Cheshire County, NH Multi-Family Homes for Sale

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Newest Cheshire County, NH Multi-Family Homes for Sale

$975,000

5116626 MLS

COMING SOON! Completely remodeled West Keene Cape-style home featuring a wonderful, spacious ADU (Accessory Dwelling Unit) and set on an impressive 2.9-acre lot! A rare opportunity offering beautifully updated living space, versatility, and plenty of room to enjoy. Perfect for multi-generational living, guests, or additional income potential. More details and photos coming soon!

90 & 90a Bradford Road, Keene

Listing courtesy of Paul Rodenhauser from BHG Masiello Keene. ()

$379,000

5116342 MLS

Welcome to 25 Woodburn Street! This well-maintained two-family property is conveniently located just a short walk from downtown Keene, offering a great opportunity for investors or owner-occupants alike. The first-floor unit features two bedrooms, a spacious kitchen, living room, and laundry in the basement. Upstairs, you'll find a larger three-bedroom unit featuring a primary bedroom with its own private bathroom and laundry, a comfortable living room, and a kitchen with a walk-in pantry. Both units have their own covered porches, while the backyard offers a great outdoor space. A detached two-car garage and additional off-street parking add even more convenience. Whether you're looking to expand your investment portfolio or live in one unit while renting out the other, this property offers plenty of possibilities in a desirable Keene location!

25 Woodburn St, Keene

Listing courtesy of Shane M Moynihan from Realty One Group Next Level. ()

$699,000

5115957 MLS

Welcome to 37 Michigan Street, a meticulously cared-for, turnkey four-unit multi-family property offering incredible versatility, robust cash flow, and complete flexibility. The unit mix features a spacious four-bedroom open-concept layout that is ideal for an owner-occupant or high-yield rental income, complemented by one two-bedroom apartment and two one-bedroom apartments for a total of eight bedrooms across the entire building. High-quality infrastructure provides rare peace of mind, highlighted by a dependable Buderus furnace, durable metal roof, separate electric meters for each apartment, a coin-op laundry room, and a sprawling, private back yard. Situated on 8.9 wooded acres, the property boasts valuable standing timber and unlimited potential for future expansion or development with town approval. Nestled in charming Winchester, owners and tenants enjoy a vibrant Monadnock Region lifestyle with local craft tasting rooms, historic covered bridges, and peaceful paddling on the Ashuelot River. Outdoor enthusiasts will appreciate being just minutes from the 13,300-acre Pisgah State Park for hiking, mountain biking, and trail exploration, all while commuting with quick drives to Keene, Massachusetts, and Vermont. Whether you choose to house-hack by living virtually rent-free in the flagship four-bedroom home or expand your investment portfolio with an income-generating property, this presents a rare blend of charm, turnkey quality, and immediate upside.

37 Michigan St, Winchester

Listing courtesy of Bob Barnard from Monadnock Realty Group LLC. ()

$385,000

5115905 MLS

Tucked behind the historic Frost Free Library, dating to 1866, is this charming 1876 New England home filled with character and potential. Currently configured as a three-family property, it offers flexibility for an investor, owner-occupant, or buyer looking to create a unique single-family home. The main living space spans two floors, with bedrooms and a bathroom upstairs. The original breezeway to the barn has been converted into a second unit. Renovations were started, leaving the space partially open to the studs and ready for the next owner to bring their vision to life. The third unit is located downstairs and has its own driveway. Each unit has a separate entrance, parking, and electric meter. 2020 main building was re-roofed. A true highlight is the 36' x 36' post-and-beam barn, featuring two floors and a basement, offering plenty of possibilities for storage, workspace, studio space, or more. With its historic charm, versatile layout, impressive barn, and potential for a single-family conversion, this property is truly one-of-a-kind. Come see the possibilities for yourself!

17 Pleasant St, Marlborough

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

$250,000

3 Beds ⋅ 3 Baths ⋅ 73590192 MLS

Welcome to 24 Park Drive in the highly desirable Monadnock Tenants Co-Op Rindge NH! This well-maintained home offers three bedrooms and three bathrooms, along with a cook’s dream kitchen and an inviting open concept design perfect for everyday living and entertaining. Enjoy the convenience of central air conditioning, whole house generator hook up, a one car garage, and additional storage in the over sized shed. Ideally located in a great commuter location and just minutes from shopping, dining, and so much more, this home offers both comfort and convenience. With a low monthly park fee of just $225, this is an exceptional opportunity to enjoy easy living in one of the area’s most desirable communities!

24 Park Drive, Rindge

Listing courtesy of Listing Agent: Amy Reisert from Listing Office: Borderline Realty.

