Oak Bluffs Homes

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  /27

  $1,150,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,500 Sq Ft

  70 Carol Ln, Oak Bluffs, MA 02557

  Charming Renovated Ranch in the Heart of Oak Bluffs Discover the perfect blend of comfort, convenience, and coastal charm in this beautifully renovated ranch home, ideally located in a central Oak Bluffs neighborhood close to everything down-Island. Set on a spacious 1/3-acre lot, this property offers both privacy and proximity — just minutes from the Oak Bluffs School, town center, and all the

  

  Lisa Lucier

  Anchor Realty of Martha's Vineyard

  (508) 456-5742

  70 Carol Ln, Oak Bluffs, MA 02557
• Explore Oak Bluffs

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  /41

  $8,750 total monthly price

  • 4 Beds
  • 2.5 Baths
  • 1,811 Sq Ft
  • House for Rent

  11 High Meadow Ln, Vineyard Haven, MA 02568

  **SUMMER WEEKLY RATE ** INQUIRE FOR LONG TERM OFFSEASON RATE**Discover the perfect summer retreat in this beautifully updated Meadow View Farms home. Nestled on a private hilltop and minutes from beaches, bike paths, Farm Neck Gand Downtown Oak Bluffs, this home offers a serene escape close to the island’s best attractions. 4 spacious bedrooms, first floor primary ensuite, shared secondary floor

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  11 High Meadow Ln, Vineyard Haven, MA 02568
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  /19

  $750,000 Sold Nov 07, 2025

  41 Trinity Park, Oak Bluffs, MA 02557

  • 4 Beds
  • 1 Bath
  • 1,154 Sq Ft
  • Built 1867

  Last Sold Summary

  • 6% Below List Price
  • $650/SF
  • 14 Days On Market

  Current Estimated Value $783,349

  Last Listing Agent Stacy Ickes Donnelly + Co.

  41 Trinity Park, Oak Bluffs, MA 02557
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  /10

  Not Listed For Sale

  0 Shawanue Ave Unit 32400336, Oak Bluffs, MA 02557

  0 Shawanue Ave Unit 32400336, Oak Bluffs, MA 02557

  Last Sold Summary

  • 70 Days On Market

  Last Sold Price $550,000

  Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's International Realty
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  /36

  $2,900,000 Pending

  • 4 Beds
  • 5 Baths
  • 5,165 Sq Ft

  63 Bayes Hill Rd, Oak Bluffs, MA 02557

  Tucked away in a serene setting, this beautifully designed custom home offers the ultimate in privacy, comfort, and luxury living. The first floor features a spacious open-concept design, seamlessly blending the dining room, kitchen, wet bar, and living area-perfect for entertaining or relaxing with the family. Home chefs will fall in love with the gourmet kitchen complete with custom cabinetry,

  Casandra Hyland Sandpiper Realty, Inc.

  63 Bayes Hill Rd, Oak Bluffs, MA 02557
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  /22

  $20,000 total monthly price

  • 5 Beds
  • 3 Baths
  • 3,000 Sq Ft
  • House for Rent

  55 Samoset Ave, Oak Bluffs, MA 02557

  Modernized 5 bed, 3 full bath Victorian in the heart of Downtown Oak Bluffs. Steps to restaurants, shopping, harbor, ferries and beaches. Accommodates 10 guests. Easy breezy outdoor living, dining, bluestone patio and BBQ grill. Relax on the covered porch surrounded by a lush flower garden or unwind in the outdoor shower. Updated stone and stainless kitchen. Formal dining for eight. A/C, WIFI and

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  55 Samoset Ave, Oak Bluffs, MA 02557
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  /26

  $1,600,000 Sold Nov 07, 2025

  96 Pondview Dr, Oak Bluffs, MA 02536

  • 4 Beds
  • 2.5 Baths
  • 2,115 Sq Ft
  • Built 2004

  Last Sold Summary

  • 1% Below List Price
  • $757/SF
  • 35 Days On Market

  Last Listing Agent Doug Burke Cronigs Real Estate

  96 Pondview Dr, Oak Bluffs, MA 02536
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  /24

  Est $1,082,211 Not Listed For Sale

  18 Brunswick Ave, Vineyard Haven, MA 02568

  • 3 Beds
  • 1 Bath
  • 875 Sq Ft
  • Built 1870

  18 Brunswick Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 3% Above List Price
  • $1,206/SF
  • 115 Days On Market

