Jen Whitaker Real Estate Agent - Gibson Sotheby's International Realty

15 Alice Rd, Eastham, MA For Sale $605,000 - listed by Jen Whitaker — For Sale $605,000

Section Image — For Sale $605,000

Jen Whitaker co-listing agent for 60 Billingsgate Ave, Eastham, MA - sold for $1,450,000 — Sold $1,450,000 • Co-Listing Agent

22 Winslow Dr, Orleans, MA Pending $2,150,000 - listed by Jen Whitaker — Pending $2,150,000

Section Image — Pending $2,150,000

Jen Whitaker buyer's agent for 36 Pursel Dr, North Chatham, MA - sold for $1,381,000 — Sold $1,381,000

216 Main St, Orleans, MA Pending $1,900,000 - listed by Jen Whitaker — Pending $1,900,000

Section Image — Pending $1,900,000

Jen Whitaker listing agent for 70 Commercial St Unit C, Wellfleet, MA - sold for $420,000 — Sold $420,000

Jen Whitaker

Gibson Sotheby's International Realty

11 Closed Sales

$13.8M Total Value

$740K - $2.6M Price Range

$1.3M Average Price

Prior 5 years

About Jen

Home Types: House, Townhouse

Years of Experience: 10

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	5
Total Value	$4,477,500
Average Sale Price	$895,500
Price Range	$420K - $1.5M

Buyer Deals
Total Deals	2
Total Value	$2,921,000
Average Sale Price	$1,460,500
Price Range	$1.4M - $1.5M

Seller Deals
Total Deals	6
Total Value	$6,042,500
Average Sale Price	$1,007,083
Price Range	$420K - $1.6M

Buyer Deals
Total Deals	2
Total Value	$2,921,000
Average Sale Price	$1,460,500
Price Range	$1.4M - $1.5M

Seller Deals
Total Deals	7
Total Value	$7,342,500
Average Sale Price	$1,048,929
Price Range	$420K - $1.6M

Buyer Deals
Total Deals	4
Total Value	$6,496,000
Average Sale Price	$1,624,000
Price Range	$975K - $2.6M

Neighborhoods Jen is Experienced In

North Chatham

1 Sale

Jen's Listings and Deals

Jen's Active Listings

$605,000
- 2 Beds
- 1 Bath
- 720 Sq Ft
15 Alice Rd

Eastham, MA
Cottage by the Bay! Here's your chance to own a true slice of Cape Cod on the beautiful bay side of Eastham — the kind of place where you drop your bags and head for the beach, under a mile away. This 1940 two-bedroom cottage was renovated in 2017, taken down to the studs and rebuilt with all-new insulation, plumbing, electrical, windows, roof, kitchen, and bath, all while preserving its original

Jen Whitaker Gibson Sotheby's International Realty

$2,150,000

Pending
- 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

Jen Whitaker Gibson Sotheby's International Realty

$1,900,000

Pending
- 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

Jen Whitaker Gibson Sotheby's International Realty

Recently Sold

$980,000

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

Brewster, MA
- 2% Above List
- 8 Days On Market
- $567/SF
- 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
- 8 Days On Market
- $1,007/SF
- Current Est. Value $427K
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
- 4 Days On Market
- $621/SF
- Current Est. Value $766K
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
- 30 Days On Market
- $567/SF
Jen Whitaker Gibson Sotheby's International Realty

Agent License: Massachusetts 448013754

Jen Whitaker

(508) 501-9092

(508) 501-9092

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