$589,000

5114050 MLS

INCENTIVE ALERT: Seller offering a $15,000 credit at closing to fund a buyer interest rate buy-down! Slash your monthly payment by nearly $600/mo in Year 1 on this brand-new build. Brand New Townhouse duplex! Turn-key, side-by-side design featuring mirror-image 3-bedroom, 1.5-bathroom units. Ideal for a traditional investor seeking immediate cash flow or an owner-occupant looking to sharply cut their living costs. • Premium Rental Potential: Estimated market rent of $2,400–$2,500 per side ($4,800–$5,000 total gross monthly income). • Massive Overhead Savings: Fully separate electric, gas, and water meters already installed for each unit to keep landlord expenses minimal. • Zero Deferred Maintenance: Brand-new systems, roofs, and appliances mean no expensive capital repairs for years to come. • The Layouts: Bright, modern, open concepts, stunning kitchens, durable LVP floors and massive full basements. Investors: Set your own market rents on Day 1 with a completely empty, zero-headache asset. House-Hackers: Live in one side and let the second unit cut your monthly housing payment in half while you build equity in a brand-new building. High-quality new multifamily construction is a rarity for this area. Schedule your private tour today!

49 Keene Rd, Winchester

Listing courtesy of Emily Lagerberg from R.H. Thackston & Company. ()

$330,000

5113963 MLS

Two unit multi-family in Downtown Keene. Located across the road from the entrance to Keene State College, this property has been a reliable income producer in high demand. Four bedroom 2 story house with attached studio apartment. Both units connect and can be used as a large 5 bedroom rental or 2 separate tenancies. Currently rented to a group of 5 KSC Students until May 31, 2027. Rental roll is $39,600 annually. Owner pays utilities, but both units have own utilities. At least 48 hours notice required for showings. Good sized backyard with partial fence and deck. Vinyl windows, roof is less than 10 years old, clapboard sided, hard wired smoke detectors and full basement. Owners are licensed NH Real Estate Brokers.

11 Elliot St, Keene

Listing courtesy of Joshua Greenwald from Greenwald Realty Group. ()

$399,900

5113927 MLS

Here’s a well-positioned multi-family opportunity in the heart of Keene. 120 Elm Street offers three residential units across 2,142 square feet, with projected gross rents of $4,945 per month ($59,340 per year) and an impressive 11% cap rate. The two 2-bedroom units are currently leased at $1,100 and $1,645 per month. The spacious first-floor 3-bedroom unit is vacant and projected to rent at $2,200 per month, so a new owner can choose their own tenant or move in and live in one unit while the other two help cover the mortgage. The gap between the two 2-bedroom rents also suggests room to raise rent over time. A brand-new heating system serves all three units, giving you peace of mind and lower near-term capital costs. Each unit has its own electric meter, so tenants pay their own electricity. A shared first-floor laundry area and off-street parking add convenience for residents and lasting value for the owner. Keene’s steady rental demand, supported by local colleges, healthcare, and a lively downtown, makes this property a strong long-term hold. Contact us today for full financials and to schedule a private showing.

120 Elm St, Keene

Listing courtesy of Kristi Whitten from Keller Williams Realty-Metropolitan. ()

$375,000

5113478 MLS

A unique opportunity to own a well-maintained and thoughtfully updated 2-unit property on a quiet dead-end street in a convenient Keene location. Set among just a handful of homes, this property offers a welcoming residential setting while remaining just a short distance from downtown shops, dining, and local amenities. The first-floor two-bedroom unit features its own dedicated washer and dryer along with efficient oil heat that has been recently serviced. Upstairs, the spacious three-plus-bedroom unit offers propane heat, a newly installed dishwasher, and brand-new dedicated laundry. Mature trees provide a natural buffer along the side of the property, while established perennial plantings add seasonal color around the front and sides of the home. The backyard provides open space with room for gardening or creating an inviting outdoor area. A generous driveway accommodates up to four vehicles, and each unit has its own laundry for added convenience. Tenants pay their primary utilities, with the landlord currently responsible for water, sewer, and snowplowing. There is also a large storage space onsite that is currently shared. Whether you're looking for an investment property or an owner-occupied duplex with additional rental income, this well-positioned property offers flexibility, thoughtful updates, and the comfort of a residential setting close to all that downtown Keene has to offer. Showings available on Wednesdays and Saturdays by appointment.

