Homes for Sale near Windsor High School

Strong Cash Flow! Profitable Investment Opportunity! This fully leased three unit multifamily property is an excellent chance for investors to add a consistent cash flowing property to their portfolio or for an onsite owner to occupy one unit and let the extra additional rents help pay for your housing. A low maintenance property with nice updates over the years which include separate electrical

Alex DeFelice The Clerkin Agency, P.C.

Nestled on 1.34 picturesque acres in historic Windsor, this classic 4-bedroom Colonial blends timeless charm with comfortable living. Set back from the road, the home offers privacy and space to enjoy Vermont’s natural beauty while being just minutes from town amenities, schools, and I-91.Inside, you'll find a traditional floor plan with spacious living and dining areas, a well-appointed

Katie Ladue Gilbert KW Vermont Woodstock

Spread out into 5.17 peaceful acres along picturesque Dodge Road, this meticulously cared-for ranch-style home offers a rare blend of privacy, beauty, and opportunity. Surrounded by mature plantings, lush gardens, and a bounty of fruit trees, the flat, level lot is a gardener’s dream, perfect for those seeking tranquility and space to cultivate. The home itself has been lovingly rebuilt and

Tyler Hall BHHS Verani Upper Valley

1850 home re-furbished top to bottom for modern amenities with antique charm. New roof, floors, kitchen, bathrooms, windows, electrical, plumbing, and heating throughout. Very large flat yard located right downtown.

Derek Eisenberg Continental Real Estate Group, Inc.

Welcome to your private 8-acre homestead retreat in West Windsor, where nature, comfort, and self-sufficiency come together for everyday adventure. Explore wooded trails, swim in your own peaceful pond, or sip your morning brew on the sunny coffee deck. Evenings shine around the single fire pit, while a handcrafted treehouse brings out the kid in everyone.Grow your own food with raised garden

Eric Johnston Four Seasons Sotheby's Int'l Realty

This well cared for contemporary home has only been used as a second home for the original owners. The house takes advantage of the southwest exposure to be able to bring the outside in with the use of large palladium windows and multiple French doors. Some of the interior features include 3 woodburning fireplaces ,wide pine floors ,vaulted ceilings ,and skylights. The floor plan has an easy

Carol Wood Williamson Group Sothebys Intl. Realty

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

Danny Kogut Williamson Group Sothebys Intl. Realty

Adorable & Turn-key 3 bedroom, 2 bath home on landscaped 1.53 acres corner lot in the heart of Ascutney Mt Resort! Many upgrades including Bosch High Efficiency Propane Boiler, Mitsubishi heat pump/AC, Rinnai on demand hot water heater, new well tank & centrifuge filtration system, new fireplace & chimney with Woodstock soapstone woodstove flanked by custom cabinets on each side. Decks, extensive

Dana Waters Dark Horse Realty

Price Improvement!!! Welcome to this quintessential New England home nestled in the hills of New Hampshire’s Cornish Arts Colony. Bursting with antique character, this residence offers timeless details including wide-plank floors, exposed beams, and rich woodwork that speak to its heritage. The wandering interior boasts inviting spaces with a warm, intimate feel. On the second floor, you will

Raelene Robinson-Garrow KW Vermont Woodstock

In a charming setting overlooking the Lull Brook, this house is the perfect home or retreat for one or two people. A large room for living/dining/kitchen and a loft bedroom up a flight of stairs. Full bath on the first level. Incredibly pretty woodwork and outstanding views. This house has MAGIC! Has been used both as a primary residence and a very successful Air B and B.Property will

Jane Darrach Martha E. Diebold/Hanover

Located near the end of a country cul-de-sac at Ascutney Mountain this Split entry has 3BR/2BA it is configured as two units with separate entries & 2 kitchens but has been used as a single-family home, as well. It has 2 nice brick fireplaces; one with a VT Castings woodstove insert, the other has a wood stove hook up. Recent updates include a new Rinnai direct vent propane heater, 2 Tesla Power

Dana Waters Dark Horse Realty

Welcome to this nicely maintained 2-bedroom + loft condo offering direct access to the renowned Ascutney Trails—perfect for mountain biking, skiing, hiking, and trail running. Enjoy stunning mountain views from the spacious living room, which features two large sliding glass doors that flood the space with natural light. The open loft above the living area offers even more scenic vistas and

