Real Estate Investment Properties for Sale in Chatham, MA

Looking for investment property in Chatham, MA with high ROI ?

Explore a variety of short-term homes & houses in Chatham, MA. Invest wisely with VRBO & Chatham, MA Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Buffington Investment Property for Sale in Chatham, MA

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Showing 60 Buffington Investment Property listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
73 Joshua Jethro Road Chatham, MA PERFECT HOUSE FOR A POOL! Located in Chatham's highly sought after Riverbay Estates commun...	3 beds \| 2 baths \| 2,307 sq.ft.	$1,570,000	Airbnb cash on cash: 2.24% Traditional cash on cash: 1.04% Airbnb Rental Income: $6412 Traditional Rental Income: $3418 Airbnb ROI: 2.24% Traditional ROI: 1.04%
306 Old Queen Anne Road Chatham, MA Cape Cod living made easy in this beautifully updated 4-bedroom, 2-bathroom Cape nestled i...	4 beds \| 2 baths \| 1,680 sq.ft.	$949,000	Airbnb cash on cash: 3.7% Traditional cash on cash: 2.5% Airbnb Rental Income: $5632 Traditional Rental Income: $3441 Airbnb ROI: 3.7% Traditional ROI: 2.5%
97 Round Cove Road Chatham, MA Welcome to 97 Round Cove Road, a charming Post and Beam home nestled in the heart of Chath...	3 beds \| 4 baths \| 2,388 sq.ft.	$1,595,000	Airbnb cash on cash: 2.11% Traditional cash on cash: 1.41% Airbnb Rental Income: $6412 Traditional Rental Income: $4119 Airbnb ROI: 2.11% Traditional ROI: 1.41%
93 Bucks Creek Road Chatham, MA Welcome to 93 Bucks Creek Rd, where luxury meets coastal elegance. This architecturally st...	3 beds \| N/A baths \| 3,544 sq.ft.	$3,200,000	Airbnb cash on cash: 0.5% Traditional cash on cash: -0.22% Airbnb Rental Income: $6412 Traditional Rental Income: $3031 Airbnb ROI: 0.5% Traditional ROI: -0.22%
290 Old Comers Road Chatham, MA ''On Pink Wink Pond'' embodies the essence of Cape Cod in this remarkable estate. A startl...	4 beds \| N/A baths \| 3,603 sq.ft.	$2,750,000	Airbnb cash on cash: 0.47% Traditional cash on cash: 1.43% Airbnb Rental Income: $5632 Traditional Rental Income: $6955 Airbnb ROI: 0.47% Traditional ROI: 1.43%
14 Pond View Lane Chatham, MA Sears Point Development presents another breathtaking home that could be your new year-rou...	4 beds \| 5 baths \| 4,989 sq.ft.	$5,295,000	Airbnb cash on cash: -0.15% Traditional cash on cash: 0.67% Airbnb Rental Income: $5632 Traditional Rental Income: $8510 Airbnb ROI: -0.15% Traditional ROI: 0.67%
93 Orleans Road Chatham, MA Welcome to the meticulous and delightful 93 Orleans Road Chatham. Enter onto the beautiful...	3 beds \| 2 baths \| 1,702 sq.ft.	$1,399,000	Airbnb cash on cash: 2.68% Traditional cash on cash: 1.19% Airbnb Rental Income: $6412 Traditional Rental Income: $3224 Airbnb ROI: 2.68% Traditional ROI: 1.19%
55 Christopher Harding Lane Chatham, MA Step into coastal elegance in this light-filled home, perfectly nestled in a peaceful neig...	3 beds \| N/A baths \| 2,510 sq.ft.	$2,200,000	Airbnb cash on cash: 1.23% Traditional cash on cash: 0.57% Airbnb Rental Income: $6412 Traditional Rental Income: $3808 Airbnb ROI: 1.23% Traditional ROI: 0.57%
6 Stephen Drive Chatham, MA Set in one of West Chatham's most desirable neighborhoods, just minutes from Hardings and ...	4 beds \| N/A baths \| 3,069 sq.ft.	$2,195,000	Airbnb cash on cash: 0.97% Traditional cash on cash: 1.75% Airbnb Rental Income: $5632 Traditional Rental Income: $6099 Airbnb ROI: 0.97% Traditional ROI: 1.75%
