Chester Homes with Chester School District School district

Welcome to Chester, New Hampshire – a charming town nestled in the heart of Rockingham County. Known for its picturesque landscapes and tight-knit community, Chester combines the tranquility of rural living with convenient access to urban amenities. Just a short drive from the bustling cities of Manchester and Nashua, residents enjoy the perfect balance of serene country life and vibrant city culture.

Chester is not only celebrated for its natural beauty but also for its commitment to education. The Chester School District is known for its dedication to fostering a nurturing and enriching environment for students. Families residing in this area can take pride in the quality education their children receive, with a focus on academic excellence, creative expression, and character development. The district's strong emphasis on community involvement ensures that parents and guardians can actively participate in their children's educational journey.

The real estate market in Chester offers a diverse range of homes, from charming historic houses to modern new builds, catering to various lifestyles and budgets. With spacious yards and scenic views, these properties provide the perfect backdrop for family life, outdoor activities, and entertaining friends. Whether you're looking for a cozy cottage or a sprawling family home, Chester has something to suit your needs.

As you explore the possibilities in Chester, you'll discover a welcoming community filled with friendly faces, local events, and a rich history that makes this town a truly special place to call home. Come experience the warmth of Chester, where every day feels like a breath of fresh air!

Newest Chester Homes with Chester School District School district

$749,000

4 Beds ⋅ 2 Baths ⋅ 5101760 MLS

Discover the perfect blend of rustic elegance and modern versatility at 34 Edwards Mill Road. Set on 3.89 expansive acres in the scenic countryside of Chester, NH, this stunning log home offers a serene lifestyle for any stage of life. Are you looking for a natural playground where you can explore the woods and the soothing waters of Towle Brook, or wanting a peaceful New Hampshire retreat with single-level living potential, this property delivers. The spacious interior has been thoughtfully maintained with fresh paint, featuring 9 spacious rooms including 4 bedrooms and 2 full bathrooms. The home’s flexible layout includes a first floor primary bedroom suite that opens directly into a gorgeous huge sunroom. For those prioritizing convenience, the first-floor separate laundry room facilitates true single-level living options. Recent updates ensure peace of mind, including log maintenance, new gutters, and freshly seal-coated driveway. Outdoor enthusiasts and hobbyists will fall in love with the substantial detached 3-car garage which features a brand-new roof, a convenient drive-through bay with heat and water access. Above, an enormous unfinished space presents incredible potential for a studio, storage, or an accessory dwelling unit (ADU), subject to approvals. Outside, the enormous 50 ft. deck provides the ultimate spot for hosting gatherings or simply relaxing to the sounds of the brook winding through your private acreage. Experience total privacy without sacrificing accessibility; this retreat is located just 25 minutes from the Massachusetts border and approximately one hour from the heart of Boston. This home has been lovingly cared for and is ready for its next chapter. Schedule your private tour today to experience the charm & serenity of this stunning Chester retreat. You won't want to leave.

34 Edwards Mill Rd, Chester

$850,000

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

$599,000

4 Beds ⋅ 2 Baths ⋅ 5096954 MLS

DON'T MISS THIS RARE OPPORTUNITY! One level living / Multigenerational opportunity. Discover this hard-to-find Ranch-style home set on two beautiful, level acres with exceptional backyard privacy in the heart of Chester's highly sought-after equestrian community. Properties like this don't come along often! This spacious 4-bedroom, 2-bath home offers desirable southern exposure across the backyard, creating the perfect setting to relax on the deck or porch while enjoying stunning sunsets. Inside, you'll find a large living room featuring a classic brick-hearth wood-burning fireplace and expansive hardwood floors that add warmth and timeless appeal. The main level includes three generously sized bedrooms with hardwood flooring, a full bath, and the convenience of first-floor laundry. The kitchen is well-appointed with stainless steel appliances, granite countertops, two pantry cabinets, and stylish recessed and pendant lighting. A bonus family room leads to the attached two-car garage, while the private primary suite above the garage features a sitting area, creating the perfect retreat at the end of the day. The full basement offers excellent potential for additional finished living space, giving you room to grow. Outside, the expansive level lot provides endless possibilities for entertaining, gardening, or enjoying the peaceful surroundings. The pool will require a new liner and possibly a new filter. ENTS & BUYERS to do their own Due Diligence to verify all listing information. Room sizes are for reference only; not guaranteed.

224 Haverhill Rd, Chester

$510,000

3 Beds ⋅ 2 Baths ⋅ 5096706 MLS

STAY-CATION LIVING IS CALLING. Nestled on a gorgeous, private, flat acre in Chester, this home delivers the outdoor lifestyle you've been dreaming of. Pull into the paved driveway and you'll already see it - the lush landscaping, the natural shade, and a backyard that's pure paradise. Three sheds plus a detached garage with partially finished bonus space give you room for all your gear and then some. Step inside through the foyer and you're greeted by warm wood floors and natural light throughout. The open concept kitchen features an island, updated cabinets, and a gas range - ideal for cooking after a long day outside. It opens to a cozy family room with a wood fireplace, one of TWO fireplaces in the home. Heat with propane, wood or electric baseboard. The half bath and laundry are conveniently tucked on the main level. Upstairs, the living room and dining area offer flexible everyday space, and the top floor holds the primary suite with a walk-in closet, a second bedroom with its own large closet, and a completely renovated full bath for both bedrooms to share. The middle floor is designed for a three-bedroom configuration — easy to convert back. Now for the MAIN EVENT: the backyard. Above-ground pool. Hot tub. Garden space. Deck. This is where summers happen. NEW SEPTIC & LEACH FIELD and 2-year-old heating system mean the big-ticket items are already done. Pinkerton Academy district. Book your tour today!

