Lindsey Rosen

Lindsey Rosen

Licensed Real Estate Salesperson

Fairfield-Southport Brokerage

132 Old Post Road
Southport, CT 06890
  • Born In:
    Westchester, NY
  • Live In:
    Fairfield, CT
  • Interests:
    Paddle boarding, Yoga, Reading, Animal Rescue, Cooking, Traveling
  • Can’t Live Without:
    Books and Dogs!

In recent years, technology has disrupted almost every industry, and Real Estate is no exception. As such, choosing an agent who is at the forefront of technology gives you a definitive advantage. No one understands that better than Lindsey. Prior to launching her real estate career, Lindsey was a digital ad executive for almost 2 decades, starting her career working with tech clients such as HP and Microsoft, and moving on to work with iconic brands such as National Geographic, The North Face, and Cartier.

In an ever changing market hiring a full-time professional is even more critical to making your home sale or purchase as smooth as possible. As a full-time REALTOR, Lindsey combines her tech expertise with her desire to help people. Her integrity, attention to detail, and compassionate nature allow her to provide each client with the personalized attention they deserve. Whether they are buying, selling, or renting, Lindsey cares deeply about what is best for her clients and will guide them through the process, making it as straightforward and stress-free as possible.

Having lived on both coasts, Lindsey has built real estate relationships within some of the country's premier vacation destinations such as San Francisco, Lake Tahoe, Utah, New York, and Connecticut. She currently resides in Fairfield with her fabulous rescue dog Opie. 

Awards and Designations:

- Member of the National Association of Realtors (NAR)

- Member of the Connecticut Association of Realtors (CAR)

- Member of the Fairfield Board of Realtors (GFBOR)

- Serving on the Board of Directors for the Greater Fairfield Board of Realtors as Director 2023, 2024

 

Top Producer:

- Bronze Star award winner Southport Brokerage 2020

- Silver Star Award Winner Southport Brokerage 2021 

- Gold Star Award Winner Southport Brokerage 2022

- Gold Star Award Winner Southport Brokerage 2023

- Gold Star Award Winner Southport Brokerage 2024

- #1 in Units Southport Brokerage 2022

- #1 in Units Southport Brokerage 2023

-# 1 in Rental Units 2024 

#1 in Rental Units first half 2025

In recent years, technology has disrupted almost every industry, and Real Estate is no exception. As such, choosing an agent who is at the forefront of technology gives you a definitive advantage. No one understands that better than Lindsey. Prior to launching her real estate career, Lindsey was a digital ad executive for almost 2 decades, starting her career working with tech clients such as HP and Microsoft, and moving on to work with iconic brands such as National Geographic, The North Face, and Cartier.

In an ever changing market hiring a full-time professional is even more critical to making your home sale or purchase as smooth as possible. As a full-time REALTOR, Lindsey combines her tech expertise with her desire to help people. Her integrity, attention to detail, and compassionate nature allow her to provide each client with the personalized attention they deserve. Whether they are buying, selling, or renting, Lindsey cares deeply about what is best for her clients and will guide them through the process, making it as straightforward and stress-free as possible.

Having lived on both coasts, Lindsey has built real estate relationships within some of the country's premier vacation destinations such as San Francisco, Lake Tahoe, Utah, New York, and Connecticut. She currently resides in Fairfield with her fabulous rescue dog Opie. 

Awards and Designations:

- Member of the National Association of Realtors (NAR)

- Member of the Connecticut Association of Realtors (CAR)

- Member of the Fairfield Board of Realtors (GFBOR)

- Serving on the Board of Directors for the Greater Fairfield Board of Realtors as Director 2023, 2024

 

Top Producer:

- Bronze Star award winner Southport Brokerage 2020

- Silver Star Award Winner Southport Brokerage 2021 

- Gold Star Award Winner Southport Brokerage 2022

- Gold Star Award Winner Southport Brokerage 2023

- Gold Star Award Winner Southport Brokerage 2024

- #1 in Units Southport Brokerage 2022

- #1 in Units Southport Brokerage 2023

-# 1 in Rental Units 2024 

#1 in Rental Units first half 2025

In recent years, technology has disrupted almost every industry, and Real Estate is no exception. As such, choosing an agent who is at the forefront of technology gives you a definitive advantage. No one understands that better than Lindsey. Prior to launching her real estate career, Lindsey was a digital ad executive for almost 2 decades, starting her career working with tech clients such as HP and Microsoft, and moving on to work with iconic brands such as National Geographic, The North Face, and Cartier.

