Windham Homes with Colonial Style

Welcome to Windham, New Hampshire, a picturesque town nestled in the heart of Rockingham County. Known for its stunning landscapes, friendly community, and rich history, Windham is the perfect blend of small-town charm and modern convenience. With its rolling hills, serene lakes, and lush forests, residents enjoy a wealth of outdoor activities, from hiking and biking to fishing and boating. The town boasts excellent schools, making it an ideal location for families, while its proximity to major highways provides easy access to nearby cities like Manchester and Nashua.

One of the most enchanting features of Windham is its collection of Colonial-style homes. These timeless residences exude elegance and charm, often characterized by their symmetrical facades, gabled roofs, and classic colonial details. Many of these homes have been lovingly preserved, showcasing original features such as hardwood floors, intricate moldings, and spacious layouts that invite family gatherings and entertaining.

Living in a Colonial-style home in Windham means embracing a lifestyle steeped in tradition while enjoying modern amenities. These homes often come with generous yards, perfect for outdoor activities and summer barbecues, as well as proximity to Windham's vibrant community events and local amenities. Whether you're seeking a cozy retreat or a spacious family home, the Colonial properties in Windham offer a unique opportunity to experience the best of New England living.

Explore the charm of Windham and discover your dream Colonial home today!

Newest Windham Homes with Colonial Style

$899,000

4 Beds ⋅ 3 Baths ⋅ 5102139 MLS

Gracefully set on 2.67 private wooded acres in one of Windham's most desirable locations, this beautifully updated Colonial is a timeless blend of classic architecture, thoughtful design, and modern comfort. Offering 2,924 sqft of thoughtfully designed living space, this exceptional residence provides easy access to the Rail Trail, shopping, dining, and commuter routes. A two-story foyer welcomes you inside, where freshly painted interiors, hardwood flooring throughout much of the home, and abundant natural light create a warm yet sophisticated atmosphere. Elegant glass-pane doors open to the formal dining room, highlighted by a beautiful tray ceiling, while a second glass-pane door leads to one of two private studies, complete with a cozy propane fireplace. A second study and spacious bonus room offer endless flexibility for today's lifestyle. At the heart of the home, the beautifully appointed kitchen features granite countertops, a generous peninsula for gathering, and seamless flow into the adjoining living spaces. The inviting living room is anchored by a propane fireplace, creating a warm and welcoming atmosphere for everyday living and entertaining. Step outside to the brand-new deck overlooking the private wooded backyard, offering the perfect setting for outdoor dining, summer gatherings, or simply relaxing in the peaceful surroundings. The spacious primary suite is a true retreat, entered through elegant solid French doors and highlighted by a soaring vaulted ceiling and beautifully updated ensuite bath. Three additional generously sized bedrooms, updated bathrooms, first-floor laundry, mini-split systems, a whole-house fan, and an attached two-car garage provide comfort and convenience. Thoughtfully maintained with newer siding, new deck, furnace, fresh interior paint, and numerous updates throughout, this home offers peace of mind for years to come. Combining timeless Colonial charm, modern updates, and an exceptional Windham location.

20 Jackman Ridge Rd, Windham

$985,000

3 Beds ⋅ 3 Baths ⋅ 5101452 MLS

Some neighborhoods you find on Zillow. Castle Reach, you wait for. Homes in this community are rarely offered, making each opportunity truly special. Set along a scenic route near the orchards of Apple Acres Farm and the historic turrets of Searles Castle, this is a Windham location unlike any other. 35 Mockingbird Hill Road puts you in the heart of it. This sun-filled hip roof colonial sits on approximately one acre of beautifully landscaped grounds, with hardwood floors, crown molding, and French doors setting the tone from the front door. Designed with both function and entertaining in mind, the eat-in kitchen features a center island, wall oven, gas cooktop, breakfast nook, and a beverage bar with a built-in refrigerator, all opening to a generous deck that overlooks the private backyard. The vaulted family room with gas fireplace anchors the main level, while a dedicated home office and additional first-floor den offer exceptional flexibility for today’s lifestyle. Upstairs, the primary suite features a tiled bath with whirlpool tub. Thoughtfully designed features include central air, irrigation, and a high-ceiling walkout basement with plumbing in place for a future bath and direct access to a stone patio, offering exceptional flexibility and room to grow. A standout feature of Windham is its exceptional school system, consistently recognized for academic achievement and educational excellence. Beyond the community itself, the location offers convenient access to major roadways and local amenities. A short drive to I-93 provides easy connectivity to Boston and the surrounding region, while nearby destinations including Cobbetts Pond, Windham Country Club, and the town beach offer a variety of recreational opportunities. Rarely available in Castle Reach, this exceptional property offers the opportunity to experience the privacy, quality, and craftsmanship that define this sought-after community. *Showings begin Saturday at the Open House from 10:00 AM–12:30.

