Browse All Carlisle MA Historical Properties for Sale

Much admired in town for its charming presence and beautiful gardens, this inviting Carlisle Cape pairs timeless New England character with thoughtfully updated interiors. Stone walls, a bluestone walkway and an abundance of perennials and flowering shrubs create a memorable welcome, while the lovely backyard offers a peaceful setting to enjoy throughout the seasons.Enter through the bright, enclosed breezeway connecting the two-car garage to the home, where warm hardwood floors and comfortable gathering spaces await. The spacious family room features exposed ceiling beams, a fireplace and large windows overlooking the grounds, with direct access to the expansive backyard patio. Open to the family room and dining room, the gourmet kitchen is beautifully appointed with custom cabinetry, Thermador appliances, granite countertops, a copper sink and a generous center island. Whether preparing a quiet dinner or hosting a lively gathering, the layout keeps everyone connected.A separate fireplaced living room provides another inviting space to unwind, while a first-floor bedroom and recently remodeled full bath offer welcome flexibility. Upstairs, two generously sized bedrooms are complemented by a second recently remodeled full bath. An unfinished basement provides ample room for storage.Outside, the broad patio extends the living space into a beautiful backyard framed by established plantings, stone walls and mature trees—an idyllic setting for outdoor dining, gardening or simply enjoying the surroundings. Nearby nature trails add to the appeal of this much-loved Carlisle home, where classic charm, modern comforts and exceptional outdoor spaces come together beautifully.

428 Brook Street, Carlisle

Listing courtesy of Listing Agent: The Laura Baliestiero Team from Listing Office: Coldwell Banker Realty - Concord.

$1,275,000

5 Beds ⋅ 4 Baths ⋅ 73587973 MLS

Extraordinary architecture, a connection to rock-and-roll history and a remarkably flexible layout make this Carlisle property truly one of a kind. Two distinct buildings joined by a newly constructed covered bridge create an exceptional opportunity for multigenerational living, working from home or pursuing creative passions—with space to come together and room to retreat. The main residence offers a kitchen, living and dining rooms, and three bedrooms on the main level. Downstairs, a spacious primary bedroom with a private bath is complemented by a family room with a separate exterior entrance, creating a private suite ideal for extended family or guests. A 2-car garage adds convenience, while central air conditioning and a new high-efficiency gas heating system provide year-round comfort. Across the covered bridge, the second building offers a dramatic change of atmosphere, with stunning exposed beams, rich wood finishes and soaring spaces. A sitting room with a woodstove provides a cozy gathering spot, while the expansive family room features a floor-to-ceiling stone fireplace and sliders to a deck. An overhead catwalk adds architectural interest, overlooking the space below, while a loft offers a bedroom and 2 separate storage spaces. The lowest level features a heated workshop, heated darkroom and a former recording studio with a sound booth once used by The J. Geils Band and The Cars. From working at home to making music or pursuing a favorite hobby, these distinctive spaces offer exceptional versatility. This building is served by its own oil heating system and has 2 additional heated garage spaces. Outside, a beautiful, wooded setting frames the buildings, decks and a detached screen house, refreshed with new paint and ready for leisurely afternoons or evenings with friends. A Generac backup generator adds peace of mind. Offering character, history and room to shape life around the way you live, work and create, this Carlisle home offers something rare and remarkable!

148 Rutland Street, Carlisle

Listing courtesy of Listing Agent: The Laura Baliestiero Team from Listing Office: Coldwell Banker Realty - Concord.

$880,000

4 Beds ⋅ 3 Baths ⋅ 73584456 MLS

Tucked back from a scenic road on two acres near the Concord line, this versatile home offers a flexible, open layout designed for comfortable everyday living. A thoughtfully designed family room addition opens directly to the kitchen and features a vaulted ceiling, casual dining area and access to the screened porch and rear patio. The expansive 32' x 13.5' living and dining area continues the open flow and offers exceptional flexibility for furnishing and entertaining. This upper level also includes a primary suite, two additional bedrooms and two updated bathrooms, while the lower level provides a fourth bedroom, half bath with laundry and a playroom. Recent improvements include a newer roof, central air conditioning and interior paint. Enjoy casual dining on the screened porch or relaxing nights around the firepit. The private two-acre parcel has great potential to create an expanded yard or to simply enjoy the surrounding natural setting. Conveniently located for commuters and close to the extensive trail network in Estabrook Woods, this home provides opportunity to enjoy all that this special community has to offer.

320 Russell Street, Carlisle

Listing courtesy of Listing Agent: Barrett & Comeau Group from Listing Office: Barrett Sotheby's International Realty.

$1,199,900

4 Beds ⋅ 5 Baths ⋅ 73581559 MLS

Set against a wooded backdrop in one of Carlisle’s most vibrant neighborhoods, this spacious 4-bedroom, 3 Full, 2 Half-bath classic center-entrance Colonial is approached by a circular driveway framed by mature landscaping. Gleaming hardwood floors and generously sized, front-to-back rooms create a wonderful sense of space throughout.The bright, expansive kitchen features abundant cabinetry, granite countertops, an extra-large island, two ovens, a built-in hutch and a comfortable dining area. Just off the kitchen, an inviting den offers built-in cabinetry, a distinctive vintage indoor brick grill and access to a large deck overlooking the backyard.The spacious living room provides ample room for entertaining and flows seamlessly into an impressive family room addition with cathedral ceilings and walls of glass framing the natural landscape.Upstairs, the primary suite includes a private updated bath and walk-in closet, accompanied by three additional bedrooms and a full bath. The finished walk-out lower level offers exceptional flexibility for extended family or potential ADU use, featuring three separate finished rooms, a full bath and an additional half bath. A large two-car garage with storage above completes this versatile Carlisle home, offering plenty of room to live, gather and make it your own.

