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32 Colby Farm Rd, Chester
$1,820,000
4 Beds ⋅ 4 Baths ⋅ 5090572 MLS
Some homes check boxes. This one rewrites the list entirely. 32 Colby Farm Road is a 5,100 sq ft modern farmhouse on a pristine acre in one of Chester's most exclusive new subdivisions. From the sweeping farmers porch to the last carefully chosen finish, every detail tells you this one is different. Inside, 9-ft ceilings, hardwood floors, a custom coffered 10-ft ceiling in the family room, and a vaulted wood ceiling in the sunroom create a main level that's as warm as it is impressive. The kitchen is a chef's dream: Thermador 48" gas range, dual fuel oven, oversized hood, and 42" built-in refrigerator, backed by a fully equipped scullery with its own oven, sink, and dishwasher. Entertaining here isn't just easy,it's genuinely fun. The main-floor primary suite is pure retreat, with a private deck and a spa bath featuring radiant heated floors, a frameless glass shower with dual rain heads, marble bench and surround, brushed gold fixtures, and a freestanding soaking tub. Yes, all of that. Upstairs delivers just as much — a second primary suite, two additional bedrooms, movie room, second laundry, a common bath with dual vanities and a separate toilet and shower room, and an oversized bonus room with in-law or au pair suite potential. And then there's the walkout basement — bright, open, and full of possibility. French doors and oversized windows flood the space with natural light, making it feel anything but like a basement. Already pre-plumbed for both a full bathroom and a kitchen, the groundwork is laid for whatever you envision — a guest suite, home gym, recreation room, or a fully independent living space. Few homes at this level offer this kind of potential right out of the gate. The 3-car garage has 11-ft ceilings, and a large rear deck is ready for every gathering you've been meaning to host. This is the home people drive by and wonder about. Now's your chance to stop wondering.

32 Colby Farm Rd, Chester

11 Tenney Rd, Chester
$1,600,000
4 Beds ⋅ 4 Baths ⋅ 5072613 MLS
Privately set on 27 acres, this exceptionally well-built geo thermal Craftsman Cape is a rare offering where land, lifestyle, and lasting quality converge. Reached by a long, newly paved drive, the property delivers privacy w/ the flexibility to live, work, and create—without compromise. A Kemper cabinetry kitchen— w/ Fisher & Paykel & Miele applcs. incl. custom-made refrig. cabinet— and 8' island anchors the main level flowing seamlessly into a dramatic two-story family rm w/ stone gas fireplace and expansive dining area. A first-floor office, three season rm, and pantry complete the thoughtful main layout. Upstairs, the primary suite offers a peaceful retreat w/cathedral wood ceilings, private balcony, custom walk-in closet, and spa bath. The walk-out lower level is curated for leisure and hosting, featuring custom bar, media area, Tonal home gym, guest suite, and direct access to outdoor living w/ firepit, outdoor kitchen, natural stone waterfall, and swim spa trainer. Beyond the home, a radiant-heat & air-conditioned 40x60 outbuilding provides exceptional versatility for car storage, hobbies, or business use, complemented by a 16x32 custom-built barn w/hay loft & fenced pen for small-scale agricultural living. Built with intention and efficiency—geothermal htg.&AC, 48kw generator, heated garage, plaster walls, 9' ceiling, steel beams, Walcott windows, whole house sound/video system, refinished wide pine flrs —and defined by permanence, privacy and enduring craftsmanship.

11 Tenney Rd, Chester

417 Candia Rd, Chester
$1,400,000
3 Beds ⋅ 3 Baths ⋅ 5073874 MLS
Turnkey 4,300+ sq. ft. contemporary estate with a heated 8+ stall barn set on 10 private acres. The interior features a dramatic two-story entryway leading to a light-filled floor plan. The step-down living room is anchored by hardwood flooring and a wood-burning fireplace with a granite surround. The kitchen includes updated appliances, a new walk-in pantry, and sliders to an expansive deck with dual staircases to the backyard. A dining room, sunroom with pastoral views, family room, guest room, and laundry-equipped half bath complete the first floor. On the second level, the primary suite offers a private balcony, sitting area, custom wardrobe, and a full bath with a jetted tub and new double vanity. Two additional bedrooms share a Jack-and-Jill bath and one has a private balcony. A partially finished basement provides space for guests or a home gym. The property includes a heated two-car garage with a workshop and a refurbished barn with grain and tack rooms. Equestrians will enjoy fenced paddocks, an outdoor arena, and miles of private riding trails and direct access to 20+ miles of trails across thousands of acres of public land. A new, professionally engineered bridge crosses a brook leading to a horse run-in. The grounds feature a furnished off-grid cabin with a private bath, two gazebos, two stone fire pits, and an outdoor hot tub. Recent upgrades include a new roof, well pump, water filtration, and hot water heater, plus a generator hook-up and whole-house AC. This estate offers complete privacy with no visible neighbors, yet remains an easy commute to Concord, Manchester, Portsmouth, and Boston.

