Jennifer Matthews
Luxury Real Estate Advisor
Design Savvy, Wall Street Smart
A recognized industry leader and former home design magazine Publisher, Jennifer spent more than twenty-five years leading sales teams - selling to and negotiating with the world's top luxury brands working on titles like Elle Décor, House & Garden, Western Interiors, Luxe Interiors + Design, and Cottages & Gardens (CTC&G, NYC&G, HC&G, SFC&G). Buyers and sellers benefit from her sales and sharp negotiating skills, which started early on Wall Street and further developed running magazine brands.
Prior to launching her real estate business, Jennifer was VP of Sales at Sotheby’s NYC in e-commerce luxury home where she mastered the art of client service and discretion working with luxury brands, dealers, interior designers, and their clients. She joined William Pitt Sotheby’s International Realty knowing the power of the global brand first hand.
A Fairfield County resident for twenty six years, Jennifer and her husband moved to Rowayton, CT from San Francisco in 1999 and raised their son Andrew - along with a golden named Bentley, and two rescued black labs, Jack and Winston.
She is a member of the Decorator’s Club of New York, HBRA (Home Builders & Remodelers Association) Fairfield County, NAR (National Association of Realtors), DBOR (Darien Board of Realtors), and supports local organizations like the Rowayton Arts Center, Farm Creek Preserve/Norwalk Land Trust, Bayley Beach, Rowayton Civic Association, Rowayton Historical Society, Open Door Shelter, and The Glass House.
Fun Facts: Jennifer is a history, art, and classical architecture fan. She grew up riding horses on vists to her grandparents farm and learned English riding at New Canaan Mounted Troop. Jennifer loves the coastal New England lifestyle - her husband's family has a noted history in Newport of America's Cup sailing contributions and accomplishments and are descendants of the Weed family in Darien. A special life moment to date was being a “greeting family” for the arrival of her Majesty Queen Elizabeth II and Prince Philip in Bermuda at Tucker’s Point in 2008.
A recognized industry leader and former home design magazine Publisher, Jennifer spent more than twenty-five years leading sales teams - selling to and negotiating with the world's top luxury brands working on titles like Elle Décor, House & Garden, Western Interiors, Luxe Interiors + Design, and Cottages & Gardens (CTC&G, NYC&G, HC&G, SFC&G). Buyers and sellers benefit from her sales and sharp negotiating skills, which started early on Wall Street and further developed running magazine brands.
Prior to launching her real estate business, Jennifer was VP of Sales at Sotheby’s NYC in e-commerce luxury home where she mastered the art of client service and discretion working with luxury brands, dealers, interior designers, and their clients. She joined William Pitt Sotheby’s International Realty knowing the power of the global brand first hand.
A Fairfield County resident for twenty six years, Jennifer and her husband moved to Rowayton, CT from San Francisco in 1999 and raised their son Andrew - along with a golden named Bentley, and two rescued black labs, Jack and Winston.
She is a member of the Decorator’s Club of New York, HBRA (Home Builders & Remodelers Association) Fairfield County, NAR (National Association of Realtors), DBOR (Darien Board of Realtors), and supports local organizations like the Rowayton Arts Center, Farm Creek Preserve/Norwalk Land Trust, Bayley Beach, Rowayton Civic Association, Rowayton Historical Society, Open Door Shelter, and The Glass House.
Fun Facts: Jennifer is a history, art, and classical architecture fan. She grew up riding horses on vists to her grandparents farm and learned English riding at New Canaan Mounted Troop. Jennifer loves the coastal New England lifestyle - her husband's family has a noted history in Newport of America's Cup sailing contributions and accomplishments and are descendants of the Weed family in Darien. A special life moment to date was being a “greeting family” for the arrival of her Majesty Queen Elizabeth II and Prince Philip in Bermuda at Tucker’s Point in 2008.
A recognized industry leader and former home design magazine Publisher, Jennifer spent more than twenty-five years leading sales teams - selling to and negotiating with the world's top luxury brands working on titles like Elle Décor, House & Garden, Western Interiors, Luxe Interiors + Design, and Cottages & Gardens (CTC&G, NYC&G, HC&G, SFC&G). Buyers and sellers benefit from her sales and sharp negotiating skills, which started early on Wall Street and further developed running magazine brands.
Prior to launching her real estate business, Jennifer was VP of Sales at Sotheby’s NYC in e-commerce luxury home where she mastered the art of client service and discretion working with luxury brands, dealers, interior designers, and their clients. She joined William Pitt Sotheby’s International Realty knowing the power of the global brand first hand.
A Fairfield County resident for twenty six years, Jennifer and her husband moved to Rowayton, CT from San Francisco in 1999 and raised their son Andrew - along with a golden named Bentley, and two rescued black labs, Jack and Winston.
She is a member of the Decorator’s Club of New York, HBRA (Home Builders & Remodelers Association) Fairfield County, NAR (National Association of Realtors), DBOR (Darien Board of Realtors), and supports local organizations like the Rowayton Arts Center, Farm Creek Preserve/Norwalk Land Trust, Bayley Beach, Rowayton Civic Association, Rowayton Historical Society, Open Door Shelter, and The Glass House.
