Properties Near 37 South Street Woodstock, VT

On a small hill, amongst trees and beautiful gardens, sits this beautifully maintained log cabin with sweeping views of the surrounding mountains and river valley. Just a short drive outside of Woodstock Village, this cabin offers the perfect blend of privacy and convenience. Built in 1996, this thoughtfully crafted home features approximately 2,600 square feet of living space on 2.9 acres. The home offers 3 bedrooms and 2.5 bathrooms, with warm and inviting open living spaces anchored by both a fireplace and a wood stove, perfect for cozy Vermont evenings. A spacious porch takes full advantage of the South Easterly views, providing an ideal spot to relax and take in the natural surroundings. A detached 2-car garage with an accessory dwelling unit studio above, complete with a 3/4 bath; ideal for guests, rental potential, or a private office/studio. A potting shed and a wood shed complete the outdoor spaces, offering ample storage and outdoo hobbies. With its combination of rustic charm, modern utility, and an central location, this property is a rare opportunity to enjoy mountain living without sacrificing accessibility to nearby amenities and recreation.

100 ACRE WOODS!! - Complete turn-key package for vacation rentals and a second home. Tucked away on 96+ protected acres spanning Hartford/Quechee, and a portion of Hartland, this fully furnished 3-bedroom, 2-bath log home offers exceptional privacy, quiet, & year-round recreation....Includes a robust (optional) rental program close to Woodstock. There is an existing subdivision in place if you ever decide to sell off a portion (10 acres with House/86 acres land). A network of private walking & hunting trails winds through the woods, perfect for hiking, snowshoeing, or ATV use. We will even throw in the fancy $20K, 4-wheel 5 seater dump gator & trailer for the right offer! The home’s warm and inviting main level features wide pine floors, cathedral ceilings, and an open layout that blends kitchen, pantry, dining, and living areas around a handsome central chimney with a Vermont Castings woodstove. Upstairs, the spacious primary bedroom enjoys a private sunny bath with a clawfoot soaking tub. Downstairs in the finished lower level, two additional bedrooms share a full bath and are complemented by two laundry/utility rooms offering plenty of storage. Relax on the large wrap-around deck or retreat to the screened porch to enjoy the quiet & wildlife. Ample parking, including space for a motorhome. Includes all furnishings and built-in recreation! Please view the video for the most accurate furnishings list. The property is an active short-term vacation rental with the following June rental dates blocked out: Current rentals 6/25-6/29. Even these dates will change quickly. Property CAN be shown the day someone leaves or arrives.

The perfect combination of feeling like a single family home but with the convenience and ease of townhouse living! Enjoy a park like setting with wonderful landscaping and stone walls throughout. Walk, bike or golf cart to the Quechee Club and Lake Pineo. Located adjacent to the 13th fairway of the Highland golf course. On site there is a beautiful in ground pool and two tennis courts for that spontaneous dip or game to play. This rare End-Unit Coach Road condo has an attached one car garage, extra storage/mudroom off garage, multiple air conditioning units, gas and electric heat, upgraded kitchen with custom cabinetry, granite counters and stainless steel appliances. Two wood burning fireplaces, sauna, and large patio area enhance any style of living. All three bedrooms are oversized each with private baths. Large loft for an office, rec. room or family area. A great opportunity to live in Quechee's finest townhouse village. This is a perfect location and setting to entertain inside or the beautifully landscaped backyard patio, walking and ski trails nearby, minutes to Woodstock and Killington.

This lovely four-bedroom, 2.5-bath cape features a two-car attached garage and a separate 700+/- sq. ft. one-bedroom apartment. The property also includes a separate outbuilding ideal for a workshop or additional storage. The primary living space boasts a modern kitchen with updated cabinetry, granite countertops, and cherry floors. The open-concept family and dining rooms flow into a bright living room equipped with a Woodstock soapstone woodstove, brick hearth, and built-in bookshelves. A three-season porch offers additional space for entertaining. Showings to start May 18, 2026. Open House on May 23, 2026 from 11am to 1pm. The first-floor master suite includes a private full bathroom, two large closets, and a deck. Upstairs, you will find three additional bedrooms, an office/study, and a full bathroom. The separate one-bedroom apartment provides an excellent opportunity for rental income or private guest accommodations. Additional features include a two-car garage and a dog fence/kennel. Located near Mount Tom trails, the home is just five minutes from Woodstock, two minutes from the high school, and twenty minutes from Killington, making it a perfect primary residence or vacation getaway.

