orleans 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.”
Orleans Real Estate
Active Listings
- 64 Pershing Lane
- Orleans MA 02653
- $6,250,000
- 5 Beds | 6.5 Baths | 5,800 SqFt
- 1 Acres
- 18 Cole Place
- Orleans MA 02653
- $699,000
- 3 Beds | 2 Baths | 1,381 SqFt
- 0 Acres
- 216 Main Street
- Orleans MA 02653
- $1,900,000
- 7 Beds | 8 Baths | 3,234 SqFt
- 2 Acres
- 7 Lockwood Lane
- Orleans MA 02653
- $999,990
- Beds | Baths | SqFt
- 1 Acres
- 18 West Road # 307
- Orleans MA 02653
- $545,000
- 2 Beds | 2 Baths | 1,623 SqFt
- 0 Acres
- 4 Monomoy Lane
- Orleans MA 02653
- $2,995,000
- 4 Beds | 3.5 Baths | 3,680 SqFt
- 1 Acres
- 18 West Road # 315
- Orleans MA 02653
- $417,000
- 2 Beds | 2 Baths | 1,200 SqFt
- 0 Acres
- 15 Dale Ann Drive
- Orleans MA 02653
- $1,450,000
- 4 Beds | 2 Baths | 1,694 SqFt
- 1 Acres
- 181 Rock Harbor Road
- Orleans MA 02653
- $1,250,000
- 2 Beds | 3.5 Baths | 1,888 SqFt
- 1 Acres
- 42 Old Colony Way APT 28
- Orleans MA 02653
- $289,000
- 1 Beds | 1 Baths | 868 SqFt
- 0 Acres
- 507 S Road Orleans
- Orleans MA 02653
- $1,150,000
- 3 Beds | 2 Baths | 1,436 SqFt
- 1 Acres
- 36 Old Colony Way # 3022
- Orleans MA 02653
- $424,900
- 2 Beds | 2 Baths | 1,040 SqFt
- 0 Acres
- 12 Phoebes Close
- Orleans MA 02653
- $1,499,000
- 4 Beds | 3.5 Baths | 3,431 SqFt
- 1 Acres
- 63 kescayogansett Road
- Orleans MA 02653
- $4,799,999
- 5 Beds | 7 Baths | 5,700 SqFt
- 1 Acres
- 8 Monomoy Lane
- Orleans MA 02653
- $3,595,000
- 4 Beds | 3.5 Baths | 4,250 SqFt
- 1 Acres
- 6 Monomoy Lane
- Orleans MA 02653
- $3,295,000
- 4 Beds | 3.5 Baths | 3,680 SqFt
- 1 Acres
- 42 Old Colony Way APT 30
- Orleans MA 02653
- $299,000
- 1 Beds | 1 Baths | 868 SqFt
- 13 Acres
- 42 Old Colony Way APT 14
- Orleans MA 02653
- $379,900
- 2 Beds | 2 Baths | 1,040 SqFt
- 0 Acres
- 32 Locust Road
- Orleans MA 02653
- $579,000
- Beds | Baths | SqFt
- 4 Acres
- 34 Ridgewood Road
- Orleans MA 02653
- $1,050,000
- 4 Beds | 2.5 Baths | 1,825 SqFt
- 1 Acres
- 188 Rock Harbor Road
- Orleans MA 02653
- $1,549,000
- 3 Beds | 3 Baths | 2,110 SqFt
- 1 Acres
- 44 Tonset Road
- Orleans MA 02653
- $3,999,999
- 4 Beds | 6 Baths | 5,170 SqFt
- 2 Acres
- 95 S Road Orleans
- Orleans MA 02653
- $799,000
- 2 Beds | 1 Baths | 1,144 SqFt
- 1 Acres
- 20 Namskaket Road
- Orleans MA 02653
- $799,000
- 3 Beds | 1.5 Baths | 1,403 SqFt
- 1 Acres
Orleans Real Estate
Situated between Brewster and Eastham, Orleans was settled in 1693 and today is perhaps best described as a hybrid of Chatham and Eastham where an active Main Street is tempered by a wealth of walking and biking trails and quiet neighborhoods. Orleans sits 60’ above sea level and boasts having been shelled by a German submarine during World War I. Today, one of Orleans’ gentler and no doubt entertaining highlights include hosting the Orleans Firebirds of the Cape Cod Baseball League and the charter fleet of Rock Harbor.
Orleans real estate continues to evolve as value picks have slowly diminished, and pricing is driven by demand. In turn, while Orleans real estate has a ways to go in terms of becoming a top-heavy luxury market such as Chatham on the other side of the elbow, the trending inventory is not as friendly toward entry level buyers such as Eastham and Brewster offerings yet nevertheless, carving out a piece of the Cape in Orleans will not disappoint.
One More Orleans fun fact: A small skirmish on a prime piece of Orleans real estate, at what is now Rock Harbor, between British marines and a handful of Orleans townies resulted in an Orleans victory. The Battle of Rock Harbor is known to be one of the last battles of the war.




