Jay Contessa

Jay Contessa

Licensed Real Estate Salesperson

Ridgefield Brokerage

470 Main Street
Ridgefield, CT 06877
  • Born In:
    Ridgefield, Ct
  • Live In:
    Redding, CT
  • Favorite Movie:
    The Godfather
  • Inspiration:
    Inches make Champions-Vince Lombardi

Delivering concierge level service to every client every day.

I am a third generation Ridgefield native currently living in Redding for over 25 years. I bring decades of local expertise on our awarded winning school systems and the distinct characteristics that make our communities so special. Our towns are graced with an abundance of scenic charm and family businesses with long held traditions of generosity and support. Fairfield County’s vast architecture of homes, proximity to NYC, the Vermont mountains, and to the shoreline, makes our communities the perfect choice to raise a family or for a weekend getaway.

I bring a strong proven track record of negotiation skills, marketing, financing and customer service from my prior successful years in corporate leadership. In addition, I have personal experience in home building and complex renovations including residential and commercial properties. As a realtor, my role will be to facilitate and educate my clients to make the best decisions in what could be a complicated process of buying and selling homes.

Today, you need a broker that knows the community's and has the professional resources and marketing tools to get the job done. I look forward to making that happen.

Delivering concierge level service to every client every day.

I am a third generation Ridgefield native currently living in Redding for over 25 years. I bring decades of local expertise on our awarded winning school systems and the distinct characteristics that make our communities so special. Our towns are graced with an abundance of scenic charm and family businesses with long held traditions of generosity and support. Fairfield County’s vast architecture of homes, proximity to NYC, the Vermont mountains, and to the shoreline, makes our communities the perfect choice to raise a family or for a weekend getaway.

I bring a strong proven track record of negotiation skills, marketing, financing and customer service from my prior successful years in corporate leadership. In addition, I have personal experience in home building and complex renovations including residential and commercial properties. As a realtor, my role will be to facilitate and educate my clients to make the best decisions in what could be a complicated process of buying and selling homes.

Today, you need a broker that knows the community's and has the professional resources and marketing tools to get the job done. I look forward to making that happen.

Delivering concierge level service to every client every day.

I am a third generation Ridgefield native currently living in Redding for over 25 years. I bring decades of local expertise on our awarded winning school systems and the distinct characteristics that make our communities so special. Our towns are graced with an abundance of scenic charm and family businesses with long held traditions of generosity and support. Fairfield County’s vast architecture of homes, proximity to NYC, the Vermont mountains, and to the shoreline, makes our communities the perfect choice to raise a family or for a weekend getaway.

I bring a strong proven track record of negotiation skills, marketing, financing and customer service from my prior successful years in corporate leadership. In addition, I have personal experience in home building and complex renovations including residential and commercial properties. As a realtor, my role will be to facilitate and educate my clients to make the best decisions in what could be a complicated process of buying and selling homes.

Today, you need a broker that knows the community's and has the professional resources and marketing tools to get the job done. I look forward to making that happen.

Read Less

Read MoreRead Less
  • Awards
    • Gold Award Winner

Testimonials

Excellent work

Dan Gimmel

Very helpful.

Kleber Siguenza

Jay Contessa was outstanding through all phases of our home selling process. His coaching, advise and guidance was always spot on and the results proved that. He and the full team at William Pitt / Sotheby's were truly a pleasure to work with.

Michael Tusa

Jay Contessa has been the ultimate professional from start to finish and far exceeded our expectations for working with a realtor. His knowledge and expertise made him invaluable to the whole process. From market timing, to staging advice, to negotiating the best deal for us, Jay really helped alleviate much of the stress. We highly recommend Jay Contessa to anyone in the Ridgefield area. Pat and Mike Tusa

Patricia Tusa

Jay Contessa was a fantastic realtor! He went over and above to support us in our process of buying a home, and made sure the home was ready for us to move in. It is a property that needed a bit of work beforehand, and Jay handled the tasks with true expertise, always making sure we were well informed. We felt comfortable the entire time. Thank you Jay for making our first home buying experience so seamless and special :)

Jessi Brattengeier

Highly recommend! Our realtor, Jay Contessa, went above and beyond to help us find a home. He not only worked with us to find a home, but helped us connect with many in the community for the services we wanted to employ on our new home. Jay is fantastic and has become such a huge part of our buying experience. Meanwhile, my wife and I felt that Sotheby’s had our back and made the entire process smooth and low stress. This included not only the house, but the bank, lawyer, and the many inspectors needed during the buying process.

