5-Bedroom Homes for Sale in Windham County CT

Discover this UNIQUE 5 Bedroom, 4-1/2 Bath Gambrel Colonial nestled on 1.49 acres. NEW SEPTIC TANK Installed 2025! This 3,886 Sq Ft home offers a spacious layout including 2 Primary Bedrooms sharing an Ensuite Bath with SAUNA and Whirlpool Tub. WHEELCHAIR ACCESSIBLE design featuring an ELEVATOR/LIFT (Dumbwaiter) to reach all floors and also a LIFT from driveway to deck for easy access into the

Mary Ann Bohonowicz Berkshire Hathaway NE Prop.

Built in 1750 and celebrating its 275th anniversary, this distinguished Colonial farmhouse remains a pristine exemplar of early New England architecture. Set on 8.5 acres, the estate features a secluded pond, a gently winding brook, and two traditional barns-all original to its historic rural setting. This graceful home offers 4 bedrooms, 2 full bathrooms, and approximately 2,443 sf of living

Adam Gumula Kazantzis Real Estate, LLC

Welcome to the exquisite Ebenezer Stoddard house built in 1800 once an inn for travelers on an early state route. This 4100 sq ft home is filled with character, history and updates for modern convenience, while saving the historic charm! The home resides on an 1.2 acre lot, mostly cleared with plenty of room for family gatherings of any size! Entering the home into an official mudroom - leave

Kerri Mullen CR Premier Properties

INVESTORS & OWNER OCCUPANTS, TAKE NOTICE!!! Welcome to 21-27 Union St located in Moosup. This 3-family home offers 9-bed, 4-baths, full basement & a great attic for additional storage as well as 0.1 acres on a corner lot. Tenants will convey. Seller is motivated, bring ALL offers!!!

Patrick Precourt Dorrance Realty

INSTANT EQUITY in this beautiful and incredibly spacious two-family home. Sellers just had the home independently appraised for more than their asking price! With 10 foot ceilings throughout this turn of the century manse, the first floor unit features over 2,100 sq ft of living space with 3 large bedrooms, formal dining room, 2 full baths (1 roll-in handicap accessible, fully tiled with shower

Gerard Hartmann Rockoff Realty

Welcome to your private country retreat in the heart of Thompson! This expansive 5-bedroom, 3.5-bathroom ranch-style home offers 2,622 square feet of versatile living space, including a full in-law apartment-perfect for multi-generational living, guests, or possible rental potential. Set on 4.6 acres the property features two beautiful stone patios, a partially fenced-in backyard, a gardening

Brendan Meehan RE/MAX Bell Park Realty

"Exceptional Investment Opportunity in Putnam CT, 8-unit property featuring two separate buildings on a generously sized lot, offering both immediate income potential and exciting development prospects. Building 1 stands ready for immediate occupancy, featuring 4 Unite 1 bed each, meticulously maintained and prepared for new tenants. while you explore options for the second building. Building 2,

Karim Douich William Raveis Real Estate

Unlock the potential of this spacious, well-maintained townhome style two-family property, perfect for both investors and owner-occupants located at 12 Saint James Row! Each unit boasts nearly 1,200 sq. ft. of living space, featuring 3 bedrooms and 1 bath. Both tenants are month to month. Recent upgrades include painted exterior aluminum siding, replacement windows, along with updates to both

Benjamin Carbone Lamacchia Realty

OPEN HOUSE SAT. 12-2. SHOWINGS START IMMEDIATELY! Spacious 4-5 BR home in Putnam, transformed from mixed-use to fully residential. Originally a 1950 ranch, a 2007 addition expanded the upper level and finished the lower level—now a family room, bedroom, and full bath, ideal for in-law use. There's a place to add a stove/fridge for an additional kitchen. And also has an extra rec area. A 2014 rear

Maribeth Marzeotti Lamacchia Realty, Inc.

