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Dukes County, MA - homes for sale
124 of 124 results displayed
- New
$1,075,000Active3 beds 2 baths948 sq. ft.21 Flamingo Drive, Edgartown, MA 02539
MLS# 73594824Listed by: Compass - New
$2,875,000Active4 beds 5 baths2,900 sq. ft.91 Litchfield Rd, Edgartown, MA 02539
MLS# 73594795Listed by: Sandpiper Realty, Inc. - New
$6,500,000Active6 beds 7 baths4,753 sq. ft.16 Red Coat Hill, West Tisbury, MA 02575
MLS# 73594019Listed by: Vineyard Dream Realty LLC - New
$5,750,000Active6 beds 7 baths5,424 sq. ft.41 Hagerty Drive, Tisbury, MA 02568
MLS# 73593991Listed by: Vineyard Dream Realty LLC - New
$1,950,000Active2 beds 2 baths1,459 sq. ft.25 Oak Avenue, Oak Bluffs, MA 02557
MLS# 73593599Listed by: Sandpiper Realty, Inc. - New
$3,950,000Active5 beds 5 baths4,125 sq. ft.6 Hollow Way, Edgartown, MA 02539
MLS# 73592553Listed by: Donnelly + Co. 
$895,000Pending3 beds 2 baths1,092 sq. ft.31 Beacon Avenue, Oak Bluffs, MA 02557
MLS# 22605310Listed by: ISLAND REAL ESTATE
$3,295,000Active3 beds 3 baths2,701 sq. ft.26 Pulpit Ln, Edgartown, MA 02539
MLS# 73591230Listed by: Compass
$6,125,000Active4 beds 6 baths4,107 sq. ft.78 Plantingfield Way, Edgartown, MA 02568
MLS# 73590664Listed by: Sandpiper Realty, Inc.
$5,820,000Active4 beds 3 baths4,359 sq. ft.29 Llewellyn Way, Edgartown, MA 02539
MLS# 22605188Listed by: WALLACE & CO. SOTHEBY'S INTERNATIONAL REALTY
$3,790,000Active7 beds 5 baths4,464 sq. ft.31 Josiah Sachem Way, West Tisbury, MA 02575
MLS# 22605167Listed by: STUDIO REALTY LLC
$3,995,000Active4 beds 6 baths4,904 sq. ft.4 Garrett Way, Edgartown, MA 02539
MLS# 73588921Listed by: Sandpiper Realty, Inc.
$4,195,000Active5 beds 4 baths3,594 sq. ft.32 Marthas Road, Edgartown, MA 02539
MLS# 73586815Listed by: Compass
$3,200,000Active3 beds 4 baths2,370 sq. ft.16 Old Dunhams Corner Way, Edgartown, MA 02539
MLS# 73586583Listed by: Berkshire Hathaway HomeServices Commonwealth Real Estate
$6,900,000Active4 beds 5 baths2,961 sq. ft.8 Beach Plum Mdws, Edgartown, MA 02539
MLS# 73586485Listed by: Compass
$2,950,000Active8 beds 7 baths3,770 sq. ft.72 Chappaquiddick, Edgartown, MA 02539
MLS# 73586117Listed by: Sandpiper Realty, Inc.
$1,995,000Pending4 beds 3 baths1,918 sq. ft.25 Fulling Mill Road, Chilmark, MA 02535
MLS# 22605031Listed by: WALLACE & CO. SOTHEBY'S INTERNATIONAL REALTY
$1,875,000Pending4 beds 3 baths2,430 sq. ft.42 Bold Meadow Road, Edgartown, MA 02539
MLS# 22605017Listed by: WALLACE & CO. SOTHEBY'S INTERNATIONAL REALTY
$2,150,000Pending5 beds 4 baths161 sq. ft.15 Pequot Avenue, Oak Bluffs, MA 02557
MLS# 22604724Listed by: ANCHOR REALTY OF MV
$9,500,000Active8 beds 11 baths7,585 sq. ft.12 Boldwater Road, Edgartown, MA 02539
MLS# 73584420Listed by: Serhant
$2,995,000Active4 beds 5 baths2,348 sq. ft.24 Myober Ln, Edgartown, MA 02539
MLS# 73583186Listed by: Compass
$1,850,000Active4 beds 6 baths2,518 sq. ft.32 Norton Orchard Rd, Edgartown, MA 02539
MLS# 73582365Listed by: Keller Williams South Watuppa
$2,490,000Active3 beds 4 baths3,579 sq. ft.8 Jeffers Way, Aquinnah, MA 02535
MLS# 73581761Listed by: Compass
$4,995,000Active4 beds 5 baths3,348 sq. ft.98 Edgartown Bay Rd, Edgartown, MA 02539
MLS# 73581090Listed by: Compass
$1,375,000Active5 beds 2 baths1,952 sq. ft.234 County Road, Oak Bluffs, MA 02557
MLS# 73580264Listed by: Sandpiper Realty, Inc.
