366

Dukes County MA Homes for Sale

Section Image
  • 110 5th St N, Edgartown, MA 02539
    110 5th St N, Edgartown, MA 02539
    110 5th St N, Edgartown, MA 02539
    /40

    $3,400,000

    • 4 Beds
    • 3.5 Baths
    • 4,372 Sq Ft

    110 5th St N, Edgartown, MA 02539

    Water views with a pool! This chic contemporary 4-bedroom home with a pool and 2-car garage enjoys the ever-changing water views of Sengekontacket Pond and Nantucket Sound on three levels. Fully renovated, this delightful home, being sold turnkey, marries a timeless Vineyard vibe with modern luxury. The mudroom entryway opens to the kitchen with a breakfast island, dining room, and living room

    Stephanie Roache Donnelly + Co.

    110 5th St N, Edgartown, MA 02539
  • 25 Fulling Mill Rd, Chilmark, MA 02535
    25 Fulling Mill Rd, Chilmark, MA 02535
    25 Fulling Mill Rd, Chilmark, MA 02535
    /31

    $2,450,000

    • 4 Beds
    • 3 Baths
    • 1,918 Sq Ft

    25 Fulling Mill Rd, Chilmark, MA 02535

    Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to

    Thomas Wallace Wallace & Co. Sotheby's International Realty

    25 Fulling Mill Rd, Chilmark, MA 02535
  • 209 Cove Rd, Vineyard Haven, MA 02568
    209 Cove Rd, Vineyard Haven, MA 02568
    209 Cove Rd, Vineyard Haven, MA 02568
    /81

    $1,785,000

    • 4 Beds
    • 4 Baths
    • 2,194 Sq Ft

    209 Cove Rd, Vineyard Haven, MA 02568

    Wonderful Tashmoo Wood Association - West Chop. Welcome to this spacious and inviting home in the wonderful Tashmoo Wood Community. Rarely does a Single Family Home come on the market in this Private Association. This four (4) bedroom home, nestled on a private 1 acre lot with a tree lined driveway, abuts common land, is adjacent to Mink Meadows Golf Course and offers the ultimate in the

    Alisan Lohan-Conway Alisan Lohan-Conway Properties

    209 Cove Rd, Vineyard Haven, MA 02568
  • 32 Fourteenth St S, Edgartown, MA 02539
    32 Fourteenth St S, Edgartown, MA 02539
    32 Fourteenth St S, Edgartown, MA 02539
    /4

    $550,000

    • Land
    • 0.33 Acre
    • $1,666,667 per Acre

    32 Fourteenth St S, Edgartown, MA 02539

    This is a fabulous opportunity to build your vineyard home. Only minutes to Edgartown Village shops, restaurants, and the Edgartown ferry. With a short 6 minute drive to Edgartown Beach for great summer fun! This lot is close to Vineyard Golf Club, as well as Edgartown Golf Club. Lot will accommodate a 2-3 bedroom home. Buyer of this lot will need to have it engineered, and seller has engaged a

    Rebecca Putnam Putnam Realty

    32 Fourteenth St S, Edgartown, MA 02539
  • 147 Red Buoy Ln Unit 2.1, Tisbury, MA 02568
    147 Red Buoy Ln Unit 2.1, Tisbury, MA 02568
    147 Red Buoy Ln Unit 2.1, Tisbury, MA 02568
    /11

    $665,000

    • Land
    • 0.60 Acre
    • $1,108,333 per Acre

    147 Red Buoy Ln Unit 2.1, Tisbury, MA 02568

    Embrace the Essence of Martha's Vineyard on Red Buoy Lane. This idyllic vacant lot in Vineyard Haven offers a gateway to serene island living. Once you build your dream home, you will able to explore nature just steps away. Nearby there are two Lagoon access points for kayaking and swimming, as well as walking trails within the Martha's Vineyard Land Bank and Sheriff's Meadow properties. Enjoy

