Cheshire County, NH Real Estate Search

Cheshire County, NH Just Listed Homes for Sale

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Newest Cheshire County, NH Just Listed Homes for Sale

83 Timberlane Dr, Keene
$429,000
3 Beds ⋅ 3 Baths ⋅ 5117407 MLS
Located in a sought after neighborhood surrounded by conservation land, this 3 bedroom, 2.5 bath home offers a wonderful combination of convenience, natural surroundings, and community amenities. The bright interior features hardwood floors, a modern kitchen, and a separate dining area with it's own door to the backyard. A first floor mini-split provides cool relief for the warmer months. The open concept design lends itself to comfortable gatherings, and the first floor laundry, direct entry from the attached garage and a half bath add to the home's everyday appeal. Upstairs you'll find a spacious and bright primary suite, complete with 3 closets! Two additional bedrooms and a full 2 vanity bathroom complete the second floor. The finished lower level offers additional living space which includes a propane stove to round out the perfect area for relaxing to read uninterrupted or entertaining to watch the big game. Enter the outdoors through walk out French doors to the side yard, with hiking and biking trails practically at your doorstep. Neighborhood amenities include a community swimming pool and clubhouse. All this in a peaceful setting just 5–10 minutes from downtown Keene, Dartmouth-Hitchcock Medical Center, schools, parks, and two theaters, with easy access to Routes 9 and I-91. Boston is approximately 1 hour and 45 minutes away. Open House Saturday, November 14th, 10 AM–12 PM.

83 Timberlane Dr, Keene

Listing courtesy of Christine Houston from Greenwald Realty Group. ()

2 Cardinal Cir, Keene
$70,000
2 Beds ⋅ 1 Baths ⋅ 5117346 MLS
Set on a desirable corner lot in the well-maintained Tanglewood Park Co-op, this 2-bedroom manufactured home offers a chance to make it your own with many major upgrades already completed. The owner replaced the roof, flooring, and all appliances, updated the breaker box and electrical, and added a new water heater and oil tank. The bathroom was fully renovated in 2020. The plumbing was replaced and relocated inside the home to help prevent winter freeze-ups. The kitchen has been updated with new appliances, and the remaining countertop section will convey with the sale for the buyer to install. New flooring has been installed throughout the home except in the primary bedroom. Outside, a new shed provides an additional 288 sq. ft. of storage space (ample space for tools, outdoor gear, or hobbies). The permanent dog fence conveys and is grandfathered in. One of Tanglewood Park Co-op’s standout lots, this spacious corner lot offers plenty of outdoor space, two storage sheds, and expanded parking that accommodates up to six vehicles. There’s plenty of room for family and friends to park when they visit. With many of the major updates already in place, there’s a solid starting point for a buyer ready to tackle the remaining repairs and add their finishing touches. Located just minutes from Keene’s hospital, shopping, and major highways. Cash buyers only. Co-op approval is required, including credit and background checks. Book your showing today!

2 Cardinal Cir, Keene

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

64 Kendall Rd, Keene
$499,900
3 Beds ⋅ 2 Baths ⋅ 5117205 MLS
The Best of Single-Level Living! Welcome home to this exceptionally well-maintained 3-bedroom, 2-bath ranch, offering the perfect blend of comfort, convenience, and generous living space. Thoughtfully cared for and ready for its next owners, this inviting home features attractive crown molding, a spacious living room, and a generous dining area, creating a welcoming setting for everyday living and entertaining. The kitchen offers stainless steel appliances, granite countertops, and abundant cabinetry and workspace. A convenient direct entrance to the garage makes bringing in groceries and everyday essentials a breeze. The spacious primary bedroom, accessed through elegant French doors, offers direct access to the deck and patio, creating a wonderful connection to the outdoors. All three bedrooms provide ample closet space. Additional features include a two-car garage with a convenient interior entrance to the basement, central air conditioning, and a whole-house propane generator to provide added comfort and peace of mind during storm-related power outages. Need extra room? You'll appreciate the expansive 26' x 41' basement, along with two additional crawl spaces offering excellent storage and workspace possibilities. Situated on a desirable corner lot, the property also features a fenced backyard, ideal for outdoor enjoyment, entertaining, gardening, or simply relaxing. AND THERE'S MORE! The seller is including a home warranty through America's Preferred Home Warranty, offering additional peace of mind with coverage options for major home systems and appliances, including electrical, plumbing, and HVAC. If you've been searching for the ease of single-level living without sacrificing space, storage, or convenience, this lovingly maintained home deserves a place at the top of your list. Come see all it has to offer!

