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Town- 45 Pleasant Street

  • 11 Beds
  • 8 + 1 half baths
  • 0.13 acres
  • details iconDetails
$5,170,000
Dec 30 2025
$5,495,000
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An exceptional opportunity situated in the heart of Nantucket Town. A rare offering featuring two fully furnished, independent homes on one lot, just moments to Main Street.
This unique compound includes a 7-bedroom, 4.5-bath home with four finished levels and a 4-bedroom, 4-bath residence with three finished levels, each offering inviting interiors and private patios complete with firepits. Recent upgrades—central air, new roofs, new appliances, and more—make both homes comfortable and carefree. Off-street parking for four cars adds convenience rarely found in town. Perfect for multi-generational living, guest accommodations, and strong rental income. Morning coffee at your favorite café, afternoons wandering through boutiques, evenings dining at your favorite restaurant … all just moments from your doorstep creating the ideal setting for effortless island living.

A proven rental powerhouse, generating over $300K in 2025, with $265K already committed for 2026, largely from repeat guests who return year after year for its comfort and unbeatable location. And it gets even better, a low-mileage 2022 Jeep Wrangler Sahara (4-door) comes with the sale!

Whether you choose to live in one home and rent the other, create a cherished family compound, or enjoy both as high-yield investments, this in-town property delivers unmatched flexibility, lifestyle, and value.

Town- 45 Pleasant Street placeholder
  • 45A and 45B Pleasant Street
  • 45A Pleasant Street
  • 45B Pleasant Street
  • 45B Living Room
  • 45B Living Room
  • 45B Living Room
  • 45B Kitchen - Great Room Sitting area
  • 45B Dining Area
  • 45B Dining Area
  • 45B Kitchen
  • 45B Kitchen
  • 45B Kitchen
  • 45B Kitchen
  • 45B Den
  • 45B Den with Murphy Bed
  • 45B Mudroom
  • 45B Powder Room
  • 45B Primary Bedroom - second floor
  • 45B Primary Bedroom - second floor
  • 45B Primary Bedroom Full Bath
  • 45B Guest Room - second floor
  • 45B Guest Room- second floor
  • 45B Guest Room- second floor
  • 45B Second Floor Hall Bath
  • 45B Stairs to third floor
  • 45B Guest Room - third floor
  • 45B Guest Room-third floor
  • 45B Shared Full bath - third floor
  • 45B Lower Level
  • 45B Lower Level
  • 45B Full Bath Lower Level
  • 45B Laundry Room
  • 45B Patio
  • 45B Patio
  • 45B Patio
  • 45A Pleasant Street
  • 45A Living Area
  • 45A Living Area
  • 45A Living Area looking towards dining area/kitchen
  • 45A Dining Area
  • 45A Kitchen
  • 45A Kitchen
  • 45A Kitchen
  • 45A Guest Room - First Floor
  • 45A Guest Room - First Floor
  • 45A Guest Room full bath connects to Kitchen
  • 45A Guest Bedroom second floor
  • 45A Guest Bedroom full bath
  • 45A Primary Bedroom second floor
  • 45A Primary Bedroom second floor full bath
  • 45A Lower Level Living Area with built in bed
  • 45A Lower Level
  • 45 A Lower Level Hall bathroom
  • 45A Lower Level Laundry adjacent to hall bath
  • 45A Patio
  • 45A and 45B Pleasant Street
  • Property Image 56
  • Property Image 57
  • 45A and 45B Pleasant Street
  • 45A Pleasant Street
  • 45B Pleasant Street
  • 45B Living Room
  • 45B Living Room
  • 45B Living Room
  • 45B Kitchen - Great Room Sitting area
  • 45B Dining Area
  • 45B Dining Area
  • 45B Kitchen
  • 45B Kitchen
  • 45B Kitchen
  • 45B Kitchen
  • 45B Den
  • 45B Den with Murphy Bed
  • 45B Mudroom
  • 45B Powder Room
  • 45B Primary Bedroom - second floor
  • 45B Primary Bedroom - second floor
  • 45B Primary Bedroom Full Bath
  • 45B Guest Room - second floor
  • 45B Guest Room- second floor
  • 45B Guest Room- second floor
  • 45B Second Floor Hall Bath
  • 45B Stairs to third floor
  • 45B Guest Room - third floor
  • 45B Guest Room-third floor
  • 45B Shared Full bath - third floor
  • 45B Lower Level
  • 45B Lower Level
  • 45B Full Bath Lower Level
  • 45B Laundry Room
  • 45B Patio
  • 45B Patio
  • 45B Patio
  • 45A Pleasant Street
  • 45A Living Area
  • 45A Living Area
  • 45A Living Area looking towards dining area/kitchen
  • 45A Dining Area
  • 45A Kitchen
  • 45A Kitchen
  • 45A Kitchen
  • 45A Guest Room - First Floor
  • 45A Guest Room - First Floor
  • 45A Guest Room full bath connects to Kitchen
  • 45A Guest Bedroom second floor
  • 45A Guest Bedroom full bath
  • 45A Primary Bedroom second floor
  • 45A Primary Bedroom second floor full bath
  • 45A Lower Level Living Area with built in bed
  • 45A Lower Level
  • 45 A Lower Level Hall bathroom
  • 45A Lower Level Laundry adjacent to hall bath
  • 45A Patio
  • 45A and 45B Pleasant Street
  • Property Image 56
  • Property Image 57

