chatham real estate
An unpretentious approach to buying and selling with a broker who brings 30 years of construction and management experience to the process.
”BY FAR the best experience we’ve ever had. He is unlike anyone in the business. He has broken the mold of what we know to be the real estate brokerage business.” Maura Fitzpatrick . Orleans
“We recently worked with Jon, and it was, BY FAR, the best experience we have ever had. This was our 10th real estate transaction, and we had been completely underwhelmed by the real estate industry to date. It has felt like a very transactional business, lacking the personal touch, honesty and accountability that you would expect for such a personal and emotional experience. Jon changed all that. He is unlike anyone in the business from both a personal and emotional standpoint. On a personal level, there is no outer shell, you know what you are getting from the minute you meet him. Not only does this make for a pleasant experience, but when things get difficult, as they inevitably will during a transaction, knowing who you are dealing with, and that you can trust Jon, is invaluable. On a professional level, he has broken the mold of what we know to be the real estate brokerage business. Take a read through his website, about covering innocuous fees, coordinating cleanouts, taking care of things that he doesn’t want credit for and you only find out about later….it’s all true. If you want an experience where your opinion is important, where you can trust the process and feel really good at the end, you should reach out to Jon. It was such a good experience that I now consider Jon a friend and will go out of my way every chance I get to find him more business.”
Active Chatham Listings
- 35 Pine Tree Road South
- Chatham MA 02659
- $1,250,000
- 3 Beds | 2 Baths | 2,257 SqFt
- 0.23 Acres
- 2550 Main Street South
- Chatham MA 02659
- $3,999,900
- 3 Beds | 4.5 Baths | 4,393 SqFt
- 0.62 Acres
- 73 Main Street UNIT 6
- Chatham MA 02633
- $575,000
- 1 Beds | 1 Baths | 399 SqFt
- 0 Acres
- 41 Court Street North
- Chatham MA 02650
- $2,950,000
- 3 Beds | 2.5 Baths | 3,504 SqFt
- 0.69 Acres
- 101 Morris Island Road
- Chatham MA 02633
- $5,995,000
- 5 Beds | 4.5 Baths | 3,225 SqFt
- 0.48 Acres
- 48 Glover Square
- Chatham MA 02633
- $1,650,000
- 3 Beds | 2 Baths | 2,169 SqFt
- 0.67 Acres
- 6-894 Munson Meeting Way
- Chatham MA 02633
- $699,000
- 2 Beds | 2.5 Baths | 1,773 SqFt
- 0 Acres
- 92 Absegami Run
- Chatham MA 02633
- $3,699,900
- 4 Beds | 3.5 Baths | 3,199 SqFt
- 0.57 Acres
- 137 Shane Drive
- Chatham MA 02633
- $1,495,000
- 3 Beds | 2 Baths | 1,530 SqFt
- 0.25 Acres
- 35 Bobbie's Lane South
- Chatham MA 02659
- $699,900
- 3 Beds | 1 Baths | 1,152 SqFt
- 0.25 Acres
- 85 Cedar Street
- Chatham MA 02633
- $4,700,000
- 5 Beds | 3.5 Baths | 3,080 SqFt
- 1.48 Acres
- 29 Jessies Landing
- Chatham MA 02633
- $3,699,900
- 3 Beds | 4.5 Baths | 4,565 SqFt
- 0.46 Acres
- 33 Crowell Road
- Chatham MA 02633
- $4,499,900
- 3 Beds | 6 Baths | 5,820 SqFt
- 0.44 Acres
- 66 Ethelma Drive
- Chatham MA 02633
- $949,000
- 4 Beds | 1 Baths | 1,547 SqFt
- 0.55 Acres
- 0 Crows Pond Road
- Chatham MA 02633
- $2,499,000
- Beds | Baths | SqFt
- 2.46 Acres
- 50 Eldredge Square S
- Chatham MA 02633
- $1,995,000
- 3 Beds | 2 Baths | 1,488 SqFt
- 0.23 Acres
- 912 Main Street Unit 308
- Chatham MA 02633
- $459,000
- 1 Beds | 2 Baths | 1,284 SqFt
- 0 Acres
- 148 Seapine Road North
- Chatham MA 02650
- $2,250,000
- 3 Beds | 2 Baths | 2,220 SqFt
- 0.59 Acres
- 99 Depot Road APT 23
- Chatham MA 02633
- $645,000
- 2 Beds | 2 Baths | 1,045 SqFt
- 0 Acres
- 60 Harbor Hill Road
- Chatham MA 02633
- $3,600,000
- 4 Beds | 3.5 Baths | 3,978 SqFt
- 0.93 Acres
- 2548 Main Street South
- Chatham MA 02659
- $3,999,900
- 4 Beds | 5.5 Baths | 4,942 SqFt
- 0.85 Acres
- 96 Stage Coach Drive South
- Chatham MA 02659
- $899,000
- 3 Beds | 3 Baths | 1,618 SqFt
- 0.43 Acres
- 260 Tanglewood Drive
- Chatham MA 02633
- $750,000
- 3 Beds | 2 Baths | 1,442 SqFt
- 0.46 Acres
- 7 Squanto Drive
- Chatham MA 02633
- $2,995,000
- 3 Beds | 3.5 Baths | 3,014 SqFt
- 0.69 Acres
Chatham Mass Real Estate
Often penned from a local perspective as a quaint drinking village with a fishing problem, Chatham, situated on the elbow of the Cape, settled in 1664, offers something for everyone. If you can’t find it in one of the locally owned shops dotted up and down what is arguably the most genuine and authentic Main Street amongst each of the lower and outercape towns, Chatham hosts a variety of top-end eateries, Band Concert, as well The Chatham Angler’s of the famed Cape Cod Baseball League.
Chatham real estate no doubt leans toward the top end of the charts in terms of pricing. Although you should never rule out finding that diamond in the rough, price points over $1 million and perhaps $2 million, inventory in the Chatham real estate pool routinely outweighs comparative value options in the sub $1 million range.
One More Chatham fun fact: Replaced by conventional steel and concrete in 2014, The Mitchell River Bridge, an iconic piece of Chatham real estate, would be the last wooden drawbridge in the United States.