64 Kendall Rd, Keene

Listing courtesy of Gerry Leo from BHG Masiello Keene. ()

499 Watkins Hill Rd, Walpole
$399,000
3 Beds ⋅ 2 Baths ⋅ 5117171 MLS
Welcome to The Brook House, where cozy cottage charm meets peaceful New England country living! Set on .75 beautifully landscaped acre with scenic conservation land and pastoral views nearby, this inviting Cape feels tucked away, yet is just 10 minutes from Keene and I-91. Inside, a cozy, comfortable cottage-like interior is filled with character. Real wood doors, vertical shiplap, warm wood floors and vintage details create a welcoming feel throughout. The living room invites you to settle in beside the brick fireplace with its vintage tile, wide-plank pine floors, built-in shelving and window seat overlooking the pond. A charming dining room and bright kitchen offer inviting spaces to gather. The main-floor primary bedroom provides convenience, with two additional bedrooms and a 3/4 bath upstairs. The full basement includes laundry and storage space. Outside, the magic continues! Listen to spring peepers by the pond, catch frogs in summer, cool off in the brook and skate when winter conditions allow. The brick patio is perfect for summer BBQs and evenings around the fire pit. Enjoyed as a small farmette, the property has welcomed chickens, goats, sheep and even an occasional summer cow! Six raised garden beds, a greenhouse, apple and peach trees, berries, Concord grapes and maples for collecting sap add homesteading charm. Mature trees, perennial gardens, neighboring conservation land and scenic pastures create a peaceful backdrop. Access to a snowmobile trail adds year-round adventure. Brook House has been a wonderful place to call home, filled with memories made in every season. The sellers look forward to seeing its next chapter unfold and this special property loved for years to come. Showings begin with Open House on Sunday, November 8 from 2-4 p.m. Seller is a licensed NH real estate agent.

499 Watkins Hill Rd, Walpole

Listing courtesy of Kimberly Anderson from Keller Williams Realty Metro-Keene. ()

65 Nelson Rd, Harrisville
$535,000
2 Beds ⋅ 2 Baths ⋅ 5117063 MLS
Looking for a home with beautiful water views and plenty of New England charm? This bungalow is located directly across the street from 138-acre Harrisville Pond, offering wonderful views without the higher taxes that often come with direct waterfront ownership. Whether you are looking for a year-round home or a weekend escape, this property is the perfect spot for birdwatching and stargazing. The outside also offers plenty to enjoy, with established perennials, a vegetable garden, and a fire pit. Inside, the remodeled kitchen is a real highlight, featuring a farmhouse sink, beautiful stone countertops, soft-close cabinets, pantry storage, stainless steel appliances, and a gas range. The living room feels bright and open with cathedral ceilings, skylights, hardwood floors, a propane fireplace, and sliders leading outside. The primary bedroom has blackout shades and opens to a paneled, insulated porch where you can enjoy the views in every season. Other updates include fresh interior paint, cedar shingles, gutters, a crushed-stone driveway, a newer washer and dryer, and a water filtration system. You'll also appreciate the practical extras, including a compost enclosure, clothesline, and partial fencing. The lower level offers a guest room, half bath, utility room, and one-car garage with an automatic opener and workbench area. The home also features solid 2x6 construction for added insulation. Located near Harrisville's historic red-brick mills and charming village center, this is a great opportunity to enjoy small-town living, beautiful pond views, and one of Cheshire County's lowest-tax towns. Why wait until spring? Make this home yours now and be ready to enjoy everything it has to offer. Next summer, you could be out paddling on the pond, taking a swim, or relaxing in the sand at Sunset Beach!

65 Nelson Rd, Harrisville

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

36 Fitzwilliam Rd, Troy
$319,900
3 Beds ⋅ 1 Baths ⋅ 5117007 MLS
Completely renovated and move-in ready, this bright three-bedroom ranch offers more than 1,300 square feet of comfortable living, all on one level. A covered front entry welcomes you into a sprawling living room, with a broad bank of windows and room for a generous seating arrangement, reading nook or both. Fresh paint, new recessed lighting and brand-new vinyl plank flooring create a clean, inviting feel throughout the main living spaces. The adjoining dining area offers plenty of room to gather around the table, whether for a quiet morning coffee or dinner with friends. The eat-in kitchen features warm wood cabinetry, generous counter space and an easy connection to the dining room for everyday meals and entertaining. A brand-new refrigerator, range and microwave complete the kitchen. Three spacious bedrooms feature brand-new carpet and ceiling fans, with flexibility for guests, hobbies or a home office. An updated full bath and a separate laundry room with washer and dryer keep daily essentials easy. The laundry room's exterior entrance makes coming in from the yard or attached open-sided carport especially convenient. Outside, the manageable 0.18-acre lot offers space for a garden, outdoor seating or simply enjoying the lawn, while the carport provides covered parking. Additional highlights include a two-year-old metal roof, newer vinyl windows, a one-year-old electric water heater and a two-year-old oil furnace, recently serviced ahead of winter. Public water and sewer add everyday practicality. Enjoy a fantastic Troy location with churches, the library, community center, stores, schools and post office close by, plus easy access to Keene and the Monadnock region. This turnkey home brings comfort, convenience and easy one-level living together. Schedule your showing today!