$3,400,000Active5 beds 5 baths3,095 sq. ft.62 Schoolhouse Rd, Edgartown, MA 02539
MLS# 73577862Listed by: Vineyard Village Realty
$2,455,000Active4 beds 5 baths3,039 sq. ft.99 The Boulevard, Edgartown, MA 02539
MLS# 73577541Listed by: Compass- Open Sat, 10am to 12pm
$1,595,000Active4 beds 3 baths1,898 sq. ft.20 Hidden Cove, Oak Bluffs, MA 02557
MLS# 73577547Listed by: Compass 
$2,200,000Active3 beds 3 baths2,420 sq. ft.61 Canonicus Ave, Oak Bluffs, MA 02557
MLS# 73576858Listed by: Donnelly + Co.
$1,755,000Active3 beds 3 baths2,815 sq. ft.68 Front Street, Oak Bluffs, MA 02557
MLS# 22604610Listed by: WALLACE & CO. SOTHEBY'S INTERNATIONAL REALTY
$1,150,000Pending4 beds 3 baths1,924 sq. ft.7 Fawndale Road, Vineyard Haven, MA 02568
MLS# 22604597Listed by: ISLAND REAL ESTATE
$2,295,000Active4 beds 4 baths3,056 sq. ft.125 Mayflower Ln, Tisbury, MA 02568
MLS# 73575143Listed by: Sandpiper Realty, Inc.
$1,649,900Active3 beds 2 baths1,540 sq. ft.43 N Slope Lane, Chilmark, MA 02535
MLS# 73573563Listed by: NorthStar Real Estate, LLC
$1,649,000Active3 beds 2 baths1,540 sq. ft.43 N Slope Lane, Chilmark, MA 02535
MLS# 22604496Listed by: NORTH STAR REAL ESTATE, LLC
$4,395,000Active3 beds 6 baths4,046 sq. ft.267 Barnes Road, Oak Bluffs, MA 02557
MLS# 73572956Listed by: Donnelly + Co.
$2,500,000Active3 beds 3 baths2,876 sq. ft.10 Woodhaven Drive, Edgartown, MA 02539
MLS# 22604449Listed by: PORTFOLIO PROPERTIES
$2,095,000Active4 beds 4 baths2,876 sq. ft.18 Sylvan Avenue, Vineyard Haven, MA 02568
MLS# 22604386Listed by: WALLACE & CO. SOTHEBY'S INTERNATIONAL REALTY- Open Sun, 10am to 12pm
$905,000Active3 beds 2 baths2,208 sq. ft.74 Chase Lane & 25 Norton Ave, Vineyard Haven, MA 02568
MLS# 22604285Listed by: PORTFOLIO PROPERTIES 
$3,075,000Active3 beds 2 baths1,962 sq. ft.21 Vickers Street, Edgartown, MA 02539
MLS# 73567342Listed by: Donnelly + Co.
