Oak Bluffs, Massachusetts listings for sale


$1,449,000 - Oak Bluffs, MA

14 High Meadow Lane Oak Bluffs, MA - MEADOW VIEW FARM/OAK BLUFFS - Owned by the same family for over 30 years, this sun-drenched, contemporary reverse-style home is located in Meadow View Farms. Well-maintained over those years, this 3 bedroom, 2 full and 2 half baths multi-level home has so much to offer and boundless potential. The second-level features a bright, open floor plan with cathedral ceilings and 3 sliding doors that take you out to the upper deck. Open the sliders to the expansive deck and you almost double the living space on the upper level. There is also a powder room on the upper level. The first floor features the primary suite with bath, walk-in closet, air conditioning, and sliders that open to the first-floor deck. There are 2 more spacious bedrooms and a shared bath. Venture down to the above-grade lower-level and enjoy the family room, reading nook, and bonus room. There is also a large storage/utility room with a second power room. This space opens to the 1-car garage. Like every true island home, there is an outdoor shower. Plenty of additional storage under the deck. Air conditioning on the upper level and the first floor primary bedroom. Solar panels were added in the fall of 2023. With 3 floors of living space and an expansive portion of the land behind it, this property offers so much potential for the next owners. Meadow View Farms Association is a neighborhood less than 2 miles from downtown Oak Bluffs featuring paved roads, tennis, open meadows, and even mail delivery. The septic has passed the Title V inspection for 3 bedrooms. An interested buyer should speak to an engineer about expanding the size of the septic to accommodate more bedrooms or the possibility of adding a pool. The home has been well-maintained throughout its single-family ownership and it is being sold ''as is''.
1987 | 3 | 2 | 2,528 sqft.
$1,189,000 - Oak Bluffs, MA

96 Manchester Avenue Oak Bluffs, MA - Nestled in a quiet area of town less than 2 miles from Circuit Avenue is this contemporary Cape Style house waiting for you to make it your home. Enter from the Farmer's Porch into the living area with cathedral ceilings. The open-concept design features a kitchen, dining, and living area. It is welcoming and allows you to gather together. There is a first floor bedroom. A full bath with laundry complete the main level. The second floor features a large bedroom with plenty of storage and a second smaller bedroom. Both share a full bath. There is an additional 400 sq. ft. of finished space in the lower-level not included in the listed square footage. There is also plenty of storage in the unfinished area of the basement. Beyond the sliding doors off of the dining area is the back yard where you will find an enormous outdoor shower, a feature truly cherished on the island. The generous corner lot has a gentle slope. Close to downtown, school, bike path, and beaches, this delightful home is perfect for year-round or seasonal living. ***PLEASE NOTE- Seller will either have the wood floors refinished or they will offer a credit at closing for you to have them done.
1999 | 3 | 2 | 1,996 sqft.
$1,169,999 - Oak Bluffs, MA

96 Manchester Ave Oak Bluffs, MA - Nestled in the sought-after Lagoon Heights in Oak Bluffs, 96 Manchester Ave is a charming Cape-style home offering a perfect blend of comfort and coastal charm. This well-maintained residence features three spacious bedrooms and two bathrooms. Recent updates enhance both style and functionality, including a new roof, numerous Andersen windows, an outdoor shower, and fresh interior paint. The inviting layout offers a bright and airy feel, complemented by ample natural light. Enjoy the peaceful surroundings while being just a short distance from the Lagoon, local shops, and restaurants. Whether you're looking for a year-round residence, a vacation retreat, or an investment property, this Oak Bluffs gem is a must-see!
1999 | 3 | 2 | 2,016 sqft.
$1,169,000 - Oak Bluffs, MA

96 Manchester Avenue Oak Bluffs, MA - Nestled in the sought-after Lagoon Heights in Oak Bluffs, 96 Manchester Ave is a charming Cape-style home offering a perfect blend of comfort and coastal charm. This well-maintained residence features three spacious bedrooms and two bathrooms. Recent updates enhance both style and functionality, including a new roof, numerous Andersen windows, an outdoor shower, and fresh interior paint. The inviting layout offers a bright and airy feel, complemented by ample natural light. Enjoy the peaceful surroundings while being just a short distance from the Lagoon, local shops, and restaurants. Whether you're looking for a year-round residence, a vacation retreat, or an investment property, this Oak Bluffs gem is a must-see!
1999 | 3 | 2 | 2,016 sqft.
$1,050,000 - Oak Bluffs, MA

