Cheshire County, NH Multi-Family Homes for Sale

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Newest Cheshire County, NH Multi-Family Homes for Sale

$395,000

5102758 MLS

Two homes, eight bedrooms, and one exceptional investment opportunity in the heart of Keene! 40 Myrtle Street is a two-unit multifamily property, with each unit offering four bedrooms and two full bathrooms. Both feature functional, two-level layouts with generous living spaces and in-unit washer and dryer hookups. One residence, originally built in 1870, was completely renovated in 2011, while the second was newly constructed that same year. Each unit has separate electric, heating, and water utilities. Additional features include a three-year-old tankless heating system in Unit 2, two 110-amp electrical panels, town water and sewer, vinyl siding, ample off-street parking, yard space, and tenant-paid utilities. The spacious layouts offer flexibility for comfortable everyday living, home offices, storage, or bonus space. While the property is ready for cosmetic updates, its major systems have been maintained. Conveniently located just minutes from Keene State College and downtown Keene, with shopping, restaurants, the bike path, and everyday amenities nearby. Nearby major highways provide convenient commuting options. Whether you’re seeking rental income or a smart live-in investment, this property is well positioned to become a cornerstone of your portfolio. Unit 1 is leased through December 31, 2026, and Unit 2 is leased through September 15, 2026. Tenant occupied; 48-hour notice is required for all showings.

40 Myrtle St, Keene

Listing courtesy of Isabella S Luhrs from BHG Masiello Keene. ()

$340,000

5102168 MLS

Spacious 2 unit multifamily property offering a three-bedroom, two-bath main home and an attached one-bedroom rental unit. Filled with natural light, the main home offers a warm and inviting atmosphere throughout. Enter the main unit through a charming mudroom that opens into a bright, spacious living room, dining area, and kitchen with updated appliances. A full bathroom completes the first floor. Upstairs, you’ll find three bedrooms, including a generously sized primary bedroom, along with a second full bathroom. The attached one-bedroom unit can be accessed through an interior hallway or through its own private entrance, offering flexibility and privacy. The quaint one-bedroom unit is ideal for rental income, extended family, guests, or an in-law setup. This unique property includes a second lot located directly across the street, bringing the total acreage to just over two acres. The additional lot features a peaceful pond and a private bridge, creating a beautiful outdoor retreat with endless possibilities. A detached two-car garage and a newer storage shed provide plenty of space for vehicles, tools, and outdoor equipment. Whether you’re looking for an owner-occupied investment, multigenerational living, or additional income potential, this property offers a rare combination of space, versatility, and the added bonus of a scenic second lot across the street. Property will be delivered vacant.

2 W Hill Rd, Troy

Listing courtesy of Linda F Desaulniers from ERA Key Realty Services. ()

$650,000

5100845 MLS

A rare opportunity for investors and owner-occupants alike in Marlborough, New Hampshire. Built in 2004, this four-unit apartment building offers immediate income with outstanding long-term investment potential. Set in a peaceful country setting just minutes from Route 101 and Keene, the property has the advantages of newer construction in a location with consistent rental demand. Each of the four apartments features a desirable two-bedroom layout, ample parking, a shared deck and porch, and the efficiency of a Buderus boiler. Live in one unit while generating income from the others, or add a well-maintained multifamily property to your investment portfolio. Private well and public sewer. There is also an outbuilding that can be used for storage or a workshop. Residents enjoy all that the Monadnock Region has to offer, including nearby hiking and outdoor recreation, scenic lakes and trails, an authentic small-town atmosphere, and convenient access to shopping, healthcare, dining, and entertainment.

59 Old Chesham Rd, Marlborough

Listing courtesy of Peg Walsh from Four Seasons Sotheby's International Realty. ()

