Homes with Price Reductions

Properties Available 7 properties available
This charming, single-story cottage blends island simplicity with comfort. Though modest in size, the home maximizes its layout with warm, thoughtfully arranged spaces. At its heart is a welcoming living and dining area that opens directly onto the front porch, creating an easy indoor-outdoor flow. Two bedrooms share an adjoining bath, and a third
Hot HOT 18
Oak Bluffs 862
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$1,300.00 - $4,500.00 / per week + taxes and fees
Beds 3 beds
Baths 2 Full Bath
Sleeps sleeps 6
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Oak Bluffs 862
This charming, single-story cottage blends island simplicity with comfort. Though modest in size, the home maximizes its layout with warm, thoughtfull... Read More
June 2026
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  1 2 3 4 5 $2,800 6
7 8 9 10 11 12 $3,800 13
14 15 16 17 18 19 $3,800 20
21 22 23 24 25 26 $4,300 27
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      1 2 3 $3,800 4
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12 13 14 15 16 17 $4,300 18
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16 17 18 19 20 21 $4,300 22
23 24 25 26 27 28 $3,200 29
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This charming three-bedroom Cape is tucked away in a quiet Edgartown neighborhood, offering an ideal setting to unwind and recharge. Featuring an open-concept living room and dining area, it is perfect for gathering after a day of island adventures. Enjoy preparing meals in the kitchen, relaxing in the comfortable living space, or spending time out
Hot HOT 11
Edgartown 720
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$2,000.00 - $6,100.00 / per week + taxes and fees
Beds 3 beds
Baths 2 Full Bath
Sleeps sleeps 7
Pet Friendly Pets Considered
Not Pet Friendly No Events/Gatherings
Edgartown 720
This charming three-bedroom Cape is tucked away in a quiet Edgartown neighborhood, offering an ideal setting to unwind and recharge. Featuring an open... Read More
June 2026
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  1 2 3 4 5 $4,500 6
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14 15 16 17 18 19 $4,500 20
21 22 23 24 25 26 $5,600 27
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July 2026
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August 2026
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9 10 11 12 13 14 $5,600 15
16 17 18 19 20 21 $5,600 22
23 24 25 26 27 28 $4,500 29
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Lovely Oak Bluffs home located in Sengekontacket. This home offers great space and multiple amenities to enjoy your summer get away. Association tennis courts, fresh pond frontage and access to saltwater pond that leads out to the Vineyard Sound. Your vacation begins the moment you enter the property with an updated kitchen, lovely views of the fr
Hot HOT 13
Oak Bluffs 8174
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$5,000.00 - $10,000.00 / per week + taxes and fees
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps sleeps 8
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Oak Bluffs 8174
Lovely Oak Bluffs home located in Sengekontacket. This home offers great space and multiple amenities to enjoy your summer get away. Association tenni... Read More
June 2026
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  1 2 3 4 5 6
7 8 9 10 11 12 $6,000 13
14 15 16 17 18 19 $7,000 20
21 22 23 24 25 26 $8,000 27
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      1 2 3 $9,500 4
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Built in 1780 and thoughtfully updated for today's living, this downtown Edgartown home blends historic architecture with comfort. The main level offers a light-filled living space furnished with heirloom pieces, high end rugs, and original oil paintings, a formal dining area, and an updated kitchen that leaves nothing to be desired. With two prima
Hot HOT 13
Edgartown Downtown 44
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$10,000.00 - $14,000.00 / per week + taxes and fees
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps sleeps 8
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown Downtown 44
Built in 1780 and thoughtfully updated for today's living, this downtown Edgartown home blends historic architecture with comfort. The main level offe... Read More
June 2026
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  1 2 3 4 5 $11,900 6
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12 13 14 15 16 17 $11,900 18
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Lovely Chilmark cottage tranquilly situated at the end of Abel's Neck Road. The deck that fronts the entire length of the house affords meadow views and Menemsha Pond vistas featuring spectacular sunsets. This well-maintained single-story home boasts 4 bedrooms, two and a half bathrooms, and a wonderful open living/dining/kitchen plan. There are ca
Chilmark 2085
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$5,000.00 - $6,000.00 / per week + taxes and fees
Beds 4 beds
Baths 2 Full Bath
Sleeps sleeps 8
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Chilmark 2085
Lovely Chilmark cottage tranquilly situated at the end of Abel's Neck Road. The deck that fronts the entire length of the house affords meadow views a... Read More
June 2026
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Vineyard Haven's Historic District is host to the 1805 Edmund Crowell House. This 5-bedroom home overlooks Vineyard Haven harbor, just steps from the town beach. Inside enjoy the preserved vintage features such as high ceilings, wide-board floors, and parlor with shiplap wainscoting. Cook in the large well-appointed kitchen with "antique" applia
Vineyard Haven 1244
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$7,000.00 - $8,500.00 / per week + taxes and fees
Beds 5 beds
Baths 4 Full Bath
Sleeps sleeps 8
Pet Friendly Pets Considered
Not Pet Friendly No Events/Gatherings
Vineyard Haven 1244
Vineyard Haven's Historic District is host to the 1805 Edmund Crowell House. This 5-bedroom home overlooks Vineyard Haven harbor, just steps from the... Read More
June 2026
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  1 2 3 4 5 $7,500 6
7 8 9 10 11 12 $7,500 13
14 15 16 17 18 19 $7,500 20
21 22 23 24 25 26 $7,500 27
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      1 2 3 $7,900 4
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23 24 25 26 27 28 $7,900 29
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Another Katama beauty! Inside you will find a first floor with lovely furnishings, a chefs kitchen, dining room, living room and a bathroom. All of the luxurious four bedrooms are on the second floor. The king primary suite has an office area, tv, and balcony. The remaining three bedrooms have access to a hall bathroom. There are 2 sets of washers
Hot HOT 17
Edgartown Katama 7200
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$3,600.00 - $9,000.00 / per week + taxes and fees
Beds 4 beds
Baths 3 Full Bath
Sleeps sleeps 8
Not Pet Friendly Pets Not Allowed
Not Pet Friendly No Events/Gatherings
Edgartown Katama 7200
Another Katama beauty! Inside you will find a first floor with lovely furnishings, a chefs kitchen, dining room, living room and a bathroom. All of th... Read More
June 2026
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  1 2 3 4 5 $5,850 6
7 8 9 10 11 12 $5,850 13
14 15 16 17 18 19 $8,100 20
21 22 23 24 25 26 $8,100 27
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      1 2 3 $8,100 4
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16 17 18 19 20 21 $9,000 22
23 24 25 26 27 28 $8,100 29
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