Dukes, MA Homes

/42
$2,675,000
- 6 Beds
- 4.5 Baths
- 2,970 Sq Ft
128 W Spring St, Vineyard Haven, MA 02568

A Rare Compound Opportunity in the Heart of Vineyard Haven - 128 & 136 Spring Street - Two adjacent properties being sold together create a flexible compound just moments from downtown Vineyard Haven. The 4-bedroom, 2-1/2 bath main house also includes a separate, 1-bedroom in-law/nanny apartment with a full bath. The guest house has 1 bedroom and 1 bath, with a 4-bedroom septic system allowing

David Dickinson Compass

128 W Spring St, Vineyard Haven, MA 02568
/15
$5,000 per month
- 4 Beds
- 2.5 Baths
- 2,300 Sq Ft
- House for Rent
6 Briar Path, Aquinnah, MA 02535

THIS IS A WEEKLY SUMMER RENTAL ONLY. PRICES ARE WEEKLY NOT MONTHLY. Down a private country road, this bright and breezy post and beam home sits on a 3-acre rolling wooded parcel. With southern views of the Atlantic Ocean, it's just a short drive or bike to Philbin and Lobsterville beaches and Gay Head cliffs. This very Vineyard house offers three levels of living space, chef's kitchen, spacious

Karen Overtoom Karen M. Overtoom R.E.

6 Briar Path, Aquinnah, MA 02535
/17
$700,000 Sold Jun 20, 2025
- 725 Sq Ft
- $966/SF
- 111 Days On Market
- 3 Beds
- 1 Bath
- Built 1870
2 Fisk Ave, Oak Bluffs, MA 02557

Gingerbread Cottage full of character and personality! Part of Martha's Vineyard Camp Meeting Association, this Oak Bluffs seasonal antique with beautiful trim and scrollwork sits on a lovely little avenue. The cottage features charming period details, a covered front porch with rocking chairs & upper balcony. Step inside the unique front door into a cozy living room enhanced by beamed ceiling,

Julie Walker Century 21 North East

2 Fisk Ave, Oak Bluffs, MA 02557

/14
Est $2,704,037 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,926 Sq Ft
30 Pond Ln, Vineyard Haven, MA 02568

30 Pond Ln, Vineyard Haven, MA 02568

/36
$3,250,000
- 4 Beds
- 4 Baths
- 2,515 Sq Ft
300 North Rd, Chilmark, MA 02535

Winding tree lined driveway off North Rd brings you to this commanding, custom designed residence built by a top tier island builder. This home is set on over 4 private acres of rolling meadows and big sky views. Main living space is all on one level which includes primary bedroom with en-suite bath, large living area with fireplace, bright sunroom or second living room, custom kitchen and

Rebecca V Conroy Conroy & Company R.E., Inc.

300 North Rd, Chilmark, MA 02535
/42
$19,000 per month
- 6 Beds
- 6.5 Baths
- 6,950 Sq Ft
- House for Rent
40 Sweet William Way, West Tisbury, MA 02575

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY! This stunning home is situated right in the heart of West Tisbury, yet set back enough for a completely private feel. On a property that encompasses 10 acres with your own private pond, you will feel the stress melt away as soon as you get to this luxury vacation home. Keys to private Quansoo Beach Association come with the house. Spend your days on the

Karen Overtoom Karen M. Overtoom R.E.

40 Sweet William Way, West Tisbury, MA 02575
/6
$430,000 Sold Jun 18, 2025
- Land
- 1.40 Acres
- $307,143 per Acre
- 0 Days On Market
0 Quansoo Beach Lot Unit 48 43485, Chilmark, MA 02535

Not listed in LINK.

