Hillsborough Homes with Guest Quarters Exterior Features

Welcome to Hillsborough County, New Hampshire, where picturesque landscapes and a vibrant community come together to create an idyllic living environment. Nestled in the heart of New England, Hillsborough boasts charming small towns, rich history, and stunning natural beauty. With its rolling hills, serene lakes, and lush forests, outdoor enthusiasts will find endless opportunities for hiking, fishing, and exploring the great outdoors.

Hillsborough County is not just about breathtaking scenery; it’s also home to a thriving community with excellent schools, local shops, and a variety of dining options. Whether you’re looking for a quiet retreat or a place to raise a family, this county offers a warm and welcoming atmosphere that makes everyone feel at home.

One of the standout features of many homes in this region is the presence of guest quarters. Imagine having a spacious, fully-equipped suite for visiting family and friends, or even a private space for an office or creative studio. Homes with guest quarters in Hillsborough County are designed with both comfort and convenience in mind, providing a perfect blend of privacy and hospitality. These exterior features often include separate entrances, cozy living spaces, and well-appointed amenities, ensuring your guests feel right at home.

As you explore the real estate options in Hillsborough County, you’ll discover a variety of properties that embody the spirit of New Hampshire living. From charming cottages to expansive family homes, each residence offers a unique opportunity to enjoy the beauty and warmth of this stunning region. Come and experience the charm of Hillsborough County – your dream home awaits!

Newest Hillsborough Homes with Guest Quarters Exterior Features

$285,000

1 Beds ⋅ 1 Baths ⋅ 5106610 MLS

MOOSE BROOK RETREAT WITH DETACHED STUDIO ! Downstairs features a welcoming kitchen with convenient stool-style seating that opens directly into the living room, creating an inviting and functional space for everyday living and entertaining. Step out onto the back deck to enjoy peaceful views of the flowing waters of Moose Brook. Walk-up stairs lead you to the spacious bedroom with picturesque views overlooking the brook. The property offers plenty of storage with two sheds and a canvas tent, providing ample room for outdoor equipment, hobbies, and recreational gear. A sturdy iron-railed walking bridge leads to a dedicated campfire area, creating the perfect setting for relaxing evenings by the brook. A detached studio adds even more versatility and endless possibilities for use as a creative space, office, guest area, or potential ADU. With the simple addition of a kitchenette, the studio could be transformed into a comfortable accessory dwelling unit. A unique opportunity to enjoy the beauty and tranquility of Moose Brook while offering flexible spaces, abundant storage, and room to make the property your own.

164 Bennington Rd, Hancock

$4,000,000

6 Beds ⋅ 8 Baths ⋅ 5106236 MLS

Perched high above the rolling hills of New Boston, where panoramic mountain views stretch for miles and privacy is absolute, lies one of New Hampshire's most extraordinary and coveted estates. A true legacy property, this architectural masterpiece is tucked away on 9 pristine acres, offering an unparalleled blend of luxury, serenity, and resort style living. Spanning more than 15,000 square feet, with an additional 5,000 square feet of newly completed living space finished this year, this remarkable residence was designed without compromise. Every space has been thoughtfully curated to deliver an exceptional living experience, whether hosting elegant gatherings or enjoying peaceful moments surrounded by nature. The estate features 6 luxurious bedrooms, 8 beautifully appointed bathrooms, 3 full kitchens, multiple laundry rooms, and an impressive 8 bay garage, effortlessly accommodating multi-generational living, extended guests, or grand-scale entertaining. Resort caliber amenities rival those of a five star retreat. Enjoy both indoor and outdoor heated saltwater pools, a stunning newly constructed pool house, an expansive entertainment lounge, a home gym, a private movie theater, and a spa-inspired sauna with a walk-in shower adjoining the indoor pool creating your own year-round wellness retreat. From sunrise over the mountains to evenings spent under the stars, every inch of this estate was crafted to inspire. Adding to its exceptional versatility is a bonus townhouse-style guest house, complete with additional bedrooms and bathrooms, its own private parking, a separate entrance, and a private yard offering an ideal space for extended family, guests, or additional living accommodations. This is truly a must-see in person to fully appreciate the magnificent craftsmanship, scale, privacy, and what this extraordinary estate has to offer. Broker interest.

