Jennifer (Jenny) Holmes

Jennifer (Jenny) Holmes

Licensed Real Estate Salesperson

Rye

49 Purchase Street
Rye, NY 10580

Stamford

3 Roxbury Road
Stamford, CT 06902
  • Born In:
    New York, NY
  • Live In:
    Purchase, NY
  • Favorite Movie:
    Country Strong
  • Passion:
    Family
  • Interests:
    Walking, Reading, Tennis, Crossword Puzzles
  • Favorite Lyric:
    "Timing is everything."
  • Can’t Live Without:
    My dog George
  • Inspiration:
    My Mom

Jenny Holmes is a nationally recognized Realtor, serving clientele across Westchester County, NY, and Fairfield County, CT. Consistently ranking within the Top 1% of her company, Jenny’s expertise and commitment to excellence have made her a trusted name in the real estate market. Jenny successfully managed transactions ranging from $275,000 to $7.3 million, reinforcing her reputation for delivering exceptional results. Jenny's impressive achievements have earned her the distinction of being a leading agent at the Rye office of Julia B. Fee Sotheby’s International Realty. 

With over 20 years of experience in the industry, Jenny’s career began at her family’s real estate firm and flourished upon joining Julia B. Fee Sotheby’s International Realty in 2008. Jenny understands that home is more than just a place—it’s where life happens, where comfort, lifestyle, and memories are created. Whether representing a buyer or a seller, Jenny approaches each transaction with this core belief, ensuring every property is showcased to its highest potential. Her strategic approach has resulted in a 100.2% sell-to-list ratio for her sellers, while her insightful advice ensures that buyers navigate today’s competitive market with confidence.

A lifelong Westchester resident, Jenny’s roots run deep—from her childhood in Rye to her current home in Purchase. She and her husband, Billy, raised their twin daughters, Madison and Savannah, along with their beloved rescue pups, George and Booker. Jenny enjoys outdoor activities such as hiking, tennis, and kayaking on the Sound, embracing the beauty of the area she knows so well.  

Beyond her professional success, Jenny is a dedicated community advocate. She actively supports a variety of local and educational initiatives, including My Sisters' Place, Children's Hope Chest, the Harrison Educational Foundation, and the University of Virginia Alumni Association. Her passion for both her career and her community truly distinguishes her as a Realtor of unparalleled distinction.

 

Jenny Holmes is a nationally recognized Realtor, serving clientele across Westchester County, NY, and Fairfield County, CT. Consistently ranking within the Top 1% of her company, Jenny’s expertise and commitment to excellence have made her a trusted name in the real estate market. Jenny successfully managed transactions ranging from $275,000 to $7.3 million, reinforcing her reputation for delivering exceptional results. Jenny's impressive achievements have earned her the distinction of being a leading agent at the Rye office of Julia B. Fee Sotheby’s International Realty. 

With over 20 years of experience in the industry, Jenny’s career began at her family’s real estate firm and flourished upon joining Julia B. Fee Sotheby’s International Realty in 2008. Jenny understands that home is more than just a place—it’s where life happens, where comfort, lifestyle, and memories are created. Whether representing a buyer or a seller, Jenny approaches each transaction with this core belief, ensuring every property is showcased to its highest potential. Her strategic approach has resulted in a 100.2% sell-to-list ratio for her sellers, while her insightful advice ensures that buyers navigate today’s competitive market with confidence.

A lifelong Westchester resident, Jenny’s roots run deep—from her childhood in Rye to her current home in Purchase. She and her husband, Billy, raised their twin daughters, Madison and Savannah, along with their beloved rescue pups, George and Booker. Jenny enjoys outdoor activities such as hiking, tennis, and kayaking on the Sound, embracing the beauty of the area she knows so well.  

Beyond her professional success, Jenny is a dedicated community advocate. She actively supports a variety of local and educational initiatives, including My Sisters' Place, Children's Hope Chest, the Harrison Educational Foundation, and the University of Virginia Alumni Association. Her passion for both her career and her community truly distinguishes her as a Realtor of unparalleled distinction.

 

Jenny Holmes is a nationally recognized Realtor, serving clientele across Westchester County, NY, and Fairfield County, CT. Consistently ranking within the Top 1% of her company, Jenny’s expertise and commitment to excellence have made her a trusted name in the real estate market. Jenny successfully managed transactions ranging from $275,000 to $7.3 million, reinforcing her reputation for delivering exceptional results. Jenny's impressive achievements have earned her the distinction of being a leading agent at the Rye office of Julia B. Fee Sotheby’s International Realty. 