417 Candia Rd, Chester

35 Colby Farm Rd, Chester
$1,363,848
3 Beds ⋅ 3 Baths ⋅ 5072856 MLS
Home to be built in the desirable Colby Farm Subdivision in Chester, NH. This offering presents a rare opportunity to build new in an exclusive enclave surrounded by conservation land, providing privacy, natural beauty, and a peaceful setting. With only four homesites remaining, opportunities like this are increasingly limited. The proposed farmhouse-style design features open, light-filled living spaces, a spacious kitchen ideal for entertaining, a dedicated dining area, and flexible floor plan options to suit a variety of lifestyles. The second level includes a private primary suite, additional bedrooms, and convenient second-floor laundry. A welcoming front porch and a three-car attached garage complete the design. Buyers may choose this plan, select an alternate builder-approved plan, or bring their own custom design. At this stage, buyers can personalize all finishes, including cabinetry, countertops, flooring, fixtures, and color selections, creating a home tailored to their individual preferences and design vision. Colby Farm is a limited subdivision of just 10 homes, offering a quiet country atmosphere while remaining convenient for commuters, with easy access to Route 93 and a reasonable commute to Boston. Close to Chester village amenities, outdoor recreation, and major routes, this is a unique opportunity to create a custom home in one of Chester’s most sought-after new neighborhoods.

35 Colby Farm Rd, Chester

125 Crowley Rd, Chester
$1,315,000
4 Beds ⋅ 3 Baths ⋅ 5082840 MLS
Stunning brand NEW home complete and ready to love! This "knock your socks off" modern farmhouse is sure to impress! Finished with high quality designer choices and built with quality you can see EVERYWHERE! With over 3600 sq ft and room to expand in a walk out lower level with a HUGE 9' slider! Wide plank maple flooring throughout the entire house, stunning quartzite and marble countertops, custom millwork and crown moldings, built in benches and pantry organizer, true stone veneer gas fireplace, tile walk in shower with rain shower head and built in handheld bar, stone veneer accents on the exterior, granite walkway, circular driveway...it doesn't get much better than this! Gorgeous kitchen and butler's pantry, tile backsplash, under cabinet lighting. Custom Hood with 36' commercial KitchenAid gas stove and KitchenAid micro drawer and dishwasher. And with quality Mathew's Brothers windows, Rinnai on demand tankless H20, high efficiency FHA with AC, metal roof accents, gorgeous cupola...the quality is all there too! The floor plan boasts an impressive open concept with a livable design that welcomes entertaining. First floor study, two farmer's porches, huge rear deck, his and her's walk in closets, charming second floor loft/nook, tons of light filled windows, HUGE master retreat with a luxurious bath and a three-car attached side loaded garage!

125 Crowley Rd, Chester

149 Crawford Rd, Chester
$1,170,000
4 Beds ⋅ 3 Baths ⋅ 5086058 MLS
Welcome to 149 Crawford Road in the charming country town of Chester, New Hampshire. This meticulously maintained expansive cape style home showcases true pride of ownership throughout. Thoughtfully designed with elegant shaker-style wall paneling and high-end finishes, this property blends timeless character with modern comfort. Step inside to a bright, open-concept first floor featuring a newly remodeled kitchen that flows seamlessly into a cozy sitting area with a gas fireplace and a sun-filled sunroom overlooking the backyard and pool. The first-floor primary suite is a private retreat, complete with a sitting area and sauna. An additional bedroom, full bath, beautifully designed laundry room, mudroom nook, living room, and formal dining room complete the main level. Upstairs, you’ll find two generously sized bedrooms, a full bath, and a welcoming gathering nook—ideal for guests or family. A spacious bonus room with skylights and its own staircase offers endless possibilities, including potential for an in-law suite with ample unfinished above-ground space great for Multi-Generational Living. Outside, enjoy your own backyard oasis featuring a stunning in-ground gunite pool and scenic views—perfect for entertaining or relaxing. Take in local fireworks right from your deck. Additional highlights include a brand-new roof and solar panels for added efficiency. Three Car Heated Garage. The list goes on with updates and features. Please see the marketing packet for full details. Conveniently located within 30 minutes of the coast, roughly an hour to Boston, and to the Lakes Region, this home is set in a well-established neighborhood within the sought-after Pinkerton Academy district. A rare opportunity offering space, flexibility, and lifestyle—this is a home you won’t want to miss. Showings Begin Saturday May 2, 2026 By Appointment Only!

149 Crawford Rd, Chester

78 Stonebridge Dr, Chester
$1,050,000
4 Beds ⋅ 3 Baths ⋅ 5062949 MLS
Perched atop the coveted cul-de-sac Of Stonebridge Drive, this luxury residence offers a sanctuary of unparalleled privacy and sophistication. As you approach, immaculately manicured lawns and lush greenery evoke the grandeur of a private estate, welcoming you into a world of refined elegance. Timeless craftsmanship with modern luxury on 4.2 acres of pristine landscape. The interior is a masterpiece of design featuring a gourmet kitchen outfitted with premium appliances and elegant finishes, while custom built-ins in the expansive living room reflect impeccable attention to detail. Every corner of this residence exudes warmth and grace. Ascending to the primary suite reveals a true retreat adorned with a tray ceiling softly illuminated by hidden lighting, rich hardwood floors and elegant glass French doors that open into a sumptuous walk-in closet. The ensuite bath is a spa-like haven showcasing a custom tile shower, intricate basket weave accents and a magnificent soaking tub-an ideal sanctuary for relaxation and renewal. The outdoor living space features a sleek modern deck and a shimmering in-ground pool-perfect for gracious entertaining or quiet moments of reflection. The serene outdoor spaces provide an idyllic escape for restoring your mind, body and spirit. This unparalleled home embodies a harmonious blend of elegance, comfort and serenity-a timeless retreat where every element has been thoughtfully curated to elevate your lifestyle to extraordinary heights.