    Idalyn Macchia Gilstad Wallace & Co. Sotheby's

    147 Red Buoy Ln Unit 2.1, Tisbury, MA 02568
  • 00 Tashmoo Avenue @ Baylis Woods Unit 19.3, Vineyard Haven, MA 02568
    00 Tashmoo Avenue @ Baylis Woods Unit 19.3, Vineyard Haven, MA 02568
    00 Tashmoo Avenue @ Baylis Woods Unit 19.3, Vineyard Haven, MA 02568
    /17

    $520,000

    • Land
    • 0.33 Acre
    • $1,575,758 per Acre

    00 Tashmoo Avenue @ Baylis Woods Unit 19.3, Vineyard Haven, MA 02568

    Recent Price Reduction and Incredible opportunity build your dream home on Martha's Vineyard! Surrounded by large upscale homes on a paved road just minutes to Downtown. This perfectly shaped building lot in Baylis Woods in Vineyard Haven offers 14,374SF ready to build up to a six bedroom home. NOT in the 'watershed' no need for an enhanced Septic System. Have in hand designed preliminary septic

    Janna O'Loughlin Portfolio Real Estate, Inc.

    00 Tashmoo Avenue @ Baylis Woods Unit 19.3, Vineyard Haven, MA 02568
  • 00 Tashmoo Ave, Tisbury, MA 02568
    00 Tashmoo Ave, Tisbury, MA 02568
    00 Tashmoo Ave, Tisbury, MA 02568
    /15

    $520,000

    • Land
    • 0.33 Acre
    • $1,575,758 per Acre

    00 Tashmoo Ave, Tisbury, MA 02568

    Incredible opportunity build your dream home on Martha's Vineyard! Surrounded by large upscale homes on a paved road just minutes to Downtown. This perfectly shaped building lot in coveted Baylis Woods Subdivision in Vineyard Haven offers 14,374SF ready to build a six bedroom home. NOT in the 'watershed' so no need for an enhanced Septic System saving you money. Have a designed preliminary septic

    Janna O'Loughlin Portfolio Properties

    00 Tashmoo Ave, Tisbury, MA 02568
  • 0 Red Buoy Ln Unit Lot 147 32500084, Tisbury, MA 02568
    0 Red Buoy Ln Unit Lot 147 32500084, Tisbury, MA 02568
    0 Red Buoy Ln Unit Lot 147 32500084, Tisbury, MA 02568
    /10

    $665,000

    • Land
    • 0.61 Acre
    • $1,090,164 per Acre

    0 Red Buoy Ln Unit Lot 147 32500084, Tisbury, MA 02568

    Embrace the Essence of Martha's Vineyard on Red Buoy Lane. This idyllic vacant lot in Vineyard Haven offers a gateway to serene island living. Once you build your dream home, you will able to explore nature just steps away. Nearby there are two Lagoon access points for kayaking and swimming, as well as walking trails within the Martha's Vineyard Land Bank and Sheriff's Meadow properties. Enjoy

    Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty

    0 Red Buoy Ln Unit Lot 147 32500084, Tisbury, MA 02568
  • 261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
    261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
    261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
    /37

    $1,295,000

    • 3 Beds
    • 3 Baths
    • 1,628 Sq Ft

    261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568

    Welcome to this meticulously maintained 2+ bedroom, 3 bathroom end unit condo in Tashmoo Woods, built in 1998. The updated kitchen with granite countertops and high-end appliances opens to a dining room with a private deck overlooking lush woods. The first floor includes a den and a renovated bathroom. Upstairs, both bedrooms have ensuite bathrooms. Upgrades include propane heat, central air, a

    Jennifer O'hanlon Compass

    261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
  • 267 Barnes Rd, Oak Bluffs, MA 02557
    267 Barnes Rd, Oak Bluffs, MA 02557
    267 Barnes Rd, Oak Bluffs, MA 02557
    /40

    $4,500,000 Open Sun 1:30PM - 3:30PM

    • 3 Beds
    • 5.5 Baths
    • 4,046 Sq Ft

    267 Barnes Rd, Oak Bluffs, MA 02557

    Enjoy waterfront living at its best with 163’ of Lagoon frontage including a private sandy beach. Sited on 1.25 acres of lush-landscaped greenery, this incredible property with a sweeping lawn offers stunning water views and spectacular sunsets. This is your time to enjoy Vineyard life on the water...boating, swimming, kayaking, clamming, and more. Perfect for entertaining and comfortable living,

    Stephanie Roache Donnelly + Co.

