Chatham Homes $500k - $1M

Dreaming of cool summer breezes and sunshine? Discover homes $500k-$1m in Chatham, a picturesque beachside town on Cape Cod, MA. Whether for a summer getaway or a permanent home, you are sure to find what you've been looking for. Save your favorites when you register with us today, and get notifications when similar properties are posted. Contact us for more information and to set up a showing for any listing below.

25 Crosby Lane Chatham MA 02633

Chatham, MA25 Crosby Lane

Price$899,900

Est. Mortgage: $/month

MLS Number 22500622

  • Residential
  • Bathroom 2
  • Bathrooms Total Decimal 2
  • Bedrooms 2
  • Full Bath 2

TWO HOUSES! Nestled on a quiet road just off Route 28, this unique Chatham property offers a rare opportunity with two separate homes on one lot! The main house features 2 bedrooms, 2 bathrooms, a one-car garage, ready for your cosmetic updates to make it shine. The guest house (ADU) is a 1-bedroom, 1-bathroom space, perfect for rental income, extended family, or a private retreat.Enjoy the best of Cape Cod living with easy access to Chatham's charming downtown, beaches, and dining--all while tucked away in a peaceful setting. Whether you're looking for an investment property, multi-generational living, or a chance to create your dream home, this property is full of potential.

Listed by Amanda Smith of Christie's International Real Estate Atlantic Brokerage

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Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2590 Main Street Chatham MA 02659

South Chatham, MA2590 Main Street

Price$779,900

Est. Mortgage: $/month

MLS Number 22500677

  • Residential
  • Bathroom 3
  • Bathrooms Total Decimal 3
  • Bedrooms 5
  • Full Bath 3

In the heart of South Chatham, just moments from Forest Road Beach, this versatile 5-bedroom, 3-bathroom antique home offers endless possibilities. Built in 1834, yet, designed for dual-unit living, the property is perfect for multi-generational families, rental income, or easily converting into a spacious single-family retreat.Sitting on a 6-bedroom septic system, this home provides potential for future expansion, making it an excellent long-term investment. Each unit features its own living space, kitchen, and private entrances, offering flexibility for a variety of living arrangements or a perfect home occupation location with excellent street visibilty.Enjoy the best of Cape Cod coastal living close (.8 miles) to the ocean beach, easy access to shopping, dining, and all that Chatham has to offer. Whether you're looking for a primary residence, vacation getaway, or income-producing property, this home is a rare opportunity in a highly sought-after location.

Listed by Richard J Waystack of William Raveis Real Estate & Home Services

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$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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82 Diane Drive Chatham MA 02633

Chatham, MA82 Diane Drive

Price$775,000

Est. Mortgage: $/month

MLS Number 22405661

  • Residential
  • Bathroom 1
  • Bathrooms Total Decimal 1
  • Bedrooms 2
  • Full Bath 1

The 4th of July is less than 6 months away! Here is a rare opportunity to be a stone's throw from Ridgevale Beach with private association access via the Buck's Creek Association bridge. This 2-bedroom cape style cottage is ready for rehab, or a total rebuild. It sits on an elevated bluff and is not in the Flood Zone. Abutting conservation land, the site offers plenty of privacy and has great potential. It currently offers seasonal views of Nantucket Sound. A buyer may want to explore options for potential expanded views. Ocean breezes and one of Chatham's most desirable vacation locations await your arrival.

Listed by Doug Grattan of Christie's International Real Estate Atlantic Brokerage

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$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1761 Main Street Chatham MA 02633

Chatham, MA1761 Main Street

Price$740,000

Est. Mortgage: $/month

MLS Number 22500004

  • Residential
  • Bathroom 2
  • Bathrooms Total Decimal 2
  • Bedrooms 3
  • Full Bath 2

Price reduction! Just around the corner from Ridgevale beach in Chatham; lies this terrific opportunity to build a large home and guest house or 2 separate houses on this 1 acre lot that backs up to a cranberry bog. The lot has sewer hook up in front of the house. This lot has potential view of the cranberry bog and is very close to Ridgevale beach. If you are looking to build a large home with a guest house and a pool or 2 houses; this lot has many possibilities; including potential subdivision. Please note the existing house is in dis-repair and needs extensive renovation or to be torn down.

Listed by Kathleen Phelan of Compass Massachusetts,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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19 Stoughton Lane Chatham MA 02633

Chatham, MA19 Stoughton Lane

Price$725,000

Est. Mortgage: $/month

MLS Number 22404019

  • Residential
  • Bathroom 2
  • Bathrooms Total Decimal 2
  • Bedrooms 3
  • Full Bath 2

Here is your chance to own a slice of seaside Chatham! This prime location is only a short walk or .02 miles to stunning Ridgevale Beach on pristine Nantucket Sound. Included in the sale is a passed 3 bedroom Title V septic inspection report and Board of Health letter, ZBA approval to demolish the existing structure and to build a dwelling with a deck via special permit and Conservation approval. Seller has building plans for a 3 bedroom, 2 bath, 1356 SF home. Imagine the possibilities of creating your own home on this rare piece of land in this welcoming, quaint seaside community. Your Beach Retreat at 19 Stoughton Lane awaits your arrival!

Listed by Shane K Masaschi of Kinlin Grover Compass

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$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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broker reciprocity The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Summary or thumbnail real estate listings held by brokerage firms other than Chatelain Real Estate are marked with the BR Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor Chatelain Real Estate shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless.

This site was last updated March 18, 2025 10:21 PM EDT. All properties are subject to prior sale, changes, or withdrawal.

Chatelain Real Estate has chosen to display only certain towns and/or types or styles of properties. This site may not show all listings that are available through the Cape Cod & Islands Multiple Listing Service, Inc.