Kelleher Real Estate Services

Oak Bluffs

Before there was even a town named Oak Bluffs – back in the 1830s – Methodist congregations across New England would organize summer retreats to the outlying woods north of Edgartown, where they would spend a week in revival meetings, hearing as many as four sermons a day. Many found this setting so delightful, they started coming early on their camping trips and staying late. That early tradition of the “camp-meeting” really gave Martha’s Vineyard its start as a summer resort community.

As the Methodists expanded their summer visits, they first built wooden platforms for their tents, and then began building a community of colorful cottages around their open-air meeting center. Thus was born the Island’s only truly original architectural style, known today as Campground Gothic Revival. Some 300 cottages with “gingerbread” scrollwork details and gaily-colored paint schemes still stand at the heart of Oak Bluffs, around the central Tabernacle with its graceful arches of wrought iron.

The historic path of this burgeoning summer resort so departed from Edgartown that in 1880 its residents split away, forming the town of Cottage City. The town took on the new name of Oak Bluffs in 1907.

From its revivalist beginnings, Oak Bluffs has grown to become the Island’s liveliest center for after-hours entertainment, with a downtown district, called Circuit Avenue, bustling well into the wee hours on summer weekends. Oak Bluffs is also home to such landmarks as the Flying Horses, among the nation’s oldest operating carousels, and Union Chapel, a remarkable octagonal structure that dates to 1870.

The Oak Bluffs harbor is known as the Island’s favorite center for power boaters, with its long concrete dock and electrical hookup services. Oak Bluffs is also home to the Island’s most impressive collection of public parks. The jewel of them all is Ocean Park, with a bandstand at the center from which concerts are given on alternating Sunday nights throughout the summer. Ocean Park is also the center for the August fireworks display which traditionally draws the biggest crowds of any single Island event, and which marks the conclusion of the high summer season.

348 Sea View Avenue Oak Bluffs MA

Oak Bluffs, MA348 Sea View Avenue

Price$5,995,000

Est. Mortgage: $/month

MLS Number 35291

  • Multi-Family
  • Village State Beach
  • Location 41.436238,-70.555927
  • Bedrooms 12
  • Bathroom 6

150 Feet of PRIVATE BEACH at this WATERFRONT COMPOUND IN HARTHAVEN - Perched high on a bluff with 180 degree views of Nantucket Sound and beyond, this property offers a rare opportunity for a waterfront family compound or an investor's dream with a private beach. The three homes that make-up this unique 13 bedroom property are as follows: The "Main Deck" is a sprawling cape-style home with 5+ bedrooms, 2 1/2 baths, oil forced hot water heat, air conditioning, wood-burning fireplace, large covered deck overlooking the bluff and a screened-in porch. This home was updated in 1996. This home is considered the main house of the property because of its commanding location perched on the bluff. The "Captain's House" was rebuilt in 1996. It has a reverse-style floor plan to take full advantage of the sweeping water views. Featuring 2 master suites and 2 additional bedrooms that share a bath, this home is light-filled, open and airy. Wood-burning fireplace. The craftsmen that created this home gave extra attention to the wood details throughout and made the house worthy of the finest sea "captain". You will notice these details from the moment you walk into the foyer and move your way through the home to enjoy the beamed ceiling in the living room. The "Cottage" completes this property...almost. This home was also fully rebuilt in 1996. It consists of a living room with wood-burning fireplace, eat-in kitchen, first floor bedroom, first floor laundry and bath. The second floor bedroom has breathtaking views from its private deck. A second large deck runs along the back side of the house. All 3 homes have been created to be independent of each other and all feature air conditioning, outdoor showers and more. With plenty of storage with additional space above, bath and outdoor shower, there is lots of possibilities to to be creative. The garage nicely completes this property. All homes have a solid rental histories with repeat tenants. Sellers would consider a full "turn-key" option. Please view Video of the Property to get a full feel for this one of a kind waterfront property.

