Chatham, MA Homes

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  /35

  $695,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,296 Sq Ft

  1 Seastrand Way Unit 1, Chatham, MA 02633

  Rare opportunity to own this totally renovated, secluded end unit feels like a 1296 Sq ft ranch home, but no work! This is an immaculate unit with many fine features which make it a pleasure to relax in comfort. A gracious foyer entrance hall leads to a cathedral ceiling living room with floor to ceiling brick gas fireplace. The beautiful hardwood floors lead you to the dining area and oversize

  Phyllis Power Compass

  1 Seastrand Way Unit 1, Chatham, MA 02633
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  /2

  $540,000 Sold Sep 18, 2025

  0 Reynolds Cir Unit 22501745, Chatham, MA 02633

  • Land
  • 1.2 Acres
  • $450,000 per Acre

  Last Sold Summary

  • 2% Below List Price
  • 81 Days On Market

  Last Listing Agent Derek Greene The Greene Realty Group

  0 Reynolds Cir Unit 22501745, Chatham, MA 02633
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  /55

  Est $2,798,680 Not Listed For Sale

  15 Edgewater Dr, Chatham, MA 02633

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft
  • Built 1960

  15 Edgewater Dr, Chatham, MA 02633

  Last Sold Summary

  • 7% Above List Price
  • $1,243/SF
  • 119 Days On Market

  Last Sold Price $2,610,000

  Last Listing Agent Shane Masaschi Compass
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  /10

  $4,499,900 New Construction

  • 3 Beds
  • 7 Baths
  • 5,820 Sq Ft

  33 Crowell Rd, Chatham, MA 02633

  A distinguished new residence by Eastward Companies, this exceptional home seamlessly blends timeless architecture with modern luxury, all within walking distance to Chatham Village, Oyster Pond, and renowned dining. Thoughtfully designed and impeccably crafted, the home spans over 5,800 square feet across three finished levels. The main level offers an elegant yet inviting floor plan, featuring

  Doug Grattan Christie's International Real Estate Atlantic Brokerage

  33 Crowell Rd, Chatham, MA 02633
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  /53

  $1,495,000 Sold Dec 15, 2025

  291 Ridgevale Rd, Chatham, MA 02633

  • 3 Beds
  • 1.5 Baths
  • 1,424 Sq Ft
  • Built 1950

  Last Sold Summary

  • $1,050/SF
  • 8 Days On Market

  Current Estimated Value $1,461,584

  Last Listing Agent Jan Nowak Craigville Realty Co

  291 Ridgevale Rd, Chatham, MA 02633
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  /54

  Est $3,742,519 Not Listed For Sale

  173 Kendrick Rd, North Chatham, MA 02650

  • 6 Beds
  • 4.5 Baths
  • 4,106 Sq Ft
  • Built 2000

  173 Kendrick Rd, North Chatham, MA 02650

  Last Sold Summary

  • 1% Above List Price
  • $900/SF
  • 174 Days On Market

  Last Sold Price $3,695,000

  Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC
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  /27

  $1,650,000

  • 1 Bath
  • 2,586 Sq Ft

  231 Crowell Rd, Chatham, MA 2633

  Zoned Gb3, this great commercial, multi-use property consists of 2 buildings. The first building built in1995 has 948 sf with a multi-use space, an office and full bath. There is a Viessman heating and hot water system and the full basement is waiting to be finished. The second building has1,638 sf built in 2003 with 2 bays and a carport. One bay has a gas heater and the second floor is ready to

  Judith Smith John C. Ricotta & Associates, Inc.

  231 Crowell Rd, Chatham, MA 2633
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  /20

  $1,975,000 Sold Oct 08, 2025

  20 Hardings Beach Rd, Chatham, MA 02633

  • 4 Beds
  • 3.5 Baths
  • 2,770 Sq Ft
  • Built 1970

  Last Sold Summary

  • 1% Below List Price
  • $713/SF
  • 31 Days On Market

  Current Estimated Value $1,959,478

  Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

  20 Hardings Beach Rd, Chatham, MA 02633
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  /30

  Est $2,460,095 Not Listed For Sale

  72 Old Field Bend, North Chatham, MA 02650

  • 4 Beds
  • 4.5 Baths
  • 3,776 Sq Ft
  • Built 2001

  72 Old Field Bend, North Chatham, MA 02650

  Last Sold Summary

  • 12% Above List Price
  • $582/SF
  • 1 Day On Market

  Last Sold Price $2,195,800

  Last Listing Agent Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties
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  /23

