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

127 homes

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ABOUT THIS HOME
Luxury Home for sale in Windsor County, VT:
They say land remembers. On Rush Meadow Road-where rolling fields meet the quiet rhythm of the seasons-there is a place that has been held, cared for, and passed down for over a century. This 103-acre estate is not something that was assembled. It was lived. Worked. Protected. For generations, it operated as a dairy farm, and the land still reflects that stewardship—lush hayfields, a ready-to-tap sugarbush, rich soil for gardening and beautiful solar exposure across every acre. It’s the kind of property that continues to give, year after year. At its heart sits a classic Vermont farmhouse with 3 bedrooms and 1.5 baths, grounded by its traditional woodshed ell and surrounded by s

$1,450,000

3 beds1.5 baths1,360 sq ft

1503 Rush Meadow Rd, West Windsor, VT 05037

Long range views • Lush hayfields • 103 acre estate

3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Windsor County, VT:
"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, mature trees, beautiful gardens, and a protected front-and-center view of Mt. Ascutney to the West and the Connecticut River to the East. This private peaceful setting includes an inground pool for those hot summer days, and two porches: one open air and one screened-in, with views into the New Hampshire hillsides. Inside, the house is open and bright with a wonderful flow throughout. The large living room features a wood-burning fireplace and plenty of windows streaming in lots of natural light. The formal dinin

$1,399,000

4 beds3.5 baths4,000 sq ft

145 The Plateau, Windsor, VT 05089

Private road • Screened-in porch • Built-in cabinets

ABOUT THIS HOME
Luxury Home for sale in Windsor County, VT:
Set on 157 private acres with sweeping long-range views of the Connecticut River, this meticulously restored circa 1735 Cape offers a rare blend of historic character, refined comfort, and estate-scale amenities. Completely dismantled and rebuilt with care, the post-and-beam residence displays exposed beams, wide-board floors and sheathing, gunstock corner posts, and classic brick fireplaces alongside thoughtful modern upgrades. The inviting, renovated kitchen features an oversized fireplace, high-end appliances, and expansive views of the swimming pond and distant views of the Connecticut River. Three en-suite bedrooms include a gracious first-floor primary suite enhanced by a 30-by-20-foo

$2,790,000

4 beds4.5 baths2,894 sq ft

1726 Skitchewaug Trl, Springfield, VT 05156

Private acres • High-end appliances • Long-range views

ABOUT THIS HOME
Luxury Home for sale in Windsor County, VT:
SPRING HILL FARM– A Storied Vermont Estate with Timeless Appeal. Set amidst the rolling hills of Barnard, Vermont, Spring Hill Farm is a distinguished country estate where historic charm and thoughtful stewardship come together across 207 acres of beautifully maintained landscape. Anchoring the property is a stately brick residence dating to 1795, offering a refined sense of heritage and permanence. A later addition introduces a striking post-and-beam great room, with soaring cathedral ceilings and a fieldstone fireplace that brings warmth, scale, and a sense of rustic elegance to the home’s traditional architecture. The result is a sophisticated yet approachable interior, ideal

$2,195,000

3 beds3 baths2,997 sq ft

9671 VT Route 12, Barnard, VT 05031

Manicured ponds • Fieldstone fireplace • Cathedral ceilings

ABOUT THIS HOME
Luxury Home for sale in Windsor County, VT:
Did I read that right? 172 acres?! Impeccably renovated farmhouse on +-172 acres - what more could you ask for? ~131 acres of this property are located in Cavendish while the other ~41 are in Reading. Enjoy apples straight from the backyard. Listen and watch the brook babble down by the road and enjoy the peace that comes from this lovely home. All new Marvin Elevate windows, all new appliances, new plumbing, new boiler, new electrical panel, new lighting, new paint, new spray foam insulation, new concrete poured in the basement. No detail was too small. All the work has been done so you can simply move in and enjoy. With 4 bedrooms plus an office there is plenty of space for everyone to fe

