5-Bedroom Homes for Sale in Rutland County VT

/24
$279,000
- 5 Beds
- 5 Baths
- 480 Sq Ft
52 Altrui Place, Rutland, VT 05701

Live in One, Rent the Others – Multi-Unit Investment Opportunity!Tucked away on a dead-end street and just minutes from local schools and shops, this unique property features three separate homes on one lot—ideal for investors or those looking to live in one unit and generate income from the others.The property includes two single-wide mobile homes and a newly renovated, move-in ready

Hughes Group Team

Casella Real Estate

(802) 471-2447

52 Altrui Place, Rutland, VT 05701
/27
$285,000
- 8 Beds
- 5 Baths
- 3,220 Sq Ft
9 River St, Fair Haven, VT 05743

Here is an investment opportunity with this well-maintained multi-family property, featuring five rental units and a solid cap rate of 10%. This property includes three two-bedroom apartments, a comfortable one-bedroom unit, and a cozy efficiency, offering a balanced mix of layouts to attract a wide variety of tenants. All apartments benefit from included amenities that simplify the rental

Hughes Group Team

Casella Real Estate

(802) 242-8915

9 River St, Fair Haven, VT 05743
/16
$386,000
- 6 Beds
- 2 Baths
- 2,392 Sq Ft
782 North St, Wells, VT 05774

LAKE ST CATHERINE. A family tresure for years to come! A great way to get on the lake at a great price! Nothing compares to your family enjoying lake activities. Whether it is swimming, boating, fishing, barbecuing or roasting S'mores over a campfire, creating lake memories will last a lifetime. Fit your whole gang into this spacious 6 bedroom, 2 full bath open floor plan, spanning approximately

Lori Andrus-Winn

New England Lakeside Realty

(802) 808-6324

782 North St, Wells, VT 05774
/31
$345,000
- 5 Beds
- 1 Bath
- 1,687 Sq Ft
416 Upper Rd, Poultney, VT 05764

Back on Market due to buyer's inability to meet financing contingency. Take advantage of this opportunity to own this quintessential Vermont Farmhouse situated on 8+ acres with barn, outbuildings and oversized two car garage plus workshop with lower and upper-level storage. This property offers the opportunity for animals and crops with some tillable acres. The five bedrooms provide ample room

Suanne Ohl

Northland Real Estate

(802) 454-3247

416 Upper Rd, Poultney, VT 05764
/38
$499,000
- 12 Beds
- 6 Baths
- 6,390 Sq Ft
49 Terrill St, Rutland, VT 05701

Don’t miss this prime investment opportunity! This well-maintained 5-unit multifamily property offers an impressive 9.8% cap rate and features a desirable unit mix of three 2-bedroom apartments and two spacious 3-bedroom apartments, ensuring strong rental demand. Situated in a convenient location within walking distance to downtown shops and restaurants, the property appeals to both long-term

Hughes Group Team

Casella Real Estate

(802) 300-3794

49 Terrill St, Rutland, VT 05701
/45
$1,200,000
- 10 Beds
- 4.5 Baths
- 6,800 Sq Ft
3356 Route 22a, Fair Haven, VT 05743

Gone With the Wind vibes in this historic colonial farmhouse built in 1790 and registered on the National Historic Registry. This estate is comprised of several buildings on 83 scenic acres and has breathtaking sunrise mountain views. Main house, carriage house with 4 car garage, a duplex home, 11 stall stable, 2 other barns - one with indoor riding area, 2 car garage plus fenced pastures and

Lisa Friedman

Great American Dream Realty

(802) 551-3041

3356 Route 22a, Fair Haven, VT 05743
/60
$1,997,000
- 5 Beds
- 4.5 Baths
- 3,343 Sq Ft
330 Rupert Hill Rd, Pawlet, VT 05761

Amazing Agricultural Package: 54 Bucolic Acres, 360 degree hill-top views, 1407 feet Mettowee River frontage, Complete 2023 Renovation of 5343 SF contemporary farm house, Barns and Run-in sheds, Guest house, Walk to Pawlet Village convenience! That's just the tip of the iceberg... the winding drive overlooks open pastures and rolling terrain through hardwood forests as it approaches the hill top

