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Ob Watrfront 4+ BR. Quiet/Walk to Town. Beachy, classic, great ocean/pond views."""

Bedrooms 4
Property type house
Minimum Stay 3 - 7 nights


About the property

House, 4 Bedrooms + Other (See Description), 2 Baths, (Sleeps 8). Waterviews.

10% off 2018 weeks booked by Feb. 1. Best of everything: we are located on the back side of Farm Pond, which overlooks Harthaven, Nantucket Sound, and Chappaquiddick beyond. It is quiet and private, but an easy walk to playgrounds, town, beach, fishing, shopping, bike paths.


Huge wrap-around porch/deck, big yard, swing set, hammock, use of canoe/kayak (row across the pond to the beach and a great fishing spot). Four bedrooms, all with water views,(1 w/its own staircase) great mattresses and bedding, high cathedral ceilings. Nice napping spot in downstairs double daybed cubby; basement playroom has a pullout queen- fun place to stash kids. BONUS, Negotiable for use: writer's studio in yard with queen pullout and amazing views.

House is a beachy cottage with painted wood floors, beaded board walls and ceiling rafters but also has all modern conveniences: w/d, kitchen with Jennair and lots of counter space, Apple TV. Cozy wood-burning fireplace, two full baths plus huge outdoor shower.Nice big mud room for storing stuff out of the way, and huge basement playroom for kids.

Keywords: House, Cottage, Beachy, Private, Near town, dog-friendly, roomy, Islandy, waterfront, near beach, playroom, office, views, fireplace, big yard, near bike paths, woods, classic Vineyard, history, cozy, year-round, well-insulated, great beds.

More Details

Jamie Kageleiry
Member since: 2006
Speaks: english
Response time:
Within a day
Response rate:
Calendar last updated:
February 25, 2018

About Jamie Kageleiry

I brought my children up in this house, and until a few years ago, we lived here year-round. I am the executive editor at The Martha's Vineyard Times, editing a magazine and newspaper and websites. We think Farm Pond one of the best places in the whole world. People tell us they've never slept better than they do in our house.

Jamie Kageleiry purchased this house in 1990

Why Jamie Kageleiry chose Oak Bluffs

It's rare in that it is close to town, but feels remote. We bought it for the amazing views, the walk to school and town, the nice neighbors and the quirky historical character.

What makes this house unique

Sitting on the big wide front stairs with coffee in the morning (or a drink in the evening), 25 feet from the water, watching the birds, the otters, my husband rowing across the pond to go fishing. Being far enough from town that it's quiet all the time, but close enough to walk in for anything- breakfast, or library, or groceries, or dinner out, a movie, or a warm donut from backdoor donuts late at night. Lying in the 'daybed' nook, surrounded by books, with a fire going in the fireplace, staring out at the water, while someone else makes dinner in the kitchen, which is open to all the rooms downstairs. Riding our bikes out the door to miles of bike paths.

Guestbook comments from the owner

Just wanted to send you a note to let you know how much we've enjoyed your beautiful home! Everything was perfect! We couldn't be happier! The weather was gorgeous, too!

Thank you.
Apr 2011
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Oak Bluffs House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
House Rules:
  • Max. occupancy: 10
  • pets considered ...
  • children welcome
  • non smoking only ...
Location Type:
  • Beach View ...
  • Ocean View ...
  • Water View ...
  • Waterfront ...
  • Broadband Access
  • Clothes Dryer
  • Computer Available
  • Garage ...
  • Heating ...
  • Iron & Board
  • Linens Provided
  • Parking Off Street ...
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Wood Fireplace ...
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Ice Maker
  • Kitchen
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Stove
  • Toaster
  • Dining Area
  • 2 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
  • 2
  • 4 Bedrooms, Sleeps 10
  • King size beds (1) top of the line California King, Stearns and Foster, with views to the pond and ocean from your pillow, Queen size Beds (1) one in bedroom that has its own stairs/ queen pullout in basement playroom, queen pullout in writer's studio, Double Beds (3) the double bed is in the library downstairs, in a built-in nook, surrounded by books, and made private when you pull the curtain closed. Double bed in one upstairs bedroom and additional double pullout in one child's room. Baby Cribs (2) we have two 'pack n plays'., Sleep Sofa or Futons (2) one queen futon is in the basement playroom, and the other is in the separate writer's studio in the yard (10x16, insulated, high-speed internet, amazing views)
  • CD Player
  • DVD Player
  • Music Library ...
  • Satellite / Cable ...
  • Stereo
  • Television ...
  • VCR
  • Video Library
  • Deck / Patio ...
  • Kayak / Canoe ...
  • Outdoor Grill
  • limited accessibility ...
  • arboretum
  • botanical garden
  • churches
  • cinemas
  • festivals
  • health/beauty spa
  • library
  • live theater
  • marina
  • museums
  • playground
  • recreation center
  • restaurants
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • eco tourism
  • horseback riding
  • miniature golf
  • photography
  • scenic drives
  • shelling
  • shopping
  • sight seeing
  • sledding
  • walking
  • whale watching
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cross country skiing
  • cycling
  • deepsea fishing
  • equestrian events
  • fishing
  • fly fishing
  • golf
  • golf privileges optional
  • hiking
  • hunting
  • jet skiing
  • kayaking
  • mountain biking
  • parasailing
  • pier fishing
  • roller blading
  • sailing
  • snorkeling
  • snorkeling/diving
  • sound/bay fishing
  • surf fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • wind-surfing
large mudroom, huge, high-ceilinged playroom in basement with sofa, queen futon, t.v., etc., large, two-room outdoor shower.huge yard.


