Properties Near 88 Happy Valley Road Woodstock, VT

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!

Step back in time without sacrificing modern comfort in the iconic "Carter House," a beautifully preserved antique home in the heart of Quechee Village. Meticulously maintained and thoughtfully updated, this one-of-a-kind property seamlessly blends timeless character with today's conveniences. The entirely renovated kitchen and dining area create the perfect gathering space, while a stunning remodeled bathroom featuring a spacious walk-in shower and premium finishes offers a luxurious start to every day. A newer boiler, Marvin replacement windows throughout, and numerous additional upgrades ensure efficiency and peace of mind while preserving the home's historic charm. Rich in character, you'll find beautiful built-ins, inviting living spaces, and thoughtful details throughout. The attached heated workshop provides exceptional flexibility and can easily serve as a one-car garage. Outside, established perennial gardens, a welcoming flagstone entry, and an attractive exterior create exceptional curb appeal. Enjoy the unique experience of watching colorful hot air balloons drift overhead from your own front yard and take an easy stroll to the renowned Simon Pearce restaurant, glassblowing studio, and village shops. The private primary suite offers a peaceful retreat, complemented by two additional bedrooms. Best of all, this property is not part of Quechee Lakes Association, allowing you to enjoy the charm of Quechee Village without association membership. A rare opportunity to own one of Quechee's treasured historic homes, where classic New England character meets modern living.

Superbly located on Baker Turn, this inviting three-bedroom, two-bath home offers exceptional indoor and outdoor living with easy golf-cart access to the Quechee Club. An abundance of glass throughout the home fills every room with natural light and creates a wonderful connection to the surrounding landscape. The expansive wraparound deck extends from the dining room, connecting the home to the oversized garage and an elevated screened porch. With skylights and ample room for both a large dining area and comfortable lounge seating, the porch is ideal for entertaining or relaxing throughout the warmer months. The bonus room above the garage offers excellent flexibility and could easily serve as an additional bedroom, bunk room, or recreation space. The oversized garage comfortably accommodates an SUV, sedan, and golf cart, while a cedar closet provides convenient additional storage. Numerous updates and improvements enhance the property, including completely renovated bathrooms, heat pumps installed throughout, a refinished deck, resurfaced driveway, new well pump, and new LeafGuard gutters. With its versatile spaces, extensive outdoor living areas, abundant natural light, and desirable Baker Turn location, this is a wonderful opportunity to enjoy all that Quechee has to offer.

Classic Deck House design meets the Vermont lifestyle in this inviting Quechee Lakes home. Featuring the signature architectural elements that make Deck Houses so desirable, you'll love the soaring wood ceilings, walls of windows, and seamless connection to the natural surroundings. The open-concept floor plan creates a bright and welcoming living space, perfect for entertaining or everyday living. The primary suite offers a private bath, while two additional bedrooms provide plenty of room for family and guests. A dedicated office makes working from home easy, and the spacious family room offers flexible space for recreation, media, or hobbies. Enjoy seasonal views from multiple decks and the large screened porch, providing the perfect setting for morning coffee, outdoor dining, or relaxing after a day of adventure. A detached two-car garage offers ample storage for vehicles and outdoor gear. As part of the Quechee Lakes community, you'll have access to an exceptional array of amenities, including two championship golf courses, tennis and pickleball courts, a private lake with sandy beach, ski hill, extensive hiking trails, indoor and outdoor pools, fitness facilities, and more. A wonderful opportunity to enjoy the unique character of a classic Deck House and the unmatched lifestyle of Quechee Lakes.

**Sale Price includes MLS#5072395 Well-maintained 2-bedroom, 1.5-bath single-family home offering 1,278 sq. ft. of living space. Featuring a wrap-around enclosed porch and a full basement, ideal for storage. Set on a .65± acre property with excellent Route 4 frontage and visibility, just seconds to Interstate 89. The sale also includes a 3,020 sq. ft. commercial building and a second residential home (MLS#5072395), creating outstanding income or mixed-use potential. Infrastructure includes a shared well and ROW, an ideal opportunity for owner-occupants, investors, or owner-operators seeking flexibility and long-term value. Additional single family home available on abutting property for purchase on additional .65 acres.

