Windsor County VT Homes under $400,000

/21
$375,000
- Land
- 10 Acres
- $37,955 per Acre
0 Turtle Hill Rd, Ludlow, VT 05149

Build Your Dream Home with Breathtaking Okemo Views! This exceptional nearly 10-acre parcel offers the perfect balance of privacy and convenience, just minutes from town. Enjoy some of the finest views of Okemo while designing your Vermont retreat. Nestled on a private road, this is the perfect spot for your four-season getaway—close to world-class skiing, the lakes region, top-rated restaurants,

Sarah Sheehan

William Raveis Real Estate Vermont Properties

(802) 348-2304

0 Turtle Hill Rd, Ludlow, VT 05149
/26
$367,000
- Land
- 11 Acres
- $34,754 per Acre
0 Valley View Dr, Ludlow, VT 05149

Elevate Your Lifestyle at Summit Ridge - Tucked away in a private, gated community just minutes from the slopes of Okemo and our Lakes Region, this homesite is the perfect canvas for your mountain dream home. Imagine waking up to panoramic, long-range mountain views in every direction—serenity, space, and stunning scenery, all wrapped into one unbeatable location with 10.56 acres. You're just a

Sarah Sheehan

William Raveis Real Estate Vermont Properties

(802) 424-8692

0 Valley View Dr, Ludlow, VT 05149
/47
$395,000
- 3 Beds
- 2 Baths
- 1,116 Sq Ft
32 Route 103 S Unit D4, Ludlow, VT 05149

Brookhaven condo D4 is located in the village of Ludlow and just a few minutes to the slopes at Okemo Mountain. This four-season destination is convenient to our lake’s region, restaurants, Fox Run Golf Club, shopping, and more. Enjoy easy access to the mountain with the Okemo Village Shuttle stopping in the Brookhaven parking lot. This top floor three-bedroom, two-full-bathroom condominium looks

Sarah Sheehan

William Raveis Real Estate Vermont Properties

(802) 705-0113

32 Route 103 S Unit D4, Ludlow, VT 05149
/23
$329,900
- Land
- 142 Acres
- $2,323 per Acre
0 Chateauguay Rd Unit 22557682, Woodstock, VT 05091

Interested in this property? Call, text, or email us today for more details!(540) 824-3372Feel free to visit the property any time, no need to set up an appointment, this property has no address.Subscribe to email alerts by texting your e-mail address to (541) 375-0012 and be the first to know when we get a great deal in.By texting (541) 375-0012 you authorize Country Land

Luke Harris Country Land Sellers

0 Chateauguay Rd Unit 22557682, Woodstock, VT 05091
/60
$375,000
- 4 Beds
- 2 Baths
- 2,425 Sq Ft
44 Watershed Rd, Bethel, VT 05032

TAMARACK FARM - Historic, very attractive 1.5 story brick cape with attached two-car garage, overlooking a deep ravine leading to a lower second acre on Route 12 perfect for equestrian pursuits. Nestled in a picturesque Vermont countryside, this classic 4-bedroom, 2-bath home showcases wide-board pine floors, exposed ceiling beams, and period details throughout. The first floor country kitchen

John Bassette Bassette Real Estate Group

44 Watershed Rd, Bethel, VT 05032
/22
$375,000
- 3 Beds
- 1 Bath
- 1,069 Sq Ft
879 Dairy Hill Rd, South Royalton, VT 05068

Located less than five minutes from the center of South Royalton, this well-cared-for ranch offers a peaceful setting with easy access off a paved, publicly maintained road to everything the Upper Valley has to offer. Vermont Law School is just down the road and S. Royalton is known for its tight-knit community, local food scene, and walkable village center — with Worthy Burger, a co-op, and a

Franchesca Collins Hall Collins Real Estate Group

879 Dairy Hill Rd, South Royalton, VT 05068
/46
$369,000
- 3 Beds
- 2 Baths
- 1,264 Sq Ft
43 Andover St, Ludlow, VT 05149