    267 Barnes Rd, Oak Bluffs, MA 02557
  • 56 Robinson Rd, Edgartown, MA 02539
    56 Robinson Rd, Edgartown, MA 02539
    56 Robinson Rd, Edgartown, MA 02539
    /23

    $4,850,000

    • 4 Beds
    • 3.5 Baths
    • 3,500 Sq Ft

    56 Robinson Rd, Edgartown, MA 02539

    NEWER CONSTRUCTION, with POOL, 1/2 mile from the heart of EDGARTOWN VILLAGE! LOCATION, LOCATION! Approx. 3,500 square feet of open living space. The Great Room has a dramatic Two Story wall of windows which surround a gas fireplace and overlooks a 14 x 30 foot in ground, heated, saltwater pool which is surrounded by bluestone hardscape. In addition to the dramatic Great Room there is a first

    Michele Casavant Vineyard Village Realty

    56 Robinson Rd, Edgartown, MA 02539
  • 11 Norton St, Edgartown, MA 02539
    11 Norton St, Edgartown, MA 02539
    11 Norton St, Edgartown, MA 02539
    /12

    $2,349,000

    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft

    11 Norton St, Edgartown, MA 02539

    EDGARTOWN HISTORIC DISTRICT - Terrific opportunity for an INVESTOR, and HOMEOWNER alike, to have an in town House and Guest house in a wonderful part of Edgartown. Norton Street is such a lovely Street! Two cottages - One at the front and one at the rear of lot. Yard and parking for each cottage. Presently a three (3) bedroom lot but Town Sewer is available on Norton Street and once connected

    Alisan Lohan-Conway Alisan Lohan-Conway Properties

    11 Norton St, Edgartown, MA 02539
  • 60 Windsor Dr, Edgartown, MA 02539
    60 Windsor Dr, Edgartown, MA 02539
    60 Windsor Dr, Edgartown, MA 02539
    /23

    $1,650,000

    • 4 Beds
    • 2 Baths
    • 1,666 Sq Ft

    60 Windsor Dr, Edgartown, MA 02539

    Welcome to your ideal Edgartown retreat! This stunning classic cape-style home features four bedrooms and two baths. Built and cared for by a contractor, this residence exudes quality and attention to detail at every turn. Nestled on a picturesque half-acre lot in the Westminster Acres neighborhood, privacy abounds in this tranquil setting. Situated on a quiet paved dead-end street, enjoy easy

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    60 Windsor Dr, Edgartown, MA 02539
  • 145 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
    145 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
    145 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
    /29

    $1,485,000 Open Mon 11AM - 1PM

    • 4 Beds
    • 2 Baths
    • 1,436 Sq Ft

    145 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

    This coastal contemporary residence is located on a private 1.60-acre lot in West Tisbury, with convenient access to Long Point Wildlife Refuge and access to Lambert's Cove Beach~!The home features four bedrooms and two full bathrooms. On the first floor, you'll find two bright bedrooms, a modernized bathroom, and sliders from the living area that lead to a new AZEK deck and enclosed fenced

    Marilyn Moses Ocean Park Realty Inc

    145 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
  • 12 Boldwater Rd, Edgartown, MA 02539
    12 Boldwater Rd, Edgartown, MA 02539
    12 Boldwater Rd, Edgartown, MA 02539
    /47

    $9,995,000

    • 8 Beds
    • 12 Baths
    • 7,585 Sq Ft

    12 Boldwater Rd, Edgartown, MA 02539

    Uncover unparalleled Martha’s Vineyard opulence within a sprawling 9.8-acre estate. Immerse yourself in the timeless elegance and meticulous craftsmanship of the 7-bedroom | 10-bathroom main home, designed by the renowned architect, Robert A.M. Stern. From the grand foyer to the post & beam living room, each detail exudes sophistication. Revel in the warmth of multiple fireplaces and experience