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 327-7303

330 Rupert Hill Rd, Pawlet, VT 05761
/34
$438,000
- 5 Beds
- 4 Baths
- 2,501 Sq Ft
328 Main St, Poultney, VT 05764

This elegant Greek Revival home sits at the edge of Poultney, Vermont's Historic Main Street. Known as The Two Editors Inn, it honors two of Poultney's notable citizens, Horace Greeley and George Jones, who honed their printing skills locally before founding The New York Tribune and The New York Times. This home showcases the elegance and romance of the American renaissance; from its prominent

Suanne Ohl

Northland Real Estate

(802) 520-0922

328 Main St, Poultney, VT 05764
/19
$315,000
- 8 Beds
- 4 Baths
- 3,535 Sq Ft
230 Marble St, West Rutland, VT 05777

Unlock your next investment property! This multifamily provides the perfect blend of charm, convenience, and outdoor adventure right here in the heart of West Rutland. What once was a mix use of downtown shops and apartments, has since been converted into 4 unique, spacious apartments which are all currently occupied and generating good income. Located in town, residents have easy access to local

Hughes Group Team

Casella Real Estate

(802) 471-3241

230 Marble St, West Rutland, VT 05777
/39
$499,000
- 5 Beds
- 1.5 Baths
- 2,500 Sq Ft
68 Church St, Poultney, VT 05764

Do not miss this beautiful five bedroom Federal home with upgrades and renovations throughout. Once a church rectory the pocket doors, beautiful hardwood floors and natural woodwork are maintained throughout. Replacement windows and upgraded mechanicals are just a few features inside this glorious home. The partially finished attic space is ready for the new owner's creativity. The back deck

Nancy Liberatore

Lakes & Homes Real Estate

(802) 317-8140

68 Church St, Poultney, VT 05764
/36
$599,000
- 5 Beds
- 3 Baths
- 3,876 Sq Ft
5 Pearl St, Brandon, VT 05733

When you picture a classic village home in Vermont, what comes to mind? A beautiful fascade, large flat yard, inviting entrance? All of the above?! Plus so much more. Brandon is a unique VT town with tree lined streets, elbow room between neighbors, a lovely downtown village center with green space, markets, restaurants, bakeries, breweries and shops. Within this quintessential village sits 5

Amey Ryan IPJ Real Estate

5 Pearl St, Brandon, VT 05733
/36
$1,375,000
- 6 Beds
- 3 Baths
- 3,584 Sq Ft
96 Tabor Rd, Cuttingsville, VT 05738

The ultimate Vermont retreat - private setting with 93.4 acres across 3 subdivided lots, featuring miles of trails, 3 ponds (one with beach area within view of house, another stocked pond with zipline), fruit trees, gardens, and open fields for year-round recreation. This 6BR, 3BA home includes a stunning two-story recent addition with 3 upstairs bedrooms and a light-filled main-level bonus room

Kim Prins Four Seasons Sotheby's Int'l Realty

96 Tabor Rd, Cuttingsville, VT 05738
/25
$1,200,000
- 7 Beds
- 3.5 Baths
- 4,442 Sq Ft
99 Spooner Point, Castleton, VT 05735

LAKE BOMOSEEN SPECIAL OFFERING. Built in 1874, this stately three-story home is a proud remnant of Lake Bomoseen’s storied past, once a distinguished estate overlooking Vermont’s largest freshwater lake, it remains a testament to 19th-century craftsmanship and lakeside elegance. Treasured by generations for over several centuries, this beloved home has been the backdrop to countless memories and

Freddie Ann Bohlig Four Seasons Sotheby's Int'l Realty

99 Spooner Point, Castleton, VT 05735
/60
$1,499,000
- 5 Beds
- 4 Baths
- 5,006 Sq Ft
2427 Monument Hill Rd, Castleton, VT 05735