$2,250,000Active4 beds 3 baths1,938 sq. ft.88 Franklin Street, Vineyard Haven, MA 02568
MLS# 22604150Listed by: ISLAND REAL ESTATE
$2,500,000Active4 beds 3 baths1,786 sq. ft.9 Codman Spring Road, Edgartown, MA 02539
MLS# 22604104Listed by: WALLACE & CO. SOTHEBY'S INTERNATIONAL REALTY
$2,478,000Active4 beds 4 baths2,363 sq. ft.31 Temahigan Avenue, Oak Bluffs, MA 02557
MLS# 22604054Listed by: PORTFOLIO PROPERTIES
$6,150,000Active6 beds 7 baths5,034 sq. ft.59 Hagerty Drive, Tisbury, MA 02568
MLS# 73565263Listed by: Donnelly + Co.
$2,850,000Active6 beds 2 baths1,957 sq. ft.49 The Boulevard, Edgartown, MA 02539
MLS# 22604053Listed by: PORTFOLIO PROPERTIES
$2,200,000Pending2 beds 2 baths2,631 sq. ft.99 Oak Lane, West Tisbury, MA 02575
MLS# 22604013Listed by: WALLACE & CO. SOTHEBY'S INTERNATIONAL REALTY
$1,229,000Active2 beds 2 baths1,996 sq. ft.29 Scotchmans Lane, West Tisbury, MA 02575
MLS# 22604010Listed by: ISLAND REAL ESTATE
$2,995,000Active5 beds 2 baths1,731 sq. ft.27 Beach Road, Oak Bluffs, MA 02557
MLS# 22604007Listed by: WALLACE & CO. SOTHEBY'S INTERNATIONAL REALTY
$2,995,000Active3 beds 1 baths973 sq. ft.36 Hines Point Rd, Tisbury, MA 02568
MLS# 73564072Listed by: Donnelly + Co.
$1,095,000Pending3 beds 2 baths2,173 sq. ft.2 Winemack Street, Oak Bluffs, MA 02557
MLS# 22603994Listed by: OCEAN PARK REALTY, INC.
$1,195,000Active3 beds 2 baths912 sq. ft.11 Stanley Street, Oak Bluffs, MA 02557
MLS# 22603967Listed by: ANCHOR REALTY OF MV
$10,750,000Active7 beds 4 baths4,855 sq. ft.139 Chappaquiddick Road, Edgartown, MA 02539
MLS# 73563263Listed by: Sandpiper Realty, Inc.
$1,395,000Active4 beds 4 baths2,670 sq. ft.528 Main Street, Tisbury, MA 02568
MLS# 73563290Listed by: Wallace & Co. Sotheby's International Realty- Open Sun, 12 to 1:30pm
$1,095,000Active1 beds 2 baths1,428 sq. ft.323 County Road, Oak Bluffs, MA 02557
MLS# 22603763Listed by: ANCHOR REALTY OF MV 
$1,495,000Active4 beds 3 baths2,334 sq. ft.150 Field View Lane, West Tisbury, MA 02575
MLS# 22603890Listed by: ISLAND REAL ESTATE
$1,695,000Pending3 beds 3 baths3,702 sq. ft.174 Middle Road, Chilmark, MA 02535
MLS# 22603889Listed by: ISLAND REAL ESTATE
$16,250,000Active6 beds 8 baths8,648 sq. ft.25 Brickyard Road, Chilmark, MA 02535
MLS# 22603861Listed by: STUDIO REALTY LLC
$1,895,000Active5 beds 3 baths3,480 sq. ft.135 Mayflower Lane, Tisbury, MA 02568
MLS# 73560676Listed by: Donnelly + Co.
$2,695,000Active5 beds 4 baths2,374 sq. ft.124 Main St., Tisbury, MA 02568
MLS# 73560291Listed by: Wallace & Co. Sotheby's International Realty
$1,500,000Active3 beds 2 baths1,717 sq. ft.8 Pip'n Circle, Edgartown, MA 02539
MLS# 73559452Listed by: Sandpiper Realty, Inc.
$1,995,000Active4 beds 3 baths1,918 sq. ft.21 & 25 Fulling Mill Road, Chilmark, MA 02535
MLS# 73555055Listed by: Wallace & Co. Sotheby's International Realty
$5,495,000Active3 beds 3 baths2,234 sq. ft.43 Sengekontacket Road, Oak Bluffs, MA 02557
MLS# 22603599Listed by: STUDIO REALTY LLC
$3,200,000Active4 beds 6 baths3,428 sq. ft.19 Llewellyn Way, Edgartown, MA 02539
MLS# 73554803Listed by: Sandpiper Realty, Inc.
