Vintage homes for sale & real estate in Rutland County, VT

152 homes

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ABOUT THIS HOME
Vintage Home for sale in Rutland County, VT:
Move right in and enjoy the ease of single-level living in this recently renovated ranch, where a fresh, bright interior and an unexpectedly spacious yard come together in a home that is both comfortable and practical. Inside, the renovation creates a clean and cohesive feel throughout, with light-toned flooring, crisp white trim and an abundance of natural light. The living and dining areas flow easily together, providing flexible space for everyday living and entertaining. An additional room just off the kitchen offers even more versatility. This space ideal for a large heated mud room, a home office, sitting area or whatever best suits your needs. The kitchen is bright and functional, fe

$210,000

2 beds1 bath853 sq ft

270 Dorr Dr, Rutland, VT 05701

Spacious yard • Flexible space • Single-level living

ABOUT THIS HOME
Vintage Home for sale in Rutland County, VT:
Excellent location on Route 4, a major E-W state highway, "The Gateway to Killington", next to Aspen East with high traffic counts. Formerly original Aspen East Ski Shop & Surf the Earth Snowboards retail site, shipping, offices. This 2,971 square foot Building was renovated in 2022 by Luce Farm Wellness into a Showroom, Half Bath, Lab, Commercial Kitchen, Offices, Storage areas. LFW obtained Town and State Permits for CBD Manufacturing, Retail and Internet Sales. Lease expired 9/14/26. Situated in Commercial Route 4 zoning, it was originally a 3 bedroom home, and would make a nice home occupation or residence again. USES WHETHER OR NOT IN PUD: One, Two, MultiFamily Dwelling

$599,000

Studio0.5 baths2,971 sq ft

3471 Route 4, Killington, VT 05751

Convenient to town • Commercial kitchen • Renovated in 2022

ABOUT THIS HOME
Vintage Home for sale in Rutland County, VT:
Step back in time with this extraordinary 222 year old legacy estate - a treasure owned by the same family for more than two centuries. This remarkable property is a rare blend of grandeur and natural beauty along with historical significance. Once part of the Underground Railroad, the property has a fascinating past, and some of its former residents served as Civil War soldiers. The house was also used as the setting for the movie American Gun starring James Coburn with several scenes filmed inside the home. Imagine owning a home that is not only part of local history, but also part of cinematic history. Built in 1804, the magnificent 4/5 bedroom main home has been remarkably preserved - o

$775,000

5 beds2.5 baths5,882 sq ft

13 Route 22A, West Haven, VT 05743

Grand entrance • 222 year old estate • 79.13 acre lot

ABOUT THIS HOME
Vintage Home for sale in Rutland County, VT:
Check out this property. Some work needed but well worth the effort! This property started out as a 2 family and was converted to spacious 4 bedroom, 2.5 bath single family home. First floor has den or 5th bedroom, large 1/2 bath laundry room (easily a 3rd full bath, country kitchen waiting your your vision, living room and family room! Set on large level lot, featuring rear deck and two front porches and replacement windows. This could be your opportunity for "sweat equity". Cash or rehab only.

$99,900

4 beds2.5 baths1,632 sq ft

27 Meadow St, Proctor, VT 05765

0.26 acre lot • Built 1920 • Listed 50 days

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ABOUT THIS HOME
Vintage Home for sale in Rutland County, VT:
Red Clover Estate | A Legacy Vermont Retreat with Mountain Views, Historic Charm & Resort Proximity to Killington Ski Area, the largest four-season ski resort in the Northeast. The places that shape our lives are remembered not simply for their walls, but for the moments they quietly witness: generations gathered around a harvest table, celebrations that become traditions, and memories passed from one generation to the next. Red Clover Estate was created to be one of those extraordinary places. Nestled among Vermont’s rolling meadows and the Green Mountains, this rare legacy property blends historic New England character with luxurious rustic living. A landscaped drive leads to

