View All Latest Windsor 2250+ Sq. Ft. Properties for Sale

"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

93 Belaski Rd, Windsor $560,000

Exceptional Cape in Historic Windsor: Pool, Views & In-Law Suite Welcome home to this impeccably maintained Cape-style residence, where timeless charm meets modern elega...

3 Beds
3 Baths
5090593 MLS
PENDING Status

2 Pine St, Windsor $510,000 ▼

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...

6 Beds
4 Baths
5089288 MLS
ACTIVE Status

273 Rte 5 N, Windsor $413,900 ▼

Motivated Seller - Price Improved! Own a remarkable piece of Vermont history in the heart of Windsor. Built circa 1790, this beautifully preserved brick-and-frame Colonia...

4 Beds
3 Baths
5080622 MLS
ACTIVE Status

64 State St, Windsor $425,000

Windsor’s income-producing potential meets turnkey ease in this updated five-unit multifamily, perfectly positioned in Vermont’s historic “Birthplace of Vermont” along th...

5079828 MLS
CLOSED Status

223 Taylor Dr, Windsor $530,000

This lovely home has plenty of sunny light filled space. Home features a large kitchen/eating area, with a formal-sized dining room, and spacious living room. First floor...

4 Beds
3 Baths
5072087 MLS
CLOSED Status

2545 County Rd, Windsor $230,000

Welcome to 2545 County Road in Windsor, Vermont! This inviting 3-bedroom, 2-bath raised ranch offers over 2,200 square feet of comfortable living space on a picturesque o...

3 Beds
2 Baths
5068382 MLS
CLOSED Status

3-5 Foster Ave, Windsor $235,000

Welcome to 3-5 Foster Avenue – A Rare Opportunity with Generational Charm Lovingly cared for by the same owner for over 77 years, this classic duplex is full of warmth, c...

5044374 MLS
CLOSED 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

30 Union St, Windsor $350,000

Step into timeless elegance with this grand Victorian home, beautifully situated on a charming in-town lot. This stately residence showcases stunning hardwood floors thro...

4 Beds
5 Baths
5018205 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

9 Main St, Windsor $200,001

A Grand Old Home Full of Character and Potential What a beauty this home once was—and can be again! Brimming with historic charm, this spacious residence is just waiting...

4 Beds
2 Baths
5052179 MLS
CLOSED Status

17 Clough Ave, Windsor $239,900

OFFERS due Thursday, 8-3-23 at 6pm. Location, location, location. Come tour 17 Clough Avenue, nestled into a quiet neighborhood just a few minutes walk to downtown, the ...

4 Beds
2 Baths
4963151 MLS
CLOSED Status

40 Village Grn, Windsor $350,000

Whether you're looking to invest or settle in with the family, this property offers the perfect blend of comfort, convenience, and community. *4 Units: 3 Cozy 1-Bedroom ...

4986017 MLS
CLOSED Status

9 Durkee St, Windsor $175,000

Let this rooming house be your next great investment. 10 rooms, and a 2 bedroom apartment. Some long term renters. Rooms still available, and new boiler just installed.

4995534 MLS
CLOSED Status

51-53 River St, Windsor $230,000

This is a great investment for income, or live in the main dwelling and rent the two apartments with good rental history. Plenty of space, large fenced-in backyard with ...

4971110 MLS
CLOSED Status

77 Taylor Dr, Windsor $335,000

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 ...

5027791 MLS
CLOSED Status

108 Main St, Windsor $310,000

This charming piece of VT history was originally built as an apothecary in 1804. Now it's a charming, fully occupied, four unit multi-family building consisting of three...

4955144 MLS
CLOSED Status

1528 Rte 5 S, Windsor $1,640,000

Extraordinary opportunity to own one of the 'finest homes in the Upper Valley' formerly known as 'Gilnocky Farm' located in Windsor, the 'Birthplace of Vermont' is privat...

6 Beds
7 Baths
4949295 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

2460 Rte 5n, Windsor $140,000

Are you ready for your first house hack? Or maybe you have done this many times.....! This is the perfect home to gain sweat equity and have a tenant pay your mortgage. N...

5 Beds
2 Baths
4963258 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

36 River St, Windsor $240,000

None

5037578 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

2768 Hunt Rd, Windsor $1,350,000

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 offere...

3 Beds
3 Baths
5001669 MLS
CLOSED Status

2446 Us Route 5 N, Windsor $306,000

This beautifully updated 4-bedroom, 2-bath New England Colonial, nestled in a friendly neighborhood, combines classic charm with modern convenience. Step inside to discov...

4 Beds
2 Baths
5019027 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

480 Rte 5, Windsor $210,000

This home has been in the same family for the last 54 years. Originally built in 1780, it has had some additions over the years. Situated on a parcel of 12.4 acres, it ha...

4 Beds
3 Baths
4936596 MLS
CLOSED Status

2460 Rte 5n, Windsor $155,000

Are you ready for your first house hack? Or maybe you have done this many times.....! This is the perfect home to gain sweat equity and have a tenant pay your mortgage. ...

4963168 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

1124 Rte 5 S, Windsor $380,000

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...

5009762 MLS
CLOSED Status

102-104 State St, Windsor $250,000

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 a...

5028181 MLS
CLOSED Status

70-74 State St, Windsor $115,000

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 resid...

5 Beds
4 Baths
4953869 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 .

2250+ Sq. Ft. Windsor Real Estate

Our website features the best real estate search for 2250+ sq. ft. properties available in Windsor and surrounding areas. 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!