Discover your Vermont sanctuary just 2 miles from stunning Lake Bomoseen and a short drive to the scenic Half Moon State Park! This exceptional home offers a perfect blend of natural beauty and luxurious comfort nestled within over 80 acres of lush land. Imagine waking up to breathtaking water features - a deep spring-fed pond, a majestic fifty-foot waterfall, and a tranquil year-round brook

Michael Johnston Coldwell Banker Hickok and Boardman

2427 Monument Hill Rd, Castleton, VT 05735
/60
$1,395,000
- 5 Beds
- 2.5 Baths
- 3,696 Sq Ft
152 Wobbly Ln, Killington, VT 05751

Situated in the heart of one of Killington’s most prestigious neighborhoods, this exceptional mountain retreat blends timeless charm with modern luxury. Just steps from the area’s premier amenities—including world-renowned skiing, snowmobiling, mountain biking, golf, fine dining, and tranquil lakes—this property offers the ultimate Vermont lifestyle. The main residence showcases a beautifully

Will Spanos KW Vermont-Killington

152 Wobbly Ln, Killington, VT 05751
/45
$975,000
- 5 Beds
- 4.5 Baths
- 4,125 Sq Ft
1955 Saw Mill Hill Rd, Wells, VT 05774

This idyllic gathering place set on 10+ acres showcases breathtaking mountain panoramas with numerous living possibilities. The meticulously maintained two-bedroom main house is a charming reproduction eyebrow cape with impressive architectural details. The thoughtfully designed home features living spaces that are defined by warm wood beams and an over-sized Rumford fireplace. The well-appointed

Katherine Zilkha Four Seasons Sotheby's Int'l Realty

1955 Saw Mill Hill Rd, Wells, VT 05774
/60
$1,650,000
- 7 Beds
- 5.5 Baths
- 6,415 Sq Ft
444 Tin Shanty Rd, Cuttingsville, VT 05738

Discover the beauty of this private country retreat on 124 acres. This 7-bedroom, 6-bath estate offers total seclusion and tranquility, with breathtaking mountain views visible from nearly every room in the house, a private pond and miles of walking trails. The peaceful sounds of nature, evening sunsets, and star-filled night skies will have you never wanting to leave. Designed for both relaxed

Mendi Michael Engel & Völkers Okemo

444 Tin Shanty Rd, Cuttingsville, VT 05738
/36
$320,000
- 5 Beds
- 3 Baths
- 2,062 Sq Ft
121 Blanchard Ave, West Rutland, VT 05777

WEST RUTLAND: Very well kept village home has numerous upgrades including a remodeled kitchen with an island, open concept, hardwood floors, upgraded electrical and vinyl siding. In-law apartment upstairs with separate electric and shared heat, along with upper deck. Tenants in main house are month-to-month and pay $1,800/month. Sellers previously lived in the 3-bedroom house and rent from

Melissa Loughan Westside Real Estate

121 Blanchard Ave, West Rutland, VT 05777
/18
$249,000
- 6 Beds
- 4 Baths
- 2,860 Sq Ft
75 Harrison Ave, Rutland, VT 05701

A Four Unit Investment Property.This reasonably well-maintained four-unit property offers two 2 bedroom and two 1 bedroom units, making it appealing to both renters and owner-occupants. This is a “turnkey” rental property, ready to generate income immediately.Located within Rutland City, near downtown shops, schools, parks, and public transportation, this property benefits from strong

Mark Triller Real Broker LLC

75 Harrison Ave, Rutland, VT 05701
/26
$295,000
- 7 Beds
- 3 Baths
- 2,916 Sq Ft
2830 Stage Rd, Benson, VT 05743

Historic, Income-Generating, Multi-Family Property. Turnkey, investor ready, being fully updated with new plumbing, HVAC, wiring, vinyl windows, flooring, appliances, and fresh paint, is ready to own without additional investment.This completely renovated farmhouse (circa 1865) featuring 2,800 sq ft, 7 bedrooms, 3 full baths, and two separate units is ideal for an investor,