35 Mockingbird Hill Rd, Windham

$1,250,000

4 Beds ⋅ 3 Baths ⋅ 5101244 MLS

Experience elevated living in one of Windham’s premier neighborhoods. Situated in the highly sought-after Spruce Pond community, this beautifully designed home offers luxury features, exceptional living spaces, and a thoughtfully designed floor plan. Step inside to a grand two-story foyer flanked by a private home office and formal living room. That effortlessly flows into a oversized dining room, and convenient first-floor powder room. At the heart of the home, the gourmet kitchen is beautifully appointed with premium JennAir appliances, a large center island, abundant cabinetry, and an inviting eat-in area that opens seamlessly to the impressive family room featuring soaring vaulted ceilings, a stunning fireplace, and newly installed hardwood flooring. Step outside to the oversized composite deck, creating the perfect setting for outdoor entertaining with a large level backyard. Upstairs, retreat to the luxurious primary suite featuring an oversized bedroom, an expansive walk-in closet, and a spa-inspired bath with heated floors. Three additional generously sized bedrooms and a full bath complete the second level. The finished lower level offers exceptional flexibility with space ideal for a home theater, game room, fitness studio, playroom, guest retreat, or an additional home office, plus unfinished space ready for future expansion, storage, or customization. Designed with comfort and convenience in mind, additional premium features include a whole-house central vacuum system, 8-zone irrigation system, efficient 3-zone HVAC, security system, and exceptional storage throughout. Ideally located in one of Windham’s most desirable neighborhoods with top-rated schools, shopping, dining, and major commuter routes, 15 Northland offers the perfect blend of luxury, comfort, and everyday convenience. Come visit our Open House on 07/25 & 07/26 from 1:30PM-3PM.

15 Northland Rd, Windham

$1,849,000

6 Beds ⋅ 5 Baths ⋅ 73553289 MLS

Set on nearly five acres of complete privacy, this exceptional estate offering over 5,800 sq ft with a separate guest residence offering over 2,400 sq fti s a rare offering—where scale, versatility, and lifestyle come together in a way seldom found. What sets this property apart is the seamless blend of luxury living and purpose-driven spaces, thoughtfully designed to adapt to the way you live today. The main residence offers four spacious bedrooms, an expansive dining room, and a beautifully scaled family room, all connected by a flowing, open layout. A private third-floor office provides a quiet, tucked-away workspace—ideal for productivity and privacy. At the heart of the home, a custom theatre opens directly to the expansive deck, creating a one-of-a-kind indoor-outdoor entertaining experience. Paired with a dedicated bar and game area, this space delivers the feel of a private club within your own home—perfectly designed for gathering and entertaining. The primary suite isa true retreat—generous in scale with a fireplace, a beautifully updated spa-inspired bath, and its own private deck overlooking the grounds. The secondary residence elevates this property into a true estate compound—far beyond a traditional guest house. Alongside a two-car garage, fitness area, sauna, and full bath, it features a bright, fully independent living area offering complete separation and flexibility for extended family, guests, or live-in support. Outdoors, the property unfolds into a private sanctuary, with an in-ground pool surrounded by lush, open grounds that enhance the home’s sense of privacy and scale. This is more than a home—it’s a property designed for how people truly want to live today: offering privacy, space, and flexibility in a rare estate setting.

117 Castle Hill Rd, Windham

$790,000

3 Beds ⋅ 3 Baths ⋅ 5100937 MLS

OFFER DEADLINE TUESDAY, JULY 28TH AT NOON. Welcome home to 4 Longmeadow Rd, ideally situated in one of Windham's most desirable neighborhoods! This colonial offers 2,904 square feet of finished living space, including a versatile finished basement, all set on a beautifully private 1.26-acre lot. The smart layout offers a functional flow, with all three bedrooms conveniently located on the second floor and a half bath on the main level for guests. Step outside to your own screened-in deck, the perfect spot for morning coffee or evening relaxation overlooking the private, tree-lined yard. Move right in and make it your own with cosmetic updates over time, instead of paying for someone else's design decisions. All in a fantastic location close to top-rated schools, shopping, and easy highway access. Homes in this neighborhood don't last, schedule your showing today!

