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Contemporary, Spacious Home, Heated Pool,18 x 40, Luxury Amenities, Screened Porch, Patio and Private Yard

This beautiful new luxury home with an 18 x 40 heated pool which is located a quick bike ride to Morning Glory Farm and close to historic Edgartown Village, is...Read more

Location: 
Edgartown
Sleeps: 
12
Bedrooms: 
6
Baths: 
4
Price Range:
$6,500 - $18,750
June 2027
SuMoTuWeThFrSaWeek
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$9,000
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$10,250
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$13,250
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$15,500
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 $17,500
July 2027
SuMoTuWeThFrSaWeek
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$17,500
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$17,500
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$17,500
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$18,000
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$18,250
August 2027
SuMoTuWeThFrSaWeek
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$18,750
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$18,750
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$18,750
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$16,500
29
30
31
 $12,000
September 2027
SuMoTuWeThFrSaWeek
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$12,000
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Clean Fee: 
$750 per week
Tax: State & Local: 
11.7

Pool is heated to 82 degrees in July and August included in rental rate. 

 

Pool heat fee May (after 5/15), June, Sept $350 per week. Pool heated to 82.

 

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Gorgeous in Town Home, Heated Saltwater Pool, 16 x 32, Pool Cabana/Office Space, 5 minute walk to the heart of Edgartown Village

Sansouci  Located on a quiet cul de sac that is a 5-minute walk to restaurants and shops in downtown Edgartown. It’s a 10-minute walk to the harbor and a 15-minute walk...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$24,000 - $24,000
June 2027
SuMoTuWeThFrSaWeek
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 $22,000
July 2027
SuMoTuWeThFrSaWeek
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2
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$22,000
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$22,000
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$22,000
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$22,000
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30
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$22,000
August 2027
SuMoTuWeThFrSaWeek
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$24,000
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$24,000
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$24,000
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$24,000
29
30
31
 
September 2027
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Clean Fee: 
$650 per week
Tax: State & Local: 
11.7

Pool heated to 82 in July & August included in the rental rate. 

Pool heated to 82 in June & September, additional $250 per week, May & October, additional $350 per week 
 

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Gracious Village Area 5 Bedroom Home, Light Filled Interior, Mulitple Living Spaces, Large Landscaped Yard, Located on Quiet Side St, 5 min Walk to Main St.

Stunning Edgartown Village Home! This meticulously maintained and newly updated property offers multiple living areas, 5 bedrooms, and 3.5 baths, surrounded by a lushly landscaped yard. Just a 5-minute walk...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
5
Baths: 
3
Price Range:
$8,000 - $14,500
June 2027
SuMoTuWeThFrSaWeek
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$8,000
6
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$8,000
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$8,000
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21
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25
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$10,000
27
28
29
30
 $10,000
July 2027
SuMoTuWeThFrSaWeek
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2
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$10,000
4
5
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$10,000
11
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$10,000
18
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$14,500
25
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30
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$14,500
August 2027
SuMoTuWeThFrSaWeek
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$14,500
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$14,500
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$14,500
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$12,500
29
30
31
 $10,000
September 2027
SuMoTuWeThFrSaWeek
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$10,000
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$8,000
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$8,000
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$8,000
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30
 $8,000
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

 

Parking for 3 cars, no on street parking

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Stylish and Beautifully Decorated Summer Residence, Screened Porch, Spacious Deck, WiFi

Centrally located mid-island, this beautifully appointed home features an open design kitchen, dining, and living areas for easy entertaining with family and friends.  French doors off of the living area...Read more

Location: 
Edgartown
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$2,100 - $5,000
June 2027
SuMoTuWeThFrSaWeek
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3
4
5
$2,350
6
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$2,350
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$2,350
20
21
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25
26
$3,700
27
28
29
30
 $4,500
July 2027
SuMoTuWeThFrSaWeek
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2
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$4,500
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$4,500
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$4,500
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$4,500
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30
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$4,500
August 2027
SuMoTuWeThFrSaWeek
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$5,000
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$5,000
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$5,000
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$5,000
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30
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 $5,000
September 2027
SuMoTuWeThFrSaWeek
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$5,000
5
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$2,350
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$2,350
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$2,350
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 $2,100
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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Cottage with Screened Porch, Close to Menemsha Village Area and just a Short Drive to Lucy Vincent Beacn

Menemsha Crossroads sweet cottage in a private wooded area, perfect for a family of four. Features 2 bedrooms, a primary with bath, and the 2nd bedroom uses a hall bath. The...Read more

