Oak Bluffs town, MA - homes for sale

49 of 49 results displayed

New
$1,755,000Active
3 beds 32 baths2,815 sq. ft.
68 Front Street, Oak Bluffs, MA 02557
MLS# 73576389Listed by: Wallace & Co. Sotheby's International Realty
New
$850,000Active
0.25 Acres
15 Roger's Way, Oak Bluffs, MA 02557
MLS# 22604582Listed by: ISLAND REAL ESTATE
New
$4,395,000Active
3 beds 6 baths4,046 sq. ft.
267 Barnes Road, Oak Bluffs, MA 02557
MLS# 73572956Listed by: Donnelly + Co.
$260,000Active
1 beds 1 baths319 sq. ft.
33 Island Inn Road #UNIT 25 F, Oak Bluffs, MA 02557
MLS# 22604259Listed by: OCEAN PARK REALTY, INC.
$389,000Active
1 beds 2 baths590 sq. ft.
21 Island Inn Road #UNIT 38 G, Oak Bluffs, MA 02557
MLS# 22604260Listed by: OCEAN PARK REALTY, INC.
$310,000Active
1 beds 1 baths783 sq. ft.
27 Island Inn Road #UNIT 10C, Oak Bluffs, MA 02557
MLS# 22604263Listed by: OCEAN PARK REALTY, INC.
$287,500Active
1 beds 1 baths388 sq. ft.
27 Island Inn Road #UNIT 9C, Oak Bluffs, MA 02557
MLS# 22604264Listed by: OCEAN PARK REALTY, INC.
$789,000Active
0.39 Acres
24 Towanticut St, Oak Bluffs, MA 02568
MLS# 73568028Listed by: Alisan Lohan - Conway Properties
$2,678,000Active
4 beds 4 baths2,363 sq. ft.
31 Temahigan Avenue, Oak Bluffs, MA 02557
MLS# 22604054Listed by: PORTFOLIO PROPERTIES
$2,995,000Active
5 beds 2 baths1,731 sq. ft.
27 Beach Road, Oak Bluffs, MA 02557
MLS# 22604007Listed by: WALLACE & CO. SOTHEBY'S INTERNATIONAL REALTY
$1,095,000Active
3 beds 2 baths2,173 sq. ft.
2 Winemack Street, Oak Bluffs, MA 02557
MLS# 22603994Listed by: OCEAN PARK REALTY, INC.
$1,255,000Active
3 beds 2 baths912 sq. ft.
11 Stanley Street, Oak Bluffs, MA 02557
MLS# 22603967Listed by: ANCHOR REALTY OF MV
$1,296,000Pending
3 beds 2 baths908 sq. ft.
66 Hudson Avenue, Oak Bluffs, MA 02557
MLS# 22603955Listed by: ISLAND REAL ESTATE
$1,225,000Active
1 beds 2 baths1,428 sq. ft.
323 County Road, Oak Bluffs, MA 02557
MLS# 22603763Listed by: ANCHOR REALTY OF MV
$425,000Active
0.18 Acres
0 Heather Ln, Oak Bluffs, MA 02557
MLS# 73560451Listed by: Compass
$5,495,000Active
3 beds 3 baths2,234 sq. ft.
43 Sengekontacket Road, Oak Bluffs, MA 02557
MLS# 22603599Listed by: STUDIO REALTY LLC
$2,650,000Active
4 beds 3 baths1,858 sq. ft.
59 Tuckernuck Ave, Oak Bluffs, MA 02557
MLS# 73553801Listed by: Compass
$1,299,000Active
5 beds 2 baths1,968 sq. ft.
41 Edgartown Road, Vineyard Haven, MA 02568
MLS# 22603531Listed by: STUDIO REALTY LLC
$839,000Active
1 beds 1 baths804 sq. ft.
26 Winthrop Ave, Oak Bluffs, MA 02557
MLS# 73548644Listed by: Alisan Lohan - Conway Properties
$975,000Active
1.07 Acres
68 Pond View Drive, Oak Bluffs, MA 02557
MLS# 73548450Listed by: Sandpiper Realty, Inc.
$1,595,000Active
3 beds 4 baths2,739 sq. ft.
40 Hidden Cove Road #UNIT 2, Oak Bluffs, MA 02557
MLS# 22603277Listed by: WALLACE & CO. SOTHEBY'S INTERNATIONAL REALTY
$1,745,000Active
2 beds 1 baths561 sq. ft.
11 Beach Road, Oak Bluffs, MA 02557
MLS# 22603245Listed by: ANCHOR REALTY OF MV
$785,000Active
2 beds 1 baths624 sq. ft.
60R Carol Lane, Oak Bluffs, MA 02557
MLS# 22603182Listed by: ISLAND REAL ESTATE
$1,875,000Active
3 beds 3 baths1,439 sq. ft.
33 Vineyard Avenue, Oak Bluffs, MA 02557
MLS# 22603165Listed by: DOUGLAS ELLIMAN OF MA, LLC
$3,400,000Active
3 beds 5 baths3,260 sq. ft.
27 Double Ox Rd, Oak Bluffs, MA 02557
MLS# 73542323Listed by: Sandpiper Realty, Inc.
$1,750,000Active
3 beds 4 baths2,376 sq. ft.
28 Grovedale Road, Oak Bluffs, MA 02568
MLS# 73540119Listed by: OwnerEntry.com