In an ever changing market hiring a full-time professional is even more critical to making your home sale or purchase as smooth as possible. As a full-time REALTOR, Lindsey combines her tech expertise with her desire to help people. Her integrity, attention to detail, and compassionate nature allow her to provide each client with the personalized attention they deserve. Whether they are buying, selling, or renting, Lindsey cares deeply about what is best for her clients and will guide them through the process, making it as straightforward and stress-free as possible.

Having lived on both coasts, Lindsey has built real estate relationships within some of the country's premier vacation destinations such as San Francisco, Lake Tahoe, Utah, New York, and Connecticut. She currently resides in Fairfield with her fabulous rescue dog Opie. 

Awards and Designations:

- Member of the National Association of Realtors (NAR)

- Member of the Connecticut Association of Realtors (CAR)

- Member of the Fairfield Board of Realtors (GFBOR)

- Serving on the Board of Directors for the Greater Fairfield Board of Realtors as Director 2023, 2024

 

Top Producer:

- Bronze Star award winner Southport Brokerage 2020

- Silver Star Award Winner Southport Brokerage 2021 

- Gold Star Award Winner Southport Brokerage 2022

- Gold Star Award Winner Southport Brokerage 2023

- Gold Star Award Winner Southport Brokerage 2024

- #1 in Units Southport Brokerage 2022

- #1 in Units Southport Brokerage 2023

-# 1 in Rental Units 2024 

#1 in Rental Units first half 2025

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  • Agent Designations
    • Certified Relocation Specialist
    • Seller Representative Specialist
    • Certified Buyer Representative
    • Waterfront Property Specialist
  • Awards
    • Gold Star Award Winner Southport Brokerage 2024
    • Gold Star Award Winner Southport Brokerage 2023
    • Gold Star Award Winner Southport Brokerage 2022
    • Silver Star Award Winner Southport Brokerage 2021
    • Bronze Star award winner Southport Brokerage 2020
    • Rookie of the year award winner Southport Brokerage 2019
    • #1 in Units Southport Brokerage 2022
    • #2 in Units Southport Brokerage 2023
  • Specialities
    • Corporate Relocation
    • Off Market Sales
    • Investment Properties
    • First Time Home Buying

Testimonials

Lindsey was the absolute greatest!!! She was honest, supportive, incredibly helpful, and an all around joy to work with. I recommend her with my fullest heart. Selling a home is a hard thing, and she made it about as easy as it can get. Thank you again, Lindsey!!!!

Lisa Ann Goldsmith

Lindsey went above and beyond to help us find a rental home that met all of our needs in such a short period of time! She was so responsive, answered all our questions and would get us in to see listings we were interested so quickly!

Alexa and John Siano

Lindsey Rosen and her colleague were exceptional. The communication was always timely and Lindsey went above and beyond as an agent. There were time when brokers/realtors were difficult to work with/not responding and Lindsey went above and beyond to make sure I was able to check out home of interest when obstacles arose. Further, Lindsey would go beyond to make sure I knew my rights and all information necessary prior to signing any lease. Without her exceptional work I would not have been able to find somewhere to live in a timely manner that met all of my needs including parking, commute, and washer/dryer. Even when Lindsey was away for travel she placed me in contact with her colleague and continued to communicate with me while she was away. Her commitment to her clients places her above other professionals. She truly cares for her clients and makes sure they have everything that they need during what can be a stressful process. Lindsey helped to remove some of the duress by being on time, communicating clearly, and sharing any details regarding my applications in a timely manner. I truly felt led in this process without much work on my end as a client. Anyone willing to go above and beyond in the manner Lindsey has is deserving of recognition for her hard work and dedication. I will and continue to recommend Lindsey to others and look forward to working with her in the future when I am considering a home purchase.