  Last Sold Price $1,055,000

  Last Listing Agent Cheri Mason LandVest MV
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  /28

  $1,799,000

  • 4 Beds
  • 2.5 Baths
  • 3,268 Sq Ft

  7 Upper Meadow Ln, Oak Bluffs, MA 02557

  Meadowview Farms -- This home is ideal for those who love to host lively gatherings! Set at the end of a quiet cul-de-sac, this spacious Colonial offers over 3,200 sq ft designed for comfortable living and easy entertaining. The home features four bedrooms and 2.5 baths, including a primary suite with walk-in closets and private bath. The main living area flows from a living room with fireplace

  Lesley Heidt Sandpiper Realty Inc

  7 Upper Meadow Ln, Oak Bluffs, MA 02557
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  /30

  $28,500 total monthly price

  • 9 Beds
  • 6.5 Baths
  • 3,500 Sq Ft
  • House for Rent

  9 Tuckernuck Ave, Oak Bluffs, MA 02557

  **SHORT TERM ONLY - WEEKLY RATE ADVERTISED ** Water view Victorian fronting Waban Park, steps to Inkwell Beach. Newly restored 9-bed, 6+ bath Main and Guest House houses 18 guests. Internet, A/C and cable TV. Coastal chic interior with all new furnishings. Large open floor plan, ample gathering and relaxation spaces. Dining for 10, Wet Bar, gourmet kitchen, gas range, stainless appliances and

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  9 Tuckernuck Ave, Oak Bluffs, MA 02557
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  /21

  $982,000 Sold Dec 19, 2025

  25 Windy Hill Rd, Oak Bluffs, MA 02557

  • 3 Beds
  • 1 Bath
  • 980 Sq Ft
  • Built 1971

  Last Sold Summary

  • 1% Below List Price
  • $1,002/SF
  • 10 Days On Market

  Current Estimated Value $969,547

  Last Listing Agent Rene Jackson Island Real Estate

  25 Windy Hill Rd, Oak Bluffs, MA 02557
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  /34

  Est $1,136,715 Not Listed For Sale

  2 Nahomon St, Oak Bluffs, MA 02557

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 1978

  2 Nahomon St, Oak Bluffs, MA 02557

  Last Sold Summary

  • 20% Above List Price
  • $731/SF
  • 87 Days On Market

  Last Sold Price $950,000

  Last Listing Agent Jarrod Smith Romano Real Estate
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  /37

  $1,750,000 Pending

  • 4 Beds
  • 3 Baths
  • 3,058 Sq Ft

  2 Farm Path, Oak Bluffs, MA 02557

  "Turn-key" offering! This custom cape design with a delightful farmer's porch provides ample opportunities to entertain. Set upon nearly an acre of level and landscaped land with irrigation, it abuts the State Forrest, has an open floor plan with cathedral ceilings and skylights. The three bedroom main, has A/C, a finished basement rec room, a large rear deck that spills forth onto a large yard

  Sean Federowicz Landmarks at TODAY Real Estate

  2 Farm Path, Oak Bluffs, MA 02557
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  /10

  $20,000 total monthly price

  • 5 Beds
  • 3 Baths
  • 2,352 Sq Ft
  • House for Rent

  55 Samoset Ave Unit 1, Oak Bluffs, MA 02557

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated, Great for Family Gatherings, Corporate Retreats, Central Air & Heat, very close to Circuit Ave and Beach, 5 Bedrooms, 3 full baths, galley kitchen, new appliances, dining room, family room, Flat Screen TV, FREE Wifi, washer & dryer, bay window breakfast nook, Oak and Pine wood flooring, outdoor shower, wrap around porch, blue stone

  Karen Overtoom Karen M. Overtoom R.E.