    Jarrett Hurwitz Keller Williams Realty

    12 Boldwater Rd, Edgartown, MA 02539
  • 20 Edson Forest Rd, Vineyard Haven, MA 02568
    20 Edson Forest Rd, Vineyard Haven, MA 02568
    20 Edson Forest Rd, Vineyard Haven, MA 02568
    /94

    $4,395,000

    • 3 Beds
    • 5 Baths
    • 3,314 Sq Ft

    20 Edson Forest Rd, Vineyard Haven, MA 02568

    Exquisite home befitting its stunning location on four serene acres surrounded by conservation and agricultural lands and overlooking a neighbor's private pond. This special spot is authentic up-island character at its best. This three bedroom home (with six-bedroom septic system) was fully renovated down to the studs and finished in 2022, resulting in a truly beautiful luxury home with a

    Meg Bodnar Tea Lane Associates

    20 Edson Forest Rd, Vineyard Haven, MA 02568
  • 12 Boldwater Rd, Edgartown, MA 02539
    12 Boldwater Rd, Edgartown, MA 02539
    12 Boldwater Rd, Edgartown, MA 02539
    /26

    $9,995,000

    • 8 Beds
    • 11 Baths
    • 7,585 Sq Ft

    12 Boldwater Rd, Edgartown, MA 02539

    Uncover unparalleled Martha’s Vineyard opulence within a sprawling 9.8-acre estate. Immerse yourself in the timeless elegance and meticulous craftsmanship of the 7-bedroom | 10-bathroom main home, designed by the renowned architect, Robert A.M. Stern. From the grand foyer to the post & beam living room, each detail exudes sophistication. Revel in the warmth of multiple fireplaces and experience

    Michael Carucci Gibson Sotheby's International Realty

    12 Boldwater Rd, Edgartown, MA 02539
  • 35 Woody Bottom Rd, West Tisbury, MA 02575
    35 Woody Bottom Rd, West Tisbury, MA 02575
    35 Woody Bottom Rd, West Tisbury, MA 02575
    /32

    $2,495,000

    • 5 Beds
    • 3.5 Baths
    • 2,685 Sq Ft

    35 Woody Bottom Rd, West Tisbury, MA 02575

    This Cape style 5 bed/ 3.5 bath home is located in a nice area privately sited on 3 acres. This home features a nice floor plan thatincludes a fully equipped kitchen with center island, custom cabinetry and granite counters. Just off the kitchen is a sunny breakfastroom, a separate dining room, a spacious living room with fireplace and 2 sets of sliders to a backyard deck. There is a cozy

    Brenda Galligan Karen M. Overtoom R.E.

    35 Woody Bottom Rd, West Tisbury, MA 02575
  • 56 Holmes Hole Rd, Oak Bluffs, MA 02568
    56 Holmes Hole Rd, Oak Bluffs, MA 02568
    /2

    $699,000

    • Land
    • 0.49 Acre
    • $1,426,531 per Acre

    56 Holmes Hole Rd, Oak Bluffs, MA 02568

    Presenting a unique opportunity to acquire a wooded level lot located on Holmes Hole Road in Oak Bluffs, encompassing a .49-acre parcel situated within a Residential Urban (RU) zoning district. This property offers a serene environment ideal for constructing a home while remaining conveniently close to the town's amenities. There is potential for developing a 3-bedroom residence utilizing either

    Marilyn Moses Ocean Park Realty Inc

    56 Holmes Hole Rd, Oak Bluffs, MA 02568
  • 63 Bayes Hill Rd, Oak Bluffs, MA 02557
    63 Bayes Hill Rd, Oak Bluffs, MA 02557
    63 Bayes Hill Rd, Oak Bluffs, MA 02557
    /67

    $3,250,000

    • 4 Beds
    • 5 Baths
    • 5,165 Sq Ft

    63 Bayes Hill Rd, Oak Bluffs, MA 02557

    Tucked away in a serene setting, this beautifully designed custom home offers the ultimate in privacy, comfort, and luxury living. The first floor features a spacious open-concept design, seamlessly blending the dining room, kitchen, wet bar, and living area-perfect for entertaining or relaxing with the family. Home chefs will fall in love with the gourmet kitchen complete with custom cabinetry,

