$649,000 $309 per sq.ft. Weathersfield VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 2100  |  Acres: 42
Thursday Sep 25, 2025
Description: Welcome to Chipmunk Hollow, situated on 40+ acres at the base of beautiful Mount Ascutney. This custom mid-century ranch offers unmatched privacy with meadows, two ponds, fruit trees, mature perennials, and 38 acres of woods, all just a mile from I-91 and minutes from Claremont, Dartmouth Medical Center, and Okemo Mountain. The home features 3 bedrooms, 2.5 baths, and a spacious living room with a fieldstone fireplace and panoramic views, while the open kitchen with breakfast bar flows to the dining area and patio. A sunny family room and bonus office with half bath provide flexible living, and the primary suite includes a walk-in closet and full bath, with two additional bedrooms sharing a large hall bath. Mudroom connects to the attached garage with abundant storage and laundry, and the full 2,100 sq ft dry basement with workshop offers expansion potential. Recent updates include a new roof (2024), heat pumps (2023), and septic (2021). Outside, enjoy a storage barn, vegetable garden, walking trails, stone walls, and high-speed internet with excellent cell service for remote work. This one-of-a-kind property blends natural beauty, modern comforts, and convenience. See MLS Property & Listing Details & 48 images.

$256,500 $208 per sq.ft. Windsor VT Home »

3 Beds | 1 Baths |   Total Sq. Ft. 1232  |  Acres: 0.13
Sunday Sep 21, 2025
Description: Located near the end of a dead end street and also near Mill Pond, this home is convenient to where you need to go! There's a nice covered front porch as well as a detached 1 car garage. The interior features 3 bedrooms, formal dining room, a nicely sized living room and character and charm throughout. This property is definitely worth checking out! See MLS Property & Listing Details & 26 images.

$269,000 $204 per sq.ft. Windsor VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1320  |  Acres: 0.13
Tuesday Oct 7, 2025
Description: Step into the timeless appeal of this beautifully maintained 1920s home, ideally situated in the heart of Olde Windsor. The inviting front patio welcomes you into a charming entryway that opens to a cozy living room, perfect for relaxing evenings or entertaining guests. Gleaming hardwood floors flow through the entry and dining areas, adding warmth and character throughout. The spacious dining room connects seamlessly to a well-appointed kitchen, offering both functionality and charm. A conveniently located half bath on the main floor includes an integrated washer and dryer for added ease. From the dining area, step out to the back patio and take in serene views of the expansive backyard, ideal for outdoor gatherings, gardening, or summer barbecues. Upstairs, you'll find three comfortable bedrooms and a full bath, providing plenty of space for family or guests. Perfectly positioned between Mill Pond, Lake Runnenede, and the Connecticut River, this home offers a unique blend of tranquility and convenience. Enjoy a leisurely 15-minute walk to Main Street, where local shops and restaurants create a vibrant small-town atmosphere. Combining vintage charm with thoughtful updates, this Olde Windsor gem is ready to welcome its next chapter. See MLS Property & Listing Details & 33 images.

$399,900 $238 per sq.ft. Windsor VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1680  |  Acres: 0.96
Thursday Sep 18, 2025
Description: Welcome to this well-kept ranch home in the heart of Windsor, VT. Offering 3 bedrooms and 1.5 baths, this home provides a comfortable layout, perfect for everyday living. The spacious living room is bright and inviting, opening easily into the eat-in kitchen where there's plenty of room for family and friends to gather. This is what a true turnkey home looks like; new roof, windows, siding, decking, electrical, flooring, whole house generator, and beautiful new baths and kitchen complete with granite countertops. Boiler was replaced just before these owners purchased in 2016. Even the basement has potential to be fully finished if you need more living space or to have a workshop or home studio. Enjoy the convenience of a 2-car garage and a level lot that's ideal for gardening, pets, or outdoor entertaining. Single-level living makes this property easy to maintain, while the location offers quick access to Windsor's shops, restaurants, and local amenities. Whether you're looking for your first home, a place to downsize, or a Vermont getaway, this ranch is full of potential and ready for its next chapter. See MLS Property & Listing Details & 28 images.

$499,000 $344 per sq.ft. Windsor VT Home »

Price Change! Reduced by $136,000 down 27% on October 7th 2025
3 Beds | 3 Baths |   Total Sq. Ft. 1452  |  Acres: 10.18
Monday Jun 16, 2025
Description: Enjoy privacy and lovely views from this well executed contemporary home overlooking copious gardens and mature plantings to a spectacular pond with an arched footbridge (spotlights highlight the bridge after dark) to access your own little island. Beautiful updates throughout the home include new maintenance-free manufactured cedar-tone shingles on the entire house and workshop shed. The kitchen features custom oak cabinetry, granite counters and updated appliances. The living room has sweeping cathedral ceilings, hardwood walls, oversized windows, and a wood burning fireplace. There is a primary Bedroom ensuite, and a guest powder room off of the foyer mudroom complete with slate floors. Step out to a private iron balcony with Trex decking and spiral stairway accessing a stone terrace below complete with fire pit, water feature and screened gazebo. Upper level has a spacious loft area, and a second bedroom. The walk out lower level includes a third bedroom, studio/rec room (could accommodate overflow guests) and laundry, plus a wine or root cellar. Oversized two car garage with plenty of storage above. Located just minutes from I 91. Easy access to Upper Valley, DHMC, Woodstock, skiing and all recreation. See MLS Property & Listing Details & 39 images.