  $1,995,000

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft

  50 Eldredge Square S, Chatham, MA 02633

  Ideally situated just moments from Chatham's Village boutiques and restaurants, this exceptional three bedroom,two bath residence captures the essence of Chatham coastal living. Privately set on a private dead-end street, the property offers tranquility and also convenience in one of Chatham's most desirable settings. Thoughtfully designed for effortless single-level living, the main floor

  Chris Rhinesmith Compass Massachusetts, LLC

  50 Eldredge Square S, Chatham, MA 02633
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  /32

  $765,000 Sold Dec 18, 2025

  47 Cranberry Way, South Chatham, MA 2659

  • 2 Beds
  • 2 Baths
  • 868 Sq Ft
  • Built 1941

  Last Sold Summary

  • 4% Below List Price
  • $881/SF
  • 11 Days On Market

  Current Estimated Value $764,444

  Last Listing Agent William Raye Gibson Sotheby's International Realty

  47 Cranberry Way, South Chatham, MA 2659
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  /54

  Est $1,801,769 Not Listed For Sale

  52 Wentworth Ln, North Chatham, MA 02650

  • 5 Beds
  • 2.5 Baths
  • 2,352 Sq Ft
  • Built 1972

  52 Wentworth Ln, North Chatham, MA 02650

  Last Sold Summary

  • 3% Above List Price
  • $746/SF
  • 3 Days On Market

  Last Sold Price $1,754,000

  Last Listing Agent The Bohman Hartung Group Gibson Sotheby's International Realty
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  /33

  $4,500,000

  • 4 Beds
  • 3.5 Baths
  • 2,850 Sq Ft

  346 Morris Island Rd, Chatham, MA 02633

  Panoramic Stage Harbor views are the centerpiece of this exceptional Morris Island waterfront setting. The property offers four bedrooms and 3.5 baths, each room oriented to the scenery beyond. The residence pairs a classic seaside character with an elevated aesthetic. The main living level is bright and welcoming with a high-end kitchen, generous living room and dining area overlooking the water

  Chris Rhinesmith Compass Massachusetts, LLC

  346 Morris Island Rd, Chatham, MA 02633
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  /58

  $1,309,000 Sold Jun 20, 2025

  144 Countryside Dr, Chatham, MA 02633

  • 2 Beds
  • 2.5 Baths
  • 2,590 Sq Ft
  • Built 2004

  Last Sold Summary

  • 1% Above List Price
  • $505/SF
  • 1 Day On Market

  Current Estimated Value $1,346,706

  Last Listing Agent Maureen Green Kinlin Grover Compass

  144 Countryside Dr, Chatham, MA 02633
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  /31

  Est $2,190,621 Not Listed For Sale

  37 Bellamy Ln, North Chatham, MA 02650

  • 5 Beds
  • 3 Baths
  • 3,401 Sq Ft
  • Built 1988

  37 Bellamy Ln, North Chatham, MA 02650

  Last Sold Summary

  • 37% Above List Price
  • $470/SF
  • 13 Days On Market

  Last Sold Price $1,600,000

  Last Listing Agent David Doherty Compass
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  /37

  $1,425,000

  • 2 Beds
  • 3 Baths
  • 2,212 Sq Ft

  1114 Orleans Rd Unit 2, North Chatham, MA 02650

  Part of the historic Christopher Ryder House, this elegant two-bedroom, three bath condominium blends one floor living with timeless architectural charm. The residence offers beautifully proportioned rooms, high ceilings, large sun-filled windows, and warm wood floors throughout. A gracious foyer opens to a grand living room with gas fireplace that flows seamlessly into the dining room and