78 Stonebridge Dr, Chester

1847 Trebo Rd, Chester
$950,000
4 Beds ⋅ 4 Baths ⋅ 5048707 MLS
With only 50 stone homes in all of Vermont, this one stands out as possibly the most beautiful; uniquely situated on 20 acres of gorgeous green lawn, fields, forest, rolling hills, extensive stone walls. A mere 2 miles to Chester. Since 2020 the house has been transformed & restored w/improvements such as interior & exterior paint, new windows & French Doors, stone steps & walkways, 50 panel Solar Array, extensive drainage & excavation work for a drier basement. Radiant floor heat in 3 bathrooms, kitchen & great room. An open, sunny, 750sf apartment w/separate entrance, new kitchen, windows, cork floor, laundry hook-ups, is ready for family, guests, renters. BA w/clawfoot tub has been added between first floor BR & serene spare room which could be easily expanded to create a larger bath, dressing room, nursery, office. Attached 2 car garage has a new metal roof, drywall ceiling, EV charger. The home has delicious well water, beautiful views from every window, and because of the thick stone wall construction, stays cool in the summer, warm in the winter, incredibly quiet and draft-free. A newer, solidly built 8-stall horse barn w/wonderful hay loft, sits surrounded by fields atop a nearby knoll dotted with daffodils in springtime. Also includes: Fiber optic internet, professional landscaping including many new trees & native perennials, new boiler, buried propane tank, new electric service & some new plumbing. COME SEE THIS AMAZING PROPERTY!!! OPEN HOUSE OCT 4TH. 11AM-2PM

1847 Trebo Rd, Chester

53 Meadow Fox Ln, Chester
$920,000
3 Beds ⋅ 4 Baths ⋅ 5082534 MLS
OPEN HOUSE CANCELLED on 5/2 - UNIQUE California Ranch, ONE-LEVEL LIVING with IN-LAW/ADU - Set on 2+ PRIVATE acres in desirable Chester Hill Estates. Pinkerton Academy District. Elegant, covered entrance, once through the FOYER this home is filled with subtle custom details, gleaming HARDWOOD FLOORS, and abundant natural light throughout. 5 Bedroom Potential, the study with a closet easily serves as a bedroom. Designed for flexibility, the home features an approved IN-LAW/ADU in the lower level with SEPARATE ENTRANCE, perfect for multi-generational living. The open floor plan offers an oversized living room with a wood-burning fireplace and a SPACIOUS kitchen with an eat-at island, GRANITE counters, under cabinet lighting SUBWAY tile backsplash, work DESK area, plus a COVERED PORCH for seamless indoor-outdoor entertaining. The primary suite includes a jetted tub, double sinks, separate shower, large walk-in closet, and a private deck overlooking the IN-GROUND HEATED POOL (depth about 5 feet both ends) with PAVILLION. Need even more space? The finished lower level provides additional living area with the in-law/ADU set up with kitchen and bath or huge family room. Additional highlights include many HANDICAP-ACCESSIBLE FEATURES: Jack & Jill WET ROOM BATH, garage RAMP, hardscape WALKWAY to the pool, most doors 36 inch with lever handles and BARN DOORS for easy room transition. System: Forced hot water heat with 6 zones and advanced boiler controls, dual oil tanks, central A/C for summer comfort, and generator-ready wiring for peace of mind. Repaired/Replaced - 2017: Kitchen & Appliances, 2018: A/C, 2019: Hardwood refinish, 2022: Roof, Gutters, Pool Reline, 2023: Pavilion, fence, irrigation, Siding, 2024: Refrigerator, Tree pruning\New Grass. AGENTS & BUYERS to do their own Due Diligence to verify all listing information. Room sizes are for reference only; not guaranteed. 3 bedroom septic. Quick Close Possible. Some exterior photos AI enhanced.

53 Meadow Fox Ln, Chester

111 Sandown Rd, Chester
$920,000
3 Beds ⋅ 3 Baths ⋅ 5070353 MLS
Open House CANCELLED! Are you a Car Enthusiast, Business Owner or Need Storage? This Property has Something That You Might Like!! Elevated on an open 3.4 acres with a serene setting, this property really makes a statement. This Oversized Cape has SO MUCH TO OFFER. Potential for 5 bedrooms, with 3 being on the main level. Loaded with natural light, the open flow creates a perfect space to entertain The main living level has an updated Kitchen w/ large island, a Huge 22x17 Family Room w/fireplace, Primary Bedroom w/ vaulted ceilings and 2 additional large bedrooms. 2 Full Bathrooms, 1st floor laundry, dining room, and an amazing three season room complete the main living level. The second floor is partially finished w/ another large bonus room, and the other half could be also be finished. Need more space? Partially finished basement offers more opportunity & flexibility in the floor plan! And now back to the car enthusiast or business owner! You will be more than impressed with the detached 36 x 40 Garage! Insulated, Heated and on its own electrical panel, one bay even has a CAR LIFT to work with ease. (2) 10ft doors & (1) 12ft door allows you to park an RV or Boat without a second thought. Enjoy morning coffee sitting on the farmers porch or gathering on the back deck with fully fenced in backyard. In addition to the many updates & upgrades offered this home has been meticulously maintained! See attached listing packet for a list of ALL updates offered here.