With over 20 years of experience in the industry, Jenny’s career began at her family’s real estate firm and flourished upon joining Julia B. Fee Sotheby’s International Realty in 2008. Jenny understands that home is more than just a place—it’s where life happens, where comfort, lifestyle, and memories are created. Whether representing a buyer or a seller, Jenny approaches each transaction with this core belief, ensuring every property is showcased to its highest potential. Her strategic approach has resulted in a 100.2% sell-to-list ratio for her sellers, while her insightful advice ensures that buyers navigate today’s competitive market with confidence.

A lifelong Westchester resident, Jenny’s roots run deep—from her childhood in Rye to her current home in Purchase. She and her husband, Billy, raised their twin daughters, Madison and Savannah, along with their beloved rescue pups, George and Booker. Jenny enjoys outdoor activities such as hiking, tennis, and kayaking on the Sound, embracing the beauty of the area she knows so well.  

Beyond her professional success, Jenny is a dedicated community advocate. She actively supports a variety of local and educational initiatives, including My Sisters' Place, Children's Hope Chest, the Harrison Educational Foundation, and the University of Virginia Alumni Association. Her passion for both her career and her community truly distinguishes her as a Realtor of unparalleled distinction.

 

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Testimonials

We had the best experience with Jenny Holmes. She’s helpful, genuine, and a fun person. Couldn’t recommend more.

Justin and Raphael Swenson

Jenny and Christian were professional and super helpful with their suggestions that helped us sell our home quickly and at the market price.

Christopher and Lorri Riegler

Both Jenny and Madison did a great job getting us apartment B32. They really look after us.

Richard and Martha Pagen

Jenny is the best. I felt really well cared for the entire process. She knows the Rye Market extremely well and we were lucky to have her.

Alison and Jason Clain

Excellent!

Daniel M. and Zareen Bayly

Our agent Jennifer Holmes was extremely attentive and assisted us in every way with the process of buying our new home and selling our present home.

Steven and Frances Rosenberg

Very kind, smart and patient. Jenny was a pleasure to work with. Thank you.

Paula Butler

Jenny Holmes is absolutely the best. As is her daughter Madison who worked with her. Jenny is the one to have on your side, whether buying or selling. Madison brings a thoughtful, smart, and kind perspective which makes her very valuable to clients like us.

Dick and Martha Pagen

Excellent Broker. I wish I had a person like Jennifer working for my company. SHE SHOULD BE REWARDED

Edward and Jayne Bieber

Second time we have worked with Jenny. Both were great experiences. She took the time to understand what we were looking for and found us options that matched our goals, giving us a real choice. She continued to help through the paperwork all the way though our move in. Cannot recommend her enough.

John J. and Shawn O'Neil

Lisa and Jenny were so lovely! They helped demystify the process of buying a home and we’re wonderful to work with throughout the entire process.

Elizabeth Hil Kennedy

X

Catherine Foulkes

Jenny Holmes is great! She is on top of everything and very quick to respond to questions and requests.

Michael Tomaino

Jenny was absolutely wonderful during this whole process - from start to finish !! I can’t tell you how seamless she made a difficult emotional process for me ! Thank you Jenny and team ! Beth Meister

Estate of William Straus

Jenny Holmes was amazing - we were looking for a home in Rye while we are living in California - Jenny was always there for us and went out of her way to show us homes virtually and in person - we recommend her with the highest rating.

Alexandra and Eric Weinberger

Jenny Holmes is exceptional. She is thoughtful and focused and gives helpful advice. We know we are in good hands when represented by Jenny and William Pitt/Julia B. Fee Sotheby's International Realty

Susan and James Schwab

Jenny was a pleasure to work with - she kept our needs in mind throughout the entire process, and helped us find the perfect home for our family!

Amy; Eric Skott Pearl; Hartford

Jenny was extremely helpful in our rental search, and we are grateful that she thought of us and our family! We have already recommended her to other friend looking to come to Rye this fall! Thank you!

Vivekanand Yerrapu; Kathryn Reddy

I was represented by Jenny Holmes in the sale of my home. She walked me through the home selling process seamlessly. She is a consummate professional and guided me the preparation of my home to handling a multiple bidding situation on my property that resulted in a favorable outcome for myself.”

Rye Resident

Thank you for helping us so expertly and calmly through the process of selling and moving. We always knew you had our backs and we definitely appreciate all the little things you did to smooth the way when the various obstacles arose. It was not an easy process (probably never is) but you were straightforward and professional throughout and so easy to work with.