Wonderful! 4.9/5 -
(12 traveler reviews)

91% Complete
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Ob Watrfront 4+ BR. Quiet/Walk to Town. Beachy, classic, great ocean/pond views.
average rating of 4.9166665 based on 21 reviews

Heartwarming Vacation!

  • 5 of 5

First time to Martha's Vineyard with my husband and this home was perfect! The back deck was a morning breakfast and Happy Hour retreat! Our adult children joined us for the last 3 days and fell in love with it too. Jamie was on duty answering all of my questions on where to get the best coffee to where to hike, bike, dine and sight see. We chose to rent bikes for a week and walk, taking Uber a few times to restaurants and it was a fantastic break from life. We highly recommend this endearing home which feels like you are in the country and a 10 minute walk/4 minute bike ride from all the action and dining.

  • Submitted: Aug 9, 2017
  • Stayed: July 2017
  • Source: VRBO, from HomeAway
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An idyllic spot

  • 5 of 5

This is a truly idyllic spot - it couldn't have been better. We spent a week here and never tired of the views. The house is quirky (which I loved) as only an historic place can be. You'll never want to leave the front porch! Jamie made us feel very welcome - we wanted for nothing!

  • Submitted: Jul 5, 2016
  • Stayed: June 2016
  • Source: VRBO, from HomeAway
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Wakefield, Massachusetts

Great house, Perfect Location!

  • 5 of 5

Had a friends weekend here over Memorial Day Weekend. There were 8 of us, and the place felt like it could have fit more. The house is so broken up that if feels huge (I think it was originally two houses that were combined). The outdoor shower was a great amenity. The location is close to the ocean and right on a small lake which was perfect. It was also good to be close to the downtown but not in the neighborhoods that have houses too close together. It was about 10 minute walk to the restaurants and bars. Jamie the owner gave us very detailed instructions for the house, use of his kayaks, and tons of recommendations for things to do on the island. He was very responsive to make booking easy. Nobody wanted to leave and I hope we can make it back sometime.


  • Submitted: Jun 29, 2016
  • Stayed: May 2016
  • Source: VRBO, from HomeAway
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Rest + Relaxation

  • 5 of 5

If you're looking for a slice of peaceful heaven, then Jamie's house is just the place to hang your hat. Jamie's house has a covered large porch, which overlooks Farm Pond, and Nantucket Sound beyond, where we sip our coffee and read the paper in the morning in total peace and quiet. In the afternoon, we might stroll down to Nancy's and have ourselves a lobster roll for lunch. There aren't many homes on MV in such a quiet location where you can also easily walk to restaurants, beaches, etc. And there are also lots of places to sleep for those unexpected guests who will surely drop by once they hear you're on the island! Book now before it's too late!

  • Submitted: Jan 26, 2016
  • Stayed: August 2015
  • Source: VRBO, from HomeAway
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Concord, MA

Hidden Gem!

  • 5 of 5

Jamie's house in Hearthaven Oak Bluffs is a true hidden gem. The location is perfect with it being a very close walk to the restaurant's and entertainment on Circuit Ave while still offering true peaceful seclusion over looking Farm Pond and Nantucket Sound. The house has an enormous wrap-around porch for lounging and hanging out on while the kids play in the large yard. There are kayaks and a canoe you can use, which we usually use to get across the pond to the beach just across Seaview drive. The beach there has an unusual collection of shells which the kids love. The interior of the home is beach rustic and super comfortable. We typically light a fire and lounge in the large living room with the windows and doors open to enjoy the beach breeze. There is plenty of room for everyone and the house sleeps a large group comfortably. Jamie lives on island and is great with helping with advice on things to do or help finding a baby sitter if you are in need of a night out without the kids. This will be our 4th consecutive year coming back to the house and it always feels like home the moment we arrive. Do yourself a favor and check this place out!

