Cheshire County, NH Homes between $1,500,000 and $2,000,000 for Sale

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Newest Cheshire County, NH Homes between $1,500,000 and $2,000,000 for Sale

$1,750,000

3 Beds ⋅ 3 Baths ⋅ 5102088 MLS

Tucked away on a private cove along the shores of beautiful Island Pond, this multi-level waterfront four-season home offers an exceptional opportunity to enjoy one of the Monadnock Region's most peaceful lakes. With a private dock, lakeside deck, fire pit, and remarkable glacial erratics, the property is designed for making memories in every season. Warm wood interiors and expansive windows capture the changing light and beautiful sunsets over the pond, while the open-concept living and dining area provides an inviting space for gathering with family and friends. The renovated kitchen and the fireplaced living room create a welcoming setting after a day on the water. The thoughtfully designed floor plan spans three levels, featuring three bedrooms, three baths, a dedicated office, and a spacious recreation room, offering flexibility for guests, remote work, or extended family. The attached two-car garage provides plenty of storage for vehicles, watercraft, and outdoor equipment. Offered mostly furnished, including the dock, this home is ready to enjoy from day one. Spend your days boating, kayaking, fishing, or swimming from your private waterfront, then explore Island Pond's undeveloped islands or gather around the lakeside fire pit beneath the stars. Whether you are searching for a year-round residence or a private retreat, this distinctive waterfront property is an ideal setting for lake living, entertaining, and creating lasting memories.

431 Treelyn Rd, Stoddard

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

$1,700,000

4 Beds ⋅ 3 Baths ⋅ 5099380 MLS

Strawberry Farm is an estate like no other in the area. The property features 165 unspoiled acres behind the house on the north side of RT 123 and across the roads another 8.5 acres that lead down to the shore of Lake Warren. The main house originally built in 1800 and re-designed by William Hartley Dennett in 1910 features his signature windows and a unique front entry. The open plan living area has doors onto the long veranda with exquisite views of the property behind the house and an adjoining greenhouse complete with koi pond. The farm style kitchen has a wood stove and rich handmade cabinetry. There is a ground floor bedroom with half bath. Upstairs offers endless possibilities with bedrooms with adjoining small rooms and a variety of spaces that could be more bedrooms or offices or workrooms. There is a covered porch above the veranda that could be the greatest screened in sleeping porch ever seen. The house needs updating but is rich with history and atmosphere. The grounds and outbuildings are impeccably maintained. The gardens are established with specimen plantings, pathways and landscaping elements that will stop you in your tracks. Behind the barn is a hedge wall carved to look like a wave and there are stands of trees worthy of a photo in the most discerning coffee table book. On the parcel with the lake frontage there is a rustic cabin, and a dock – perfect for summer residency and visitors. The back acreage has a pond and road access on the South side of the property. Whether your goal is to run a small farm or use the big barn for events, Strawberry farm is a rare opportunity. Schedule plenty of time for your visit and wear suitable shoes; the grounds are extensive. The Lake cabin is currently occupied but will be vacant by closing.

867 Forest Rd, Alstead

Listing courtesy of Vicki Gohl from Galloway Real Estate LLC. ()

$2,000,000

73543849 MLS

34,212 Sq. Ft. Industrial Building For Sale!

52 Fitzgerald Dr, Jaffrey

Listing courtesy of Listing Agent: Bret O'Brien from Listing Office: Greater Boston Commercial Properties, Inc..