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0 Quansoo Beach Lot Unit 48 43485, Chilmark, MA 02535

/36
Est $1,270,314 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,780 Sq Ft
16 Rock Pond Rd, Vineyard Haven, MA 02568

16 Rock Pond Rd, Vineyard Haven, MA 02568

/24
$2,500,000
- 4 Beds
- 4 Baths
- 2,202 Sq Ft
2 Farmers Rd, Edgartown, MA 02539

This house and guesthouse combination are situated in a very special location. Located equidistant between town and South Beach. The neighboring properties are quite impressive. Across the lane is over 28 acres of Edgartown Conservation Commission land. The property currently has two dwellings, a three bedroom main house and a one bedroom guesthouse. A separate toolshed has an additional finished

Neal Stiller Cronigs Real Estate

2 Farmers Rd, Edgartown, MA 02539
/39
$46,000 per month
- 6 Beds
- 4.5 Baths
- 3,800 Sq Ft
- House for Rent
99 Pond Road Wt104, West Tisbury, MA 02575

THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!! Beautiful bright sunny home with open concept living. Main floor features a gourmet kitchen with stainless appliances, breakfast bar and formal dining table to seat 10. Large glass sliders open up to expansive views of the deck, pool and pasture beyond. Also on the main level is a separate living area with large screen TV, powder room, and den with twin

Karen Overtoom Karen M. Overtoom R.E.

99 Pond Road Wt104, West Tisbury, MA 02575
/30
$1,525,000 Sold Jun 18, 2025
- 2,016 Sq Ft
- $756/SF
- 110 Days On Market
- 4 Beds
- 3 Baths
- Built 1967
54 Lake St, Vineyard Haven, MA 02568

Welcome to this delightful 4-bedroom, 3-bathroom home, perfectly situated in a highly desirable location where convenience meets tranquility. Just a short stroll from town, restaurants, Tashmoo Landing, and tennis courts, this property offers the ideal combination of lifestyle and leisure.Step onto the covered front porch and into a warm, inviting space featuring two living rooms—one on each

Jon Hartzband Martha's Vineyard Island-Wide Realty

54 Lake St, Vineyard Haven, MA 02568

/40
Est $1,944,286 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 1 Sq Ft
179 Main St, Vineyard Haven, MA 02568

179 Main St, Vineyard Haven, MA 02568

/36
$2,500,000
- 4 Beds
- 3 Baths
- 2,350 Sq Ft
16 South Rd, Chilmark, MA 02535

Where Vineyard history meets pastoral beauty.Classic, lovingly restored 1800’s Chilmark farmhouse with multiple outbuildings, which includes a large barn with second floor loft, a run-in barn with two horse stalls, both overlook an expansive, pastoral fenced pasture for horses to run or field games to be played. This historic farmhouse home offers four bedrooms, three baths and has been

Michele Casavant Vineyard Village Realty

16 South Rd, Chilmark, MA 02535
/3
$13,200 per month
- 2 Beds
- 2 Baths
- 1,344 Sq Ft
- House for Rent
224 N Rd Ch248, Chilmark, MA 02535

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! A modern summer retreat is nestled high on a knoll off North Rd in picturesque Chilmark. Here in this stunning contemporary ranch you will find the upmost in Luxury. Each room is exciting, charming and has a simplistic yet artistic style. The entire house is accented with beautiful light pine flooring that pairs perfectly with the expansive main room.

Karen Overtoom Karen M. Overtoom R.E.

224 N Rd Ch248, Chilmark, MA 02535
/20
$821,000 Sold Jun 17, 2025
- Land
- 1.40 Acres
- $586,429 per Acre
- 0 Days On Market
168 Charles Neck Way Unit 49, Vineyard Haven, MA 02568

Large 1.4 Acre Corner lot in Vineyard Meadow Farms South side of West Tisbury Road. Private, flat, level parcel, paved dead end road with no unnecessary through traffic. Six bedrooms, a 3,000SF Main House, a 2,000SF detached/attached Secondary Building allowed per the Town. Pool allowed with standard Special permit. Centrally located to all Island Towns. Great neighborhood. Great location with

Janna O'Loughlin Portfolio Real Estate, Inc.

