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ZIP Code: 02557
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26 Properties Available

26 Properties Available

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9 Brunswick, Oak Bluffs, MA 02557
1/36
Pending

$1,275,000

3 Beds1 Bath1,033 SqFt

9 Brunswick, Oak Bluffs, MA 02557

Listed by Alice Pierce of Coldwell Banker Realty - Hingham

59 Tuckernuck Ave, Oak Bluffs, MA 02557
1/41
New

$2,650,000

4 Beds2.5 Baths1,858 SqFt

59 Tuckernuck Ave, Oak Bluffs, MA 02557

Listed by Jennifer DaSilva of Compass

28 Beach Rd, Oak Bluffs, MA 02557
1/40
New

$3,675,000

4 Beds2.5 Baths1,800 SqFt

28 Beach Rd, Oak Bluffs, MA 02557

Listed by Wendy Harman of Compass

26 Winthrop Ave, Oak Bluffs, MA 02557
1/28
Active

$839,000

1 Bed1 Bath804 SqFt

26 Winthrop Ave, Oak Bluffs, MA 02557

Listed by Alisan Lohan - Conway of Alisan Lohan - Conway Properties

82 Pennsylvania Avenue, Oak Bluffs, MA 02557
1/13
Active

$1,296,000

3 Beds1.5 Baths1,144 SqFt

82 Pennsylvania Avenue, Oak Bluffs, MA 02557

Listed by Emma Kennedy of Sandpiper Realty, Inc.

40 Hidden Cove Road Unit 2 #2, Oak Bluffs, MA 02557
1/28
Active

$1,595,000

3 Beds3.5 Baths2,739 SqFt

40 Hidden Cove Road Unit 2 #2, Oak Bluffs, MA 02557

Listed by Rose Ryley of Wallace & Co. Sotheby's International Realty

27 Double Ox Rd, Oak Bluffs, MA 02557
1/12
Active

$3,400,000

3 Beds4.5 Baths3,260 SqFt

27 Double Ox Rd, Oak Bluffs, MA 02557

Listed by Lesley Heidt of Sandpiper Realty, Inc.

27 Laurel Avenue, Oak Bluffs, MA 02557
1/39
Active

$1,575,000

3 Beds3 Baths1,621 SqFt

27 Laurel Avenue, Oak Bluffs, MA 02557

Listed by Lisa Sheehan of Berkshire Hathaway HomeServices Robert Paul Properties

18 Puritan Dr, Oak Bluffs, MA 02557
1/42
Pending

$1,895,000

5 Beds3.5 Baths2,527 SqFt

18 Puritan Dr, Oak Bluffs, MA 02557

Listed by Jennifer DaSilva of Compass

312 East Chop Drive, Oak Bluffs, MA 02557
1/37
Active

$2,295,000

3 Beds3 Baths1,425 SqFt

312 East Chop Drive, Oak Bluffs, MA 02557

Listed by Alyssa Halisky of Wallace & Co. Sotheby's International Realty

7 Ploughshare Lane, Oak Bluffs, MA 02557
1/33
Active

$1,599,000

3 Beds2.5 Baths1,645 SqFt

7 Ploughshare Lane, Oak Bluffs, MA 02557

Listed by Emma Kennedy of Sandpiper Realty, Inc.

44 Tiffany Dr, Oak Bluffs, MA 02557
1/15
Price Dropped by $100K

$2,800,000

4 Beds4.5 Baths3,927 SqFt

44 Tiffany Dr, Oak Bluffs, MA 02557

Listed by Perry Patterson of MV Luxury Homes LLC

3 Troy Street, Oak Bluffs, MA 02557
1/26
Active

$1,349,000

3 Beds2 Baths1,863 SqFt

3 Troy Street, Oak Bluffs, MA 02557

Listed by Alyssa Halisky of Wallace & Co. Sotheby's International Realty

15 Tamarack Lane, Oak Bluffs, MA 02557
1/42
Price Dropped by $350K

$4,600,000

6 Beds5.5 Baths3,998 SqFt

15 Tamarack Lane, Oak Bluffs, MA 02557

Listed by Stephanie Roache of Donnelly + Co.