    Casandra Hyland Landmarks at TODAY Real Estate

    63 Bayes Hill Rd, Oak Bluffs, MA 02557
  • 11 Flamingo Dr, Edgartown, MA 02539
    11 Flamingo Dr, Edgartown, MA 02539
    11 Flamingo Dr, Edgartown, MA 02539
    /28

    $1,299,500

    • 4 Beds
    • 2 Baths
    • 1,820 Sq Ft

    11 Flamingo Dr, Edgartown, MA 02539

    Located in the Dodger's Hole subdivision is this inviting four bedrooms plus office, two-bathroom cape style home. The property has been well cared for and is a delight to view. Sited on .5 acres of land with a pea stone driveway, wraparound deck, and outdoor shower with new enclosure. The antique garage is a great storage space for lawn equipment, garden supplies or small vehicle. The living

    Skip Dostal, Jr Martha's Vineyard Real Estate

    11 Flamingo Dr, Edgartown, MA 02539
  • 32 Flamingo Dr, Edgartown, MA 02539
    32 Flamingo Dr, Edgartown, MA 02539
    32 Flamingo Dr, Edgartown, MA 02539
    /39

    $1,895,000

    • 5 Beds
    • 3 Baths
    • 2,432 Sq Ft

    32 Flamingo Dr, Edgartown, MA 02539

    This well-maintained country farmhouse is centrally located and is situated on just over one acre of land. A circular driveway welcomes you to the home with plenty of parking. There is a garden storage shed, irrigation system, playground, fire pit with outdoor seating, and wraparound covered porch. The rear entry door from the kitchen leads to the outdoor shower and spacious sunny deck. The first

    Skip Dostal, Jr Martha's Vineyard Real Estate

    32 Flamingo Dr, Edgartown, MA 02539
  • 10 Bridge Ln, Vineyard Haven, MA 02568
    10 Bridge Ln, Vineyard Haven, MA 02568
    10 Bridge Ln, Vineyard Haven, MA 02568
    /43

    $1,895,000

    • 3 Beds
    • 4 Baths
    • 2,512 Sq Ft

    10 Bridge Ln, Vineyard Haven, MA 02568

    This thoughtfully designed post and beam home blends craftsmanship with character, featuring artistic touches throughout that make it truly one-of-a-kind. The kitchen flows beautifully between the main living areas and an inviting dining space surrounded by windows offering access to one of several outdoor decks for effortless indoor-outdoor living. On the first floor, the primary suite includes

    Jill Napior Tea Lane Associates

    10 Bridge Ln, Vineyard Haven, MA 02568
  • 176 Middle Point Rd, Vineyard Haven, MA 02568
    176 Middle Point Rd, Vineyard Haven, MA 02568
    176 Middle Point Rd, Vineyard Haven, MA 02568
    /35

    $3,450,000

    • 5 Beds
    • 3 Baths
    • 2,713 Sq Ft

    176 Middle Point Rd, Vineyard Haven, MA 02568

    Rare private waterfront retreat on the Tisbury Great Pond. Nestled on an expansive 3.70 acres of land, this charming oasis offers a unique opportunity to enjoy serene water views and direct access to the beautiful Tisbury Great Pond and the South shore.The year-round main house spans 2,153 square feet and has three bedrooms and two bathrooms. Its seamless blend of Island charm and modern

    Tina Miller Compass

    176 Middle Point Rd, Vineyard Haven, MA 02568
  • 211 Edgartown Rd Unit 30, Vineyard Haven, MA 02568
    211 Edgartown Rd Unit 30, Vineyard Haven, MA 02568
    211 Edgartown Rd Unit 30, Vineyard Haven, MA 02568
    /4

    $425,000

    • Land
    • 1.00 Acre
    • $425,000 per Acre

    211 Edgartown Rd Unit 30, Vineyard Haven, MA 02568

    With Land Bank in your back yard, this well located and convenient property is part of a newly formed condominium sharing an acre with the neighboring home. The south facing hillside is a great place to build a home with a walk-out basement and up to 5 bedrooms. Room for a nice yard, gardens etc. The Septic has been installed already. Buyers will have to bring power and water in to site.