36 Fitzwilliam Rd, Troy

Listing courtesy of Steve Petz from Realty One Group Next Level. ()

441 Rte 63, Westmoreland
$519,900
3 Beds ⋅ 2 Baths ⋅ 5116998 MLS
Nestled in the desirable town of Westmoreland, NH, this beautifully maintained 3-bedroom, 2-bath Cape offers a wonderful blend of classic New England charm, quality craftsmanship, and thoughtful modern updates. At the heart of the home is a custom kitchen crafted by renowned local cabinetmaker Terry Cox of Cox Woodworking, featuring beautiful cabinetry, a Sub-Zero refrigerator, and JennAir cooking appliances. Warm hardwood floors, an inviting living area with exposed brick accents, and a welcoming dining space create an effortless flow for everyday living and entertaining. Just beyond, a beautiful window-lined porch offers peaceful views of the surrounding woods. Currently used as a home office, this inviting space provides a wonderful setting to work, unwind, or simply enjoy the changing New England seasons. Thoughtfully cared for over the years, the home features an updated second-floor bathroom, a roof replaced approximately three years ago, and a new tankless boiler installed just one year ago. An attached two-car garage adds everyday convenience, while the surrounding grounds provide a picturesque backdrop for enjoying the natural beauty of country living. Ideally situated in sought-after Westmoreland, with convenient access to Keene, NH, Brattleboro, VT, and the surrounding Connecticut River Valley, this inviting property offers the charm and character of a traditional New England home with the comfort and convenience of meaningful modern improvements. A wonderful opportunity to enjoy country living without sacrificing accessibility. ***Open House 11/8 from 11-1***

441 Rte 63, Westmoreland

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

43 Christian Hl, Swanzey
$335,000
3 Beds ⋅ 2 Baths ⋅ 5116863 MLS
Discover the charm of New England living at 43 Christian Hill Road! Set in a quiet location on a .68-acre level lot, this versatile property offers convenient one-level living, beautiful wood floors, original built-ins, and distinctive Bennington door knobs. A newer roof adds peace of mind, while the screened side porch is perfect for relaxing and enjoying the peaceful surroundings. A workshop room with wood stove insert provides space for hobbies and projects. Upstairs, the attic features blown-in insulation, excellent storage, and potential for additional finished space, subject to necessary approvals. Additional features include a drilled well, generator hook up, town sewer, and forced-air heating. An exceptional highlight is the additional separate living unit! Complete with its own independent heating, hot water, and electric, plus a washer and dryer for each living space, this property offers wonderful flexibility for extended family, multi-generational living, guests, or potential supplemental rental income. The additional unit features a propane wall heater and may also appeal to traveling nurses or other visiting professionals. Enjoy privacy and independence while keeping loved ones close! Enjoy all that southwestern New Hampshire and the Monadnock Region have to offer. Explore nearby Swanzey Lake, Wilson Pond, and the scenic Ashuelot River for swimming, boating, kayaking, and fishing. Enjoy nearby walking and biking trails, hike Mount Caesar, or discover Swanzey's historic covered bridges. Convenient to Keene for shopping, dining, healthcare, and everyday amenities. A wonderful combination of New England character, peaceful surroundings, one-level convenience, and exceptional versatility. Whether seeking room for family, potential additional income, or a special place to call home, 43 Christian Hill Road is full of possibilities!