Morinade Stevenson

Because we have put our total trust in Lindsey Rosen, we will continue to recommend William Pitt Sotheby's to friends and colleagues.

Cordova and Cronin

Lindsey Rosen was an absolute pleasure to work with. Personable, efficient, accommodating and responsive to every concern and question I had. Her recommendations were on point too and helped my loan progress faster and closing happen sooner than later. I would highly recommend her!

Kathleen Walsh

I had a fantastic experience working with WP/Sotheby's. Lindsey Rosen is a patient, attentive and skilled realtor. I felt my transaction was seamless and customized to my needs. Thank you so much.

Antonio Reis and Christopher Scovell

Lindsey, was great and made the process go much easier. I hope to use her when I am ready to purchase a home after renting.

Edgar Moore

We really enjoyed working with Lindsey! She was a true professional and guided us through each step of the process, offering her perspective and recommendations based on her years of experience and success. We highly recommend her!

Steve and Lissette Nelson

Lindsey was recommended to us by a family friend who has had multiple positive interactions with her. She lived up to the hype! Lindsey was attentive without being overbearing. We never felt pushed or rushed with anything – her professionalism was top notch. Being first-time sellers, we relied upon Lindsey’s expert input on selling my mother’s condo. She recommended vendors, all of whom we would use again and recommend, for fixing things before going on the market. The property was listed, had multiple competitive offers within three days, and ended up closing within a month. Lindsey was still accessible after the sale, which makes me feel even more comfortable about using her again as an agent in the future. I very highly recommend Lindsey as a real estate agent.

Julie Johnson

We first met Lindsey when she was our buyers agent in 2021. We could not have asked for a better experience with Lindsey, as she helped us land the exact house we wanted in a competitive market! Throughout the entire process she was patient and open with us. Fast forward two years, and we found ourselves relocating to a different state. We used Lindsey again, this time to help us sell our home. From day one, Lindsey had a gameplan for how to market the house - photos, decor, listing price, everything. And after only one weekend on the market, we had an accepted offer for well over what we listed at! Buying or selling, you will be in great hands with Lindsey!

John A

I had an excellent experience with Lindsey in buying and selling my home. Lindsey was very patient in helping me find a new home. And when my job moved and I had to sell my home, I contacted Lindsey for help. Lindsey sold my home in about a month's time at a good price. I highly recommend her.

Kathleen Zelno

Lindsey is the best. She is exactly the type of real estate agent you want to work with: diligent, organized, responsive and above all helped make a stressful process fun! She was flexible with her time and more than willing to go above and beyond. She has a great understanding of the local market dynamics and was a great sounding board though out the process. We couldn't recommend her highly enough.

Stephen A.

Lindsey Rosen of William Pitt Sotheby’s International Realty is a very professional, knowledgeable and innovative realtor, who was referred to me after about six months of unsuccessful searching by agents from other Real Estate companies. She staged and advertised my two bedroom apartment in numerous venues, negotiated fine points of the lease agreement, reviewed applications, showed the property, and found an appropriate tenant in about 5 weeks. I recommend her whole heartedly.

1327 Bronson Road LLC

Lindsey was very helpful in the process of selling our home. Got things up and running quick, helped in the staging and hired an excellent photographer. Helped us through the process and sold quickly.

Emmanuel G

We entered our home search as first time buyers in a very unique market. From the first initial phone call with Lindsey, her warmth, sincerity, and care for our needs immediately put us at ease. Lindsey truly listens to her clients and works tirelessly on every detail throughout the process. It was such a relief to work with someone who is so professional, trustworthy, and knowledgeable in her field. We cannot recommend Lindsey enough!

