Recently Sold Windsor Homes

A Grand Old Home Full of Character and PotentialWhat a beauty this home once was—and can be again! Brimming with historic charm, this spacious residence is just waiting for someone to restore it to its full glory. From the high ceilings and rich pecan woodwork to the elegant crown moldings and soapstone countertops, the original details create a timeless backdrop for your

Linda Benoit Highland Realty

Welcome to this rejuvenated home with one car garage with recent updates including fresh paint and flooring, new kitchen counter tops and cabinets and light fixtures. There’s good interior space with a living room, dining room, family room, second floor laundry and 3 bedrooms upstairs as well as an enclosed front porch for evening relaxing. This is a great opportunity and should be on your short

Susan Bellville Bellville Realty

Nestled in a peaceful rural setting, this roomy 4-bedroom, 3-bathroom home offers incredible potential for those looking to create their dream country home. While the property is in need of some work, it features a generous layout and sits on a little over an acre, which allows for plenty of space to enjoy the beautiful setting. The home features hardwood floors, vinyl windows, a pellet stove, as

Jenn Boyer Coldwell Banker Homes Unlimited

Discover this incredibly efficient, modern home in downtown Windsor, fully updated in 2018. This turn-key property offers comfort, convenience, and contemporary living.Step inside to find all main living areas thoughtfully located on the second floor. The primary bedroom boasts an oversized, ensuite bathroom with a spacious walk-in shower, providing a private oasis. The kitchen is a

David White OwnerEntry.com

Imagine waking to the soft glow of dawn filtering through the windows of your charming three-story farmhouse, nestled in the heart of Vermont’s historic birthplace. As you sip coffee in the sunlit kitchen, the Connecticut River glimmers across the street, promising a day of serenity. This -bedroom, 2-bath home, brimming with character, becomes your sanctuary.Upstairs, the tranquil bedrooms

Kevin Holmes Blue Slate Realty

Welcome to 3-5 Foster Avenue – A Rare Opportunity with Generational CharmLovingly cared for by the same owner for over 77 years, this classic duplex is full of warmth, character, and potential. Nestled on a quiet dead-end street, each unit offers 3 spacious bedrooms, inviting covered porches, and generous living space perfect for relaxing or entertaining. The fenced-in backyard is ideal for

Raelene Robinson-Garrow KW Vermont Woodstock

Great Location! Well-Maintained! 4BR's Cape Full Basement with work bench, Many recent updates in the last three years, Rear deck, Garden area and Private backyard.

Don Chabot Town and Country Realty

Ready for the next generation is this lovingly cared for New Englander.Nestled on a quiet side street in the heart of Windsor, VT, this classic 2-bedroom, 2-bath home offers both character and warmth. The inviting front porch welcomes you into a sunlit living space featuring hardwood floors, original woodwork, and large windows that let in plenty of natural light.The spacious

Katie Ladue Gilbert KW Vermont Woodstock

This home is ideal for a builder, investor or new homeowner who can qualify for a conventional or construction loan. Sale price includes a variety of building materials. The home appears structurally sound with a 3 zone hot water heating system, drilled well and public sewer. This property features an attached 1 car garage or a heated workshop, 3 BR's, 1.5 baths, office, fireplaced LR /with

Don Chabot Town and Country Realty

OFFER DEADLINE: 3/27/2025 at 2pm.Nestled in the heart of Windsor, VT, this delightful 3-bedroom, 2-bathroom home offers classic New England charm with many recent renovations. Situated in a desirable in-town location, this two-story home boasts a welcoming front porch, perfect for relaxing with your morning coffee.Inside, you'll find a warm and inviting layout. The entry way provides a place for

Katie Ladue Gilbert KW Vermont Woodstock

With fabulous curb appeal and a welcoming covered porch, this turn-key circa 1940 New England home beautifully blends timeless design with modern comfort. The open-concept kitchen and dining area flow seamlessly into spacious living areas, creating a warm and inviting atmosphere. Elegant features such as French doors, a fireplace with a classic brick hearth, and bay windows add character and

Katie Ladue Gilbert KW Vermont Woodstock

A stellar combination and flexible to your needs. This 3 unit building situated on a large lot includes workshops, storage for tenants, and /or covered parking. Included is a single family manufactured home for additional income or a great spot to build a 2 bedroom cottage / tiny home. Great property for rental income or make this a family compound. Just north of town there is ample lawn for