$1,750,000Pending
3 beds 4 baths2,376 sq. ft.
28 Grovedale Road, Oak Bluffs, MA 02557
MLS# 22603069Listed by: OWNERENTRY.COM
$2,999,000Active
3 beds 4 baths3,082 sq. ft.
53 Stoney Hill Rd, West Tisbury, MA 02575
MLS# 73539028Listed by: Compass
$549,000Active
0.07 Acres
112 Dukes County Avenue, Oak Bluffs, MA 02557
MLS# 22602745Listed by: WALLACE & CO. SOTHEBY'S INTERNATIONAL REALTY
$2,195,000Active
3 beds 2 baths1,425 sq. ft.
312 E Chop Drive, Vineyard Haven, MA 02568
MLS# 22602660Listed by: WALLACE & CO. SOTHEBY'S INTERNATIONAL REALTY
$1,100,000Active
3 beds 2 baths1,302 sq. ft.
47 Winemack Street, Oak Bluffs, MA 02557
MLS# 22602630Listed by: ANCHOR REALTY OF MV
$849,000Active
1 beds 1 baths797 sq. ft.
37 Circuit Avenue #UNIT 5, Oak Bluffs, MA 02557
MLS# 22602409Listed by: ANCHOR REALTY OF MV
$879,000Active
2 beds 1 baths990 sq. ft.
37 Circuit Avenue #UNIT 4, Oak Bluffs, MA 02557
MLS# 22602411Listed by: ANCHOR REALTY OF MV
$1,499,000Active
3 beds 3 baths1,645 sq. ft.
7 Ploughshare Lane, Oak Bluffs, MA 02557
MLS# 73527741Listed by: Sandpiper Realty, Inc.
$2,800,000Active
4 beds 5 baths3,927 sq. ft.
44 Tiffany Dr, Oak Bluffs, MA 02557
MLS# 73527128Listed by: MV Luxury Homes LLC
$1,295,000Active
3 beds 2 baths1,863 sq. ft.
3 Troy Street, Oak Bluffs, MA 02557
MLS# 22602560Listed by: WALLACE & CO. SOTHEBY'S INTERNATIONAL REALTY
$5,100,000Active
2.34 Acres
7 Overview Lane, Oak Bluffs, MA 02557
MLS# 22602561Listed by: WALLACE & CO. SOTHEBY'S INTERNATIONAL REALTY
$1,155,000Pending
3 beds 2 baths1,164 sq. ft.
3 Kims Way, Oak Bluffs, MA 02557
MLS# 22602448Listed by: WALLACE & CO. SOTHEBY'S INTERNATIONAL REALTY
$4,600,000Active
6 beds 6 baths3,998 sq. ft.
15 Tamarack Lane, Oak Bluffs, MA 02557
MLS# 73522816Listed by: Donnelly + Co.
$825,000Active
2 beds 1 baths985 sq. ft.
19 Perkins Avenue, Oak Bluffs, MA 02557
MLS# 73522647Listed by: Sandpiper Realty, Inc.
$809,000Active
0.39 Acres
7 Highland Avenue, Oak Bluffs, MA 02557
MLS# 22600713Listed by: EXP REALTY, LLC
$1,049,000Active
0.25 Acres
0 Temahigan Ave & Dover St, Oak Bluffs, MA 02557
MLS# 22602202Listed by: OCEAN PARK REALTY, INC.
$1,875,000Active
3 beds 3 baths1,431 sq. ft.
33 Vineyard Ave, Oak Bluffs, MA 02557
MLS# 73511961Listed by: Douglas Elliman Real Estate - Nantucket
$1,850,000Active
4 beds 2 baths1,833 sq. ft.
22 Old Harbor Lane, Oak Bluffs, MA 02557
MLS# 73505800Listed by: Sandpiper Realty, Inc.
$5,100,000Active
2.34 Acres
7 Overview Lane, Oak Bluffs, MA 02557
MLS# 73503350Listed by: Wallace & Co. Sotheby's International Realty
$549,000Active
0.07 Acres
112 Dukes County, Oak Bluffs, MA 02557
MLS# 73482521Listed by: Wallace & Co. Sotheby's International Realty
$5,225,000Active
6 beds 4 baths2,890 sq. ft.
4 Canonicus Ave, Oak Bluffs, MA 02557
MLS# 73472922Listed by: Sandpiper Realty, Inc.
$3,100,000Active
4 beds 3 baths1,728 sq. ft.
6 Brewster Ave, Oak Bluffs, MA 02557
MLS# 73472925Listed by: Sandpiper Realty, Inc.
$849,000Active
2 beds 1 baths953 sq. ft.
50 Canonicus Avenue, Oak Bluffs, MA 02557
MLS# 22505096Listed by: ISLAND REAL ESTATE

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©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.

Terms of use Accessibility DMCA notice Fraud alert Privacy policy Fair housing Do not sell info NY reasonable accommodation Submit agent or broker complaint

Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.

©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.