, village-like setting with accessibility. Imagine summer evenings spent beside the gently flowing stream, gathered around a glowing fire under the stars--an experience that captures the very essence of elevated Vermont living. Showings begin at the open house on Sunday, April 26th, from 1-3pm. See Listing Details & 49 images. Includes a Virtual Tour
$675,000 $212 per sq.ft. Woodstock VT Home »
Price Change! Reduced by $14,000 down 2% on March 26th 2026
4 Beds | 3 Baths | Total Sq. Ft. 3190 | Acres: 2.94
Listed on Friday Feb 20, 2026
Description: Historic Woodstock, Vermont - Spacious Home on Nearly 3 Acres. Welcome to a rare opportunity in the heart of Woodstock, one of Vermont's most picturesque and sought-after villages. This expansive home offers generous living space with many rooms, providing flexibility for a large household, home offices, guest quarters, or the potential to create multiple apartments (buyer to verify local regulations).Inside, you'll find two charming fireplaces that add warmth and character, perfect for cozy Vermont evenings. The home's classic architecture blends timeless appeal with endless possibilities for customization. Set on over 2 acres, the property features a fenced yard ideal for pets, gardening, or outdoor entertaining. A one-car garage adds convenience, while the separate potting shed--complete with electricity and a heater--offers wonderful space for gardening enthusiasts, creative projects, or additional storage. Located just minutes from Woodstock Village, you'll enjoy easy access to boutique shopping, dining, and the renowned Woodstock Inn & Resort and its spa amenities. Vermont's natural beauty surrounds you--world-class skiing, hiking, biking, and year-round recreation make this an exceptional place to unwind, recharge, and truly enjoy life. A unique property with space, charm, and opportunity in historic Woodstock. See Listing Details & 45 images.
Under Contract
$825,000 $212 per sq.ft. Woodstock VT Home »
5 Beds | 5 Baths | Total Sq. Ft. 3886 | Acres: 2.36Listed on Saturday Sep 6, 2025
Description: NEW PRICE! This lovely,expanded Cape sits just a half mile from Woodstock Village's East End.Surrounded by rolling green fields and wooded hillsides-this home offers a beautiful country setting less than a mile to village shopping, schools, dining and recreation. Updated with modern finishes to enhance accessibility and one level living-while maintaining the warm, country charm. First floor features a kitchen with granite countertops, island with seating & storage, double pantry and all new appliances; dining room with fireplace, an all season sun room w/gas fireplace and deck access, a wonderful new laundry room with half bath, lovely primary bedroom and bath with soaking tub, tiled zero step shower(roll-in), & double sinks, & living room w/fireplace. Lots of light and warm wood floors throughout. Two bedrooms with sitting areas and lots of storage and full bath upstairs. The connected 2 bedroom apartment lends flexibility-it can be used as additional living space, overflow for guests or for extra income as a rental. Full kitchen,first floor bedroom and bath,second floor bedroom & storage loft and one car garage with second driveway, private entrance, deck and laundry.The back of the property slopes down to a babbling brook and then up to meet direct trail access to Mount Peg.Expansive deck,generator,attached two car garage & partially finished walk out basement with tons of storage, a recreation room or office and powder room too. So many possibilities! Easy to show and move-in ready! See Listing Details & 60 images.
Under Contract
$895,000 $566 per sq.ft. Woodstock VT Home »
4 Beds | 2 Baths | Total Sq. Ft. 1580 | Acres: 0.08Listed on Saturday Apr 18, 2026
Description: Beautiful residence with newer renovations...located in the heart of historic Woodstock. Sunlit rooms, open floor concept with handsome refinished original pine floors. Stunning kitchen with stainless appliances, oversized island and soapstone counters accent the new cabinetry. Large dining room for entertaining with lovely screened in porch with double doors that lead out to a privately enclosed courtyard. First floor also features a mudroom, new 1/2 bath, family room and gracious formal living room accented with bookshelves. Second floor consists of a large primary bedroom, a guest bedroom and newly renovated full bathroom and laundry room. Third level has another 2 bedrooms or could be used as offices. This residence is the south side (left side) of the building and includes new mini split a/c units, a storage shed and perennials gardens. Walk to all of towns amenities, shops and restaurants. Mt. Tom National park and hiking behind the house for those nature enthusiasts, championship golf, skiing and fly fishing near by. 20 minutes to the Upper Valley and Dartmouth. Wonderful opportunity to own this charming home in one of Vermonts prettiest towns. See Listing Details & 38 images.
