Oak Bluffs town, MA - homes for sale

43 of 43 results displayed

New
$5,995,000Active
3 beds 3 baths2,234 sq. ft.
43 Sengekontacket Road, Oak Bluffs, MA 02557
MLS# 22603599Listed by: STUDIO REALTY LLC
New
$2,650,000Active
4 beds 3 baths1,858 sq. ft.
59 Tuckernuck Ave, Oak Bluffs, MA 02557
MLS# 73553801Listed by: Compass
New
$1,399,000Active
5 beds 2 baths1,968 sq. ft.
41 Edgartown Road, Vineyard Haven, MA 02568
MLS# 22603531Listed by: STUDIO REALTY LLC
New
$3,675,000Active
4 beds 3 baths1,800 sq. ft.
28 Beach Rd, Oak Bluffs, MA 02557
MLS# 73552922Listed by: Compass
New
$1,075,000Active
3 beds 2 baths1,135 sq. ft.
21 Butler Avenue #1, Oak Bluffs, MA 02557
MLS# 73552744Listed by: Compass
$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.
$1,296,000Active
3 beds 2 baths1,144 sq. ft.
82 Pennsylvania Avenue, Oak Bluffs, MA 02557
MLS# 73545719Listed 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
$794,000Active
2 beds 1 baths624 sq. ft.
60R Carol Lane, Oak Bluffs, MA 02557
MLS# 22603182Listed by: ISLAND REAL ESTATE
Open Sat, 9:30 to 11:30am
$1,995,000Active
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
$1,750,000Active
3 beds 4 baths2,376 sq. ft.
28 Grovedale Road, Oak Bluffs, MA 02557
MLS# 22603069Listed by: OWNERENTRY.COM
$1,575,000Active
3 beds 3 baths1,621 sq. ft.
27 Laurel Avenue, Oak Bluffs, MA 02557
MLS# 73540741Listed by: Berkshire Hathaway HomeServices Robert Paul Properties
$3,099,000Active
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
$2,295,000Active
3 beds 2 baths1,425 sq. ft.
312 E Chop Drive, Vineyard Haven, MA 02568
MLS# 22602660Listed by: WALLACE & CO. SOTHEBY'S INTERNATIONAL REALTY
$1,199,000Active
3 beds 2 baths1,302 sq. ft.
47 Winemack Street, Oak Bluffs, MA 02557
MLS# 22602630Listed by: ANCHOR REALTY OF MV
$1,755,000Active
3 beds 3 baths2,695 sq. ft.
68 Front Street, Oak Bluffs, MA 02557
MLS# 22602650Listed by: OCEAN PARK REALTY, INC.
$2,295,000Active
3 beds 4 baths1,425 sq. ft.
312 East Chop Drive, Oak Bluffs, MA 02557
MLS# 73529130Listed by: Wallace & Co. Sotheby's International Realty
$869,000Active
1 beds 1 baths797 sq. ft.
37 Circuit Avenue #UNIT 5, Oak Bluffs, MA 02557
MLS# 22602409Listed by: ANCHOR REALTY OF MV
$899,000Active
2 beds 1 baths990 sq. ft.
37 Circuit Avenue #UNIT 4, Oak Bluffs, MA 02557
MLS# 22602411Listed by: ANCHOR REALTY OF MV
$1,599,000Active
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
$1,349,000Active
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
$1,155,000Active
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
$1,200,000Active
0.25 Acres
0 Temahigan Ave & Dover St, Oak Bluffs, MA 02557
MLS# 22602202Listed by: OCEAN PARK REALTY, INC.
Open Sat, 9:30 to 11:30am
$1,995,000Active
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
$1,495,000Active
4 beds 3 baths1,514 sq. ft.
26 Sea Glen Road, Oak Bluffs, MA 02557
MLS# 73500318Listed by: Compass
$5,450,000Active
4 beds 6 baths3,300 sq. ft.
8 Paddock Rd, Oak Bluffs, MA 02557
MLS# 73499730Listed by: Sandpiper Realty, Inc.
$5,295,000Active
3 beds 7 baths3,608 sq. ft.
385 Barnes Road, Oak Bluffs, MA 02557
MLS# 73496934Listed by: Donnelly + Co.
$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.
$3,250,000Active
4 beds 3 baths1,728 sq. ft.
6 Brewster Ave, Oak Bluffs, MA 02557
MLS# 73472925Listed by: Sandpiper Realty, Inc.
$899,000Active
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.