111 Sandown Rd, Chester

27 Haverhill Rd, Chester
$910,000
4 Beds ⋅ 3 Baths ⋅ 5099955 MLS
Rarely does a historic home of this caliber become available. Set in the heart of Chester's antique village center, surrounded by homes as storied as its own, this classic residence is an exquisite, well-kept treasure showcasing authentic period details and flawless updating throughout. Step inside to the gracious entry with an open stairway, setting the tone for a home where craftsmanship and character are on full display. Wide plank pine floors, original Indian shutters, gunstock corners, and period millwork carry that story through nearly every room. The formal dining room has its own fireplace and exposed beams overhead providing a warm, handsome space for entertaining. A nearby powder room adds flexibility, easily doubling as a first-floor bedroom if needed. The kitchen blends old and new with ease. Stainless appliances, a granite island, a sunny breakfast nook where the original colonial fireplace still anchors the room. Upstairs, the primary suite feels like its own retreat, with a comfortable sitting area and walk-in closet. Two more bedrooms, each with a fireplace, a recently updated main bath, laundry, and a 4th room, currently used as a walk-in closet, round out the second floor. An expansive bonus space above the three-car garage offers additional living area, perfect for movie nights, watching the big game, or a fabulous guest suite. Located just steps from the bonus room, a den and 3/4 bath create a seamless layout offering potential for a private accessory apartment. Tucked into conservation land on three sides, the grounds offer a rare, enveloping privacy, gardens to enjoy and an inviting inground heated pool for the warmer months. 27 Haverhill Rd has stood for over two hundred years, lovingly maintained and thoughtfully updated without losing what makes it special. Now, it's ready for its next chapter, all it is missing is you! Showings begin Friday, July 17th at noon. Open Houses Friday 7/17 5-7pm and Saturday 7/18 12-2pm. Video Tour below

27 Haverhill Rd, Chester

322 Meadow Fox Ln, Chester
$910,000
4 Beds ⋅ 3 Baths ⋅ 5084336 MLS
Offer deadline Monday 4/27/26 @ 12pm. Please allow 24 hours for decision. This is more than a home - it’s a lifestyle property offering privacy, space, and the opportunity to enjoy every season New England has to offer. Set on over 9 private acres in one of Chester’s most desirable neighborhoods within the Pinkerton Academy district, this meticulously maintained 4-bedroom Colonial offers the perfect balance of space, comfort, and lifestyle. From the moment you arrive, the setting invites you to slow down and take it all in lush surroundings, scenic trails, and a backyard designed for both relaxation and unforgettable gatherings. The heated saltwater in-ground pool, expansive patio, and partially covered deck create a true outdoor retreat, ideal for summer entertaining or quiet evenings overlooking the peaceful landscape. Inside, a welcoming foyer opens to a thoughtfully designed main level featuring hardwood floors and fresh updates throughout. The kitchen is the heart of the home, complete with stainless steel appliances and a custom peninsula for casual dining, flowing seamlessly into a formal dining room and an impressive great room with vaulted ceilings, a wood-burning fireplace, and custom built-ins. A second living area or home office adds flexibility, along with a convenient half bath and laundry. Upstairs, the spacious primary suite offers a private retreat with vaulted ceilings, a walk-in closet, and an ensuite bath with a double vanity and whirlpool tub. Three additional generously sized bedrooms and a full bath complete the second floor. The finished lower level expands your living space with a warm, inviting feel, featuring a gas fireplace, home theater setup, built-in bar, and direct walkout access to the backyard and pool area. Additional highlights include a walk-up attic for future expansion, a water softener system, new mini-splits, updated electrical, smart home features, and abundant storage. Two-car garage under and a detached two-car garage.

322 Meadow Fox Ln, Chester

14 Stacey Ln Unit 2, Chester
$870,000
3 Beds ⋅ 3 Baths ⋅ 5084563 MLS
WOW No Cookie Cutter Here! Check Out this Stunning Contemporary Farmhouse in the Quintessential New England small town Of Chester, NH located in a fantastic Small Development with only 9 Detached Condo's. The home Features 3 beds,2 1/2 baths with an Open concept layout. The GORGEOUS Kitchen has all the bells and whistles, granite counter tops, a Huge island, stainless steel gas stove with vent hood that connects to a large living room with Gleaming Hardwoods floors. You are sure to Enjoy the Elegant Dining room adjacent to the kitchen along with a home office with French Doors. The 1st Floor Primary Suite has Hardwood floors and a STUNNING Tiled Shower, double Vanity, and a walk-in closet that also connects to the Laundry Room. The mud area and powder room complete the first level. Upstairs you will find a MASSIVE Bonus room that is sure to be an amazing place to entertain or just hang out with the family. The 2nd bedroom is Gigantic and can be another primary suite, it has a large walk-in closet and connects to a large full bathroom with double vanity. The 3rd bedroom is also Huge and connects to the full bathroom as well. Outside you have a huge deck and plenty of room for the kids or pets to run around. The massive basement provides tons of storage and space that is ready to finish. Quick Closing Possible. Some photos are Virtually Staged. This is a MUST SEE HOME !