104 Foxberry Dr, New Boston

$4,750,000

11 Beds ⋅ 7 Baths ⋅ 5106118 MLS

Located in the heart of the Monadnock Region, reknown for its cultural offerings, close knit communities, protected landscapes and recreational amenities including Crotched Mountain Ski area in town and nearby Crotched Mountain Golf Club. An impressive farm since the early 1800's, Pierce Hill Farm was transformed to a gentleman's estate in 1909. . Its over 306 acres feature 40 acres +/- of hayfields managed by a local farmer, cut stone walls built by Irish masons, gravel carriage roads, walking paths, a private pond, and mountain views. The three story main house has been conscientiously maintained and enjoys lovely grounds with gardens, broad lawn, in-ground pool with patio, tennis court and beautiful views. The first floor boasts large, gracious rooms for entertaining or family gathering. The second floor had a primary suite, two guest bedrooms and four small bedrooms in the kitchen wing. On the third floor are four large bedrooms and two more baths. Also dating from 1909 are the two bedroom, two bath guest house, the five bedroom, two bath farm manager's residence, and the former milk house, now a two bedroom one bath residence. An additional two bedroom 1 bath residence was built in 1961. All the houses enjoy a screened porch with a lovely, private outlook. Farm buildings incude the old dairy barn with slate roof, full hayloft, 2 bay vehicle storage, 4 animal pens and water hydrant. Its attached ell has a tractor bay, box stalls,hayloft, and more animal pens below. The horse barn was built as a showplace with a vaulted two story entry. Clerestory windows light the hayloft below the slate roof. The main aisle is floored with wood bricks and the stall walls have been removed, creating a light open space. The main floor also has a heated workshop, old plumbing, and storage rooms. A full, walkout lower level is used for storage. Additional outbuidings include a garden house, sap house, equipment barn, and old ice house now used for storage.

92,94,96,98,100 Pierce Hill, Bennington

$3,350,000

5 Beds ⋅ 4 Baths ⋅ 5105366 MLS

Originally the Oliver Whiting Homestead, the largest dairy farm in Wilton, in 1868 it became the county farm. Since the early 1900's, the property has been a gentleman's estate. There are so many amenities for active country living! Its 136.5 acres include well maintained open fields, broad lawns with established gardens,former HarTru tennis court, three ponds - two stocked with trout and one for swimming. Sweeping views from Temple Mt. to North and South Pack Monadnock to the Lyndeborough mountains. Long frontage on Whiting Brook. A conservation easement protects 127.5 acres. The gracious center hall entry of the Brick colonial opens left to a front to back living room with two fireplaces which accesses a large screened porch. Rear is a library/study. Right is a fireplaced dining/sitting room, eat-in kitchen open to a sunroom, a family room with fireplace and woodstove flue, laundry/store room and shower bath. Upstairs are four corner bedrooms, three with fireplaces, enclosed porch and two baths. A primary suite is in the ell, accessed by a back staircase. An historic barn has been converted to a two bedroom guesthouse on its first floor. Its second level is outfitted as an entertainment area with lounge and pool table. A stairway leads to a third level cupola with hatch to a roof deck for mountain and star viewing. Outbuildings include a 9 bay carriage barn with full loft and a summer studio, three stall horse barn with water, and massive three story barn 150' x 60". The barn's lowest level has 8 cement floored garage bays with overhead doors. After 50+ years of enjoyment, the current family is looking for the next stewards of this epitome of a country estate. Wilton is the gateway to the recreational, cultural and scenic amenities of the Monadnock Region. Its home to Waldorf Schools, a movie theater, Andy's Summer Playhouse, Frye's Measure Mill and many protected forests with public trails. Its 1 1/2 hrs to Boston and 40 mins to Manchester airports.