Daniel Preston KW Vermont Woodstock

Discover classic Vermont charm in this 3-bedroom, 1.5-bathroom home located on a quiet, tree-lined street just steps from downtown Windsor. This home is perfect for those who appreciate historic charm and are ready to make it their own. Inside, you’ll find a welcoming layout and abundant natural light. The first floor features a full bathroom, laundry, spacious living and dining areas, and an

Tara Reeves Vermont Real Estate Company

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

This spacious walk-up condominium features 3 bedrooms and 3 full baths, with an inviting open-concept living and dining area anchored by a cozy fireplace. Step out onto your private deck overlooking the tubing hill and take in all the action just outside your door!This vibrant community offers an unbeatable lifestyle with access to approximately 1,300 acres of outdoor fun, including

Allison Griep KW Vermont Woodstock

OWN FOR LESS THAN YOU CAN RENT!! Spacious and bright end unit condo on Ascutney Mountain. Fireplaced living room, dining area with balcony, kitchen and even an entry enclave. 3 bedrooms with 3 full baths. 1 bed/bath on 1st floor. 2 bedrooms, 2 baths, multiple closets and a sitting area on the upper level. The advantage of the 3rd floor is that you get the loft area, cathedral ceilings and some

Crystal Moses Crystal Moses

Charming Duplex in the Heart of Windsor – Ideal for Owner-Occupants or Investors! Discover a fantastic opportunity to own a versatile, income-producing duplex in the vibrant and historic town of Windsor. Perfectly suited for an owner-occupant looking to offset their mortgage with rental income—or a savvy investor seeking solid returns—this well-maintained property offers both comfort and cash

Daniel Preston KW Vermont Woodstock

Charming Duplex in the Heart of Windsor – Ideal for Owner-Occupants or Investors! Discover a fantastic opportunity to own a versatile, income-producing duplex in the vibrant and historic town of Windsor. Perfectly suited for an owner-occupant looking to offset their mortgage with rental income—or a savvy investor seeking solid returns—this well-maintained property offers both comfort and cash

Daniel Preston KW Vermont 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

Story Jenks LandVest, Inc/Woodstock

Open floor plan with soaring ceilings and wood flooring throughout. The structure includes a full bathroom, a partial kitchen, and the framework for two bedrooms—ideal for conversion into a spacious single-family home or potentially a duplex. New hot air heating oil system install fall 2024 The building was officially approved for residential use in 2023. Recent upgrades enhance the property's

Deb Roberts RE/MAX Upper Valley

This tidy, well orchestrated Custom Timber Frame Cape is the perfect package! You will love the beautiful, bright spaces that connect seamlessly for every day living and entertaining. Tasteful updates and improvements throughout, this house was designed with convenience in mind. Gleaming hardwood floors run through the main and second level. The roomy country kitchen has soapstone counters, and

Danny Kogut Williamson Group Sothebys Intl. Realty

Formerly Hartland Schoolhouse #11, this charming antique brick colonial in a village location, is just a 6 minute drive from an I-91 entrance/exit. Beautiful natural light in the 3 bedrooms, 2 baths. Indian shutters, lovely old wood floors and moldings and a surprisingly open floor plan. A very easy commute to Dartmouth College or Dartmouth Health.

Jane Darrach Martha E. Diebold/Hanover

Introducing a prime investment opportunity nestled on 1.44 acres of picturesque countryside just moments away from the convenience of town living. Whether you're a seasoned investor seeking a lucrative addition to your portfolio or a newcomer to the world of real estate investment, this 8-unit property presents an attractive proposition. With its idyllic location, modern updates, and reliable

Katie Ladue Gilbert KW Vermont Woodstock

The Stephen Jacob House is an extremely important historic residence in a town known for its historic architecture. Built in 1784 in the Georgian/Federal style, the residence was sited on the rise of State Street from the Village of Windsor. It's commanding presence was embellished with cornice dentil detailing and possibly a Palladian window. Having been used for many purposes over the

Wade Treadway Wade I Treadway Real Estate

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

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

Welcome to 517 Back Mountain Rd., 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 84 Cubb Court, , Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-66 model manufactured home offers 3 bedrooms, 2 bathrooms, and 880 sq. ft. (13'4"x66) 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

INVESTMENT PROPERTY. 4 UNITS, 1 1-bedroom unit & 3 2-bedroom units. Separate basement for each unit. Recent improvement includes, new roof, replaced plywood, foam board and membrane, at a cost of $70,600.00. Heat is separate pellet stoves for each unit, also an oil-fired steam system if needed for backup. Electric is separate, tenants pay electric. Landlord pays heat. Minimum of 48-hour required

Don Chabot Town and Country Realty