Sandy Chittenden

Sandy Chittenden

Licensed Associate Real Estate Broker

Rye

49 Purchase Street
Rye, NY 10580

Stamford

3 Roxbury Road
Stamford, CT 06902
  • Born In:
    Rye, NY
  • Live In:
    Rye, NY

Sandy Chittenden is a lifelong Rye resident with a heart for her community and a passion for helping people feel truly at home. Having raised two daughters here and been deeply involved in their schools, sports, and local activities, Sandy brings an authentic, insider’s perspective to every real estate transaction. Her clients don’t just benefit from her market knowledge—they gain a trusted partner who genuinely cares.

With more than 28 years of experience in the Westchester real estate market, Sandy has built a reputation for excellence, integrity, and personalized service. She is consistently ranked among the Top 100 agents companywide and has been named one of the Best Real Estate Agents in Westchester by Westchester Magazine for 2023, 2024, and 2025—a testament to the trust and loyalty she’s earned from clients and colleagues alike.

Whether buying or selling, Sandy works tirelessly to make the process smooth, stress-free, and even enjoyable. She’s a skilled negotiator with a down-to-earth approach, and she uses the latest technology and social media strategies to market homes to the widest audience possible. Her goal is simple: to build lasting relationships and ensure every client feels confident, supported, and happy with their outcome.

Outside of real estate, Sandy is a passionate advocate for her community, especially through her work with Soul Ryeders, a volunteer-driven nonprofit supporting individuals and families affected by cancer. Her journey with the organization began in 2012 when she donated her own wig to The Wig Exchange, a program that provides high-quality wigs to women facing hair loss. Deeply moved by the mission, Sandy became a longtime volunteer and now serves as a client coordinator, walking alongside women in some of their most vulnerable moments—offering support, encouragement, and a personal touch that mirrors the care she gives her real estate clients.

When she's not helping clients or volunteering, you’ll often find Sandy walking along Rye’s beautiful coastline or spending time with her family.

Sandy is proud to be a member of the National Association of Realtors, New York State Association of Realtors, Westchester Putnam Board of Realtors, and Rye-Harrison Multiple Listing Service.

Sandy Chittenden is a lifelong Rye resident with a heart for her community and a passion for helping people feel truly at home. Having raised two daughters here and been deeply involved in their schools, sports, and local activities, Sandy brings an authentic, insider’s perspective to every real estate transaction. Her clients don’t just benefit from her market knowledge—they gain a trusted partner who genuinely cares.

With more than 28 years of experience in the Westchester real estate market, Sandy has built a reputation for excellence, integrity, and personalized service. She is consistently ranked among the Top 100 agents companywide and has been named one of the Best Real Estate Agents in Westchester by Westchester Magazine for 2023, 2024, and 2025—a testament to the trust and loyalty she’s earned from clients and colleagues alike.

Whether buying or selling, Sandy works tirelessly to make the process smooth, stress-free, and even enjoyable. She’s a skilled negotiator with a down-to-earth approach, and she uses the latest technology and social media strategies to market homes to the widest audience possible. Her goal is simple: to build lasting relationships and ensure every client feels confident, supported, and happy with their outcome.

Outside of real estate, Sandy is a passionate advocate for her community, especially through her work with Soul Ryeders, a volunteer-driven nonprofit supporting individuals and families affected by cancer. Her journey with the organization began in 2012 when she donated her own wig to The Wig Exchange, a program that provides high-quality wigs to women facing hair loss. Deeply moved by the mission, Sandy became a longtime volunteer and now serves as a client coordinator, walking alongside women in some of their most vulnerable moments—offering support, encouragement, and a personal touch that mirrors the care she gives her real estate clients.

When she's not helping clients or volunteering, you’ll often find Sandy walking along Rye’s beautiful coastline or spending time with her family.

Sandy is proud to be a member of the National Association of Realtors, New York State Association of Realtors, Westchester Putnam Board of Realtors, and Rye-Harrison Multiple Listing Service.

Sandy Chittenden is a lifelong Rye resident with a heart for her community and a passion for helping people feel truly at home. Having raised two daughters here and been deeply involved in their schools, sports, and local activities, Sandy brings an authentic, insider’s perspective to every real estate transaction. Her clients don’t just benefit from her market knowledge—they gain a trusted partner who genuinely cares.

With more than 28 years of experience in the Westchester real estate market, Sandy has built a reputation for excellence, integrity, and personalized service. She is consistently ranked among the Top 100 agents companywide and has been named one of the Best Real Estate Agents in Westchester by Westchester Magazine for 2023, 2024, and 2025—a testament to the trust and loyalty she’s earned from clients and colleagues alike.

Whether buying or selling, Sandy works tirelessly to make the process smooth, stress-free, and even enjoyable. She’s a skilled negotiator with a down-to-earth approach, and she uses the latest technology and social media strategies to market homes to the widest audience possible. Her goal is simple: to build lasting relationships and ensure every client feels confident, supported, and happy with their outcome.

Outside of real estate, Sandy is a passionate advocate for her community, especially through her work with Soul Ryeders, a volunteer-driven nonprofit supporting individuals and families affected by cancer. Her journey with the organization began in 2012 when she donated her own wig to The Wig Exchange, a program that provides high-quality wigs to women facing hair loss. Deeply moved by the mission, Sandy became a longtime volunteer and now serves as a client coordinator, walking alongside women in some of their most vulnerable moments—offering support, encouragement, and a personal touch that mirrors the care she gives her real estate clients.

When she's not helping clients or volunteering, you’ll often find Sandy walking along Rye’s beautiful coastline or spending time with her family.