249 County Road Oak Bluffs, MA - This charming Cape-style home is ideally located just over a mile from downtown Oak Bluffs, offering the perfect blend of relaxed living and convenience. The open and inviting layout features spacious first-floor living areas, complemented by high ceilings and wood floors. A versatile second-story loft space provides an additional nook, perfect for a home office. Fronting the bike bath, enjoy easy access to Oak Bluffs' vibrant Main Street, stunning beaches, and the ferry, making it an ideal spot to experience all the best of down-island living. The property is being sold as-is. Fiduciary responsibilities apply.
2005 | 1 | 2 | 1,401 sqft.
$995,000 - Oak Bluffs, MA

50 Canonicus Avenue Oak Bluffs, MA - Coming Soon! Loved by generations, this quintessential Vineyard cottage has been in the same family since its creation in 1900. Step back in time and enjoy easy cottage living of yesteryear with modern updates including newer windows and electrical. Nestled under mature trees and just .3 mile to Inkwell Beach, join this close-knit neighborhood and make this house your island home. Close to beach, town, bike path, and more, this home sits in a special location. It is also part of both the Cottage City and Copeland Districts. The property is over 100 years old but it is not on the MACRIS registry. Buyer should research the process for making major renovations. Septic is a cesspool and will need to be upgraded at a Buyer's expense and as part of the overall plan for the property. Being sold ''as is''. Interior photos to be added by 9/23.
1900 | 2 | 0 | 952 sqft.
$985,000 - Oak Bluffs, MA

37 Circuit Avenue Unit: 4 Oak Bluffs, MA - Downtown Oak Bluffs Located right in the heart of town. Unit #4 A penthouse condo with a semi-private rooftop deck (shared with unit 5 only). This spacious condo has a panoramic view of the town and surrounding waters sitting high above it all with outdoor seating and separate entrances from either condo. This solid deck adds a whole other dimension to this already desirable unit. The interior with it's custom wooden features and ships ladder to the deck gives it a nautical feel. It's surprisingly spacious with a living area, dining and separated kitchen. The primary bedroom is over 16' x 21'. Just off the hall is a tiled bathroom with glass enclosed shower and another bedroom. This space is perfect for year-round living or makes a great summer rental property with it's ideal location. No need for a vehicle with in-town living, beach, and access to all the Ferries within a few blocks.
1900 | 2 | 1 | 990 sqft.
$935,000 - Oak Bluffs, MA

37 Circuit Avenue Unit: 5 Oak Bluffs, MA - Downtown Oak Bluffs centrally located in the heart of Oak Bluffs. Steps from ferries, shops, restaurants and beaches from this penthouse condo. Escape the hustle and bustle on your semi private rooftop deck shared only with (unit 4 also for sale). Panoramic views of the Nantucket and Vineyard Sounds await you while you relax on the deck or enjoy dinner al fresco. The condo features all wood floors, air-conditioning, custom built-in with a open yet divided living area, a sleep alcove and wood staircase to the rooftop deck. The large bedroom has a sunny nook with a opening skylight. This condo is ideal for a year-round living, an escape from the city getaway, or would make a great vacation rental with no car needed. The $415 monthly fee includes, all electric, heat, and water. Plus building taxes and insurance.
1900 | 1 | 1 | 797 sqft.
$235,000 - Oak Bluffs, MA

27 Island Inn Road Unit: 12D Oak Bluffs, MA - Island Inn the quintessential ''condotel,'' for buyers who want their vacations and easy income too! This sale is for one unit. The very popular Island Inn offers grassy grounds, tennis, pool, charcoal grills, fire pits, playground and event hall - as well as oh-so easy access to State Beach and in-town Oak Bluffs. The compound is open six-plus months, from April till October. Unit 12, a fully equipped studio unit with easy ground level access, is located deep at the more peaceful end of the compound. The unit is offered fully furnished -- or upgrade to your own taste. Kick back on your patio with a beverage at the end of a long day of play. Or run the toddler about the lawn till bedtime. For a livelier evening: Hang out at family-friendly Noman's, just across the lawn. Note: Showings inside the unit are scheduled only between tenants.
1979 | 0 | 0 | 329 sqft.