Adoniram Weimer

We couldn't have been luckier when we were paired with Jay Contessa through his agency. Jay listened to all of our wants and needs and shared his thorough knowledge of the local communities and real estate market while showing us properties. He ensured that the purchase of our property went smoothly with the seller. Thank you, Jay!

David and Amy

Jay is a true professional in his field. He constantly kept us in the loop with updates and feedback. He always went above and beyond in both buying and selling of our homes. Always responded in a very timely manner to any of our needs. Jay is both personable and professional in every way.

Gloria Ogiela

Wonderful experience from start to finish! Thank you!

Linda Kallner

We are so very happy that, now that the time has come to downsize, we entrusted the sale of our favorite home to Nick Davis (mgr) and Jay Contessa (our agent) at Sotheby's. The market information we received was spot on, and the preparation leading up to the listing of our home was insightful and thorough. Above all, we appreciate the personal interest, and the consideration of our feelings and needs through the entire process. Best real estate experience ever. Thank you!

Rodrigo Escobar

Jay was the best real estate agent anyone could ask for. To say he went above and beyond is an understatement. He, of course, knew the market in our search radius very well and showed us any home that might be of interest while understanding the comps and relative pricing/value to advise us appropriately. But beyond that, he also scoped out open house volume, found and coordinated vendors for us, and really anything we needed (or didn’t even know we needed). Jay showed us what is possible and blew away all expectations we had for a real estate agent!

Micah Spellman

Jay Contessa was exceptional and went above and beyond for myself and my family. He is honestly the epitome of what one would hope a real estate agent would be. We are beyond grateful for him and all he did for us.

Leslie Lewis

In my opinion, Jay Contessa is a ten-star real estate agent and a person of absolute integrity. My experience with Jay was easy because he attended to every detail personally and took responsibility for on time performance throughout the process. My purchase was via a new LLC formation which is more involved than a usual purchase. Jay made sure all the banking, legal, inspection and accounting processes were knitted together as necessary, making the transaction as stress free as possible on my behalf. Jay is hard working, honest person who services his clients' interests. I whole heartedly recommend him to whomever is looking to buy or sell real estate.

Leslie A Lewis III

Jay is awesome!! Jay is an agent who truly cares about his clients--not just a commission! He acts as your advocate, not one who is out there to collect a payday. He helped me with prompt research and strategy sessions for both renting a property and buying properties. A big thing that Jay does is finds the right home at the right price. Not just a home at whatever price. Those who I've referred him too were also delighted with his custom care and attention to detail in finding them their new homes!

Sam Williams

Jay was the best real estate broker we have ever worked with ( and Have made 2 other house purchases in my life) . He went above and beyond for us and honestly gave great advice as well as being a great resource for services in the area. he was available 24/7 and was knowledgeable and professional. I would refer Jay to anyone I know looking for a house in Connecticut.

Chris Hoffman

My husband and I are so thankful to have purchased our first home through Jay and William Pitt! Jay was so helpful in helping us learn about the different towns in the area and really helped us to understand where we were in relation to town landmarks and our jobs at each home we looked at. Searching for a home during the pandemic was not easy by any means, yet we still felt each offer we placed was fair thanks to Jay's guidance. Jay always knew all the houses on the market in our price range and tailored our search as much as he could given the circumstances! It was reassuring to tour houses with Jay because of his expertise - for example, he would always check the equipment in the basement, the heat, hot water, etc. to note the quality of them and if they'd likely need to be replaced soon. It was fantastic to work with a realtor like Jay who was quick to pick up on our personalities in addition to our housing "wants"! I'd absolutely recommend him to friends and family looking to purchase a home in the Ridgefield area!

Lori , Buyer

My Sales

13 Mark Twain Lane $2,000,000 link

13 Mark Twain Lane

Redding, CT 06896 | Fairfield County
$2,000,000
4 Beds 3/1 Baths 5,108 Sqft 3.2 Acres

Nestled on 3.2 quiet, wooded acres, this impeccable 4 bedroom, 3.5 bath Colonial was once a part of the famed Mark Twain property. Situated on an idyllic country lane in Redding...

