call (508) 228-3202

27 Pilgrim Road • $22,900 - $57,700

Cliff, Nantucket, MA

Located in the highly desirable Cliff area, "Pilgrim's Bliss" is an 8-bedroom, 6.2-bathroom estate with a heated salt water pool, covered wraparound deck with an integrated outdoor fireplace, multiple seating areas for lounging and dining, an expansive yard set back from the main road, and a whimsical, flower-lined path leading to a private duck pond. With its close proximity to many island favorites, in addition to the property's expansive offerings, including a sleeping capacity of 20, "Pilgrim's Bliss" is ideal for extended, multi-generational families with varied interests and leisure pursuits.

First Floor Description

The first floor of the main house offers an open layout with a fully-equipped kitchen featuring high-end appliances and a large center island with seating for six. Adjacent to the kitchen is a dining area that accommodates 14, a powder room, and a brightly-lit living space with plenty of comfortable seating, a wall-mounted Smart TV, a wood-burning fireplace, and two ways to access the wraparound deck and pool area. Completing the first-level is a king bedroom with dedicated office space, private deck access, and en-suite bathroom with double vanity sinks and walk-in shower.

Second Floor Description

The primary bedroom is situated on the second level, offering private balcony access, a king size bed, and an en-suite bathroom with double-sink vanity and walk-in shower. Two additional bedrooms are located on this floor, both with en-suite bathrooms; one with a king bed, the other with a free-standing queen bed, twin bed, and twin-over-full bunkbed.

Lower Floor Description

The lower level features a large media room, which can also be used as a children's play room, a full hallway bathroom, and two guest bedrooms; one with two twin bunkbeds, the other with a king bed.

Cottage

The two-story guest house is situated just behind the main house, directly in front of the pool, offering convenient living and sleeping quarters for extended family and guests, an au-pair, private chef, etc. The main level of the guest house can be accessed from the pool terrace doors, where guests are met with an open dining/living area, a convenient powder bath, and a well-stocked kitchen with a breakfast bar for four. The second level offers a shared full bathroom with tub/shower combo, one bedroom with a queen bed, and one bedroom with two twin beds.

Outdoor Space

Outside, the covered porch overlooks the beautifully-manicured lawn, garden, and pool area. Additionally, there are two outdoor dining spaces and a lounge area with an integrated outdoor fireplace. An idyllic flower-lined path with strung lights leads to a small, private pond with a seating area to view the pond's frequent wildlife visitors, which includes geese, ducks, turtles, bullfrogs, and white egrets.

Distance to Town: 1.2 Miles to Main Street

Distance to Beach: 0.7 Miles to Steps Beach

27 Pilgrim Road Location
Property Code: #2142
Bedrooms:
8 beds
Bathrooms:
6 bath and 2 half
Capacity:
18

Beds Type / Floor

King
1st
King
2nd
King
2nd
Queen + Twin +
Twin-Over-Full Bunk
2nd
Twin Bunkbed (2)
LL
King
LL
Queen
GH
Twin (2)
GH

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Property Amenities

Household Amenities
  • Washer
  • Dryer
  • Iron
  • Ironing Board
  • Hair Dryer
  • Sleeper Sofa
Outdoor Amenities
  • Outdoor Fire Place
  • Patio/Deck Furniture
  • Beach Towels
  • Beach Chairs
  • Beach Umbrella
  • Gas BBQ
  • Outdoor Shower
Kitchen Amenities
  • Gas Stove
  • Microwave
  • Dishwasher
  • Toaster
  • Blender
  • Mixer
  • Coffee Maker (drip)
  • Keurig
  • Food Processor
  • Lobster Pot
Electronic Amenities
  • Wi-Fi
  • TV
  • Smart TV
  • Cable Television
  • Sonos
Property Amenities
  • Steam Room
  • Sauna
  • Steam Room
  • Yard
  • Porch
  • Patio
  • Deck
  • Parking
  • Pets Allowed
  • Private Pool
  • Central AC
  • Heat
  • Usable Fireplace
2026 Availability Sat-Sat Information contained herein is believed to be reliable but is not guaranteed.
June

06/06 - 06/13

$27,700

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06/13 - 06/20

$32,970

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06/20 - 06/27

$43,300

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06/27 - 07/04

$57,700

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July

07/04 - 07/11

$48,650

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07/11 - 07/18

$48,650

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07/18 - 07/25

$49,650

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07/25 - 08/01

$51,980

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August

08/01 - 08/08

$54,100

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08/08 - 08/15

$52,100

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08/15 - 08/22

$46,200

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08/22 - 08/29

$43,900

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08/29 - 09/05

$38,900

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September

09/05 - 09/12

$29,900

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09/12 - 09/19

$29,900

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09/19 - 09/26

$25,900

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09/26 - 10/03

$22,900

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