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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Very Private and Beautiful Estate , Walk to the Beach, Land Bank Trails,

Bedrooms 6
Half Baths1
Space 4,500 sq. ft.
Property type house
Minimum Stay 7 nights


About the property

Fabulous, Private 2 Acre Surfside Estate Overlooking the Ocean with Gunite Pool

Three in One!

Main House!

Pool House!

Studio Cottage!

All for you and your Family!

With, Of Course, a Beautiful 20 X40 Gunite Pool, Beautiful Bluestone Surround

1. Main House Has 4 Ensuite Bedrooms plus a Half Bath

2. Pool House Has 1 Ensuite Bedroom, plus a second Full Bath

3. Studio Cottage Queen Bedroom Full Bath and an Outdoor Shower

20 x40 Gunite Pool with A Beautiful Bluestone Surround

This incredible compound is in the perfect location. Very private and beautiful gardens, with spectacular views overlooking Point of Breakers Beach and Little Weedweder Pond in Surfside. We have land bank trails at the end of our driveway for you and your family to explore. The bike path is right at the end of the driveway can take you to many different areas of the island. A drive to Miacomet Golf Course is 10 minutes away on the back roads, town is 10 minutes away too! We are very centrally situated on the island.

The main house is an upside-down house to take advantage of the tremendous views over the pond to the ocean. The south side of the house, has expansive decks with an abundance of seating to enjoy the relaxed feel of the island with spectacular views. There are three full floors of living space, with living rooms on each floor. The top floor has a cathedral ceiling, contains the master suite, a large living room which is open to the dining area and the brand new, fully equipped gourmet kitchen. We have recently redone many parts of the estate.

We have just installed a 20 x40 Pebble-tec pool which just adds the perfect touch to this compound. There is a beautiful bluestone surround with lots of space to relax and enjoy!

The pool house has a full kitchen, one large king bedroom en-suite. Washer and dryer plus and second full bathroom. On the main floor, there are French doors which lead to oversized deck opening to the pool. There gas grill and plenty of space for family cookouts.

The studio cottage is outfitted with a queen bed with a tiled bathroom. There is a nice relaxed living room along with a small kitchen with all the has a great outside space that is totally private and nicely landscaped for the perfect additional accommodation for any overflow.

This compound will not disappoint!

Three in One!

Main House!

Pool House!

Studio Cottage!

More Details

Gretchen Gigi Callahan
Member since: 2007
Speaks: english
Response time:
Within a day
Response rate:
Calendar last updated:
February 25, 2018

Why Gretchen Gigi Callahan chose Nantucket Island

This property has everything you need to enjoy your family vacation. It has, location, pool and lots of room for your family to enjoy.Strong and beautiful ocean views and within a 5-minute walk to the beach. Peace and quiet with lots of privacy with this incredible estate.There are many areas in and on this property to enjoy for you to get the most out of your family getaway. Come and experience the true feeling of a great family island vacation.

What makes this house unique

We rent Sunday to Sunday only. We find this helps with the boat reservations.

With Three separate buildings, there is a spot for everyone.

Have a family cookout by the pool where there is a brand new BBQ.


