Contact
Address
103 Mason St
Greenwich, CT 06830
Jeff Jackson doesn't just sell homes, he engineers outcomes. With over 30 years operating at the highest levels of Fairfield County real estate and more than $2 billion in closed sales, Jeff has built a practice defined by precision, discretion, and a track record that consistently places him among the top 10 brokers in Greenwich.
Where most agents count transactions, Jeff counts relationships. His client base, including executives relocating from New York, local families upgrading or repositioning, and downsizers seeking their final home of consequence, trusts him not just to find the right property, but to navigate every complexity the market presents. Off-market access, nuanced valuation, and a deep command of the data that actually drives pricing decisions aren’t talking points. They’re the foundation of how he works.
That analytical edge was forged early. Jeff studied economics at Manhattanville College and spent his formative summers working for a master builder of custom homes in the Hamptons, an experience that set him on a path to becoming one of the earliest practitioners of data-driven valuation in residential real estate. When Barbara Corcoran launched the Corcoran Report, she didn't look to Wall Street for her data partner. She called Jeff. That collaboration lasted decades and cemented his reputation well beyond Connecticut's borders.
Year after year, Jeff closes in excess of $100 million in sales, not by volume-chasing, but by being exactly the kind of advisor serious buyers and sellers want in their corner. He combines the market intelligence and buyer network of a top-producing firm with something rarer in this business: genuine, hands-on attention from the person whose name is on the door.
Jeff has called Greenwich home for more than 20 years. He knows this market not as an outsider with a license, but as a resident, a neighbor, and a professional whose reputation is built one transaction at a time, in a town where everyone knows everyone, and nothing travels faster than the truth.
Jeff is a true pro. Knows the space incredibly well, is straightforward and not "sales-y," and gets great results for his clients. I recommend him wholeheartedly.
Jeff is a true pro. Knows the space incredibly well, is straightforward and not "sales-y," and gets great results for his clients. I recommend him wholeheartedly.
Consummate professional. A+. I would highly recommend Jeff to anyone looking to buy or sell a house in the tri-state area. He has worked for decades as a broker, as a developer, and as an appraiser. The breadth of Jeff's experience gives him a leg up on market activity and valuation. He showed us several properties that had not yet been listed, which is incredibly valuable in our tight and competitive local market. Most importantly, Jeff at all times conducted himself with great integrity and was a true advisor to us throughout the buying process.
Consummate professional. A+. I would highly recommend Jeff to anyone looking to buy or sell a house in the tri-state area. He has worked for decades as a broker, as a developer, and as an appraiser. The breadth of Jeff's experience gives him a leg up on market activity and valuation. He showed us several properties that had not yet been listed, which is incredibly valuable in our tight and competitive local market. Most importantly, Jeff at all times conducted himself with great integrity and was a true advisor to us throughout the buying process.
Jeff acted as the agent on both the sale of our existing home and the purchase of our new home, both in Greenwich, CT. Jeff did an outstanding job on both transactions. Jeff was critical at every stage of the process, from pricing our existing home, preparing it for sale, timing the presentation to market, marketing the property, finding the right buyer, and negotiating the sale. He was just as critical in the purchase of our new home: helping us find the perfect home, formulate our bid, negotiate the terms of the purchase, and ultimately get to closing. Jeff's knowledge of the local market is unmatched, and he is particularly skillful at valuing properties. Jeff was first class from start to finish. While we have no intention of moving any time soon, Jeff will certainly be our first call if we do.
Jeff acted as the agent on both the sale of our existing home and the purchase of our new home, both in Greenwich, CT. Jeff did an outstanding job on both transactions. Jeff was critical at every stage of the process, from pricing our existing home, preparing it for sale, timing the presentation to market, marketing the property, finding the right buyer, and negotiating the sale. He was just as critical in the purchase of our new home: helping us find the perfect home, formulate our bid, negotiate the terms of the purchase, and ultimately get to closing. Jeff's knowledge of the local market is unmatched, and he is particularly skillful at valuing properties. Jeff was first class from start to finish. While we have no intention of moving any time soon, Jeff will certainly be our first call if we do.
A real pro! Always available, quick to understand our needs, and stayed involved through closing. Also has a great assistant who was always responsive. Would recommend him for any transaction.
A real pro! Always available, quick to understand our needs, and stayed involved through closing. Also has a great assistant who was always responsive. Would recommend him for any transaction.
My husband and I had a very positive experience with Jeff and will use his services again when we buy or sell. We have referred Jeff to our friends who are looking to move to Greenwich—it doesn't get better than that!
My husband and I had a very positive experience with Jeff and will use his services again when we buy or sell. We have referred Jeff to our friends who are looking to move to Greenwich—it doesn't get better than that!