  55 Samoset Ave Unit 1, Oak Bluffs, MA 02557
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  /4

  $1,350,000 Sold Aug 15, 2025

  35 Vineyard Avenue Extension, Oak Bluffs, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,864 Sq Ft
  • Built 1970

  Last Sold Summary

  • 7% Below List Price
  • $724/SF
  • 12 Days On Market

  Last Listing Agent Lesley Heidt Sandpiper Realty Inc

  35 Vineyard Avenue Extension, Oak Bluffs, MA 02568
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  /3

  Est $1,591,742 Not Listed For Sale

  18 Towanticut Ave, Oak Bluffs, MA 02557

  • 4 Beds
  • 2.5 Baths
  • 2,329 Sq Ft
  • Built 1989

  18 Towanticut Ave, Oak Bluffs, MA 02557

  Last Sold Summary

  • 6% Above List Price
  • $644/SF
  • 13 Days On Market

  Last Sold Price $1,500,000

  Last Listing Agent Brenda Galligan Karen M. Overtoom R.E.
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  /39

  $1,800,000

  • 4 Beds
  • 3 Baths
  • 2,064 Sq Ft

  18 Wood Duck Way, Edgartown, MA 02539

  Being sold turnkey and fully furnished, this modern home has four bedrooms and three full baths. Large windows and high ceilings, the home lets in bright natural light. The first floor has three bedrooms and a full bath with double sinks. Beautiful oak and maple floors complement the cherry stairs and living room built-ins. Open concept second level contains the open concept kitchen, living room,

  Janna O'Loughlin Portfolio Properties

  18 Wood Duck Way, Edgartown, MA 02539
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  /29

  $64,000 total monthly price

  • 4 Beds
  • 7 Baths
  • 3,600 Sq Ft
  • House for Rent

  385 Barnes Rd Ob534, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $18,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is a beautiful waterfront home with a pool on the Lagoon. Enter through the impressive foyer with water views over the pool and lawn. There is a large living room with cathedral ceilings and dining area on the main level. There is a gourmet kitchen with eat-in

  Karen Overtoom Karen M. Overtoom R.E.

  385 Barnes Rd Ob534, Oak Bluffs, MA 02557
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  /19

  $1,865,000 Sold Dec 04, 2025

  71 Netock Ave, Oak Bluffs, MA 02557

  • 4 Beds
  • 5 Baths
  • 2,820 Sq Ft
  • Built 1982

  Last Sold Summary

  • 7% Below List Price
  • $661/SF
  • 11 Days On Market

  Current Estimated Value $1,891,636

  Last Listing Agent Ellen Valentgas Sotheby's International Realty

  71 Netock Ave, Oak Bluffs, MA 02557
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  /5

  Not Listed For Sale

  0 Bridle Path Rd, Vineyard Haven, MA 02568

  0 Bridle Path Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 7 Days On Market

  Last Sold Price $885,000

  Last Listing Agent Diana Gilmore Island Real Estate
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  /23

  $2,260,000

  • 4 Beds
  • 3.5 Baths
  • 2,810 Sq Ft

  4 High Meadow Ln, Oak Bluffs, MA 02557

  Classic Post & Beam set in Meadow View FarmsThis bright and charming four-bedroom home sits on almost an acre of land with endless possibilities and impressive touches throughout.The farmer's porch overlooks an expansive front lawn and offers a warm welcome. The open first floor is sunny with cathedral ceilings and gas fireplace with stonework. The kitchen features granite countertops, Wolf

  Kate Burnside Portfolio Properties

  4 High Meadow Ln, Oak Bluffs, MA 02557
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  /20

  $20,000 total monthly price

  • 3 Beds
  • 3 Baths
  • House for Rent

  40 Hidden Cove Rd, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Welcome to "Shangri-la" A beautiful townhouse condominium end unit with magnificent views. Located midway between Oak Bluffs and Edgartown. You can enjoy the beautiful pool or one of the close local beaches. You will want to sit and enjoy the water views on the deck. The townhouse has a great living room with views and bedrooms

  Karen Overtoom Karen M. Overtoom R.E.

  40 Hidden Cove Rd, Oak Bluffs, MA 02557
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  /32

  $1,100,000 Sold Jun 27, 2025

  10 Kims Way, Oak Bluffs, MA 02568

  • 4 Beds
  • 2.5 Baths
  • 1,976 Sq Ft
  • Built 1985

  Last Sold Summary

  • 12% Below List Price
  • $557/SF
  • 156 Days On Market

  Last Listing Agent Michael Schweikert Ocean Park Realty, Inc.