  Chris Rhinesmith Compass Massachusetts, LLC

  1114 Orleans Rd Unit 2, North Chatham, MA 02650
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  /55

  $650,000 Sold Jul 31, 2025

  1996 Main St, Chatham, MA 02633

  • 3 Beds
  • 2 Baths
  • 1,813 Sq Ft
  • Built 1955

  Last Sold Summary

  • 10% Below List Price
  • $359/SF
  • 93 Days On Market

  Current Estimated Value $753,797

  Last Listing Agent Shane Masaschi Compass

  1996 Main St, Chatham, MA 02633
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  /47

  Est $2,227,930 Not Listed For Sale

  75 Whidah Rd, North Chatham, MA 02650

  • 4 Beds
  • 2.5 Baths
  • 2,524 Sq Ft
  • Built 1969

  75 Whidah Rd, North Chatham, MA 02650

  Last Sold Summary

  • 9% Above List Price
  • $812/SF
  • 4 Days On Market

  Last Sold Price $2,050,000

  Last Listing Agent Tim Bailey John C Ricotta & Assoc.
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  /60

  $1,795,000

  • 3 Beds
  • 3.5 Baths
  • 2,256 Sq Ft

  70 Old Queen Anne Rd, Chatham, MA 02633

  Don't miss this charming 3-bedroom Cape with classic New England appeal, nicely sited on over 1/2 acre that's perfect for a pool! A welcoming farmer's porch greets your entry into this finely-crafted home that features an abundance of sunlight, built-ins and special touches throughout. The flexible layout lends to one-floor living if desired; with a lovely primary suite, bright granite &

  Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

  70 Old Queen Anne Rd, Chatham, MA 02633
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  /44

  $1,227,000 Sold Jul 25, 2025

  56 Monomoit Ln, Chatham, MA 02633

  • 3 Beds
  • 2 Baths
  • 1,639 Sq Ft
  • Built 1998

  Last Sold Summary

  • 12% Below List Price
  • $749/SF
  • 28 Days On Market

  Current Estimated Value $1,241,141

  Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

  56 Monomoit Ln, Chatham, MA 02633
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  /42

  Est $1,281,689 Not Listed For Sale

  20 Spring Hill Rd, North Chatham, MA 02650

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 1994

  20 Spring Hill Rd, North Chatham, MA 02650

  Last Sold Summary

  • 5% Above List Price
  • $766/SF
  • 26 Days On Market

  Last Sold Price $1,225,000

  Last Listing Agent Julie Chapin William Raveis Chatham
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  /25

  $450,000

  • 1 Bed
  • 1 Bath
  • 578 Sq Ft

  425 Main St Unit D, Chatham, MA 02633

  Nestled above Bumbula ''It's All About Me,'' Unit D at 425 Main Street offers an exceptional blend of privacy, comfort, and in-town convenience. This updated 1-bedroom, 1-bath residence is one of only two homes on the second floor, accessed by a discreet private entrance that enhances its quiet, retreat-like feel. Inside, an open-concept layout is filled with natural light and features recent

  Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

  425 Main St Unit D, Chatham, MA 02633
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  /42

  $11,500,000 Sold Jul 29, 2025

  23 Oyster Pond Ln, Chatham, MA 02633

  • 5 Beds
  • 5.5 Baths
  • 5,308 Sq Ft
  • Built 1963

  Last Sold Summary

  • 8% Below List Price
  • $2,167/SF
  • 9 Days On Market

  Current Estimated Value $6,558,260

  Last Listing Agent Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

  23 Oyster Pond Ln, Chatham, MA 02633
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  /35

  Est $1,458,962 Not Listed For Sale

  101 Old Mail Rd, North Chatham, MA 02650

  • 3 Beds
  • 1.5 Baths
  • 1,511 Sq Ft
  • Built 1940

  101 Old Mail Rd, North Chatham, MA 02650

  Last Sold Summary

  • 9% Below List Price
  • $1,058/SF
  • 7 Days On Market

  Last Sold Price $1,599,000

  Last Listing Agent Jessica King Compass Massachusetts, LLC
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  /2

  $3,999,900 New Construction

  • 4 Beds
  • 5.5 Baths
  • 4,942 Sq Ft

  2548 Main St, South Chatham, MA 2659

  One of two new Eastward Company homes being constructed in this private enclave in Chatham. It offers the opportunity to select your own finishes at this stage with occupancy for next Summer 2026. The builder is committed to providing the utmost quality and proven floor plans which appeal to the most discerning buyers. Incorporating expansive open living space you will enjoy entertaining family

