Penny Windsor Real Estate Agent - Benson & Mangold, LLC

3908 Lee Ct, East New Market, MD For Sale $159,500 - listed by Penny Windsor — For Sale $159,500

Penny Windsor listing agent for 314 Muir St, Cambridge, MD - sold for $76,500 — Sold $76,500

1104 Locust St, Cambridge, MD For Sale $86,000 - listed by Penny Windsor — For Sale $86,000

Penny Windsor buyer's agent for 6315 E New Market Ellwood Rd, Hurlock, MD - sold for $299,900 — Sold $299,900

314 Glenburn Ave, Cambridge, MD For Sale $325,000 - listed by Penny Windsor — For Sale $325,000

Penny Windsor

Cambridge MD

Benson & Mangold, LLC

50 Closed Sales

$15.4M Total Value

$40K - $1.7M Price Range

$307.7K Average Price

Prior 5 years

About Penny

Penny received her AA degree from Chesapeake College in Business Administration and a Certificate from the University of Georgia in Nutrition and Food Service Management. She has owned and operated Windsor Trucking Company since 1989. She worked for Harrison House in Georgetown, Delaware as Food Service Director for 14 years. She also owned a successful retail store, The Hen House Country Store, in Hurlock.

Penny started her real estate career in 2009 and has been very successful. She served on the Mid Shore Board of Realtors as a Director from 2010 to 2013. In 2012 she was Rookie Realtor of the Year for top sales for agents with less than four years’ experience. In 2013, she was one of the top producing agents in Dorchester County.

She attends Friendship United Methodist Church and enjoys exercising, gardening, traveling and community involvement.

Home Types: House, Condo, Lot/Land, Mobile Homes, Commercial, Townhouse, Multifamily

Years of Experience: 17

Education: Chesapeake College University of Georgia

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	9
Total Value	$4,069,900
Average Sale Price	$452,211
Price Range	$77K - $1.3M

Buyer Deals
Total Deals	4
Total Value	$2,091,400
Average Sale Price	$522,850
Price Range	$217K - $1.2M

Seller Deals
Total Deals	13
Total Value	$6,512,400
Average Sale Price	$500,954
Price Range	$40K - $1.7M

Buyer Deals
Total Deals	8
Total Value	$3,391,400
Average Sale Price	$423,925
Price Range	$140K - $1.2M

Seller Deals
Total Deals	33
Total Value	$10,454,731
Average Sale Price	$316,810
Price Range	$40K - $1.7M

Buyer Deals
Total Deals	17
Total Value	$4,930,300
Average Sale Price	$290,018
Price Range	$60K - $1.2M

5 Year View

Areas Penny is Experienced In

Penny's Listings and Deals

Penny's Active Listings

$159,500
- 3 Beds
- 2 Baths
- 1,386 Sq Ft
3908 Lee Ct

East New Market, MD
Welcome to Heritage Estates Mobile Home Community. This beautiful 1,386 Sq ft manufactured home offers 3-bedrooms 2 full baths, large bright living room, dining area with sliding glass doors. Primary full bath with walk-in closet, double sinks standup shower. 2nd and 3rd bedrooms have walk-in closets. This exceptional home is nestled in the community of Heritage Estates, one of the most beautiful

Penny Windsor Benson & Mangold, LLC

$86,000
- 3 Beds
- 1.5 Baths
- 1,900 Sq Ft
1104 Locust St

Cambridge, MD
Location, location, location!! Bring your dreams and visions to life restoring this 1,900 sq ft home in the heart of Cambridge. This home is walking distance to all Cambridge has to offer. Downtown shopping, pubs, restaurants, churches, post office, library, banks. The home offers 3 bedrooms, 1.5 bathrooms, large kitchen with breakfast area, laundry room and half bath, living room with wood