37 Old County Farm Rd, Wilton

$2,290,000

7 Beds ⋅ 7 Baths ⋅ 5104767 MLS

Exceptional Multi Generational Living. This exceptional reproduction modern farmhouse, built in 2014 offers a flexible floor plan, sophisticated finishes, and an extraordinary Carriage House added in 2017, creating an unmatched opportunity for multi-generational living, extended family, guests, or simply those who desire exceptional space and versatility. MAIN RESIDENCE: The 5,189 sq. ft. blends timeless farmhouse character with modern luxury. At its center is a spectacular Chef’s Kitchen, featuring Viking appliances, wine refrigerator, beautiful white inset cabinetry, and granite surfaces. The kitchen flows naturally into the home's gathering spaces and expansive outdoor living areas. One of the property's most impressive features is the 1,520 sq. ft. OUTDOOR DECK and dining space, creating an extraordinary setting for large gatherings. AUDIO and media systems further enhance the home's entertaining capabilities. The walkout lower level adds more flexible living space, for a wine cellar, media room, home office, or private bar. The Primary Suite is a true retreat, complete with its own balcony and the rare luxury of two separate bathrooms and dressing rooms. There is a huge game room on the 1st floor that has access to deck, and upstairs there are 3-4 more bedrooms. Then there is the CARRIAGE HOUSE: Approx. 2,662 sq. ft., it features radiant-heated floors, a 5+ car garage, custom party-inspired cabinetry and finishes, and a heated dog grooming/shower room. Above the garage are two separate in-law apartments, each offering additional private living space and balconies. Accessibility features, including provisions for a chairlift. CAR ENTHUSIASTS, collectors,or anyone needing serious garage space, the Carriage House is an extraordinary bonus. And the location is equally compelling: top-rated schools with the convenience of being able to walk or drive to school, along with easy access to everyday amenities. Come experience the possibilities firsthand. VISit today

241 Wallace Rd, Bedford

$879,000

3 Beds ⋅ 3 Baths ⋅ 5104324 MLS

This sun-drenched contemporary is a rare private retreat designed for luxury living, comfort, and effortless entertaining. Tucked away on a beautifully landscaped lot yet just minutes from shopping, outlets, and major routes, this exceptional three-bedroom home offers resort-style living inside and out. At the heart of the home is a spectacular chef’s kitchen featuring an expansive granite island and countertops, oversized Thermador refrigerator/freezer, double ovens, two gas cooktops, two sinks, and premium appliances. The open-concept dining area flows into an elegant English-style bar and dramatic cathedral-ceiling living room with a solid stone fireplace. Six skylights fill the home with natural light. Upstairs, the spacious primary suite features a walk-in closet, full bath, and a cozy library that provides the perfect reading nook. There are two additional generously sized bedrooms with vaulted ceilings, and another full bath completes the second floor. The finished lower level offers flexible space for a family room, gym, home office, hobby room, or recreation area. Step outside and discover your own private resort! The heated in-ground Gunite pool with natural stone decking is complemented by a tiki bar, hot tub, expansive deck, greenhouse, and spectacular landscaping. The tropical cabana is a destination of its own, complete with living, dining, kitchen, sleeping space, and wood stove that's ideal for guests or poolside entertaining. Enjoy continuous color from spring through fall with Japanese maple, lilacs, azaleas, rhododendrons, roses, hydrangeas, lilies, peonies, hostas, blueberry bushes, and more. Where can you find a home like this? This is a rare gem, and you’ve found it here! Two-car garage includes storage bins, multi-zone heating system 2021, new roof 2022, Generac 17 kW generator, Central AC.

6 Haines Ter, Merrimack

$1,250,000

4 Beds ⋅ 4 Baths ⋅ 5103192 MLS

What an opportunity! Take a look at this handsome 2016 custom colonial, 3+ bdrms and 4 baths with a Guest Suite over the garage, plus a separate self-contained 2023 ADU Cape with 2 bdrms and 1.5 baths. This one of a kind property sits on 4+ acres of land just 3 minutes from the Bedford line and 20 min. to Manchester and highways. Some of the many custom features include a wraparound covered porch, 1st floor Office, Guest Suite with kitchenette, large Rec. Room in the walkout/daylight Lower Level, Mudroom with laundry area and 3/4 bath, and a walk-up Attic roughed in for plumbing, electrical and heat/AC. The Primary Suite features a large walk-in closet, 3/4 bath with dual vanities and large shower. The Granite/Stainless Kitchen includes a terrific walk-in Pantry, Granite center island and opens to the Dining area, Deck and Living Room. Being only 10 years old the systems will last for years, and the high efficiency heat and central A/C features 3 zones for even distribution throughout the entire home. In addition to the terrific primary home is a separate 2023 Cape style ADU featuring 2 bedrooms and 1.5 baths, including a 1st floor bedroom and full bath plus a bedroom, small office and 1/2 bath on the 2nd floor. The ADU also contains a large, unfinished walkout/daylight basement with laundry and room for tons of storage. This ADU is designed for low maintenance and efficiency, with excellent insulation and a heat pump/AC system using 3 heads for distribution throughout the home. It currently rents for $2850/month plus utilities with a terrific rental history. Shared well, separate septic systems. There is plenty of parking for the ADU and it is sited away from the primary home with a treeline in between. If you want an income-producing property, have a large family or are needing to accommodate multi-generational living this could be the home for you! **CHECK THE TOUR URL FOR INTEGRATED FLOORPLANS WITH PHOTOS** SHOWINGS START AT THE OPEN HOUSE SAT. 8/8 1-4PM