  10 Kims Way, Oak Bluffs, MA 02568
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  /38

  Est $1,034,721 Not Listed For Sale

  287 County Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft
  • Built 1998

  287 County Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 22% Above List Price
  • $759/SF
  • 10 Days On Market

  Last Sold Price $850,000

  Last Listing Agent Jill Napior Tea Lane Associates
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  /24

  $2,195,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,262 Sq Ft

  30 Sengekontacket Rd, Oak Bluffs, MA 02557

  Secluded island retreat nestled above the trees! Located in the desirable Sengekontacket Association, this four-bedroom, three-bathroom home offers stunning views of acres of conservation land, Sengekontacket Pond, and Nantucket Sound. Perched on a hillside, the house provides utmost privacy from all rooms while being just a short walk from the Association boat ramp and kayak storage. The main

  Cassie Bradley Wallace & Co. Sotheby's International Realty

  30 Sengekontacket Rd, Oak Bluffs, MA 02557
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  /25

  $24,000 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,257 Sq Ft
  • House for Rent

  5 Laurel Ave, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Wonderful, fully redecorated Gingerbread house on East Chop, just minutes from the excitement of Oak Bluffs. There are three bedrooms and two full baths. The interior is clean and crisp, with beach cottage décor and beautiful bamboo floors. Entertainment options include

  Karen Overtoom Karen M. Overtoom R.E.

  5 Laurel Ave, Oak Bluffs, MA 02557
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  /42

  $1,700,000 Sold Nov 03, 2025

  35 Tower Ridge Rd, Oak Bluffs, MA 02557

  • 3 Beds
  • 4 Baths
  • 2,558 Sq Ft
  • Built 1986

  Last Sold Summary

  • 20% Below List Price
  • $665/SF
  • 118 Days On Market

  Current Estimated Value $1,741,804

  Last Listing Agent Katherine Donahue Sandpiper Realty Inc

  35 Tower Ridge Rd, Oak Bluffs, MA 02557
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  /17

  Est $1,541,098 Not Listed For Sale

  19 Quantapog Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 3 Baths
  • 2,298 Sq Ft
  • Built 1988

  19 Quantapog Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 12% Above List Price
  • $601/SF
  • 22 Days On Market

  Last Sold Price $1,380,000

  Last Listing Agent Leslie Floyd Portfolio Real Estate Inc.
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  /37

  $1,825,000 Pending

  • 4 Beds
  • 3 Baths
  • 3,142 Sq Ft

  7 S Meadow Ln, Oak Bluffs, MA 02557

  Impressive four-bedroom home with a distinctive floor plan that combines privacy, comfort, and convenience in one of Oak Bluffs’ most desirable locations. The main living area, filled with natural light and soaring ceiling, offers an open layout that is warm and inviting. A third floor den and exterior decks on all levels provide ample living space both indoors and out. Set within the

  Katie Donahue Sandpiper Realty

  7 S Meadow Ln, Oak Bluffs, MA 02557
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  /30

  $20,000 total monthly price

  • 4 Beds
  • 2 Baths
  • 1,920 Sq Ft
  • House for Rent

  291 Barnes Rd Ob516, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Feel the ocean breezes from this classic waterfront home. There are four bedrooms, an open living room and dining room that open up to large deck overlooking beautiful views across the Lagoon. Walking path to private sandy beach. BOAT MOORING INCLUDED.

  Karen Overtoom Karen M. Overtoom R.E.

  291 Barnes Rd Ob516, Oak Bluffs, MA 02557
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  /30

  $1,995,000 Sold Aug 29, 2025

  26 Box Turtle Ln, Oak Bluffs, MA 02557

  • 4 Beds
  • 3.5 Baths
  • 2,891 Sq Ft
  • Built 1980

  Last Sold Summary

  • $690/SF
  • 5 Days On Market

  Current Estimated Value $2,267,004

  Last Listing Agent Jayne Isford Ocean Park Realty Inc

  26 Box Turtle Ln, Oak Bluffs, MA 02557
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  /12

  Est $1,235,062 Not Listed For Sale

  3 Carole Ave, Vineyard Haven, MA 02568

  • 4 Beds
  • 2 Baths
  • 1,997 Sq Ft
  • Built 1985

  3 Carole Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 7% Above List Price
  • $576/SF
  • 209 Days On Market

  Last Sold Price $1,150,000

  Last Listing Agent Bob Sparks American Real Estate LLC
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  /9