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.

This spacious four-bedroom, four-bathroom Quechee Lakes home features lovely landscaping, established perennial beds, a classic stone wall, and an attached two-car garage. The first floor offers a functional open-plan layout, highlighting a large kitchen equipped with updated appliances, extensive cabinet storage, and granite countertops. The space flows seamlessly into a living room with a propane fireplace and a dining room with direct access to the back deck. A generous mudroom with laundry completes the main level. The second floor accommodates three bedrooms and three bathrooms. This includes the large primary bedroom, which features a spacious walk-in closet, cedar closet, two additional closets, and an en-suite bathroom. Additional features include versatile bonus space in the walk-out lower level. The home also benefits from recent mechanical and structural improvements, including an updated heating system, central air-conditioning, and added insulation. A great house in a great location! Home priced below market value to promote a clean and quick sale. Seller is a licensed Real Estate Agent.

Live Work Play, Retire and Play, or Just Play on the Weekends and Holidays! This wonderful 3 BR, 3 Bath Townhome/Condo has it all. Nestled in a small quiet wooded community less than 5 minutes from the Historic Woodstock Center and conveniently located within walking distance of Woodstock Union Middle & High School. It is also located only 30 minutes from Killington Ski Resort and Okemo Ski Resort and 10 minutes from Saskadena Six. The location and price make this home a truly unique buying opportunity for several types of owners. The very private 24 home community is comprised of retirees, working families, and second home owners who want to enjoy all Vermont has to offer. The neighbors are awesome! This home is the most private in the complex as it is the very end unit surrounded on 3 sides by woods and streams. The unit is in very good condition and move in ready. The first floor is comprised of a den/bedroom with pocket doors for added privacy and an adjacent 3/4 bath. Also on the first floor is a spacious living room anchored by a propane fireplace, nicely crafted mantle and hardwood floors. A couple of steps down takes you into a renovated kitchen with stainless appliances and gleaming soapstone counters. A small eating area is surrounded by windows overlooking the back deck facing east with beautiful woods on 2 sides. Wildlife abounds. Tall ceilings and an abundance of natural light make the kitchen area a favorite space. The second floor consists of a very large primary bedroom with a seating area and three closets for an abundance of storage. The second bedroom is spacious with lots of sunlight. A good size full bathroom with tiled floors completes the second level. The lower level is a large family room with a walk out to a lovely patio. This level also has its own 3/4 bathroom, laundry area and several storage closets. The lower level has lots of options for use given the design. Open House- Saturday July 18th from 11am-1pm

Nestled on a serene 3.3-acre parcel, this charming 1990s Cape offers privacy and elevated views, just minutes from town. With three spacious bedrooms, two dedicated offices, and a welcoming country kitchen, it’s ideal for work and relaxation. Enjoy the full walk-out basement, oversized two-car garage with a workshop, and a handy shed for your hobbies. A lovely garden area completes this peaceful retreat, your perfect country escape awaits!

Enjoy one level living in this very well maintained home. Part of the Quechee Lakes community with all of its' amenities the property is perfect as a second home or a primary residence . The lovely deck with surrounding perennial gardens is the perfect place for enjoying an afternoon drink or a morning coffee. Large windows and multiple accesses to the out of doors provide lots of light inside. The woodburning fireplace offers a cozy spot to relax on winter evenings. Situated within a short drive to the Upper Valley with everything it has to offer as well as being just minutes from the historic town of Woodstock Vt. 2 1/4 hours to Boston and 5 hours to NYC. Sold mostly furnished. The closing cannot occur prior to 10/01/2026. Make an appointment for a private viewing .