168 Charles Neck Way Unit 49, Vineyard Haven, MA 02568

/23
Est $2,154,681 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,704 Sq Ft
31 Pulpit Ln, Edgartown, MA 02539

31 Pulpit Ln, Edgartown, MA 02539

/34
$2,995,000
- 3 Beds
- 2.5 Baths
- 1,964 Sq Ft
21 Kitts Field Cir, Edgartown, MA 02539

Tastefully renovated, stylishly decorated with the beach in mind, superbly maintained and thoughtfully expanded - all these attributes and more apply. The list of improvements is long and, yet the property has not reached its maximum potential. It is connected to town sewer and is allowed up to 6 bedrooms. It is a conforming lot according to town zoning, which allows for greater flexibility.

Lynn Buder Sandpiper Realty Inc

21 Kitts Field Cir, Edgartown, MA 02539
/27
$18,840 per month
- 3 Beds
- 2.5 Baths
- House for Rent
21 William St Vh430, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,710. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely elegant home with wonderful art and furnishings. Once you step in the front door you will fall in love with this lovely home. Each room is a delight. Large nicely appointed kitchen with easy access to a beautiful dining room. A formal living room is next to a less

Karen Overtoom Karen M. Overtoom R.E.

21 William St Vh430, Tisbury, MA 02568
/18
$1,219,000 Sold Jun 16, 2025
- 1,512 Sq Ft
- $806/SF
- 99 Days On Market
- 3 Beds
- 2 Baths
- Built 1986
108 Charles Neck Way, Vineyard Haven, MA 02568

This charming reverse-style home is ideally located near Long Point Beach and offers a perfect blend of comfort and functionality for year-round living or seasonal getaways. The first floor features three spacious bedrooms, a full bath, and a convenient laundry room. On the second floor, you'll find soaring cathedral ceilings and an open-concept living area, complete with a cozy living room,

Alyssa Halisky Wallace & Co. Sotheby's

108 Charles Neck Way, Vineyard Haven, MA 02568

/48
Est $2,960,910 Not Listed For Sale
- 6 Beds
- 3.5 Baths
- 3,440 Sq Ft
8 Coffins Field Rd, Edgartown, MA 02539

8 Coffins Field Rd, Edgartown, MA 02539

/40
$2,590,000
- 4 Beds
- 3.5 Baths
- 3,052 Sq Ft
27 Watcha Path, Edgartown, MA 02539

STYLISH VINEYARD LIVING WITH EXCEPTIONAL OUTDOOR AMENITIES. This beautifully landscaped coastal-style home is set on three acres just off the bike path, offering easy access to all Island towns. A heated saltwater pool, expansive decking, and outdoor gathering spaces create the perfect setup for Vineyard summers. The home offers 4 bedrooms and 3.5 baths, including two primary suites—one on each

Jennifer O'hanlon Compass

27 Watcha Path, Edgartown, MA 02539
/25
$10,800 per month
- 2 Beds
- 4 Baths
- 1,800 Sq Ft
- House for Rent
256 Sandpiper Lane Vh417, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This well appointed condo will make you feel comfortable and at home the moment you walk in. Swimming, kayaking, tennis, walking trails, and shopping are all at your finger tips. Mink Meadows Golf Course is just a stroll down the street as well. Enjoy all the Island has

Karen Overtoom Karen M. Overtoom R.E.

256 Sandpiper Lane Vh417, Tisbury, MA 02568
/34
$4,000,000 Sold Jun 13, 2025
- 4,000 Sq Ft
- $1000/SF
- 238 Days On Market
- 4 Beds
- 5 Baths
- Built 2004
515 State Rd, Aquinnah, MA 02535

Set atop a hill overlooking Menemsha, Quitsa and Squibnocket Pond sits this stunning home. A masterful combination of up-island elegance, fine craftsmanship and expert design sets this contemporary apart from other high end homes. Being sold completely turn key, this house was built with the finest of materials and finishes and with entertaining in mind. Large living room with magnificent

Rebecca V Conroy Conroy & Company R.E., Inc.