Listed by Island Real Estate

$
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$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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395 Barnes Road Oak Bluffs MA

Oak Bluffs, MA395 Barnes Road

Price$4,350,000

Est. Mortgage: $/month

MLS Number 36053

  • Residential
  • Village Lagoon/Harbor
  • Square Feet 4330
  • Bedrooms 4
  • Bathroom 4

RARE OPPORTUNITY ON THE LAGOON WITH A DEEP WATER DOCK - It is rare to find a home in a setting like this on Martha's Vineyard. Tucked away just off Barnes Road, it feels as if you are in a remote locale, yet you are so close to all the Island has to offer. Invite your friends and family. This home boasts room to absorb many people without feeling crowded and has plenty of private retreats for the generations to come. West facing views and glorious sunsets help make this a perfect place to spend - and end - a day. Entertaining is a breeze throughout the open concept main floor. Take in a glorious sunset from the screened porch or out near the dock. Clams and scallops are within your reach just offshore. A ball game or two have been known to erupt on the front yard. Sit back and soak in the natural setting - the fish and fowl will keep you entertained. A deep water dock and deep water access, with the added comfort of the protected location. Come for a visit. You will want to stay for a lifetime.

Listed by Point B Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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19 Old Harbor Lane Oak Bluffs MA

Oak Bluffs, MA19 Old Harbor Lane

Price$3,850,000

Est. Mortgage: $/month

MLS Number 35849

  • Residential
  • Village Sengy
  • Bedrooms 4
  • Bathroom 2
  • Half Bath 1

Rare Opportunity to build 3 separate dwellings or to build your dream home near the water with private beach access and .3 miles to Farm Neck Golf Club! These properties are currently 3 individual lots which can be combined to offer a large estate lot. A summer home is already in place on lot 7, but is not winterized for year-round living. Renderings shown in photos are for visualization purposes and do not necessarily reflect the HOA specifications for Waterview Farms. For Information regarding 4th lot shown please contact listing agent. Two of these parcels adjoin conservation land offering unobstructed views of Sengy Pond, State Beach and beyond. Waterview Farms provides beach access with boat storage and docking available. Explore quaint nearby walking trails to Pecoy Point, or use your paddle boards or kayaks to enjoy Felix Neck & State beach! The MV biking trails access is at entrance to the community with an easy ride to town! This listing includes 7 Old Harbor Lane which is also listed separately.

Listed by Sierra Properties & Investments

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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53 Circuit Avenue Oak Bluffs MA

MLS Number 34827

  • Commercial
  • Village Downtown
  • Bathroom 3
  • Bedrooms 5
  • Half Bath 3

Sparkling newly renovated mixed-use commercial building in a prime and bustling location in Oak Bluffs. Looking to bring your restaurant concept to Martha's Vineyard? This is the perfect turn-key opportunity for a discerning restaurateur. Having been completely rebuilt from top to bottom with design work by Sullivan + Associates, the building is now intelligently configured for use as a high-end restaurant with cocktail bar, espresso bar, seating for up to 99 people, state of the art commercial kitchen, retail space, full commercial basement, and three gorgeous apartments upstairs. Originally built in 1900 and once used as an A&P grocery store, the current owners completed extensive renovations from 2012-2014, bringing the property to an exceptional level of finish and quality. The building meets all fire codes, handicap accessibility requirements, and health regulations, and was thoughtfully engineered to be weather and sound proof. Since the renovations, the property has been operated for four summer seasons (roughly one full year) and is in mint condition. Truly a vibrant and irreplaceable offering in the absolute perfect location for high-end bar/restaurant on Martha's Vineyard.

Listed by Wallace, Peyton of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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225 East Chop Drive Oak Bluffs MA

Oak Bluffs, MA225 East Chop Drive

Price$3,100,000

Est. Mortgage: $/month

MLS Number 33942

  • Residential
  • Village East Chop
  • Square Feet 2449
  • Bedrooms 3
  • Bathroom 3

Top of the Chop ~ A stunning contemporary with dramatic sweeping views of Vineyard Sound. A complete transformation by South Mountain & Company of the former residence resulted in a masterpiece of modern living and superb style. Upon entering you are immediately greeted with water views and the breathtaking landscape and it continues to unfold as you go through the home. The single story home was designed with the living and entertaining area at the core with the master wing tucked privately away and a two bedroom guest wing down its own corridor. The baths are luxurious, the kitchen a work of art and the finishes throughout are simply exquisite. East Chop is an upscale summer community, a most ideal location with the beach, harbor and town just a short distance away.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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53 Tia Anna Lane Oak Bluffs MA

Oak Bluffs, MA53 Tia Anna Lane

Price$2,300,000

Est. Mortgage: $/month

MLS Number 34752

  • Residential
  • Village Lagoon/Harbor
  • Square Feet 2442
  • Bedrooms 3
  • Bathroom 3