111 Shepard Home Rd, Chester

$825,000

3 Beds ⋅ 3 Baths ⋅ 5096334 MLS

The Eagle Farmhouse blends a classic colonial layout with a fresh, modern exterior. Step inside and you'll love the spacious open-concept design, perfect for both everyday living and entertaining. The kitchen features beautiful quartz countertops, ample cabinetry, and a seamless flow into the main living areas. Conveniently located off the garage, the mudroom provides the perfect drop zone for coats, shoes, and everyday essentials. A versatile den offers an ideal space for a home office, playroom, or guest area, while the inviting family room provides plenty of room to relax and gather with family and friends. Thoughtfully designed with comfort and functionality in mind. The second floor offers two spacious bedrooms with walk-in closets, a dedicated laundry room, a full bath, and a spacious primary with en suite with a lovely tiled walk-in shower designed to satisfy even the most discerning homeowner. The full basement could be finished later for future additional living space if desired. Pet friendly and no age restrictions. Come and see what this charming community of 8 detached condos in desirable Chester, NH has to offer. Last lot left - do not miss out! Home should be ready late Summer/early Fall.

Lot 2 Lot 2 Robin Way Unit 2, Chester

$825,000

3 Beds ⋅ 3 Baths ⋅ 5095953 MLS

Lot 2 Lot 2 Robin Way Unit 2, Chester

$432,500

2 Beds ⋅ 3 Baths ⋅ 5092343 MLS

You pull up to a quiet cul-de-sac, the noise of the world already fading behind you. A COVERED PORCH waits at the front door, the kind you actually use. Step inside and you'll know: this is the one. Nestled in Chester's Shaker Heights Estates, this meticulous MOVE-IN READY townhouse checks every box and then some. Pride of ownership shines through every room. The open main level welcomes you with gleaming hardwood floors and NATURAL LIGHT pouring in from every angle. The eat-in kitchen, a generous 17x15, features stainless steel appliances and flows right into the dining area, making everyday meals and weekend entertaining equally effortless. The living room is HUGE at 24x16 with a private DECK. Step outside, breathe in the wooded views, and make it your morning coffee spot or evening wind-down zone. A half bath and FIRST-FLOOR LAUNDRY round out the main level. Upstairs, two OVERSIZED bedrooms impress. The primary suite spans 24x16 with a private bath and walk-in closet, and the second bedroom at 20x18 has its own walk-in closet too. Everyone gets their own space here. Head downstairs to a FINISHED REC ROOM with daylight windows and walkout access - perfect for hobbies, a home gym, movie nights, or extra storage. The garage is OVERSIZED. Big enough to fit a truck and all the toys and tools you need. Out back, enjoy a patio in a wooded, country setting. HOA covers landscaping, water, sewer, plowing, and trash - truly low-maintenance living. Won't last!

15 Shaker Heights Ln, Chester

$579,900

2 Beds ⋅ 2 Baths ⋅ 5090733 MLS

This property presents a rare opportunity to own a large lot on desirable Chester St. Many options here: Update the house and create a huge farm property, build a new house and use the existing house as an ADU/cottage or other, subdivide into two lots with town approvals ** A beautiful country setting for this 16.4+/- acre farm with wooded areas to explore. ** This classic farmhouse offers 2 bedrooms, 2 baths, large eat-in kitchen, laminate, tile and soft wood floors. NEWER forced hot water boiler. Many farm features: Chicken coop, fenced in areas, 20x24 2-stall horse pole barn, a large barn that was moved to the property from another site in Chester. Peaceful, yet conveniently located, about 8.5 miles to Exit 4 I-93 and about 6.9 miles to Exit 2 Route 101. About Chester ** WASON POND is where residents can go to enjoy a quiet, natural place to walk, hike, cross-country ski, walk dogs, kayak, picnic, and swim. SCHOOLS: Consists of elementary & middle school, Chester Academy and the High School is Pinkerton Academy, in Derry. SCARECROWS: The town has been going scarecrow crazy for many years. Every October there are over 400 scarecrows placed all over town with a map showing the locations. The scarecrows will be on display through Oct. 31. HALLOWEEN NIGHT: Brings many visitors to Chester Street, where over the years Trick or Treat has become a must-see event. AGENTS & BUYERS to do their own Due Diligence to verify all listing information and verify options with town and necessary approvals to do so. Room sizes are for reference only; not guaranteed. *** House being sold in current condition and all items on the property to remain after month-to-month tenant leaves. House is tenant occupied and works from the house.

197 Chester St, Chester

$1,900,000

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

$899,900

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

$899,900

3 Beds ⋅ 3 Baths ⋅ 5084557 MLS

WOW Price Reduced ! 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

$799,900

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

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