325 Mccurdy Rd, New Boston

$1,100,000

4 Beds ⋅ 3 Baths ⋅ 5096525 MLS

Discover unparalleled privacy and natural beauty at this end-of-the-road private retreat, nestled within 313 conserved acres with sweeping south and east-facing views stretching all the way to the Boston skyline. This property offers a rare opportunity to own a significant piece of New England's pristine wilderness. Tucked into the southeast corner of this expansive domain is a charming 1936 four-bedroom, three-bath Cape-style home featuring warm, wide pine floors and walls, a fireplace, and windows that frame picturesque views. The ell of the cape is currently used as a studio apartment with one bedroom and one bath. Beyond the main residence, a second, passive solar home built in 2011 offers additional guest or caretaker accommodations. Both homes are equipped with automatic standby generators, ensuring comfort and peace of mind. Multiple outbuildings provide ample storage including room for six vehicles. 3.6 acres surrounding the residences are excluded from the conservation easement, providing private command over the immediate surroundings. The northern end of the property includes sections of Temple Mountain Ridge, Holt Mountain and the historic Wapack Trail, one of the Northeast’s oldest hiking trails, allowing seamless access to thousands of protected acres directly from the property. Located in the Monadnock Region in the SW corner of the state with easy access to Peterborough and the Manchester Boston Regional Airport and just 1.5 hours to downtown Boston.

48 & 56 Perkins Ln, Temple

$2,095,000

5 Beds ⋅ 7 Baths ⋅ 5096444 MLS

Perched atop a scenic hill and surrounded by 67± private acres, this extraordinary estate offers panoramic mountain views, unparalleled privacy, and spectacular sunsets overlooking Mt. Monadnock and Pat's Peak. Designed with exceptional craftsmanship and attention to detail, the main residence features soaring 10-foot ceilings, rich hardwood flooring, elegant crown molding, shadow box trim, and refined architectural details throughout. A dramatic two-story foyer welcomes you with a stunning backlit dome ceiling and leads to a handsome executive office complete with French doors and custom built-ins. The heart of the home is the magnificent great room, showcasing a floor-to-ceiling fieldstone fireplace and an expansive wall of glass framing breathtaking mountain vistas. Seamlessly connected, the gourmet chef's kitchen is designed for entertaining and everyday luxury, featuring premium stainless steel appliances including a Thermador Pro Range, oversized center island, granite countertops, coffee bar, and abundant custom cabinetry. The adjoining dining area captures the surrounding views, creating a truly memorable setting for gatherings.The first-floor primary suite serves as a private retreat with a spa-inspired bath featuring a jetted soaking tub, multi-jet steam shower, and heated tile flooring. Upstairs, a loft and balcony overlook the great room while continuing to showcase the home's remarkable views. The luxurious second-floor suite offers a gas fireplace, walk-in closet, oversized jetted tub, heated tile floors, and a beautifully appointed bath. Two additional bedrooms, a full bath, and a dedicated laundry room complete the second level.An attached in-law or au pair suite provides exceptional flexibility with a kitchenette, private living space, and ¾ bath. Additional amenities include an indoor exercise current pool, heated four-car attached garage, circular driveway, and a charming guest house with its own attached garage.