Never miss a sunset from this custom built waterfront home! Beautifully designed by Breese Architects with a focus on the stunning water views from each room, this three bedroom, three bath home is the perfect property for entertaining family and friends. Set on one acre of land with stairs to the Lagoon for easy water access and a large, grassy lawn area for all your summer games. The custom built home has a lovely open living space with a field stone gas fireplace anchoring the living room, french doors off of the dining area to the deck and an open kitchen with stainless steel appliances, custom cabinetry and granite counter tops. A second floor Master Bedroom Suite is the only room on this level, with water views from the private balcony, a spacious master bath with double vanity, tile floor and heated towel rack and an office/study area off of the bedroom. There are two guest room wings on the first floor along with two full bathrooms, offering your guests plenty of privacy. A den with built-in bookshelves has access to the loft with a private office space. Finishing off this well designed home is the laundry and mud room with access to a casual side door entry~perfect for coming in off the water. Enjoy the beauty of the Island right from your very own home!

Listed by Coldwell Banker Landmarks

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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42 Paddock Road Oak Bluffs MA

Oak Bluffs, MA42 Paddock Road

Price$1,999,000

Est. Mortgage: $/month

MLS Number 35025

  • Residential
  • Village Sengy
  • Square Feet 4200
  • Bedrooms 5
  • Bathroom 4

OAK BLUFFS - new, luxury enclave - The Preserve at the Woodlands! Enjoy the best of both worlds in this lovely area abutting 200 acres of conservation land yet centrally located off County Road near Farm Neck Golf Club with bike paths that provide EASY ACCESS into downtown Oak Bluffs, Edgartown and Vineyard Haven. Relax and enjoy POND VIEWS and panoramic meadow views. This HIGH QUALITY NEW CONSTRUCTION offers 5 bedrooms and 4.5 bathrooms with 9 foot high ceilings. The wooded 1.8 acre lot offers a spacious backyard with a bluestone patio for entertaining, outdoor shower and borders conservation land for complete privacy. The option to add a POOL is available upon request. An OPEN FLOOR PLAN features a large gourmet kitchen with a Sub-Zero fridge, Wolf range and other professional stainless steel appliances. The living and dining area has lovely views of the pond, custom built-ins and a gas fireplace. A first floor master bedroom contains an en suite bath, dressing area and walk-in closet. For your convenience, there is a first floor laundry room, mud room and powder room. Upstairs there are four SPACIOUS bedrooms - two of which are master bedrooms with en suite baths and vaulted ceilings. The two additional bedrooms share a hallway bathroom with double sinks. Two of the bedrooms offer pond views. There is a set up for an additional washer and dryer upstairs. Enjoy UP-ISLAND PRIVACY with DOWN-ISLAND CONVENIENCE! Don't miss this opportunity to enjoy this beautiful INVESTMENT property and begin to earn income right away. Or enjoy it all year round yourself with family and friends!! MOVE IN READY!!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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24 Paddock Road Oak Bluffs MA

Oak Bluffs, MA24 Paddock Road

Price$1,995,000

Est. Mortgage: $/month

MLS Number 35641

  • Residential
  • Village Lagoon/Harbor
  • Square Feet 3450
  • Bedrooms 4
  • Bathroom 3

New custom home built by Dubin Construction. House includes upstairs and downstairs master bedrooms as well as upstairs and downstairs living rooms. Second floor includes two additional bedrooms with a shared bath. Custom kitchen and cabinets throughout. Hardwood flooring with tile in side entrance, laundry and bathrooms. Large luxurious bathrooms, large deck off living room and dining room. Stone patio off first floor master. Outdoor shower. Still time to customize landscaping.

Listed by Dubin & Reardon

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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15 Peter M. Williamson Boulevard Oak Bluffs MA

MLS Number 34857

  • Residential
  • Village Central
  • Square Feet 3100
  • Bedrooms 6
  • Bathroom 5

BRAND NEW!!! Custom design will be Ready for Occupancy this SEASON. Features over 3100 square feet with another 1000 in finished walkout basement including another bedroom. Beautiful marble/tile work in all bathrooms, wide oak hardwood flooring, gas fireplace with marble mantle, first floor en suite master, 8' sliders with access to sweeping deck, 9' ceilings and cathedral in the living room, and an open kitchen/dining area with Wolf stove, Sub Zero fridge, Bosch dishwasher, large center island. Also, attached 2 car garage with unfinished space above. This house flows comfortably through the intimate spaces offering easy living, privacy, and the yard has room for a pool. A must see!