Nantucket Island House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 4500 sq. ft.
House Rules:
  • Check-in: 3:00 PM / Check-out: 9:00 AM
  • Max. occupancy: 10
  • children welcome
  • non smoking only
Location Type:
  • Beach View ...
  • Near The Ocean ...
  • Ocean View ...
  • Rural
  • Water View ...
  • Waterfront ...
  • Away From It All
  • Family
  • Air Conditioning ...
  • Basic Soaps
  • Ceiling Fans
  • Clothes Dryer ...
  • Fireplace ...
  • Hair Dryer
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Living Room ...
  • Local Maps
  • Local Restaurant Guide
  • Paper Towels
  • Parking ...
  • Secure Parking
  • Telephone ...
  • Toilet Paper
  • Towels Provided ...
  • Washing Machine ...
  • Water Cooler
  • Wireless Internet ...
  • Blender
  • Coffee Maker ...
  • Cooking Utensils ...
  • Dishes & Utensils ...
  • Dishwasher ...
  • Grill
  • Kitchen ...
  • Microwave ...
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Stove
  • Toaster ...
  • Dining ...
  • Dining Area
  • seating for 8 people
  • 7 Bathrooms
  • 1 Half Bath
  • Bathroom 1-Main House - toilet , shower , master bath fully tiled with a double vanity
    Bathroom 2 - Main House - toilet , tub , shower , This bathroom has a separate shower and tub...all tiled
    Bathroom 3 - Main House - toilet , combination tub/shower
    Bathroom 4 - Main House - toilet , shower
    Bathroom 5 - Studio Cottage - toilet , shower , outdoor shower , Located in the studio cottage, it has an outdoor shower too
    Bathroom 6 - Pool House - toilet , shower , Fully tiled shower in the pool house
    Bathroom 7 - Pool house - toilet , shower , Fully tiled shower in the pool house
    Bathroom - Main House Half - toilet , This half bath is located off the main living room
  • In the Main House we have 4 full baths and a half bath.In the Studio Cottage there is a full bath as well as a outside shower. The Pool House has 2 full baths
  • 6 Bedrooms, Sleeps 10
  • First Floor - 1 queen , en suite
    Master Bedroom on Second Floor - 1 queen , en suite
    Main House Lower Level - 1 king , Main House Lower level
    First Floor Main House - 1 queen , En suite First Floor Main House
    Pool House - 1 king , En Suite Lower Level
    Studio Cottage - 1 queen , Studio Cottage has a Living Room,Kitchen and outdoor shower
  • Three of the four of the bedrooms in the Main house have queen size beds, and the fourth bedroom has a king and of course, all are en-suite bathrooms. The pool house has a king bedroom with en-suite bath plus a second full bathroom. The studio cottage has queen bedwith a full bath plus an outdoor shower.
  • Books
  • Radio
  • Satellite / Cable ...
  • Stereo
  • Television ...
  • Beach Chairs
  • Beach Towels
  • Beach Umbrellas
  • Binoculars
  • Deck / Patio ...
  • Golf ...
  • Lawn / Garden ...
  • Outdoor Furniture
  • Outdoor Grill ...
  • Outdoor Grill Gas
  • Patio
  • Porch Furniture
  • Small Cooler
  • 4 garden chairs
  • 4 beach chairs
  • unsuitable for elderly or infirm
  • wheelchair inaccessible
Pool / Spa:
  • Heated Pool
  • Private Pool ...
  • bay/sound
  • botanical garden
  • churches
  • coin laundry
  • library
  • live theater
  • marina
  • museums
  • nude beach
  • playground
  • pond
  • recreation center
  • restaurants
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • horseback riding
  • scenic drives
  • sight seeing
  • walking
  • whale watching
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • freshwater fishing
  • golf
  • hiking
  • mountain biking
  • pier fishing
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • sound/bay fishing
  • surf fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • wind-surfing
We have a incredible yard for you to enjoy! There is a fenced in pool area as well as other areas which include flower gardens along with lots of open space for outdoor playing.


Exceptional! 5/5 -
(6 traveler reviews)

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Very Private and Beautiful Estate , Walk to the Beach, Land Bank Trails!
average rating of 5.0 based on 6 reviews

Island Paradise!

  • 5 of 5

This property is absolute paradise. We stayed there two years in a row and wouldn't want to stay anywhere else on the island. The house is located in a gorgeous private setting with an amazing pool and outdoor area where we spent most of our days and evenings. Views from the outdoor porch are beauitful. You won't want to leave. The owners are really friendly and helpful. We can't wait to return this summer!

  • Submitted: Jan 1, 2018
  • Stayed: June 2017
  • Source: HomeAway
Owner's Response: Dear Pam Thank you so much for your kind words about our home. We are so lucky to have you as repeat tenants...You and your friends and family treat the house with so much respect...its always wonderful to you! See you again this summer I hope. Gretchen Callahan
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  • 5 of 5

There isn't much that hasn't already been said in the other reviews above, but I'm going to pile on about this gorgeous property anyway.

We stayed here with 3 other families and a few single friends (11 adults / 7 children total) . We could have doubled the size of our group and still not felt cramped.

The flexibility this property provides compared to other places we've stayed on the island is next to none - there's so much space to spread out and plenty of quiet nooks to read and catch a nice mid day nap. Dads and boys walked to the beach, while moms / girls and daughters stayed behind and lounged by the pool. We grilled by the pool and ate outside most nights instead of going into town for dinner (7 kids under 5 influenced this heavily).

All in all we loved staying at Gretchen and Davids lovely home and plan on making 4 Morgan sq our go-to getaway on Nantucket for as long as they'll continue to have us;)

- Katherine M.

Greenwich, CT

  • Submitted: Feb 22, 2018
  • Stayed: August 2017
  • Source: HomeAway
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Quintessential Slice of Nantucket Paradise

  • 5 of 5

This was the third consecutive year that my girlfriend and I, and some friends, have had the pleasure of staying at the Callahan Estate over 4th of July week. All clichés aside - words will never do justice to describing the beauty and serenity of this immaculately-kept sprawling property.

Nantucket is less than an hours flight from where I work and live in Boston, so there's something to be said about a home (or 3 homes in 1 to be exact) that feels light-years away from my normal's truly remarkable.

We go into this week each year with BIG plans: Plans to hit the beach, plans to hit the brewery, plans to go biking, hiking, golfing, and fishing, breakfast plans, lunch plans, dinner plans, etc. Well, I'm here to tell you that this property is the window that all of those plans go flying out of. Why deal with the crowds downtown when you can sprawl out on a pink flamingo float in the massive / gorgeous Gunite Pool with shrimp cocktail in one hand and an ice cold beverage in the other??

Every detail listed in the description of this property is spot on. Would recommend this property to friends and family 10 out of 10 times. The only downside to staying here is that eventually our week comes to and end and we have to leave here to go back to our normal lives...