Embracing Life in a Charming Vermont Village Home.Village life is where time seems to slow down, watching the birds, listening to the brook from your deck while sipping your morning coffee or your evening glass of wine. A sanctuary that captures charm and character in every corner, this sweet and warm home invites you to live at a slower pace, allowing you to savor the small joys that often go

Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

43 Andover St, Ludlow, VT 05149
/54
$399,900
- 3 Beds
- 2 Baths
- 1,402 Sq Ft
387 Weston-Andover Rd, Chester, VT 05143

Nestled on a peaceful hillside in the town of Andover, this well-maintained home offers the soothing sounds of the Andover Branch River as your daily backdrop. Enjoy the ease of one-level living with three bedrooms, a full bathroom, and a comfortable main living space perfect for relaxing or entertaining.The walkout basement adds even more potential. Already underway is a second full bathroom and

Jessica Citera Cummings & Co

387 Weston-Andover Rd, Chester, VT 05143
/16
$379,000
- 2 Beds
- 2 Baths
- 960 Sq Ft
1474 Hartford Ave, White River Junction, VT 05001

This delightful ranch style home has two bedrooms and two baths. Hardwood Floors, laundry on the first level. Basement rooms are roughed in and offers a bonus room and plenty of storage. The attached one car garage allows for direct access to the home. Kitchen is spacious and has new flooring. Slider to a 14x14 deck. level back yard and a 8x8 storage shed. Room for flowers or garden. Close

Jill Stark RE/MAX Upper Valley

1474 Hartford Ave, White River Junction, VT 05001
/20
$370,000
- 3 Beds
- 2.5 Baths
- 1,726 Sq Ft
115 Austin Hill Rd, Rochester, VT 05767

This charming 3-bedroom, 2.5-bath contemporary home sits on 2 acres in a tranquil country setting, featuring a durable standing seam metal roof, wood siding, a carport, and an unfinished basement. The property boasts a private pond, and a few fruit trees looking for love. Enjoy direct access to nature and recreation, including proximity to ski and snowmobile trails. Inside, enjoy a sunroom with

Derek Greene Derek Greene

115 Austin Hill Rd, Rochester, VT 05767
/25
$370,000
- 2 Beds
- 1 Bath
- 1,208 Sq Ft
3078 N Hollow Rd, Rochester, VT 05767

Located in the sought after North Hollow section of Rochester is this 2 bdrm, 1 bath Ranch on 2 acres with attached garage and small outbuilding barn. Another larger barn/garage has the frame work erected with the rest of the materials on site for its next owner to complete. Charming country setting with great curb appeal including stone walls and set off the roadway surrounded by panoramic

Patricia Harvey Xsell Realty LLC

3078 N Hollow Rd, Rochester, VT 05767
/19
$379,000
- 3 Beds
- 2 Baths
- 1,496 Sq Ft
0 Pleasant St, Cavendish, VT 05142

This home has served as a primary residence and also as an income-producing rental and can be sold furnished. While the upper level of this home has three bedrooms, the walk-out lower level of the home has such potential as well.It is currently partially finished and is being used as a family room and for storage. The large deck on the end of the house is perfect for taking in some fresh Vermont

Tyleen Murray Kelley Real Estate, Inc.

0 Pleasant St, Cavendish, VT 05142
/23
$359,000
- 4 Beds
- 2 Baths
- 1,248 Sq Ft
26 Dorman Rd, Andover, VT 05143

Prepare for an exhilarating mountain getaway at this enchanting four-bedroom chalet, nestled on a lush 2.1-acre estate in the heart of Andover. 2025 Ski season has been epic so far! Envision yourself minutes away from four renowned ski resorts, making this the perfect launchpad for your winter adventures. Immerse yourself in the local charm with easy access to the VAST trail network, offering a

Daire Gibney Barrett and Valley Associates Inc.