Harrison, New York

An email sent to Paul Breunich, President and Chief Executive Officer. I am reaching out to you to let you know about our recent experience working with Jenny Holmes on the sale of our home. As I'm sure you know, there are many realtors in your industry who take on their role as a job or position to pass the time, but to Jenny, it's a career and that clearly came across during our engagement with her. Given my vocation, retaining the right person to advise my wife and me on the sale of our home was quite important. I interviewed a select few and none came close to what Jenny possesses as an advisor. Aside from the typical advice for preparing a home to go on the market and showings to prospective buyers, Jenny's value was during the marketing and negotiating stages. She was extremely strategic in her negotiations and her advice to us was spot-on every time. She managed our expectations and provided sound advice throughout the entire process. Her experience really showed during those negotiations and the end result was a great success.

Harrison, New York

Jenny Holmes is a very savvy, honest broker that holds her clients and their best interest in the highest regard. We had a difficult transaction and she took control of the situation and guided us to a successful sale.”

Harrison Resident

We hold Jenny in the highest regard and want to make sure your office knows how much we appreciate her hard work, advice and professionalism. She has done an amazing job that has encompassed all aspects of our new home purchase and previous home sale. We were passively looking for a new home in Rye as we had finished renovating our existing home just a few years ago. We knew we would only be interested in moving if we could find a new construction or a relocation to a quieter area. Also, within a modest increase to what we perceived to be our current value of our home. Through a lot of time, patience, and active listening on her part Jenny helped us find a home that fit what we were looking for perfectly. She focused on showing us the listings we would potentially have interest in and she always found time to meet with us within our busy schedules. She expertly handled all aspects of both transactions, from the negotiation on the purchase of our new home to negotiating the sale of our existing home successfully and swiftly. She had a clear understanding of key decision issues and the marketplace overall. She is an outstanding broker and we truly appreciate how she made a difficult process run smoothly from start to finish. She is a true professional and has been a pleasure to work with.

Jim and Susan Schwab

“Jenny Holmes is a very savvy, honest broker that holds her clients and their best interest in the highest regard. We had a difficult transaction and she took control of the situation and guided us to a successful sale.”

Harrison Resident

“I was represented by Jenny Holmes in the sale of my home. She walked me through the home selling process seamlessly. She is a consummate professional and guided me the preparation of my home to handling a multiple bidding situation on my property that resulted in a favorable outcome for myself.”

Rye Resident

My Listings

622 W 256th Street $3,750,000 link

622 W 256th Street

Bronx, NY 10471 | Bronx County
$3,750,000
6 Beds 5/1 Baths 6,271 Sqft 0.27 Acres

Modern elegance defines this stunning custom-built home in Riverdale. Designed for those with a penchant for high-end finishes and sophisticated living, this property is a true...

6
bed
5/1
bath
6,271
sqft
120 Old Post Road #E305 $2,150,000 link

120 Old Post Road #E305

Rye, NY 10580 | Westchester County
$2,150,000
2 Beds 2/1 Baths 1,602 Sqft

Step into elegance at the St. Regis Residences of Rye, a premier 55+ community offering an exceptional living experience. This fully renovated 2-bedroom, 2.5-bathroom apartment...

2
bed
2/1
bath
1,602
sqft
6 Valley Place $2,395,000 link

6 Valley Place

Harrison, NY 10528 | Westchester County
$2,395,000
5 Beds 4/2 Baths 3,784 Sqft 1.01 Acres

Discover the elegance of 6 Valley Place, a stunning home set in the prestigious town of Harrison, NY. This open concept 3,800 square foot residence offers an inviting blend of...

5
bed
4/2
bath
3,784
sqft

My Sales

980 Forest Avenue $7,600,000 link

980 Forest Avenue

Rye, NY 10580 | Westchester County
$7,600,000
6 Beds 6/2 Baths 8,145 Sqft 1 Acres

With spectacular direct water views from all levels on desirable Milton Point, this Hamptons style shingle home offers the ultimate in lifestyle and luxury. 980 Forest Ave offers...

6
bed
6/2
bath
8,145
sqft
590 Forest Avenue $5,200,000 link

590 Forest Avenue

Rye, NY 10580 | Westchester County
$5,200,000
5 Beds 5/1 Baths 6,233 Sqft 0.33 Acres

No detail was overlooked in the meticulous construction of this colonial overlooking Rye Town Park with water views from many rooms. This 5 BR, 5.1 bath home was custom built with...