$3,295,000Active5 beds 4 baths2,330 sq. ft.29 & 33 Lagoon Pond Road, Vineyard Haven, MA 02568
MLS# 22603560Listed by: WALLACE & CO. SOTHEBY'S INTERNATIONAL REALTY
$2,595,000Active4 beds 3 baths1,858 sq. ft.59 Tuckernuck Ave, Oak Bluffs, MA 02557
MLS# 73553801Listed by: Compass
$3,495,000Active5 beds 5 baths4,816 sq. ft.30 Water Gate Road, Vineyard Haven, MA 02568
MLS# 22603552Listed by: STUDIO REALTY LLC
$7,695,000Active4 beds 5 baths7,766 sq. ft.2 Lexington Avenue, Edgartown, MA 02539
MLS# 22603541Listed by: STUDIO REALTY LLC
$1,450,000Active4 beds 3 baths1,270 sq. ft.21 W Spring St, Tisbury, MA 02568
MLS# 73551628Listed by: Sandpiper Realty, Inc.
$2,950,000Pending3 beds 3 baths1,469 sq. ft.28 Black Point Road, Chilmark, MA 02535
MLS# 22603395Listed by: ISLAND REAL ESTATE
$1,395,000Active3 beds 2 baths1,588 sq. ft.44 Prices Way, Edgartown, MA 02539
MLS# 73549401Listed by: Compass
$1,600,000Active3 beds 3 baths2,155 sq. ft.132 South Rd, Chilmark, MA 02535
MLS# 73546774Listed by: Compass
$3,795,000Active3 beds 4 baths3,426 sq. ft.96 Hammett Ln, Chilmark, MA 02535
MLS# 73545525Listed by: Karen M. Overtoom R.E.
$3,495,000Active4 beds 4 baths3,200 sq. ft.64 Christiantown, West Tisbury, MA 02575
MLS# 73544561Listed by: Karen M. Overtoom R.E.
$1,745,000Active2 beds 1 baths561 sq. ft.11 Beach Road, Oak Bluffs, MA 02557
MLS# 22603245Listed by: ANCHOR REALTY OF MV
$785,000Active2 beds 1 baths624 sq. ft.60R Carol Lane, Oak Bluffs, MA 02557
MLS# 22603182Listed by: ISLAND REAL ESTATE
$3,400,000Active3 beds 5 baths3,260 sq. ft.27 Double Ox Rd, Oak Bluffs, MA 02557
MLS# 73542323Listed by: Sandpiper Realty, Inc.
$2,999,000Active3 beds 4 baths3,082 sq. ft.53 Stoney Hill Rd, West Tisbury, MA 02575
MLS# 73539028Listed by: Compass
$15,400,000Active6 beds 9 baths6,967 sq. ft.8 Snail Road, Chilmark, MA 02535
MLS# 22602961Listed by: CORCORAN PROPERTY ADVISORS
$1,570,000Active3 beds 3 baths2,347 sq. ft.41 & 0 Cook Road, Tisbury, MA 02568
MLS# 73536989Listed by: Compass
$5,200,000Active5 beds 4 baths4,044 sq. ft.49 Gosnolds Way, Chilmark, MA 02535
MLS# 73534187Listed by: Wallace & Co. Sotheby's International Realty
$1,775,000Active4 beds 3 baths2,064 sq. ft.99 Old Purchase Road, Edgartown, MA 02539
MLS# 73531632Listed by: Donnelly + Co.
$4,995,000Active3 beds 2 baths2,710 sq. ft.35 South Bowl Rd, Chilmark, MA 02535
MLS# 73531359Listed by: Donnelly + Co.
$1,100,000Active3 beds 2 baths1,302 sq. ft.47 Winemack Street, Oak Bluffs, MA 02557
MLS# 22602630Listed by: ANCHOR REALTY OF MV
$49,000,000Pending12 beds 14 baths8,994 sq. ft.15 Forever Wild Way, Edgartown, MA 02539
MLS# 22602611Listed by: CORCORAN PROPERTY ADVISORS
$1,399,000Active3 beds 3 baths1,645 sq. ft.7 Ploughshare Lane, Oak Bluffs, MA 02557
MLS# 73527741Listed by: Sandpiper Realty, Inc.