43 Christian Hl, Swanzey

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

161 Concord Rd, Keene
$3,200,000
4 Beds ⋅ 4 Baths ⋅ 5116742 MLS
Discover a remarkable New England estate that offers a 12,370 sq ft structure with more than 7,000 square feet of finished living space tucked into 16 private acres, just minutes from downtown Keene. Beyond a long, curving looped driveway awaits a world of mountain views, natural beauty, and extraordinary possibilities, secluded yet remarkably convenient to shopping, dining, services, everyday amenities and close proximity to hospital and local airport. Explore manicured private trails for walking, reflection and outdoor recreation, winding past natural glacial rock formations, fruit trees, gardens, and wildflowers. Watch the seasons unfold across the mountains and valley, or gather around an impressive outdoor fire pit seating 16 or more. Rich mahogany woodwork lends warmth and character to an expansive, versatile layout with two full kitchens, five gas fireplaces, a wine cellar, and three conveniently located laundry rooms, one on each floor. Six flexible-use rooms invite you to imagine offices, studios, libraries, fitness areas, or guest spaces. Additional areas offer room for future plans and select areas offer an opportunity for personalized finishing touches, while an attached RV garage and two-car garage add practical flexibility. The home features 400-amp electrical service, offering capacity for workshops, creative pursuits, and future projects. Whether your vision is a multigenerational retreat, a private sanctuary, an entertainment destination, or a home designed for memorable gatherings, this estate offers a lifestyle as unique as your vision. Properties combining acreage, privacy, architectural scale, and proximity to a city are rare and difficult to replicate at $3.2 million.

161 Concord Rd, Keene

Listing courtesy of Jessie Carpenter from Keller Williams Realty Metro-Keene. ()

14 Shadow Ln, Keene
$375,000
3 Beds ⋅ 2 Baths ⋅ 5116627 MLS
LOCATION, LOCATION, LOCATION! Just move right into this IMMACULATE home w/2-car garage located in a highly desirable West Keene neighborhood and immediately enjoy the Quality of Life this property has to offer. LIGHT, BRIGHT, AND AIRY throughout, this home features recently refinished hardwood floors with most of the interior being freshly repainted a neutral and inviting color to complement your furnishings and décor. There are 3 bedrooms, a full bath, an eat in kitchen, and a large living room with a dining area on the upper level, while a spacious, finished bonus room on the lower level provides versatility to suit your family’s needs and lifestyle. The lower level also offers a finished laundry room and a half bath that may be able to be expanded to a second full bath. Other improvements include replacing the lower level carpeting with vinyl plank flooring, new exterior vinyl siding in 2023, a new sink, rangehood and light fixtures in 2026, and more! Relax, dine, or enjoy a barbeque with family and friends on the attached deck accessed off of the eat-in kitchen overlooking the side yard, or step outside and walk, run, or bike nearby rail trails, visit nearby parks, attend the YMCA, and fully appreciate all of the other amenities and activities Keene has to offer. A nice opportunity in a sweet neighborhood for you and your family to enjoy for years to come. Conveniently located near Symonds Elementary, Keene Middle and Keene High Schools. Showings by appointment only.

14 Shadow Ln, Keene

Listing courtesy of Deborah L Lucey from RE/MAX Town & Country. ()

23 White Brook Dr, Sullivan
$825,000
5 Beds ⋅ 3 Baths ⋅ 5116548 MLS
Unique 53-Acre Property in Sullivan, NH — Your Own Private Country Retreat! Discover an extraordinary opportunity to own 53 acres of beautiful New Hampshire countryside with multiple living spaces and endless possibilities! The 1970 post-and-beam contemporary features 3 bedrooms, 1½ baths, an open-concept living and dining area, sunroom, and full basement. Perched on a hill, the home enjoys fantastic views, while a pond and hiking trails through the woods invite you to explore and enjoy the natural beauty surrounding you. A second home and a 2-bedroom apartment over the garage provide wonderful options for rental income, guests, extended family, or a caretaker. With abundant open land for gardening, farming, and raising animals, this is an ideal setting for those dreaming of a self-sufficient lifestyle. Enjoy absolute privacy and the freedom of country living, yet remain just minutes from Keene's shopping, restaurants, and theater. Approximately 2 hours to Boston and 4 hours to NYC. Don't miss this rare opportunity to own your own piece of New Hampshire paradise! Whether you're looking for a private retreat, a multi-generational property, rental income, or the perfect place to live off the land, this remarkable property deserves your attention. Schedule your private showing today and imagine the possibilities! Open House Saturday, November 7th from 12:30- 2

23 White Brook Dr, Sullivan

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

582 Glebe Rd, Westmoreland
$625,000
3 Beds ⋅ 3 Baths ⋅ 5116374 MLS
Discover the beauty, privacy, and possibilities of this enchanting Westmoreland retreat. Tucked away from the main road on 22.5 scenic acres, the former High Hopes Apple Orchard offers a special piece of New England, complete with stone walls, established landscaping, a barn, sheds, and approximately 1,500 blueberry bushes and 500 apple trees. With work underway to restore the farm to regular production, this beloved property is ready for its next chapter—and your vision. Inside, warmth and character shine through custom cabinetry and hardwood and tile floors throughout. The spacious kitchen features a walk-in pantry and opens to the living room, where a woodstove hookup offers the potential for cozy winter evenings. A stunning dining room showcases vaulted ceilings, a Palladian window, and radiant heat. Equally inviting as a family room, this beautiful space provides a backdrop for gathering or simply watching the seasons unfold. A convenient laundry area with a half bath completes the main level. Upstairs, the sun-filled primary suite welcomes you with twin skylights, two generous closets, and an expansive private bath with double sinks and a walk-in shower. The lower level offers even more flexibility, with a large mudroom that could accommodate an office area, a bedroom, a three-quarter bath, and an additional room ideal for crafts, hobbies, or creative pursuits. Thoughtful features include five heating zones, a generator, separate electric service for the barn, and fiber-optic internet. Enjoy a secluded country setting with convenient access to schools, shopping, and ski areas. Whether you envision tending the orchard, exploring your acreage, or simply savoring the peace of country life, this magical property invites you to put down roots and make it your own.