Katie Ladue Gilbert KW Vermont Woodstock

OFFER DEADLINE: MONDAY 4/21/25 6pmReady to start your real estate investment journey? This 3-bedroom home is the perfect opportunity for someone eager to build equity and willing to add their own personal touch. Upstairs, you’ll find three spacious bedrooms and a convenient half bath—ideal for families or future tenants.The eat-in kitchen is ready for your updates, offering a blank canvas to

Katie Ladue Gilbert KW Vermont Woodstock

Step into timeless elegance with this grand Victorian home, beautifully situated on a charming in-town lot. This stately residence showcases stunning hardwood floors throughout, preserving its classic heritage while offering modern comforts. The spacious first-floor bedroom features an en suite bath, providing both luxury and convenience. A cozy fireplace adds warmth and character to the main

Katie Ladue Gilbert KW Vermont Woodstock

Old Mill Pond Condominiums offer an idyllic haven in the heart of Windsor. Imagine enjoying mountain views, pond access, and amenities such as an in-ground pool and tennis courts.This unit features vaulted ceilings and unique architectural elements often missing in typical condominiums. Guests can relax by the cozy fireplace or on the spacious deck with mountain views, depending on the

Julie Davis KW Vermont Woodstock

Charming & spacious home with timeless character. Step into a home where classic charm meets modern convenience! From the moment you enter, you'll be captivated by the warmth of the hardwood floors, wide trim, built-ins, and soaring ceilings that create an inviting and spacious atmosphere. The generously sized rooms effortlessly accommodate daily life, while the enclosed three-season porch

Katie Ladue Gilbert KW Vermont Woodstock

Nicely located just walking distance to the school and town amenities. Nice level lot with home just waiting for you to make it your own. Three bedrooms and spacious main level.

Dorothy Griswold The Clerkin Agency, P.C.

Enjoy all the conveniences of Village life, with a tranquil view of rolling green horse pastures right from your window. This absolutely-charming antique New Englander has one of the best locations in town. Just outside your back door you'll enter the 200 AC Paradise Park nature trail network, complete with ponds, waterfalls, vernal pools and wildlife. The house is tidy, efficient, and lovingly

Danny Kogut Williamson Group Sothebys Intl. Realty

Welcome home to this inviting 3-bedroom, 1-bath ranch-style gem nestled in one of Windsor’s most sought-after neighborhoods. Step inside to find a cozy living room with a beautiful fireplace, perfect for New England winters. The kitchen opens into the dining room, and could be your chance at a fun remodel. Each bedroom provides comfort and plenty of natural light, making it a warm retreat for

Katie Ladue Gilbert KW Vermont Woodstock

Built in 1796, the historic Trask House is located on beautiful Main St. in the heart of downtown Windsor. The center hall Federal sits on just under 1/2 acre and has an attached barn/garage in the back with plenty of storage. There is a private brick patio surrounded by a white picket fence and lovely landscaping. Inside, you are greeted by large open rooms with hardwood floors, high ceilings,

Dan Noble Snyder Donegan Real Estate Group

This beautifully updated 4-bedroom, 2-bath New England Colonial, nestled in a friendly neighborhood, combines classic charm with modern convenience. Step inside to discover a warm and inviting oversized mudroom, seamlessly flowing into a bright kitchen featuring a custom island and an abundance of cabinetry for all your storage needs. Just off the kitchen, the graciously sized dining room is

Livian Vermont KW Vermont

Nestled just off the main road, this charming split-level home offers the perfect blend of privacy and convenience. Located just moments from town, you'll enjoy the peaceful setting without sacrificing easy access to local amenities. The inviting living room features a large picture window, filling the space with natural light. The adjacent kitchen includes a cozy dining area, ideal for family

Katie Ladue Gilbert KW Vermont Woodstock

Discover your dream home in this beautifully renovated 3-bedroom, 2-bath split-level residence, nestled in the serene landscapes of Windsor. This move-in-ready gem boasts a host of modern updates, making it the perfect blend of comfort and style. Step inside to a welcoming heated mudroom that leads you into the spacious living area, adorned with stunning hardwood floors and vaulted ceilings that

Livian Vermont KW Vermont

Don’t scroll past this listing without flipping through all the pictures! This turn-key 1988 ranch with a full concrete basement and attached garage in a quiet cul-de-sac neighborhood located in Windsor, Vermont is calling your name! Move right in with ease as the property is available now. Live comfortably on the main level with three bedrooms and two full bathrooms, plus the downstairs has