Need space for a growing family or in-home business? This remodeled 5-bedroom, 3-bath ranch-style home offers it all! Situated on a large, level .73-acre lot in a peaceful cul-de-sac, this property features a accessible ramp and along with one of three bathrooms. The rear facing open family room has cathedral ceiling,huge windows and skylights with access to a large deck .Combined with the

Vito Uva Scalzo Real Estate

Tucked away on 6.5 private acres in the prestigious MillBrook Estates, this 5,000+ sq ft custom home offers an exceptional blend of elegance, functionality, and luxury. A long paved drive leads to this stately residence, featuring 5 bedrooms, multiple living areas, and rich architectural details throughout. The grand foyer with a hydraulic chandelier sets the tone for the craftsmanship found

Katie Totten William Raveis Real Estate

Investor alert! This professionally managed, fully occupied 5-family property is a rare turn-key opportunity delivering strong and consistent cash flow. All five units are currently leased, making this a seamless addition to your portfolio with income from day one. The building features a new roof. Tenants pay for their own electric heat and hot water, keeping operating costs low for the owner.

Jason Pollard Compass Connecticut, LLC

Welcome to this beautifully updated 5-bedroom, 2-bathroom home offering a perfect blend of comfort and modern style. With 8 spacious rooms, this property features a thoughtfully renovated kitchen and bathrooms, making it move-in ready for its next owner. Situated on a private and secluded 0.14-acre lot, the home provides rare peace and privacy while still being conveniently located. Enjoy the

Kevin Brignole Spaulding Realty Group, LLC

PROMINENT 55-ACRE EQUESTRIAN FACILITY w/PRIMARY 6,000SF RESIDENCE w/2 APARTMENTS! Nestled amid a peaceful countryside, this exceptional horse property presents a rare opportunity to acquire a versatile estate that seamlessly combines elegant residential living w/impressive equestrian facilities. A turnkey sanctuary for those seeking solitude, sophistication, & functionality. A private gated entry

Kiara Rusconi William Raveis Real Estate

Charming 2-family home in Killingly, CT, offering strong investment potential or multi-generational living! The first unit features 4 spacious bedrooms and 1 full bath, while the second unit offers 3 bedrooms and 1 full bath-perfect for rental income or extended family. This property is brimming with potential and awaits your personal touch and TLC to truly shine. Located in an incredibly

Kyle Seyboth Century 21 Limitless

Hill Section of Willimantic, this beautifully well maintained Victorian Home at top of the hill offers rest and relaxing in quiet classic neighborhood. Many original features including pocket doors, moldings and stained glass window. Hardwood and tile throughout. 5 bedrooms, 2.5 baths, finished attic and finished basement with kitchenette and bath for in-law unit for potential rental income. 2

Kathy Dubay I.M.A. Realty LLC

ATTENTION INVESTORS!!! This incredible 10 CAP investment Opportunity for 4 units across 2 2-family properties may be exactly what you're looking for!!! Discover the potential in this centrally located low overhead property. With strong rental demand from nearby ECSU, Uconn and in the general market, vacancy will not be a problem. Tenant amenities include large backyards, with privacy and gardens.

Robyn Letourneau Berkshire Hathaway NE Prop.

INVESTORS TAKE NOTE!! LOW VACANCY in Windham county. 5-unit Investment Property with Strong Cash Flow! Located in the heart of Willimantic, this fully occupied property offers easy maintenance, off street parking, and stable tenants. GOI: $82,560 Other income: $2400 Expenses: $71,628 NOI: $71,628 12 CAP Combine with other listed willimantic properties: Elm st., Jackson St., and Pleasant St. as a

Robyn Letourneau Berkshire Hathaway NE Prop.

MOTIVATED SELLER!!! COME CHECK OUT THIS AMAZING PROPERTY! Own your own beautiful property in Thompson Ct and have your mortgage paid. This property offers ample living space with large apartments. The huge back yard is private and offers shade and a beautiful tree line. This property has off street parking with ample of garage space. Enjoy your own workshop that is heated and offers plenty of

Tessa Stacy Brunet and Company Real Estate

Terrific Investment Opportunity! Don't miss this rare chance to own a well-maintained multi-unit property with strong income potential. The main house features a spacious layout with 5 bedrooms, ideal for large households or rental flexibility. Behind the main home, you'll find a separate 2-bedroom unit, perfect for extended family or additional rental income. Additionally, there's a third unit-a