Fully furnished condo nestled in a small quiet community just 5 minutes from "Historic Woodstock". Super location! This unit is in very good condition- first floor comprised of a den//bedroom with pocket doors for added privacy and an adjacent 3/4 bath. Spacious living room anchored by a newer propane fireplace to curl up with a book on a cold winter day. A couple of steps down takes you into a renovated kitchen with small eating area overlooking the back deck. Tall ceilings allow this space to feel spacious with an abundance of natural light. Second floor consisted of a very large primary bedroom with ample closets and sitting area. A full bathroom and the second bedroom is a perfect size for guests. Lower level has a walk out patio with new slider doors, large family room with a small kitchen and eat-in area, spacious laundry and 3/4 bathroom. Newer Buderus boiler. Pets are allowed- Offered furnished with all new custom curtains. Come take a look at this turn key property!

Price improved! Come and see this gorgeous Quechee Lakes condo with a recently completed full makeover. High end furnishings and most of contents are negotiable and could convey! Experience modern mountain living in this beautifully renovated 2 bedroom, 4 bath townhome. Every detail has been thoughtfully updated, including a stunning new kitchen, luxurious baths, stylish flooring, energy efficient mini splits on every level, and a cozy gas fireplace. The home's gorgeous contemporary aesthetic is complemented by sweeping views across community meadows to majestic Mt. Ascutney. The open concept main level features a spacious entry with laundry, kitchen, dining and living. The gorgeous new kitchen features a coffee bar with a sink and a clever instant hot water tap. Sit in your dining and living areas and enjoy the gas fireplace while taking in the amazing views! The second level features two spacious bedrooms, each with its own beautifully appointed ensuite bath, offering comfort and privacy for family and guests. The fully renovated walkout lower level adds exceptional living space with a welcoming den, wood stove, 3/4 bath, kitchenette, and full sliding doors that showcase the same picturesque views; perfect for entertaining, hosting guests, or creating a private retreat. Located in the sought-after four-season Quechee Lakes community, owners enjoy access to an exceptional array of amenities, including two championship 18-hole golf courses, a premier tennis center, indoor and outdoor swimming pools, a private community lake, ski hill, fitness facilities, restaurants, and miles of year-round recreational opportunities. This turnkey home combines modern style, versatile living spaces, and one of Vermont's premier resort lifestyles. Do not miss this wonderfully updated townhome! Open house during a Quechee Lakes multi home "block party" Thursday August 13 from 5-7 pm.

EXCLUSIVE UPPER VALLEY OPPORTUNITY: Enjoy premium village living at a controlled, accessible price point through the Woodstock Community Trust Local Deeds Program! Perfect for employees of major local institutions like The Woodstock Inn, Dartmouth Health, Dartmouth College, and Hypertherm. This program bypasses out-of-state bidding wars to keep high-quality housing available for our regional workforce. THE HOME: The largest layout in a peaceful 24 home community, this immaculate Federal-style brick townhouse offers 2,268 sq ft of living space across three fully finished levels. It functions seamlessly like a single-family home, boasting an open floor plan, bright natural light, a wood burning fireplace, and stunning hardwood floors. The layout features 2 spacious upstairs bedrooms and a highly versatile 1st-floor flex room with pocket doors, perfect as a 3rd bedroom, home office, or guest suite. KEY HIGHLIGHTS: Baths on every level. Private, oversized outdoor deck surrounded by mature woods and perennial gardens. Walking distance to the Woodstock Farmers’ Market and National Park trailheads. Updated electrical, plumbing, 2019 furnace, and a brand-new dryer. ELIGIBILITY: One occupant of your household works or will work locally at least 25 hours per week for a business or organization located within a 16 mile radius of the Woodstock Town Hall. The occupant can be either the homeowner or a long term tenant. Short term rentals (i.e., less than 30 days) are strictly prohibited. Covenants and Woodstock Trust eligibility documents are attached.