Lauren and Josh

Lindsey R. was beyond amazing through this process. She was patient, and encouraging, and just so helpful in answer any questions or concerns. She stayed with me through the beginning of the process right through the very end at closing. My family and i are so thankful for everything she’s done to make this process go so smoothly.

Tiara Dawkins

I loved working with Lindsay Rosen to find my home in Westport! She goes the extra mile to make sure everything goes smoothly for her clients from finding a house that meets their wishlist to helping with local referrals. She genuinely feels less like an agent and more like a good friend helping you move to a new town. Do not hesitate to call her if you are looking to move!

Jessica Lubarsky

Lindsey is an amazing agent!! She is knowledgeable, responsive, and supported our family throughout our relocation. We highly recommend her!!!

Brian and Takeema Nicholls

I couldn’t have asked for a better realtor! Lindsey is professional, driven, responsive, organized, and on top of everything. I greatly appreciated her advice, candor, and attention to detail throughout the entire process, but it was her professionalism and business savvy that helped me land my dream home over multiple bids and in an incredibly competitive market. And to top it off, she was fun to work with! I would absolutely recommend enlisting Lindsey as your real estate agent.

Rachel Repko

Lindsey did a great job in helping me purchase my first home. She was very knowledgeable about the market and gave great suggestions. She was also very good at preventing potential issues. Lindsey was very professional and diligent making sure everything was on track with my closing. I would definitely work with her again.

Christina Phillips

My requirements were to lease an apartment in Fairfield not the largest of needs but was made to feel I was most important. Found the ideal space and I couldn’t be happier. Thank you for the excellent service.

Michael Siegel

My Listings

46 Churchill Street $2,100/mo link

46 Churchill Street

Fairfield, CT 06824 | Fairfield County
$2,100/mo
2 Beds 1 Baths 904 Sqft 0.11 Acres

Charming, spacious, and beautifully remoded! Light-filled open rooms with tall windows and gleaming hardwood floors create a warm and inviting feel. The spacious kitchen features...

2
bed
1
bath
904
sqft
29 Redfield Road $5,750/mo link

29 Redfield Road

Fairfield, CT 06824 | Fairfield County
$5,750/mo
5 Beds 2/1 Baths 1,493 Sqft 0.18 Acres

Welcome to 29 Redfield Road! Just steps from the train station and the Sportsplex, this soon-to-be fully restored home offers the perfect blend of historical charm and modern convenience....

5
bed
2/1
bath
1,493
sqft
621 Fairfield Beach Road $4,000/mo link

621 Fairfield Beach Road

Fairfield, CT 06824 | Fairfield County
$4,000/mo
2 Beds 1 Baths 680 Sqft 0.1 Acres

Academic Year Rental - Available for the 2026-2027 school year (September through May). Experience the quintessential beach lifestyle in this charming 2-bedroom cottage, just steps...

2
bed
1
bath
680
sqft

My Sales

24 Salt Box Lane $1,850,000 link

24 Salt Box Lane

Darien, CT 06820 | Fairfield County
$1,850,000
6 Beds 3/1 Baths 3,330 Sqft 0.4 Acres

Discover serenity in this charming colonial-style home nestled on a quiet cul-de-sac. just minutes away from Darien's town, Great Island, beaches, restaurants, shops, and train...

6
bed
3/1
bath
3,330
sqft
1350 South Pine Creek Road $1,800,000 link

1350 South Pine Creek Road

Fairfield, CT 06824 | Fairfield County
$1,800,000
4 Beds 3/1 Baths 6,274 Sqft 0.47 Acres

Sasco Point Shores ~ Majestic 4,333 SF Colonial with gunite pool offers three levels of living space with water views, just steps from LI Sound. Spacious, open floor plan offers...

4
bed
3/1
bath
6,274
sqft
10 Charcoal Hill Road $1,325,000 link

10 Charcoal Hill Road

Westport, CT 06880 | Fairfield County
$1,325,000
4 Beds 3/1 Baths 3,913 Sqft 0.79 Acres

Escape to the tranquility and serene ambiance of 10 Charcoal Hill Road in Westport CT. Designed by arguably one of Westport’s premier architects, Frazier Peters, this 4 bedroom...