Tammy Arute Arute Realty Group LLC

349 Pomfret Street, Pomfret Center, Connecticut - Historic Charm Meets Modern Living Step into New England history with this beautifully restored property in the heart of Pomfret Center. Originally known as Stilleben Cottage, this stately home is one of just twelve original Bradley Cottages and is proudly listed on the National Register of Historic Places. Formerly the Cobscroft Inn, the

Jennifer Mahr RE/MAX Bell Park Realty

Amazing opportunity to own a 2-unit home offering 3 bedrooms, and 2 baths each side with its own laundry. The right side was completely gutted in 2024 and renovated from the ground up, with NEW insulation, sheetrock, vinyl plank flooring, Windows, splitters for heat & AC, Kitchen with 5 appliances and 2 full baths. Outside the home has a new roof, siding, asphalt driveways, porch and deck, and

Pat Malek First Choice Realty

TWO HOUSES ON ONE PROPERTY! This unique investment opportunity at 87-89 North Street in Willimantic, CT, presents a compelling proposition for investors. The property comprises TWO single-family homes situated on a single lot, each with its own driveway and access to a large garage located conveniently on the front house's driveway. The rear house, a charming 1,224 square-foot dwelling,

Toni Iandoli William Pitt Sotheby's Int'l

2 family house on a quiet street. First floor is a 2 bed 1 bath with hardwood floors throughout. Direct access to their side of the basement. Front foyer, eat in kitchen, living room. Second unit is the 2nd floor & 3rd floor and open, perfect for owner occupied multifamily. 2 bedrooms on the upper level with new carpet. Kitchen, dining room, living room, bathroom and 1 bedroom on the second floor

david breau eXp Realty

Approved Residential Development Opportunity - Dayville, Killingly, CT Prime development land approved for 14 duplex buildings in the Dayville section of Killingly. This exceptional opportunity sits on land currently generating rental income from three existing structures: a two 2-family home and a mobile home. The property offers dual access from Ware Road and Pineville Road, and the proposed

Claudia Bergstrom RE/MAX Diverse

A rare investment opportunity located in beautiful Woodstock, CT! This 4 unit property is a blank slate to set your own rents, procure your own tenants, or owner occupy. These completely remodeled units feature stunning floors, tiled bathrooms, granite counters, and all have appliances. 2 bed/ 1 bed set up. Coin op laundry available. Close to Woodstock Academy and the Hyde School. Sits on a

Amy Brunet Brunet and Company Real Estate

Attention Investors! Rare opportunity to own a 12-unit brick multifamily building in desirable Brooklyn, Connecticut. This well-maintained property features a diverse mix of units offering both ranch-style one-bedroom, one-bath units on the first floor and townhouse-style two-bedroom, one-bath units on the second floor, offering a total of 12 units to rent. The building is currently fully

Anthony Chabot Chabot & Associates Real Estate

Attention developers and investors! Rare opportunity to acquire a former school building and convert it into a multifamily complex or condominiums. 18,600sf plus just under 9,000sf of finished basement space with abundant natural light. Average classrooms range from 600-800 sq. ft. Otis elevator, extensive ADA-compliant bathrooms, and ramps. Equipped with a natural gas boiler, central heat, hot

Anthony Chabot Chabot & Associates Real Estate

Nestled in the tranquil corner of Eastford, CT, this expansive 5-bedroom, 3.5-bathroom ranch offers a serene escape on a generous 8.7-acre lot. With a two-car attached garage and a sprawling wrap-around porch, this home invites you to enjoy the peaceful outdoors and picturesque surroundings. As you step inside, you're greeted by soaring cathedral ceilings and an open floor plan that seamlessly

Melissa Guerrero William Pitt Sotheby's Int'l

Welcome to a unique chance to own a spacious multi-family property in the charming South Windham area. This home presents an outstanding opportunity for investors seeking rental income and invites a creative new owner to explore the renovation potential. With a total of five bedrooms and two bathrooms spread across 2,548 square feet, this property is ideal for offering flexibility to operate as a

Franchesca Pescatello Prue Realty LLC