409 Main Street Chatham, MA Location-Location-Location-409 Main Street in downtown Chatham offers you this very rare a...	1 beds \| 2 baths \| 1,479 sq.ft.	$1,995,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 0.05% Airbnb Rental Income: $3128 Traditional Rental Income: $2479 Airbnb ROI: 0.02% Traditional ROI: 0.05%
355 Training Field Road Chatham, MA MOTIVATED SELLERS! Just 8/10 of a mile to Jackknife Point Beach, this beautifully appointe...	3 beds \| 4 baths \| 2,225 sq.ft.	$1,475,000	Airbnb cash on cash: 2.34% Traditional cash on cash: 2.08% Airbnb Rental Income: $6412 Traditional Rental Income: $4803 Airbnb ROI: 2.34% Traditional ROI: 2.08%
558 Fox Hill Road Chatham, MA New co-ownership opportunity: Own one-eighth of this turnkey home, professionally managed ...	5 beds \| 8 baths \| 11,000 sq.ft.	$1,469,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 1.26% Airbnb Rental Income: $8269 Traditional Rental Income: $6840 Airbnb ROI: 1.16% Traditional ROI: 1.26%
99 Uncle Alberts Drive Ext Chatham, MA Experience a rare opportunity to own a prime waterfront property in one of Chatham's most ...	2 beds \| N/A baths \| 1,850 sq.ft.	$5,900,000	Airbnb cash on cash: -1.54% Traditional cash on cash: -1.58% Airbnb Rental Income: $4814 Traditional Rental Income: $3622 Airbnb ROI: -1.54% Traditional ROI: -1.58%
346 Morris Island Road Chatham, MA Views, Views, Views!! Sun splashed Stage Harbor waterfront offering and ever-changing vist...	4 beds \| N/A baths \| 2,850 sq.ft.	$4,900,000	Airbnb cash on cash: -0.3% Traditional cash on cash: -0.23% Airbnb Rental Income: $5632 Traditional Rental Income: $4824 Airbnb ROI: -0.3% Traditional ROI: -0.23%
106 Stage Neck Road Chatham, MA Nestled on just over an acre of meticulously landscaped grounds with a private well for ir...	4 beds \| 4 baths \| 3,834 sq.ft.	$2,500,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 0.52% Airbnb Rental Income: $5632 Traditional Rental Income: $4552 Airbnb ROI: 0.5% Traditional ROI: 0.52%
30 Indian Trail Chatham, MA Laissez Faire, designed and built by Polhemus Savery DaSilva in 2012, is a coastal masterp...	3 beds \| 3 baths \| 2,418 sq.ft.	$4,395,000	Airbnb cash on cash: -0.02% Traditional cash on cash: -0.27% Airbnb Rental Income: $6412 Traditional Rental Income: $4113 Airbnb ROI: -0.02% Traditional ROI: -0.27%
45 Meadow View Road S Chatham, MA New construction and a deeded boat slip in the Oyster River Hills private neighborhood mar...	4 beds \| 6 baths \| 4,908 sq.ft.	$4,200,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 0.59% Airbnb Rental Income: $5632 Traditional Rental Income: $6677 Airbnb ROI: 0.03% Traditional ROI: 0.59%
319 Riverview Drive Chatham, MA Sited on nearly an acre of land in Riverbay Estates, this spacious 3 bedroom, 3 bath home ...	3 beds \| 3 baths \| 2,202 sq.ft.	$1,195,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 2.09% Airbnb Rental Income: $6412 Traditional Rental Income: $3846 Airbnb ROI: 3.27% Traditional ROI: 2.09%
116 Happy Valley Road Chatham, MA Located off a private way to Ridgevale Beach overlooking a majestic cranberry bog sits thi...	2 beds \| 3 baths \| 1,861 sq.ft.	$1,399,500	Airbnb cash on cash: 1.62% Traditional cash on cash: 1.06% Airbnb Rental Income: $4814 Traditional Rental Income: $3101 Airbnb ROI: 1.62% Traditional ROI: 1.06%