26 Dorman Rd, Andover, VT 05143
/56
$365,000
- 3 Beds
- 2 Baths
- 1,880 Sq Ft
25 Laplante Rd, Cavendish, VT 05142

Welcome to 25 Laplant Road in Cavendish, VT—a private retreat offering the perfect balance of comfort and adventure. Built in 2009 and thoughtfully updated, this inviting home features a spacious and welcoming design, perfect for effortless entertaining. The main level boasts a bright living area, a well-appointed kitchen with a propane range, new dishwasher, and a cozy pellet stove—ideal for

Zack Bourque BHHS Verani Upper Valley

25 Laplante Rd, Cavendish, VT 05142
/28
$370,000
- 4 Beds
- 2 Baths
- 1,850 Sq Ft
201 Latham Works Ln, White River Junction, VT 05001

This charming New Englander-style home features TWO separate units! Each unit includes 2-bedrooms and 1-bathroom, as well as its own spacious eat-in kitchen, family/living room, private entrance, and laundry room. The partially finished basement provides ample clean space for extra storage as well. Outside you'll find an enclosed porch to the side and a stone patio out back overlooking a large

Alex Shaffer Four Corner Properties LLC

201 Latham Works Ln, White River Junction, VT 05001
/32
$329,000
- 3 Beds
- 1.5 Baths
- 1,732 Sq Ft
359 S Mountain Rd, Perkinsville, VT 05151

A home with heart and bold personality: new heating system, windows, doors, and a stunning mahogany entry.The kitchen blends new appliances with vibrant, thoughtful design.A brand-new deck off the primary bedroom overlooks the peaceful flow of Mill Brook — a perfect spot for morning coffee or evening unwinding.Enjoy gardens, a fire pit, and direct walk-on access to the scenic Summit Trail — it’s

Daniel Preston KW Vermont Woodstock

359 S Mountain Rd, Perkinsville, VT 05151
/45
$350,000
- 4 Beds
- 2 Baths
- 2,484 Sq Ft
47 Dell Rd, Springfield, VT 05156

Welcome to a home that truly has it all! Perfectly positioned on a cul-de-sac, this property is steps away from the trailhead of Hartness Park where you can enjoy 3 miles of trails in the 85 acre town forest. A seamless blend of privacy whilst still being in town - what more can you ask for? This beautifully maintained property offers the rare and coveted convenience of first-floor living—with

Taylor Medeiros-Batey KW Coastal and Lakes & Mountains Realty/Hanover

47 Dell Rd, Springfield, VT 05156
/10
$385,000
- 6 Beds
- 4 Baths
- 2,949 Sq Ft
7 Commonwealth Ave, Ludlow, VT 05149

Bring your vision and unlock the potential! This property has been fully gutted and is ready for your transformation. With a new roof, windows and siding and decking on the porch, you're well on your way! Conveniently located in the Village Of Ludlow near skiing, golf, lakes for swimming, and village shopping, it’s the perfect opportunity for contractors, investors, or DIYers. With two separate

Frank Provance Diamond Realty

7 Commonwealth Ave, Ludlow, VT 05149
/35
$319,950
- 2 Beds
- 1.5 Baths
- 1,120 Sq Ft
141 Dawn Dr, White River Junction, VT 05001

Tucked into a quiet, tree-lined community just minutes from Dartmouth and Quechee, this move-in-ready townhome offers comfort, style, and convenience in equal measure. Step inside to an airy open-concept layout with hardwood floors and abundant natural light. The updated kitchen stands out with granite countertops, stainless steel appliances, subway tile backsplash, and a mobile butcher block

Nick Sicard EXP Realty

141 Dawn Dr, White River Junction, VT 05001
/49
$350,000
- 3 Beds
- 3 Baths
- 1,932 Sq Ft
5 Church St, North Springfield, VT 05150

Nicely maintained 3BR/3BA ranch home just waiting for a new family. This home features large, updated eat-in kitchen with sliders to a deck, main floor laundry, gas fireplace, home office/den, partially finished basement has a 3/4 bath, workshop area, partially finished rooms that could be additional bedrooms and a large partially finished area for family room. Primary bedroom with bath and

Julie Buffum Buffum Realty

5 Church St, North Springfield, VT 05150
/34
$375,000
- 3 Beds
- 2 Baths
- 1,352 Sq Ft
847 Simonsville Rd, Andover, VT 05143