$2,595,000Active4 beds 5 baths3,927 sq. ft.44 Tiffany Dr, Oak Bluffs, MA 02557
MLS# 73527128Listed by: MV Luxury Homes LLC
$1,295,000Pending3 beds 2 baths1,863 sq. ft.3 Troy Street, Oak Bluffs, MA 02557
MLS# 22602560Listed by: WALLACE & CO. SOTHEBY'S INTERNATIONAL REALTY
$5,900,000Active7 beds 5 baths6,921 sq. ft.19 Locust Ln, Aquinnah, MA 02535
MLS# 73526631Listed by: eXp Realty LLC - Corporate Office
$5,800,000Active6 beds 9 baths5,732 sq. ft.31 Lambert's Cove Rd., Tisbury, MA 02568
MLS# 73525014Listed by: Wallace & Co. Sotheby's International Realty
$3,425,000Active5 beds 3 baths2,701 sq. ft.20 James Pond Way, West Tisbury, MA 02575
MLS# 22602483Listed by: ISLAND REAL ESTATE
$1,095,000Active3 beds 1 baths998 sq. ft.299 Daggett Ave #A, Tisbury, MA 02568
MLS# 73524099Listed by: Karen M. Overtoom R.E.
$45,000,000Active7 beds 13 baths11,200 sq. ft.18 Point Inner Way, Chilmark, MA 02535
MLS# 73523462Listed by: Wallace & Co. Sotheby's International Realty
$2,590,000Active4 beds 8 baths4,530 sq. ft.15 Twenty First St N, Edgartown, MA 02539
MLS# 73523165Listed by: Compass
$4,600,000Active6 beds 6 baths3,998 sq. ft.15 Tamarack Lane, Oak Bluffs, MA 02557
MLS# 73522816Listed by: Donnelly + Co.
$799,000Active2 beds 1 baths985 sq. ft.19 Perkins Avenue, Oak Bluffs, MA 02557
MLS# 73522647Listed by: Sandpiper Realty, Inc.
$2,950,000Active4 beds 3 baths2,208 sq. ft.13 Young Street, Edgartown, MA 02539
MLS# 73522670Listed by: Donnelly + Co.
$1,200,000Active4 beds 4 baths2,304 sq. ft.33 Alyssa Lane, Vineyard Haven, MA 02568
MLS# 22602337Listed by: PORTFOLIO PROPERTIES
$6,995,000Active4 beds 3 baths2,624 sq. ft.103 Edgartown Bay Road, Edgartown, MA 02539
MLS# 73520913Listed by: Wallace & Co. Sotheby's International Realty
$2,195,000Active5 beds 4 baths2,628 sq. ft.7 Pip'n Circle, Edgartown, MA 02539
MLS# 73520213Listed by: Sandpiper Realty, Inc.
$2,195,000Active3 beds 2 baths2,510 sq. ft.26 Bijahs Way, Chilmark, MA 02535
MLS# 73520138Listed by: Karen M. Overtoom R.E.
$1,250,000Active4 beds 3 baths1,738 sq. ft.22 Oklahoma Avenue, Vineyard Haven, MA 02568
MLS# 22602241Listed by: WALLACE & CO. SOTHEBY'S INTERNATIONAL REALTY
$21,500,000Active10 beds 14 baths7,598 sq. ft.56 North Summer Street, Edgartown, MA 02539
MLS# 73517157Listed by: Wallace & Co. Sotheby's International Realty
$4,600,000Active4 beds 4 baths3,715 sq. ft.9 Marthas Way, Edgartown, MA 02539
MLS# 73514104Listed by: Vineyard Village Realty
$1,800,000Pending4 beds 2 baths2,518 sq. ft.32 Norton Orchard Road, Edgartown, MA 02539
MLS# 22601986Listed by: PORTFOLIO PROPERTIES
$1,695,000Active3 beds 3 baths1,431 sq. ft.33 Vineyard Ave, Oak Bluffs, MA 02557
MLS# 73511961Listed by: Douglas Elliman Real Estate - Nantucket
$2,195,000Active5 beds 4 baths3,328 sq. ft.159 Lake Street, Tisbury, MA 02568
MLS# 73511187Listed by: Wallace & Co. Sotheby's International Realty
$2,300,000Active3 beds 3 baths1,344 sq. ft.60 Crocker Drive, Edgartown, MA 02539
MLS# 22601571Listed by: ISLAND REAL ESTATE
$2,850,000Active4 beds 3 baths2,927 sq. ft.2 Bold Meadow Road, Edgartown, MA 02539
MLS# 73494371Listed by: Donnelly + Co.