335 Stage Island Road Chatham, MA Family-friendly home on Chatham's private Stage Island boasts captivating barrier beach an...	4 beds \| N/A baths \| 5,372 sq.ft.	$4,750,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 0.5% Airbnb Rental Income: $5632 Traditional Rental Income: $8209 Airbnb ROI: -0.34% Traditional ROI: 0.5%
36 Moonbeam Lane Chatham, MA This expansive Cape with timeless curb appeal is located in an exclusive Chatham neighborh...	4 beds \| N/A baths \| 4,857 sq.ft.	$3,495,000	Airbnb cash on cash: 0% Traditional cash on cash: 0.25% Airbnb Rental Income: $5632 Traditional Rental Income: $5309 Airbnb ROI: 0% Traditional ROI: 0.25%
98 Horizon Drive Chatham, MA A new construction and a great value in Chatham with deeded rights to Lover's Lake for swi...	3 beds \| 5 baths \| 3,310 sq.ft.	$2,195,000	Airbnb cash on cash: 1.44% Traditional cash on cash: 1.96% Airbnb Rental Income: $6412 Traditional Rental Income: $6212 Airbnb ROI: 1.44% Traditional ROI: 1.96%
13 Captain Knowles Way Chatham, MA Experience the perfect blend of luxury, privacy, and convenience in this exceptional new c...	5 beds \| 7 baths \| 5,700 sq.ft.	$6,995,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 0.32% Airbnb Rental Income: $8269 Traditional Rental Income: $9202 Airbnb ROI: -0.07% Traditional ROI: 0.32%
307 Riverview Drive Chatham, MA Discover luxury and comfort in this stunning Riverbay home nestled with beautiful landscap...	3 beds \| N/A baths \| 2,340 sq.ft.	$1,575,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 1.22% Airbnb Rental Income: $6412 Traditional Rental Income: $3730 Airbnb ROI: 2.2% Traditional ROI: 1.22%
213 Main Street Chatham, MA Location! Location! Nestled In the heart of Chatham historic Old Village district, this 18...	4 beds \| 2 baths \| 1,238 sq.ft.	$2,150,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 0.09% Airbnb Rental Income: $5632 Traditional Rental Income: $3107 Airbnb ROI: 0.79% Traditional ROI: 0.09%
287 Cedar Street Chatham, MA NEW CONSTRUCTION: Welcome to 287 Cedar Street, an exquisite 3 BR, 4.5 Bath, 3,640 sf retre...	3 beds \| N/A baths \| 3,640 sq.ft.	$3,850,000	Airbnb cash on cash: 0.35% Traditional cash on cash: 0.64% Airbnb Rental Income: $6412 Traditional Rental Income: $6157 Airbnb ROI: 0.35% Traditional ROI: 0.64%
292 Stage Harbor Road Chatham, MA Approximately a half mile to either Oyster Pond Beach or Stage Harbor and 3/4 of a mile to...	3 beds \| N/A baths \| 1,834 sq.ft.	$2,150,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 0.91% Airbnb Rental Income: $6412 Traditional Rental Income: $4526 Airbnb ROI: 1.22% Traditional ROI: 0.91%
55 Winterset Drive Chatham, MA Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham'...	4 beds \| N/A baths \| 4,072 sq.ft.	$2,295,000	Airbnb cash on cash: 0.85% Traditional cash on cash: 1.33% Airbnb Rental Income: $5632 Traditional Rental Income: $5532 Airbnb ROI: 0.85% Traditional ROI: 1.33%
92 Barcliff Avenue Chatham, MA Honored with the prestigious 2004 Chatham Preservation Award, this iconic historical resid...	5 beds \| N/A baths \| 2,659 sq.ft.	$3,500,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 0.28% Airbnb Rental Income: $8269 Traditional Rental Income: $4964 Airbnb ROI: 0.81% Traditional ROI: 0.28%
86 Champlain Road Chatham, MA Hidden gem on Chatham's historic Loop with views of Stage Harbor, the Stage Harbor Lightho...	3 beds \| N/A baths \| 4,361 sq.ft.	$3,200,000	Airbnb cash on cash: 0.27% Traditional cash on cash: 0.53% Airbnb Rental Income: $6412 Traditional Rental Income: $5935 Airbnb ROI: 0.27% Traditional ROI: 0.53%
