Windsor County VT Homes under $500,000

Turn-key living meets summer-ready fun, this beautifully renovated Wilder home with a private in-ground pool and three season porch is just a short walk to Kilowatt and Frost Parks offering both convenience and a wonderful neighborhood setting. This charming property features 4 bedrooms and 2 bathrooms, providing plenty of space for comfortable, everyday living. The bright, updated kitchen flows

Gerry Stark RE/MAX Upper Valley

Welcome to a property where Vermont’s natural beauty meets a lifestyle of quiet productivity and potential. Situated on 18.45+/- private acres in Springfield, this 1988-built home spans 2,548 square feet of living space designed to celebrate its surroundings. The heart of the residence is defined by its exceptional southern exposure; several sliding glass doors line the south-facing side of the

Jill Lawrence The Real Estate Collaborative

A rare piece of Vermont history, thoughtfully preserved for modern living. Dating to 1790, this distinguished brick and frame Colonial stands as a testament to early New England craftsmanship — and it's ready for its next chapter. Meticulously maintained over the centuries and updated where it counts, this two-story home offers the warmth of wide-plank hardwood and softwood floors, the peace of

Allison Griep BHHS Verani Upper Valley

This property is conveniently located in Bridgewater Village, situated midway between Woodstock and the Killington Ski Area. While currently configured as three income-producing units, it offers an outstanding opportunity for a creative conversion back into a single-family residence, with the detached rear unit available to supplement the cost of ownership. Recent updates include a new roof,

Bonnie Bergeron Snyder Donegan Real Estate Group

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

Gretchjen Smith Williamson Group Sothebys Intl. Realty

Bright, easy to maintain and furnished 3 bedroom, 3 bath house with all that Quechee Lakes has to offer. This home includes newer floors. kitchen appliances, 2 remodeled bathrooms, a whole house generator, and a garage with an electric car charger. Enjoy the outdoors with a large deck and an electric dog fence around the whole house.

Sandra Dell KW Coastal and Lakes & Mountains Realty/Hanover

Situated on a private 4.6 acre lot this unfinished home is awaiting your vision to compete it. Currently a 2-bedroom 1 bath in a lower-level walkout, awaiting the second story. You can live in the home and complete it in your own time frame or bring a builder and finish it now to your specifications. The home is a 44 ft x 26 ft base and can be a single or two story above. It has a 4-bedroom

Linda White EXP Realty

Nestled in the picturesque hollows of Rochester, Vermont, this charming and fully updated home offers the ease of one-level living in a modest yet wonderfully comfortable package. Antique softwood floors, knotty pine ceilings, and a large bay window framing beautiful North Hollow views create a warm and inviting atmosphere, while the open floor plan is equally suited for entertaining and intimate

Kyle Kershner Killington Pico Realty

Versatile Ludlow retreat on 9 acres with proven short-term rental history, offering flexible living options ideal for owner-occupants or investors seeking income near Okemo Mountain. This property is configured as a single-family residence with two distinct living levels, each featuring private entrances and amenities that allow for multiple use scenarios. The ground floor living area includes a

Matthew Bellantoni Mary W. Davis Realtor & Assoc., Inc.

A one-of-a-kind Vermont retreat where thoughtful design, craftsmanship, and landscape converge. This 3-bedroom, 2-bath home has been expanded and fully renovated including a new roof, state-of-the-art heating system, and solid hardwood flooring. Every surface has been custom-finished, blending modern comfort with artistic mid-century modern influences for a home that feels more curated than

Zoe Hathorn Washburn Snyder Donegan Real Estate Group

Take a look at this home in central Vermont- close to the premier Killington Mountain Ski Resort. This property is on an open 2 acre lot with plenty of sun and space for pets, gardens or greenhouses. An adjoining 1 acre house lot can be purchased for an additional 30k if interested now. This Stockbridge home has an extra living apartment below- accessible by a separate driveway. It provides

Risa Mornis Covered Bridge RE

Welcome to the former Danforth Inn! Take a trip back in time to 1780 as you look at this extremely original old building that was built in Weathersfield Bow in 1780 by Gideon Lyman. In 1789 Joseph Danforth moved to the Bow and he leased and then bought the Inn, changing the name to the Danforth Inn. This property will need some love, but it has never been spoiled in its originality, and it's just

Glenn Olney Barrett and Valley Associates Inc.

