Oak Bluffs Luxury Real Estate

Find current luxury real estate in Oak Bluffs on Martha’s Vineyard. Contact Ocean Park Realty or call us at 508-693-4210 if you have questions about any of these properties or would like to set up a private tour. Sign up for an account (it's free) to save your favorite luxury properties in Oak Bluffs and get notified when similar properties become available.

Oak Bluffs Luxury Properties For Sale

2 Lagrange Avenue Oak Bluffs MA 02557

Oak Bluffs, MA2 Lagrange Avenue

Price$1,250,000

Est. Mortgage: $/month

MLS Number 41746

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.273

Nestled in the heart of Oak Bluffs, this exceptional single-family home at 2 Lagrange Ave offers a seamless blend of comfort and style. As you step inside, you'll be greeted by the newly renovated kitchen with modern appliances. The house features a spacious 8-foot island, ideal for hosting gatherings! The property boasts 3 bedrooms and 2 full bathrooms spread out over 1670 sq ft. Outside, the home features a beautifully landscaped yard with irrigation. Conveniently located, this residence offers easy access to a variety of amenities, including dining, shopping, and Farm Neck Golf Club. Additionally, this home is just .2 miles from Lagoon Pond, offering a conveniently short commute to the waterfront. The home has seen renovations in recent years. See the documents section for a list of upgrades.

Listed by Andrew McElhinney of Compass LLC

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$/month over payments
Federal 30-year interest rate: 6.9% last updated on Feb 22, 2024
* 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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4 Elisha Lane Oak Bluffs MA 02557

Oak Bluffs, MA4 Elisha Lane

Price$1,485,000

Est. Mortgage: $/month

MLS Number 41706

  • Residential
  • Mls Status Active
  • Bedrooms 2
  • Bathroom 2
  • Acreage 1.378

Welcome your pond front oasis at 4 Elisha Lane. This contemporary cape style two-bed, two full bath home offers a serene retreat atop 1.38 acres in central Oak Bluffs. Enter this 2-bedroom, 2 full bathroom contemporary cape open plan enhanced with cathedral ceilings, skylights and lots of natural ambiance. First floor flows from entertainment to living space; kitchen with all stainless appliances, 6-burner gas range and countertop island, comfortable and inviting living lounge, dining, full bathroom and office alcove. Step from kitchen to outdoor living and dining atop elevated rear deck overlooking the serene yard – perfect for entertaining and enjoying! Primary suite opens to private, covered bluestone patio. Spacious guest bedroom with shared full bathroom and linen and laundry. The finished loft and renovated detached structure open a world of possibilities for bonus living spaces. The hydrangea lined driveway imbues a feeling of opulence. The perennial flower and herb gardens surround the child's play structure inspires a sense of wonder. Privately sited yet easily accessible to town, bike paths and transit make this an ideal location. Boasting a strong rental history and offered fully turnkey. **Passing Title V Septic Inspection in hand, 4 Bedroom Septic

Listed by Allison Cameron Parry of Douglas Elliman MV

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$/month over payments
Federal 30-year interest rate: 6.9% last updated on Feb 22, 2024
* 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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58 Barnes Road Oak Bluffs MA 02557

Oak Bluffs, MA58 Barnes Road

Price$1,100,000

Est. Mortgage: $/month

MLS Number 41690

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.2295

58 Barnes Road is centrally located with close proximity to downtown Oak Bluffs, beaches, Farm Neck Golf, the Sailing Camp and the hospital. This year round, spacious and charming cape cod style house features two first floor bedrooms and full bath with another two bedrooms and full bath on the second floor. Relax on the cozy farmer's porch out front or enjoy the rear yard with large deck for entertaining. The house has a full, unfinished basement with laundry.