5
bed
5/1
bath
6,233
sqft
612 Forest Avenue $5,200,000 link

612 Forest Avenue

Rye, NY 10580 | Westchester County
$5,200,000
6 Beds 6/1 Baths 6,233 Sqft 0.34 Acres

This just completed custom home built by CADCO is designed for its setting, offering Rye shoreline water views that look thru the Rye Town Park. Clean lines, enduring materials,...

6
bed
6/1
bath
6,233
sqft
124 Bradford Avenue $4,749,000 link

124 Bradford Avenue

Rye, NY 10580 | Westchester County
$4,749,000
6 Beds 5/2 Baths 6,786 Sqft 0.56 Acres

A Modern Shingle Style Home Like No Other! NEWLY BUILT IN 2014 nestled on a LUSH and PRIVATE HALF ACRE with room for a POOL! Every aspect of his stunning beauty was carefully selected...

6
bed
5/2
bath
6,786
sqft
590 Forest Avenue $4,525,000 link

590 Forest Avenue

Rye, NY 10580 | Westchester County
$4,525,000
5 Beds 5/1 Baths 6,233 Sqft 0.33 Acres

No detail was overlooked in the meticulous construction of this colonial overlooking Rye Town Park with water views from many rooms. This 5 BR, 5.1 bath home was custom built for...

5
bed
5/1
bath
6,233
sqft
120 Old Post Road #PH-E301 $4,285,000 link

120 Old Post Road #PH-E301

Rye, NY 10580 | Westchester County
$4,285,000
4 Beds 4/1 Baths 3,108 Sqft

The St. Regis Residences, Rye- A Life Extraordinary - Welcome to the St. Regis Residences Rye, a 55+ luxury lifestyle community. This exquisitely-designed collection of condominium...

4
bed
4/1
bath
3,108
sqft
11 Archer Road $3,900,000 link

11 Archer Road

Harrison, NY 10528 | Westchester County
$3,900,000
5 Beds 5/1 Baths 8,640 Sqft 1.8 Acres

Discover luxury living at 11 Archer Road in Harrison, New York. Situated in the heart of Harrison's coveted Sterling Ridge. This thoughtfully designed home went through an extensive...

5
bed
5/1
bath
8,640
sqft
34 Lincoln Lane $3,787,500 link

34 Lincoln Lane

Purchase, NY 10577 | Westchester County
$3,787,500
8 Beds 7/4 Baths 10,210 Sqft 5 Acres

Taxes successfully grieved! Assessment reduced by 25%! Reduction will be implemented 2/2020. Spectacular colonial residence situated at the end of a peaceful cul-de-sac, in an...

8
bed
7/4
bath
10,210
sqft
120 Old Post Road #E106 $3,745,000 link

120 Old Post Road #E106

Rye, NY 10580 | Westchester County
$3,745,000
4 Beds 4/1 Baths 2,775 Sqft

The St. Regis Residences, Rye- A Life Extraordinary - Welcome to the St. Regis Residences Rye, a 55+ luxury lifestyle community. This exquisitely-designed collection of condominium...

4
bed
4/1
bath
2,775
sqft
35 Evergreen Avenue $3,720,000 link

35 Evergreen Avenue

Rye, NY 10580 | Westchester County
$3,720,000
6 Beds 5/1 Baths 5,100 Sqft 0.27 Acres

Located in the heart of Rye, just steps away from train station, restaurants, shops and Rye Country Day School, this exceptional Colonial home offers an unparalleled lifestyle...

6
bed
5/1
bath
5,100
sqft
670 Milton Road $3,692,000 link

670 Milton Road

Rye, NY 10580 | Westchester County
$3,692,000
4 Beds 3/1 Baths 3,386 Sqft 0.23 Acres

LIFESTYLE home on Milton Point- a BOATER'S DREAM!! Pull up to your own private deep water dock after a breathtaking sunset cruise. This luxury waterfront colonial boasts 10ft ceilings...

4
bed
3/1
bath
3,386
sqft
7 Red Oak Drive $3,550,000 link

7 Red Oak Drive

Rye, NY 10580 | Westchester County
$3,550,000
6 Beds 4/1 Baths 4,400 Sqft 0.2 Acres

Introducing 7 Red Oak Drive - Just completed 6-bedroom, 4.5 bathroom new construction in Rye, NY. On the first floor you will find a fully equipped chef's kitchen created by Corvino...

6
bed
4/1
bath
4,400
sqft