Come find your own peaceful piece of the Vermont countryside in the beautiful town of Andover. Look no further than this move in ready homestead on 51.2 rolling acres with two large paddocks fenced and ready waiting for your animals, complete with two spacious sheds, and a chicken coop ready to house them. Established asparagus patch, blueberry bushes, apple trees, and even your own cranberry bog

Erin Kendall EXP Realty

847 Simonsville Rd, Andover, VT 05143
/3
$329,900
- Land
- 142 Acres
- $2,323 per Acre
00 Chateauguay Rd, Bridgewater, VT 05034

Prime land access off Chateauguay Rd with no zoning, HOA, or deed restrictions. Sub-dividable with well and septic needed; electricity nearby. Just 25 minutes from the town of Woodstock’s amenities, parks and historic sites. 20 minutes to Killington Ski Resort and Coolidge State Park, and 30 minutes to Pico Mountain Ski Resort and Lynches River County Park. Perfect for building your dream home or

Derek Greene Derek Greene

00 Chateauguay Rd, Bridgewater, VT 05034
/38
$399,000
- 3 Beds
- 2 Baths
- 2,224 Sq Ft
165 N Main St, Rochester, VT 05767

Nestled in the heart of Rochester, a small and vibrant town, this early Post and Beam home offers the perfect blend of historic character and contemporary upgrades. Wide pine floors, exposed beams, and a cozy fireplace in the main-level primary bedroom highlight the home's rustic charm. With two bathrooms, two living rooms, and an open layout, there’s plenty of space to relax and entertain.

Gail Engel & Völkers Okemo

165 N Main St, Rochester, VT 05767
/31
$324,000
- 2 Beds
- 1.5 Baths
- 1,824 Sq Ft
1221 Baker Turn Cir Unit 1D, Hartford, VT 05059

This very spacious 2BR, 1.5BA townhouse has been tastefully renovated from top to bottom with all new laminate hardwood floors, appliances, doors and paint throughout. It is being offered fully furnished providing for a truly turn key buying opportunity. It is located within less than 100 yards to the top of the Quechee Ski Hill.

Herb Hart Quechee Lakes Real Estate Center

1221 Baker Turn Cir Unit 1D, Hartford, VT 05059
/45
$340,000
- 3 Beds
- 2.5 Baths
- 2,072 Sq Ft
37 Wright Rd, Ludlow, VT 05149

This residence offers great opportunities for the next owner and is located in an ideal location within close proximity to the village of Ludlow, Okemo Mountain and the many amenities the Okemo Valley provides, all only minutes away. The spacious layout, with 3 bedrooms and 2.5 bathrooms, has good bones and is primed to be modernized, it simply awaits your vision. Once you arrive, you will find

Roger Danyew Diamond Realty

37 Wright Rd, Ludlow, VT 05149
/48
$395,000
- 3 Beds
- 1 Bath
- 1,064 Sq Ft
125 W Hill Rd, Ludlow, VT 05149

125 West Hill Road, per google maps it's 2 minutes to the Okemo base .07 miles away. AND just a one minute walk to the West Hill Recreation Area. This throwback ranch home has been well cared for and loved by the original family who built the house. Pull into the two car garage and unload your gear into the breezeway that could be the ultimate mudroom/playroom. Step into the eat in kitchen

Frank Provance Diamond Realty

125 W Hill Rd, Ludlow, VT 05149
/12
$399,000
- Land
- 4.73 Acres
- $84,355 per Acre
5209 5211 Willard Rd, Hartford, VT 05059

We are pleased to offer a rare and highly desirable estate-sized double lot in the Upper Willard Road neighborhood of Quechee Lakes. The two parcels that make up this 4.73+/- acres of Vermont countryside were strategically assembled by the current owner to offer an excellent opportunity to build your Vermont retreat in the region’s favorite four-season recreational lifestyle resort. With

Richard Higgerson Higgerson & Company

5209 5211 Willard Rd, Hartford, VT 05059
/2
$349,000
- Land
- 10 Acres
- $35,253 per Acre
00 Main St, Ludlow, VT 05149

LOCATION LOCATION LOCATION....options are unlimited for this large ready to develop parcel. Okemo Mountain views, level (and mostly cleared) parcel with MAJOR ROAD FRONTAGE! You can't beat the spot or the wonderful mountain view!** One of the owners is a licensed Vermont Real Estate agent.