14 Stacey Ln Unit 2, Chester

72 Jenkins Farm Rd, Chester
$845,000
3 Beds ⋅ 3 Baths ⋅ 5073130 MLS
You've been waiting for this one! Neighborhood, true open floorplan, beautiful landscaping w/INGROUND HEATED POOL-it's ALL HERE! Your new home has been impeccably prepared for you & designed for easy living. Farmers porch, family room with gas fireplace, granite kitchen counters w/an abundance of cabinet space plus additional pantry! Stainless steel appliances and gas range-all recently new in 2025. Sliding glass doors off the kitchen/dining area will lead you to your large deck for year-round grilling if you choose. Half bath is tucked away off the mudroom coming in from the garage. Head up the split staircase to find a fabulous spacious 2nd family/gameroom stocked with your own pool table, bevvy fridge and separate 2nd floor laundry room. Primary ensuite w/walk-in closet overlooks the backyard and feels spacious and serene. The tastefully updated ensuite bathroom is large and bright, yet perfectly private. Dual sinks, soaking tub & a separate oversized shower. whole house GEOTHERMAL central heating/cooling system means low maintenance and notoriously quiet! Vacation at home in your beautifully landscaped backyard equipped with irrigation, your very own inground pool, patio & plenty of additional yardspace for more fun. Unfinished basement provides plenty of storage or finish as you like! Truly too much to list-ALL this in the Pinkerton School District!! ALL OFFERS DUE 1/12/26 8PM please

72 Jenkins Farm Rd, Chester

58 Orcutt Dr, Chester
$825,000
4 Beds ⋅ 3 Baths ⋅ 5078028 MLS
Welcome to this stately Colonial set on 2 private acres, offering the perfect blend of timeless elegance and modern updates. With 4 spacious bedrooms and 2.5 bathrooms, this home provides room to grow, gather, and entertain in style. Step inside to find a recently updated kitchen featuring beautiful quartz countertops, abundant cabinetry, and a seamless flow into the eat-in area and expansive great room. The open-concept design creates the ideal space for everyday living and hosting, highlighted by vaulted ceilings and a cozy fireplace. A second fireplace—wood-burning—adds warmth and ambiance to additional living space, perfect for relaxing evenings at home. For more formal occasions, enjoy the classic formal dining room, ideal for holidays and special gatherings. Updated bathrooms throughout the home add a fresh, modern feel. Upstairs, retreat to the impressive primary suite, complete with a walk-in closet and en-suite bath featuring a jetted tub—your own private spa experience. Outside, a large deck overlooks the serene, wooded backyard, offering privacy and a peaceful setting for entertaining or quiet mornings with coffee. The 2-acre lot provides space, beauty, a Reeds Ferry shed for storage, and endless possibilities. A roof just 4 years old offers added peace of mind. This exceptional property combines classic Colonial charm with today’s most desirable features—privacy, space, and thoughtful updates—all in one remarkable home located in one of Chester's most desirable neighborhoods.

58 Orcutt Dr, Chester

32 Stacey Ln, Chester
$825,000
3 Beds ⋅ 2 Baths ⋅ 5060101 MLS
WOW another Quality home by DJ Development. Check out this Beautiful Craftsman Style Ranch Home in Chester, NH a Quintessential New England Town. Located in a small 9 Unit Detached Condo Development with a LOW FEE ! The home features one level living at its finest with an open concept Kitchen, Living Dining areas,3 beds,2 Baths with a stunning Primary Bedroom En Suite with an AMAZING Tiled shower with glass door and a bench seat, double vanity, linen closet and HUGE Walk In Closet. You will love the convenience of the laundry room right outside of the primary bedroom. Split floor plan with 2 bedrooms on the other side of the house that shares a Full Bath. Gleaming Hardwood floors throughout, gorgeous Kitchen with granite countertops and a HUGE Island. Stainless Steel appliances, gas stove and walk in pantry. Vaulted ceilings in the great room with recessed lights and gas fireplace. There is a Very large Trex deck out back with nice privacy overlooking the woods. Oversized 2 car garage with EV hookup and so much more. This is a Must-See home that is MOVE IN READY for a QUICK Closing. Backup Offers Requested. Some Photos are Virtual Staging !

32 Stacey Ln, Chester

12 Robin Way Unit 5, Chester
$815,000
4 Beds ⋅ 3 Baths ⋅ 5075427 MLS
2026 means a brand-new home! Welcome to the Condor Farmhouse at Pipit Estates. This popular house style offers a wonderfully welcoming and functional floor plan with room for everyone. The Eat-in Kitchen is perfect with granite counters, stainless steel appliances, and a large pantry. An extra "Flex Room" can be utilized as a formal Dining Room, Playroom, or perhaps an Office. The Mudroom with an entrance from the garage will be a handy space for all. 3 spacious Bedrooms, a Primary Bedroom with attached Bathroom, and a large Laundry Room complete the second floor. The full basement is a walk-out with slider and daylight windows, perfect to finish in the future for additional living space. Pet friendly community and no age restrictions. Beautiful country setting with over 16 acres of open space. Take advantage of all the charming town of Chester has to offer including a top-rated school system! There are additional floor plans to choose from including Ranch homes for single floor living.