515 State Rd, Aquinnah, MA 02535

/49
Not Listed For Sale
- 4 Beds
- 4 Baths
- 2,092 Sq Ft
670 State Rd, Vineyard Haven, MA 02568

670 State Rd, Vineyard Haven, MA 02568

/46
$2,495,000
- 5 Beds
- 4 Baths
- 3,873 Sq Ft
50 Hidden Cove Rd, Edgartown, MA 02539

Sengekontacket–Walk into a “turn-key” opportunity in the desirable Hidden Cove community, just steps (.3 miles) from Sengekontacket Pond with access to State Beach and Nantucket Sound beyond. The lovingly-maintained 4 bedroom, 2.5 bath, 2 car garage main home sits high on the 1.5 acre property offering an abundance of natural light that flows into the open living and entertaining spaces. The

Sean Federowicz Landmarks at TODAY Real Estate

50 Hidden Cove Rd, Edgartown, MA 02539
/18
$10,000 per month
- 3 Beds
- 1.5 Baths
- 1,144 Sq Ft
- House for Rent
100 Franklin Terrace Vh411, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This charming 3 bedroom home offers open living, dining and kitchen space that open to a screened-in porch and patio. You are located in a peaceful setting yet with-in walking distance to Lake Tashmoo, town beaches, and the Vineyard Haven Village for dining, shopping and

Karen Overtoom Karen M. Overtoom R.E.

100 Franklin Terrace Vh411, Tisbury, MA 02568
/20
$1,150,000 Sold Jun 13, 2025
- 1,374 Sq Ft
- $837/SF
- 43 Days On Market
- 3 Beds
- 2 Baths
- Built 1981
46 Old Coach Rd, Vineyard Haven, MA 02568

Charming and Spacious 3-Bedroom Cape with large Loft and Deck Welcome to your dream West Tisbury home! This comfortable and spacious 3-bedroom, 2-bath Cape boasts a thoughtfully designed floor plan perfect for comfortable living. The first-floor features two bedrooms and a full bath, ideal for use as sleeping quarters or a home office. Moving to the second floor, discover privacy with a third

Lisa Gilberto C McManus Realty Group

46 Old Coach Rd, Vineyard Haven, MA 02568

/75
Est $4,011,141 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,362 Sq Ft
4 Tilton Rd, Chilmark, MA 02535

4 Tilton Rd, Chilmark, MA 02535

/39
$2,900,000
- 4 Beds
- 3 Baths
- 2,562 Sq Ft
21 Woodlawn Ave, Vineyard Haven, MA 02568

Experience the perfect blend of coastal charm and modern sophistication in this beautifully designed Vineyard Haven home. Ideally situated in-town, this 4-bedroom, 3-bath home offers a comfortable, easy flowing layout, complemented by gleaming hardwood floors and a warm, inviting atmosphere. Located just a short stroll from the ferry, vibrant shops, restaurants and the Vineyard Haven Yacht Club,

Beth Welch Viewpoints; Bobbi Flake Reed, Inc.

21 Woodlawn Ave, Vineyard Haven, MA 02568
/28
$32,000 per month
- 4 Beds
- 4 Baths
- 3,200 Sq Ft
- House for Rent
37 Mempremagog Ave Vh410, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous custom designed and decorated four bedroom home is located in a wooded setting that offers total privacy and is with-in walking distance to a private association beach. And yet is only 3 miles from downtown Vineyard Haven. This lovely home offers a gourmet eat-in

Karen Overtoom Karen M. Overtoom R.E.

37 Mempremagog Ave Vh410, Tisbury, MA 02568
/39
$2,750,000 Sold Jun 10, 2025
- 1,008 Sq Ft
- $2728/SF
- 0 Days On Market
- 3 Beds
- 2 Baths
- Built 1953
25 Oxcart Rd, Aquinnah, MA 02535

Vineyard Sound waterfront! This is what summer on the Vineyard is all about. Contemporary beach house set in the dunes on 4.6 acres amongst beach plum bushes and windswept beach grass. Open concept interior with a wall of windows facing the Vineyard Sound and Elizabeth Islands. Two guest rooms on the main level and a top floor primary bedroom with deck for star gazing and glorious sunsets. A

Rebecca V Conroy Conroy & Company R.E., Inc.