    Jim Feiner Feiner Real Estate

    211 Edgartown Rd Unit 30, Vineyard Haven, MA 02568
  • 211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568
    211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568
    211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568
    /15

    $1,065,000

    • 4 Beds
    • 2 Baths
    • 1,680 Sq Ft

    211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568

    A wonderful home on the outskirts of town. This property is being offered as part of a 2 unit condo. Set nicely back off the Edgartown Road, the existing home has 4/5 comfortable bedrooms and 2 baths on a nice shared 1-acre parcel with a good sense of privacy. Behind the home is a fire pit, a shed and another septic system already installed on the 2nd condo unit that will serve an additional 5

    Jim Feiner Feiner Real Estate

    211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568
  • 0 California Ave Unit 76 42933, Oak Bluffs, MA 02568
    0 California Ave Unit 76 42933, Oak Bluffs, MA 02568
    0 California Ave Unit 76 42933, Oak Bluffs, MA 02568
    /4

    $487,000

    • Land
    • 0.22 Acre
    • $2,213,636 per Acre

    0 California Ave Unit 76 42933, Oak Bluffs, MA 02568

    Nice level building lot ready for your ideas on how best to create your near town home on a quiet street. This is an established neighborhood and one of the last lots left to build on. Perc test has been done. This is in Zone 2 which allows 1 bedroom for this lot. Water and electric are nearby.

    Jim Joyce Carroll & Vincent R.E.

    0 California Ave Unit 76 42933, Oak Bluffs, MA 02568
  • 79 Circuit Ave, Oak Bluffs, MA 02557
    79 Circuit Ave, Oak Bluffs, MA 02557
    79 Circuit Ave, Oak Bluffs, MA 02557
    /64

    $2,250,000 Open Wed 10AM - 12PM

    • 4 Beds
    • 4 Baths
    • 3,076 Sq Ft

    79 Circuit Ave, Oak Bluffs, MA 02557

    Wonderful opportunity to reimagine this historic classic Victorian home located at the gateway to the Oak Bluffs Business district with a gorgeous, secluded garden and 5 off street parking spaces the property lends itself to a single-family home or conversion to a multi-family. The home has been both of these configurations in previous years. The current layout offers incredible opportunities

    kyle Neyer Tea Lane Associates

    79 Circuit Ave, Oak Bluffs, MA 02557
  • 28 Beach Rd, Oak Bluffs, MA 02557
    28 Beach Rd, Oak Bluffs, MA 02557
    28 Beach Rd, Oak Bluffs, MA 02557
    /20

    $3,750,000

    • 4 Beds
    • 3 Baths
    • 1,800 Sq Ft

    28 Beach Rd, Oak Bluffs, MA 02557

    Location, Location, location....This is rare opportunity to own a water front property with 240 degree views of the Harbor and Sound. The property is 5 minutes from either Ferry terminal and walking distance to East beach . The house is suitable for year round living , seasonal income and comfort through and through

    Scott Lewis Lewis Real Estate Services, LLC

    28 Beach Rd, Oak Bluffs, MA 02557
  • 85 Reservoir Rd, Vineyard Haven, MA 02568
    85 Reservoir Rd, Vineyard Haven, MA 02568
    85 Reservoir Rd, Vineyard Haven, MA 02568
    /44

    $8,995,000

    • 5 Beds
    • 7 Baths
    • 3,762 Sq Ft

    85 Reservoir Rd, Vineyard Haven, MA 02568

    Nestled within Seven Gates Farm, one of Martha's Vineyard's most storied and scenic communities, this 26.5-acre estate offers a beautifully renovated farmhouse that seamlessly blends modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    85 Reservoir Rd, Vineyard Haven, MA 02568
  • 37 Knoll Dr, Edgartown, MA 02539
    37 Knoll Dr, Edgartown, MA 02539
    37 Knoll Dr, Edgartown, MA 02539
    /26

    $1,600,000

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    37 Knoll Dr, Edgartown, MA 02539