Sandy is proud to be a member of the National Association of Realtors, New York State Association of Realtors, Westchester Putnam Board of Realtors, and Rye-Harrison Multiple Listing Service.

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My Listings

10 Stewart Place #2AW $449,000 link

10 Stewart Place #2AW

White Plains, NY 10603 | Westchester County
$449,000
1 Beds 2 Baths 1,132 Sqft

  New Price — Exceptional Value! Enjoy generous space, premium amenities, and unbeatable convenience in this bright 1-bed, 2-bath apt that features newly renovated...

1
bed
2
bath
1,132
sqft
630 Forest Avenue $3,495,000 link

630 Forest Avenue

Rye, NY 10580 | Westchester County
$3,495,000
5 Beds 4/1 Baths 4,064 Sqft 0.17 Acres

Welcome to your dream home, 630 Forest Avenue, Rye. This brand-new construction offers effortless living at its finest with high-end finishes, energy-efficient Geothermal heating...

5
bed
4/1
bath
4,064
sqft
116 North Street $1,490,000 link

116 North Street

Rye, NY 10580 | Westchester County
$1,490,000
5 Beds 3/2 Baths 2,260 Sqft 0.35 Acres

This Rye Cape/Colonial has charm and personality inside and out! With room for all it features 5 bedrooms, 3.5 baths, with beautiful hardwood floors throughout and a renovated...

5
bed
3/2
bath
2,260
sqft

My Sales

390 Forest Avenue $4,100,000 link

390 Forest Avenue

Rye, NY 10580 | Westchester County
$4,100,000
8 Beds 6/2 Baths 6,516 Sqft 0.82 Acres

Unique opportunity to own one of Rye's Grand older homes, completely renovated in 2010. This level Mini-Estate, on almost a full acre, is completely fenced, has Rye City "specimen"...

8
bed
6/2
bath
6,516
sqft
14 Morris Court $3,775,000 link

14 Morris Court

Rye, NY 10580 | Westchester County
$3,775,000
4 Beds 4/2 Baths 5,200 Sqft 0.59 Acres

Elegant white birch trees, soaring arborvitae and a professionally designed perennial garden welcome you to this happy and luxurious jewel box located on a coveted cul-de-sac in...

4
bed
4/2
bath
5,200
sqft
22 Chamberlain Street $3,755,000 link

22 Chamberlain Street

Rye, NY 10580 | Westchester County
$3,755,000
6 Beds 5/1 Baths 4,457 Sqft 0.22 Acres

This is the one you've been waiting for! Just completed and nestled in one of Rye’s most coveted neighborhoods, this breathtaking new home combines luxury, style, and functionality....

6
bed
5/1
bath
4,457
sqft
351 Park Avenue $3,575,000 link

351 Park Avenue

Rye, NY 10580 | Westchester County
$3,575,000
6 Beds 7/2 Baths 7,804 Sqft 0.56 Acres

Elegance meets functionality in this exquisitely designed and appointed 2016 build by a respected Rye builder. This 6 bedroom 7 bath home is the essence of modern living, crisp...

6
bed
7/2
bath
7,804
sqft
11 Halls Lane $3,330,000 link

11 Halls Lane

Rye, NY 10580 | Westchester County
$3,330,000
4 Beds 3/1 Baths 3,134 Sqft 0.23 Acres

Welcome to 11 Halls Lane! This is the home you have been waiting for! Located in the heart of the coveted Milton Point area of Rye, New York is this beautifully updated 4 bedroom,...

4
bed
3/1
bath
3,134
sqft
26 Valleyview Avenue $3,000,000 link

26 Valleyview Avenue

Rye, NY 10580 | Westchester County
$3,000,000
4 Beds 4/1 Baths 3,012 Sqft 0.17 Acres

Resort like living in this spacious 4 Bedroom square foot Colonial in highly desirable Milton Point neighborhood. Close to school, beach, parks. This inviting home draws you in...

4
bed
4/1
bath
3,012
sqft
65 North Street $2,756,000 link

65 North Street

Rye, NY 10580 | Westchester County
$2,756,000
5 Beds 4/1 Baths 4,555 Sqft 0.36 Acres

A covered front porch welcomes you to this young Center Hall Colonial. Prepare to fall in love, this airy 5 bedroom 4.1 bath home offers over 4500 sq feet of amazing space ,sited...

5
bed
4/1
bath
4,555
sqft
71 Oakland Beach Avenue $2,595,000 link

71 Oakland Beach Avenue

Rye, NY 10580 | Westchester County
$2,595,000
5 Beds 4/1 Baths 3,267 Sqft 0.24 Acres

Welcome to 71 Oakland Beach Avenue! This stunning, recently-completed home offers the epitome of modern comfort and style. Spread out and enjoy ample space in this expansive 5...

5
bed
4/1
bath
3,267
sqft
40 Claremont Avenue $2,595,000 link

40 Claremont Avenue

Rye, NY 10580 | Westchester County
$2,595,000
5 Beds 4/1 Baths 4,390 Sqft 0.23 Acres

Another outstanding home to be built by P&I Custom Builders. This 5 bedroom 4 full and one half bath home will exceed your expectations. Superb craftsmanship, custom details, exceptional...

5
bed
4/1
bath
4,390
sqft
108 Claremont Avenue $2,520,000 link

108 Claremont Avenue

Rye, NY 10580 | Westchester County
$2,520,000
5 Beds 4/1 Baths 4,323 Sqft 0.22 Acres

Spectacular New construction. Another outstanding home by P&I Custom Builders. This classic 5 bedroom colonial will exceed your expectations. Superb craftsmanship, custom details,...

5
bed
4/1
bath
4,323
sqft