$435,000

5097930 MLS

Dreaming of riverfront living with income potential? This one-of-a-kind multi-family property overlooks the scenic Cold River, renowned for its excellent fishing opportunities. Rich in history, the building was originally a grist mill and has been thoughtfully converted into a three-unit multi-family property while preserving much of its original character. The first floor apartment is a beautifully updated one bedroom unit offering comfortable, modern living. The remainder of the first floor serves as an inviting common area featuring the building's stunning original brick walls, showcasing the property's historic charm. From this shared space, you'll find access to the expansive basement, ideal for storage or workshop space, as well as the staircase leading to the second-floor apartment. The second-floor apartment is truly exceptional, featuring soaring cathedral ceilings and original wide plank hardwood floors. The spacious layout includes a bedroom, full bath with laundry, and an open-concept living area with designated spaces for the kitchen, dining, living room, and a family room or home office. Two unique lofts, each with its own staircase, provide flexible space for sleeping, hobbies, or additional storage. A detached two-car garage offers plenty of room for vehicles along with a generous workshop area. Above the garage is a private one-bedroom apartment complete with its own entrance, a side deck, and a rear deck overlooking the picturesque Cold River the perfect place to relax and enjoy the peaceful waterfront setting. Whether you're looking for an investment property, multi-generational living, or a unique riverside retreat with rental income, this remarkable historic property in Alstead NH on 5 plus acres offers endless possibilities in a truly special location.

87 Mechanic St, Alstead

Listing courtesy of Robin N Sanctuary from Traditions Real Estate LLC. (Cell: 603-313-9165)

$250,000

5097695 MLS

A rare opportunity to own a side-by-side duplex! Live in one unit and rent the other to help offset your mortgage, or maximize your investment by renting both units. Ideal for owner-occupants, investors, or multi-generational living, this versatile property offers strong income potential with long-term rental history. Each unit has separate utilities, washer and dryer hookups in the basement, and private living space. Major improvements include a new leach field (2013), new roof and trusses (2014), new siding and windows (2015), and a new well pump with a 30-gallon expansion tank (2024). Conveniently located between Keene, NH, and Brattleboro, VT, offering easy access to shopping, dining, employment, and recreation.

523 Chesterfield Rd, Hinsdale

Listing courtesy of Anna Schierioth from HKS Associates, Inc.. ()

$389,000

5097311 MLS

Charming Craftsman-style two-family home lovingly maintained by its second owners and beautifully preserved with timeless character throughout. Ideally situated on a large corner lot in a desirable location, this property offers an exceptional opportunity for both homeowners and investors. The spacious owner's apartment features three bedrooms, gleaming pine floors, beautiful wide archways, high ceilings, abundant natural light, and a welcoming enclosed front porch. The second-floor apartment offers two bedrooms, generous storage, attractive period details, and bright, comfortable living spaces that reflect the same classic Craftsman charm. Perfect as an owner-occupied investment, this property allows you to enjoy the comfort of your own home while generating rental income. Additional highlights include an attached garage for the owner's unit, a separate tenant carport, ample parking, and mature landscaping. A rare combination of architectural character, pride of ownership, income potential, and an outstanding location.

252 Church St, Keene

Listing courtesy of Ryan Goodell from EXP Realty. (Cell: 603-313-7541)

$300,000

5095179 MLS

Nestled in the heart of Swanzey, this beautifully refreshed two-family home perfectly captures the essence of peaceful country living while sitting just ten minutes from all the shopping, dining, and amenities of Keene. Recently renovated inside and out, this turnkey property blends modern updates with an abundance of classic character, including gorgeous hardwood floors flowing throughout both units. The front unit offers a spacious three-bedroom, one-bathroom layout that is perfect for an owner-occupant, while the back unit features a cozy two-bedroom, one-bathroom setup with rental history and a reliable current tenant who could continue month to month, offering immediate income from day one. Convenience is key with dedicated in-unit laundry in both apartments. Outside, the property boasts incredible curb appeal with a sprawling, large yard that provides plenty of space for outdoor activities, complemented by two large porches on either side of the house that are ideal for relaxing. Storage is never an issue thanks to a handy on-site shed and additional storage space along the side of the house. Open house 7/2 from 4-6pm and 7/3 from 12-2PM!

28 Christian Hill Rd, Swanzey

Listing courtesy of Maria Stika from Keller Williams Realty Metro-Concord. ()

$295,000

5094178 MLS

Charming 2 unit New Englander located in the village of North Walpole which is convenient for commuting being close to I91, 30 min to Keene or Claremont. Each unit has separate heat, electric, hot water. Both units have 2 bedrooms, 1 full bath, eat in kitchen, laundry hook up, period built ins, spacious light filled rooms and porch entrances. Side porch is two story, great place to hang out.