Listed by Russell Maloney of Russell Maloney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.9% last updated on Feb 22, 2024
* 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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48 Puritan Drive Oak Bluffs MA 02557

Oak Bluffs, MA48 Puritan Drive

Price$1,395,000

Est. Mortgage: $/month

Active With Contract

MLS Number 41669

  • Residential
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.8

TOWER RIDGE - explore this charming community in a central Oak Bluffs location. Inside this home you will be greeted by a comfortable and inviting living space featuring a majestic double-sided stone fireplace. The well-designed layout permeates every room seamlessly combining functionality with style, offering a perfect balance for daily living and entertaining. Step outside and discover the expansive lot – a canvas for your outdoor aspirations. Whether you envision lush gardens, outdoor gatherings, or simply enjoying the tranquility of nature, this property provides the perfect backdrop. You'll enjoy easy access to local amenities, such as hiking trails, Farm Neck Golf Club, restaurants, ferries and the beach! Embrace the opportunity to make this your new home – where comfort and serenity converge in perfect harmony. Home is being sold 'as is.'

Listed by Jennifer B. DaSilva of Compass | Point B

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$
%
$/month over payments
Federal 30-year interest rate: 6.9% last updated on Feb 22, 2024
* 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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32 Harthaven Road Oak Bluffs MA 02557

Oak Bluffs, MA32 Harthaven Road

Price$2,800,000

Est. Mortgage: $/month

MLS Number 41553

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 4.5
  • Acreage 1.9

Located in the desirable Harthaven community, this spacious colonial offered fully furnished, features open concept living with hardwood floors, upgraded "cooks" kitchen with granite countertops, and a two car garage. Large screened in porch with fireplace for year round entertaining. The second fireplace in living room wraps around to two seating areas. Four large primary suite bedrooms all have private full baths and walk in closets. Harthaven is a wonderful enclave of homes on the outskirts of Oak Bluffs on the way to Edgartown with beauty, privacy and history. This 1.9 acre parcel abutting conservation land offers privacy, beautiful landscaping and full association amenities including a mile of Nantucket Sound beach, access to Farm Pond, a small boat harbor with dock, and tennis court with pickleball court. Lot proximity affords impromptu walks to Farm Neck golf course, 74 acre Trade Winds Conservation trails and bike path along the beach.

Listed by Rebecca V Conroy of Conroy & Company R.E.,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.9% last updated on Feb 22, 2024
* 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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3 Mayhew Way Oak Bluffs MA 02557

Oak Bluffs, MA3 Mayhew Way

Price$2,795,000

Est. Mortgage: $/month

MLS Number 41577

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.78

Welcome to this exceptional home nestled in the coveted Tower Ridge Community. This property enjoys a prime location next to Farm Neck Golf Club, allowing residents the opportunity to partake in world-class golfing and tennis. This residence not only enjoys close proximity to Martha's Vineyard's finest beaches but also showcases a newly constructed 18x38 pool and pool house, designed by renowned architect Patrick Ahearn. 3 Mayhew Way is where luxury and modern comfort seamlessly blend to create a single-floor residence of unparalleled elegance. This spacious floor plan encompasses 4 bedrooms and 2.5 bathrooms, providing ample space for relaxation and entertainment. High-end finishes and thoughtful details adorn the interior, creating an atmosphere of sophistication and style. Upon entering, you will be greeted by carefully curated interior amenities. The kitchen boasts elegant granite countertops and top-of-the-line stainless steel appliances. The fireplace adds a touch of warmth to this sophisticated abode. The attached 3-season room offers a seamless transition between indoor and outdoor living. Beyond the interiors, this residence offers an impressive array of exterior features. A notable highlight is the landscaping, curated by Donaromas, which enhances the outdoor space, creating a serene oasis for relaxation. This exceptional property presents a rare opportunity to experience the epitome of luxury living on Martha's Vineyard.