582 Glebe Rd, Westmoreland

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

344 Court St, Keene
$390,000
4 Beds ⋅ 2 Baths ⋅ 5116280 MLS
Classic New England charm meets thoughtful modern updates in this spacious antique home, conveniently located on Court Street in Keene! Offering more room than meets the eye, this well-maintained 4-bedroom home blends timeless character with numerous improvements designed for today's lifestyle. The inviting living room provides a comfortable space to relax or entertain, while the kitchen boasts a full suite of newer KitchenAid appliances, including an induction range, along with refinished floors that continue into the dining room. Fresh paint, updated lighting, and a beautifully renovated bathroom are just a few of the many interior improvements. A standout feature is the newly renovated first-floor primary bedroom, complete with a mini-split for added comfort and an Andersen sliding glass door leading to a private deck with a hot tub overlooking the backyard for your own little retreat! First-floor laundry adds everyday convenience, while three additional bedrooms upstairs provide flexibility for guests, home offices, or hobbies. One of the upstairs bedrooms also has it's own private half bathroom for an upstairs primary bedroom option. Significant improvements include an upgraded 200-amp electrical service, updated kitchen wiring, chimney maintenance and repointing, replaced gutters, and numerous other thoughtful updates throughout. Outside, enjoy the manageable yard, refreshed patio, and low-maintenance vinyl siding. Location is another highlight. Just a short distance from downtown Keene's restaurants, shops, Colonial Theatre, and community events, with the Ashuelot River Park trails and Cheshire Medical Center within walking distance. A wonderful opportunity to enjoy the character of an antique New England home with the comfort of modern improvements in a convenient Keene location.

344 Court St, Keene

Listing courtesy of Jill Exel from BHG Masiello Keene. ()

78 Webb Depot Rd, Marlborough
$265,000
3 Beds ⋅ 1 Baths ⋅ 5116268 MLS
Fantastic opportunity to own 2.3 acres in the beautiful Monadnock Region! This affordable 3-bedroom Cape offers a convenient first-floor bedroom, 3/4 bath, wood floors throughout, replacement windows, durable red vinyl siding, and a spacious back deck perfect for entertaining, outdoor dining, or relaxing and enjoying the peaceful surroundings. An above-ground pool adds to the summer fun, while a storage shed provides extra space for outdoor equipment, tools, and toys! The wonderful flat, level lot offers so many possibilities for outdoor enjoyment, including gardening, entertaining, backyard games, a fire pit, play areas, pets, or simply having plenty of room to spread out and enjoy the outdoors. There's space to create your own backyard oasis! Conveniently located just a short drive to downtown Keene, you'll enjoy easy access to local shops, restaurants, grocery stores, healthcare, entertainment, and Keene State College. Outdoor enthusiasts will love nearby hiking at Mount Monadnock, scenic walking and biking trails, and the many recreational opportunities throughout southwestern New Hampshire. Marlborough offers a local school for preschool through grade 8, with students attending Keene High School for grades 9-12. Enjoy the peace and charm of country living while keeping everyday conveniences close by. Whether you're a first-time buyer, looking for an affordable home with acreage, or seeking room to enjoy the outdoors, 78 Webb Depot Road is full of possibilities. Come see all this property has to offer!