$1,550,000

5 Beds ⋅ 5 Baths ⋅ 5086270 MLS

Set atop a majestic, private setting with sweeping views—including a stunning balcony vista of Mt. Monadnock—this exceptional 5-bedroom home in Swanzey offers the perfect blend of elegance, comfort, and quality craftsmanship. Designed for both everyday living and entertaining, the home features multiple inviting gathering spaces, from the sun-drenched sunroom to the beautifully appointed living and family rooms. A gracious morning staircase adds charm and functionality, while the first-floor office with custom built-ins provides an ideal work-from-home retreat. The expansive kitchen impresses with generous workspace, abundant cabinetry, and seamless flow into the surrounding living areas. Thoughtful architectural details, warm wood finishes, and high-end construction are evident throughout. Large island, wine fridge. Enjoy extensive hardscaping, including a spacious patio perfect for outdoor dining, relaxing, and taking in the serene landscape. Gazebo with hot tub, multiple outbuildings for projects and landscaping storage. The property continues to impress with an additional detached 3-bay garage and beautifully maintained grounds that enhance the home’s sense of privacy and scale. A rare offering combining refined living, breathtaking views, and timeless quality—this is New Hampshire living at its finest. Additional 7.5 acre building lot abutting included for $1,650,000.

101 Highland Cir, Swanzey

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

$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. ()

$1,600,000

3 Beds ⋅ 2 Baths ⋅ 5069723 MLS

SHOOTING STAR FARM is a private, fully equipped horse facility on 57± acres of open turnout and protective woodland. Purpose-built for breeding and training, it offers turnkey infrastructure and serenity for serious equestrian pursuits—without sacrificing the creature comforts of home. The 1984 chalet-style house is sited for pasture and pond views, with a sunlit chef’s kitchen overlooking the red barn’s activity. The main floor also includes an open, spacious living area w/access to a 3-season porch and deck, for warm-weather relaxation; 2 Bedrooms, and a full bath complete this level. Upstairs, find a restful primary BR with a luxurious custom bath. The walk-out lower level features 4 rooms, laundry, a wood stove, and a 2-car garage. The home's interior is being repainted now. For the horses, the c.2000 breeding barn has 12 stalls, wash stall, and a heated feed/lab/tack room, and a separate well. The centerpiece of the farm is a like-new facility with 14 stalls, indoor arena, a lovely galley kitchen, a ¾ bath with laundry, and a big office/meeting upstairs, both levels with mini splits for heat & AC. Additional amenities include a stunning granite patio w/firepit, large outdoor arena, multiple paddocks, hay storage, equipment lean-tos, and ample trailer/staff/guest parking. Off-farm riding includes miles of dirt roads and access to nearby 13,000-acre Pisgah State Park w/62 miles of trails. Shooting Star is more than a farm, t’s a lifestyle investment for those who value privacy, purpose, and the quiet satisfaction of working with horses in a setting that inspires. Just 15 mins. from Keene, NH for shopping, dining, and all services. Close to I-91, too.

484 Old Swanzey Rd, Chesterfield

Listing courtesy of Shirley Sullivan from Farms & Barns Real Estate LLC. ()

$1,995,000

6 Beds ⋅ 6 Baths ⋅ 5067451 MLS

***SUBSTANTIAL PRICE IMPROVEMENT! Never before lived in, this extraordinary Connecticut River estate offers a rare opportunity to own 18± private acres and 1,200± feet of pristine river frontage, complete with a sandy beach and breathtaking views. One of the last remaining undivided waterfront parcels of its kind, this newly constructed 6,400± sq ft residence blends luxury, privacy, and natural beauty in an irreplaceable setting. Designed for both everyday living and exceptional entertaining, the home features 6 bedrooms, 6.5 baths, and an accessory dwelling unit with a private entrance—ideal for multigenerational living, guests, or extended stays. Thoughtful craftsmanship is evident throughout, including 3/4” oak flooring, Marvin windows, porcelain-tiled baths, and custom cabinetry. Whether launching a boat from your shoreline, enjoying sunsets over the river, or hosting family and friends in a truly remarkable setting, this property delivers an unparalleled lifestyle rarely found in New England. A one-of-a-kind waterfront estate offering a legacy property for generations to come. A seller credit will be provided at closing for kitchen, bathroom, and closet accoutrements, offering the opportunity to personalize the finishing touches to suit your own taste and style. Competitive seller financing options available. Just 5 minutes from Brattleboro and I-91 and only 15 minutes from Keene.

30 Farr Rd, Chesterfield

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

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