Listed by Andrew McElhinney of Compass LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.9% last updated on Feb 22, 2024
* 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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11 John Wesley Avenue Oak Bluffs MA 02557

Oak Bluffs, MA11 John Wesley Avenue

Price$1,849,000

Est. Mortgage: $/month

MLS Number 41599

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 1.5
  • Acreage 0.13

Welcome to this charming coastal retreat! Nestled in on a quaint street in the East Chop neighborhood of Oak Bluffs just a short walk from the pristine shores of Martha's Vineyard and nearby town center. This picturesque 4 bedroom home with original hardwood floors captures the essence of a perfect beach house with a blend of comfort, style, and seaside living. The wrap-around porch, adding a touch of nostalgia and providing a perfect spot to enjoy lazy afternoons or entertain guests. The spacious open rooms, high beamed ceilings and ample windows make this inviting retreat perfect for summers by the sea, and it's also a solid 4-season home for carefree year-round living. The property includes a grassy yard, an oversized one-car garage, and storage shed providing secure parking and additional storage space.

Listed by Lisa Lucier of Anchor Realty of Martha's Vineyard

$
$
%
$/month over payments
Federal 30-year interest rate: 6.9% last updated on Feb 22, 2024
* 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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16 Franklin Avenue Oak Bluffs MA 02557

Oak Bluffs, MA16 Franklin Avenue

Price$1,980,000

Est. Mortgage: $/month

MLS Number 41602

  • Residential
  • Mls Status Active
  • Bedrooms 6
  • Bathroom 2
  • Acreage 0.26

This 6 bedroom 2 bath house sits on a .26 acre corner lot overlooking a park. Close to town, beaches, parks, and recreation. The main floor has an open concept kitchen, living and dining island that seats 8, a full bath with new tile work and new tub, and 2 bedrooms. Upstairs offers 4 more bedrooms and another bath. In addition to the 1,920sq.ft of the house, the walk-out basement provides great extra living space. Large deck and spacious fenced-in yard. New windows, sliders. gutters, roof, shingles, insulation, and siding. New septic in 2020. Property has had good rental history on VRBO.

Listed by Angela Murphy of Laer Realty Partners

$
$
%
$/month over payments
Federal 30-year interest rate: 6.9% last updated on Feb 22, 2024
* 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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2 East Side Road & 60 Bay View Avenue Oak Bluffs MA 02557

MLS Number 41587

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.25

Stunning sunsets await. This quintessential bungalow style Vineyard home has been lovingly maintained and enjoyed by the same family for close to 100 years. Built in 1933, the main house includes three bedrooms, two full baths and hardwood floors throughout. The spacious living area boasts high ceilings, stone fireplace, and expansive water views. Summer days and nights are well spent under the covered porch. Watch the ferries come and go and delight in the dazzling colors of the setting sun. Recent renovations include raising the house and the pouring of a foundation offering an additional 930 square feet of lower level living area. Experience true Vineyard living at its best, just steps away is easy access to the Lagoon with clamming, swimming, and boating. Bring your vision to the open and airy studio/ bunkhouse that is included in this offering at 60 Bay View Avenue and features the same wonderful vistas. Two unbuildable lots abut this property so you will never lose sight of the breathtaking scenery. This classic home is a rare Vineyard offering and not to be missed.

Listed by Carol Shore of Donnelly + Co

$
$
%
$/month over payments
Federal 30-year interest rate: 6.9% last updated on Feb 22, 2024
* 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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4 High Meadow Lane Oak Bluffs MA 02557

