Windsor, VT Homes

/19
$125,000
- 3 Beds
- 1 Bath
- 700 Sq Ft
51 Depot St Unit 1, Proctorsville, VT 05153

This 3-bedroom, 1-bath condo offers easy living in a cozy, convenient setting. Enjoy first-floor living with an open kitchen, dining, and living area that’s perfect for gathering after a day of adventure. Hike scenic Hawks Mountain or access the VAST snowmobile trails just minutes from your door, and enjoy a short drive to area golf courses and the beautiful lakes region for boating, swimming,

Frank Provance Diamond Realty

51 Depot St Unit 1, Proctorsville, VT 05153
/29
$3,000 per month
- 3 Beds
- 2 Baths
- 2,256 Sq Ft
- House for Rent
79 Mountain View Ave, Proctorsville, VT 05153

79 Mountain View Ave, Proctorsville, VT 05153
/54
$402,060 Sold Aug 14, 2025
- 2,012 Sq Ft
- $200/SF
- 5 Days On Market
- 3 Beds
- 2 Baths
- Built 1992
317 Bailey Hill Rd, Cavendish, VT 05153

Vermont Charm Meets Modern Comfort - Secluded Cape Minutes to Okemo!Discover your perfect Vermont retreat on a private wooded one-acre in beautiful Cavendish.This enchanting 3-bedroom, 2-bathroom cape offers 2,000 square feet of thoughtfully designed living space that seamlessly blends classic New England charm with contemporary comfort. Nestled among mature trees on a full acre,

Rachael Rogala Rachael Rogala Inc.

317 Bailey Hill Rd, Cavendish, VT 05153

/13
Not Listed For Sale
00 Twenty Mile Stream Rd, Cavendish, VT 05142

00 Twenty Mile Stream Rd, Cavendish, VT 05142

/40
$430,000
- 2 Beds
- 2.5 Baths
- 1,445 Sq Ft
110 Spaulding Rd Unit G-3, Cavendish, VT 05153

If royalty is how you'd like to be treated then you've found your Castle. This two bedroom condominium is located at the Castle Hill Resort and Spa with unsurpassed amenities that any king and queen would appreciate. Just 3 miles to Okemo and all Ludlow has to offer and around the corner from charming, vibrant Proctorsville Green. This impeccable condo has been updated, well cared for and loved

Frank Provance Diamond Realty

110 Spaulding Rd Unit G-3, Cavendish, VT 05153
/11
$1,750 per month
- 1 Bed
- 1 Bath
- 600 Sq Ft
- House for Rent
214 Main St, Cavendish, VT 05153

NOT AVAILABLE UNTIL AUGUST 18, 2025. Fully furnished & outfitted, including kitchen pots/pans/plates/etc. Convection oven, microwave/hood fan over. Full sized fridge. Front loading W/D. Walkable to shopping, restaurant. 10 minutes to Okemo, 25 minutes to the Killington Skyeship. School right up the street, so no amount of snow will keep you from the Mountains! VAST trail right up the street too!

Robert Balewicz Evergreen Realty of Vermont

214 Main St, Cavendish, VT 05153
/37
$297,000 Sold Aug 08, 2025
- 1,120 Sq Ft
- $265/SF
- 6 Days On Market
- 2 Beds
- 1 Bath
- Built 1982
61 Davis Rd, Cavendish, VT 05153

Welcome to your perfect mountain retreat with a well kept mobile home on property that provides rental income! Nestled on 2.20 serene acres, this beautifully renovated home offers the ideal balance of modern comfort, natural beauty, and convenient access to year-round recreation. Whether you're an avid skier, outdoor enthusiast, or simply looking for a peaceful escape, this property offers

Evan Russell Real Broker LLC

61 Davis Rd, Cavendish, VT 05153

/40
Est $710,598 Not Listed For Sale
- 5 Beds
- 5 Baths
- 3,434 Sq Ft
621 Main St, Proctorsville, VT 05153