4
bed
3/1
bath
5,108
sqft
276 North Avenue $1,875,000 link

276 North Avenue

Westport, CT 06880 | Fairfield County
$1,875,000
5 Beds 4 Baths 3,972 Sqft 1.2 Acres

On the market for the first time in 50 years, this is a rare opportunity to buy one of the original Coley family houses. Originally built in 1830, 276 North Ave is a stunning antique...

5
bed
4
bath
3,972
sqft
54 Ketcham Road $1,800,000 link

54 Ketcham Road

Ridgefield, CT 06877 | Fairfield County
$1,800,000
3 Beds 3/1 Baths 3,241 Sqft 12.96 Acres

Spectacular country estate, owned by the notable Landsberger family for almost 70 years, set back on 12.96 stunning acres in premier southwest location, with opportunity to...

3
bed
3/1
bath
3,241
sqft
165 Linden Tree Road $1,745,000 link

165 Linden Tree Road

Wilton, CT 06897 | Fairfield County
$1,745,000
7 Beds 5/2 Baths 6,418 Sqft 3.03 Acres

What better quality could you ask for in a home than one built by an established builder for himself and his family? Located on popular Wilton street, walking distance to scenic...

7
bed
5/2
bath
6,418
sqft
76 Canterbury Lane $1,700,000 link

76 Canterbury Lane

Ridgefield, CT 06877 | Fairfield County
$1,700,000
4 Beds 3/2 Baths 5,564 Sqft 2.06 Acres

Welcome Home to 76 Canterbury Lane in Ridgefield, CT! This breathtaking Colonial with charming front porch overlooking the rolling front grounds is impeccably maintained and quite...

4
bed
3/2
bath
5,564
sqft
120 Pine Mountain Road $1,595,000 link

120 Pine Mountain Road

Ridgefield, CT 06877 | Fairfield County
$1,595,000
1 Beds 1/1 Baths 1,613 Sqft 18.08 Acres

Twin Brooks - 18 acre private compound with expansive scenic pond, dock, bridge, extensive stone walls and professional landscaping including walking trails, gardens, plus magical...

1
bed
1/1
bath
1,613
sqft
21 Deer Spring Road $1,465,000 link

21 Deer Spring Road

Redding, CT 06896 | Fairfield County
$1,465,000
5 Beds 4/1 Baths 4,187 Sqft 10.65 Acres

Situated on over 10 Acres, this one-of-a-kind horse property is in the sought after community of Redding with award winning schools. This property features a four-stall horse stable...

5
bed
4/1
bath
4,187
sqft
18 Great Pasture Road $1,455,000 link

18 Great Pasture Road

Redding, CT 06896 | Fairfield County
$1,455,000
5 Beds 2/2 Baths 3,492 Sqft 2.91 Acres

A majestic Colonial home with unmatched street presence stands on nearly 3 gorgeous acres of land. This picturesque property is located on a sought-after scenic road. Close to...

5
bed
2/2
bath
3,492
sqft
44 Still Road $1,350,000 link

44 Still Road

Ridgefield, CT 06877 | Fairfield County
$1,350,000
4 Beds 3/1 Baths 5,128 Sqft 1.76 Acres

Originally built by Ridgefield's Pelham Country Homes, this newly renovated property is the epitome of style and grace.This fantastic property is located on a private drive...

4
bed
3/1
bath
5,128
sqft
22 Ashbee Lane $1,330,000 link

22 Ashbee Lane

Ridgefield, CT 06877 | Fairfield County
$1,330,000
5 Beds 3/1 Baths 5,706 Sqft 2.14 Acres

Step into the timeless elegance of this beautiful historic home, where old-world charm seamlessly blends with modern amenities. The gorgeous original wide board flooring will captivate...

5
bed
3/1
bath
5,706
sqft
12 Mulberry Street $1,175,000 link

12 Mulberry Street

Ridgefield, CT 06877 | Fairfield County
$1,175,000
4 Beds 2/1 Baths 3,334 Sqft 1.23 Acres

Formula for fine living: location, curb appeal, and style. This expansive Colonial Salt Box is perfectly nestled on the end of the cul-de-sac with lovely pond views. Welcome to...

4
bed
2/1
bath
3,334
sqft
30 Wood Road $1,160,000 link

30 Wood Road

Redding, CT 06896 | Fairfield County
$1,160,000
4 Beds 2/1 Baths 4,672 Sqft 2.1 Acres

Pride of ownership combined with rich features from outdoor enjoyment and proximity to key local amenities make this a "must-see." Located in the highly desirable Sunset...

4
bed
2/1
bath
4,672
sqft