12 Robin Way Unit 5, Chester

810 Quarry Rd, Chester
$815,000
3 Beds ⋅ 3 Baths ⋅ 5070079 MLS
Not quite 20 years young, this charming custom-built colonial sits on a private knoll, surveying its 77+/- acre parcel. Blending country comfort and eloquence, you'll find quality craftsmanship throughout, such as blue stone floors and a stone archway. Wide plank floors lead to the country kitchen with soapstone countertops. Enter the spacious dining room with tray-beamed ceilings and oversized windows. A beautifully ballastered central staircase separates the main level. The living room features a masonry brick fireplace and built-in cabinetry. The house has radiant heat on the main level to combat cold winter days. The second floor features a primary suite with a soaking tub and a double sink. Bedrooms two and three share a 3/4 bath. On the top floor, you'll find a large finished space ready for your creativity. Over the two-car garage is office space or a bonus room, which is also accessed by a second staircase. The exterior offers a stone patio ready for summer BBQs or a new firepit for the colder months, and trails that crisscross the 77 acres. There are long-range views that can be opened. Located near the historic Chester Village and a short drive to Okemo, Magic, or Bromley. (acreage is enrolled in the Current Use Program for tax benefits). If you're looking for acreage, plenty of space, and privacy, don't wait to view this unique property. Visit the Okemo real estate community today. Taxes are based on current town assessment.

810 Quarry Rd, Chester

1342 Old Stage Rd, Chester
$805,000
2 Beds ⋅ 2 Baths ⋅ 5056637 MLS
Welcome to your own private retreat—98 acres of Vermont beauty offering meadows, woods, two ponds, and eight versatile outbuildings. Thoughtfully maintained, this charming home is nestled in a park-like setting complete with long, historic rock walls, mature trees, and lovely perennial gardens. Nature lovers will appreciate the abundance of wildlife, from hummingbirds and ducks to deer and the occasional moose wandering past the apple trees and blueberry bushes. Step onto the screened porch overlooking the main pond, perfect for morning coffee or evening relaxation. Inside, warm wood floors and exposed beams enhance the home’s country elegance. The open-concept living and dining area flows into a light-filled kitchen with floor-to-ceiling windows framing views of a mountain you own. The home features two nice-sized bedrooms and two full baths, offering comfort and practicality. Additional amenities include a large pantry/laundry room and easy access to a full concrete basement, ideal for storage or workshop space. Beyond the home, wooded trails lead to the back acreage and a hidden, spring fed pond perfect for secluded swims. There's subdivision potential, with 14+ acres already surveyed across the Grafton line—an investment opportunity or space to expand your vision. Perfectly situated between the charming villages of Chester and Grafton, this is more than a home, it's a lifestyle.

1342 Old Stage Rd, Chester

43 Emerson Rd, Chester
$800,000
4 Beds ⋅ 3 Baths ⋅ 5097911 MLS
Looking for a 4-bed colonial in Chester with space, privacy, and an ideal layout for entertaining? Welcome to 43 Emerson Road Where timeless Colonial charm meets comfortable everyday living. This well-maintained home set on two private acres is in a desirable cul-de-sac neighborhood. Enjoy spacious living areas, inviting outdoor spaces. Nestled on 2 private acres in a peaceful cul-de-sac neighborhood, this 4-bedroom, 3-bathroom Colonial offers the perfect balance of privacy, community, and convenience. The open and inviting first floor is designed for both daily living and entertaining, featuring a spacious kitchen, formal dining room, and an expansive family room with a soaring vaulted ceiling and cozy gas fireplace. New carpeting adds a fresh touch, making this home move-in ready. Step outside to your own backyard retreat featuring a multi-tiered deck, sparkling pool, and a private outdoor oasis designed for summer gatherings, barbecues, and relaxing evenings with family and friends. The generous two-acre lot provides room to play, garden, or simply enjoy the peaceful natural surroundings. Not far from shopping, dining, recreation, and major commuter routes while still offering the charm and tranquility that make Chester one of southern New Hampshire's desirable communities. Served by the highly regarded Pinkerton Academy school district. Whether you're hosting memorable celebrations or enjoying quiet evenings at home, this property delivers the lifestyle you've been searching for. Come experience everything 43 Emerson Road has to offer and discover why so many are proud to call Chester home. Schedule your private showing today. Showings begin Monday July 6, 2026

43 Emerson Rd, Chester

725 Flamstead Rd, Chester
$800,000
4 Beds ⋅ 4 Baths ⋅ 5063387 MLS
Beautifully maintained 2005 Contemporary Cape nestled on 6.7 private acres with sweeping long-range Vermont views. Owned and cherished by just one family, this move-in-ready home offers the best of country living with modern updates. The completely renovated kitchen boasts a Wolf range, Sub-Zero refrigerator, Bosch dishwasher, and quartz countertops, seamlessly flowing into the dining area—perfect for entertaining. The cozy living room features a wood-burning fireplace insert and opens via sliding doors to a multi-level deck with panoramic views. Enjoy peaceful mornings on the wraparound covered porch surrounded by nature. With 4 spacious bedrooms, including a serene primary ensuite, there's room for everyone. The finished walkout basement includes a large exercise room, office with wood stove, full bath, and guest bedroom. Recent upgrades include Brazilian rosewood flooring upstairs and a whole-house Kohler generator. The extended one-car garage includes a full workshop space. Paved driveway for easy maintenance. Outside, explore walking trails, tap 14 mature maple trees, or harvest blueberries and strawberries from your own garden. Only minutes from Chester’s charming town green—this is Vermont living at its finest.