78 Webb Depot Rd, Marlborough

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

16 Monument Rd, Hinsdale
$579,000
4 Beds ⋅ 3 Baths ⋅ 5116265 MLS
This home offers a rare combination of space, acreage, location, features, & value, plus the potential to subdivide. Set back from the road, this immaculate 4-bedroom, 2.5-bath home welcomes you with expansive windows, warm wood tones, & clean architectural lines that create a bright, inviting feel. At the heart of the home, a beautifully renovated kitchen showcases custom cabinetry, granite countertops, stainless steel appliances, an expansive center island spanning over 10 feet, double dishwashers, and a wine cooler. Beautiful hardwood floors flow throughout the open-concept main-level living spaces, perfect for both everyday living & entertaining. The main level includes a private primary suite with a deck overlooking the backyard, custom tile shower, double vanity, and soaking tub. A second bedroom, full bath, & laundry room complete the floor. The finished lower level adds exceptional living space: two more bedrooms, a spacious family room with a fireplace, & half bath. It also offers convenient access to the heated two-car garage & additional storage. With its comprehensive updates just completed, the home has undergone a transformation incorporating modern engineering and energy-efficient features. Virtually every interior and exterior element was improved, including windows, roofing, electrical and plumbing systems, flooring, cabinetry, finishes, fixtures, appliances, & much more. A standby generator & updated in-ground pool overlooking the spacious, level backyard. Easy commute to VT or MA & all the appeal of Southern New Hampshire living, just minutes from shops, dining, schools, hospitals, & everyday essentials. The 1.35-acre parcel offers potential for subdivision or future development, subject to town approvals. Home warranty is included. The space you want. The upgrades you’ll love. Book your showing today!

16 Monument Rd, Hinsdale

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

62 Skyline Dr, Keene
$445,000
3 Beds ⋅ 3 Baths ⋅ 5116187 MLS
Distinctive, inviting, and thoughtfully designed for comfortable, carefree living! This lovely 3-bedroom, 2½-bath condo offers a wonderful combination of spacious living, beautiful surroundings, and the added convenience of a compact Stiltz elevator providing easy access between the first and second floors—an exceptional feature for those seeking enhanced accessibility. A welcoming covered entry opens to a stunning two-story living room filled with natural light, featuring beautiful wood floors, a cozy fireplace, and sliders leading to a fabulous sunroom overlooking picturesque open fields. A comfortable dining room with a large picture window and a well-appointed eat-in kitchen provide inviting spaces for everyday living and entertaining. A convenient half bath and pantry closet complete the first floor. Upstairs, an open balcony overlooks the living area below. The spacious primary bedroom suite offers a private retreat, while two additional bedrooms share an updated bath with a tiled step-in shower. A generous walk-in closet provides excellent storage. The two-car garage adds convenience, while the desirable location puts so much within easy reach! Enjoy a short walk to the community's in-ground pool and clubhouse, the YMCA, and scenic rail trail, with schools, the hospital, and downtown shopping just minutes away. A wonderful opportunity to enjoy the ease of condominium living without sacrificing space, comfort, or accessibility!

62 Skyline Dr, Keene

Listing courtesy of Norma Couture from BHG Masiello Keene. ()

25 Valley St, Keene
$425,000
3 Beds ⋅ 2 Baths ⋅ 5116032 MLS
OPEN HOUSE SAT. 11/14 10:00AM-11:30AM. This charming, larger than it looks east side Bungalow complete with white picket fence has been well maintained and enjoyed by the same family for over 50 years. A modern yet style appropriate kitchen with abundant storage, Corian counters, stainless appliances and recessed lighting opens to the adjacent family room with exposed beams, hearth w/woodstove and sliders to a spacious 3 season sunroom with vaulted knotty pine ceiling and skylights. A formal dining room with triple windows and living room with natural woodwork. Beautiful hardwood and pine floors. Greet friends and family from the enclosed front porch with beadboard ceiling and wood floor. Upstairs you'll find a central bonus room perfect for home office, craft area or hangout for the kids to watch TV/get together with friends, 2 generous sized bedroom and a 3/4 bath with tile shower and skylight. Mini splits on both floors to keep you cool in the summer plus a woodstove to offset your heating oil expenses. Replacement windows. Brand new water heater 10/26. A fantastic, over sized 2 car garage built approx. 2006 with high ceilings, workshop space and a walk up second floor for storage or finishing into additional living space. The rear deck overlooks a nice sized flat yard and patio area. All within walking distance to shopping/dining in Keene's vibrant downtown, the rail trail, outdoor activities at Robin Hood Park, Carpenter Field and Gathering Waters Charter School.