Location: 
Chilmark
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$2,500 - $3,500
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$2,500
6
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$2,500
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$2,500
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$2,500
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29
30
 $3,000
July 2027
SuMoTuWeThFrSaWeek
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2
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$3,000
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$3,000
11
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$3,000
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$3,000
25
26
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30
31
$3,000
August 2027
SuMoTuWeThFrSaWeek
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2
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$3,500
8
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$3,500
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$3,500
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$3,500
29
30
31
 $2,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$2,500
5
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$2,500
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$2,500
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25
$2,500
26
27
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29
30
 $2,500
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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Luxury Modern Farm House Design, Waterfront Pear Tree Cove on the Tisbury Great Pond, Rental Boat Access to South Shore Beach, Spectacular Area for Kayak Enthusiasts

New exquisite contemporary farmhouse design! Waterfront on the Tisbury Great Pond with access via boat rentals to gorgeous South Shore Beach. The beach area on the pond provides a great play space...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$9,500 - $9,500
June 2027
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$550 per week
Tax: State & Local: 
11.7
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Menemsha

Magical Menemsha Cottage with water views of the Elizabeth Islands and harbor. The wooded property encompasses 3 private acres and is within walking distance to the village of Menemsha and...Read more

Location: 
Chilmark
Sleeps: 
7
Bedrooms: 
3
Baths: 
1
Price Range:
$4,350 - $6,310
June 2027
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July 2027
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August 2027
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September 2027
SuMoTuWeThFrSa
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Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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CLASSIC, IN-TOWN EDGARTOWN, ENGLISH-COUNTRY CHIC LUXURY HOME WITH POOL AND MANICURED GROUNDS

Exquisite home in the village of Edgartown that exudes classic taste with English-Country styling.  This in-town location makes it easy to stroll down to dinner on the harbor or walk...Read more

Location: 
Edgartown
Sleeps: 
12
Bedrooms: 
7
Baths: 
6
Price Range:
$10,500 - $29,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$12,500
6
7
8
9
10
11
12
$12,500
13
14
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16
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18
19
$15,000
20
21
22
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25
26
$25,000
27
28
29
30
 $29,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$29,500
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5
6
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9
10
$29,500
11
12
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$29,500
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19
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23
24
$29,500
25
26
27
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29
30
31
$29,500
August 2027
SuMoTuWeThFrSaWeek
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$35,000
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14
$35,000
15
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$35,000
22
23
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27
28
$35,000
29
30
31
 $12,500
September 2027
SuMoTuWeThFrSaWeek
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2
3
4
$12,500
5
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$10,500
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$10,500
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$10,500
26
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29
30
 $10,500
Clean Fee: 
$950 per week
Tax: State & Local: 
11.7
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Stunning, Charming, Historic Luxury Home in Edgartown Village Center, Newly Remodeled

This beautifully remodeled historic home is nestled in the heart of Edgartown Village and boasts 4 bedrooms and 4.5 luxurious baths, complete with an array of inviting indoor and outdoor...Read more

Location: 
Edgartown
Bedrooms: 
5
Baths: 
4
Price Range:
$10,000 - $16,000
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$14,000
6
7
8
9
10
11
12
$14,000
13
14
15
16
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19
$14,000
20
21
22
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25
26
$19,000
27
28
29
30
 $19,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$19,000
4
5
6
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10
$19,000
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$19,000
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$19,000
25
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30
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$19,000
August 2027
SuMoTuWeThFrSaWeek
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$20,000
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$20,000
15
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$20,000
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$20,000
29
30
31
 $12,000
September 2027
SuMoTuWeThFrSaWeek
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$12,000
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$12,000
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$12,000
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$12,000
26
27
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29
30
 $12,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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Lovely Oak Bluffs Escape, 3 Bedrooms in Main House, 2 Bedrooms over Garage, 3.5 Baths Multiple Living Spaces, Walk to Oak Bluffs Center, 1 Mile

Nestled on a tranquil cul-de-sac in the heart of Oak Bluffs, this meticulously renovated Modern Colonial offers a special Martha's Vineyard experience. Thoughtfully reimagined in 2025, the property encompasses a...Read more

Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$7,000 - $10,000
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$7,500
6
7
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9
10
11
12
$7,000
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$7,000
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21
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25
26
$8,400
27
28
29
30
 $10,000
July 2027
SuMoTuWeThFrSaWeek
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2
3
$10,000
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$10,000
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$9,000
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$10,000
25
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$10,000
August 2027
SuMoTuWeThFrSaWeek
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$12,000
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$14,000
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$12,000
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$10,000
29
30
31
 $8,400
September 2027
SuMoTuWeThFrSaWeek
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2
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4
$8,400
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$7,000
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$7,000
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$7,000
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30
 $7,000
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7

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