Homes for Sale near Windsor High School

"The Plateau", originally part of the Kennedy Biscuit Co. (Nabisco) family estate, is nestled on a plateau at the end of a private road which greets you with open fields, mature trees, beautiful gardens, and a protected front-and-center view of Mt. Ascutney to the West and the Connecticut River to the East. This private peaceful setting includes an inground pool for those hot summer days, and two

Dan Noble Snyder Donegan Real Estate Group

Set back from the road and with 11+/- acres, this updated historic home has 3 bedrooms and 3 baths. An original part of the Cornish Art Colony, built in 1886, the home has an apartment which can easily become a guest wing or rental if you wish. Light and bright with a lovely open floor plan there are views of Mt. Ascutney and the Connecticut River. Updated kitchen, baths, floors and heating

Jane Darrach Martha E. Diebold/Hanover

Come see and appreciate this recently rejuvenated and extraordinary home that includes 6 bedrooms and 4 bathrooms as well as a 2 car garage! Located just off the downtown village area, this unique property features historical charm and character with vintage woodwork, custom wood floors, high ceilings, spacious rooms and the nooks and crannies a classic home has to offer! Relax on the rear porch

Susan Bellville Bellville Realty

This charming converted farmstead features two primary buildings on one parcel, combining classic Vermont character with solid investment returns. The property offers a diverse mix of one-, two-, and four-bedroom apartments, plus one commercial unit currently leased to a local bath and body company. Additional income comes from a three-bay garage, a shed, and a storage container — all fully

Loren Wehmeyer Tesla Realty Group, LLC

Shown by Appointment Only! Single Family or Duplex! Live in it as a spacious 3 bedroom, 2 bath single family home, or take advantage of the current setup as two separate 1 bedroom units, each with its own utilities. That kind of flexibility is hard to find, whether you're thinking multigenerational living, rental income, or just extra breathing room. And then there's the view. Gorgeous lake views

Rachael Lapp BHHS Verani Upper Valley

Welcome to the Carriage House, a rustic chic hideaway set on 5.13 acres overlooking a private pond in the bucolic West Windsor countryside. The recent, complete renovation of this exceptional property is truly a work of art, blending refined design with effortless comfort. The open main level is thoughtfully designed for both entertaining and everyday living, with a gourmet kitchen featuring

Mary Mayhew Snyder Donegan Real Estate Group

Hartland Hill Farm unfolds across rolling meadows in one of the Upper Valley's most picturesque settings. Sited to embrace the surrounding landscape, the property enjoys sweeping pastoral views east to New Hampshire's White Mountains and south over open fields to the iconic silhouette of Mount Ascutney. Mature maples, stone walls, an apple orchard, two ponds, productive farmland, and a classic

Dia Jenks LandVest, Inc/Woodstock

Farm at Gaelic Crossing is an equestrian property set on 26.72± acres, has dramatic views of Mount Ascutney and, after summer showers, the frequent and magical appearance of rainbows—often even double rainbows—across the wide, open sky. This updated c.1842 New England Cape offers 2,554 square feet of finished living space, including four bedrooms—two conveniently located on the first floor. Wide

Story Jenks LandVest, Inc/Woodstock

Sited on a knoll with lovely views in every direction, this spacious, sun filled Contemporary home was built to last! Using the finest materials, commercial grade mechanics, and custom millwork, this home imbues quality throughout.An impressive fireplace with a wood burning insert anchors the Great Room with sweeping walls of windows integrating indoor and outdoor spaces, and French doors

Danny Kogut Williamson Group Sothebys Intl. Realty

With sweeping views of Mount Ascutney, this exceptional home offers the Vermont lifestyle so many buyers dream of. A place where family and friends gather, traditions begin, and every season brings new adventures. Thoughtfully expanded over time, it blends two living spaces into one inviting home, offering generous room to be together while providing comfort and privacy for everyone.The newer

Gary Coger Four Seasons Sotheby's Int'l Realty

Quietly sited off a private secluded road, sits a finely hand-crafted family home and outbuildings on 10.27 acres. The lot features an open yard, gardens, stone walls, woodland trails & nearby brooks. The main house features post and beam construction with sweeping cathedral ceilings, 2 bedrooms, 1.5 baths, a loft, finished lower level, and many custom-built features. The kitchen is well