4 Longmeadow Rd, Windham

$800,000

4 Beds ⋅ 4 Baths ⋅ 5100902 MLS

Windham checks every box and 29 Harris Road makes it easy to move right in before fall! Situated on over an acre just five minutes from Route 93 and a short drive to Tuscan Village, the Rail Trail, and tax-free shopping, this 4-bedroom colonial offers the kind of location that you've been looking for. The updated kitchen anchors the main level with a vaulted ceiling, custom cabinetry, granite counters, stainless appliances, and a dining area warmed by a brick fireplace. The primary suite is conveniently on the first level with laundry and access to the back deck. There are hardwood floors throughout and central AC keeps things comfortable inside all summer long. The 3 additional bedrooms upstairs are oversized and feature tons of closet space. The finished walkout basement with heating, AC, and a half bath is where the flexibility really opens up - use it as a family room, a home office suite, an in-law setup, or a fifth bedroom. The configuration adapts to however you want to live. Outside you'll enjoy the three-car garage, a sprawling fenced yard, and a Tesla Energy Storage System that's already doing the work. You won't want to miss this opportunity!

29 Harris Rd, Windham

$649,000

3 Beds ⋅ 2 Baths ⋅ 5100164 MLS

Welcome to year round tranquility in desirable Windham! Built in 2018, this beautifully maintained 3 bedroom, 2 full bath home offers the perfect blend of modern style and relaxed living with deeded water access to Cobbetts Pond. The light and bright open-concept floor plan features stunning dark hardwood floors throughout, creating warmth and elegance in every room. The kitchen shines with quartz countertops, stainless steel appliances, and seamless flow into the living and dining areas, making entertaining effortless. A spacious dining area, first-floor bedroom or office, and a full bath complete the main level and provide flexibility for guests or remote work. Upstairs, the spacious primary bedroom offers a vaulted ceiling, oversized window seat, abundant natural light, and generous closet space. A second bedroom, convenient second floor laundry area, and an additional full bath complete the upper level. Enjoy peace of mind with the recently added Generac standby generator. Ideally located just minutes from Route 93, commuting is easy while shopping, restaurants, and everyday conveniences are all close by. Experience the best of Windham living with modern comfort and the recreational lifestyle that comes with deeded access to beautiful Cobbetts Pond.

12 Grove St, Windham

$1,249,900

4 Beds ⋅ 4 Baths ⋅ 5099815 MLS

PRICE IMPROVED! Welcome home to Highly Desirable Castle Reach! Situated on a Beautifully Landscaped, Level 1-acre lot with a Rare 4-Car Attached Garage, this Meticulously Maintained Home features an Incredible, Private Multi-Generational Flex Wing (added in 2019). Complete with Hardwood Floors, a Kitchenette, a 3/4 Bath, and custom built-ins, this standout space is perfect for an In-Law Suite, Guest Wing and Private Home Office. The main home's 1st floor features an Entertainer’s Dream Kitchen and adjacent Family Room, both boasting Brand-New Modern HW Flooring. The Chef’s Kitchen is fully equipped with an adjacent butler's pantry, 48” Viking Range Top with Grill and Exterior Exhaust Hood, Double Convection Wall Ovens, Wine Fridge and all New Appliances in 2025. The seamless flow is complemented by a Formal Dining Room and 1st Floor Office. Upstairs, the Spacious Primary Suite features Vaulted Ceilings and a Large Walk-In Closet with custom built-ins, alongside a convenient 2nd floor laundry room. Extending your living space is a Recently Finished Lower Level complete with a cozy Electric Fireplace. Step out to a Private Backyard Oasis featuring an expansive 15x40 Brick Patio, the ultimate setup for outdoor entertaining with plenty of fenced flat yard left over for a future pool. Bathrooms have been beautifully updated with brand-new, stylish vanities. Additional details include an Irrigation System and a Kohler Standby Generator for absolute peace of mind. A rare find combining space and extensive modern updates in a Premier Neighborhood!

50 Overton Rd, Windham

$2,475,000

5 Beds ⋅ 5 Baths ⋅ 73549528 MLS

Nestled in one of West Windham’s most sought-after neighborhoods on Heritage Hill Road, this exceptional 4-acre estate offers an unparalleled blend of ultra-privacy, custom craftsmanship, and modern luxury. Masterfully designed to be built by DJ Builders—Southern New Hampshire’s premier custom builder renowned for an uncompromising commitment to quality, this one-of-a-kind residence will sit far off the street, offering the perfect opportunity for a private, gated driveway. Inside, the proposed plan features over 4,400 square feet of exquisite living space defined by the finest materials, custom millwork, and stone accents, including five spacious bedrooms (with both a first-floor and a second-floor primary suite), 4.5 baths, and adaptable flex space. Outside, a separate 3-car detached building provides the ultimate canvas for a car enthusiast or pool/guest house. The builder is also completely open to customize a different design to suit your vision. Photos are digital renderings