Two buildings on one parcel in desirable Hartland, Vermont! This flexible and well-maintained property includes a single-family home and a duplex, offering outstanding potential for owner occupancy, multi-generational living, or investment income. Ideally situated just 25 minutes from Hanover, NH, and 10 minutes from Woodstock, VT, this location provides the perfect balance of convenience and

Loren Wehmeyer Tesla Realty Group, LLC

Super cute, renovated two bedroom home. Detached garage for some extra storage. Only 15 minutes to Dartmouth Hitchcock & Dartmouth College. Being 2.5 acres, there is plenty of room to expand if you wanted to!

Lyndsey Freeman Quechee Lakes Real Estate Center

Tucked away on a picturesque 3-acre lot, this classic three-bedroom expanded Cape offers privacy, seclusion, and peaceful views in a beautiful Rochester valley setting. Set nearly 700 feet back from the road and bordering the Green Mountain National Forest, the property enjoys a tranquil natural backdrop where a scenic pond at the edge of the land attracts birds and wildlife. The main level

Kyle Kershner Killington Pico Realty

Set on 119 acres that stretch across Andover and Chester, this property combines 114 acres in Andover with 5 in Chester. The setting includes over 20 acres of flat, open meadows along the Williams River, framed by wooded hills and distant ridgelines. The forest is mixed with possible timber value as well as a nice sugarbush waiting to be tapped. The original farmhouse, approached by a

Daire Gibney Barrett and Valley Associates Inc.

Tucked away at the end of a quiet cul-de-sac, this charming 3-bedroom, 2-bathroom log home offers the perfect blend of privacy, comfort, and convenience. Set on 3.88 acres, this property provides a peaceful retreat with easy access to everyday essentials. Step inside to find warm wood tones, spacious living areas, and classic log home character throughout. The open-concept layout is ideal for

Peggy Winchester ACORN REAL ESTATE GROUP LLC

Ledges 3--This updated 3-bedroom, 3-bath townhouse offers a welcoming retreat in the lakes region, midway between Killington and Okemo. Renovated in 2013, the home features a stylish kitchen with new cabinetry, quartz countertops, tiled backsplash, cork flooring, and quality appliances including a gas range. The main level is warm and inviting with random-width pine floors and a wood-burning

Debra Staniscia Four Seasons Sotheby's Int'l Realty

CASH FLOW POSITIVE - PRICE REDUCTION! A rare opportunity to own a piece of Vermont history - The North Pomfret Store & Post Office, c.1830. This 3-story New Englander offers charm, character, and a solid income stream on 1.84 picturesque acres. With 5 total units, the property includes 3 residential apartments (one 2-bedroom, one 1-bedroom, and an Efficiency), a ground-floor commercial office

John Bassette Bassette Real Estate Group

This 1885 antique story and a half cape has been comprehensively updated during the long ownership of the sellers who made the home more energy efficient with all new windows, recent heating system, modern kitchen and bathrooms. The home creatively blends an historic floor plan defined by a traditional living room and dining room with the more casual lifestyle of today. The open concept Vermont

Laird Bradley Williamson Group Sothebys Intl. Realty

Charming Lake Cottage with Over 113 +/-Feet of Waterfront on Lake Pauline.Lovingly maintained by the same family since the 1940s, this delightful lakefront cottage is a rare find. Step inside to discover original touches like tongue-and-groove paneling and vintage details that evoke a simpler time, all thoughtfully preserved. Modern updates blend seamlessly with its nostalgic charm and

Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

Strong Cash Flow! Profitable Investment Opportunity! This four unit multifamily property is an excellent chance for investors to add a consistent cash flowing building to their portfolio or for an on site owner occupancy and the extra rents to pay for your housing.Located in charming Wilder village on a generous .25 +/- acre in town lot. The units consist of three bedroom, two bedrooms and a

Alex DeFelice The Clerkin Agency, P.C.

Walk to the Sachem Trail from this recently remodeled, warm and charming, 2 bedroom, 2 bath, 2 level condominium. Easy maintenance with an open floor plan (kitchen, dining and living room with wood burning fireplace and slider to the deck). Updates include: new kitchen cabinets, granite countertops, wood plank flooring, carpet, and paint. The new bathrooms have large format tiling and frameless

Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

LUDLOW: Rare opportunity to own an exceptional piece of Vermont waterfront on Lake Pauline, featuring approximately 600 feet of direct shoreline and over an acre of land just minutes from Okemo Mountain Resort. Properties with this level of frontage and proximity to the water are increasingly rare, offering a unique chance to enjoy a grandfathered lakeside setting that could not be replicated

Melissa Loughan Westside Real Estate