34 Center St, Walpole

Listing courtesy of Robin N Sanctuary from Traditions Real Estate LLC. (Cell: 603-313-9165)

$259,900

5094140 MLS

2 UNIT FARMHOUSE STYLE MULTIFAMILY OR SINGLE FAMILY ON 1.2 ACRES. ATTACHED BARN/2 CAR GARAGE. AMPLE PARKING. GREAT FOR OWNER OCCUPIED, MULTIGENERATIONAL OR INVESTOR. PREVIOUS OWNER USED PROPERTY AS A SINGLE FAMILY. RADIATES COMFORT, CHARACTER AND CHARM WITH SPACIOUS ROOMS AND HANDSOME FLOORING. STRIKING INTERIOR WITH A MODERN TOUCH. RECENTLY UPDATED. ATTRACTIVE LANDSCAPING. WALKING DISTANCE TO TOWN CENTER. CONVENIENT ACCESS TO KEENE, MA & VT. THIS PROPERTY PROUDLY AWAITS YOUR ARRIVAL.

65 Mechanic St, Winchester

Listing courtesy of Shirley Marcello from BHG Masiello Keene. ()

$408,000

5093890 MLS

Opportunity, flexibility, & character come together in this exceptional bungalow style multi family property offering over 2,300 sq ft of living space & endless possibilities for owner occupants, investors, multi generational living, or those seeking a live/work lifestyle. The spacious main residence features 4 to 5 bedrooms & 1 full bath, showcasing the timeless charm of a classic bungalow with beautiful hardwood floors, original woodwork, tall ceilings, abundant natural light, & generously sized rooms throughout. The well appointed kitchen features granite countertops, stainless steel appliances, custom cabinetry, & exposed brick accents, blending modern convenience with the home's character & craftsmanship. The oversized living room serves as the heart of the home, highlighted by a gas fireplace, expansive windows, & views overlooking the stunning covered front porch. The primary bedroom also features its own gas fireplace, creating a warm & inviting retreat. A standout feature of the main level is the front bedroom with its own private exterior entrance, previously utilized as a business, offering exceptional flexibility for a home office, studio, guest space, or additional bedroom. The second floor features an exceptionally large 1 bdrm apt complete w a full kitchen, bath, spacious bedroom, & an enormous living room that sets it apart from typical rental units. Ideal for rental income, multi generational living, or extended family accommodations. Outside, the expansive covered front porch serves as a true extension of the home, providing the perfect place to relax, entertain, or enjoy your morning coffee. Properties offering this level of flexibility, character, architectural charm, & income producing potential are increasingly difficult to find. Whether you're looking to offset your mortgage w rental income, accommodate extended family, or expand your investment portfolio, this unique property delivers exceptional versatility, space, & opportunity.

77 High St, Hinsdale

Listing courtesy of Kirsten Perkins from BHG Masiello Keene. ()

$499,000

5093731 MLS

Tucked away on approximately 12.44 +/- private acres in one of New Hampshire’s most picturesque towns, this lovingly maintained custom-built home offers a rare opportunity to embrace the lifestyle you’ve always imagined. Thoughtfully designed to celebrate nature, gardening, and year-round beauty, every corner of this property reflects a deep appreciation for the land it occupies. Awaken each morning to the soothing sounds of the stream flowing behind the home as sunlight filters through the trees. Step directly from the primary bedroom onto your private deck overlooking the water, coffee in hand, and begin your day surrounded by the sights and sounds of nature. Inside, abundant natural light and inviting living spaces create the perfect environment for thriving houseplants, while established gardens outdoors provide endless opportunities for those with a passion for cultivating beauty. Currently configured as a two-family residence, the home offers exceptional flexibility for today’s lifestyles. Continue using it as an income-producing property, create a private space for multi-generational living, accommodate a live-in caretaker, or easily convert it back to a spacious single-family home. Adding to the property’s unique appeal, the Cheshire Rail Trail abuts the property, offering direct access to miles of scenic recreation right from your backyard. With ample acreage, complete privacy, and room to expand, the possibilities are limited only by your imagination. Rich in history and New England charm, Westmoreland provides the backdrop for a life well lived. Whether you’re seeking a peaceful retreat, a homestead, a family compound, or simply a place to put down roots, this remarkable property invites you to write the next chapter of your story here. This is more than a home—it’s a lifestyle. And it just may check every box, including the ones you didn’t even know you had.