129 North Rd, Hillsborough

$3,000,000

6 Beds ⋅ 8 Baths ⋅ 5094918 MLS

A masterpiece of craftsmanship, design and multigenerational living, this extraordinary Bedford estate offers an unparalleled blend of timeless elegance, exceptional quality, and resort-style living. From the moment you arrive, the grand granite entry and impressive mahogany double doors set the tone for a residence where every detail has been thoughtfully curated. The dramatic foyer welcomes guests with a sweeping curved staircase and exquisite custom mahogany millwork, Birdseye maple flooring, Italian marble finishes, and designer architectural details are showcased throughout. The chef's kitchen is a work of art, featuring custom walnut cabinetry, premium appliances, expansive granite surfaces, coffee station, and multiple entertaining areas. The home's luxurious primary suite serves as a private retreat with cathedral ceilings, fireplace, spa inspired marble bath, custom dressing room, private beverage station, and outdoor access. Multiple guest suites, private balconies, dedicated office and recreation spaces, and a finished lower level provide exceptional flexibility for today's lifestyle. Private guest quarters above the attached garage, offering two bedrooms, a full bath, kitchenette, living area, and separate gathering spaces. Ideal for guests, an au pair, or multigenerational living, this thoughtfully designed wing provides comfort and privacy while remaining connected to the main residence. Designed for indoor outdoor living, the estate features a spectacular pool and spa setting, extensive brick and granite terraces, outdoor entertaining areas, covered gathering spaces, and beautifully landscaped grounds that create a true private resort experience. Additional highlights include a detached three car garage with a finished upper level with comfortable work or living space, Murphy bed and full bath. A rare offering where luxury, comfort, and craftsmanship converge, creating one of Bedford's most distinguished residences.

56 Oak Dr, Bedford

$625,000

4 Beds ⋅ 3 Baths ⋅ 5094839 MLS

Just steps from Cunningham Pond and surrounded by the natural beauty of New Hampshire’s trail country, this inviting four bedroom, 2½ bath home is ideal for families looking for warmth, comfort, and outdoor adventure. Outdoor enthusiasts will appreciate the direct access to some of the area’s most cherished trail systems, including Pack Monadnock and the Raymond Trail to Miller State Park. From peaceful pond walks to scenic hikes, the best of the New Hampshire lifestyle is right outside your door. Inside, the thoughtful layout offers excellent versatility. A convenient first-floor primary bedroom provides ease of access, while the upper level offers the option for a second primary suite with a spacious walk-in closet—ideal for multigenerational living or guests. At the heart of the home is an inviting kitchen featuring rich cherry cabinetry and leathered granite countertops, designed to connect seamlessly with the living spaces. The private backyard serves as a true retreat, featuring an expansive deck and a charming boardwalk that leads to a log cabin tucked among the trees. Additionally, a heated workshop, equipment shed, and an oversized two-bay garage provide exceptional space for projects and storage. Conveniently located near local schools and just minutes from downtown Peterborough, this special property offers a peaceful setting with easy access to shopping, dining, and community events.

138 Cunningham Pond Rd, Peterborough

$2,499,000

5 Beds ⋅ 4 Baths ⋅ 5079599 MLS

A truly exceptional EQUESTRIAN ESTATE set on 10+ picturesque acres in one of Southern New Hampshire’s most coveted locations—just minutes to the Mass border. This extraordinarily rare property offers the perfect blend of luxury living and premier horse facilities. Designed with the serious equestrian in mind, the property features 2 separate 12-STALL HORSE BARNS, one with an attached 180’ x 70’ INDOOR RIDING ARENA, complete with private viewing area and office space. The barn is thoughtfully appointed with tack and feed rooms, wash stalls, generous haylofts, and abundant storage. Acres of FENCED PADDOCKS provide ample turnout, complemented by a separate OUTDOOR RIDING RING. Additional adjoining land is available to expand the estate if desired. A separate 2-bedroom GUEST HOUSE includes a bath, kitchen, garage, and additional tack room or workshop space—ideal for trainers, extended family, or caretakers. The stunning 5+ BEDROOM main residence offers flexibility with two primary suite options—one on each floor—perfect for multigenerational living. Gorgeous hardwood flooring, multiple fireplaces, and an abundance of windows create warmth and natural light throughout. The expansive wraparound porch invites you to relax and take in serene views, while the sunroom provides a bright year-round retreat. Upstairs offers private, separated guest space for added comfort. Resort-style amenities elevate this remarkable property even further, including a HEATED GUNITE POOL, POOL HOUSE with bath and kitchenette, custom OUTDOOR KITCHEN, and a private TENNIS COURT. A rare opportunity to own a premier equestrian estate in Southern NH—where luxury, privacy, and world-class horse facilities come together in an unparalleled setting.

40-40a Pine Hill Rd, Hollis

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