  • Submitted: Jan 8, 2018
  • Stayed: June 2017
  • Source: HomeAway
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Wonderful Vacation House

  • 5 of 5

We loved our stay in this beautiful house. We dined on the deck and and enjoyed the spectacular water views. The property was better than expected. We have been coming to Nantucket with our family for 15 years and this year, we came with friends. We couldn't have had a better time or a better house. Our group of friends has decided to make it an annual trip to the island and to this property. It's not easy to find a 3 bedroom house that has queen beds and en suite bathrooms. The house is clean and appointed with everything you might need and then some. Gretchen was the perfect host. She was always available to answer any questions or help with anything we might need. The location was perfect. The house sits a short walk from the beach and a short drive or bike ride to town. We wished we could have stayed longer. It was the perfect vacation.

  • Submitted: Sep 15, 2015
  • Stayed: September 2015
  • Source: VRBO, from HomeAway
Owner's Response: Thanks so much for the glowing report on your visit and the house... Hope to see you back again! Gretchen
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Providence, RI

Perfect Vacation Home!

  • 5 of 5

My family and I have been visiting Nantucket for 19 years, and this was quite possibly one of our favorite homes that we've stayed in thus far. As the other reviewer stated, the pictures simply do not do the home justice. The rooms are all open and airy, not to mention extremely clean and comfortable. The finished basement has an office area, a TV area, a pool table, bed and bathroom. The main living floor has 2 large bedrooms with queen beds and beautiful bathrooms, a tv room and a laundry room. The upstairs living level is an open concept TV area and gorgeous new kitchen. The master bedroom is bright and clean, with a queen sized bed, TV, and a huge bathroom. The home also features a guest house which is a studio concept with a kitchen, TV area, a bedroom and bathroom. My favorite part of the house is the upstairs covered deck off of the dining area. The view of the ocean and pond are breathtaking, and we could hear the crashing of the waves while sitting out there at night.

The house is within walking distance to the beach, however because it was the piping plovers mating season, the path to the beach was closed off, making it about a 15 minute walk/5 minute drive to the beach. We really enjoyed this particular beach because although it is a part of Surfside, it was private and quiet and very clean. If you'd prefer the public Surfside beach (snack bar/bathrooms), then that was only about a 5-10 minute drive down Surfside Road.

The owners of this house live on the property, however they gave us our complete privacy and were able to answer any questions we had throughout our stay. I highly recommend this home to any group whether it be a family or a group of friends!

  • Submitted: Jul 22, 2014
  • Stayed: June 2014
  • Source: VRBO, from HomeAway
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Atlanta, GA

Awesome House!

  • 5 of 5

We had a great time in Nantucket and loved this house! The pictures do not do the house justice as it’s hard to capture how large the rooms are and how well everything flows. We had our family vacation on Nantucket this summer and the house was large enough for everyone to have their own space. There are three floors in the main house (two master suites on the middle floor and one on the upper floor), each with its own living room / sitting area – the basement level even has a recreation room with a great pool table. The house and all of the linen / bedding were very clean and well maintained. Please note the guest house does not have air conditioning and is not on par with the main house, so it’s more appropriate for kids or overflow guests for a night or two.

The highlights of the house are the spacious kitchen with restaurant appliances – we cooked in more than half the time and even with 4+ cooks in the kitchen, we had plenty of room to move around; the double porch off the back of the house was great for lounging or having dinner outside; the grounds were very pleasant and relaxing. The house is a good distance from the beach (a healthy 15 to 20 minute walk from the house), but there are wonderful breezes that come off the ocean. There is a beach access road that brings you pretty close to the beach, but it was closed during our stay for the Piper Plovers.

The owner, Gretchen, was very hospitable, which made our stay that much nicer. She was able to answer questions we had and was nice enough to provide us with a couple of beach chairs and an umbrella (I am pretty sure she bought us one!). I would definitely recommend this house.

While on the island, we visited just about every beach, ate at some wonderful restaurants, including Company of the Cauldron, Oran Mor, Brotherhood and The Lobster Trap. And of course we spent a few afternoons at Cisco Brewery!

  • Submitted: Sep 11, 2013
  • Stayed: July 2013
  • Source: HomeAway
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Nearest Airport
4 Miles
Nantucket Memorial Airport
Nearest Barpub
0.4 Miles
The Chicken Box,The Muse
Nearest Ferry
4 Miles
Hyline Ferry and the Steamship Authority
Nearest Golf
1.5 Miles
Miacomet Golf Course
Nearest Restaurant
1.2 Miles
Island Kitchen, Sea Grille, Fairgrounds,
Nearest Beach
0.3 Miles
Surfside Beach
Car: recommended

There are so many wonderful actives here in Nantucket, and the best things are free...enjoy walks...right across the street is an entrance to Land Bank Land that you can walk all the way to Cisco Beach. And then there is the beach which is just a 5 minutes walk from the house.

In Town there are galleries, museums and shopping till you drop.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning $100

The studio cottage is available , at times,separately. For two persons only.
The Nantucket Wine Festival , May 15-18 2014 the cottage is available. Come down for a great time!

Owner's Cancellation Policy

  • Canceled bookings will not receive a refund

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