68 Mount Gilboa Rd, Westmoreland

Listing courtesy of TJ Kelly from Greenwald Realty Group. ()

$475,000

5093431 MLS

ATTENTION INVESTORS! Fully occupied 4-unit apartment building with a strong rental history and excellent income potential at 305 Richmond Road, Winchester, NH. This well-maintained multi-family property is located near the Massachusetts border, offering convenient access for commuters and tenants from both states. The property includes four residential units that are currently 100% occupied with reliable long-term tenants. It also features two separate income-producing workshop/garage spaces that provide additional revenue streams and enhance overall cash flow. Recent major capital improvements include a brand new roof, newly replaced rear stairs and decking, a fully replaced leach field, and septic connections to the two 1,000-gallon tanks that were serviced and replaced where needed. These updates ensure the property is in excellent condition and reduce future maintenance costs for the new owner. Tenants pay their own heat, hot water, and electricity, which keeps operating expenses low. This property has consistently delivered positive cash flow to the current owner, and keeping it occupied has never been an issue thanks to strong local demand. Current rents are below market rate and the leases are expiring, creating an immediate upside opportunity for a new owner to implement market-rate increases and boost net operating income right away. Whether you are an experienced investor looking to add a turnkey, low-maintenance asset to your portfolio or a buyer seeking a solid, cash-flowing property with built-in equity through recent upgrades, 305 Richmond Road is worth serious consideration. Priced to attract serious investors — schedule your showing today and see the value for yourself. Whether investor-owned or owner-occupied, 305 Richmond Road is a super income generator and can be yours with pride. This property is not going to last long!

305 Richmond Rd, Winchester

Listing courtesy of Jack Garber from Coldwell Banker Realty Nashua. (Cell: 603-274-9010)

$509,000

4 Beds ⋅ 5086183 MLS

Welcome to 84 Elm Street, an exceptional two-family property offering flexibility, charm, and income potential, just a five-minute walk from bustling downtown Keene. Whether you're looking to owner occupy while offsetting your mortgage, or need a smart layout for multi-generational living, this home is ideally suited for both. Each unit provides comfortable, separate living spaces, while the property itself offers a rare combination of character and modern updates. The first-floor unit features a beautifully renovated kitchen and bathroom (2023), blending functionality with thoughtful design. Upstairs, you’ll find unique details, including a striking tile mosaic of Mount Monadnock in the kitchen, adding a true sense of place and craftsmanship. Recent improvements include new 200-amp electrical service for both units (2023), all new windows (2025), and a new water heater (2026), giving the new owner peace of mind for years to come. Outside, the property continues to impress. A large, paved driveway provides ample parking for multiple vehicles, as well as space for an RV or boat. The expansive backyard is a standout feature, complete with trees, blueberry bushes, a large grape arbor, raised vegetable gardens, and established perennials, perfect for relaxing, entertaining, or gardening enthusiasts. Additional highlights include a two-car garage equipped with a Level 2 EV charger, along with a spacious barn and workshop offering excellent storage or hobby space. This is a rare opportunity to own a well-built, thoughtfully updated multi-family home in a highly walkable Keene location, ideal for both homeowners and investors alike. The owner is a licensed real estate salesperson in the State of New Hampshire.

84 Elm St, Keene

Listing courtesy of George Hansel from H. G. Johnson Real Estate. ()

$550,000

5085975 MLS

15 High St consists of two buildings on the parcel, containing two (2) 2-Bedroom/1-Bathroom units and six (6) 1-Bedroom/1-Bathroom units with 4,519 square feet of gross living area in 7,739 square feet of gross area. The Property is situated upon a 0.68-acre parcel and features ample off-street parking spaces. 15 High Street is well situated within the town center of Winchester, offering direct access to the area’s small-town commercial corridor, local services, and surrounding residential neighborhoods. Tenants are responsible for electric powered hot water and separately metered electricity in Units 1-5 and 8, while the Landlord is responsible for paying for Units 6 and 7. The Landlord is responsible for providing oil powered heat to Units 1-5 and 8, while tenants are responsible for propane powered heat in Units 6 and 7. The Landlord is responsible for providing public water & sewer to all units. 15 High Street benefits from a village-center location in Winchester, NH, placing it within a short walk of Main Street and local services while offering straightforward regional roadway access via NH Route 10 and nearby NH Route 119. In-place rents are below the current market rates; the opportunity exists to continue to upgrade unit interiors and common areas to drive rental rates in an supply constrained residential market.