Krista Harness Heney Realtors - Element Real Estate (Montpelier)

Come check out this very cute diamond in the rough! This home offers 2 good sized bedrooms with huge closets and a primary with a deck off the bedroom, as well as potential for a en suite bathroom....Several possibilities for the downstairs as well....Along with a 2 car garage with possible furnace hook up and its own electrical panel. This property is convenient to in town amenities and all that

Jenn Boyer Coldwell Banker Homes Unlimited

Back on the market. Did you miss this one in the first round? Completely Remodeled! This stunning home has undergone a total makeover, emerging as a beautiful, clean, and charming retreat in a lovely neighborhood. With nothing left to do but move in and enjoy, this 3+ bedroom residence boasts a brand-new kitchen, updated bathroom, and a newly restored mudroom entry and deck with laundry and 1/2

Katie Ladue Gilbert KW Vermont Woodstock

Step into this beautifully taken care of vintage charmer, where classic Vermont character meets modern comfort. The home's original features are intact, including stunning maple hardwood floors and a striking tiger eye maple staircase that captures the essence of timeless elegance. The kitchen is a perfect blank canvas to add in your own personal touches. Enjoy the serenity of the seasons on

Katie Ladue Gilbert KW Vermont Woodstock

Price Just Improved!...... Welcome to this well-maintained ranch located in the highly sought-after Juniper Terrace neighborhood. This delightful home features 3 cozy bedrooms and 1 full bath, perfect for comfortable living. The inviting living area is complemented by a pellet stove, providing warmth and ambiance during the cooler months. The highlight of this home is the finished basement,

Katie Ladue Gilbert KW Vermont Woodstock

This property is the perfect fit if you are new to home ownership and would like to have a portion of your mortgage paid monthly. The main home is 3 bedrooms, 3 bathrooms, new deck, spacious yard, and updated appliances. The 1 bedroom unit has a nice enclosed porch, adding seasonal living space, and has been renovated. There is also storage space above that could be added to this unit. In the

Katie Ladue Gilbert KW Vermont Woodstock

Welcome to this exquisite four-bedroom, two-bathroom Colonial home, built in 1801, nestled on a sprawling 10.4-acre lot in Windsor, Vermont. This charming residence boasts maple and bamboo floors as well as original wide pine flooring, spacious bedrooms, and tiled bathrooms. The property includes a two-bedroom, one-bathroom ADU, perfect for generating rental income or accommodating guests. Enjoy

Kate Cassidy Four Seasons Sotheby's Int'l Realty

Charming Cape with a spacious L addition and attached barn with storage above. Features include 3 bedrooms and a full bath upstairs, and a bedroom with a half bath on the first floor (just needs a door). Enjoy a 22x12 front living room with beautiful old wood floors, a remodeled kitchen with newer stainless appliances and a walk-in pantry, and a sunny dining room with built-ins. The private,

Deb Roberts RE/MAX Upper Valley

Fox Penny Farm, an established horse farm on 62 acres of open fields, trails, and woods on the Windsor/West Windsor line with westerly views of Mt Ascutney, is now offered for sale. Offering an expansive 3-bedroom 2.5 baths colonial with light-filled spaces, hardwood floors, spacious kitchen, dining room & propane fireplaced living room. Upstairs provides three large bedrooms with a primary

Scott Monahan Williamson Group Sothebys Intl. Realty

Spacious and affordable 3-story dwelling in Windsor. Buy it as a starter home, or take the opportunity for renovation and rental or resale. Pleasant stone landscaping in the yard. A kitchenette is found in the 3rd floor apartment (perhaps a rental unit or an in-law suite?) There's proximity to shopping (including a fine glass store, brewery, distillery, and jam shop), Amtrak, Mount Ascutney

Zachary Zupan EXP Realty

This inviting 4-bedroom, 3-bath colonial home offers the perfect blend of traditional charm and modern convenience. Located on a 0.33-acre lot, this property is just a short distance from town, providing easy access to shops, restaurants, and more while maintaining a peaceful residential feel.

Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

Katie Ladue Gilbert KW Vermont Woodstock

Katie Ladue Gilbert KW Vermont Woodstock

Allison Griep KW Vermont Woodstock