25 Valley St, Keene

Listing courtesy of Wesley St. Pierre from Keller Williams Realty Metro-Keene. ()

67 Tyler Ln, Sullivan
$950,000
3 Beds ⋅ 3 Baths ⋅ 5115997 MLS
A RARE NEW ENGLAND ESTATE 105 ACRES WITH MAGNIFICENT MOUNT MONADNOCK VIEWS! Discover the beauty, privacy, and timeless charm of this extraordinary 105-acre property, nestled along a quiet country lane with spectacular views of Mount Monadnock. This remarkable estate features a circa 1830 post-and-beam Colonial with a 1980 addition, blending historic character with comfortable modern living. The land is truly exceptional, offering substantial organic gardens, a peaceful pond, certified tree farm, beautiful stone walls, a classic barn, fruit trees, a bee yard, and an abundance of wildflowers and perennial gardens. A wonderful opportunity to embrace a sustainable lifestyle, cultivate your own land, and enjoy the natural beauty of the countryside. Inside, the lovingly maintained antique Colonial welcomes you with sunny, bright rooms, charming period details, and beautiful Carlisle wide-plank flooring. The modern, open-concept kitchen and dining area creates a warm, inviting space for entertaining family and friends. The living room, complete with a charming fireplace, is perfect for cozy evenings, while the primary bedroom with en-suite bath offers a comfortable private retreat. Enjoy gatherings with family and friends, spectacular sunsets, and the simple pleasures of country living. With 105 acres to explore, the possibilities are endless—farm, garden, hike, ride, ski, or snowmobile to your heart’s content. Enjoy the peace and privacy of your own remarkable country estate while remaining just minutes from Keene’s excellent restaurants, shopping, theater, and other amenities. A truly special property offering an extraordinary blend of history, natural beauty, and country living. Rarely does an opportunity like this come along!

67 Tyler Ln, Sullivan

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

37 Michigan St, Winchester
$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. ()

22 Page St, Keene
$424,000
3 Beds ⋅ 2 Baths ⋅ 5115913 MLS
Classic New England charm meets modern comfort in this spacious and beautifully updated in-town Keene home! Offering an abundance of character, natural light, and room to spread out, this sprawling New Englander is full of pleasant surprises. The gorgeous kitchen is a standout, featuring beautiful cabinetry, granite countertops, stainless steel appliances and radiant flooring, and a generous breakfast bar perfect for casual dining and entertaining. Warm hardwood floors, beautiful original woodwork, and a handsome staircase showcase the home's timeless appeal, while the bright and inviting living room features a fireplace and lovely bay window. A spacious dining room, convenient first-floor bedroom, and an abundance of storage add to the home's comfort and functionality. Featuring 3 bedrooms and 2 bathrooms, there's plenty of room for everyday living, but the possibilities don't end there! An additional upstairs dwelling unit provides wonderful flexibility for extended family, guests, or potential rental income. The oversized three-story, two-car garage is truly exceptional, offering incredible space for vehicles, hobbies, a workshop, or storage. The space on the 2nd floor could make an excellent ADU! Relax on the welcoming covered porch and enjoy the convenience of an in-town location just minutes from downtown Keene, shopping, restaurants, schools, parks, and the hospital. With its unique combination of historic charm, thoughtful updates, versatile living arrangements, and remarkable space, this is a home that offers far more than meets the eye!

22 Page St, Keene

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

581 Keene Rd, Winchester
$629,000
2 Beds ⋅ 2 Baths ⋅ 5115857 MLS
Discover a unique property offering comfortable living, excellent visibility, and exceptional versatility. This property features a 1,500 SF home/living space, providing an inviting residential space, along with additional buildings and income-producing opportunities. Conveniently located on Route 10, the property offers easy access and outstanding potential for a variety of residential and business uses. In addition to the living area, the property includes a 1,500 SF commercial space and a 3,345 SF garage featuring four bays, a paint booth, and office space. The garage is nearly turnkey and could be ideal for an automotive enthusiast, mechanic, motorcycle hobbyist, or anyone seeking space for a home-based business, subject to applicable approvals. The property also has town permission to display up to ten vehicles for sale and includes a leased food truck site. With the apartment and commercial space already leased, the property offers an opportunity to enjoy rental income while exploring its many possibilities. The garage is currently leased month-to-month at below-market rent, providing flexibility for a future owner to occupy the space or maximize its income potential. The previous garage tenant paid $2,700 per month, and projected net operating income for the property is approximately $45,795 annually once the garage is leased at market rates. Serviced by private well and septic, this distinctive property combines residential living with additional space, income potential, and versatility in a convenient Winchester location. Whether you're looking for a property with room for your hobbies, space for a business, or an opportunity to supplement your income, 581 Keene Road offers a compelling combination of possibilities.