15 High St, Winchester

Listing courtesy of William Peck from Horvath & Tremblay LLC. ()

$500,000

5085743 MLS

27 Proctor Court contains five (5) 1-Bedroom/1-Bathroom units with 2,032 square feet of gross living area in 4,243 square feet of gross area. The Property is situated upon a 0.09-acre parcel and features five (5) off-street parking spaces. The Property is well-positioned in Keene’s established residential neighborhood, offering convenient access to the city’s downtown core, neighborhood retail corridors, and surrounding community amenities. Tenants are responsible for gas-powered heat & hot water, as well as individually metered electricity, which they pay directly. The Landlord is responsible for providing city water & sewer, which they pay directly. Local public transit is available via Keene’s City Express bus system, a fixed route service that operates weekdays and serves approximately 30 stops across the city, including downtown, major retail centers, residential neighborhoods, and the Cheshire Medical Center, placing several stops within a short walk of the property given its proximity to Main Street and the core commercial area. The presence of Keene State College creates an additional layer of rental demand from students, faculty, and staff.

27 Proctor Ct, Keene

Listing courtesy of William Peck from Horvath & Tremblay LLC. ()

$1,500,000

5085710 MLS

Don’t miss this unique 13-unit multifamily property just a short drive to downtown Keene. Set on 1.7 acres, this property stands out in the market by offering tenants individual, standalone cabin-style homes. providing privacy and a neighborhood feel rarely found in rental properties. The property will be fully occupied as of July 2026 and will offer a strong 8.7% CAP rate, making it an attractive option for investors seeking reliable income. Several tenants have occupied their units for decades, demonstrating consistent demand and long-term stability. Significant recent improvements include the complete reconstruction of two cabins over the past two years, adding modern, high-quality units to the property. With its appealing layout, stable occupancy, and convenient location near shopping, employment, and services in Keene, this property is well-positioned for continued performance. Financials and leases available to qualified buyers upon request.

90 Monadnock Hwy, Swanzey

Listing courtesy of George Hansel from H. G. Johnson Real Estate. ()

$290,000

5077669 MLS

INVESTORS WANTED. This property is just a few minutes away from downtown Winchester. 3 units are occupied. Tenants pay on time and would like to stay. Some have been here for many years. Property needs some repairs. The mostly open 3 acre parcel offers the tenants plenty of space for outdoor activities. Showings are limited due to tenants works schedules. Property is being sold without further repairs. *This will need a CASH BUYER*. Please allow 48 hr notice. Weekend showings only.

292 Richmond Rd, Winchester

Listing courtesy of Jonathan L Bafundi from Realty One Group Next Level. ()

$749,000

5073973 MLS

This mixed-use property features a spacious, dedicated office which comprises the complete first floor, ideal for remote work or running a home-based business. The office offers ample room for multiple workstations, built-in storage, and abundant natural light, creating a productive and comfortable environment. The 7-room office has reception area, large conference room, 3 private offices and a open work room. It has a galley kitchenette with full sized refrigerator, microwave and plenty of kitchen workspace for coffee make, etc. Office space also two tiled 1/2 baths for use of clients and employees. The thoughtful lay out of the office could easily be divided into an apartment with room for an office, too. The full 2nd floor is a beautifully designed executive 3-bedroom apartment that blends modern luxury with everyday comfort. This spacious residence features an open-concept living, dining & kitchen area enhanced by many windows that fill the space with natural light. High-end finishes, tiled & vinyl elegant flooring, and contemporary lighting create a warm yet sophisticated atmosphere. The gourmet kitchen is fully equipped with premium soft close cabinetry, sleek solid surface countertops, and state-of-the-art appliances — perfect for both casual meals and entertaining guests. Each of the three bedrooms is generously sized, offering ample closet space. The master suite includes a private en-suite bathroom with stylish fixtures and a walk-in closet, providing a peaceful retreat after a long day. The additional bedrooms are ideal for family & guests. Modern bathrooms, in-unit laundry, and plenty of parking with attached 2 car garage, elevate the convenience and comfort of this property. Owner can walk to shopping and eateries with mins to Route 12 & I91. Property can be sold completely furnished or not, all wiring is underground, property has Multi zone heating and cooling.

60 Dearborn Cir, Walpole

Listing courtesy of Cynthia M Westover from Galloway Real Estate LLC. ()

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board logo Copyright 2026 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, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .