Chatham Massachusetts homes for sale starting at Fifty Thousand Dollars

$1,469,000 - Chatham, MA

558 Fox Hill Road Chatham, MA - New co-ownership opportunity: Own one-eighth of this turnkey home, professionally managed by Pacaso. Set on 2.74 acres, Fox Hill offers a private sanctuary with 11,000 square feet of sophisticated coastal luxury. The renovated retreat has stunning views of Crows Pond, Eastward Ho and Pleasant Bay, and a private boat dock. The open, airy living room has a stone fireplace and window seats, and offers vast water views. More views are served up in the chef's kitchen, which features a Wolf gas range, a large island with seating, and doors to an expansive deck overlooking Crows Pond. A cased opening from the kitchen leads to the formal dining room with traditional raised panel walls and a butler's pantry with a wet bar. The three-level home includes a quiet office area for work, a lower-level gym for working out, and an outdoor pool and indoor sauna for pure relaxation. An elevator makes it easy to move between floors. The lower level also has a guest suite with a full kitchen and living room. The home, close to Lighthouse Beach, comes fully furnished and professionally decorated.

$1,400,000 - Chatham, MA

68 Chippingstone Road Chatham, MA - Ideal rental investment property in Riverbay Estates! Enjoy water views and direct access to Pickerel Pond from this 4-bed, 3-bath home perfect for kayaking and paddleboarding. Features include a first-floor primary suite, living and dining areas with pond views, central A/C, gas heat, and an attached two-car garage. The home is generator ready with a panel for the transfer switch already in place. Unfinished attic spaces offer potential for expansion and or extra storage. Just minutes to Chatham's Main Street, beaches, dining, and Pleasant Bay. A great vacation escape, year-round home or rental investment!

$1,400,000 - Chatham, MA

30 Monomessat Way Chatham, MA - A truly exceptional residence, nestled in the picturesque town of Chatham. This impeccably maintained home offers a harmonious blend of elegance and comfort, surrounded by lovely landscaped grounds. The heart of the home is the family room, with cathedral ceiling and a magnificent stone fireplace. A cook's kitchen includes a sub zero refrigerator and breakfast bar. Adjacent to the kitchen is a casual dining area for family meals and the formal living room with a beautiful bow window. The first-floor primary suite serves as a tranquil retreat, featuring an en-suite with a luxurious jet tub and shower. Completing the first floor is a guest bath and laundry. Upstairs are two generous bedrooms with full bath, plus a large bonus room. Whether you're starting your day with coffee on the deck overlooking the beautiful grounds, or unwinding by the fireplace, this home offers the perfect blend of laid-back elegance and charm. Make this exquisite property your own and enjoy all it offers!

$1,399,500 - Chatham, MA

116 Happy Valley Road Chatham, MA - Located off a private way to Ridgevale Beach overlooking a majestic cranberry bog sits this cozy colonial paradise. Built in 2015 by an award winning design/build company is this very private getaway. 1st level open plan features brk bar & dining/living area with views to the bog pond. Door to south facing deck setup for dining & and all day sun. 2 entry kitchen with granite counters & stainless steel appliances. Center cab with storage to kitchen and & a hidden adjustable TV to DR & sectional. Full bath featuring marble top & floor. Entire cottage has solid maple floors, countertops, picture frames & furniture. 2nd level features same custom trims & slightly higher ceilings. Main bedroom with king bed has built in armoires, dressing table & TV cab. Guest room with built in maple bunks & queen bed. Oversized bath in marble has hidden laundry. Separate entry lower level ensuite set up as a study has a queen Murphy bed with full bath allows total privacy for visitors. The entire landscape plan with classic plantings and bluestone steps is sculptured to surround the residence. 2 separate driveways fit 5 cars easily. Easy 10 minute walk to Ridgevale Beach. Furnishings available.

$1,300,000 - Chatham, MA

319 Riverview Drive Chatham, MA - Sited on nearly an acre of land in Riverbay Estates, this spacious 3 bedroom, 3 bath home offers ample privacy and outdoor living space. Built in 1984 with an addition & updates in 2004, the home is designed with flexibility for one floor living with a generous sized first level primary suite with gas fireplace, walk in closet, & outdoor access. The kitchen features abundant cabinet space, a pantry, granite countertops & peninsula, & stainless appliances including a gas range. The adjoining living room has a wood burning fireplace & two sliding doors to a 200 sf screened in porch and expansive deck overlooking a private & sweeping yard suitable for family fun and potential for a pool. There is a formal dining room & mudroom with laundry & an additional full bath to complete the first floor. Above are two generous bedrooms with a shared full bath. The lower level offers 900 sf of finished space with media & an exercise area (not included in the 2202 square feet). Additional highlights include wide plank yellow pine floors in most rooms, an efficient Rinnai tankless water heater, 7 zone well-fed irrigation system, a one car garage with ''barn space'' & expansion opportunities.

$1,295,000 - Chatham, MA

00 Victoria Drive Chatham, MA - Build your dream home on this beautiful lot nestled on a cul de sac in desirable Chatham. Septic design, engineering and wind and energy plan are done. Town water and gas and electric are on the street. Building packages for a Cape and Ranch are available. Capes are approximately 2400 square feet with 2.5 baths and one or two car garage. Could also be customized and price will depend on level of customization. Could also do a plan that one already has. The price listed here is approximate and is to be built. The land can be purchased separately for $399,900, MLS #22402507.

$1,249,000 - Chatham, MA

56 Monomoit Lane Chatham, MA - Tucked away in a serene, private setting, this stylish Cape invites relaxation and coastal living just 1.4 miles from Hardings Beach. Step inside to discover a bright, open floor plan featuring a quartz and stainless kitchen with island, a welcoming living room with cozy fireplace, and a sunlit dining area perfect for gatherings. Unwind in the charming sunroom — a tranquil space bathed in natural light, ideal for afternoon lounging or quiet mornings with coffee. The main level also offers a serene first level bedroom with a bath, while two additional bedrooms and a full bath provide comfortable guest accommodations upstairs. Thoughtful coastal accents, cathedral ceilings, oak floors create a warm, airy ambiance. The finished walk-out lower level offers additional room for relaxing or entertaining, complete with a private outdoor sitting area and outdoor shower. Conveniently located near many of Chatham's favorite restaurants, this home is a perfect year-round haven, summer getaway, or investment property.

$1,114,000 - Chatham, MA

31 Joshua Jethro Road Chatham, MA - Casual living describes this charming 3 Bedroom, 2 Full Bath, 1-car garage under Ranch-style home in lovely Riverbay Estates. Set back from the road on a slight rise, this .47 acre lot abounds with privacy as backyard is completely enclosed by stockade fencing concealed with lovely trees and shrubbery. Relaxing couldn't be easier on the deck right off the kitchen which overlooks a lovely yard ready for your children and pets to play. Adding to its curb appeal the front yard has a split-rail fence by the road with Bayberry bushes planted along its length. Natural gas heat, central A/C and a gas fireplace create a comfortable living experience inside. Adding to the appeal are hardwood floors along with tiled Baths. Completely renovated in 2013, current owner has put in over $120,000 in additional upgrades (see document attached to Listing). Although lightly used as a Seasonal home, owners have lovingly and meticulously maintained their 'Chatham Cape House'. Many Living Room and Bedroom furnishings are available to purchase separately. Chatham is known for sandy beaches & its quaint village of restaurants & boutique shops. Marinas, golf courses & bike paths are nearby. Riverbay ponds are close by or you may prefer the many beaches Chatham has to offer Scenic Lighthouse Beach across from the Coast Guard Station; Jackknife, Cotchpinicut or Scatteree beaches on Pleasant Bay; Oyster Pond Beach with its calm water just steps away from Town; or Hardings, Ridgevale, Cockle Cove, Forest or Pleasant Street beaches on the warm waters of Nantucket Sound. If you prefer fresh water or just a fresh water rinse after a day at a salt water beach, head over to School House Pond. Of course you can rinse off in the outdoor shower at the back of the house. Golf courses, Bike trails, Medical facilities and several churches are nearby.

$995,000 - Chatham, MA

144 Lakeview Avenue Chatham, MA - Three bedroom ranch house in desirable Riverbay Estates. All bedrooms on first floor for easy living. Great neighborhood for swimming, walking, bike riding, kayaking, and fishing at the two private association ponds and the Monomoy River.... Close to Pleasant Bay and School House Pond beaches. Something for everyone in this very private area....Brokers and buyers are encouraged to verify all information herein... See FLOOR PLANS in document section.

$899,900 - Chatham, MA

25 Crosby Lane Chatham, MA - 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.

Chatham, Massachusetts listings for sale

End of list

There were no properties mapped for this search