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Exquisite Designer Home, 10 minute Walk to Oak Bluffs Town Center, Screened Porch, Patio Dining Area, Landscaped Yard, Professionally Decorated, AC

Quietly nestled on a quiet street just on the outskirts of town, this brightly lit home features a mix of coastal details and traditionally styled upscale furnishings for your comfort. The...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$5,050 - $6,000
June 2025
SuMoTuWeThFrSaWeek
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 $6,000
July 2025
SuMoTuWeThFrSaWeek
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$6,000
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$6,000
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$6,000
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$6,000
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 $6,000
August 2025
SuMoTuWeThFrSaWeek
 1
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$6,000
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$6,000
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$6,000
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$6,000
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$6,000
31
 $6,000
September 2025
SuMoTuWeThFrSaWeek
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$6,000
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$5,100
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$5,100
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$5,100
28
29
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 $5,100
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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Recently Updated & Perfect Katama Location, 3 Minute Drive to South Beach, 5 minute Drive to Edgartown Village

Contemporary Beach Home with easy access to South Beach and all that Edgartown Village has to offer.

The modern and bright main living area is an open concept with a...Read more

Location: 
Katama
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$4,000 - $5,750
June 2025
SuMoTuWeThFrSaWeek
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29
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 $4,750
July 2025
SuMoTuWeThFrSaWeek
 1
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3
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$4,750
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$4,750
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$4,750
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$4,750
27
28
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30
31
 $5,750
August 2025
SuMoTuWeThFrSaWeek
 1
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$5,750
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$5,750
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$5,750
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$5,750
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$5,750
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
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$4,000
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$4,000
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$4,000
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29
30
 $4,000
Clean Fee: 
$325 per week
Tax: State & Local: 
11.7
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Beautiful Newly Updated Cape Style Home, Association Tennis Courts 2 min Walk, Biking & Hiking Trails, Beaches 10 minutes from House

This lovely 3 bedroom, 2.5 bath home features sun-filled rooms, an open floor plan throughout, screened porch set up as a summer living room with a sectional sofa, and a...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$4,200 - $6,000
June 2025
SuMoTuWeThFrSaWeek
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 $6,000
July 2025
SuMoTuWeThFrSaWeek
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$6,000
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$6,000
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$6,000
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$6,000
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31
 $6,000
August 2025
SuMoTuWeThFrSaWeek
 1
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$6,000
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$6,000
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$6,000
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$6,000
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$6,000
31
 $5,400
September 2025
SuMoTuWeThFrSaWeek
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$5,400
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$5,400
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$5,400
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$5,400
28
29
30
 $5,000
Clean Fee: 
$400
Tax: State & Local: 
11.7
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Outstanding In-town Home, Gorgeous Professionally Landscaped Yard, 5 Min walk to Main Street Shops & Restaurants

Located on a quiet street in the Edgartown Village area, this lovely 5 bedroom, 3 bath Home has been all newly updated. The home is bordered by lush lawn, privacy fencing...Read more

Location: 
Edgartown
Sleeps: 
9
Bedrooms: 
5
Baths: 
3
Price Range:
$6,000 - $14,000
June 2025
SuMoTuWeThFrSaWeek
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 $11,000
July 2025
SuMoTuWeThFrSaWeek
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$11,000
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$11,000
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$11,000
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$11,000
27
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31
 $12,250
August 2025
SuMoTuWeThFrSaWeek
 1
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$12,250
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$12,250
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$13,000
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$15,000
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$12,000
31
 $6,000
September 2025
SuMoTuWeThFrSaWeek
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$6,000
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$6,000
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$6,000
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$6,000
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 $6,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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Charming, 4-bedroom Oak Bluffs Home, pristinely maintained!  The large wraparound porch and backyard patio areas provide the perfect venue for relaxing when not at the beach or out and about...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$2,000 - $5,500
June 2025
SuMoTuWeThFrSaWeek
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 $3,500
July 2025
SuMoTuWeThFrSaWeek
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$3,500
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$3,000
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$3,000
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$3,000
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 $3,000
August 2025
SuMoTuWeThFrSaWeek
 1
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$3,000
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$5,000
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$5,750
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$5,750
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$5,250
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
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$4,000
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$2,000
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$2,000
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$2,000
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 $2,000
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

Parking for two cars only, no on-street parking!