$1,200,000

4 beds2 baths1,908 sq ft

366 Knapp Pond Rd, Cavendish, VT 05142

172.26 acre lot • 2 garage spots • Built 1860

Property at 240 Ghia Farm Rd, Ludlow, VT 05149, 5 beds, 3 baths

$1,150,000

5 beds3 baths3,065 sq ft

240 Ghia Farm Rd, Ludlow, VT 05149

Property at 72 Wood Rd, Hartford, VT 05001, 3 beds, 2 baths

$1,300,000

3 beds2 baths2,334 sq ft

72 Wood Rd, Hartford, VT 05001

Property at 41 Pleasant St, Woodstock, VT 05091, 9 beds, 11 baths

$2,599,000

9 beds11 baths5,993 sq ft

41 Pleasant St, Woodstock, VT 05091

Property at 110 Main St, Ludlow, VT 05149

$850,000

— beds— baths3,382 sq ft

110 Main St, Ludlow, VT 05149

Property at 55 Cherry Hl, Springfield, VT 05156, 6 beds, 4.5 baths

$2,300,000

6 beds4.5 baths8,656 sq ft

55 Cherry Hl, Springfield, VT 05156

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

$1,275,000

6 beds5 baths4,571 sq ft

505 Deweys Mills Rd, Hartford, VT 05047

Property at 399 Bentley Rd, Hartford, VT 05059, 5 beds, 3.5 baths

$1,490,950

5 beds3.5 baths3,358 sq ft

399 Bentley Rd, Hartford, VT 05059

Property at 924 Okemo Ridge Rd Unit S 11, Ludlow, VT 05149, 7 beds, 6.5 baths

$4,775,000

7 beds6.5 baths6,624 sq ft

924 Okemo Ridge Rd Unit S 11, Ludlow, VT 05149

Property at 726 E Ash Rd, Plymouth, VT 05056, 6 beds, 7.5 baths

$850,000

6 beds7.5 baths5,588 sq ft

726 E Ash Rd, Plymouth, VT 05056

Property at 325 Cemetery Rd, West Windsor, VT 05089, 4 beds, 2 baths

$1,325,000

4 beds2 baths2,554 sq ft

325 Cemetery Rd, West Windsor, VT 05089

Property at 320 Okemo Trailside Ext Unit 36E, Ludlow, VT 05149, 3 beds, 3.5 baths

$1,100,000

3 beds3.5 baths1,796 sq ft

320 Okemo Trailside Ext Unit 36E, Ludlow, VT 05149

Property at 1354 Vermont Route 100, Stockbridge, VT 05772, 3 beds, 2.5 baths

$850,000

3 beds2.5 baths4,088 sq ft

1354 Vermont Route 100, Stockbridge, VT 05772

Property at 310 Pierce Hill Rd, Brownsville, VT 05037, 7 beds, 5 baths

$1,295,000

7 beds5 baths5,774 sq ft

310 Pierce Hill Rd, Brownsville, VT 05037

Property at 51 E Ash Rd, Plymouth, VT 05056, 7 beds, 8.5 baths

$2,650,000

7 beds8.5 baths13,410 sq ft

51 E Ash Rd, Plymouth, VT 05056

Property at 196 Cowdrey Outlook, Bethel, VT 05032, 3 beds, 1 bath

$1,595,000

3 beds1 bath1,708 sq ft

196 Cowdrey Outlook, Bethel, VT 05032

Property at 26 Mt Peg Rd Unit B, Woodstock, VT 05091, 3 beds, 3.5 baths

$875,000

3 beds3.5 baths2,584 sq ft

26 Mt Peg Rd Unit B, Woodstock, VT 05091

Property at 191 Moon Shadow Dr Unit M19, Ludlow, VT 05149, 5 beds, 6.5 baths

$3,250,000

5 beds6.5 baths5,728 sq ft

191 Moon Shadow Dr Unit M19, Ludlow, VT 05149

Property at 292 Okemo Trailside Ext Unit 34E, Ludlow, VT 05149, 4 beds, 2.5 baths