$2,125,000Active3 beds 3 baths2,630 sq. ft.81 Whalers Walk, Edgartown, MA 02539
MLS# 73493917Listed by: Sandpiper Realty, Inc.
$1,395,000Active3 beds 1 baths1,066 sq. ft.17 Chapman La, Edgartown, MA 02539
MLS# 73490019Listed by: Compass
$2,495,000Active1 beds 2 baths1,236 sq. ft.218 Upper Main Street, Edgartown, MA 02539
MLS# 73540958Listed by: Wallace & Co. Sotheby's International Realty
$16,900,000Active8 beds 8 baths6,041 sq. ft.114 North Water Street, Edgartown, MA 02539
MLS# 73485121Listed by: Donnelly + Co.
$3,995,000Active8 beds 6 baths4,651 sq. ft.23 Beetle Swamp Road, Edgartown, MA 02539
MLS# 73483686Listed by: Sandpiper Realty, Inc.
$4,695,000Active3 beds 2 baths1,716 sq. ft.16 Frog Hollow, Tisbury, MA 02557
MLS# 73478787Listed by: Wallace & Co. Sotheby's International Realty
$3,100,000Active1 beds 1 baths1,250 sq. ft.114 Meetinghouse Way, Edgartown, MA 02539
MLS# 73478796Listed by: Wallace & Co. Sotheby's International Realty
$5,225,000Active6 beds 4 baths2,890 sq. ft.4 Canonicus Ave, Oak Bluffs, MA 02557
MLS# 73472922Listed by: Sandpiper Realty, Inc.
$3,100,000Active4 beds 3 baths1,728 sq. ft.6 Brewster Ave, Oak Bluffs, MA 02557
MLS# 73472925Listed by: Sandpiper Realty, Inc.
$2,299,000Active4 beds 3 baths1,910 sq. ft.76 Washque Ave, Edgartown, MA 02539
MLS# 73472929Listed by: Sandpiper Realty, Inc.
$2,700,000Active4 beds 5 baths2,750 sq. ft.6 Laura's Way, Edgartown, MA 02539
MLS# 73471802Listed by: Vineyard Village Realty
$1,125,000Active2 beds 1 baths896 sq. ft.45 Quenames Rd, Chilmark, MA 02535
MLS# 73471152Listed by: Sandpiper Realty, Inc.
$1,150,000Active2 beds 1 baths924 sq. ft.47 Quenames Rd, Chilmark, MA 02535
MLS# 73471155Listed by: Sandpiper Realty, Inc.
$1,325,000Active4 beds 3 baths1,714 sq. ft.116 Franklin Terrace, Tisbury, MA 02568
MLS# 22600011Listed by: KELLER WILLIAMS REALTY
$3,050,000Active3 beds 3 baths2,686 sq. ft.4 Noman's Watch Road, Aquinnah, MA 02535
MLS# 73457922Listed by: Compass
$2,595,000Active5 beds 2 baths2,386 sq. ft.187 Lagoon Pond Road, Tisbury, MA 02575
MLS# 73441105Listed by: Compass
$1,298,000Active3 beds 2 baths1,429 sq. ft.10 Elm St, Tisbury, MA 02568
MLS# 73154137Listed by: Bold Real Estate Inc.
Local realty services provided by:CENTURY 21 Signature Properties, CENTURY 21 Custom Home Realty
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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.
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.