$4,500,000

20 beds20.5 baths15,684 sq ft

54 Red Clover Ln, Mendon, VT 05701

Landscaped drive • Commercial kitchen • Historic charm

Property at 32 North St, Rutland, VT 05701, 4 beds, 1.5 baths

$445,000

4 beds1.5 baths3,499 sq ft

32 North St, Rutland, VT 05701

Property at 126 Crescent St, Rutland, VT 05701, 4 beds, 1.5 baths

$245,000

4 beds1.5 baths1,745 sq ft

126 Crescent St, Rutland, VT 05701

Property at 135 Harrington Ave, Rutland, VT 05701, 3 beds, 1 bath

$299,000

3 beds1 bath1,344 sq ft

135 Harrington Ave, Rutland, VT 05701

Property at 679 Rupert Hill Rd, Pawlet, VT 05761, 3 beds, 3 baths

$690,000

3 beds3 baths3,158 sq ft

679 Rupert Hill Rd, Pawlet, VT 05761

Property at 45 Park St, Rutland, VT 05701, 6 beds, 2 baths

$225,000

6 beds2 baths2,702 sq ft

45 Park St, Rutland, VT 05701

Property at 2248 Grove St, Brandon, VT 05733, 3 beds, 2 baths

$279,000

3 beds2 baths1,790 sq ft

2248 Grove St, Brandon, VT 05733

Property at 21 Royce St, Rutland, VT 05701, 5 beds, 3 baths

$309,000

5 beds3 baths3,374 sq ft

21 Royce St, Rutland, VT 05701

Property at 14 Jackson Ave, Rutland, VT 05701, 5 beds, 2 baths

$359,000

5 beds2 baths2,576 sq ft

14 Jackson Ave, Rutland, VT 05701

Property at 1174 N Main St, Danby, VT 05739, 4 beds, 3 baths

$595,000

4 beds3 baths3,272 sq ft

1174 N Main St, Danby, VT 05739

Property at 11 On The Green St, Poultney, VT 05764, 2 beds, 1.5 baths

$362,000

2 beds1.5 baths3,120 sq ft

11 On The Green St, Poultney, VT 05764

Property at 59 East St, Middletown Springs, VT 05757, 3 beds, 2 baths

$475,000

3 beds2 baths1,916 sq ft

59 East St, Middletown Springs, VT 05757

Property at 96 Prospect St, Wallingford, VT 05773, 3 beds, 1 bath

$285,000

3 beds1 bath1,456 sq ft

96 Prospect St, Wallingford, VT 05773

Property at 44 E Main St, Poultney, VT 05764, 4 beds, 2.5 baths

$60,000

4 beds2.5 baths2,688 sq ft

44 E Main St, Poultney, VT 05764

Property at 50 Pleasant St, Rutland, VT 05701, 6 beds, 4 baths

$689,000

6 beds4 baths4,792 sq ft

50 Pleasant St, Rutland, VT 05701

Property at 39 Williams St, Rutland, VT 05701, 3 beds, 1 bath

$249,000

3 beds1 bath925 sq ft

39 Williams St, Rutland, VT 05701

Property at 75 North St, Rutland, VT 05701, 4 beds, 3 baths

$260,000

4 beds3 baths2,336 sq ft

75 North St, Rutland, VT 05701

Property at 31-33 Gorham Bridge Rd, Proctor, VT 05765, 5 beds, 2.5 baths

$180,000

5 beds2.5 baths1,809 sq ft

31-33 Gorham Bridge Rd, Proctor, VT 05765

Property at 547 N Main St, Wallingford, VT 05773, 3 beds, 2 baths

$300,000

3 beds2 baths2,220 sq ft

547 N Main St, Wallingford, VT 05773

Property at 100 South St, Rutland, VT 05701, 6 beds, 4 baths

$399,000

6 beds4 baths2,776 sq ft

100 South St, Rutland, VT 05701

Property at 557 Pleasant Valley Rd, Benson, VT 05743, 4 beds, 3.5 baths

$600,000

4 beds3.5 baths1,727 sq ft

557 Pleasant Valley Rd, Benson, VT 05743

Property at 13 Kendall Ave, Rutland, VT 05701, 4 beds, 2 baths

$339,000

4 beds2 baths2,316 sq ft

13 Kendall Ave, Rutland, VT 05701

