Waterfront homes for sale & real estate in Windsor County, VT

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ABOUT THIS HOME
Waterfront Home for sale in Windsor County, VT:
A circa 1734 Cape, displaying museum quality authentic detailing, in a setting worthy of a Vermont Life Magazine cover! Originally sited in N. H. , the Cape was patiently dismantled, with components meticulously cataloged, and then relocated to an idyllic Vermont hilltop setting! The interior seamlessly blends early New England architectural features with benefits of contemporary design amenities. Authentic post and beam construction, gunstock corner posts, exposed beams, extraordinary wide board floors, 4 brick fireplaces, wide board sheathing and hand planed surfaces are desirable components! The advantage of contemporary mechanical systems, a full size cement basement and whole house bac

$3,490,000

4 beds4.5 baths2,894 sq ft

1726 Skitchewaug Trl, Springfield, VT 05156

Wide board floors • Brick fireplaces • Cement basement

ABOUT THIS HOME
Waterfront Home for sale in Windsor County, VT:
Upper Farm- Circa 1799, large antique cape nestled on 12 acres with stream, multiple ponds, stunning waterfalls overlooking a large meadow. Beautiful extensive gardens for all those perennial enthusiasts with multiple stone terraces overlooking an apple orchard with a variety of types of apples. A two level barn for equipment/storage/animals. A brand new expansive 3 bay heated garage with multiple car lifts to hold a total of 8 cars. Second floor hosts a handsome 1 bedroom apt with deck. The primary residence has handsome wide pine floors throughout- exceptional craftsmanship. A vast kitchen fit for a chef- large island, stone counters with high end appliances- massive pantry with 1/2 bat

$2,895,000

5 beds7 baths8,249 sq ft

1497 Bowman Rd, South Royalton, VT 05031

Extensive gardens • Stunning waterfalls • Multiple ponds

VIDEO TOUR

ABOUT THIS HOME
Waterfront Home for sale in Windsor County, VT:
Downtown Ludlow Convenience - Welcome to Mill #212, a beautifully updated condo in the heart of Ludlow. Just minutes to Okemo Mountain and directly on the shuttle route, this furnished unit combines comfort with convenience. Inside, you’ll find exposed beams, modern updates throughout, and an open living space that flows seamlessly to a private deck overlooking the Black River. Enjoy the ease of being steps from shops, dining, and village amenities while still feeling tucked away. With a proven rental history, this home offers excellent rental potential as well as a perfect Vermont retreat. Visit the Okemo real estate community today. Taxes are based on the town assessment.

$220,000

2 beds1.5 baths1,019 sq ft

145 Main St #212, Ludlow, VT 05149

Private deck • Rental potential • Steps from shops

ABOUT THIS HOME
Waterfront Home for sale in Windsor County, VT:
Step into the charm of this antique home, offering an abundance of potential for restoration and customization. Highlights include beautiful wide board floors and a quiet, private backyard set on just under an acre. Ideal for buyers ready to take on a project and bring this special property back to life. Cash only buyers.

$165,000

3 beds1 bath1,554 sq ft

89 route 12, Hartland, VT 05048

Two master suites • Private balcony • Babbling brook

ABOUT THIS HOME
Waterfront Home for sale in Windsor County, VT:
Welcome to "Valley Brook Farm", a Historic Cape in the middle of Horse country on 12.92 acres with Barns, rolling & level Pasture, a swimming Pond, and Brook. Located in the heart of the nationally renowned Green Mountain Horse Association trail network. Nestled on scenic & bucolic Jenneville Road, this c. 1820 Cape offers the warmth of wide pine floors, post-and-beam character, and sun-filled spaces. The 1.75-story home (2,212+ sq ft) includes 4 bedrooms and 2 full baths. The charming country kitchen features an expansive Family Room area and breakfast nook with a view of the rear meadows. The adjoining pantry, pellet stove, and coat closet make for practical Vermont

$635,000

4 beds2 baths2,212 sq ft

298 Jenneville Rd, Hartland, VT 05048

Swimming pond • 12.92 acres • Barns

Property at 1607 Massey Rd, Springfield, VT 05156, 4 beds, 2 baths

$895,000

4 beds2 baths4,144 sq ft

1607 Massey Rd, Springfield, VT 05156

Property at 3914 South Rd, Woodstock, VT 05071, 4 beds, 3 baths

$725,000

4 beds3 baths3,584 sq ft

3914 South Rd, Woodstock, VT 05071

Property at 3019 Popple Dungeon Rd, Chester, VT 05143, 1 bed, 1 bath

$169,000

1 bed1 bath200 sq ft

3019 Popple Dungeon Rd, Chester, VT 05143

Property at 198 Depot St, Proctorsville, VT 05153, 5 beds, 3 baths

$415,000

5 beds3 baths1,976 sq ft

198 Depot St, Proctorsville, VT 05153

Property at 696 Route 100 N, Ludlow, VT 05149, 2 beds, 1 bath

$415,000

2 beds1 bath1,100 sq ft

696 Route 100 N, Ludlow, VT 05149

Property at 9 Fairview St, Springfield, VT 05156, 4 beds, 1.5 baths

$200,000

4 beds1.5 baths1,482 sq ft

9 Fairview St, Springfield, VT 05156

Property at 2140 Brandon Mountain Rd, Rochester, VT 05767, 3 beds, 1.5 baths

$499,000

3 beds1.5 baths2,656 sq ft

2140 Brandon Mountain Rd, Rochester, VT 05767

Property at 254 Town Line Rd, Plymouth, VT 05056, 4 beds, 3.5 baths

$2,499,000

4 beds3.5 baths5,079 sq ft

254 Town Line Rd, Plymouth, VT 05056

Property at 35 Stevens Rd, Cavendish, VT 05142, 4 beds, 3 baths

$674,000

4 beds3 baths3,100 sq ft

35 Stevens Rd, Cavendish, VT 05142

Property at 228 Leonard Rd, Sharon, VT 05065, 3 beds, 2.5 baths

$739,000

3 beds2.5 baths2,235 sq ft

228 Leonard Rd, Sharon, VT 05065

Property at 2346 Quechee Main St, White River Junction, VT 05059, 3 beds, 3.5 baths