19 Perkins Avenue, Oak Bluffs, MA 02557
1/14
Active

$825,000

2 Beds1 Bath985 SqFt

19 Perkins Avenue, Oak Bluffs, MA 02557

Listed by Katie Donahue & Rachel Serwa Group of Sandpiper Realty, Inc.

22 Firehouse, Oak Bluffs, MA 02557
1/14
Pending

$950,000

2 Beds1 Bath1,074 SqFt

22 Firehouse, Oak Bluffs, MA 02557

Listed by Jen O'Hanlon of Compass

33 Vineyard Ave, Oak Bluffs, MA 02557
1/32
Open Sat 9:30AM-11:30AM

$1,995,000

3 Beds2.5 Baths1,431 SqFt

33 Vineyard Ave, Oak Bluffs, MA 02557

Listed by Allison Cameron Parry of Douglas Elliman Real Estate - Nantucket

22 Old Harbor Lane, Oak Bluffs, MA 02557
1/26
Active

$1,850,000

4 Beds2 Baths1,833 SqFt

22 Old Harbor Lane, Oak Bluffs, MA 02557

Listed by Lisa Stewart of Sandpiper Realty, Inc.

26 Sea Glen Road, Oak Bluffs, MA 02557
1/39
Price Dropped by $100K

$1,495,000

4 Beds3 Baths1,514 SqFt

26 Sea Glen Road, Oak Bluffs, MA 02557

Listed by Jennifer DaSilva of Compass

3 Hidden Cove Rd, Oak Bluffs, MA 02557
1/41
Pending

$2,295,000

4 Beds3.5 Baths3,016 SqFt

3 Hidden Cove Rd, Oak Bluffs, MA 02557

Listed by Wendy Harman of Compass

8 Paddock Rd, Oak Bluffs, MA 02557
1/41
Active

$5,450,000

4 Beds5.5 Baths3,300 SqFt

8 Paddock Rd, Oak Bluffs, MA 02557

Listed by Lesley Heidt of Sandpiper Realty, Inc.

385 Barnes Road, Oak Bluffs, MA 02557
1/42
Price Dropped by $200K

$5,295,000

3 Beds5.5 Baths3,608 SqFt

385 Barnes Road, Oak Bluffs, MA 02557

Listed by Stephanie Roache of Donnelly + Co.

16 Frog Hollow, Tisbury, MA 02557
1/27
Active

$4,695,000

3 Beds2 Baths1,716 SqFt

16 Frog Hollow, Tisbury, MA 02557

Listed by Rose Ryley of Wallace & Co. Sotheby's International Realty

3 Kims Way, Oak Bluffs, MA 02557
1/25
Price Dropped by $40K

$1,155,000

3 Beds2 Baths1,164 SqFt

3 Kims Way, Oak Bluffs, MA 02557

Listed by Alyssa Halisky of Wallace & Co. Sotheby's International Realty

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Michael Peppino
+1(617) 875-4352
michaelpeppino@gmail.com
1151 Washington St, Braintree, MA 02184-5439, USA
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      South Shore Real Estate
IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

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Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

Real Logo Solid Knockout Black

Get My App

Real Brokerage
Michael Peppino
+1(617) 875-4352
michaelpeppino@gmail.com
1151 Washington St, Braintree, MA 02184-5439, USA
      Buy
      1. All Listings
      2. Featured Listings
      3. Sold Listings
      4. Neighborhoods
      5. Calculator
      Sell
      1. Sell My Home
      2. Home Valuation
      3. Reviews
      4. Market Snapshot
      5. Contact Us
      6. Real Estate Resources
      South Shore Real Estate
IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility