Nantucket Property Transfers: Week Ending Friday, February 20, 2026

27 Fairgrounds Road

Mid Island $4,200,000 Days on Market: 125 Bed: 0 Bath: 0

Welcome to 27 Fairgrounds Road, Nantucket—a prime opportunity in a thriving area. Sprawling across 67,518 square feet, this property boasts a spacious 5,410 square-foot building currently home to the renowned Fairgrounds Restaurant and Pudley’s Pub. With three bathrooms and a versatile layout, the possibilities are endless. Whether you envision continuing the successful restaurant legacy or exploring potential subdivision options, this property offers a multitude of paths forward. Consider the opportunity to create six 10,000+ sq. ft. lots, a combination of three 10,000 sq. ft. lots with two 12,000+ sq. ft. lots, or three expansive 22,000+ sq. ft. lots. This unique offering promises significant potential for the visionary investor. Don’t miss out on this exceptional property.

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37 Cliff Road

Cliff $8,141,000 Days on Market: Bed: 5 Bath: 5

Ideally located on Cliff Road near Town and Steps Beach, this property offers a classic Nantucket layout with ample space for family and guests. The first floor features a bright, open kitchen, generous living room, and dining area that flow seamlessly for easy entertaining. A king bedroom and full bath on this level provide convenient first-floor living. The second floor includes three additional bedrooms and a shared bath. Above the attached two-car garage is a private guest suite with a full bath—ideal for visitors or extended stays. A wonderful opportunity to enjoy one of Nantucket’s most desirable neighborhoods.

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20 Pine Grove Road

Mid Island $2,400,000 Days on Market: 62 Bed: 6 Bath: 6

Great opportunity for investment or employee housing all new shingles side and roof and some new windows. gas heat all metered separate both electric and gas. This is a side by side duplex. Both sides have a first floor bedroom, kitchen, dining and living room.full bath/laundry room. Second floor has two bedrooms and a hall full bath. Both duplexes have separate full lower level living areas and full baths. Need 24 hr show clause.

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Contact us for more information.