Mark Triller Real Broker LLC

2830 Stage Rd, Benson, VT 05743
/33
$399,000
- 5 Beds
- 3 Baths
- 3,164 Sq Ft
1028 Route 4a W, Castleton, VT 05735

Versatile Castleton 3 Unit Compound on .61 Acres – Steps from Lake BomoseenDiscover an extraordinary opportunity, a blend of spacious living, income potential, and lake area lifestyle...... in historic Castleton.Situated on a .61-acre park like lot, graced with stately maple trees, mature landscaping, two Vermont slate patios, a Vermont marble fire pit—with room to expand with a pool or

Mark Triller Real Broker LLC

1028 Route 4a W, Castleton, VT 05735
/43
$200,000
- 5 Beds
- 2 Baths
- 2,947 Sq Ft
29 Woodstock Ave, Rutland, VT 05701

Solidly built city home with a detached two-car garage, ideally located for easy access to shopping, dining, recreation, and more. Inside, the home is ready for a fresh update-offering generous space to reimagine as bedrooms, offices, a library, or creative flex areas. The original hardwood floors are just waiting to be restored to their former charm, and a coat of fresh paint will instantly

Susan Bishop Four Seasons Sotheby's Int'l Realty

29 Woodstock Ave, Rutland, VT 05701
/60
$499,995
- 5 Beds
- 3 Baths
- 3,234 Sq Ft
209 State St, Rutland, VT 05701

Turnkey, upscale duplex located in the heart of Rutland City and minutes from Killington, shopping, events and more! Recently renovated and ready to generate income or support owner-occupancy. This property includes a current occupancy permit so you can Airbnb or the like from day one! This duplex was previously an Airbnb and ski rental. Over 3,200 sq ft of living space with true utility

Jason Saphire www.HomeZu.com

209 State St, Rutland, VT 05701
/50
$277,000
- 5 Beds
- 2 Baths
- 2,620 Sq Ft
44 Cleveland Ave, Rutland, VT 05701

Two-unit Colonial in the heart of Rutland City, an investment or owner-occupant opportunity. Set on historic Cleveland Avenue, this 1909 Colonial offers 2,620 finished square feet on a 0.16-acre city lot. The upper unit features 3 bedrooms and a large porch with mountain views, while the lower unit includes 2 bedrooms with three covered porches. Both units are equipped with washer and dryer.

Rondene E Wanner EXP Realty

44 Cleveland Ave, Rutland, VT 05701
/50
$2,400,000
- 6 Beds
- 5 Baths
- 4,821 Sq Ft
198 Prospect Point Rd, Castleton, VT 05735

ONCE UPON A DREAM-PROSPECT POINT. An extraordinary opportunity to own a 1.73-acre private peninsula with over 560 feet of pristine WATERFRONT on Lake Bomoseen, Vermont’s largest freshwater lake. With expansive western views, unmatched privacy, and direct water access, this custom-built 4,821 sq ft home, completed in 2002, effortlessly blends timeless New England charm with the finest elements of

Freddie Ann Bohlig Four Seasons Sotheby's Int'l Realty

198 Prospect Point Rd, Castleton, VT 05735
/46
$610,000
- 5 Beds
- 1 Bath
- 1,652 Sq Ft
1056 Point of Pines Rd, Fair Haven, VT 05743

Charming 3-Season Adirondack retreat on Lake Bomoseen in Castleton, VT. Lovingly held by the same family for generations, this character-rich Adirondack-style cottage is ready to welcome its next chapter. Nestled within the historic Point of Pines Cottage Colony Association, properties here are a rare find—and for good reason. Association dues are just $400 annually and provide access to a host

Christopher Lawrence Gilbert Realty and Development

1056 Point of Pines Rd, Fair Haven, VT 05743
/45
$739,000
- 5 Beds
- 3 Baths
- 1,874 Sq Ft
118 Tanglewood Dr, Killington, VT 05751

Prime Killington location a few minutes to the Killington Access Road to enjoy the restaurants/ nightlife, and super close to the K1 Base Lodge. Investment Opportunity here! Formally this property has always been a duplex. The current owner decided to make the home a single-family home with the ability for the new owner to turn it back into a duplex if one desired to do so. The town of Killington