4
bed
3/1
bath
3,913
sqft
23 Robert Court $1,160,000 link

23 Robert Court

Fairfield, CT 06824 | Fairfield County
$1,160,000
4 Beds 3 Baths 2,674 Sqft 0.24 Acres

Welcome to this beautifully expanded, updated Cape situated within a quiet cul-de-sac in one of Fairfield's most sought-after neighborhoods. Step into the inviting formal living...

4
bed
3
bath
2,674
sqft
30 Flax Road $1,050,000 link

30 Flax Road

Fairfield, CT 06824 | Fairfield County
$1,050,000
2 Beds 1/1 Baths 1,316 Sqft 0.24 Acres

Welcome to this stunning Cape Cod home, beautifully nestled on one of Fairfield's most beloved streets in the highly sought-after Sasco Hill neighborhood. Lovingly remodeled...

2
bed
1/1
bath
1,316
sqft
20 Half Mile Common $979,000 link

20 Half Mile Common

Westport, CT 06880 | Fairfield County
$979,000
4 Beds 3 Baths 2,285 Sqft 1.13 Acres

HOT NEW WESTPORT LISTING Under 1 MILLION Dollars. Located at the end of a cul de sac on 1.13 level acres within walking distance to The Porch (at Christie's Country Store ) Wakeman...

4
bed
3
bath
2,285
sqft
5 Maclean Place $960,000 link

5 Maclean Place

Branford, CT 06405 | New Haven County
$960,000
4 Beds 2/1 Baths 1,890 Sqft 0.1 Acres

Nestled in a picturesque beach community, this stunning 4 bedroom, 2.5 bathroom home embodies the ideal blend of charm and elegance, making it the perfect sanctuary for year-round...

4
bed
2/1
bath
1,890
sqft
762 Sport Hill Road $955,000 link

762 Sport Hill Road

Easton, CT 06612 | Fairfield County
$955,000
4 Beds 3 Baths 3,102 Sqft 3.1 Acres

Welcome to 762 Sport Hill Road! This exceptional home blends comfort, privacy, and modern updates, including a completely remodeled and finished basement. Set on 3 peaceful acres...

4
bed
3
bath
3,102
sqft
95 Dorking Drive $950,000 link

95 Dorking Drive

Fairfield, CT 06824 | Fairfield County
$950,000
4 Beds 3 Baths 2,870 Sqft 0.39 Acres

Welcome home! This deceptively spacious cape has everything you've been looking for, and then some! Located on a quiet street in the desirable University area, this home offers...

4
bed
3
bath
2,870
sqft
223 Misty Wood Lane $925,000 link

223 Misty Wood Lane

Fairfield, CT 06824 | Fairfield County
$925,000
4 Beds 2/1 Baths 2,949 Sqft 2.1 Acres

Recently refreshed with a newly painted kitchen, master bath, and living room! This 4 bedroom colonial rests on 2 acres, complete with bluestone patio, barn and gazebo, on a quiet...

4
bed
2/1
bath
2,949
sqft
1502 Round Hill Road $900,000 link

1502 Round Hill Road

Fairfield, CT 06824 | Fairfield County
$900,000
3 Beds 2 Baths 1,847 Sqft 0.29 Acres

 Welcome to 1502 Round Hill Road, a charming move in ready colonial, just minutes from Fairfield's award winning schools, beaches, train station and center of town. With...

3
bed
2
bath
1,847
sqft
27 Southfield Road $899,000 link

27 Southfield Road

Fairfield, CT 06824 | Fairfield County
$899,000
3 Beds 2/1 Baths 2,300 Sqft 0.14 Acres

Welcome to Southfield! Torn down to the studs, expanded and completely transformed this 3 bedroom 2.5 bath lives like new construction. The open floor plan design with high quality,...

3
bed
2/1
bath
2,300
sqft