  $2,250,000

  • 3 Beds
  • 3.5 Baths
  • 2,475 Sq Ft

  35 Double Ox Rd, Oak Bluffs, MA 02557

  Would you love to live or vacation in a brand-new home on Martha’s Vineyard?We have the LOCATION, REPUTABLE LONG-STANDING BUILDER & PROVEN TRACK RECORD!Come take a tour of the newest home under construction in the Lagoon Ridge neighborhood.Easy to show – Call now! To be built with lot purchase$700,000 and building contract $1,550,000.This 3-bedroom dream home is set in an elevated

  Marilyn Moses Ocean Park Realty Inc

  35 Double Ox Rd, Oak Bluffs, MA 02557
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  /14

  $14,200 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • House for Rent

  59 Prospect Ave Ob502, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. This immaculate home is located in a quiet neighborhood that is just a bike ride's distance from several lovely beaches as well as the center of Oak Bluffs. The home offers open living spaces, generously proportioned sunny bedrooms and is well equipped.

  Karen Overtoom Karen M. Overtoom R.E.

  59 Prospect Ave Ob502, Oak Bluffs, MA 02557
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  $899,000 Sold Jul 11, 2025

  8 Rock Ave, Oak Bluffs, MA 02557

  • 3 Beds
  • 1.5 Baths
  • 955 Sq Ft
  • Built 1871

  Last Sold Summary

  • $941/SF
  • 6 Days On Market

  Current Estimated Value $924,470

  Last Listing Agent Marilyn Moses Ocean Park Realty Inc

  8 Rock Ave, Oak Bluffs, MA 02557
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  /13

  Est $1,188,703 Not Listed For Sale

  33 Menahan St, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft
  • Built 1993

  33 Menahan St, Vineyard Haven, MA 02568

  Last Sold Summary

  • $830/SF
  • 48 Days On Market

  Last Sold Price $1,185,000

  Last Listing Agent Katherine Donahue Sandpiper Realty Inc
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  /30

  $2,950,000

  • 3 Beds
  • 2.5 Baths
  • 1,845 Sq Ft

  33 Ocean Ave, Oak Bluffs, MA 02557

  A rare offering on iconic Ocean Park. This beautifully renovated Victorian cottage sits in the heart of historic Oak Bluffs with unencumbered views of Ocean Park and Vineyard Sound. Completely rebuilt in 2024, this 3-bedroom, home blends classic Vineyard charm with modern comforts, featuring a welcoming wraparound porch, a beach-stone wood-burning fireplace, new kitchen, baths, windows, doors and

  Marcia Sullivan Garvey Donnelly + Co.

  33 Ocean Ave, Oak Bluffs, MA 02557
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  /34

  $980,000 Sold Mar 26, 2025

  11 Fairway Dr, Oak Bluffs, MA 02557

  • 2 Beds
  • 1 Bath
  • 1,608 Sq Ft
  • Built 1969

  Last Sold Summary

  • 18% Below List Price
  • $609/SF
  • 191 Days On Market

  Current Estimated Value $1,077,844

  Last Listing Agent Sandra Grymes Martha's Vineyard Island-Wide Realty

  11 Fairway Dr, Oak Bluffs, MA 02557
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  /14

  Est $984,867 Not Listed For Sale

  51 Manchester Ave, Vineyard Haven, MA 02568

  • 2 Beds
  • 1 Bath
  • 1,024 Sq Ft
  • Built 1978

  51 Manchester Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 3% Above List Price
  • $933/SF
  • 22 Days On Market

  Last Sold Price $955,000

  Last Listing Agent Roy Cutrer LAER Realty Partners
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  /28

  $1,595,000

  • 3 Beds
  • 1.5 Baths
  • 2,448 Sq Ft

  38 Rogers Way, Oak Bluffs, MA 02557

  Tucked away in a private desirable Oak Bluffs neighborhood yet only minutes from the charm of downtown and the incredible OB beaches, this home is a wonderful island retreat. The neighborhood is a must see to fully appreciate this property. With four levels of finished living space, it offers room to gather, relax, entertain in any season. Hardwood floors, open concept kitchen and living areas,

  Jon Hartzband Martha's Vineyard Island-Wide Realty

  38 Rogers Way, Oak Bluffs, MA 02557

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