 

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Luxurious Village Home, Heated Gunite Pool, Acres of Privacy, Walk to Fuller St Beach and Main Street

Edgartown Village Luxury Home featuring a 6 bedroom Main & Guest House, Heated Pool, Cabana & Hot Tub, Water views across Eel Pond to Nantucket Sound and Pristinely Landscaped Grounds. Walk...Read more

Location: 
Edgartown
Sleeps: 
12
Bedrooms: 
6
Baths: 
6
Price Range:
$45,000 - $45,000
June 2025
SuMoTuWeThFrSaWeek
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 $45,000
July 2025
SuMoTuWeThFrSaWeek
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$45,000
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$45,000
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$45,000
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$45,000
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 $45,000
August 2025
SuMoTuWeThFrSaWeek
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$45,000
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$45,000
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$45,000
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$45,000
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$45,000
31
 $45,000
September 2025
SuMoTuWeThFrSaWeek
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$45,000
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$45,000
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$45,000
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$45,000
28
29
30
 
Clean Fee: 
$675 per week
Tax: State & Local: 
11.7

2 week stay required!  

Pool Heated to 82 in July & August included, shoulder weeks please inquire with Agent!

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Adorable Oak Bluffs Cottage Just Over a Mile to the Village Center and Town Beaches, Porch, Deck, 4 Bedrooms, 2 Baths

Nestled on a quiet street, this recently updated residence boasts delightful indoor and outdoor living areas. The entrance porch offers cozy seating with wicker chairs and a small dining table that...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$2,300 - $5,700
June 2025
SuMoTuWeThFrSaWeek
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 $4,200
July 2025
SuMoTuWeThFrSaWeek
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$4,200
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$4,200
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$4,200
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$4,200
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 $4,200
August 2025
SuMoTuWeThFrSaWeek
 1
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$4,200
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$5,000
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$5,700
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$5,000
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$5,000
31
 $4,900
September 2025
SuMoTuWeThFrSaWeek
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3
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$4,900
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$3,000
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$3,000
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$3,000
28
29
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 $2,300
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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Luxurious Katama Retreat, Heated Pool, Cabana with Fireplace, Expansive Deck & Patio, Screened Porch

Impressive new luxury Katama retreat features sleek contemporary interior design, 3 lush acres of quiet privacy, a heated, eco-friendly saltwater 20 x 40 gunite pool, a separate cabana pool building with...Read more

Location: 
Katama
Sleeps: 
10
Bedrooms: 
5
Baths: 
4
Price Range:
$21,500 - $27,500
June 2025
SuMoTuWeThFrSaWeek
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 $21,500
July 2025
SuMoTuWeThFrSaWeek
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3
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5
$21,500
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12
$21,500
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$21,500
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$25,250
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31
 $26,500
August 2025
SuMoTuWeThFrSaWeek
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$26,500
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$27,500
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$27,500
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$27,500
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$25,250
31
 $24,000
September 2025
SuMoTuWeThFrSaWeek
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$24,000
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$24,000
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29
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Clean Fee: 
$1000 per week
Tax: State & Local: 
11.7
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Stunning Luxury Home, Complete Renovation in Main House, Sweet Updated Guest House, Walk to Oak Bluffs Center

Gorgeous Luxury Home, Newly Renovated with Stylish Updates, Walking Distance to Oak Bluffs Center

This stunning bungalow-style home has undergone a complete renovation, blending luxury designer decor with the original...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$7,000 - $9,000
June 2025
SuMoTuWeThFrSaWeek
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 $11,000
July 2025
SuMoTuWeThFrSaWeek
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2
3
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$11,000
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$9,000
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$9,000
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$9,000
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 $15,000
August 2025
SuMoTuWeThFrSaWeek
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$15,000
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$17,000
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$17,000
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$12,000
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$10,000
31
 $7,000
September 2025
SuMoTuWeThFrSaWeek
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$7,000
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$7,000
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$7,000
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$7,000
28
29
30
 
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7
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Hidden Cove, Centrally Located to Beaches and Towns, Association Tennis Courts, A/C, WiFi

Centrally located in the Hidden Cove community of homes on the outskirts of Oak Bluffs. Lovely area to bike, walk, or play tennis at the association courts. 

The main level features an...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,400 - $4,500
June 2025
SuMoTuWeThFrSaWeek
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2
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13
14
15
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20
21
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25
26
27
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29
30
 $4,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,000
6
7
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10
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12
$4,000
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14
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19
$4,200
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21
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25
26
$4,200
27
28
29
30
31
 $4,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,500
3
4
5
6
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9
$4,500
10
11
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13
14
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$4,500
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18
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23
$4,500
24
25
26
27
28
29
30
$3,400
31
 $2,600
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,600
7
8
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10
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13
$2,600
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15
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17
18
19
20
$2,600
21
22
23
24
25
26
27
$2,600
28
29
30
 $2,600
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7

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