Jen Whitaker

Orleans MA

Gibson Sotheby's International Realty

50 Closed Sales

$55.9M Total Value

$550K - $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	5
Total Value	$3,847,500
Average Sale Price	$769,500
Price Range	$420K - $980K

Buyer Deals
Total Deals	1
Total Value	$725,000
Average Sale Price	$725,000

Seller Deals
Total Deals	11
Total Value	$12,132,500
Average Sale Price	$1,102,955
Price Range	$420K - $2M

Buyer Deals
Total Deals	5
Total Value	$5,845,000
Average Sale Price	$1,169,000
Price Range	$620K - $2.4M

Seller Deals
Total Deals	34
Total Value	$37,199,055
Average Sale Price	$1,094,090
Price Range	$184K - $2.7M

Buyer Deals
Total Deals	16
Total Value	$18,690,000
Average Sale Price	$1,168,125
Price Range	$475K - $2.6M

5 Year View

Neighborhoods Jen is Experienced In

Jen's Active Listings

$2,150,000
- 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

Joint Agent

$1,195,000
- 3 Beds
- 1 Bath
- 1,040 Sq Ft
60 Billingsgate Ave

Eastham, MA
Target View Beach!! Across the street where the waterfront homes don't own the beach but you do as part of this exclusive association with deeded beach rights!! Sunsets & tidal flats, private walkways and secluded sand! Fancy fresh water? Walk to Wiley Park and Great Pond. This location couldn't be better. Enjoy the vintage vibe in a piece of Old Cape Cod. This 3 bedroom has all you need for a

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 $817K
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 $1M
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 $398K
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 $752K
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 $1M
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 $932K
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 $497K
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