  Ward Brown William Raveis Real Estate & Home Services

  2548 Main St, South Chatham, MA 2659
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  /47

  $1,065,000 Sold May 09, 2025

  718 Riverview Dr, Chatham, MA 02633

  • 2 Beds
  • 2.5 Baths
  • 2,292 Sq Ft
  • Built 1971

  Last Sold Summary

  • 3% Below List Price
  • $465/SF
  • 16 Days On Market

  Current Estimated Value $1,102,646

  Last Listing Agent Tim Bailey John C Ricotta & Assoc.

  718 Riverview Dr, Chatham, MA 02633
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  /18

  Est $335,152 Not Listed For Sale

  197 Stony Hill Rd Unit C, Chatham, MA 02633

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Built 1995

  197 Stony Hill Rd Unit C, Chatham, MA 02633

  Last Sold Summary

  • 12% Above List Price
  • $500/SF
  • 185 Days On Market

  Last Sold Price $300,000

  Last Listing Agent Caroline McAdams Covell Realty Inc
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  /23

  $550,000 Pending

  • 4 Beds
  • 1 Bath
  • 1,428 Sq Ft

  28 Charles St, South Chatham, MA 02659

  Set on a private road in South Chatham, 28 Charles St is a 4 bedroom, 1 bath, 1,428 square foot Cape Cod home on a private lot. The roof is about 10 years old and the property has oil heat, while the walk out basement offers strong potential for future finished space. Enjoy easy access to outdoor fun with the bike path just 0.2 miles away and Forest Beach, a sandy Nantucket Sound beach, only 1

  Shane Masaschi Compass

  28 Charles St, South Chatham, MA 02659
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  /23

  $2,700,000 Sold Jul 24, 2025

  30 Mill Hill Ln, Chatham, MA 02633

  • 7 Beds
  • 3 Baths
  • 2,460 Sq Ft
  • Built 1840

  Last Sold Summary

  • 17% Below List Price
  • $1,098/SF
  • 238 Days On Market

  Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

  30 Mill Hill Ln, Chatham, MA 02633
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  /53

  Est $1,096,337 Not Listed For Sale

  43 Misty Meadow Ln Unit B, North Chatham, MA 02650

  • 2 Beds
  • 3.5 Baths
  • 2,546 Sq Ft
  • Built 2005

  43 Misty Meadow Ln Unit B, North Chatham, MA 02650

  Last Sold Summary

  • 7% Below List Price
  • $463/SF
  • 10 Days On Market

  Last Sold Price $1,180,000

  Last Listing Agent Kristen Savely Compass Massachusetts, LLC
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  /7

  $250,000 Pending

  • Land
  • 0.72 Acre
  • $347,222 per Acre

  0 George Ryder Rd Unit 73104629, Chatham, MA 02633

  Amazing opportunity to build your dream home in Chatham on this .72-acre, panhandle, private residential lot. Build a 3-bedroom home connected to town sewer, 4-bedroom with approval. (buyer's & buyer's agents verify with Board of Health). The water, gas, electric, cable and sewer are on George Ryder Road. This property is convenient to shopping, seven restaurants, the bike path, a medical office,

  Shane Masaschi Compass

  0 George Ryder Rd Unit 73104629, Chatham, MA 02633
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  /42

  $9,650,000 Sold Nov 06, 2025

  53 Gristmill Ln, Chatham, MA 02633

  • 5 Beds
  • 8 Baths
  • 4,970 Sq Ft
  • Built 1989

  Last Sold Summary

  • 1% Below List Price
  • $1,942/SF
  • 30 Days On Market

  Current Estimated Value $9,521,132

  Last Listing Agent Sharon Mabile Berkshire Hathaway HomeServices Robert Paul Properties

  53 Gristmill Ln, Chatham, MA 02633
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  /29

  Est $1,044,533 Not Listed For Sale

  39 Misty Meadow Ln, North Chatham, MA 02650

  • 2 Beds
  • 2.5 Baths
  • 1,812 Sq Ft
  • Built 2005

  39 Misty Meadow Ln, North Chatham, MA 02650

  Last Sold Summary

  • 4% Above List Price
  • $555/SF
  • 10 Days On Market

  Last Sold Price $1,005,000

  Last Listing Agent Team Guthrie - Mabile Berkshire Hathaway HomeServices Robert Paul Properties
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  /36