$985,000 $354 per sq.ft. Woodstock VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 2785 | Acres: 5.01Listed on Monday Jul 21, 2025
Description: This early Woodstock residence was built in 1792 by Joseph Wood on a parcel of land he purchased in 1786 from Ebenezer Kingsley, one of Woodstock early settlers. A classic New England Cape of the period with the notable features of a central chimney with multiple fireplaces and a second story overhang on the gables. The house retains a great deal of original features and fabric including wide board flooring, horizontal wainscotting, period doors and hardware and a keeping room fireplace. Massive exposed beams substantiate the date of construction. The four bedrooms and three baths include a first floor primary en suite bedroom. Spacious rooms with unusually high ceilings and multi pane windows create a comfortable living space. Beautifully sited and located on the exclusive Randall Road within a grove of ancient sugar maples. See Listing Details & 37 images.
Under Contract
$1,195,000 $448 per sq.ft. Woodstock VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 2668 | Acres: 8.32Listed on Wednesday Feb 18, 2026
Description: Set on a sun-bathed hillside between Woodstock Village and the renowned slopes of Killington and Pico, this custom-built Colonial captures what buyers seek most in Vermont: privacy, craftsmanship, and striking mountain views that feel close enough to touch. Thoughtfully designed by the respected Vermont Vernacular Builders, the home reflects classic regional architecture with refined proportions, timeless materials, and an effortless sense of place. The interior is bright, welcoming, and designed for both everyday living and memorable gatherings. Wide board floors run throughout, while exposed beams lend texture and authenticity to the inviting den and spacious eat-in kitchen. A butler's pantry provides exceptional storage and service flow to the formal dining room, and multiple living spaces -- including a fireplaced living room with gas insert and a den warmed by a wood stove -- offer comfortable options for relaxing or entertaining in every season. Positioned on more than eight private acres, the setting feels peaceful and secluded, yet remains remarkably convenient: Woodstock's celebrated restaurants, boutiques, and cultural attractions are just minutes away, and premier skiing at Killington's Skyeship Base Lodge is under eight miles from your door. Outdoor living is equally compelling, with a large deck perfectly oriented toward the mountains, an in-ground pool for summer enjoyment, and an oversized garage/barn with storage above presenting exciting potential for a guest suite, studio, or party barn. A rare combination of location, quality, and lifestyle flexibility, this property is ideally suited as a full-time residence, seasonal retreat, or investment in Vermont living at its best. See Listing Details & 57 images.
Under Contract
$1,300,000 $407 per sq.ft. Woodstock VT Home »
4 Beds | 5 Baths | Total Sq. Ft. 3195 | Acres: 1.07Listed on Tuesday Nov 11, 2025
Description: Beautifully sited just a short walk from Woodstock Village, this 2015 custom-built home blends modern comfort with timeless Vermont charm. Thoughtfully designed for everyday living and entertaining, the main level features an open, light-filled layout, a well-appointed kitchen, and seamless access to a sunny three-season room overlooking the landscaped grounds. The sought-after first-floor primary suite offers ease and convenience, with generous closet space and a private bath. With three additional bedrooms plus a dedicated office, the home offers plenty of room to spread out. The large finished basement provides flexible bonus space--perfect for a playroom, media room, fitness area, or hobbies. Central air conditioning ensures year-round comfort, while an oversized, heated garage and an in-ground irrigation system make this home convenient in every season. Step outside to a private patio, surrounded by terraced gardens and stonework that add character and curb appeal. Located in a quiet setting yet within easy reach of restaurants, shops, and the village green, this property offers modern convenience in one of Woodstock's most desirable walk-to-town locations. A rare opportunity to enjoy newer construction in the heart of Vermont's most charming village. See Listing Details & 60 images. Includes a Virtual Tour
