Caroline Shepherd

Bedford NY

Houlihan Lawrence Inc.

40 Closed Sales

$60.8M Total Value

$640K - $4.3M Price Range

$1.5M Average Price

Prior 5 years

About Caroline

Caroline has decades of Real Estate Experience. Throughout the years her achievements include her rank in New York's Top Ten as well as receiving the Westchester County Board of Realtors Diamond Award for Excellence. A consistent top producer, receiving Silver, Gold, and Platinum awards in sales. Caroline is also a winner of the Westchester Magazine Five Star Agent award. Caroline is licensed in NY and in Connecticut, serving the Fairfield County communities of Ridgefield, Redding, Wilton, Westport, and Weston.

Most recently, Caroline officiated as the Global Luxury Director for Coldwell Banker NRT Westchester and Connecticut, sharpening her management and marketing skills in the luxury segment of the market. Currently, she is back to doing what she enjoys most: assisting buyers and sellers in skillfully navigating the buying and selling process from start to finish.

Caroline's objectives are clear; to listen in a caring way to her client's needs and to utilize sound planning, professional ethics, strong communication skills and a solid company support system to maintain a high standard of service.

Home Types: House, Condo, Co-op, Townhouse, Lot/Land

Years of Experience: 14

Transaction History

1 Year
2 Year
5 Year

Seller Deals

Total Deals

Total Value

$8,531,100

Average Sale Price

$1,706,220

Price Range

$960K - $3M

Buyer Deals

Total Deals

Neighborhoods Caroline is Experienced In

Caroline's Active Listings

$789,000
- 4 Beds
- 2.5 Baths
- 2,274 Sq Ft
15 Laurel Rd

Pound Ridge, NY
*4/20/26 Best and final offers due on Tuesday 4/21 at 12 noon.* Owned by the same family for more than 50 years, this light-filled 4-bedroom, 2.5 bath home offers a spacious, easy flow. Mostly original to its build date, it's complimented by hardwood floors throughout and a stylishly renovated primary bath. Set on 2 acres in the heart of Pound Ridge, the property delivers a sense of privacy with

Caroline Shepherd Houlihan Lawrence Inc.

Recently Sold

$2,995,000 Sold Mar 31, 2026
- 3 Beds
- 3.5 Baths
- 11,339 Sq Ft
64 Pound Ridge Rd

Pound Ridge, NY
- $264/SF
- 33 Days On Market
- Current Est. Value $3M
Caroline Shepherd Houlihan Lawrence Inc.

$1,275,000 Sold Mar 25, 2026
- 4 Beds
- 2 Baths
- 2,139 Sq Ft
35 Hamilton Rd

Chappaqua, NY
- 11% Above List
- $596/SF
- 12 Days On Market
- Current Est. Value $1M
Caroline Shepherd Houlihan Lawrence Inc.

$2,101,100 Sold Jul 30, 2025
- 3 Beds
- 3 Baths
- 3,526 Sq Ft
56 West Ln

Pound Ridge, NY
- 15% Above List
- $596/SF
- 15 Days On Market
- Current Est. Value $2M
Caroline Shepherd Houlihan Lawrence Inc.

$4,250,000 Sold Oct 4, 2024
- 6 Beds
- 4.5 Baths
- 5,756 Sq Ft
20 Hoyts Ln

Mount Kisco, NY
- 6% Below List
- $738/SF
- 92 Days On Market
- Current Est. Value $4M
Caroline Shepherd Houlihan Lawrence Inc.

$2,550,000 Sold Aug 27, 2024
- 4 Beds
- 5.5 Baths
- 5,576 Sq Ft
108 Hickory Kingdom Rd

Bedford, NY
- 9% Above List
- $457/SF
- 22 Days On Market
- Current Est. Value $3M
Caroline Shepherd Houlihan Lawrence Inc.

$2,350,000 Sold Aug 13, 2024
- 4 Beds
- 6 Baths
- 5,736 Sq Ft
23 Meeting House Rd

Mount Kisco, NY
- 21% Above List
- $410/SF
- 12 Days On Market
- Current Est. Value $3M
Caroline Shepherd Houlihan Lawrence Inc.

$1,692,500 Sold Feb 5, 2024
- 2 Beds
- 3 Baths
- 2,370 Sq Ft
57 Cross Pond Rd

Pound Ridge, NY
- $714/SF
- 23 Days On Market
- Current Est. Value $2M
Caroline Shepherd Houlihan Lawrence Inc.

$1,325,000 Sold Sep 18, 2023
- 4 Beds
- 3.5 Baths
- 3,880 Sq Ft
190 Green Ln

Bedford Hills, NY
- 4% Above List
- $341/SF
- 20 Days On Market
- Current Est. Value $2M
Caroline Shepherd Houlihan Lawrence Inc.

$720,000 Sold Aug 15, 2023
- 2 Beds
- 1 Bath
- 960 Sq Ft
26 Jackson Rd

Bedford, NY
- 15% Above List
- $750/SF
- 17 Days On Market
- Current Est. Value $807K
Caroline Shepherd Houlihan Lawrence Inc.

Agent License: 30SH0650520 New York 30SH0650520

Caroline Shepherd

(914) 281-2171

Homes for Sale by City

Caroline Shepherd

About Caroline

Transaction History

Seller Deals

Buyer Deals

Production Over Time

1 Year View by Quarter

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Neighborhoods Caroline is Experienced In

Caroline's Listings and Deals

Caroline's Active Listings

Recently Sold