$1,100,000

4 beds2.5 baths1,842 sq ft

292 Okemo Trailside Ext Unit 34E, Ludlow, VT 05149

Property at 76 Goldthwaite Rd, Chester, VT 05143, 4 beds, 3 baths

$1,200,000

4 beds3 baths3,308 sq ft

76 Goldthwaite Rd, Chester, VT 05143

Property at 1589 Main St, Cavendish, VT 05142, 10 beds, 10 baths

$1,400,000

10 beds10 baths7,153 sq ft

1589 Main St, Cavendish, VT 05142

Property at 37 Village Center Rd Unit Blue Spruce 4, Ludlow, VT 05149, 4 beds, 4 baths

$1,650,000

4 beds4 baths2,475 sq ft

37 Village Center Rd Unit Blue Spruce 4, Ludlow, VT 05149

Property at 265 Depot St, Proctorsville, VT 05153, 3 beds, 2 baths

$895,000

3 beds2 baths3,291 sq ft

265 Depot St, Proctorsville, VT 05153

Property at 144 Lodge Rd Unit 1, Ludlow, VT 05149, 3 beds, 3 baths

$1,450,000

3 beds3 baths1,836 sq ft

144 Lodge Rd Unit 1, Ludlow, VT 05149

Property at 8 Okemo Acres Rd, Ludlow, VT 05194, 3 beds, 3.5 baths

$1,050,000

3 beds3.5 baths2,390 sq ft

8 Okemo Acres Rd, Ludlow, VT 05194

Property at 26 Mt Peg Rd Unit A, Woodstock, VT 05091, 3 beds, 3.5 baths

$975,000

3 beds3.5 baths2,592 sq ft

26 Mt Peg Rd Unit A, Woodstock, VT 05091

Property at 48 Alpine Way Unit D-1, Ludlow, VT 05149, 5 beds, 5.5 baths

$2,950,000

5 beds5.5 baths3,460 sq ft

48 Alpine Way Unit D-1, Ludlow, VT 05149

Property at 26 Mt Peg Rd Unit D, Woodstock, VT 05091, 3 beds, 3.5 baths

$975,000

3 beds3.5 baths2,385 sq ft

26 Mt Peg Rd Unit D, Woodstock, VT 05091

Property at 248 Gird Lot Rd, Springfield, VT 05156, 5 beds, 4.5 baths

$2,295,000

5 beds4.5 baths4,800 sq ft

248 Gird Lot Rd, Springfield, VT 05156

Property at 113 N Village Rd, Ludlow, VT 05149, 5 beds, 5.5 baths

$2,650,000

5 beds5.5 baths6,188 sq ft

113 N Village Rd, Ludlow, VT 05149

Property at 14/16 Summarsell Dr, Hartland, VT 05048

$1,576,000

— beds— baths9,455 sq ft

14/16 Summarsell Dr, Hartland, VT 05048

Property at 1 Depot St, Wilder, VT 05088

$999,500

— beds— baths3,218 sq ft

1 Depot St, Wilder, VT 05088

Property at 201 Spruce Dr, Andover, VT 05143, 3 beds, 2 baths

$879,999

3 beds2 baths3,310 sq ft

201 Spruce Dr, Andover, VT 05143

Property at 26 Mt Peg Rd Unit C, Woodstock, VT 05091, 3 beds, 3.5 baths

$875,000

3 beds3.5 baths2,584 sq ft

26 Mt Peg Rd Unit C, Woodstock, VT 05091

Property at 284 Elm Hl, Springfield, VT 05156

$1,800,000

Land161.80 acres (lot)

284 Elm Hl, Springfield, VT 05156

Property at 610 Route 100, Plymouth, VT 05056

$1,400,000

Land250.70 acres (lot)

610 Route 100, Plymouth, VT 05056

Property at 00 Markham Ln, Weston, VT 05161

$875,000

Land67.40 acres (lot)

00 Markham Ln, Weston, VT 05161

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Luxury Homes for Sale in Windsor County

There are currently 127 luxury homes for sale in Windsor County at a median listing price of $570K. 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 85 days. This map is refreshed with the newest listings in Windsor County every 15 minutes.

In the past month, 68 homes have been sold in Windsor County. In addition to houses in Windsor County, there were also 105 condos, 0 townhouses, and 17 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 Tue Oct 20 2026 on the search page

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