Listed by Ocean Park Realty Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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6 Marthas Park Road Oak Bluffs MA

Oak Bluffs, MA6 Marthas Park Road

Price$1,895,000

Est. Mortgage: $/month

MLS Number 35698

  • Residential
  • Village State Beach
  • Square Feet 2624
  • Bedrooms 3
  • Bathroom 3

Harthaven Haven with Views of the Association Harbor. Looking for an immaculate new home with access to amenities that are unlike any other neighborhood on the island? Welcome to 6 Martha's Park Road in Harthaven, Oak Bluffs. This reverse-style contemporary home features an open-concept floor plan along with 3 bedrooms and 3 1/2 baths. From the moment you pull it to the pea-stone driveway with stone walls, you begin to see the fine details of this home. This home was built the highest quality materials that will insure low-maintenance home. Walk right across the street to the association harbor and beach or hop on the bike path to town. The ground floor features a first-level master, a second bedroom and a full bath off of the hall. The laundry/utility room opens up to a private oasis under the deck with an outdoor shower and soaking tub. take the stairs up to the second level and prepare to be amazed. This home features open-concept living at its best. The gourmet kitchen features marble counters, stainless appliance and an enormous center island with seating. Enjoy peeks at the water from the living and dining room. The spacious master bedroom has a propane fireplace, private deck with water views, walk-in closet. Master bath has a custom-tiled shower with a rain head and a steam shower. Cathedral ceilings. Central air. Ceiling fans. Irrigation. Alarm. 50-year roof. Top of the line Marvin windows. All bathrooms feature custom tile work. A "command center" allows you to control heating, air conditioning and entertainment from an app. This already spectacular property is being sold turn-key. Pack your bags and get ready to enjoy all that this Harthaven home has to offer.

Listed by Island Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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7 Pennacook Avenue Oak Bluffs MA

Oak Bluffs, MA7 Pennacook Avenue

Price$1,790,000

Est. Mortgage: $/month

MLS Number 33956

  • Multi-Family
  • Village Downtown
  • Bedrooms 8
  • Bathroom 4
  • Half Bath 1

In the coveted Copeland District, steps from beach and town: An unparalleled palace of a property awaits the fortunate investor. Dunmere-by-the-Sea, a soaring, three-story edifice was once an elegant hotel of Oak Bluffs' heyday as a swinging Victorian resort. For the past 40-plus years, this "wedding cake" with panaromic views of Nantucket Sound has served its owners well as a three-unit apartment building with vacation tenants from as near as Boston and as far as Budapest, including many longtime repeaters. Updates over the years have spared many elements of period charm, such as the mansard roof, substantial "gingerbread" trimmings and curvaceous interior stairway. Each unit enjoys bright and spacious floor-through living, with open common areas, full kitchens and baths, two-plus bedrooms and water views. They share use of a laundry, a deep wraparound porch, four parking spaces and generous yard space for lounging and cookouts. The raised finished basement, inclusive of full bath and laundry, has full windows and both indoor and outdoor entries. The opportunities abound: Glamorously upgrade or stay true to the "old school" cottage ambience. Continue the lucrative landlord tradition. Or create condominiums (subject to town permitting). Or go rogue and transform the building into your personal and amazing single-family domain. Property is eligible for tie-in to the town sewer.

Listed by Coldwell Banker Landmarks

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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273 East Chop Drive Oak Bluffs MA

Oak Bluffs, MA273 East Chop Drive

Price$1,695,000

Est. Mortgage: $/month

MLS Number 35374

  • Residential
  • Village East Chop
  • Square Feet 1104
  • Bedrooms 3
  • Bathroom 1

Located on East Chop Drive, this unique offering provides the opportunity to own one of the Vineyard's quintessential beach cottages. The 1,100 sq ft, three-bedroom, 1.5-bath cottage is in immaculate condition with its restored original look, stone fireplace and wrap around porch. Enjoy the beautiful sunsets from your private waterfront, which is also perfect for a refreshing swim or family barbecue. The property could provide an existing MV property owner with a second location for perfect getaways, and with the property's strong rental history, a great investment.

Listed by Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Kelleher Real Estate Services