    TURNKEY KATAMA BEACH RETREAT - OWNER FINANCING POSSIBLETucked away on a quiet sandy road in the heart of Katama, this charming and surprisingly spacious home is move-in or rental-ready—offered fully furnished for immediate enjoyment or income. Featuring 3 bedrooms and 2 full baths, the home includes 1,232 square feet of main-level living plus 520 square feet of finished lower level—perfect for a

    Josseph Barkett Compass

    37 Knoll Dr, Edgartown, MA 02539
  • 50 Canonicus Ave, Oak Bluffs, MA 02557
    50 Canonicus Ave, Oak Bluffs, MA 02557
    50 Canonicus Ave, Oak Bluffs, MA 02557
    /17

    $995,000

    • 2 Beds
    • 1 Bath
    • 952 Sq Ft

    50 Canonicus Ave, Oak Bluffs, MA 02557

    Rare Opportunity to Be in a Special Location and Neighborhood! Loved by generations, this quintessential Vineyard cottage has been in the same family since its creation in 1900. Step back in time and enjoy easy cottage living of yesteryear with modern updates including newer windows and electrical. Nestled under mature trees and just .3 mile to Inkwell Beach, join this close-knit neighborhood and

    Michele Moore Island Real Estate

    50 Canonicus Ave, Oak Bluffs, MA 02557
  • 15 Jernegan Pond Rd, Edgartown, MA 02539
    15 Jernegan Pond Rd, Edgartown, MA 02539
    15 Jernegan Pond Rd, Edgartown, MA 02539
    /31

    $1,750,000

    • 2 Beds
    • 2 Baths
    • 2,042 Sq Ft

    15 Jernegan Pond Rd, Edgartown, MA 02539

    Nestled at the end of a quiet drive, 15 Jernegan Pond Road offers the opportunity to create your Vineyard retreat. The existing home and small barn sit on a private and serene lot overlooking a small, picturesque pond -- an ideal setting for those seeking privacy, natural beauty, and potential. The current structures require significant renovation or rebuild, and with a sewer tie-in, can be

    Lesley Heidt Sandpiper Realty Inc

    15 Jernegan Pond Rd, Edgartown, MA 02539
  • 2 Farm Path, Oak Bluffs, MA 02557
    2 Farm Path, Oak Bluffs, MA 02557
    2 Farm Path, Oak Bluffs, MA 02557
    /37

    $1,995,000

    • 4 Beds
    • 3 Baths
    • 3,058 Sq Ft

    2 Farm Path, Oak Bluffs, MA 02557

    "Turn-key" offering! This custom cape design with a delightful farmer's porch provides ample opportunities to entertain. Set upon nearly an acre of level and landscaped land with irrigation, it abuts the State Forrest, has an open floor plan with cathedral ceilings and skylights. The three bedroom main, has A/C, a finished basement rec room, a large rear deck that spills forth onto a large yard

    Sean Federowicz Landmarks at TODAY Real Estate

    2 Farm Path, Oak Bluffs, MA 02557
  • 211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568
    211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568
    211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568
    /17

    $1,449,000

    • 4 Beds
    • 2 Baths
    • 1,680 Sq Ft

    211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568

    MULTIFAMILY OPPORTUNITYA wonderful compound on the outskirts of town. Set nicely back off the Edgartown Road, the existing home has 4/5 comfortable bedrooms and 2 baths on a nice 1-acre parcel with a good sense of privacy. Behind the home is a fire pit, a shed and another septic system already installed that will serve an additional 5 bedrooms! This property is on a trail to the Bare Hill

    Jim Feiner Feiner Real Estate

    211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568
  • 72 Chappaquiddick Ave, Edgartown, MA 02539
    72 Chappaquiddick Ave, Edgartown, MA 02539
    72 Chappaquiddick Ave, Edgartown, MA 02539
    /32

    $2,999,000

    • 8 Beds
    • 7.5 Baths
    • 3,770 Sq Ft

    72 Chappaquiddick Ave, Edgartown, MA 02539

    WELCOME to this turn-key CHAPPY COMPOUND! This property offers it ALL, with its Six (6) Bedroom, Five (5) bath Primary Home, Two (2) bedroom, Two (2) bath GUEST HOUSE, expansive POOL HOUSE with a bath, kitchenette, large lounge area topped with a cathedral ceiling, a WORKOUT & GAME BARN, a POOL, a VOLLEY BALL COURT and a TENNIS COURT that doubles into TWO PICKLE BALL COURTS, and a BASKETBALL

