Homes with Pools for Sale in Windsor County, VT

474 homes

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ABOUT THIS HOME
Home with a Pool for sale in Windsor County, VT:
An exquisite, private retreat for artists, writers, nature-lovers, composers or simply as a quiet, serene getaway gathering house on 66 stunningly beautiful acres with stone walls, gardens, patios, open lawns, a beautiful swimming pond, in-ground heated saltwater pool with stone patio, and a breathtakingly beautiful outdoor screened pergola. The residence was constructed using reclaimed frames from several historic hand-hewn cape homes built on a modern foundation with modern mechanicals. The home features antique period door hardware, hinges and locks throughout - and hand hewn beams and wall panel boards (some are 2 feet wide). Other features include 12-over-12 wavy glass windows, dutch d

$2,395,000

3 beds4 baths4,329 sq ft

719 Walker Hill Rd, South Royalton, VT 05031

Swimming pond • Open lawns • Patios

ABOUT THIS HOME
Home with a Pool for sale in Windsor County, VT:
Okemo Trailside 22-CL is a spacious one-bedroom with a bunk room, ideally located just a minute's walk from the Upper Sachem Trail. This ski-in/ski-out condo, which has seen significant renovations, offers flat, easy access to the slopes and community amenities. Inside, you'll find an open 884-square-foot layout. The entry features a mudroom with rustic pine accents, perfect for storing gear. The renovated kitchen with new appliances includes a breakfast bar that flows into a separate dining area, while the sunken living room centers around a cozy soon-to-be-installed Regency electric fireplace. The unit includes a primary bedroom with an en-suite bathroom, a separate bunk room, and an in-

$375,000

1 bed1 bath884 sq ft

162 Okemo Trailside Ext Unit 22C-L, Ludlow, VT 05149

In-unit laundry room • Sunken living room • Renovated kitchen

ABOUT THIS HOME
Home with a Pool for sale in Windsor County, VT:
COUNTRY LIVING ON 118 ACRES WITH FULLY APPLIANCED, 4 BR's, 1.5 BATH HOME WITH ATTACHED GARAGE WITH 2ND FLOOR, A STATE-OF-THE ART PELLET BOILER, ROOF TOP SOLAR SYSTEM, SMALL POND, BARN AND STORAGE BUILDINGS. THE LAND BOAST ONE OF THE MOST BEAUTIFUL AND PLENTIFUL SUGAR BUSH IN THE STATE THAT EASILY ACCOMADATES OVER 4500 TAPS. SEVERAL WELL-MAINTAINED WOOD-LAND TRAILS TRAVERSE THE ACREAGE AND THE MATURE STATELY MAPLES. SPECTACULAR MT. ASCUTNEY VIEWS WITH CLEARING. JUST 1 MILE WEST OF EXIT 8. 30 MINUTE DRIVE TO OKEMO OR MT. SUNAPEE.

$825,000

4 beds1.5 baths2,200 sq ft

1928 VT. Route 131, Springfield, VT 05156

Fully applianced • Barn • Small pond

ABOUT THIS HOME
Home with a Pool for sale in Windsor County, VT:
The Dewey House joins timeless elegance with contemporary convenience. Situated on a quiet road adjacent to the Quechee Gorge waterfall in the charming town of Quechee, this property offers easy access to I-89, I-91, and Route 4. Nearby walking trails and direct water access lend themselves to outdoor pursuits, while the views from the house and its decks over the mill pond and hills create the perfect place to visit with friends, relax to the soothing sounds of the waterfall, or watch for eagles and hot air balloons. Whether you intend to run this as a private home, a short-term rental, or a B & B, you'll love being on this gracious property. Enter through the front door to an expansiv

