20+ Homes for Sale in Oak Bluffs, MA

21 results

21 homes are for sale in Oak Bluffs, MA (median list price $1,755,000), as of November 4, 2026.

$1,699,000

38 Meadow View Road, Oak Bluffs, MA 02557

4 bds
|
2.5 ba
|
1957 sqft

$868/sqft · 6 days on market

MLS® 73596828Single Family Residence
Compass - Jennifer Dasilva

$5,225,000

Price reduced by

4 Canonicus Ave, Oak Bluffs, MA 02557

6 bds
|
4 ba
|
2890 sqft

$1,808/sqft · 497 days on market

MLS® 73472922Single Family Residence
Sandpiper Realty, Inc. - Katie Donahue & Rachel Serwa Group

$1,950,000

25 Oak Avenue, Oak Bluffs, MA 02557

2 bds
|
2 ba
|
1459 sqft

$1,337/sqft · 15 days on market

MLS® 73593599Single Family Residence
Sandpiper Realty, Inc. - Lisa Stewart
Property at 59 Tuckernuck Ave, Oak Bluffs, MA 02557
1 / 41
Active Under Contract
Price drop

$2,595,000

Price reduced by

59 Tuckernuck Ave, Oak Bluffs, MA 02557

4 bds
|
2.5 ba
|
1858 sqft

$1,397/sqft · 106 days on market

MLS® 73553801Single Family Residence
Compass - Jennifer Dasilva
Property at 19 Perkins Avenue, Oak Bluffs, MA 02557
1 / 14
Active Under Contract
Price drop

$799,000

Price reduced by

19 Perkins Avenue, Oak Bluffs, MA 02557

2 bds
|
1 ba
|
985 sqft

$811/sqft · 168 days on market

MLS® 73522647Single Family Residence
Sandpiper Realty, Inc. - Katie Donahue & Rachel Serwa Group

What's actually happening in Oak Bluffs right now?

Forget the national headlines. Get the hyper-local, street-level data on inventory, price drops, and true market value before you make an offer.

Property at 61 Canonicus Ave, Oak Bluffs, MA 02557
1 / 41
Active Under Contract

$2,200,000

61 Canonicus Ave, Oak Bluffs, MA 02557

3 bds
|
2.5 ba
|
2420 sqft

$909/sqft · 52 days on market

MLS® 73576858Single Family Residence
Donnelly + Co. - Kristin Buck

$1,595,000

Price reduced by

20 Hidden Cove, Oak Bluffs, MA 02557

4 bds
|
3 ba
|
1898 sqft

$840/sqft · 51 days on market

MLS® 73577547Single Family Residence
Compass - Jennifer Dasilva

$1,399,000

Price reduced by

7 Ploughshare Lane, Oak Bluffs, MA 02557

3 bds
|
2.5 ba
|
1645 sqft

$850/sqft · 157 days on market

MLS® 73527741Single Family Residence
Sandpiper Realty, Inc. - Emma Kennedy

$4,395,000

267 Barnes Road, Oak Bluffs, MA 02557

3 bds
|
5.5 ba
|
4046 sqft

$1,086/sqft · 58 days on market

MLS® 73572956Single Family Residence
Donnelly + Co. - Stephanie Roache
Property at 33 Vineyard Ave, Oak Bluffs, MA 02557
1 / 38
Active
Price drop
Open

$1,695,000

Price reduced by

33 Vineyard Ave, Oak Bluffs, MA 02557

3 bds
|
2.5 ba
|
1431 sqft

$1,184/sqft · 185 days on market

MLS® 73511961Single Family Residence
Douglas Elliman Real Estate - Nantucket - Allison Cameron Parry

$1,375,000

234 County Road, Oak Bluffs, MA 02557

5 bds
|
2 ba
|
1952 sqft

$704/sqft · 45 days on market

MLS® 73580264Single Family Residence
Sandpiper Realty, Inc. - Emma Kennedy

$1,495,000

Price reduced by

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

3 bds
|
3.5 ba
|
2739 sqft

$546/sqft · 124 days on market

MLS® 73544610Single Family Residence
Wallace & Co. Sotheby's International Realty - Rose Ryley

$2,595,000

Price reduced by

44 Tiffany Dr, Oak Bluffs, MA 02557

4 bds
|
4.5 ba
|
3927 sqft

$661/sqft · 159 days on market

MLS® 73527128Single Family Residence
MV Luxury Homes LLC - Perry Patterson

$1,755,000

68 Front Street, Oak Bluffs, MA 02557

3 bds
|
3 ba
|
2815 sqft

$623/sqft · 53 days on market

MLS® 73576389Single Family Residence
Wallace & Co. Sotheby's International Realty - Alyssa Halisky

$5,100,000

7 Overview Lane, Oak Bluffs, MA 02557

0 bds
|
0 ba
|
-- sqft

202 days on market

MLS® 73503350Residential
Wallace & Co. Sotheby's International Realty - Alyssa Halisky

$3,100,000

Price reduced by

6 Brewster Ave, Oak Bluffs, MA 02557

4 bds
|
3 ba
|
1728 sqft

$1,794/sqft · 430 days on market

MLS® 73472925Single Family Residence
Sandpiper Realty, Inc. - Katie Donahue & Rachel Serwa Group

$789,000

24 Towanticut St, Oak Bluffs, MA 02568

0 bds
|
0 ba
|
-- sqft

106 days on market

MLS® 73568028Residential
Alisan Lohan - Conway Properties - Alisan Lohan Conway

$549,000

Price reduced by

112 Dukes County, Oak Bluffs, MA 02557

0 bds
|
0 ba
|
-- sqft

246 days on market

MLS® 73482521Other
Wallace & Co. Sotheby's International Realty - Rose Ryley

$975,000

68 Pond View Drive, Oak Bluffs, MA 02557

0 bds
|
0 ba
|
-- sqft

116 days on market

MLS® 73548450Residential
Sandpiper Realty, Inc. - Casandra Hyland

$4,600,000

Price reduced by

15 Tamarack Lane, Oak Bluffs, MA 02557

6 bds
|
5.5 ba
|
3998 sqft

$1,151/sqft · 167 days on market

MLS® 73522816Single Family Residence
Donnelly + Co. - Stephanie Roache

$3,400,000

27 Double Ox Rd, Oak Bluffs, MA 02557

3 bds
|
4.5 ba
|
3260 sqft

$1,043/sqft · 132 days on market

MLS® 73542323Single Family Residence
Sandpiper Realty, Inc. - Lesley Heidt

Homes for sale in Oak Bluffs, MA: market at a glance

As of November 4, 2026, there are 21 homes for sale in Oak Bluffs, MA, with a median list price of $1,755,000. In August 2026, the median sale price for homes in Oak Bluffs, MA was $1,875,000.

Homes for sale
21
Median list price
$1,755,000
Median sale price (August 2026)
$1,875,000
Median days on market (August 2026)
124 days

Common questions about Oak Bluffs, MA real estate

How many homes are for sale in Oak Bluffs, MA?

As of November 4, 2026, there are 21 homes for sale in Oak Bluffs, MA, including 17 single-family homes.

What is the median home price in Oak Bluffs, MA?

The median list price of homes for sale in Oak Bluffs, MA is $1,755,000. Homes that sold in August 2026 had a median sale price of $1,875,000.

How long do homes take to sell in Oak Bluffs, MA?

Homes in Oak Bluffs, MA that sold in August 2026 had a median of 124 days on market. Homes currently for sale show a median of about 79 days on market.