Chester Homes with Colonial Style

Welcome to Chester, a charming city that beautifully blends history with modern living. Nestled in the heart of Pennsylvania, Chester is steeped in rich heritage, offering a vibrant community atmosphere that appeals to families and professionals alike. Known for its picturesque parks, bustling waterfront, and a variety of local shops and restaurants, Chester provides a unique lifestyle that balances urban convenience with suburban charm.

One of the standout features of Chester is its stunning collection of Colonial-style homes. These classic residences reflect the elegance and craftsmanship of a bygone era, characterized by their symmetrical facades, steep roofs, and inviting front porches. The Colonial architecture in Chester is not just a feast for the eyes; these homes are designed for comfort and functionality, making them ideal for family living.

Imagine coming home to a Colonial-style house with spacious interiors that boast hardwood floors, large windows that fill the rooms with natural light, and cozy fireplaces perfect for family gatherings. Many of these homes are situated in tree-lined neighborhoods, offering a sense of community and tranquility, while still being just a stone's throw away from Chester's vibrant downtown.

Whether you're a first-time homebuyer or looking to upgrade, Chester’s Colonial homes provide a timeless charm that never goes out of style. Embrace the opportunity to own a piece of history while enjoying all the modern amenities this remarkable city has to offer. Discover your dream home in Chester today, where classic elegance meets contemporary living!

Newest Chester Homes with Colonial Style

$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

$875,000

4 Beds ⋅ 3 Baths ⋅ 5097711 MLS

50K PRICE CUT! OPEN HOUSE | 11AM to 1PM | Sunday, July 26th, 2026 Welcome to 88 Crawford Road, a breathtaking residential haven nestled in the heart of Chester, New Hampshire. The Property This exquisite colonial estate seamlessly blends sophisticated architectural design with the tranquil beauty of its lush, private surroundings. Offering an expansive 3,675 square feet of meticulously crafted living space, the residence features 4 generously appointed bedrooms and 2.5 elegant bathrooms. From the grand, winding driveway to the majestic facade framed by mature trees, every detail of this home exudes luxury. The interior promises unparalleled comfort with expansive room layouts, high-end finishes, and an abundance of natural light pouring through magnificent feature windows. Location & Drivability Perfectly situated for those who demand both privacy and convenience, 88 Crawford Road offers an idyllic retreat without sacrificing accessibility. Located in the charming, historic town of Chester, you are mere minutes from top-rated local schools, pristine parks, and boutique community dining. For commuters, the property provides seamless access to major regional routes, putting the bustling commercial hubs of Manchester and Salem within easy driving distance, while offering a straightforward, scenic commute to downtown Boston and the gorgeous New Hampshire seacoast.

88 Crawford 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

$875,000

3 Beds ⋅ 3 Baths ⋅ 5095331 MLS

Collectors, auto or motorcycle enthusiasts or those needing an ADU take notice! Classic Country Colonial with Farmers Porch on lovely almost 6 acre lot; Sunroom with gas fireplace, cathedral ceiling and fan; Combination Dining/Kitchen with induction cooking stove and plenty of cabinets, fan and hardwood flooring; 1st floor Half bath with laundry; Formal Dining Room with wainscoting and hardwood floors; Spacious Living Room with hardwood floors; Primary bedroom with 3/4 bath, carpet, fan and 2 closets; 2nd Bedroom with fan and carpet; 3rd Bedroom with fan and carpet; Full Bath off hall; Heated 2 Car Attached Garage with storage above; Detached 3+ Car 2 story Garage with large bay doors, rear garage door and unfinished 2nd level for ADU potential! The detached garage footings will support a lift if desired! This one owner home has central air conditioning and extra space for expansion or storage.

15 Town Farm Rd, Chester

$425,000

4 Beds ⋅ 2 Baths ⋅ 5092775 MLS

Bank on Market due to buyer financing, this will go quickly! Investors, flippers and DIY enthusiasts, here is your opportunity to bring this magnificent Federal Colonial back to life! Located in picturesque Chester and built in 1795, this home offers over 3500 square feet of historic charm. Fireplaces adorn many of the rooms, and you’ll find unique features such as built-in cabinets and more. The first floor offers many layout possibilities, including multiple rooms that could serve as a dining room, living room, office, or bedroom. Upstairs are spacious bedrooms. Much of the home has wide pine flooring, and other attractive historic features. The wood siding is in good shape and most windows are newer as well. Situated on over 4 acres, the property features a large, level yard with garden areas. This home needs a full renovation, and the buyer is responsible for performing their own due diligence on all repairs. Property is being sold as-is, cash only.

55 Chester St, Chester

$600,000

3 Beds ⋅ 2 Baths ⋅ 5092425 MLS

If you're looking for a tranquil, move-in-ready 3-bedroom home nestled on 3.77 wooded acres, your search is over! Enjoy the peaceful surroundings from the brand-new 12' x 16' deck—the perfect spot to relax with a book and take in nature. This beautifully remodeled home offers worry-free living with a new roof, new windows, a stunning new kitchen featuring leathered granite countertops, soft-close cabinetry, and stainless steel appliances, plus two completely renovated bathrooms. Thoughtfully updated throughout, this property combines modern comforts with the privacy and serenity of a wooded setting. Don't miss the opportunity to own this turnkey retreat that feels miles away from it all while still providing the conveniences of home. Agent Interest

51 Halls Village Rd, Chester

$210,000

4 Beds ⋅ 2 Baths ⋅ 73520586 MLS

Colonial style home featuring 8 rooms, 4 bedrooms and 2 bathrooms located on 6+ acre lot.

1 Crane Rd, 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

$264,900

3 Beds ⋅ 2 Baths ⋅ 73428417 MLS

Welcome to this historic Colonial home nestled in the center of Chester, offering charm and modern potential. Featuring 6 spacious rooms, including 3 generous bedrooms and 1.5 bathrooms, this home is ideal for Living, investors, or those seeking an Airbnb rental opportunity. Inside, enjoy the warmth of beautiful wood floors throughout most of the home, a large kitchen with ample counter and cabinet space, and closets galore for all your storage needs. Additional features include a spacious three-season front porch that’s surrounded by natural light accented by a beautiful wood ceiling, vinyl windows, an attached 1-car garage, and a storage shed — all situated on a 0.36-acre lot. Located along the scenic Westfield River, this property is a haven for outdoor lovers, with nearby hiking and riding trails, and is just a short drive to Jacobs Pillow, Tanglewood, Lee Outlets, and only 30 minutes to Westfield or the Berkshires.

254 Route 20, Chester

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