$1,400,000

6 beds5 baths4,571 sq ft

505 Deweys Mills Rd, Hartford, VT 05047

Expansive foyer • Views over the hills • Walking trails

VIDEO TOUR

ABOUT THIS HOME
Home with a Pool for sale in Windsor County, VT:
Jackson Gore on Okemo Mountain with this slopeside two-bedroom, two-bathroom corner condominium offering spectacular valley views. Thoughtfully designed for comfort and convenience, this residence features a open-concept living room with a gas fireplace, dining area, and a fully equipped kitchen—perfect for relaxing after a day on the mountain. The primary bedroom offers a king bed, while the second bedroom includes a queen bed, and a queen sleeper sofa in the living room provides additional accommodations. Located in the heart of Okemo’s Jackson Gore Village, this condo has ski-in/ski-out access all winter long. Enjoy underground heated parking, valet service, and gear lockers

$95,000

2 beds2 baths1,025 sq ft

238 Q1 Jackson Gore Inn Unit 238 Q1, Ludlow, VT 05149

Gas fireplace • Valley views • $377 HOA

Property at 6077 VT Route 12, Barnard, VT 05031, 4 beds, 3 baths

$795,000

4 beds3 baths2,099 sq ft

6077 VT Route 12, Barnard, VT 05031

Property at 9 Stryhas Trailer Ct, Ludlow, VT 05149, 3 beds, 2 baths

$179,000

3 beds2 baths1,120 sq ft

9 Stryhas Trailer Ct, Ludlow, VT 05149

Property at 75 Lyon Rd, South Royalton, VT 05068, 3 beds, 2 baths

$595,000

3 beds2 baths2,568 sq ft

75 Lyon Rd, South Royalton, VT 05068

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 1438 Gravelin Rd, Perkinsville, VT 05151, 2 beds, 1 bath

$169,500

2 beds1 bath1,500 sq ft

1438 Gravelin Rd, Perkinsville, VT 05151

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

$1,495,000

7 beds5 baths5,774 sq ft

310 Pierce Hill Rd, Brownsville, VT 05037

Property at 1522 Barnard Rd, Woodstock, VT 05091, 5 beds, 3.5 baths

$1,595,000

5 beds3.5 baths3,648 sq ft

1522 Barnard Rd, Woodstock, VT 05091

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

$1,195,000

3 beds3.5 baths2,385 sq ft

26 Mt Peg Rd Unit D, Woodstock, VT 05091

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 5677 Hendee Way #5677, Hartford, VT 05059, 4 beds, 4 baths

$1,525,500

4 beds4 baths2,752 sq ft

5677 Hendee Way #5677, Hartford, VT 05059

Property at 329 Main St, Proctorsville, VT 05153, 11 beds, 10.5 baths

$799,000

11 beds10.5 baths5,102 sq ft

329 Main St, Proctorsville, VT 05153

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 360 Okemo Trailside Ext Unit 37E, Ludlow, VT 05149, 4 beds, 2.5 baths

$1,495,000

4 beds2.5 baths1,938 sq ft

360 Okemo Trailside Ext Unit 37E, Ludlow, VT 05149

Property at 1279 Old Bridgewater Hill Rd, Bridgewater Corners, VT 05035, 4 beds, 4 baths