621 Main St, Proctorsville, VT 05153

/36
$895,000
- 3 Beds
- 5 Baths
- 3,590 Sq Ft
1104 Main St, Cavendish, VT 05142

Situated on the bank of the Black River at the edge of the Village Of Proctorsville is this three bedroom all ensuite, 5 bath log home. The Great Room boasts a floor to cathedral ceiling wood burning fireplace where you can sit and relax after a day on the slopes. Then take in river views from the formal dining room. Also on the first floor is a primary ensuite. Upstairs the huge lofted area is

Frank Provance Diamond Realty

1104 Main St, Cavendish, VT 05142
/36
$185,000 Sold Jun 27, 2025
- 1,782 Sq Ft
- $104/SF
- 2 Days On Market
- 3 Beds
- 2 Baths
- Built 1998
118 Depot St, Cavendish, VT 05153

Primary folks or skiers...stop renting! This is a large and efficient manufactured home that has a surprising floorplan. There is a large kitchen, dining room, living room, and a generous family room with fireplace. The primary bedroom has its own full bath, along with two guest bedrooms and a second full bath. Add to this a laundry room and two large, covered porches. The kitchen appliances

Betty McEnaney Diamond Realty

118 Depot St, Cavendish, VT 05153

/40
Not Listed For Sale
- 9 Beds
- 5 Baths
- 4,115 Sq Ft
260 Main St, Proctorsville, VT 05153

260 Main St, Proctorsville, VT 05153

/34
$299,000
- 3 Beds
- 2 Baths
- 1,232 Sq Ft
842 Main St, Proctorsville, VT 05153

Cared for by one owner for many years, this two-story 3 bedroom, 2 bath home on .26 +/- acres was built in 1977 and would make a very cute ski house or full-time home. Enter through the enclosed breezeway, a great space for entertaining and relaxing. The eat-in kitchen includes a breakfast/dining nook and excellent counter space. The living room is spacious and has plenty of natural light. A

Geralyn Donohue Engel & Völkers Okemo

842 Main St, Proctorsville, VT 05153
/36
$160,000 Sold Apr 15, 2025
- 675 Sq Ft
- $237/SF
- 23 Days On Market
- 1 Bed
- 1 Bath
- Built 2006
2940 Route 103 Unit 254, Cavendish, VT 05142

Convenience, comfort and location round out the Clarion Pointe Hotel. A well appointed one bedroom one bath condominium will streamline your visits to Vermont. The spacious unit has a living room with a gas fireplace for relaxing. Meals are a snap with the full kitchen and there's room for a small dining table. Lots of storage and plenty of counter space saves you money from dining out! Air

Joseph Karl William Raveis Real Estate Vermont Properties

2940 Route 103 Unit 254, Cavendish, VT 05142

/28
Est $820,317 Not Listed For Sale
- 5 Beds
- 3 Baths
- 4,044 Sq Ft
1101 Tattle St, Proctorsville, VT 05153

1101 Tattle St, Proctorsville, VT 05153

/43
$400,000
- 2 Beds
- 2.5 Baths
- 1,445 Sq Ft
60 Spaulding Rd Unit J1, Cavendish, VT 05153

Nestled on a quaint hillside in the Okemo Valley, the Castle Hill Resort offers an abundance of amenities with ownership in the resort community. This rare two-bedroom condominium provides ample space for everyone with extra windows for light and views. This is rare as most buildings are Quad-plexes and this building is a top and bottom Duplex, sharing no walls with neighbors! Enjoy an on-suite

Joseph Karl William Raveis Real Estate Vermont Properties

60 Spaulding Rd Unit J1, Cavendish, VT 05153
/58
$395,000 Sold Apr 11, 2025
- 2,424 Sq Ft
- $163/SF
- 114 Days On Market
- 6 Beds
- 3 Baths
- Built 1850
107 Depot St, Cavendish, VT 05153