$1,865,000

3 beds3.5 baths3,827 sq ft

2346 Quechee Main St, White River Junction, VT 05059

Property at 505 Deweys Mills Rd, Hartford, VT 05047, 6 beds, 5 baths

$1,400,000

6 beds5 baths4,571 sq ft

505 Deweys Mills Rd, Hartford, VT 05047

Property at 121 E Lake Rd, Ludlow, VT 05149, 3 beds, 1 bath

$425,000

3 beds1 bath895 sq ft

121 E Lake Rd, Ludlow, VT 05149

Property at 1500 Brownsville Hartland Rd, West Windsor, VT 05089, 2 beds, 1 bath

$115,000

2 beds1 bath720 sq ft

1500 Brownsville Hartland Rd, West Windsor, VT 05089

Property at 145 Main St #210, Ludlow, VT 05149, 2 beds, 1 bath

$215,000

2 beds1 bath892 sq ft

145 Main St #210, Ludlow, VT 05149

Property at 1300 Mountain Rd, Ludlow, VT 05149, 4 beds, 5 baths

$2,000,000

4 beds5 baths2,887 sq ft

1300 Mountain Rd, Ludlow, VT 05149

Property at 228 Cavendish Gulf Rd, Cavendish, VT 05495, 3 beds, 2 baths

$395,000

3 beds2 baths1,312 sq ft

228 Cavendish Gulf Rd, Cavendish, VT 05495

Property at 222 River St, Bethel, VT 05032, 3 beds, 2 baths

$215,000

3 beds2 baths2,121 sq ft

222 River St, Bethel, VT 05032

Property at 652 Tierney Rd, Cavendish, VT 05142, 4 beds, 3.5 baths

$1,499,000

4 beds3.5 baths3,560 sq ft

652 Tierney Rd, Cavendish, VT 05142

Property at 6852 US Route 4, Bridgewater, VT 05034, 3 beds, 2 baths

$449,000

3 beds2 baths1,489 sq ft

6852 US Route 4, Bridgewater, VT 05034

Property at 515 Shattuck Hill Rd Unit 515, 513 & 511, West Windsor, VT 05037, 6 beds, 5.5 baths

$1,450,000

6 beds5.5 baths4,225 sq ft

515 Shattuck Hill Rd Unit 515, 513 & 511, West Windsor, VT 05037

Property at 61 Academy Cir, South Woodstock, VT 05071, 6 beds, 5 baths

$3,500,000

6 beds5 baths5,433 sq ft

61 Academy Cir, South Woodstock, VT 05071

Property at 1104 Main St, Cavendish, VT 05142, 3 beds, 4 baths

$895,000

3 beds4 baths3,590 sq ft

1104 Main St, Cavendish, VT 05142

Property at 23-25 Depot St, Ludlow, VT 05149, 11 beds, 6 baths

$749,000

11 beds6 baths6,000 sq ft

23-25 Depot St, Ludlow, VT 05149

Property at 234 Randall Rd, Woodstock, VT 05091, 2 beds, 1 bath

$845,000

2 beds1 bath600 sq ft

234 Randall Rd, Woodstock, VT 05091

Property at 476 Missing Link Rd, Springfield, VT 05156

$175,000

— beds— baths— sq ft

476 Missing Link Rd, Springfield, VT 05156

Property at 00 Chateauguay Rd, Barnard, VT 05031

$299,000

— beds— baths— sq ft

00 Chateauguay Rd, Barnard, VT 05031

Property at 911 Waterman Rd, South Royalton, VT 05068

$349,000

— beds— baths— sq ft

911 Waterman Rd, South Royalton, VT 05068

Property at 0 Walker Hill Rd, Bridgewater, VT 05034

$835,000

— beds— baths— sq ft

0 Walker Hill Rd, Bridgewater, VT 05034

Property at 0 Barnard Rd Unit 20.002, Woodstock, VT 05091

$779,000

— beds— baths— sq ft

0 Barnard Rd Unit 20.002, Woodstock, VT 05091

Property at 95 Jenne Rd, Hartland, VT 05048-0349

$275,000

— beds— baths— sq ft

95 Jenne Rd, Hartland, VT 05048-0349

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Waterfront Homes for Sale in Windsor County

There are currently 36 waterfront homes for sale in Windsor County at a median listing price of $549K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Windsor County stay on the market for 102 days. This map is refreshed with the newest listings in Windsor County every 15 minutes.

In the past month, 87 homes have been sold in Windsor County. In addition to houses in Windsor County, there were also 94 condos, 4 townhouses, and 27 multi-family units for sale in Windsor County last month. Find your dream home in Windsor County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Windsor County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Windsor County. If you're looking to sell your home in the Windsor County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Windsor County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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Copyright 2026 PrimeMLS All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this website comes in part from the VOW Program of PrimeMLS. Data last updated Sat Jan 03 2026 on the search page

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Waterfront homes for sale & real estate in Windsor County, VT

Waterfront Homes for Sale in Windsor County

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