I've done two transactions with Jeff, and he is the most plugged-in and knowledgeable agent I've come across in Fairfield County. He knows more about the Greenwich market than anyone I've come across. He's amazingly responsive and insightful. In particular, if you are looking to buy, you must speak with Jeff.
I've done two transactions with Jeff, and he is the most plugged-in and knowledgeable agent I've come across in Fairfield County. He knows more about the Greenwich market than anyone I've come across. He's amazingly responsive and insightful. In particular, if you are looking to buy, you must speak with Jeff.
Browse My
$18,250,000
11 French Road, Greenwich,, CT 06831
$16,500,000
382 North St Street, Greenwich, CT 06830
Sold on July 24, 2026
$14,600,000
30 Meadowcroft Lane, Greenwich, CT 06830
Sold on August 9, 2024
$10,650,000
1093 Pequot Avenue, Fairfield, Connecticut 06890
Sold on October 17, 2025
$9,750,000
35 Club Road, Greenwich, CT 06878
$9,350,000
20 Ann Street, Old Greenwich, CT 06870
$9,350,000
20 Carriglea Drive, Riverside, CT 06878
$8,595,000
17 Wooddale Road, Greenwich, CT 06830
Sold on November 25, 2025
$8,150,000
21 Binney Lane, Old Greenwich, CT 06870
Sold on April 17, 2026
$8,000,000
928 West Road, New Canaan, CT 06840
$7,375,000
18 Meadowcroft Lane, Greenwich, CT 06830
Sold on July 16, 2025
$7,350,000
8 Lindsay Drive, Greenwich, CT 06830
$7,195,000
26 Stoney Wylde Lane, Greenwich, CT 06830
Sold on February 27, 2026
$7,150,000
35 Sterling Road, Greenwich, CT 06831
Sold on July 1, 2025
$6,525,000
18 Shoal Point Lane, Riverside, CT 06878
Sold on August 19, 2026
$5,950,000
164 Stanwich Road, Greenwich, CT 06830
Sold on May 19, 2026
$5,650,000
129 Doubling Road, Greenwich, CT 06830
$5,250,000
28 Verona Drive, Riverside, CT 06878
$4,995,000
15 Tomahawk Lane, Greenwich, CT 06830
Sold on October 1, 2026
$4,650,000
17 Brookside Park, Greenwich, CT 06831
Sold on February 27, 2026
$4,650,000
17 Will Merry Lane, Greenwich, CT 06831
Sold on August 15, 2024
$4,500,000
25 Point Road, Norwalk, CT 06854
Sold on October 15, 2024
$4,300,000
24 Rocky Point Road, Greenwich, CT 06870
Sold on August 4, 2026
$4,260,000
33 Cliffdale Road, Greenwich, CT 06831
Sold on March 31, 2025
$4,204,500
45 Wesskum Wood Road, Riverside, CT 06878
Sold on December 23, 2024
$3,950,000
3 Bennett Street, Old Greenwich, CT 06870
Sold on January 7, 2026
$3,831,000
145 Shore Road, Old Greenwich, CT 06870
Sold on June 29, 2026
$3,525,000
12 Ricki Beth Lane, Greenwich, CT 06870
Sold on July 24, 2024
$3,453,000
20 Knoll Street, Greenwich, Connecticut 06878
$3,375,000
24 Park Avenue, Old Greenwich, CT 06870
Sold on September 26, 2024
$3,305,000
23 Connecticut Avenue, Greenwich, CT 06830
Sold on April 10, 2026
$3,007,000
341 Sound Beach Avenue, Old Greenwich, CT 06870
Sold on March 2, 2026
$2,995,000
424 Taconic Road, Stamford, CT 06904
Sold on September 23, 2026
$2,850,000
214 Good Hill Road, Weston, CT 06883
Sold on August 28, 2024
$2,805,000
719 Ponus Ridge, New Canaan, CT 06840
Sold on August 26, 2026
$2,700,000
33 Mead Avenue, Greenwich, CT 06807
Sold on November 7, 2025
$2,575,000
2 Midbrook Lane, Old Greenwich, CT 06870
Sold on October 31, 2024
$2,550,000
6 Miltiades Avenue, Riverside, CT 06878
Sold on July 2, 2025
$2,465,000
6 Prescott Lane, Greenwich, CT 06830
Sold on June 29, 2026
$2,120,000
81 Pinewood Road, Stamford, CT 06903
Sold on June 5, 2025
$2,100,000
16 Dandy Drive, Greenwich, CT 06807
Leased on August 19, 2024
$22,500/mo
17 Rustic View Road, Greenwich, Connecticut 06830
Leased on July 17, 2025
$5,200/mo
43 Connecticut Avenue, 1, Greenwich, CT 06830
Find Your Next Dream Home
He provides strategic guidance to buyers and sellers throughout Fairfield County. Combining deep market intelligence, expert negotiation, and a data-driven approach, he delivers discreet, personalized representation and exceptional results in every transaction.