    Michele Casavant Vineyard Village Realty

    72 Chappaquiddick Ave, Edgartown, MA 02539
  • 114 N Water St, Edgartown, MA 02539
    114 N Water St, Edgartown, MA 02539
    114 N Water St, Edgartown, MA 02539
    /42

    $19,900,000

    • 8 Beds
    • 7.5 Baths
    • 6,041 Sq Ft

    114 N Water St, Edgartown, MA 02539

    The property is currently rented; showings require a minimum of 48 hours’ notice. Move-In Ready – CONSTRUCTION COMPLETE - This stunning 8-bedroom, 7.5-bath generational home, completed in 2025, is fully furnished and move-in ready. The property features a 6-bedroom, 5.5-bath main residence, a 1-bedroom, 1-bath guest house with its own kitchen, and a 2-car carriage house with 1-bedroom living

    Erin Hegarty Compass

    114 N Water St, Edgartown, MA 02539
  • 25 Oak Ave, Oak Bluffs, MA 02557
    25 Oak Ave, Oak Bluffs, MA 02557
    25 Oak Ave, Oak Bluffs, MA 02557
    /40

    $669,000

    • 2 Beds
    • 1 Bath
    • 759 Sq Ft

    25 Oak Ave, Oak Bluffs, MA 02557

    WALK TO THE HARBOR from this level 10,100 sq.ft. quarter acre lot set down a winding avenue off New York Avenue. Currently there's a very cute Victorian Era two story cottage which could be renovated. Alternatively, you have the choice to add on to the exiting building or build a new FIVE (5) BEDROOM home - Possibly more than FIVE (5) bedrooms as it’s not in a Board of Health area of concern -

    Alisan Lohan-Conway Alisan Lohan-Conway Properties

    25 Oak Ave, Oak Bluffs, MA 02557
  • 25 Oak Ave Unit 187, Oak Bluffs, MA 02557
    25 Oak Ave Unit 187, Oak Bluffs, MA 02557
    25 Oak Ave Unit 187, Oak Bluffs, MA 02557
    /3

    $669,000

    • Land
    • 0.23 Acre
    • $2,908,696 per Acre

    25 Oak Ave Unit 187, Oak Bluffs, MA 02557

    WALK TO THE HARBOR from this level 10,100 sq.ft. quarter acre lot. According to the engineer who has percolated the lot, it will allow a FIVE (5) bedroom regular septic system. The Board of Health have stated there are no Board of Health issues or limitations with this property and are deferring to the engineer’s opinion.It may be possible to have more than Five (5) Bedrooms. Water and

    Alisan Lohan-Conway Alisan Lohan-Conway Properties

    25 Oak Ave Unit 187, Oak Bluffs, MA 02557
  • 66 Brush Pond Rd, Oak Bluffs, MA 02557
    66 Brush Pond Rd, Oak Bluffs, MA 02557
    66 Brush Pond Rd, Oak Bluffs, MA 02557
    /24

    $1,699,000

    • 2 Beds
    • 1 Bath
    • 826 Sq Ft

    66 Brush Pond Rd, Oak Bluffs, MA 02557

    **Charming Vineyard Waterfront Cottage in Oak Bluffs**Nestled in a peaceful cul-de-sac in Oak Bluffs, this newly renovated 2-bedroom, 1-bathroom cottage offers the perfect blend of traditional Vineyard charm and modern sensibility. With stunning panoramic views of Brush Pond, the Lagoon, and the iconic Drawbridge, this cozy retreat provides the ultimate setting for both relaxation and outdoor

    Michael Schweikert Ocean Park Realty Inc

    66 Brush Pond Rd, Oak Bluffs, MA 02557

Showing Results 241 - 280, Page 7 of 10

Massachusetts Dukes County

Real Estate & Homes for Sale in Dukes County, MA

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group