17 Bucks Lane Chatham, MA This Chatham Beach House is calling...hope you answer.... Picture perfect Cape Cod style h...	4 beds \| 4 baths \| 3,030 sq.ft.	$3,795,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 0.21% Airbnb Rental Income: $5632 Traditional Rental Income: $5285 Airbnb ROI: -0.01% Traditional ROI: 0.21%
30 Tisquantum Road Chatham, MA What. A. View! 180 degree panoramic water vistas over The Atlantic Ocean, Chatham Harbor, ...	5 beds \| N/A baths \| 4,305 sq.ft.	$7,999,000	Airbnb cash on cash: -0.31% Traditional cash on cash: -0.31% Airbnb Rental Income: $8269 Traditional Rental Income: $6683 Airbnb ROI: -0.31% Traditional ROI: -0.31%
24 Chickadee Circle Chatham, MA Nature-lovers! A beautifully renovated post 'n beam home perched above the Monomoy River w...	2 beds \| 2 baths \| 1,504 sq.ft.	$1,050,000	Airbnb cash on cash: 2.57% Traditional cash on cash: 1.72% Airbnb Rental Income: $4814 Traditional Rental Income: $2989 Airbnb ROI: 2.57% Traditional ROI: 1.72%
127 Wapoos Trail Chatham, MA Tucked within the exclusive & secluded enclave of Morris Island, this one-of-a-kind water ...	5 beds \| 4 baths \| 4,307 sq.ft.	$8,250,000	Airbnb cash on cash: -0.44% Traditional cash on cash: -0.5% Airbnb Rental Income: $8269 Traditional Rental Income: $6242 Airbnb ROI: -0.44% Traditional ROI: -0.5%
56 Riverview Drive Chatham, MA Located in Chatham's sought after Riverbay Estates, known for its treelined streets and co...	3 beds \| 2 baths \| 1,708 sq.ft.	$1,195,000	Airbnb cash on cash: 3.32% Traditional cash on cash: 1.55% Airbnb Rental Income: $6412 Traditional Rental Income: $3188 Airbnb ROI: 3.32% Traditional ROI: 1.55%
114 Bucks Creek Road Chatham, MA 'Float to the ocean with the tide'' Fish, crab kayak, paddleboard and launch off the priva...	4 beds \| 3 baths \| 2,289 sq.ft.	$1,450,000	Airbnb cash on cash: 2% Traditional cash on cash: 1.64% Airbnb Rental Income: $5632 Traditional Rental Income: $4017 Airbnb ROI: 2% Traditional ROI: 1.64%
101 Morris Island Road Chatham, MA LIGHTHOUSE BEACH - A Nantucket-inspired coastal home designed and built by Polhemus Savery...	5 beds \| N/A baths \| 3,225 sq.ft.	$6,395,000	Airbnb cash on cash: -0.16% Traditional cash on cash: -0.12% Airbnb Rental Income: $8269 Traditional Rental Income: $6901 Airbnb ROI: -0.16% Traditional ROI: -0.12%
24 Hillcrest Road Chatham, MA Set within one of North Chatham's most coveted enclaves-surrounded by multi-million-dollar...	5 beds \| 3 baths \| 3,098 sq.ft.	$1,895,000	Airbnb cash on cash: 2.51% Traditional cash on cash: 1.17% Airbnb Rental Income: $8269 Traditional Rental Income: $4330 Airbnb ROI: 2.51% Traditional ROI: 1.17%
53 Grist Mill Lane Chatham, MA Wake up to captivating and shimmering water views from nearly every room in this stunning ...	5 beds \| 7 baths \| 6,722 sq.ft.	$9,750,000	Airbnb cash on cash: -0.55% Traditional cash on cash: -0.35% Airbnb Rental Income: $8269 Traditional Rental Income: $8464 Airbnb ROI: -0.55% Traditional ROI: -0.35%
200 Hardings Beach Road Chatham, MA Located just a short stroll to Hardings Beach and close to many favorite local restaurants...	4 beds \| 2 baths \| 1,820 sq.ft.	$1,495,000	Airbnb cash on cash: 1.88% Traditional cash on cash: 1.2% Airbnb Rental Income: $5632 Traditional Rental Income: $3563 Airbnb ROI: 1.88% Traditional ROI: 1.2%