8 Mystic Pl, Keene

Listing courtesy of Rochelle Gaouette from Greenwald Realty Group. ()

$450,000

5112878 MLS

Great Investment Opportunity in Keene! This versatile property offers an excellent combination of rental income, storage, and future development potential, all situated on 1.3 acres of level, cleared land in a desirable Keene location. The property features a two-family residence with a spacious 4–5 bedroom home plus an additional 1-bedroom apartment, providing valuable rental income or flexible living arrangements. A large commercial-style garage offers plenty of room for storage, a workshop, vehicles, or other uses. Adding even more potential, there is the possibility of constructing an ADU or additional residence, creating an opportunity for a buyer to build their own home while using the existing two-family property as an income-producing asset to help offset the cost. Conveniently located within walking distance of the clinic and hospital, downtown Keene, shopping, restaurants, and a network of biking and hiking paths. A rare opportunity to own a property with income potential, substantial land, and exciting possibilities for future development. Bring your ideas and make the most of this exceptional Keene property!

470 Elm St, Keene

Listing courtesy of Nancy Proctor from BHG Masiello Keene. ()

$499,000

5111561 MLS

Welcome to 31 Valley Street, a distinctive two-family residence situated in a desirable Keene neighborhood. Thoughtfully renovated by a nationally recognized designer/builder with quality craftsmanship and an attention to detail. The two-family configuration offers excellent flexibility, whether used as an investment property, owner-occupied residence with rental income, or a multi-generational living arrangement. Also can easily be converted to a one family or, create a studio/loft in barn for a 3rd unit. Improvements include new standing seam roof, new electric, plumbing and sewer line, new boiler, windows, cabinets and all new kitchen appliances.

31 Valley St, Keene

Listing courtesy of Vincent Dolan from RE/MAX Town & Country. ()

$340,000

5111251 MLS

Looking to add to your investment portfolio or find a home with room for multiple generations? This updated two-family property offers an excellent opportunity with two separate units, all set on 9 acres and tucked back from the road for added privacy. Unit 1 features two bedrooms and has seen several recent updates, including new windows and hardwood flooring in the sunroom, new appliances, and fresh paint throughout. Unit 2 offers two bedrooms and has been refreshed with new butcher-block-style countertops, updated electrical, and a fully remodeled bathroom. Both units are also equipped with brand new mini-splits for efficient heating and cooling. Outside, enjoy the space and privacy this property has to offer, with plenty of room to relax, explore, or simply enjoy the peaceful surroundings from the rear deck. For those who enjoy the outdoors, Sportsman Pond is just a short walk across the street. Whether you're an investor, a first-time buyer looking to offset your mortgage with rental income, or searching for a flexible multigenerational living arrangement, this property offers plenty of possibilities. Schedule your private showing today!

612 Royalston Rd, Fitzwilliam

Listing courtesy of Samantha Vaillancourt from Keller Williams Realty-Metropolitan. ()

$425,000

5110811 MLS

Large two family home!!! In town location. Close to schools, shopping and amenities. Many original features; staircase and lovely banister in entrance hall, moldings, fireplace surround as well as turret and alcove windows. Large units; one 2 bedroom and one 3 bedroom. All separate utilities. Well maintained property ready for you to take ownership!

42 Parker St, Winchester

Listing courtesy of Dick Thackston from R.H. Thackston & Company. ()

$399,000

5110272 MLS

Classic brick Colonial overlooking the Fitzwilliam Town Common, offering historic character, generous living space, and remarkable flexibility. Originally built as a single-family home, the property was divided down the middle to create a two-family residence, with each side offering two bedrooms and two baths. Separate utilities make the current configuration particularly convenient for an owner-occupant seeking rental income, extended-family living, or an investment property. The home's original character remains evident throughout, including beautiful wood floors, original built-ins, multiple fireplaces, large rooms, and bright front rooms with impressive windows overlooking the village green. Each side has a first-floor half bath, spacious living areas, and its own front and back staircase. One side features an eat-in kitchen and a large bathroom/laundry combination with a soaking tub. There is plenty of storage throughout, along with a large mudroom, screened porch, and attached two-car garage. The town lot provides room for gardening, outdoor space, and plenty of parking. Above it all, the large attic offers an abundance of additional storage and the potential for future finished space. The property could continue as a two-family home, providing the opportunity for rental income, or could be returned to its original single-family configuration. With some updating, this handsome brick Colonial could be brought back to its former charm while retaining the character and architectural details that make older New England homes so appealing. Located right in the heart of Fitzwilliam's quintessential New England village center, this is an opportunity to own a substantial historic home in a truly distinctive setting.