Experience the charm and beauty of Vermont living in this meticulously maintained, single owner home nestled within the sought-after Quechee Lakes community off Baker Turn Road. Property Highlights: Wonderful screened on porch for those rainy or buggy nights. 4 bedrooms with potential for a 5th bedroom and/or main-level primary suite. Spacious layout, ideal for entertaining family and guests. Well-loved and thoughtfully cared for throughout. Community & Location Perks: Full access to QLLLA amenities, including: Downhill & cross-country skiing. Lap swimming in the pond or outdoor pool. Tennis and pickleball courts. & so much more!! Conveniently located not far from Killington, VT and Lebanon, NH, leaving you in close proximity to local shops, dining, and career opportunities perfectly positioned for both adventure and everyday living. This is a rare opportunity to own a spacious, move-in-ready home in one of Vermont's most desirable communities. Schedule your showing today!

Great new price! Nestled in the vibrant heart of Woodstock Village, this beautifully renovated residence offers the ultimate "walk-to-all" lifestyle. Stepping inside, newly installed pine flooring guides you through an inviting main level designed for both daily living and effortless entertaining. The cozy living room anchors the home with its warm gas fireplace, while the spacious dining area flows seamlessly into a stunning, expanded kitchen equipped with sleek quartz countertops, and elegant cabinetry. Upstairs, three comfortable bedrooms provide peaceful retreats, highlighted by a versatile sitting room off the primary bedroom that easily transforms into a private study or playroom. Modern peace of mind is built right in, thanks to a new second-floor bath, new energy efficient propane furnace, upgraded 200 AMP electrical wiring, and many more upgrades. Outside, the classic covered porch serves as your front-row seat to the serene village surroundings. Directly across the street, the open green spaces of Vail Field invite you to enjoy playgrounds, ball fields, pickleball/tennis courts or simply walk the dog. Just a short, picturesque stroll away, the very best of Woodstock awaits—from the historic Woodstock Inn and the iconic Village Green to the local elementary school and an array of charming artisan shops, bakeries, and restaurants. For the athlete, this home puts you in the heart of the premier Vermont cycling communities and world class skiing. Complete with a two-car garage with plenty of room to store your outdoor gear, featuring a customizable, partially finished space above, this move-in-ready gem perfectly blends timeless New England charm with modern sophistication.

Excellent opportunity for residential or office/commercial space with easy access and high visibility on Rt 4 coming into town, Currently configured as office space downstairs (which previously has been living spacce), combined with a separate two-bedroom apartment (with its own access) upstairs. The 1,335 sf lower level (Unit C) is currently a chiropractor's office space and was previously used as natural food store and barber shop. The 950 sf upstairs two-bedroom apartment (Unit D) has been leased out by the month for approx $2,000 per month, and has two separate bedrooms, a kitchen, sitting area, balcony and full bath. Or you could re-combine the two units into a larger 2,285 sf in-town residence or office space. There are 4 dedicated parking spaces for the two units, plus other parking in the rear that is shared with the other two units (A & B) of this commercial condo complex. This is a great opporunity to own a highly visible, move-in-ready building right on Route 4.

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.

A rare Woodstock Village opportunity! A Victorian style home located in Woodstock's much desired Maple Street neighborhood! Popular Vail Field recreation area is conveniently nearby! For children in Maple Street's Neighborhood, Woodstock Elementary School is just a short walk away. Currently the residence is configured as home to 2 generations of occupants. A ground floor apartment conveniently accessed from 3 sides of the home comfortably provides accommodation for practical single level living. The main entrance is through a spacious 12'x10' mudroom. A great attribute in Vermont winters! On 1 end of a well thought out floor plan is a generously sized bedroom with a nearby bathroom. Midway in the apartment is a nicely appointed kitchen that then leads to an appealing dining area. Through a door off the dining area several steps lead to a laundry room that conveniently has an exit leading out to the rear of the property. A living room off the dining area completes the attractive apartment. Well placed windows throughout this ground floor provide pleasant views and natural light. A spacious 2nd floor apartment, with 2 levels of living space, is accessed through a private doorway on the front exterior of the residence. A flight of stairs leads up to the primary apartment area consisting of a bedroom, a dining room, a living room, a kitchen and a bath. Off the kitchen is a partially finished laundry area and then stairs leading down to a ground level workshop. Above the primary apartment is a useful 2 room attic area and a potential bath. Although this 2nd floor apartment has been a full time residence, a new owner will certainly choose to renovate some components of the apartment. The landscaped lot has much appeal with space for gardens and for relaxing outside. Residents in this neighborhood can enjoy walking to village amenities of shopping, dining and cultural events. A Victorian style home full of enormous potential! Location, location!