$595,000 $310 per sq.ft. Woodstock VT Home »

Price Change! Reduced by $100,000 down 17% on October 24th 2025
3 Beds | 2 Baths |   Total Sq. Ft. 1920  |  Acres: 6.88
Friday Sep 12, 2025
Description: This tidy, well maintained Mid-Century Ranch home is conveniently located just 1.5 miles from the Village Green. Perched on a sunny knoll with a southern valley view, this well maintained home features open concept kitchen/dining, a large, bright living room, three bedrooms all with oak floors, a walk out basement providing opportunity for guest accommodation, or a hobby/play room. The 2 car garage with ample storage above is connected by a breezeway. 3 mini splits for efficiency and comfort. Backup generator, pellet stove, wood stove. Newer heat pump water heater, new windows. Huge shed barn for storage or workshop. See MLS Property & Listing Details & 43 images.

$675,000 $434 per sq.ft. Woodstock VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 1555  |  Acres: 0.34
Saturday Sep 6, 2025
Description: Prime In-Village location on Mountain Avenue just steps to Faulkner Park, The Mt Tom trail system and Woodstock Rec Center. This classic New England duplex (eastern side) home serves perfectly as a full time residence, or an easy keep as a second home. Through a classic covered porch enter the foyer with gleaming hardwood floors and high ceilings. The spacious living room has a propane stove, and large six over six windows flooding the room with natural light. The DR has original built-ins, and connects to a roomy farmhouse eat-in kitchen. Rear mudroom steps out to covered porch and detached garage. Office or overflow bedroom with 3/4 bath completes the main level. Moving upstairs there are three bedrooms, a full and a half bath. Opportunity to expand into the attic space above. See MLS Property & Listing Details & 33 images.

$785,000 $473 per sq.ft. Woodstock VT Home »

Price Change! Reduced by $25,000 down 3% on October 24th 2025
3 Beds | 2 Baths |   Total Sq. Ft. 1660  |  Acres: 0.19
Monday Sep 15, 2025
Description: New price! Welcome to this beautifully renovated residence in the vibrant heart of Woodstock Village. Enjoy unparalleled convenience with a short stroll to the Elementary School, Woodstock Inn, the picturesque Green, and an array of charming shops, restaurants, and bakeries that define village living. Nestled directly across from Vail Field, this home offers easy access to playgrounds, ball fields, and pickleball courts. The homeowners have meticulously updated the property, featuring a stunning new kitchen and a refreshed second-floor bath, blending modern comfort with timeless charm. Unwind on the covered porch with a favorite drink while soaking in the serene surroundings. The inviting living room has a cozy gas fireplace, perfect for cool evenings. The spacious dining area opens to the expanded kitchen, boasting elegant cabinetry, sleek quartz countertops, and top-quality appliances. Newly installed pine flooring adds sophistication throughout. With three spacious bedrooms and two updated bathrooms, each room is designed for comfort. A versatile sitting room off the primary bedroom is perfect as a playroom or quiet study. Additional features include a new boiler, new dining room windows, and upgraded wiring with 200 AMP service. The property also offers a two-stall garage with partially finished space above, presenting endless customization possibilities. Whether you're seeking a forever home or a peaceful retreat, this move-in-ready gem is a must-see! See MLS Property & Listing Details & 49 images.

$877,000 $318 per sq.ft. Woodstock VT Home »

Price Change! Reduced by $108,000 down 12% on September 17th 2025
3 Beds | 2 Baths |   Total Sq. Ft. 2760  |  Acres: 10.1
Thursday Jul 3, 2025
Description: This is a rare opportunity to own 10.1 acres of land in a coveted area of Woodstock that includes a 1988 Frizzell Builders house and a detached oversized garage with a second floor for storage . The property was part of the King Farm which is now in Vt. Land Trust as conserved land , until it was split off in the late 1980's when the Colby family came into ownership and built the existing house .The dwelling has a wrap around deck overlooking the meadows and pond with views to the south. Antique stone walls are reminiscent of days gone by .If privacy but convenience to Woodstock village is your goal you need not look further. Some of the features include hardwood floors , open floorplan that includes dining and living room , large downstairs game room. Easy access to Killington, Okemo Mountain and of course Woodstock's own Saskadena Six for Skiing . Golf, tennis . biking and fishing are just a few of the many outdoor activities in the area . Pentangle Arts provides music and theater throughout the year. Woodstock was named the prettiest small town in America . Come make it your home in this amazing property. Call today for an appointment. See MLS Property & Listing Details & 57 images.