Oak Bluffs, MA4 High Meadow Lane

Price$2,650,000

Est. Mortgage: $/month

MLS Number 41548

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3.5
  • Acreage 0.8899

Set back and overlooking a sprawling front yard from the quintessential farmer’s porch you can envision family and friends enjoying the outdoors! Soaring cathedral ceilings and beautiful craftsmanship will immediately capture your attention upon entering this expansive cape style home. Many upgrades make this a gracious charmer from the get go.. The floor plan is fabulous, from the bright large kitchen outfitted with ample granite counters, rugged commercial Wolf stove, wine fridge and eat-in counter plus table eating is perfect for family gatherings and entertaining. SOLID is the best way to describe what you will experience when you visit this home. Post and Beam construction levels up with Energy Efficient SIP style of insulation plus Radiant heat through the floors. Central AC and great use of sized windows lets all the light in! First floor primary bedroom is spacious with walk in closet and full bathroom with tub. There is a 2nd bedroom that is currently being used as a TV room. 2 more sizeable bedrooms ensuite and closets complete the 2nd floor. The Lower level is partially finished with key and perfect for multigenerational flex space and or a game room or office. Bring your imagination and personalize the possibilities! There is more! A large Garage with additional space above that can be finished for other creative use. Situated on .89 acres of land, so much yard for all occasions. Lawn games, get togethers outdoor fun all surrounded by beautiful landscaping and Abutting a buffer of Common Land! This is an impressive home base perfect for year-round, a fabulous vacation spot and or generate impressive rental income. Meadow View Farms is a lovely welcoming community that offers beautiful walking paths, along with Association Tennis courts. Perfectly convenient to the bike paths, bus routes central to the down island towns. Title V inspection has been completed and passed.

Listed by Martha Smith of C McManus Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.9% last updated on Feb 22, 2024
* 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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38 Kennebec Avenue Oak Bluffs MA 02557
Pending

MLS Number 41552

  • CommercialSale
  • Mls Status Pending
  • Bathroom 1.5
  • Bedrooms 1
  • Half Baths 1

A well established and successful restaurant located in the heart of downtown Oak Bluffs known as Jimmy Seas Pan Pasta. Sale includes real estate, 50 seat restaurant business, restaurant equipment, furnishings, and all inventory. The second floor offers one large living area, a bedroom with attached office, storage, and full bath. Current owner was permitted for and built a new second floor exterior water view deck, which provides a second egress and legal living space. Investors can investigate with the town the possibilities for further expansion of the restaurant business or adding a third floor creating fantastic views over Ocean Park to Nantucket Sound. Many recent improvements including a new roof, exterior painting, exterior doors, awning and three mini-splits. Newer restaurant equipment, updated plumbing and furnace and newer kitchen utensils, pots, pans, glassware, and silverware. Great investment opportunity for this turnkey operation. Financials available for qualified buyers.

Listed by Skip Dostal of Martha's Vineyard R.E.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.9% last updated on Feb 22, 2024
* 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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21 Hudson Avenue Oak Bluffs MA 02557

Oak Bluffs, MA21 Hudson Avenue

Price$2,950,000

Est. Mortgage: $/month

Pending

MLS Number 41542

  • MultiFamily
  • Mls Status Pending
  • Bedrooms 8
  • Bathroom 4.5
  • Acreage 0.4399

Income Generating Wonder! Calling all Contractors, Business Owners, Entrepreneurs, Investors with vision., Now is the perfect time to make a smart move in real estate ownership that provides choices and many possibilities. Do you need housing for your employees? This property has it! Originally designed as the owner's apartment and housing for the entire staff of the Pequot Hotel, the property includes an oversize two-bedroom “owners’ apartment” with large kitchen and two baths. Alongside is a shared dormitory style rental space, 8 bedrooms with common XL Kitchen and three baths. There are two large garage bays with large storage ability, featuring a half bath and an office. 11-foot ceilings, and plentiful shelving, heat etc. Perfect for storing all types of equipment or even space for boats. Set back privately on the backside of the lot there is also plenty of parking and a lovely yard for outdoor enjoyment. 21 Hudson is situated in the sought-after zip code 02557, conveniently located within walking distance to the bus route and bike paths, off County Rd. Whether you're looking to live, work, or rent, this property is ready for you! A Truly RARE REAL ESTATE GEM! Square Footage is a total of both units and all data included here is from Town of OB Assessors.. This is a unique offering - A Must See to understand and appreciate all that it offers.

Listed by Martha Smith of C McManus Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.9% last updated on Feb 22, 2024
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

Based on information submitted to LINKMV as of February 24, 2024 . All data is obtained from various sources and has not been, and will not be, verified by broker or LINKMV.  All information should be independently reviewed and verified for accuracy.  Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

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