Lisa Kelley Cummings & Co

00 Main St, Ludlow, VT 05149
/19
$385,000
- 1 Bed
- 1 Bath
- 599 Sq Ft
350 Mountain Rd Unit B301, Ludlow, VT 05149

This beautifully remodeled, top-floor end-unit condominium is the perfect slopeside retreat. Recent updates include new granite countertops, stainless steel appliances, custom cabinetry, new flooring throughout, an updated bathroom, and stylish furnishings. Even the doors have been upgraded to solid wood for a high-end touch. Turn the key and start enjoying—there's nothing left to do except hang

Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

350 Mountain Rd Unit B301, Ludlow, VT 05149
/31
$325,000
- 2 Beds
- 1.5 Baths
- 1,546 Sq Ft
22 Andover St, Ludlow, VT 05149

Cozy village home on town water/sewer within walking distance to the shuttle to Okemo, shops, restaurants and all that the village of Ludlow has to offer! This 2 bedroom, (seller is applying for a 3 br permit), with a bonus room is a 2 level farmhouse style charmer. The main level has an eat-in kitchen with a pantry, dining room, living room and a bonus room that leads to an attached barn. There

Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

22 Andover St, Ludlow, VT 05149
/26
$350,000
- 1 Bed
- 1 Bath
- 638 Sq Ft
350 Mountain Rd Unit B305, Ludlow, VT 05149

Direct slopeside oversized Okemo Mountain Lodge unit comfortably sleeps 6. Top floor location offers wide panoramic views of the slopes and neighboring hillsides, and fills the unit with natural light. Open living design includes kitchen with breakfast bar, living room with fireplace, and large bedroom with private access to full bath. Deck off living room offers wonderful outdoor space

Andre Menard Mary W. Davis Realtor & Assoc., Inc.

350 Mountain Rd Unit B305, Ludlow, VT 05149
/32
$385,000
- 1 Bed
- 1 Bath
- 640 Sq Ft
109 Okemo Ridge Rd Unit C201, Ludlow, VT 05149

Located Direct Slopeside, this 1 bedroom, 1 full bath end unit condominium at Okemo Mountain Lodge is available for the first time in 20 years! Beautifully renovated throughout and nicely furnished, C201 is ready for your family to move right in. The larger style kitchen has plenty of cabinetry and counter space, is light and bright, and open to the living room which features an electric

Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

109 Okemo Ridge Rd Unit C201, Ludlow, VT 05149
/23
$325,000
- Land
- 45 Acres
- $7,222 per Acre
1376 Kingdom Rd, Plymouth, VT 05056

Rare offering of forty-five beautiful acres in the lakes region between Killington and Okemo. You know what they say..."They don't make more land". More photos coming soon or come and take a look yourself and hike or snowshoe around the property. Potential views of Okemo with clearing. Subdivision is possible and has been started at the State level (along with wastewater permitting), but needs to

Tyleen Murray Kelley Real Estate, Inc.

1376 Kingdom Rd, Plymouth, VT 05056
/39
$325,000
- 4 Beds
- 1 Bath
- 1,554 Sq Ft
2 Pond St, Ludlow, VT 05149

This charming home, cherished by one family since the mid-1950s, presents a wonderful opportunity for renovation and personalization. This nine room home has 4 bedrooms, 1 bath, and an eat-in kitchen. The location is ideally situated within walking distance of Dorsey Park and Ludlow Village. Catch the shuttle bus to Okemo for a day of skiing or walk to the restaurants, grocery store and all the

Michael Normyle Mary W. Davis Realtor & Assoc., Inc.