Property at 1871 Rte 103, Mount Holly, VT 05758, 2 beds, 2.5 baths

$475,000

2 beds2.5 baths2,734 sq ft

1871 Rte 103, Mount Holly, VT 05758

Property at 26 Park St, Brandon, VT 05733, 4 beds, 2 baths

$485,000

4 beds2 baths1,872 sq ft

26 Park St, Brandon, VT 05733

Property at 118 Park Ave, Rutland, VT 05701, 3 beds, 1.5 baths

$179,000

3 beds1.5 baths1,452 sq ft

118 Park Ave, Rutland, VT 05701

Property at 49 North St, Rutland, VT 05701, 5 beds, 2 baths

$345,000

5 beds2 baths2,457 sq ft

49 North St, Rutland, VT 05701

Property at 1376 Route 30, Sudbury, VT 05733, 3 beds, 1.5 baths

$550,000

3 beds1.5 baths2,459 sq ft

1376 Route 30, Sudbury, VT 05733

Property at 1310 Pleasant St, West Rutland, VT 05777, 2 beds, 1 bath

$285,000

2 beds1 bath1,200 sq ft

1310 Pleasant St, West Rutland, VT 05777

Property at 65 Church St, Rutland, VT 05701, 4 beds, 3 baths

$304,900

4 beds3 baths2,312 sq ft

65 Church St, Rutland, VT 05701

Property at 137 Maple St, Rutland, VT 05701, 4 beds, 2 baths

$165,000

4 beds2 baths1,704 sq ft

137 Maple St, Rutland, VT 05701

Property at 5187 VT Route 103, Shrewsbury, VT 05738, 3 beds, 2 baths

$395,000

3 beds2 baths2,226 sq ft

5187 VT Route 103, Shrewsbury, VT 05738

Property at 212 Thrall Rd, Poultney, VT 05701, 4 beds, 2.5 baths

$629,000

4 beds2.5 baths2,658 sq ft

212 Thrall Rd, Poultney, VT 05701

Property at 1560 Airport Rd, North Clarendon, VT 05759, 2 beds, 1 bath

$219,000

2 beds1 bath— sq ft

1560 Airport Rd, North Clarendon, VT 05759

Property at 41 Furnace St, Poultney, VT 05764, 5 beds, 2 baths

$330,000

5 beds2 baths2,080 sq ft

41 Furnace St, Poultney, VT 05764

Property at 208 Allen Ave, Poultney, VT 05764, 4 beds, 2.5 baths

$185,000

4 beds2.5 baths3,848 sq ft

208 Allen Ave, Poultney, VT 05764

Property at 150 Ryan Rd, Castleton, VT 05735, 3 beds, 1 bath

$579,000

3 beds1 bath1,118 sq ft

150 Ryan Rd, Castleton, VT 05735

Property at 172 Pinewoods Rd, Pittsford, VT 05763, 3 beds, 2 baths

$350,000

3 beds2 baths2,288 sq ft

172 Pinewoods Rd, Pittsford, VT 05763

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Vintage Homes for Sale in Rutland County

There are currently 152 vintage homes for sale in Rutland County at a median listing price of $399K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Rutland County stay on the market for 86 days. This map is refreshed with the newest listings in Rutland County every 15 minutes.

In the past month, 73 homes have been sold in Rutland County. In addition to houses in Rutland County, there were also 57 condos, 0 townhouses, and 46 multi-family units for sale in Rutland County last month. Find your dream home in Rutland 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 Rutland County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Rutland County. If you're looking to sell your home in the Rutland County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Rutland 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 Oct 10 2026 on the search page

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