Seth Barbiero EXP Realty

This is one of those homes you simply have to experience in person. The views alone are worth the visit. Perched above the valley with commanding, panoramic views of Mount Ascutney, this exceptional custom-built home offers a front-row seat to some of Vermont's most breathtaking scenery. From sunrise over the mountains to spectacular evening sunsets, every window showcases a landscape that

Katie Ladue Gilbert BHHS Verani Upper Valley

Welcome to 23 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 manufactured home offers 1 bedroom, 1 bathroom, and 643 sq. ft. (13'4"x48) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient

Kate Barry EXP Realty

Completely rebuilt in 2014 (except for the storage room) and set on 2.51 acres spanning both Windsor and Hartland, this 2-bedroom, 1-bath ranch offers comfortable one-level living with plenty of potential. The open-concept living, dining, and kitchen area creates a functional layout, while the attached direct-entry garage and unfinished attached space provide excellent storage or future expansion

Karen DeMas Four Seasons Sotheby's Int'l Realty

Take a look at this rare chance to own a BRAND NEW home in the heart of Windsor. Built for efficiency, the house features a raised foundation to keep it out of the flood zone for extra peace of mind. The layout is practical and spacious, offering an open-concept first floor and large bedrooms upstairs.You are within walking distance to the Amtrak station and downtown, and our local Moover

Chelsea Bevis KW Vermont Woodstock

Welcome to The Rock House! A beautiful hillside retreat set on a private, lush landscape with captivating views of Mount Ascutney. The home's spectacular great room is the heart of the property, featuring soaring cathedral ceilings, rich hardwood floors, a dramatic floor to ceiling stone fireplace, and walls of windows that flood the space with natural light while showcasing the breathtaking

Mary Mayhew Snyder Donegan Real Estate Group

Why keep paying rent when you can own? This one bedroom just makes sense. Nothing overwhelming to maintain. A comfortable living space, a kitchen that works, and a bedroom to relax in. Outside you've got a yard that's easy to keep up with, and just enough space to enjoy. And the location can't be beat. Near downtown Windsor, grab dinner or coffee nearby, hop on 91 in minutes, or take a stroll

Allison Griep BHHS Verani Upper Valley

Rustic Charm, Exceptional Outbuildings & Breathtaking Views! Discover the perfect blend of country living and modern comfort in this inviting 2-bedroom, 2-bath log home. Step inside and be welcomed by a stunning floor-to-ceiling stone fireplace, creating a warm and inviting centerpiece for the spacious living area. The home offers a functional kitchen with ample workspace, a formal dining room

Tammy Bergeron Bergeron's Houses to Homes

This beautifully crafted 2024 "Incredible Tiny Home" built by Amish Artisans, is ready for its next owner. Thoughtfully designed for efficiency and comfort, the home features a convenient kitchen, a spacious bathroom, and a loft sleeping area with stairs for easy access. A mini-split system provides both heating and cooling, ensuring year-round comfort. Step outside to enjoy the well-built

Jenna Luce RE/MAX Upper Valley

Stately hilltop home built by Silas Banister c.1800, recently undergone a complete restoration. Quality materials & craftsmanship throughout. It has gorgeous views of nearby Ascutney Mountain & long-range views of NH. The property consists of 98 acres made up of fields, hard & softwoods, trails, a large sugarbush (potential for a future boiling operation). Conserved by Upper Valley Land Trust,

Dana Waters Dark Horse Realty

Welcome to a home where life simply moves at a gentler pace, nestled quietly in the picturesque town of Plainfield, New Hampshire. Perfectly blending storybook charm with everyday convenience, this well maintained residence offers a peaceful rural sanctuary just minutes from the Upper Valley, local shopping, and premier regional hospitals. The grounds unfold like a fairytale landscape with stone

Chelsea Bevis KW Vermont Woodstock

Welcome to 132 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

Kate Barry EXP Realty

Welcome to 11 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient

Kate Barry EXP Realty