25 Oxcart Rd, Aquinnah, MA 02535

/52
Est $5,460,636 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 3,740 Sq Ft
12 Plantingfield Wood Cir, Edgartown, MA 02539

12 Plantingfield Wood Cir, Edgartown, MA 02539

/47
$2,500,000
- 3 Beds
- 3 Baths
- 1,784 Sq Ft
12 Lobsterville Rd, Aquinnah, MA 02535

12 Lobsterville Rd in Aquinnah is a uniquely designed contemporary home set on 2.6 acres of lush grounds with large tracts of conservation land nearby. Open concept living, dining, kitchen on the second floor with unobstructed ocean views of Vineyard Sound. Spacious deck for sunset viewing and grassy lawn for sundown games. Walking distance to Lobsterville Beach and a short bike ride to the

Tina Palmer Conroy & Company R.E., Inc.

12 Lobsterville Rd, Aquinnah, MA 02535
/15
$7,500 per month
- 2 Beds
- 1 Bath
- 800 Sq Ft
- House for Rent
83 Ashtons Way, Vineyard Haven, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $1,875. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This two bedroom cottage is set in a private setting in the woods, just a short distance to downtown Vineyard Haven. Sleeps four comfortably, open living space, deck and outside shower. If rented with the main house, access to private association beach and golf would be

Karen Overtoom Karen M. Overtoom R.E.

83 Ashtons Way, Vineyard Haven, MA 02568
/31
$1,750,000 Sold Jun 06, 2025
- 1,850 Sq Ft
- $946/SF
- 226 Days On Market
- 3 Beds
- 2 Baths
- Built 1981
97 Snake Hollow, Vineyard Haven, MA 02568

Nestled in a private neighborhood in Vineyard Haven conveniently located to the ferry and town for plenty of shopping and dining, this renovated home is move-in ready and sited on 1.5 generous acres. There are two entrances to the home. The most operational is off the side deck where you enter the fabulous must-have mudroom. Offering separation from the main part of the home is a dramatic

Stephanie Roache Donnelly + Co.

97 Snake Hollow, Vineyard Haven, MA 02568

/27
Est $1,373,100 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,228 Sq Ft
24 Alyssa Ln, Vineyard Haven, MA 02568

24 Alyssa Ln, Vineyard Haven, MA 02568

/35
$2,495,000
- 4 Beds
- 3 Baths
- 2,968 Sq Ft
9 Beetlebung Grove Way, Chilmark, MA 02535

Beautifully sited on 3.4 acres, this distinctive Chilmark home offers a rare blend of privacy, comfort, and expansive living space, ideal for entertaining, both inside and outside. From the welcoming foyer, step into the dramatic vaulted living room, where wood-paneled ceilings, a gas fireplace, and abundant natural light from skylights and picture windows create a warm and inviting atmosphere.

Stephanie Roache Donnelly + Co.

9 Beetlebung Grove Way, Chilmark, MA 02535
/40
$32,500 per month
- 6 Beds
- 4.5 Baths
- 3,222 Sq Ft
- House for Rent
100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living

Karen Overtoom Karen M. Overtoom R.E.

100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568
/42
$2,400,000 Sold Jun 05, 2025
- 3,200 Sq Ft
- $750/SF
- 49 Days On Market
- 3 Beds
- 4.5 Baths
- Built 2014
6 Martha's Park Rd, Oak Bluffs, MA 02557

Must see stunning “reverse” layout (kitchen and main living spaces upstairs for the views) contemporary home with breathtaking water views and a thoughtfully designed layout in the exclusive Harthaven community! This spacious property features open kitchen concept with marble counter tops and stainless steel appliances, comfortable living areas, a bonus room (with full bathroom), food prep,

Jennifer B. DaSilva Compass

6 Martha's Park Rd, Oak Bluffs, MA 02557

/21
Est $1,585,977 Not Listed For Sale
- 4 Beds
- 3 Baths
- 1,583 Sq Ft
8 Old Purchase Way, Edgartown, MA 02539

8 Old Purchase Way, Edgartown, MA 02539

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