2 Pond St, Ludlow, VT 05149
/60
$399,000
- 3 Beds
- 3.5 Baths
- 1,664 Sq Ft
2680 Hartford Ave Unit 28, White River Junction, VT 05001

Special unit at Stony Creek. This home is sited for privacy and it's location within the community ranks at the top. Original owner designed the lower level bedroom/office to have an additional bathroom. Open main level features a thoughtful kitchen with stainless appliances open to the livingroom with hardwood floors throughout. Deck off the livingroom. Two spacious bedrooms on the upper level

Dorothy Griswold The Clerkin Agency, P.C.

2680 Hartford Ave Unit 28, White River Junction, VT 05001
/13
$395,000
- 2 Beds
- 1 Bath
- 640 Sq Ft
109 Okemo Ridge Rd Unit C301, Ludlow, VT 05149

Okemo Mountain Lodge 2 BR FOR SALE! This charming condo with amazing mountain views is located at 109 Okemo Ridge Rd, C Bldg, 3rd floor, Unit 301 at Okemo, VT. It was built in 1984 and is one of only two units with an extra room which is currently furnished as a 2nd bedroom. CHECK OUT THE PICTURES! Highlighted features include a breakfast bar, ski locker, and outside deck with a great view up the

Derek Greene Derek Greene

109 Okemo Ridge Rd Unit C301, Ludlow, VT 05149
/6
$349,900
- Land
- 1.80 Acres
- $194,389 per Acre
115 Rimrock Rd, Ludlow, VT 05149

Amazing opportunity to own a trailside 1.8-acre lot in the prestigious Okemo Resort! Imagine the ultimate ski-in/ski-out lifestyle, with direct access to the Sachem Trail right from your doorstep. Build your dream mountain retreat and wake up to breathtaking views and endless outdoor adventures. This piece of paradise is ready to make your vision a reality. Don't miss your chance to own one of

Jacek / Realtor Mikolajczyk BHHS Verani Upper Valley

115 Rimrock Rd, Ludlow, VT 05149
/37
$389,000
- 3 Beds
- 2 Baths
- 2,113 Sq Ft
123 Commonwealth Ave, Springfield, VT 05156

This Totally Renovated 3 BR 2 Bath Cape On a Quiet Dead End Street Has Everything You Want. Newly Modernized Kitchen with Granite Counters and Tons of Cabinets, Awesome Dining Room With Lots of Windows and Spacious Living Room with Electric Fireplace and Beautiful Hardwood Floors Throughout Most of the Home. Plus Both Gorgeous Bathrooms were Just Redone. Spacious Lower Level Family Room with

Brian Whipple Coldwell Banker Homes Unlimited

123 Commonwealth Ave, Springfield, VT 05156
/18
$398,000
- Land
- 14 Acres
- $29,265 per Acre
87 Aldrich Farm Rd, Sharon, VT 05065

This stunning 13.6-acre property on Aldrich Farm Road boasts long-range westerly views of the Green Mountains, including Killington and Pico peaks. The land features a gently sloping open meadow (approximately 5 acres), a mixed hardwood forest, and a babbling brook that flows into a small pond. A carefully reconstructed historic stone wall at the southwestern edge enhances the classic New England

David White OwnerEntry.com

87 Aldrich Farm Rd, Sharon, VT 05065
/7
$324,000
- 4,077 Sq Ft
96 Chester Rd, Springfield, VT 05156

ATTENTION INVESTORS 5 UNITS PLUS 3 GARAGE SPACES. 3- 2 BR's, 1- 3 BR's UNIT and 1- 1BR's UNIT. ACTUAL CAP RATE 11.55%, PROFORMA CAP 14.29%. SHOWING APPOINTMENTS REQUIRE 48 HOUR NOTICE TO TENANTS. PRICE IS NEGOTIABLE FOR CASH OFFERS AND QUICK CLOSING!

Don Chabot Town and Country Realty

96 Chester Rd, Springfield, VT 05156

Showing Results 1 - 40, Page 1 of 2

Vermont Windsor County

How to Buy a Home How to Finance a Home How to Sell a Home

Homes in Nearby Cities

Homes in Nearby Counties

Homes in Nearby Zip Codes

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Copyright 2025 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, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.