Nestled along the Black River and the Green Mountain Railroad is this turn key fully furnished recently updated two family home. Located in the heart of the Village of Proctorsville and walking distance to local favorites such as Singletons Store, Murdoch's on the Green and soon to open Café. The Proctor Piper Forest is just around the corner for winter snowshoeing, x-country skiing and

Frank Provance Diamond Realty

107 Depot St, Cavendish, VT 05153

/38
Est $609,796 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,840 Sq Ft
1169 Twenty Mile Stream Rd, Proctorsville, VT 05153

1169 Twenty Mile Stream Rd, Proctorsville, VT 05153

/60
$1,500,000
- 10 Beds
- 12 Baths
- 5,500 Sq Ft
1589 Main St, Cavendish, VT 05142

Glimmerstone Mansion—an extraordinary legacy estate where timeless elegance meets modern sophistication. Set on 2.4± beautifully landscaped acres, this iconic property—listed on the National Historic Register—has been meticulously restored, thoughtfully upgraded, and exquisitely furnished. At the heart of the estate is the grand 10-bedroom mansion, where nearly every bedroom and gathering space

Kevin Barnes William Raveis Real Estate Vermont Properties

1589 Main St, Cavendish, VT 05142
/47
$282,500 Sold Feb 06, 2025
- 2,640 Sq Ft
- $107/SF
- 72 Days On Market
- 6 Beds
- 2 Baths
- Built 1810
550 Main St, Cavendish, VT 05142

Come enjoy the ease of Village living! With All of the conveniences of Proctorsville just a short walk away. This two family brick federal has been updated by it's current owner but there's still some finishing touches to be done although it is move in ready. Use one unit and have the tenants of the other pay the lions share of your expenses. Or have a great income producing rental the choice

Frank Provance Diamond Realty

550 Main St, Cavendish, VT 05142

/40
Est $338,652 Not Listed For Sale
- 5 Beds
- 2 Baths
- 1,650 Sq Ft
74 Greven Rd, Proctorsville, VT 05153

74 Greven Rd, Proctorsville, VT 05153

/60
$1,225,000
- 4 Beds
- 4.5 Baths
- 4,420 Sq Ft
2941 Twenty Mile Stream Rd, Cavendish, VT 05142

Experience timeless elegance and modern luxury in this exquisitely renovated 1834 farmhouse, gracefully sited on one of Cavendish’s most sought-after country roads. Thoughtfully updated while preserving its historic charm, this extraordinary residence features a state-of-the-art chef’s kitchen, whole house a/c and an expansive open-concept main level adorned with original hand-hewn beams and

Joseph Karl William Raveis Real Estate Vermont Properties

2941 Twenty Mile Stream Rd, Cavendish, VT 05142
/36
$350,000 Sold Jan 27, 2025
- 1,032 Sq Ft
- $339/SF
- 19 Days On Market
- 3 Beds
- 2 Baths
- Built 2005
316 Greven Road Extension, Proctorsville, VT 05153

Nestled in a wooded waterfront setting along the Black River, you will find this cozy log home. Custom designed and constructed by a builder for his family, the owner is now looking to replicate his creation on a more expansive scale to fit his needs as his family grows! So take advantage of this opportunity to have your own "piece" of Vermont.....less than 5 miles to world class skiing and golf

Diane Rousseau Four Seasons Sotheby's Int'l Realty

316 Greven Road Extension, Proctorsville, VT 05153

/32
Est $162,616 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,442 Sq Ft
1990 Main St, Cavendish, VT 05142

1990 Main St, Cavendish, VT 05142

/32
$299,000
- 6 Beds
- 2 Baths
- 2,518 Sq Ft
761 Main St, Cavendish, VT 05153

Location, Location, Location...Large families and investors take note. This classic colonial located on the corner of Main Street and Twenty Mile Stream Road is ready for the next family to enjoy or use for rental income. This was the family's gathering house for 55 years, and now it could be yours. There are 6 bedrooms, a woodstove/fireplace, mudroom, 1 car garage/workshop, and bonus space on

Kevin Barnes William Raveis Real Estate Vermont Properties

761 Main St, Cavendish, VT 05153
/42
$334,000 Sold Dec 11, 2024
- 1,562 Sq Ft
- $214/SF
- 54 Days On Market
- 3 Beds
- 2 Baths
- Built 1880
8 Wyman Rd, Cavendish, VT 05153

Antique home with renovations have kept the old-house character with exposed posts and beams while adding in conveniences of a stylish tiled shower, updated kitchen, insulation, sheetrock, and more.