Fun Facts: Jennifer is a history, art, and classical architecture fan. She grew up riding horses on vists to her grandparents farm and learned English riding at New Canaan Mounted Troop. Jennifer loves the coastal New England lifestyle - her husband's family has a noted history in Newport of America's Cup sailing contributions and accomplishments and are descendants of the Weed family in Darien. A special life moment to date was being a “greeting family” for the arrival of her Majesty Queen Elizabeth II and Prince Philip in Bermuda at Tucker’s Point in 2008.
Read Less
Testimonials
Jennifer relentlessly marketed our property in a very slow season and got a challenging deal structure across the finish line. Many thanks!!
Jennifer was great - above and way beyond expectations. I had the misfortune of breaking my leg just prior to putting the house on the market, and she handled all of the logistics of final preparation and staging, not to mention the usual broker responsibilities. In an unusually volatile market, we worked closely on pricing and presentation, and ended up closing with an amount well above what the comparison homes went for. Very happy with the whole process!
It was great working with you on the purchase of a Connecticut Property. I am grateful for all of your help in making this a smooth transaction. Thank you for your partnership. I look forward to working together in the future. Thank you!!
Professional advice and research service with ultimate customer service attention to detail from your very pleasant agent, Jennifer Matthews. A+ all around!
What a pleasure it was to work with you...I know you will soar as you successfully transition from publishing to real estate. Let's work together again!
Jennifer is full of energy and positivity. Colleagues benefit greatly from her sales experience, leadership skills, professionalism, work ethic and industry connectedness. Jennifer’s motivation is infectious. She exhibits perseverance, adaptability, and a desire to continuously build on her skillset. She is a pleasure to work with.
Jennifer is smart, driven and effective. She is one of the hardest working people I know and she gets results. In addition to being a hard-worker she is also one of the kindest, most up-beat people I have ever met. She is one of those rare colleagues you enjoy working with because they are both fun and personable and get the job done. She is someone who I hope to continue have to have in both my personal & professional orbit throughout my career.
Jennifer is an extraordinary colleague and salesperson, always willing to go the extra mile, creative in her pitches and thorough in her follow-ups. She was directly responsible for the growth in our sales, working tirelessly to bring on new clients and enhance relationships with existing ones. She has been able to pivot with the business and in the face of the pandemic, showing her adaptability. Jennifer is also the loveliest and kindest person to work with!
I have had the honor to report directly to Jennifer Matthews, and I have never had a more collaborative or more supportive manager. Jennifer truly looks out for her team. In addition to being proactive and responsive, Jennifer is a strategic thinker who always manages to push the business forward.
Our client and his daughters are forever grateful as are we for your kindness. Thank you...you have made such a difference! Warm Regards,
Thank you so much for letting us into this beautiful home. We can't wait for the years to come filled with cooking, swimming, beach days, and movies!
Jennifer is one of the most proactive enthusiastic sales people we have worked with! She was always creative and out of the box and continually coming up with ideas and initiatives.
My Sales
18 Janes Lane
Stamford, CT 06903 | Fairfield County $1,250,000| 5 Beds | 4/1 Baths | 6,459 Sqft | 2.12 Acres |
This exceptional home is located on a quiet street of North Stamford within a mile of the Merritt Parkway, surrounded by two parks and two schools. This beautiful Contemporary...
- 5
- bed
- 4/1
- bath
- 6,459
- sqft
9 Patton Drive
Darien, CT 06820 | Fairfield County $915,000| 3 Beds | 2 Baths | 1,450 Sqft | 0.15 Acres |
Welcome to this beautifully updated sun-filled Cape Cod-style home, exuding a warm and inviting urban cottage vibe, nestled in one of Darien's most desirable neighborhoods. Perfectly...
- 3
- bed
- 2
- bath
- 1,450
- sqft
62 Raymond Street
Darien, CT 06820 | Fairfield County $865,000| 3 Beds | 2 Baths | 1,880 Sqft | 0.23 Acres |
Move right into this stylish updated Darien Dutch colonial on the border of Darien and Rowayton - enjoy close proximity to the water and quaint seaside village of Rowayton - the...
- 3
- bed
- 2
- bath
- 1,880
- sqft
37 South Street
Roxbury , CT 07683 $12,500| 3 Beds | 3/1 Baths | 1,700 Sqft | 3.42 Acres |
- 3
- bed
- 3/1
- bath
- 1,700
- sqft
88 Five Mile River Road
Darien, CT 06820 | Fairfield County $11,250/mo| 4 Beds | 3 Baths | 2,756 Sqft | 0.45 Acres |
Live on one of Darien's most beautiful waterfront streets and enjoy living across the street from the Long Island Sound! This charming coastal colonial has been completely renovated...
- 4
- bed
- 3
- bath
- 2,756
- sqft
88 Five Mile River Road
Darien, CT 06820 | Fairfield County $11,250/mo| 4 Beds | 3 Baths | 2,756 Sqft | 0.45 Acres |
This is a rare opportunity to live on one of Darien's most beautiful waterfront streets. Move right in this summer and enjoy living across the street from the Long Island Sound!...
- 4
- bed
- 3
- bath
- 2,756
- sqft
88 Five Mile River Road
Darien, CT 06820 | Fairfield County $10,500/mo| 4 Beds | 3 Baths | 2,756 Sqft | 0.45 Acres |
The Connecticut coastline awaits you- an incredible and rare opportunity to live in Darien on the Five Mile River Road across the street from the water! This charming coastal colonial...
- 4
- bed
- 3
- bath
- 2,756
- sqft