$944,999 $440 per sq.ft. Woodstock VT Home »

Price Change! Reduced by $155,001 down 16% on September 8th 2025
3 Beds | 3 Baths |   Total Sq. Ft. 2150  |  Acres: 1.49
Thursday Jun 5, 2025
Description: Enjoy in-town ease of living combined with Vermont country charm. This well maintained , efficient home provides first floor living with an additional lower floor ensuite bedroom /sitting area with direct access to lovely grounds and gardens. The light filled home is in excellent condition and is surrounded by fabulous perennial gardens, mature maple trees, raspberry and blueberry bushes , stone patio and 2 decks offering plenty of spaces for outdoor living and entertaining. The open floor plan provides easy flow and the large windows and glass doors bring the out of doors in. A big bonus is central air conditioning ! The detached 2 car garage provides lots of storage and work space area . Enjoy the charm and various amenities of Woodstock Village that consistently is named one of the prettiest small towns in America . Easy access to sports for every season.. Twenty minutes to the Upper Valley , two and a half hours to Boston and 5 hours to NYC. Call today for an appointment . See MLS Property & Listing Details & 55 images.

$985,000 $513 per sq.ft. Woodstock VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 1920  |  Acres: 6.02
Tuesday Jul 1, 2025
Description: PRIME LOCATION! Tucked away at the end of a peaceful dead-end road in the Westerdale neighborhood is this Vermont Cape Cod home offers the perfect blend of privacy and convenience on just over 6 acres. Surrounded by mature trees and set on a wooded lot overlooking a tranquil pond, you'll enjoy the calm of nature right outside your doorstep. The freshly installed deck provides a serene spot. Well-planned interior space, inside you will find a warm and inviting atmosphere, offering an eat-in kitchen enhanced by the heat from the wood stove or relax by the fireplace in the living room open to the dining room. The primary bedroom with a full bath featuring a jacuzzi tub, while the remaining rooms provide flexible options for guests. Recent updates like a new oil tank and a new water pressure tank ensure reliable modern living. Located just minutes from the heart of Woodstock, this home gives you easy access to local favorites like the Billings Farm and year-round fun at Okemo Mountain Resort. Whether you're into skiing, hiking, or something entirely more relaxed, there's something nearby for everyone. The neighborhood boasts a strong sense of an upscale community while maintaining a rural, secluded vibe. It's that rare find that feels remote but keeps you close to all the essentials. Ideal for year-round living or a seasonal getaway, this property invites you to experience the best of Vermont in a setting that's equal parts comfort and character. See MLS Property & Listing Details & 54 images.

$1,750,000 $323 per sq.ft. Woodstock VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 5422  |  Acres: 31.43
Wednesday May 28, 2025
Description: Offered for the first time, the exclusive private residence of one of Woodstock's most notable and prolific builders, Hank Savelberg. Located just five minutes from the Woodstock Village Green, this whimsical, private, contemporary hillside estate was lovingly constructed featuring well thought, connected open spaces with expansive glass walls and dramatic sweeping wooden ceilings. The entire home is a unique showplace of clever spaces, built-ins, with custom detail throughout; featuring mahogany, cherry, and locally sourced stone. The ten room- three bedroom, three bath main residence was carefully sited to optimize a stunning northeasterly view, and to communicate directly with exterior terraces, and established gardens overlooking a pond, rolling hills and fields. There is a detached one bedroom guest house (or caretaker's cottage), garage, horse barn, equipment shed and two garden sheds. Easy access to hiking trails. Three minutes to Fitness Ctr., 15 minutes to Saskadena Six skiing. 2.25 hours to Boston, 4.5 to NYC. Property enrolled in Current Use. See MLS Property & Listing Details & 60 images.

$8,000,000 $1,486 per sq.ft. Woodstock VT Home »

3 Beds | 4 Baths |   Total Sq. Ft. 5384  |  Acres: 68.92
Monday May 5, 2025
Description: Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a testament to elegant durability. From the mahogany exterior to the hand crafted front doors and custom-wrought hardware, this spacious and meticulously considered home celebrates the skill of Vermont's most talented craftspeople. The unparalleled 180 degree views over the Woodstock valley are spectacular in every season, offering year-round sunlight and ever-changing vistas. With a gourmet kitchen custom-built for entertaining, a 1,000 bottle wine cellar, and a double-sided great room fireplace, Sorgenfrei perfects conviviality. The measures taken to ensure the property's efficiency and durability are too numerous to name - among them, an 18kw solar array, Pella Architect-Series windows, and custom mortise and tenon fir construction. At home among Woodstock's most lauded residences, and gorgeously situated in one of the area's most prestigious neighborhoods, this home is a testament to uncompromising vision and a paean to unparalleled enjoyment of Vermont's Green Mountains. See MLS Property & Listing Details & 47 images. Includes a Virtual Tour