581 Keene Rd, Winchester

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

9 Skyview Cir, Keene
$445,000
4 Beds ⋅ 2 Baths ⋅ 5115794 MLS
Delightful 3-4 BDR, 2 Bath condo w/many recent updates. Inviting & beautifully designed dine-In Kitchen w/granite counter top, 10' of prep area, triple window over the sink, soft close cabinets & pantry w/French glides, granite topped 4'x4' island w/seating for 4, under the counter drawers & more storage. All Whirlpool stainless appliances, Lazy Susan, pullout spice rack & under the cabinet lighting. LR/DR combination 7'5" ceiling, hardwood flooring, ceiling lights, wood fireplace & patio doors right out to the year round sunroom. Sunroom w/new mini-split, all new windows & exterior door. Sunroom has a skylight. Wonderful room to watch the birds and the weather. 1st FLR BDR w/Palladian window, a wall of closet space, ceiling fan, hardwood floor & skylight. Full bath w/Corian counter top & under the counter storage. Open stairway w/hardwood flooring. Front BDR #2 w/triple window w/a view, ceiling fan, terrific walk in closet w/many fixtures & beautiful hardwood floor. Corian sink in 3/4 bath, separated laundry area & shower area. Linen closet in the 2nd FLR hallway. Rear BDR #3, w/triple window, plus a wall of closet space. Plenty of closet space in this home. Attic room had a skylight and in 2023 this room was converted into a Family Rm, 4th BDR or a great Office space. There is also a walk-in attic storage room. Garage windows were replaced & gutters were added in 2025. Association offers an in-ground pool & community club house. Great area to walk & bike w/nearby trails and the YMCA. Carefree living w/exterior maintenance taken care of, including snow removal, lawn care and landscaping. Welcome to Skyview Circle.

9 Skyview Cir, Keene

Listing courtesy of Connie Joyce from RE/MAX Town & Country. ()

21 Split Oak Cir, Chesterfield
$409,900
3 Beds ⋅ 2 Baths ⋅ 5115682 MLS
There’s something special about a home with room to spread out, enjoy the outdoors, and make it your own! This 3-bedroom, 1.5-bath contemporary in desirable Chesterfield, NH, sits on an open corner lot with space for gardening, outdoor activities, and enjoying seasonal views. Just a short drive from Keene, NH, and Brattleboro, VT, and around the corner from Spofford Lake, this location makes it easy to enjoy the best of the area. Inside, the oversized living room is the heart of the home, featuring vaulted ceilings, abundant natural light, and a central fireplace with wood stove insert for cozy New England evenings. The wraparound deck extends the living space outdoors, perfect for morning coffee, summer dinners, and gathering with friends. The adjoining dining area and galley kitchen create a practical, connected layout. Upstairs, three nicely sized bedrooms and a full bath offer comfortable space to unwind. The lower-level bonus room, accessed from the attached garage, is ideal for a home office, gym, family room, or hobby space, with a half bath and laundry area adding extra convenience. Over the past three years, the current owner has completed an impressive list of updates, including a new roof, heating system, hot water heater, well pump, windows, garage door, kitchen appliances, interior and exterior paint, landscaping, and a 12x24 shed, among other improvements. With many major items already taken care of, you can focus on adding your own personal touches and making this home your own. Great value, inviting living spaces, and a wonderful location make this Chesterfield home worth a closer look!

21 Split Oak Cir, Chesterfield

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

549 West St, Keene
$439,900
4 Beds ⋅ 2 Baths ⋅ 5115638 MLS
Some homes have a personality all their own, and this West Keene Craftsman bungalow is ready for its next chapter! Built circa 1929, this inviting property offers a wonderful blend of timeless craftsmanship, original character, and thoughtful improvements. The care and pride the previous owner brought to this home can be appreciated in the details and the work completed throughout, making it a special opportunity for its next owner. From the moment you arrive, the welcoming front porch sets the tone. Inside, beautiful hardwood floors, rich woodwork, timeless built-ins, a distinctive board-and-batten living room ceiling, and a cozy fireplace showcase the craftsmanship that gives this home its unmistakable charm. Thoughtful attention to detail and the home's enduring features create a warm and inviting atmosphere. The updated kitchen offers stainless steel appliances and generous workspace, while the adjoining formal dining room provides a natural gathering place for meals, celebrations, and everyday moments. The flexible layout includes a first-floor bedroom or office and a full bath. Upstairs, three additional bedrooms, another full bath, and a dedicated laundry room offer space to accommodate a variety of needs. Looking for spaces to enjoy beyond the indoors? Start your day on the welcoming front porch or settle into the three-season porch overlooking the backyard. A detached garage adds convenience, while the established West Keene location puts schools, parks, and neighborhood amenities nearby. There's another exciting possibility here: the property is zoned for professional service businesses, offering potential for buyers interested in exploring permitted business uses, subject to applicable zoning requirements and approvals. Whether you're drawn to vintage craftsmanship, appreciate a home that has received thoughtful care, or are excited to bring your own ideas to a classic property, this bungalow deserves a closer look. Schedule private viewing today.

549 West St, Keene

Listing courtesy of James W Letourneau from North New England Real Estate Group. (Phone: 603-562-9849)

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