54 Carleton Road, Carlisle

Listing courtesy of Listing Agent: The Laura Baliestiero Team from Listing Office: Coldwell Banker Realty - Concord.

$1,199,900

4 Beds ⋅ 3 Baths ⋅ 73578499 MLS

Filled with natural light, this spacious 4-BR Carlisle home offers a flexible layout, beautiful outdoor spaces and a 5-BR septic—a fifth bedroom was previously converted to a convenient 2nd-floor laundry room. The inviting interior features hardwood floors, a bright kitchen with granite countertops and stainless-steel appliances, along with a step-down family room with a fireplace and direct access to the screened porch. Upstairs, the generously sized primary bedroom includes a private bath, while three additional bedrooms provide plenty of room for family, guests or a home office. A spacious finished bonus room in the basement offers endless possibilities for recreation, exercise or hobbies. Outside, enjoy a large composite deck, stone patio and beautiful gardens surrounded by a peaceful natural setting. An attached 2-car garage and nearby access to Carlisle’s many walking trails and conservation lands complete this wonderful property.

320 Heald Road, Carlisle

Listing courtesy of Listing Agent: The Laura Baliestiero Team from Listing Office: Coldwell Banker Realty - Concord.

$1,499,000

5 Beds ⋅ 4 Baths ⋅ 73569406 MLS

Your search ends here! Discover this stunning 5-bedroom, 3.1-bath custom estate designed for both luxury and functionality, featuring high-end finishes throughout. The main level offers a bright living room with a cathedral ceiling, a spacious primary suite with walk-in shower, floating tub, and walk-in closet, plus a dining room and gourmet kitchen with white cabinetry, stainless steel appliances, and a 10-ft island. Additional highlights include a coffee station, half bath with laundry, and a four-season sunroom. The second-floor features three generously sized bedrooms with walk-in closets and a full bath. The walk-out basement includes a large family room, full bathroom, and office. Extensive upgrades include new septic system, well tank, driveway, landscaping, roof, porch and dormer with metal roofing, garage door and motor, Trex deck with cable railing, spray foam insulation, heat pump, electrical, plumbing, hardwood floors, custom kitchen, appliances, and updated bathrooms.

61 Meadowbrook Road, Carlisle

Listing courtesy of Listing Agent: Naima Mazouzi from Listing Office: Eagle Eye Realty PLLC.

$1,174,000

4 Beds ⋅ 3 Baths ⋅ 73565380 MLS

PRICE IMPROVEMENT! Welcome to 27 Maple Street, a 4-bedroom Colonial on 2.26 private, landscaped acres that is truly TURN-KEY! A significant 2024 addition includes a large primary suite with a full bath and a walk-in closet, a mudroom with built ins and storage, a vaulted, sun-filled family room that brings the outdoors in. The addition includes a 2 car garage that features epoxy flooring, an oversized bay for a larger vehicle and Level 2 EV car charging. Upstairs you'll find 3 additional bedrooms with 2 of the rooms having large double door closets. The kitchen was refreshed in 2026 featuring quartz counter tops, new tile flooring and a tile backsplash complemented by appliances updated in 2023. This basement is clean and ready to be used for storage, a home gym, or flexible space. The BIG TICKET WORK is already done in this home, which includes highly durable Hardie board siding (2024), a 200A electrical panel (2024), a new asphalt driveway (2024), chimney repointing (2025) a redone cellar door (2025), a gas hot water heater and AC compressor (2023). Double-pane windows throughout complete the package sealing in the warmth, keeping your family comfortable through the coldest New England winters. Set in beautiful Carlisle, this home delivers modern day amenities for all to enjoy while being part of a great community known for it's rural character, extensive conservation land yet a short drive from highways and shopping.

27 Maple St, Carlisle

Listing courtesy of Listing Agent: Dina King from Listing Office: REMAX Executive Realty.

$599,000

3 Beds ⋅ 1 Baths ⋅ 73525176 MLS

Builders & contractors - don't miss this opportunity! Beautiful, level lot in desirable Carlisle. Current structure is a 3 bedroom, 1 bathroom ranch needing considerable work. Property is being sold in "as is", "as seen" condition. Will not qualify for conventional loan programs. No representations are made by seller or listing office/agent. Showings by appointment only. Do not walk property without listing agent present.

38 Rutland St, Carlisle

Listing courtesy of Listing Agent: John Beckshaw from Listing Office: J. Borstell Real Estate, Inc..

$1,999,999

5 Beds ⋅ 5 Baths ⋅ 73485083 MLS

Architectural drama meets breathtaking natural beauty in this extraordinary custom mid-century Deck House set on 13 private acres abutting conservation land. Walls of floor-to-ceiling glass define the heart of the home, capturing sweeping northwesterly views and spectacular sunset skies while seamlessly bringing the outdoors in. Designed for both grand entertaining and peaceful retreat, the property features an in-ground saltwater pool, magnificent natural surroundings, and exceptional privacy. The home offers 5 bedrooms, 3 full and 2 half baths. A total of 8 garage bays—including a detached 6-car garage—make this property ideal for the car enthusiast or hobbyist. A new 7-bedroom septic system, to be installed prior to closing, allows the 6-car garage to be converted into a 2-bedroom ADU. Rarely does a property of this caliber, setting, and architectural significance become available.

1090 North Road, Carlisle

Listing courtesy of Listing Agent: The Laura Baliestiero Team from Listing Office: Coldwell Banker Realty - Concord.

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Carlisle Historical Real Estate

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Browse All Carlisle MA Historical Properties for Sale

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