56 Nh Rt 119 W, Fitzwilliam

Listing courtesy of Michael Breshears from BHG Masiello Peterborough. ()

$344,000

5109369 MLS

If you want a GREAT LOCATION to Keene State College for an Investment property.. look no further! Whether you’re looking to start building your investment portfolio or add a solid, income-producing property in the heart of downtown Keene, this well-located two-family New Englander checks all the boxes. Each unit offers 2 bedrooms and 1 full bath, with hardwood floors throughout and basement laundry hookups. The first-floor unit features an updated kitchen and bath, a comfortable living room, and two bedrooms. The second-floor unit includes two bedrooms, a living room, a spacious kitchen, and an updated bath. Investors will appreciate the separate electric and hot water heaters, vinyl windows and siding for low maintenance, and a durable slate roof. One shared heating system services both units. Each unit comes fully applianced. Exterior amenities include off-street parking for six or more vehicles, a two-car garage ideal for storage, and an enclosed side porch adding additional usable space. A prime location, strong rental appeal, and solid fundamentals make this a smart addition to any portfolio. Appointment 24 required—start building your future today.

35 Elliot St, Keene

Listing courtesy of Robin Smith from BHG Masiello Keene. ()

$330,000

5106207 MLS

Well maintained and fully occupied Multi-family near Downtown Keene. Each unit is 3 bedrooms with good sized living rooms and each has own enclosed porch. Vinyl sided, replaced heating system, vinyl windows. Owners are licensed NH Real Estate Brokers. No showings on Sundays.

81 Water St, Keene

Listing courtesy of Joshua Greenwald from Greenwald Realty Group. ()

$2,779,000

5104867 MLS

Exceptional Turnkey Investment Opportunity! Welcome to 2A–H Valley Creek Lane in Swanzey, NH, an outstanding 8-unit townhouse condominium community offering immediate income and exceptional long-term investment potential. Seven of the eight units are currently leased, providing instant cash flow with one remaining unit available to lease or occupy. This well-designed community features an ideal unit mix consisting of four spacious 2-bedroom, 1.5-bath townhomes, each offering approximately 1,040 square feet, and four generous 3-bedroom, 2.5-bath townhomes with approximately 1,336 square feet of living space. Every unit showcases an open-concept layout with modern finishes, stylish kitchens featuring stainless steel appliances and center islands, energy-efficient mini-split heating and cooling systems, in-unit laundry, private patios, and full basements providing ample storage. Located just minutes from downtown Keene, shopping, dining, schools, recreational opportunities, and major commuter routes, this low-maintenance property offers the perfect balance of convenience, quality, and strong tenant appeal. The townhouse-style design provides residents with the comfort and privacy they desire while offering investors an attractive, easy-to-manage asset. Whether you're expanding your real estate portfolio, completing a 1031 exchange, or seeking a high-performing multifamily investment, this property presents a rare opportunity.

2 A-H Valley Creek Ln, Swanzey

Listing courtesy of Pat Paquette from BHG Masiello Keene. ()

$555,000

5104779 MLS

Exceptional 4-unit multi-family property situated a short stroll from vibrant downtown Keene. Steeped in 19th-century character, this property perfectly blends timeless historic details with reliable income generation. Investment Highlights Consistent Cash Flow: Outstanding, proven rental history supported by reliable, long-term tenants who wish to stay. Unbeatable Location: Easy walking distance to Main Street’s shops, dining, local events, and nearby parks. Historic Charm: Retains classic 1800s architectural elements, original trim work, and unique period details that provide immense character.

61 Winter St, Keene

Listing courtesy of Doreen R Soares from RE/MAX Realty One. (Cell: 603-393-7871)

$300,000

5102904 MLS

At the end of a quiet street bordering on conservation land, find this well maintained two-family home. Partially fenced yard and a one car garage. Two units, each with one bedroom and one bath. Most of the rooms have been freshly painted. Hardwood flooring throughout. Oil heat in Unit #1 and electric baseboard in Unit #2. Separate meters for hot water and electric. Public water and sewer. A great opportunity to own a two-family home in a great Keene location. Unit 1 is unoccupied. Unit 2 is occupied.

40 Wilford St, Keene

Listing courtesy of Susan Love from Duston Leddy Real Estate. (Cell: 908-656-2028)

$475,000

5093431 MLS

ATTENTION INVESTORS! Through no fault of the Seller, this property is back on the market. The next Buyer will benefit from the July general and septic inspections. The bank ordered appraisal in excess of asking price is also available for review. 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. 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)

$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. 4 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. ()

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Cheshire County, NH Multi-Family Homes for Sale

Newest Cheshire County, NH Multi-Family Homes for Sale

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