View All Latest Windsor 1250+ Sq. Ft. Properties for Sale

Open House Sunday July 26th 10a.m. - 12 p.m.! Single Family or Duplex! Live in it as a spacious 3 bedroom, 2 bath single family home, or take advantage of the current ...

3 Beds
2 Baths
5100530 MLS
ACTIVE Status

145 The Plateau, Windsor $1,399,000 ▲

"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

162 Rocky Ledge Rd, Windsor $674,000

Tucked away at the end of a quiet dead-end street, this beautifully reimagined contemporary Craftsman offers the perfect blend of privacy, nature, and modern comfort. Set...

3 Beds
3 Baths
5085664 MLS
ACTIVE Status

74 Union St, Windsor $329,000 ▼

Discover space, flexibility, and everyday convenience in this charming 4-bedroom, 2-bath home in the heart of Windsor. Thoughtfully designed with a spacious floor plan, t...

4 Beds
2 Baths
5082070 MLS
ACTIVE UNDER CONTRACT 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

473 Taylor Dr, Windsor $426,000

Conveniently located from Interstate 91 and Route 5 in the Taylor Drive neighborhood sits a tidy cape home ready for its new owners. Many choices for bedrooms including...

4 Beds
3 Baths
5071233 MLS
CLOSED Status

5 Clough Ave, Windsor $60,000

Attention investors and DIY enthusiasts! Multiple exit strategies: finish this remodel then either flip, rent or move in! Home being sold as is. Cash preferred but will c...

3 Beds
1 Baths
5068975 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

68 Jarvis St, Windsor $165,000

68 Jarvis Street — a freshly painted, move-in ready 3-bedroom, 1-bath home on a double lot in downtown Windsor, Vermont. This well-kept property offers just the right amo...

3 Beds
1 Baths
5067807 MLS
CLOSED Status

10 Mckenzie Dr, Windsor $271,000

Step into the timeless appeal of this beautifully maintained 1920s home, ideally situated in the heart of Olde Windsor. The inviting front patio welcomes you into a charm...

3 Beds
2 Baths
5064694 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

3 Bavier Ave, Windsor $350,000

None

3 Beds
2 Baths
5001342 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

3 Corrigan Way, Windsor $644,000

Welcome to your serene retreat set on 6.40 acres with very low taxes, this property seamlessly combines rustic charm with modern amenities, offering the perfect blend of ...

3 Beds
3 Baths
5016032 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

205 Channing Dr, Windsor $310,000

Welcome to this inviting 2-bedroom, 1.5-bath ranch-style home located just a short distance from Main Street in Windsor, VT. Set on a manageable and sunny .29-acre lot, t...

2 Beds
2 Baths
5045341 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

918 Us Route 5 N, Windsor $325,000

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...

3 Beds
2 Baths
5018116 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

109 Morningside Dr, Windsor $254,000

This charming ranch-style home offers a perfect blend of comfort and convenience, with its spacious deck and meticulously landscaped yard providing an inviting outdoor oa...

3 Beds
2 Baths
4974792 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

32 Ascutney St, Windsor $365,000

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 sh...

4 Beds
3 Baths
5041409 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

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

153 State St, Windsor $185,000

CIRCA 1830 VINTAGE 4 BEDROOM, 2 BATH CAPE W/ FORMAL DR, FAMILY ROOM W/DECK TO FENCED YARD. CONVENIENT LOCATION TO SCHOOL, HOSPITAL, PARADISE PARK, AND VILLAGE SHOPS AND ...

4 Beds
2 Baths
4967128 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

90 Rocky Ledge Rd, Windsor $346,250

Do you enjoy sunsets? Mountain Views? Then this ranch with its 43x10 back deck will fit the bill as you experience gorgeous sunsets and mountains views all year long. ...

2 Beds
1 Baths
4988979 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

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

6 Buena Vista Ct, Windsor $305,000

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...

4 Beds
2 Baths
5008240 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

1092 Weeden Hill Rd, Windsor $134,000

~~AFFORDABLE!~~ Enjoy the peace and quiet of the countryside at 1092 Weeden Hill Road, on the West Windsor - Windsor town line. The circa 1863 Cape Cod style charmer has ...

3 Beds
2 Baths
4971437 MLS
CLOSED Status

37 Morningside Dr, Windsor $405,000

Price Just Improved! Discover your dream home nestled in a serene neighborhood! This charming 3-bedroom Cape Cod-style house sits on a spacious 1.15-acre lot adorned with...

3 Beds
2 Baths
5001571 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

17 Dewey Ave, Windsor $119,000

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...

3 Beds
1 Baths
5015596 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

66 Union St, Windsor $219,000

PRICE JUST IMPROVED! Welcome to this beautifully maintained New Englander nestled in the historic town of Windsor — Vermont's first capital and a gem of the Upper Valley....

3 Beds
2 Baths
5042811 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

18 County Rd, Windsor $325,000

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 ha...

3 Beds
2 Baths
5022365 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

8 Old Mill Pond Rd, Windsor $305,000

None

3 Beds
5 Baths
5058744 MLS
CLOSED Status

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1250+ Sq. Ft. Windsor Real Estate

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