Windham County, CT Real Estate Search

Windham County, CT 5 Bathroom Homes for Sale

Our website features the best real estate search for 5 bathroom homes available in Windham County, CT and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in the Windham County, CT real estate market? Sign up for a  Windham County, CT Real Estate Market Report to see what’s active, under contract, and sold!

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Newest Windham County, CT 5 Bathroom Homes for Sale

$1,100,000
6 Beds ⋅ 5 Baths ⋅ 24194248 MLS
The Fenner-Matthewson Mansion-an extraordinary piece of Connecticut history. Built circa 1855 for prominent mill owner Arnold Fenner, this magnificent Italian Villa is a distinguished contributing property within the National Register-listed Central Village Historic District. Nearly 6,000 SF of timeless grandeur offers 12 rooms, 6 bedrooms and 4.5 baths, with soaring 12' ceilings and exquisite period detail throughout. A grand foyer and sweeping staircase make an unforgettable first impression, complemented by 2 additional staircases, original black walnut doors and millwork, red pine floors, mercury glass doorknobs and beautiful built-ins. An incredible 9 working fireplaces, many with distinctive Italian marble surrounds, grace the home-including fireplaces in the updated kitchen and primary suite. The kitchen blends historic character with modern function, featuring a Sub-Zero refrigerator, pantry and butler's pantry. The primary suite offers a private full bath with soaking tub and fireplace. Recent improvements include a new roof and new central air. Set on 2.65 acres with an inviting front porch, stone courtyard and charming stucco outbuilding. More than a home-this is architecture, history and legacy, awaiting its next steward.

40 Main St, Plainfield
$499,900
4 Beds ⋅ 5 Baths ⋅ 24187565 MLS
Nestled on 11.6 acres of open and wooded land, this spacious farmhouse offers the perfect blend of comfort, privacy, and productive outdoor space. The four-bedroom, four-bath home features an open floor plan that creates a bright, welcoming atmosphere ideal for both everyday living and entertaining. The expansive yard provides ample room for gardening, small-scale farming, or simply enjoying the rural setting. With room to expand or add outbuildings, the property supports a wide range of agricultural or recreational uses while maintaining easy access to modern amenities. Detached garage with workshop, as well as over 100 blueberry bushes, fruit trees and established vegetable garden area are an added bonus. This farmhouse presents a rare opportunity for buyers seeking both a comfortable family home and meaningful acreage in one package.

113 Starkweather Rd, Plainfield
$575,000
5 Beds ⋅ 5 Baths ⋅ 73532742 MLS
Oversized Colonial offering exceptional space, flexibility, and income potential. This well-appointed home features a spacious layout with generous living areas, ideal for both everyday living and entertaining. A separate in-law apartment provides the perfect setup for extended family, guests, or additional rental income, offering privacy and versatility. The main residence showcases classic Colonial charm with expansive rooms, abundant natural light, and a functional floor plan. A two-car garage adds convenience and storage, while the property's layout accommodates a variety of lifestyle needs. Equipped with a Generac generator, this home ensures peace of mind and uninterrupted comfort year-round. Whether you're seeking multi-generational living or an opportunity to offset your mortgage with supplemental income, this property delivers both value and flexibility in one impressive package.

41 Margaret Henry Road, Killingly
$880,000
4 Beds ⋅ 5 Baths ⋅ 24180671 MLS
Welcome to this exceptional custom-built ranch, perfectly situated at the end of a peaceful cul-de-sac in South Woodstock. Offering a great blend of luxury, comfort, and versatility, this impressive home boasts 2,822 square feet of beautifully designed main-level living space, with over 5000 square feet of total finished living area including the private in-law apartment above the garage and the spacious walk-out lower level. Stepping through the front door, be captivated by soaring ceilings, arched doorways, and quality craftsmanship throughout. Generously sized living areas provide the perfect setting for entertaining family and friends, while thoughtfully designed spaces offer comfort and privacy for everyday living. The home features spacious bedrooms, abundant storage, and countless custom details that reflect pride of ownership and meticulous attention to quality. Come see this property to see all that it offers.