  $849,000

  • 3 Beds
  • 2 Baths
  • 1,425 Sq Ft

  49 Duck Marsh Ln, Chatham, MA 02633

  Located in Chatham's Countryside neighborhood, this three-bedroom, two-bath cape-style ranch gets plenty of natural light and features a primary suite with a private bath and good closet space. Two additional bedrooms can be used for family, guests, or a home office. The living room has a brick fireplace. A one-car garage and large unfinished basement sits below the home, and the property sits on

  Tim Bailey John C Ricotta & Assoc.

  49 Duck Marsh Ln, Chatham, MA 02633
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  /41

  $1,785,000 Sold Nov 24, 2025

  24 Shattuck Place, Chatham, MA 02633

  • 4 Beds
  • 2.5 Baths
  • 1,514 Sq Ft
  • Built 1920

  Last Sold Summary

  • 1% Below List Price
  • $1,179/SF
  • 7 Days On Market

  Current Estimated Value $1,775,344

  Last Listing Agent Charles King Real Broker MA, LLC

  24 Shattuck Place, Chatham, MA 02633
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  /27

  Est $1,040,513 Not Listed For Sale

  37 Misty Meadow Ln Unit B, North Chatham, MA 02650

  • 2 Beds
  • 2.5 Baths
  • 1,906 Sq Ft
  • Built 2005

  37 Misty Meadow Ln Unit B, North Chatham, MA 02650

  Last Sold Summary

  • 7% Above List Price
  • $512/SF
  • 55 Days On Market

  Last Sold Price $975,000

  Last Listing Agent Tia Lilly Property Cape Cod
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  /45

  $2,100,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,510 Sq Ft

  55 Christopher Harding Ln, Chatham, MA 02633

  Step into coastal elegance in this light-filled home, perfectly nestled in a peaceful neighborhood with deeded access to Oyster Pond. Savor your morning coffee in the sun-drenched four-season room, and take in sunset with your favorite beverage on the second-floor deck, where tranquil views set the scene. Inside, you'll find three spacious bedrooms and 2.5 beautifully designed bathrooms offering

  Diane Donahue Gibson Sotheby's International Realty

  55 Christopher Harding Ln, Chatham, MA 02633
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  /44

  $1,150,000 Sold Apr 18, 2025

  15 Wood Valley Rd, Chatham, MA 02633

  • 4 Beds
  • 3 Baths
  • 2,881 Sq Ft
  • Built 1969

  Last Sold Summary

  • $399/SF
  • 2 Days On Market

  Current Estimated Value $1,323,973

  Last Listing Agent The Bohman Hartung Group Gibson Sotheby's International Realty

  15 Wood Valley Rd, Chatham, MA 02633
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  /25

  Est $1,174,275 Not Listed For Sale

  61 Bishops Terrace, Chatham, MA 02633

  • 3 Beds
  • 2.5 Baths
  • 1,608 Sq Ft
  • Built 1966

  61 Bishops Terrace, Chatham, MA 02633

  Last Sold Summary

  • 59% Above List Price
  • $460/SF
  • 31 Days On Market

  Last Sold Price $740,000

  Last Listing Agent Shane Masaschi Kinlin Grover Compass
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  /44

  $5,495,000

  • 2 Beds
  • 2.5 Baths
  • 1,850 Sq Ft

  99 Uncle Alberts Drive Extension, Chatham, MA 2633

  Experience a rare opportunity to own a prime waterfront property in one of Chatham's most sought-after locations. Set on 1.44 acres, this beautifully crafted 2-bedroom, 2.5 bath home offers 1,850 sq ft of refined living space w/commanding panoramic views stretching across Oyster Pond, Oyster River & to Nantucket Sound. This exceptional offering includes a conceptual site plan & video for a future

  Shane Masaschi Compass

  99 Uncle Alberts Drive Extension, Chatham, MA 2633

Showing Results 121 - 160, Page 4 of 18