Your search for investment property begins and ends here

Buffington Investment Property for Sale in Chatham, MA

73 Joshua Jethro Road

Chatham, MA

3 beds | 2 baths | 2,307 sq.ft.

$1,570,000

Airbnb cash on cash: 2.24%

Traditional cash on cash: 1.04%

Airbnb Rental Income: $6412

Traditional Rental Income: $3418

Airbnb ROI: 2.24%

Traditional ROI: 1.04%

306 Old Queen Anne Road

Chatham, MA

4 beds | 2 baths | 1,680 sq.ft.

$949,000

Airbnb cash on cash: 3.7%

Traditional cash on cash: 2.5%

Airbnb Rental Income: $5632

Traditional Rental Income: $3441

Airbnb ROI: 3.7%

Traditional ROI: 2.5%

97 Round Cove Road

Chatham, MA

3 beds | 4 baths | 2,388 sq.ft.

$1,595,000

Airbnb cash on cash: 2.11%

Traditional cash on cash: 1.41%

Airbnb Rental Income: $6412

Traditional Rental Income: $4119

Airbnb ROI: 2.11%

Traditional ROI: 1.41%

93 Bucks Creek Road

Chatham, MA

3 beds | N/A baths | 3,544 sq.ft.

$3,200,000

Airbnb cash on cash: 0.5%

Traditional cash on cash: -0.22%

Airbnb Rental Income: $6412

Traditional Rental Income: $3031

Airbnb ROI: 0.5%

Traditional ROI: -0.22%

290 Old Comers Road

Chatham, MA

4 beds | N/A baths | 3,603 sq.ft.

$2,750,000

Airbnb cash on cash: 0.47%

Traditional cash on cash: 1.43%

Airbnb Rental Income: $5632

Traditional Rental Income: $6955

Airbnb ROI: 0.47%

Traditional ROI: 1.43%

14 Pond View Lane

Chatham, MA

4 beds | 5 baths | 4,989 sq.ft.

$5,295,000

Airbnb cash on cash: -0.15%

Traditional cash on cash: 0.67%

Airbnb Rental Income: $5632

Traditional Rental Income: $8510

Airbnb ROI: -0.15%

Traditional ROI: 0.67%

93 Orleans Road

Chatham, MA

3 beds | 2 baths | 1,702 sq.ft.

$1,399,000

Airbnb cash on cash: 2.68%

Traditional cash on cash: 1.19%

Airbnb Rental Income: $6412

Traditional Rental Income: $3224

Airbnb ROI: 2.68%

Traditional ROI: 1.19%

55 Christopher Harding Lane

Chatham, MA

3 beds | N/A baths | 2,510 sq.ft.

$2,200,000

Airbnb cash on cash: 1.23%

Traditional cash on cash: 0.57%

Airbnb Rental Income: $6412

Traditional Rental Income: $3808

Airbnb ROI: 1.23%