Jen Whitaker

Orleans MA

Gibson Sotheby's International Realty

53 Closed Sales

$57.8M Total Value

$475K - $2.7M Price Range

$1.1M Average Price

Prior 5 years

About Jen

Home Types: House, Condo, Townhouse, Lot/Land, MultiFamily

Years of Experience: 10

Transaction History

1 Year
2 Year
5 Year

Seller Deals

Total Deals

Total Value

$7,112,500

Average Sale Price

$1,016,071

Price Range

$420K - $1.7M

Buyer Deals

Total Deals

Total Value

$1,675,000

Average Sale Price

$837,500

Price Range

$725K - $950K

Seller Deals

Total Deals

Total Value

$12,961,000

Average Sale Price

$1,080,083

Price Range

$420K - $2M

Buyer Deals

Total Deals

Total Value

$6,907,500

Average Sale Price

$986,786

Price Range

$475K - $2.4M

Seller Deals

Total Deals

Total Value

$38,474,055

Average Sale Price

$1,068,724

Price Range

$184K - $2.7M

Buyer Deals

Total Deals

Total Value

$19,340,000

Average Sale Price

$1,137,647

Price Range

$475K - $2.6M

5 Year View

Neighborhoods Jen is Experienced In

Jen's Active Listings

$2,300,000
- 5 Beds
- 5 Baths
- 4,091 Sq Ft
22 Winslow Dr

Orleans, MA
Overlooking a tranquil pond, 22 Winslow Drive offers a peaceful setting with a strong sense of privacy. Birds move easily through the surrounding landscape, and the quiet setting creates a calm and natural atmosphere. This gracious Cape Cod home has been cherished by four generations. Thoughtfully expanded over the years while preserving its warmth and character. Inside, more than 4,000 square

Jen Whitaker Gibson Sotheby's International Realty

$1,900,000
- 7 Beds
- 8 Baths
- 3,234 Sq Ft
216 Main St

Orleans, MA
Now's your chance to own one of East Orleans' most iconic properties!Once home to the beloved Kadee's Lobster & Clam Bar, a bustling fish market, a welcoming gift shop, and the ever-popular Apple Grove Mini Golf, this unforgettable property is ready for its next chapter. At the heart of it all is the original family home, which later became Kadee's Gray Elephant Inn, offering classic Cape charm

Jen Whitaker Gibson Sotheby's International Realty

Recently Sold

$820,000 Sold Apr 1, 2026
- 2 Beds
- 1.5 Baths
- 2,192 Sq Ft
55 Grandfathers Way

Eastham, MA
- 1% Below List
- $374/SF
- 58 Days On Market
- Current Est. Value $842K
Jen Whitaker Gibson Sotheby's International Realty

$980,000 Sold Jan 5, 2026
- 4 Beds
- 2 Baths
- 1,728 Sq Ft
21 Sea Meadow Ln

Brewster, MA
- 2% Above List
- $567/SF
- 8 Days On Market
- Current Est. Value $999K
Jen Whitaker Gibson Sotheby's International Realty

$420,000 Sold Dec 3, 2025
- 1 Bed
- 1 Bath
- 417 Sq Ft
70 Commercial St

Unit C

Wellfleet, MA
- 1% Above List
- $1,007/SF
- 8 Days On Market
- Current Est. Value $413K
Jen Whitaker Gibson Sotheby's International Realty

$740,000 Sold Dec 3, 2025
- 3 Beds
- 2 Baths
- 1,192 Sq Ft
85 Yankee Dr

Brewster, MA
- 5% Above List
- $621/SF
- 4 Days On Market
- Current Est. Value $760K
Jen Whitaker Gibson Sotheby's International Realty

$1,700,000 Sold Jun 25, 2025
- 3 Beds
- 2 Baths
- 2,080 Sq Ft
44 Loomis Ln

Orleans, MA
- 11% Below List
- $817/SF
- 12 Days On Market
- Current Est. Value $2M
Jen Whitaker Gibson Sotheby's International Realty

$1,565,000 Sold May 2, 2025
- 3 Beds
- 4 Baths
- 2,760 Sq Ft
55 Twine Field Dr

Chatham, MA
- 11% Below List
- $567/SF
- 30 Days On Market
- Current Est. Value $2M
Jen Whitaker Gibson Sotheby's International Realty

$1,675,000 Sold Mar 14, 2025
- 3 Beds
- 2.5 Baths
- 2,507 Sq Ft
11 Seaview Rd

Orleans, MA
- 16% Below List
- $668/SF
- 99 Days On Market
- Current Est. Value $1M
Jen Whitaker Gibson Sotheby's International Realty

$920,000 Sold Nov 22, 2024
- 4 Beds
- 2 Baths
- 2,480 Sq Ft
150 Meadow Dr

Eastham, MA
- 2% Below List
- $371/SF
- 22 Days On Market
- Current Est. Value $975K
Jen Whitaker Gibson Sotheby's International Realty

$425,000 Sold Oct 4, 2024
- 2 Beds
- 1.5 Baths
- 920 Sq Ft
21 Johnson Ln

West Yarmouth, MA
- 10% Above List
- $462/SF
- 7 Days On Market
- Current Est. Value $486K
Jen Whitaker Gibson Sotheby's International Realty

Agent License: Massachusetts 448013754

Jen Whitaker

(508) 501-9092

Homes for Sale by City

Jen Whitaker

About Jen

Transaction History

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Neighborhoods Jen is Experienced In

Jen's Listings and Deals

Jen's Active Listings

Recently Sold