725 Flamstead Rd, Chester

116 Fiddlehead Ln, Chester
$795,000
4 Beds ⋅ 3 Baths ⋅ 5086303 MLS
Nestled in one of Chester’s most sought-after subdivisions, this 4-bedroom, 3-bath Colonial sits on over 3 private acres, offering both privacy and a welcoming neighborhood setting. Enter through the front foyer into the open-concept kitchen and dining area, now featuring an updated kitchen with newer appliances, an induction stove, and plenty of storage. Enjoy casual meals in the eat-in area or entertain in the formal dining room. The great room showcases tray ceilings and a cozy gas fireplace, creating the perfect space to gather. This level also includes a first-floor office with its own fireplace and granite hearth, along with a convenient half bath and laundry. Upstairs, the spacious primary suite offers a walk-in closet and private bath with a jetted tub and separate shower. Three additional bedrooms and a full bath complete the second floor. Other highlights include hardwood flooring throughout, central air, a whole-house generator, irrigation system, large deck, fully fenced back-yard, fiber optic internet, and an electric vehicle charger. The furnace and roof are newer, and the interior has been freshly painted, making this home truly move-in ready.

116 Fiddlehead Ln, Chester

648 Haverhill Rd, Chester
$790,000
3 Beds ⋅ 3 Baths ⋅ 5068060 MLS
Welcome to 648 Haverhill Road - A stunning Contemporary home offering 3,264 sq. ft. of elegant living space on a serene 6.45-acre lot. Built in 2008, this thoughtfully designed residence combines modern comfort with timeless style. Step inside to discover 3 spacious bedrooms, 2.5 baths, and an open-concept layout perfect for entertaining. The home features soaring ceilings, abundant natural light, and a seamless flow between living areas. A chef’s kitchen anchors the main level, complemented by a cozy family room and formal dining space. The main floor primary suite offers a private retreat with a spa-like bath, while additional bedrooms upstairs provide ample space for family or guests. The unfinished basement offers endless possibilities for expansion. Outside, enjoy the tranquility of your vinyl-sided exterior and expansive grounds ideal for gardening, recreation, or simply soaking in nature. The attached garage adds convenience, and the property’s Contemporary architecture ensures curb appeal that stands out. Located in desirable Chester, this home offers privacy without sacrificing proximity to commuter routes, schools, and amenities. Showings start at the Open House on Sunday 11/2 from 10am to 12pm! More pictures to come!

648 Haverhill Rd, Chester

157 Jenkins Farm Rd, Chester
$790,000
3 Beds ⋅ 3 Baths ⋅ 5062111 MLS
Welcome to the sought after Jenkin's Farm Neighborhood. This house has been meticulously maintained and updated by the original owners. You will love the open concept floor plan, high ceilings and stunning hardwood floors. The upgraded kitchen features granite countertops, SS appliances, plenty of counter and cabinet space and a large walk in pantry. There is a fabulous dining area over looking the private fenced in yard. The family room is open to the kitchen features a cozy gas fireplace and is drenched in sunlight. There is also a private home office with french doors and 1/2 bath on the main level. Upstairs you will be impressed by the large primary bedroom suite with full bath, double vanity, and huge walk in closet. Plus two other generous sized bedrooms, a full bath and the laundry room. Need more space? The finished basement offers plenty of options for a playroom, 2nd home office, craft room, home gym, etc. Lots of storage space, 2 car garage, back deck, fenced in yard and so much more! Don't Delay! Schedule your private showing today!

157 Jenkins Farm Rd, Chester

240 Sandown Rd, Chester
$775,000
3 Beds ⋅ 2 Baths ⋅ 5092423 MLS
Welcome to a truly prized piece of land, home to the cherished Dillon Old Farm Nursery for 42 years. Set peacefully back from the road on over 5 acres of lush, wonderfully maintained grounds, this charming Cape-style home offers private country living with exceptional modern updates and town convenience. The turn-key property features a traditional Cape layout boasting 3 bedrooms, 2 full bathrooms, and gleaming hardwood floors through much of the main areas. On the first level, a bright kitchen flows seamlessly into the dining room, while a flexible first-floor bedroom with an adjacent full bath can easily serve as your dedicated home office. Upstairs, you will find two additional spacious bedrooms with abundant storage, a second full bathroom, and a convenient laundry area. Major recent exterior and mechanical updates provide ultimate peace of mind. The home features newer windows, siding, and gutters for low-maintenance living, alongside a newer furnace, and well tank, along with fresh interior paint throughout much of the home. Outside, a maintenance-free deck seamlessly connects the house to an updated, detached 2-car garage that comes complete with new garage doors and pull-down stairs leading to ample overhead storage. This sprawling acreage offers a beautiful, private canvas to harbor your inner desire for outdoor hobbies, gardening, or an expanded yard. Enjoy the best of both worlds with a serene setting that is still conveniently located near the center of town, providing access to Route 101. Don’t miss your chance to own this rare blend of acreage, updates, and local history.