Will Spanos KW Vermont-Killington

118 Tanglewood Dr, Killington, VT 05751
/31
$695,000
- 5 Beds
- 4 Baths
- 3,572 Sq Ft
11 Tuttle Meadow Dr, Rutland, VT 05701

BIG, BOLD, AND BEAUTIFUL! Nicely sited colonial on a rare 1.38-acre lot in a quiet Northeast Rutland neighborhood, this elegant custom-built home offers the space, comfort, and quality you’ve been looking for. With over 3,500 sq ft, the home features 5 bedrooms and 4 baths, including a first-floor office with a closet and nearby full bath, ideal for guests or a 6th bedroom. The oversized kitchen

Freddie Ann Bohlig Four Seasons Sotheby's Int'l Realty

11 Tuttle Meadow Dr, Rutland, VT 05701
/59
$2,395,000
- 5 Beds
- 4.5 Baths
- 4,318 Sq Ft
37 High Mountain Rd, Killington, VT 05751

With its massive entry portico, prominent staircase and bold architectural details, this impressive log home evokes the cozy comfort of a grand Adirondack lodge. High ceilings, floor to ceiling glass and prominent stone hearths reinforce the rugged, yet elegant feel. Located within the exclusive Ridgetop Estates development, which consists of only 9 lots, this lovely property is just minutes from

Bret Williamson Killington Valley Real Estate

37 High Mountain Rd, Killington, VT 05751
/5
$985,000
- 6 Beds
- 5 Baths
- 3,817 Sq Ft
3261 Route 30 N, Castleton, VT 05735

LAKE BOMOSEEN DUPLEX - TWO HOUSES WITH INCOME: 1930 Southern house has original frame, but house was totally renovated in 1989 and Northern house was built. Southern house has 4-bedrooms, 2 1/2 baths and Northern house has two 1-bedroom apartments. New electrical, plumbing, insulation, etc. In 2024, houses were stained. Also, includes storage room between the houses and a storage shed near the

Owen Loughan Westside Real Estate

3261 Route 30 N, Castleton, VT 05735
/50
$330,000
- 5 Beds
- 3 Baths
- 2,143 Sq Ft
817 York Street Extension, Poultney, VT 05764

Welcome to 817 York Street Extension in scenic Poultney, Vermont—a turnkey farmhouse setup with room for animals, hobbies, and a relaxed rural lifestyle. This spacious 5-bedroom, 3-bathroom home offers the kind of space that works for real life: whether you’re wrangling family, livestock, or just enjoying the view. The oversized 3-bay garage has full storage above—ready for all your gear or

Betsy Adamovich Real Broker LLC

817 York Street Extension, Poultney, VT 05764
/47
$585,000
- 6 Beds
- 4 Baths
- 3,928 Sq Ft
1851 York Street Extension, Poultney, VT 05764

Rarely does a property offer this much—space, privacy, and resort-style amenities—all in one. Set on nearly an acre, this expansive home features over 5,000 finished sq ft with 6 bedrooms, 4 bathrooms, and flexible living space throughout. Completely rebuilt down to the foundation in 2001, the home offers the peace of mind of modern construction with the charm of a well-established

Mandolyn McIntyre Real Broker LLC

1851 York Street Extension, Poultney, VT 05764
/53
$699,000
- 5 Beds
- 2 Baths
- 1,738 Sq Ft
30 Ridge Rd, Killington, VT 05751

Stunning Turnkey Property in the Heart of Killington – Mountain Views, Modern Comfort, and Outdoor Adventure!Welcome to your dream mountain getaway! This beautifully updated home in Killington blends comfort, rustic charm, and year-round adventure. Whether you're seeking a personal retreat, family vacation spot, or a high-demand investment property, this turnkey gem is ready for

Will Spanos KW Vermont-Killington

30 Ridge Rd, Killington, VT 05751
/34
$629,000
- 5 Beds
- 3 Baths
- 4,335 Sq Ft
36 High Meadow Way, Pawlet, VT 05761

REDUCED 50K! Discover the perfect blend of comfort and convenience at this 5-bedroom, 3-bathroom family home nestled in the scenic landscape of Danby, Vermont. Boasting immaculate construction and unmatched quality, this residence offers the ideal backdrop for both luxurious living and intimate gatherings.Step inside to find spacious interiors that promise a lifestyle of ease and

