Browse All Properties for Sale with Living/Dining

"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,...

4 Beds
4 Baths
5095057 MLS
ACTIVE Status

338 Us Route 5 S, Windsor $240,000

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 yo...

6 Beds
2 Baths
5040488 MLS
CLOSED Status

117 Black Pond Rd, Windsor $525,000

Welcome to your dream mountain retreat! This stunning 3-bedroom, 2.5-bathroom home nestled on a sprawling 16-acre lot offers the perfect blend of rustic charm & modern co...

3 Beds
3 Baths
4988658 MLS
CLOSED Status

2085 Us Route 5 S, Windsor $327,000

Brimming with character and thoughtful upgrades, this lovingly maintained turnkey Colonial offers the perfect balance of rural New England charm and everyday convenience....

3 Beds
1 Baths
5056296 MLS
CLOSED Status

149 Main St, Windsor $110,000

Behind the gated picket fence, is a 1795 dwelling waiting to be restored to its former beauty. Beautiful wooden beams and wood floors. Upon entering the dwelling, there...

2 Beds
3 Baths
4986683 MLS
CLOSED Status

2125 Rte 5 S, Windsor $245,000

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-concep...

3 Beds
1 Baths
5037505 MLS
CLOSED Status

223 Taylor Dr, Windsor $500,000

Open house, Sunday, February 18 from 11:00 to 1:00 ~ This beautiful Windsor 4-bedroom home is nestled in a quiet Vermont neighborhood and offers easy access to local shop...

4 Beds
3 Baths
4984697 MLS
CLOSED Status

25 Main St, Windsor $425,000

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...

4 Beds
2 Baths
4998054 MLS
CLOSED Status

29 Main St, Windsor $485,000

This stunning 1840's Victorian home is situated in a beautiful area of Windsor, VT. Located across from Lake Runnemede and the Windsor Town Forest, surrounded by lovely a...

4 Beds
3 Baths
4987567 MLS
CLOSED Status

30 Rocky Ledge Rd, Windsor $415,000

Beautiful Low Tax Windsor 2018 Home with Single Floor Easy Living including an Open Floorplan! 5 acres offer wooded and landscaped areas as well as a firepit and backyard...

2 Beds
1 Baths
4997701 MLS
CLOSED Status

116 Rocky Ledge Rd, Windsor $605,000

Beautiful One of a Kind Contemporary Ranch with Gorgeous Mountain Views in Low Tax Windsor!The private road leads you to this custom home that has only known one owner & ...

3 Beds
2 Baths
4992351 MLS
CLOSED Status

39 Huntington Dr, Windsor $350,000

Price Just Improved!...... Welcome to this well-maintained ranch located in the highly sought-after Juniper Terrace neighborhood. This delightful home features 3 cozy bed...

3 Beds
1 Baths
4999516 MLS
CLOSED Status

3223 County Rd, Windsor $821,500

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 boast...

4 Beds
2 Baths
5001343 MLS
CLOSED Status

43 River St, Windsor $274,000

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 wa...

4 Beds
2 Baths
5030090 MLS
CLOSED Status

18 Pine St, Windsor $370,000

Charming Victorian in a quiet neighborhood in historic Windsor, VT. Enjoy the trails in abutting Paradise Park or sip your coffee in your backyard overlooking beautiful L...

3 Beds
2 Baths
4986619 MLS
CLOSED Status

493 County Road Unit 190000.493, Windsor image

493 County Road Unit 190000.493, Windsor $239,000

Delayed showing at Open House Saturday 19th of August from 10 to 12:00 Walk to town and hiking trails, from the adorable Post and Beam constructed home. With just a few...

2 Beds
2 Baths
4965418 MLS
CLOSED Status

338 Us Route 5 S, Windsor $100,000

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 i...

3 Beds
2 Baths
4992919 MLS
CLOSED Status

42 Elm St, Windsor $275,000

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 renova...

3 Beds
2 Baths
5032968 MLS
CLOSED Status

110 Rocky Ledge Rd, Windsor $605,000

A TRUE SLICE OF HEAVEN WITH BEAUTIFUL MOUNTAIN VIEWS!This TWO/THREE BEDROOM HOME in LOW TAX Windsor is ready for its next owners!Lovingly maintained log home off the beat...

2 Beds
2 Baths
4955038 MLS
CLOSED Status

100 State St, Windsor $170,000

After 41 years with the current owners, this stately home is ready for a new generation! It will need TLC, but many of the original features are still intact. With 3 le...

6 Beds
2 Baths
4961107 MLS
CLOSED Status

119 Ascutney St, Windsor $277,000

OPEN HOUSE Saturday, June 15th 10-12 PM! Nestled on the edge of Windsor Village, this charming cape-style home has a well-maintained allure and picturesque appeal, inviti...

4 Beds
2 Baths
5000569 MLS
CLOSED Status

3 Fitch Ct, Windsor $229,000

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 o...

2 Beds
2 Baths
5036774 MLS
CLOSED Status

14 Central St, Windsor $210,000

Discover this incredibly efficient, modern home in downtown Windsor, fully updated in 2018. This turn-key property offers comfort, convenience, and contemporary living. ...

1 Beds
2 Baths
5048579 MLS
CLOSED Status

255 Channing Dr, Windsor $350,000

Extremely well maintained 3 bedroom / 2 bath ranch style home located in the Juniper Terrace neighborhood. The home offers a Buderus boiler, radiant floors, open floor pl...

3 Beds
2 Baths
5051572 MLS
CLOSED Status

31 Maple St, Windsor $215,000

PRICE REDUCTION! 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 ...

3 Beds
2 Baths
5050864 MLS
CLOSED Status

96 Dairy Ln, Windsor $400,000

OWNERS SAY SELL before Winter. Check out the new PRICE! Nestled on 1.34 picturesque acres in historic Windsor, this classic 4-bedroom Colonial blends timeless charm wit...

4 Beds
3 Baths
5054676 MLS
CLOSED Status

board logo Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .

Windsor Real Estate & Homes With Living/Dining

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Windsor, VT. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood!

Considering selling or refinancing your home? Get an INSTANT property valuation now!