Additional Details

Sunny kitchen great room with center island providing loads of storage, 6-Burner Thermador Range, GE Monogram Series Refrigerator, Sharp Microwave Drawer, Kitchen Aid Dishwasher, beverage fridge, ice maker, & wall mount Miele Coffee maker. Kitchen opens into a dining and sitting area with Flat Screen TV. Easy access to brick patio. Living room with fireplace; separate den/office area with Murphy Bed. Powder Room

Spacious primary bedroom with private bath and glass shower. Three additional bedrooms share a large hall bath with double vanity, glass shower and linen closet.

Two bedrooms and hall bathroom

Lower level: Entertainment room with dry bar & beverage frig; two additional rooms ideal spaces for a home gym and office or playroom. Hall Bath, Laundry room with 2 large capacity washers and dryers. Utility room with storage, furnace & hot water heater. Exterior egress to patio area.

Property Information

  • 19
  • 11
  • 8
  • 1
  • 0.13 acres
  • 1825
  • 2016
  • ROH
  • Existing
  • Town
  • Town
  • None, Town
  • Full
  • hardwood, tile

Amenities

listing property icon Property

  • Central A/C
  • Disposal
  • Insulation
  • Outdoor Shower

listing outdoor icon Outdoors

  • Patio
  • None Known, Each home has a private brick patio
  • Shared Driveway with two tandem parking spaces - fits 4 cars

listing household icon Household

  • Cable
  • GFHA
  • Thermador
  • Three

Location

Google Map of 45 Pleasant Street, Nantucket, MA, USA

NEIGHBORHOOD

Town

Historically preserved and simply beautiful, downtown Nantucket can be equated to nowhere else in the world. This is the heart of the island, replete with original cobblestone streets, waterfront restaurants and charming grey-shingled shops. Many of the stunning homes abut…

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Town- 45 Pleasant Street

$5,495,000

  • 11 Beds
  • 8 + 1 half baths
  • 0.13 acres

Listing History

Town- 45 Pleasant Street

Property Type: Single-Family
$5,495,000
$5,170,000
Town- 45 Pleasant Street Image

Town- 45 Pleasant Street

Property Type: Single-Family
$5,495,000
$5,495,000
Town- 45 Pleasant Street Image

Town- 45 Pleasant Street

Property Type: Single-Family
$3,850,000
Town- 45 Pleasant Street Image

Town- 45 Pleasant Street

Property Type: Multi-Family
$1,995,000
$1,751,250
Town- 45 Pleasant Street Image

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