Brian Hill Remax Summit

36 High Meadow Way, Pawlet, VT 05761
/23
$276,000
- 5 Beds
- 3 Baths
- 2,304 Sq Ft
21-23 Garden St, Proctor, VT 05765

THIS IS THE PROPERTY YOU HAVE BEEN WAITING FOR!! The marble houses in the esteemed town of Proctor have so much rich history and it is rare to have one come to market! A stately duplex home that currently has 2 separate units with all separate utilities and earns a high income - but can easily be converted to a single family home to fit your needs. Both units have enclosed porches on the front

Claire Thompson Real Broker LLC

21-23 Garden St, Proctor, VT 05765
/60
$1,495,000
- 8 Beds
- 5 Baths
- 3,951 Sq Ft
882 Mitchell Rd, Cuttingsville, VT 05738

One of a kind property in Shrewsbury with a renovated four bedroom 1812 Colonial and a four bedroom converted Barn with an in-law-suite that has provided an Airbnb income. All on 137 acres enrolled in the VT Land Trust and Land Use programs, as well as a Forest Management Plan. A sloping terrain and open pastures provide easterly VIEWS of the Taconic mountains for watching the seasons change. The

Sandi Reiber Four Seasons Sotheby's Int'l Realty

882 Mitchell Rd, Cuttingsville, VT 05738
/47
$550,000
- 5 Beds
- 2.5 Baths
- 4,009 Sq Ft
23 Grandview Terrace, Rutland, VT 05701

This Mountain View Colonial comes furnished and when pulling in the driveway you will always see the trees and mountains. This is a luxury retreat, and priced amazing! Don't build, buy and move in, with top of the line frame valued at asking price of home to rebuild. Bring your own creative interior design ideas to finish off the remodel. Enjoy Mountain View's year round in one of the best

Derek Eisenberg Continental Real Estate Group, Inc.

23 Grandview Terrace, Rutland, VT 05701
/33
$265,000
- 5 Beds
- 2 Baths
- 1,936 Sq Ft
56 Church St, Rutland, VT 05701

This multi-family, duplex offers an opportunity to invest in a building that has been renovated, updated, and well-maintained - leaving you minimal maintenance expenses. Fresh paint and flooring; recent roofing and plumbing; and well-maintained mechanicals. The building has a current CO, and is 100% occupied. Unit 1 is on the main floor and Unit 2 on the second floor. Unit 1 includes three

Sue Starr-Adams EXP Realty

56 Church St, Rutland, VT 05701
/42
$1,350,000
- 10 Beds
- 11 Baths
- 5,970 Sq Ft
70 N Main St, Rutland, VT 05701

Exceptional craftsmanship meets modern restoration in this stunning Victorian home. Original features like leaded stained-glass windows, leather wall accents, intricate plaster moldings, and handsome oak parquet flooring highlight its timeless elegance. A grand foyer welcomes you with a 145-year-old handcrafted staircase, while the opulent dining room showcases built-ins and a stained-glass wall

Freddie Ann Bohlig Four Seasons Sotheby's Int'l Realty

70 N Main St, Rutland, VT 05701
/57
$2,250,000
- 5 Beds
- 4.5 Baths
- 4,316 Sq Ft
644 Trailview Dr, Killington, VT 05751

Nestled between two of Killington's most iconic trails, this five-bedroom contemporary offers the ultimate blend of luxury and ski-in/ski-out convenience. Step from your heated ski room, click into your skis or snowboard and hit the Great Eastern ski trail. At day's end, schuss right to your door via the private ski-home trail off the Homestretch run. The striking contemporary design features

Kyle Kershner Killington Pico Realty

644 Trailview Dr, Killington, VT 05751

Showing Results 1 - 40, Page 1 of 2

Vermont Rutland County

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

Rutland County Types of Homes for Sale

Rutland County Real Estate Listings

More About Living in Rutland County

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.