  • Submitted: Jan 18, 2016
  • Stayed: June 2015
  • Source: VRBO, from HomeAway
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Quirky old charmer, perfect for some groups, maybe not for others

  • 4 of 5

This is a quirky old Cape Cod house, very cool architecture and neighborhood, and perfect for certain groups, perhaps less so for others. The views are to die for, across a salt marsh to the Atlantic. The wrap-around porch is fabulous, and there's a great dinner seating area for 10 or 12 people. The house itself is a charmer, I'm guessing two older houses cobbled together. It's a pleasant 15 minute walk to Oak Bluffs downtown, and only 5 or 6 minutes to some swimmable beaches.

It's probably perfect for two couples and several children. But be aware that it's really a 3-BR, with extra sleeping areas. The futon outside one bedroom, the day bed in the dining room, and the cellar room are fine to park some kids in, or if a visitor misses the last ferry, and needs a place to crash, but they are not suitable "bedrooms" for grown-ups. You can sleep 12, yes, but only 6 of those 12 will be in a pleasant bedroom, and all six of those must be willing to share a full-sized bed.

That being said, if your group matches that criterion, it's a fun funky place, with a great deal of charm.

I also liked the pay-it-forward VRBO style, where the spice cabinet was full, and there was olive oil, and some butter in the fridge, etc. I can't stand VRBOs where you have to hit the market for oil or salt or filters just to fry an egg or brew some coffee. There were beers in the fridge when we arrived, we left behind some wine and rum, everybody's happy.

It is a bit of a schlep from the ferry, so if you've got luggage and are older, you might want to hail a cab. There is also a market with liquor and a rib joint (over-rated and over-priced, but hey, you're stuck on an island) on the far side of the property, slightly closer than Oak Bluffs downtown, so if you're feeling lazy, you can find some victuals and grog with a 9 or 10 minute walk rather than a 16 or 18 minute walk.

It's a cool house, but be aware that the sleeping arrangements require some flexibility.

  • Submitted: Aug 5, 2015
  • Stayed: May 2015
  • Source: VRBO, from HomeAway
Owner's Response: Thanks, AC. One thing I'd like to point out about your stay vs. typical stays: the basement and the writer's studio were not available for your weekend stay (the first of the summer season), as there was work being done in the basement, and our neighbors had already requested to use the studio. It's the only time that both the basement and the studio were unavailable to renters. One of the reasons I describe the house as being four bedrooms + is that there are four in the house, plus the writer's studio. AC is right in that one of the bedrooms is smallish, and is adjacent to one of the larger queen bedrooms (which has its own staircase to the first floor). And he's right that the bedroom set up makes it perfect for two families, as the master also has a double room right near it. Technically, the house can sleep 14 people in beds, if you include the bed in the basement , the bed in the studio, and the daybed in the dining/study. But I believe this makes it far too crowded, and 8 is really the ideal maximum. And yes- the house is two houses put together on another site and hauled to the shore of farm pond 100 years ago. The back section was an original Campground (Gingerbread) cottage which was moved to Circuit Ave (Main street) to become a Japanese tea room. That was then moved a few blocks away to join a house built on the original Copeland plan (Oak Bluffs was one of the first planned communities in the US). They were both then moved to my property. In fixing it up, I decided to insulate the roof (new last year) from the outside, to maintain the original rafters. And when I insulated the walls, I used beaded board for interior walls, again to maintain the woody/beachy casual feel. Floors, too, are painted wood. It's definitely not a fancy house, but a classic Vineyard cottage with amazing views from the 900 square foot porch, and easy walking to town, shops, art galleries and beaches, along with kayaking out the front door..
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4 0


Nearest Airport
5 Miles
Dukes County
Nearest Barpub
0.25 Miles
The Barn: Bowl and Bistro
Nearest Ferry
0.5 Miles
Steamship Authority, Island Queen, Hyline, Patriot
Nearest Golf
1 Miles
Farm Neck
Nearest Restaurant
0.3 Miles
Smokin Bones
Nearest Beach
0.2 Miles
Oak Bluffs Inkwell
Car: not necessary

Walking distance to Oak Bluffs arts district with Alison Shaw gallery,and Saturday arts strolls. Also walking distance to tennis, basketball, several parks and playgrounds, walk through woods and meadow to great dog park. Just a few yards from two different bike paths, and rowing distance to little beach at Hart Haven.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee $225
Pet Fee $350
Damage Insurance $59

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.

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