240 Sandown Rd, Chester

71 Deerwood Holw, Chester
$765,000
4 Beds ⋅ 4 Baths ⋅ 5079925 MLS
Tucked at the end of a quiet cul-de-sac, and one of just two homes in the enclave, this beautifully updated 4-bedroom, 4-bath home offers a rare combination of privacy, space, and flexibility—set on over 2 acres. Extensively improved by the current owners, this home delivers true peace of mind with major recent upgrades including a new roof, new garage doors, updated lighting, new flooring, fresh interior paint, and a new water filtration system—allowing you to move in and enjoy from day one. The layout is thoughtfully designed for today’s lifestyle. A first-floor bedroom offers ideal flexibility for guests, multi-generational living, or a dedicated home office. The main living area is anchored by a wood-burning fireplace, adding warmth and character to the space. The primary suite features its own private bath with radiant heated flooring, creating a comfortable retreat at the end of the day. A standout feature is the expansive bonus space with a ¾ bath, offering excellent potential for an in-law setup, extended living space, or future ADU possibilities (buyer to perform due diligence). Looking for even more room to grow? The walk-up third-floor attic presents a rare opportunity to easily expand—perfect for a home gym, media room, or additional living space. Outside, enjoy the serenity of your private 2+ acre setting, ideal for entertaining or relaxing—complete with a pool table that stays, making this home as fun as it is functional. With significant upgrades already completed, a flexible floor plan, and room to expand, this home offers both immediate comfort and long-term value. Exterior photo digitally enhanced in hopes of Spring!

71 Deerwood Holw, Chester

21 Penacook Rd, Chester
$762,500
3 Beds ⋅ 3 Baths ⋅ 5057903 MLS
Step into this spacious and beautifully maintained Contemporary Ranch, built in 2001, offering comfort, style, and room to grow. With 10 well-appointed rooms, this home features 3 bedrooms and 3 full baths, perfectly designed for both everyday living and entertaining. The main level boasts an inviting layout with gleaming hardwood floors in select areas, a cozy family room with vaulted ceiling, and a formal dining room ideal for hosting. The eat-in kitchen opens to a bright sunroom via sliding doors, seamlessly extending your living space into the private backyard. The primary bedroom is a true retreat, complete with a walk-in closet, luxurious jacuzzi tub, separate shower, and a linen closet. Two additional bedrooms on the first floor offer ample space and flexibility, plus separate laundry room. Upstairs, a finished walk-up attic provides a versatile bonus room, full bath, and extra space that could be used as a game room, office, or additional storage. The finished basement includes a walk-out to the backyard and offers even more room to relax, entertain, or create the perfect in-law or guest suite.With a thoughtful layout and generous space inside and out, this home is a rare find — ready to welcome its next owners. This home has Central A/C, Central Vac, Irrigation system, and hook up for portable generator, attached 2 car garage on 2.64 acres. OPEN HOUSE Sunday 10/12 11:00 - 12:30

21 Penacook Rd, Chester

173 Jenkins Farm Rd, Chester
$760,000
3 Beds ⋅ 3 Baths ⋅ 5079403 MLS
Welcome home to this beautifully maintained Colonial in the highly desirable Jenkins Farm neighborhood of Chester, NH. Lovingly cared for and very lightly lived in, this home shines with pride of ownership and offers the perfect blend of comfort, space, and charm. Step inside to a bright, open-concept first floor designed for easy everyday living and effortless entertaining. The spacious sunken great room is the heart of the home, featuring a cozy fireplace and walls of windows that fill the space with natural light. Just off the great room, a welcoming dining nook creates the perfect spot for morning coffee or casual family meals. The thoughtfully designed first floor also includes a convenient laundry area, a stylish powder room, and seamless flow throughout the living spaces. Stay comfortable year-round with central air conditioning.Upstairs, you’ll find three generously sized bedrooms including a relaxing primary suite, along with two full bathrooms to accommodate family and guests with ease. Need more space? The finished walk-out basement offers fantastic bonus living space, ideal for a family room, home office, playroom, or gym. Outside, enjoy the beautiful lot and peaceful setting from your private back deck, perfect for summer grilling or quiet evenings overlooking the yard. The two-car garage provides convenience and additional storage. Located in a lovely neighborhood known for its charm and community feel, this home offers the tranquility of Chester while remaining close to commuting routes, shopping, and local amenities. Sweet, welcoming, and move-in ready, this is the kind of home that just feels right the moment you walk in. Come see why life in Jenkins Farm is so special. Your next chapter starts here. Showings start at the OPEN HOUSE 3-21 and 3-22 from 1-3pm!

173 Jenkins Farm Rd, Chester

392 Fremont Rd, Chester
$754,000
3 Beds ⋅ 3 Baths ⋅ 5064008 MLS
New construction colonial home to be completed by mid-to end of November! Enter through the mudroom from the garage where you will find your 1st floor laundry and a 1/2 bathroom. The kitchen, a chef's dream, is equipped with a center island, beautiful countertops and new appliances that will make cooking a pleasure. There is an eat-in area with a sliding glass door to the back deck, a pantry, a dining room or office area, and the living room for entertaining or relaxing. Second floor primary suite features 2 walk-in closets, another small closet, and a beautifully tiled en-suite bath with a dual vanity. Rounding of the second level are two other bedrooms, a full bath, AND a generous size bonus room. The Central air, hardwood floors on the first floor and two-car garage add convenience to everyday living. Realtor is related to seller.

392 Fremont Rd, Chester

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