Oak Bluffs Homes under $350,000

Welcome to Oak Bluffs, a charming town nestled on Martha's Vineyard in Dukes County, Massachusetts. Known for its vibrant community, stunning beaches, and rich history, Oak Bluffs offers a unique blend of small-town charm and coastal living. As a popular summer destination, the town is famous for its colorful gingerbread cottages, lively harbor, and the iconic Flying Horses Carousel, making it a delightful place to call home.

For those looking to embrace the Oak Bluffs lifestyle without breaking the bank, there are fantastic opportunities available with homes priced under $350,000. This market offers a variety of options, from cozy cottages perfect for weekend getaways to quaint bungalows ideal for year-round living. With the right real estate guidance, you can find a hidden gem that suits your needs and budget.

Imagine waking up to the sound of the ocean waves, enjoying fresh seafood from local eateries, or taking leisurely strolls along the picturesque beaches. Oak Bluffs is not just a place to live; it's a lifestyle filled with outdoor adventures, cultural experiences, and a close-knit community.

With homes available at an affordable price point, you can invest in your dream of living in this idyllic coastal town. Whether you're a first-time homebuyer, looking for a vacation retreat, or seeking a peaceful community to settle down in, Oak Bluffs has something for everyone. Discover the charm of Oak Bluffs today and start your journey toward homeownership in this beautiful part of Massachusetts!

Newest Oak Bluffs Homes under $350,000

$287,500

1 Beds ⋅ 1 Baths ⋅ 22604264 MLS

Welcome to 27 Island Inn, Unit 9C, an inviting Martha's Vineyard retreat offering the perfect combination of personal enjoyment and rental opportunity. This comfortable studio accommodates up to four guests with two double beds, a full bath, kitchenette with a 2-burner cooktop, cable TV and free WiFi. A unique opportunity is adjoining Unit 10C, a separate 1-bedroom, 1-bath suite accommodating up to four guests with a queen bed, sofa bed, cozy living area, well-equipped kitchenette with 2-burner cooktop, and patio/deck. Units 9C and 10C can be enjoyed separately or together through the adjoining door. Each is being offered for sale separately, with the opportunity to purchase both together—ideal for additional family, guests or expanded rental possibilities. Island Inn is a seasonal resort, open April through October, offering a relaxed, pet-friendly setting with a heated outdoor pool, 3 association clay tennis courts, grilling areas, fire pits and spacious grounds. Directly next door is the popular and pet-friendly Noman's, offering outdoor dining, cocktails, lawn games and entertainment. Ideally located between Oak Bluffs and Edgartown, you're minutes from beaches, golf, shops, restaurants, ferries and Oak Bluffs Harbor. On-site Gulph Creek Management handles virtually every aspect of the rental operation, including bookings, guest coordination, cleaning, repairs and maintenance. Just bring your luggage and enjoy your piece of paradise! Ideal as a Vineyard getaway, investment, or combination of personal use and rental income. Showings during turnovers only, 10AM-3PM. Proof of funds required.

27 Island Inn Road, Oak Bluffs

$310,000

1 Beds ⋅ 1 Baths ⋅ 22604263 MLS

Welcome to 27 Island Inn, Unit 10C, a comfortable one-bedroom, one-bath Martha's Vineyard retreat offering an ideal combination of personal enjoyment and rental opportunity. Accommodating up to four guests, 10C features a queen bedroom, sofa bed, cozy living area, well-equipped kitchenette. A unique feature is the adjoining door to Unit 9C, a studio with two double beds, full bath and kitchenette. Units 9C and 10C are being offered for sale separately, with the opportunity to purchase both together—perfect for extended family, guests, or expanded rental possibilities while still allowing each unit to be used independently. Island Inn is a seasonal resort, open April through October, offering a relaxed, pet-friendly setting with a heated outdoor pool, 3 association clay tennis courts, grilling areas, fire pits and spacious grounds. Directly next door is the popular pet-friendly Noman's, featuring outdoor dining, cocktails, lawn games and entertainment. Ideally located between Oak Bluffs and Edgartown, just minutes from beaches, golf, shops, restaurants, ferries and Oak Bluffs Harbor. On-site Gulph Creek Management handles virtually every aspect of the rental operation, including bookings, guest coordination, cleaning, repairs and maintenance. Just bring your luggage and enjoy your piece of paradise! Ideal as a Vineyard getaway, investment, or combination of personal use and rental income. Showings during turnovers only, 10AM-3PM. Proof of funds required.

27 Island Inn Road, Oak Bluffs

$260,000

1 Beds ⋅ 1 Baths ⋅ 22604259 MLS

Welcome to 27 Island Inn, Unit 25F, a comfortable studio offering the perfect combination of a Martha's Vineyard getaway and rental opportunity. Accommodating up to four guests, this inviting unit features two double beds, one full bath, a convenient kitchenette, cable TV and free WiFi. Island Inn is a seasonal resort, open April through October, offering a relaxed, pet-friendly setting with a heated outdoor pool, 3 association clay tennis courts, grilling areas, fire pits and spacious grounds. Directly next door is the popular pet-friendly Noman's, featuring outdoor dining, cocktails, lawn games and entertainment. Ideally located between Oak Bluffs and Edgartown, just minutes from beaches, golf, shops, restaurants, ferries and Oak Bluffs Harbor. On-site Gulph Creek Management handles virtually every aspect of the rental operation, including bookings, guest coordination, cleaning, repairs and maintenance, making ownership easy and convenient. Just bring your luggage and enjoy your piece of paradise! Ideal as a Vineyard getaway, investment, or combination of personal use and rental income. Showings during turnovers only, 10AM-3PM. Proof of funds required.

33 Island Inn Road, Oak Bluffs

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