$3,300,000

4 beds4 baths5,000 sq ft

1279 Old Bridgewater Hill Rd, Bridgewater Corners, VT 05035

Property at 185 Riverbend Way, Woodstock, VT 05091, 3 beds, 2 baths

$72,999

3 beds2 baths1,008 sq ft

185 Riverbend Way, Woodstock, VT 05091

Property at 233 Brothers Rd, Hartland, VT 05048, 3 beds, 3.5 baths

$875,000

3 beds3.5 baths3,592 sq ft

233 Brothers Rd, Hartland, VT 05048

Property at 891 Route 100, Weston, VT 05161, 2 beds, 1 bath

$245,000

2 beds1 bath864 sq ft

891 Route 100, Weston, VT 05161

Property at 157 Dartt Hill Rd, Bethel, VT 05032, 5 beds, 3 baths

$949,000

5 beds3 baths2,807 sq ft

157 Dartt Hill Rd, Bethel, VT 05032

Property at 226 N Main St, Bethel, VT 05032, 3 beds, 1 bath

$249,000

3 beds1 bath1,140 sq ft

226 N Main St, Bethel, VT 05032

Property at 46 Partridge Rd, Ludlow, VT 05149, 5 beds, 4 baths

$2,499,000

5 beds4 baths5,305 sq ft

46 Partridge Rd, Ludlow, VT 05149

Property at 7868 Pomfret Rd, North Pomfret, VT 05053, 4 beds, 3 baths

$495,000

4 beds3 baths3,350 sq ft

7868 Pomfret Rd, North Pomfret, VT 05053

Property at 5518 VT Route 12, Barnard, VT 05031, 6 beds, 4.5 baths

$1,999,000

6 beds4.5 baths7,619 sq ft

5518 VT Route 12, Barnard, VT 05031

Property at 145 Russell Rd, Cavendish, VT 05142, 4 beds, 3 baths

$1,300,000

4 beds3 baths2,892 sq ft

145 Russell Rd, Cavendish, VT 05142

Property at 56 Grace Dr, North Springfield, VT 05150, 3 beds, 3 baths

$299,000

3 beds3 baths1,260 sq ft

56 Grace Dr, North Springfield, VT 05150

Property at 22 Birchwood Dr, Perkinsville, VT 05151, 3 beds, 2 baths

$435,000

3 beds2 baths1,440 sq ft

22 Birchwood Dr, Perkinsville, VT 05151

Property at 4071 Tichenor Rd #4071, Hartford, VT 05059, 5 beds, 4.5 baths

$1,675,000

5 beds4.5 baths3,837 sq ft

4071 Tichenor Rd #4071, Hartford, VT 05059

Property at 447 Elm St, Chester, VT 05143, 3 beds, 2 baths

$389,000

3 beds2 baths1,488 sq ft

447 Elm St, Chester, VT 05143

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 691 Dartt Hill Rd, Bethel, VT 05032, 2 beds, 1 bath

$649,000

2 beds1 bath1,196 sq ft

691 Dartt Hill Rd, Bethel, VT 05032

Property at 7873 Pomfret Rd, North Pomfret, VT 05053, 3 beds, 1.5 baths

$434,500

3 beds1.5 baths1,582 sq ft

7873 Pomfret Rd, North Pomfret, VT 05053

Property at 78 Division St, Hartford, VT 05088, 2 beds, 2 baths

$339,000

2 beds2 baths1,451 sq ft

78 Division St, Hartford, VT 05088

Property at 162 Bear Hill Rd, Plymouth, VT 05056, 3 beds, 2.5 baths

$649,000

3 beds2.5 baths1,788 sq ft

162 Bear Hill Rd, Plymouth, VT 05056

Property at 107 Blueberry Ledge Rdg Unit L-45, Plymouth, VT 05056, 3 beds, 2 baths

$429,000

3 beds2 baths1,428 sq ft

107 Blueberry Ledge Rdg Unit L-45, Plymouth, VT 05056

Property at 165 Moon Shadow Dr Unit M-15, Ludlow, VT 05149, 5 beds, 4.5 baths

$3,100,000

5 beds4.5 baths7,634 sq ft

165 Moon Shadow Dr Unit M-15, Ludlow, VT 05149

Property at 1057 Quarry Rd, Chester, VT 05143, 5 beds, 3.5 baths

$594,000

5 beds3.5 baths3,470 sq ft

1057 Quarry Rd, Chester, VT 05143

Property at 436 Mountain View Loop, Rochester, VT 05767, 3 beds, 1.5 baths

$299,000

3 beds1.5 baths1,248 sq ft

436 Mountain View Loop, Rochester, VT 05767

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Homes with Pools for Sale in Windsor County

There are currently 474 homes with pools for sale in Windsor County at a median listing price of $550K. 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 89 days. This map is refreshed with the newest listings in Windsor County every 15 minutes.

In the past month, 103 homes have been sold in Windsor County. In addition to houses in Windsor County, there were also 105 condos, 4 townhouses, and 26 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 2025 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 Mon Dec 01 2025 on the search page

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Homes with Pools for Sale in Windsor County, VT

Homes with Pools for Sale in Windsor County

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