Tyleen Murray Kelley Real Estate, Inc.

8 Wyman Rd, Cavendish, VT 05153

/38
Est $362,071 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,494 Sq Ft
665 Main St, Proctorsville, VT 05153

665 Main St, Proctorsville, VT 05153

/58
$635,000
- 3 Beds
- 3.5 Baths
- 2,203 Sq Ft
44 Freeman Rd Unit B2, Cavendish, VT 05153

The Castle Hill Resort & Spa is an award winning destination located just minutes from Okemo Mountain Resort. This ground floor 3br +loft & den features 3.5 baths. This townhouse condo has floor to ceiling windows that provide natural light throughout. The open living room, dining room, and kitchen offer an inviting atmosphere for gatherings. The ground floor patio offers outdoor seating and has

Joseph Karl William Raveis Real Estate Vermont Properties

44 Freeman Rd Unit B2, Cavendish, VT 05153
/32
$125,000 Sold Dec 06, 2024
- 715 Sq Ft
- $175/SF
- 69 Days On Market
- 2 Beds
- 1 Bath
- Built 1900
55 Depot St Unit 7, Cavendish, VT 05153

Looking for an easy keeper at a great price? This 2 bedroom. 1 bath condo is located just off the Proctorville Village Green where you will find free summer music concerts, a bus stop, a brew pub, EV charging station, and a restaurant. Singleton's Store is just a short walk away as are the town library and several other shops. The open floor plan for the first level has an updated kitchen, cozy

Kevin Barnes William Raveis Real Estate Vermont Properties

55 Depot St Unit 7, Cavendish, VT 05153

/39
Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,670 Sq Ft
2157 Twenty Mile Stream Rd, Cavendish, VT 05142

2157 Twenty Mile Stream Rd, Cavendish, VT 05142

/39
$195,000
- 1 Bed
- 1 Bath
- 675 Sq Ft
2940 Route 103 Unit 252, Cavendish, VT 05142

Welcome to effortless living at The Pointe at Castle Hill! This charming 1-bedroom, 1-bathroom condominium offers a convenient and low-maintenance lifestyle in a prime location. Just a stone's throw from Okemo Mountain Resort and Fox Run Golf Club, you'll be perfectly positioned to embrace Vermont's stunning outdoor recreation. Enjoy fantastic on-site amenities including a sparkling swimming

Matthew Bellantoni Mary W. Davis Realtor & Assoc., Inc.

2940 Route 103 Unit 252, Cavendish, VT 05142
/35
$435,000 Sold Oct 22, 2024
- 1,445 Sq Ft
- $301/SF
- 86 Days On Market
- 2 Beds
- 2.5 Baths
- Built 2005
41 Parkhurst Unit L1, Cavendish, VT 05153

Castle Hill L-1 is a well-maintained, two-bedroom condo with a cozy den featuring a wet bar. This immaculate home boasts beautiful wood flooring, granite countertops, and stainless steel appliances in the kitchen. Located in a lovely condominium community with quality finishes and an attractive design, Castle Hill is nestled in the mountains surrounding the historic Castle Inn, which is listed on

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

41 Parkhurst Unit L1, Cavendish, VT 05153

/40
Est $419,020 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,386 Sq Ft
1483 Main St, Cavendish, VT 05142