48 Grey Fox Lndg, Woodstock
$2,950,000
4 Beds ⋅ 5 Baths ⋅ 24115278 MLS
A rare and refined country estate offering privacy, luxury, and elegance on over 53 acres in scenic Pomfret. This extraordinary 4,442 sq ft custom, Tennessee fieldstone home includes 4 bedrooms and 5 baths-including a private in-law apartment/second primary suite with its own entrance. An additional 16+ acre building lot provides development potential. Surrounded by forest and adjacent to 175 acres of open space, this home sits high with long eastern views into RI! A 1,000 ft paved driveway leads past over 500 ft of hand-laid stone walls to the stunning residence, framed by 10" cedar columns and solid mahogany double doors. The interior exudes craftsmanship with 8' solid wood doors, mahogany floors, 12" triple crown molding, and Marvin windows throughout. The grand great room boasts 20' ceilings and a massive fieldstone fireplace, while the private office stuns with a redwood ceiling, fireplace, and custom cherry built-ins. The chef's kitchen features Viking and Meile appliances, granite counters, cherry details, and opens to a sunny morning room and expansive veranda. The primary suite is a retreat with vaulted ceilings, a luxurious spa bath, radiant heated travertine floors, custom vanities, arched alcoves, and dual walk-ins. Additional highlights include a 3-car garage with Spanish cedar doors, Sonos sound system, generator, 139-head irrigation system, and walk-up basement ready to finish. This is a one-of-a-kind legacy property -stately, expansive, and exquisitely built.

282 & 260 Searles Rd, Pomfret
$639,777
10 Beds ⋅ 5 Baths ⋅ 24177946 MLS
Income producing multi family property offering a strong opportunity for investors or owner occupants alike. One unit is currently not leased, providing immediate leasing potential or flexibility for owner occupancy. Property presents the opportunity to generate rental income with additional upside potential over time. Detached garage offers added utility with potential for storage, workshop space, or future supplemental income opportunities. Conveniently located near Eastern Connecticut State University, downtown Willimantic, shopping, dining, and major commuter routes. Great opportunity to add a multifamily asset to an investment portfolio.

120 North St, Windham
$1,150,000
6 Beds ⋅ 5 Baths ⋅ 24172480 MLS
At the end of a long private drive on six rolling acres sits the 1880 Clark Cottage at Wintergreen, a Pomfret estate on the National Register of Historic Places. It's a rare antique that asks nothing of you: 19th-century craftsmanship paired with a fully renovated chef's kitchen and a spa-inspired primary bath, impeccably maintained throughout. Approximately 5,000 square feet span three finished levels and six bedrooms. The remodeled kitchen features custom quartz countertops and sink, a butler's pantry, and a sunlit breakfast nook opening to a living room and sunroom. Formal and casual living rooms, a formal dining room, and an expansive porch handle everything from quiet nights to large gatherings. The primary suite offers a sitting area, balcony, walk-in closet, and renovated bath. A bonus room over the garage and a finished top floor add flexibility for guests, offices, or multi-generational living. Outside is real seclusion: open lawn, mature trees, and room for gardens, set well back from the road yet minutes from Putnam, Woodstock, and the area prep schools, with Hartford, Providence, and Boston within easy reach. Move-in ready and genuinely private.

354 Pomfret St, Pomfret
$1,550,000
5 Baths ⋅ 73495303 MLS
Abutting lot consisting of 3.18 acres included in the sale. Located in the Woodstock Industrial Park, this versatile 10,000 sq ft metal building offers endless possibilities for industrial, manufacturing, or storage use. The property features two overhead doors-one 14'x16' and one 12'x12'-providing easy access for large equipment or vehicles. Inside, the 18-foot ceiling height (to fans and lights) offers excellent vertical clearance, with 42-inch exterior doors. The building includes five restrooms, a mezzanine for added storage or office space, and is equipped with a brand-new, never-used oil furnace as well as an outdoor woodstove. With powerful 3-phase 220V, 400-amp service to both units, this property is ready to support high-demand operations. Situated in an industrial zone with room to expand, this is a prime opportunity for businesses looking to grow in a well-established location. Conveniently located just 29 miles to Worcester, 35 miles to Providence, and 47 miles to Hartford,

30 Crabtree Lane, Woodstock
$1,200,000
5 Baths ⋅ 73471397 MLS
Located in the Woodstock Industrial Park, this versatile 10,000 sq ft metal building offers endless possibilities for industrial, manufacturing, or storage use. The property features two overhead doors-one 14'x16' and one 12'x12'-providing easy access for large equipment or vehicles. Inside, the 18-foot ceiling height (to fans and lights) offers excellent vertical clearance, with 42-inch exterior doors. The building includes five restrooms, a mezzanine for added storage or office space, and is equipped with a brand-new, never-used oil furnace as well as an outdoor woodstove. With powerful 3-phase 220V, 400-amp service to both units, this property is ready to support high-demand operations. Situated in an industrial zone with room to expand, this is a prime opportunity for businesses looking to grow in a well-established location. Conveniently located just 29 miles to Worcester, 35 miles to Providence, and 47 miles to Hartford, with room to expand on-site, this is a smart opportunity.

30 Crabtree Lane, Woodstock
Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.