41 Heritage Hill Road, Windham

$2,475,000

5 Beds ⋅ 5 Baths ⋅ 5099785 MLS

Nestled in one of West Windham’s most sought-after neighborhoods on Heritage Hill Road, this exceptional 4-acre estate offers an unparalleled blend of ultra-privacy, custom craftsmanship, and modern luxury. Masterfully designed to be built by DJ Builders, Southern New Hampshire’s premier custom builder renowned for an uncompromising commitment to quality, this one-of-a-kind residence will sit far off the street, offering the perfect opportunity for a private, gated driveway. Inside, the proposed plan features over 4,400 square feet of exquisite living space defined by the finest materials, custom millwork, and stone accents, including five spacious bedrooms (with both a first-floor and a second-floor primary suite), 4.5 baths, and adaptable flex space. Outside, a separate 3-car detached building provides the ultimate canvas for a car enthusiast, or it can be modified into a spectacular pool/guest house. While this featured plan is spectacular, the builder is also completely open to customizing a different design to perfectly suit your vision for this incredible lot. Please do not enter the lot without a confirmed appointment. Note: Photos are artist renderings/digitally altered and represent the home's potential build.

41 Heritage Hill Rd, Windham

$1,375,000

4 Beds ⋅ 4 Baths ⋅ 5099668 MLS

Welcome to one of Windham's most sought after neighborhoods! Perfectly situated on a quiet cul-de-sac, this meticulously maintained home showcases true pride of ownership at every turn. The private backyard is an outdoor retreat featuring a spacious deck, patio, and hot tub, creating the perfect setting for relaxing or entertaining family and friends. Inside, you'll find a thoughtfully designed floor plan with a first floor office complete with custom built ins, ideal for working from home. The stunning kitchen is the heart of the home, offering an abundance of cabinetry, a built in buffet, generous workspace, and natural light that fills the room. The inviting family room, sunroom drenched in sunshine, formal dining room, and formal living room provide exceptional spaces for everyday living and effortless entertaining. Upstairs, escape to the enormous primary suite featuring soaring ceilings, a spa inspired bath, and a spacious walk in closet. Three additional bedrooms and a convenient second floor laundry room complete the upper level. The finished walkout lower level adds even more living space with a 3/4 bath, making it ideal for a recreation room, guest space, home gym, or media room. An unfinished storage area provides plenty of room for all your seasonal items and extras. Located just minutes from Griffin Park, top rated Windham schools, shopping, restaurants, and major commuting routes, this exceptional home offers the perfect combination of privacy, convenience, and timeless appeal. Don't miss this amazing opportunity to make it yours. Welcome home!

10 Poplar Rd, Windham

$1,599,000

4 Beds ⋅ 4 Baths ⋅ 5099575 MLS

Timeless elegance meets modern luxury in this exceptional custom Colonial, privately set on 3.5 meticulously landscaped acres. Offering four spacious bedrooms and a beautifully designed walk-out lower-level in-law suite, this remarkable home delivers the perfect blend of sophistication, comfort, and versatility. From the moment you enter the grand two-story foyer, you'll appreciate the impeccable craftsmanship, classic architecture, and custom millwork found throughout. The thoughtfully designed floor plan features a private home office, an elegant formal dining room ideal for entertaining, and a warm, inviting family room centered around a stunning fireplace. At the heart of the home, the expansive kitchen opens seamlessly to the living spaces, creating the perfect gathering place for family and friends. Just beyond, a breathtaking sunroom overlooks the private backyard, filling the home with natural light and providing direct access to the expansive composite deck. Privately situated at the opposite end of the home, the first-floor media room is an entertainer's dream, showcasing custom millwork, a beautifully crafted built-in bar, and the perfect setting for movie nights, game days, or hosting guests. The luxurious primary suite serves as a true retreat with a spa-inspired bath, while the additional bedrooms are all exceptionally spacious. The walk-out lower level offers a complete in-law suite with its own living space, providing exceptional flexibility for multigenerational living, extended family, guests, or an au pair. Step outside to your own private resort where the expansive composite deck overlooks a spectacular gunite inground pool, all surrounded by professionally designed landscaping that creates an unmatched sense of privacy across 3.5 acres. A classic farmer's porch welcomes you home, completing this extraordinary property where timeless architecture, luxurious finishes, and seamless indoor-outdoor living come together.

5 Sherwood Rd, Windham

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