1483 Main St, Cavendish, VT 05142

/60
$550,000
- 3 Beds
- 3.5 Baths
- 2,203 Sq Ft
74 Spaulding Rd Unit I-4, Proctorsville, VT 05153

Welcome to the Castle Hill Resort and Spa community! This well-maintained 3 bedroom plus loft upper-level end unit has over 2200 square feet of space and is just a short drive to skiing and Okemo Mountain Resort amenities. The tiled mudroom entry leads to bright open spaces including the kitchen with breakfast bar, as well as the dining and living areas accented by a cathedral ceiling and

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

74 Spaulding Rd Unit I-4, Proctorsville, VT 05153
/40
$162,500 Sold Oct 11, 2024
- 784 Sq Ft
- $207/SF
- 229 Days On Market
- 2 Beds
- 1 Bath
- Built 2018
57 Depot St Unit 3, Cavendish, VT 05153

PRICE REDUCED! Completely refurbished! This tastefully decorated two bedroom one full bath condo is as turn key as it gets! Walk into the open living concept and enjoy the natural light from the wood sash windows. EVERYTHING is NEW! Flooring, paint, furnishings, TV, fixtures, boiler and electrical. Snuggle up in front of the new electric fireplace and watch some TV. Even the cook can watch

Frank Provance Diamond Realty

57 Depot St Unit 3, Cavendish, VT 05153

/40
Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,203 Sq Ft
28 Carriage Ln Unit E2, Cavendish, VT 05153

28 Carriage Ln Unit E2, Cavendish, VT 05153

/27
$295,000
- 1 Bed
- 1 Bath
- 675 Sq Ft
2940 Route 103 Unit 158, Cavendish, VT 05142

A Rare Find...1 bedroom condominium at Castle Point, only 3 miles to Okemo Mountain Resort.This condo can be rented out or used whenever you like, it is a full ownership property and fully furnished. It is located in the back away from the hotel lobbies, but has access to the pool and gym facilities. On the first floor the condo has an open living room with a gas fireplace, dining room, and a

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

2940 Route 103 Unit 158, Cavendish, VT 05142
/21
$249,000 Sold Oct 07, 2024
- 1,440 Sq Ft
- $173/SF
- 9 Days On Market
- Studio
- 2 Baths
- Built 1940
818 Main St, Cavendish, VT 05153

Welcome to this charming two-family home in Proctorsville! The downstairs unit, currently an Airbnb, features a mudroom, two bedrooms, a spacious living and dining area, a kitchen with an island, a full bathroom, and a laundry room. It comes fully furnished and turnkey, ready for the next owners! The upstairs unit, with a long-term tenant, offers two bedrooms, a living room, an eat-in kitchen, a

Mandolyn McIntyre Crow Real Broker LLC

818 Main St, Cavendish, VT 05153

/39
Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,023 Sq Ft
110 Spaulding Rd Unit G-2, Cavendish, VT 05153

110 Spaulding Rd Unit G-2, Cavendish, VT 05153

/33
$435,000
- 2 Beds
- 2.5 Baths
- 1,445 Sq Ft
28 Carriage Ln Unit E-3, Cavendish, VT 05153

Welcome to Castle Hill E-3, a charming and meticulously maintained two-bedroom plus den condo that perfectly balances comfort and style. This inviting end unit features a cozy den complete with a wet bar, ideal for relaxation and entertaining. Step inside to discover stunning wood flooring that enhances the warm atmosphere, complemented by elegant granite countertops, modern appliances, and a

Matthew Bellantoni Mary W. Davis Realtor & Assoc., Inc.

28 Carriage Ln Unit E-3, Cavendish, VT 05153
/2
$340,000 Sold Aug 23, 2024
- 1,312 Sq Ft
- $259/SF
- 0 Days On Market
- 3 Beds
- 2 Baths
- Built 2020
101 Mountain View Ave, Cavendish, VT 05153

Joseph Karl William Raveis Real Estate Vermont Properties

101 Mountain View Ave, Cavendish, VT 05153

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