Penny Windsor Benson & Mangold, LLC

$325,000
- 3 Beds
- 1 Bath
- 1,408 Sq Ft
314 Glenburn Ave

Cambridge, MD
Cozy all brick Colonial in highly sought out historic West End. Glenburn Ave is one of Cambridge's most beautiful historic streets. The home is located on a corner lot just 2 blocks from the Choptank River, parks and boat ramp. It is walking distance to downtown shops, restaurants, churches, schools, banks and the YMCA. This 1,408 st. ft. home has 1 bedroom, gally kitchen, dining room, laundry

Penny Windsor Benson & Mangold, LLC

$319,500
- 4 Beds
- 2.5 Baths
- 2,032 Sq Ft
405 Osprey Cir

Cambridge, MD
Well maintained home in Blackwater Landing. Home offers 4 bedrooms, 2.5 baths. Formal dining room, Den, Breakfast area, large family room, kitchen with center island and 2 car garage. If the stairs are a problem the home is equipped with a chairlift to the second floor and can be easily removed if not needed. Home is in a mature neighborhood with new construction. Close to schools, shopping and

Penny Windsor Benson & Mangold, LLC

$405,000

Under Contract
- 3 Beds
- 2 Baths
- 1,618 Sq Ft
5841 Hudson Wharf Rd

Cambridge, MD
Updated 3-bedroom, 2-bath waterfront home on Hudson Creek offers breathtaking water views. Enjoy crabbing, fishing and boating from your very own Hudson Creek oasis. New 90 ft private pier with 10x20 sun deck and 2 boat slips. Enjoy the large yard, rear screened-in porch, waterside gazebo. Features include a 2-car garage, paved driveway, and ideal spaces for relaxation and entertaining. New well,

Penny Windsor Benson & Mangold, LLC

Recently Sold

$260,000

Sold Jun 1, 2026
- 4 Beds
- 2 Baths
- 1,664 Sq Ft
6539 Cabin Ridge Rd

Hurlock, MD
- 12% Below List
- 106 Days On Market
- $156/SF
Penny Windsor Benson & Mangold, LLC

$76,500

Sold May 22, 2026
- 3 Beds
- 1.5 Baths
- 1,796 Sq Ft
314 Muir St

Cambridge, MD
- 4% Below List
- 3 Days On Market
- $43/SF
- Current Est. Value $80K
Penny Windsor Benson & Mangold, LLC

$371,000

Sold May 18, 2026
- 3 Beds
- 3.5 Baths
- 2,352 Sq Ft
7012 Scotch Dr

Laurel, MD
- 3% Above List
- 14 Days On Market
- $158/SF
- Current Est. Value $368K
Penny Windsor Benson & Mangold, LLC

$297,500

Sold Apr 30, 2026
- 4 Beds
- 2.5 Baths
- 1,906 Sq Ft
103 Night Heron Ct

Cambridge, MD
- 10% Below List
- 25 Days On Market
- $156/SF
- Current Est. Value $286K
Penny Windsor Benson & Mangold, LLC

$304,000

Sold Feb 11, 2026
- 3 Beds
- 2 Baths
- 1,232 Sq Ft
103 Linden Ave

Secretary, MD
- 175 Days On Market
- $247/SF
- Current Est. Value $300K
Penny Windsor Benson & Mangold, LLC

$585,900

Sold Jan 9, 2026
- 5 Beds
- 3 Baths
- 2,116 Sq Ft
3 Ackerman Ct

Stevensville, MD
- 155 Days On Market
- $277/SF
- Current Est. Value $570K
Penny Windsor Benson & Mangold, LLC

$590,000

Sold Jan 9, 2026
- 3 Beds
- 3 Baths
- 2,565 Sq Ft
8197 Detour Rd

Denton, MD
- 250 Days On Market
- $230/SF
- Current Est. Value $593K
Penny Windsor Benson & Mangold, LLC

$295,000

Sold Dec 15, 2025
- 3 Beds
- 2 Baths
- 1,536 Sq Ft
6271 Solomons Cir

Hurlock, MD
- 168 Days On Market
- $192/SF
- Current Est. Value $312K
Penny Windsor Benson & Mangold, LLC

$1,290,000

Sold Dec 1, 2025
- 4 Beds
- 3 Baths
- 4,445 Sq Ft
4906 Timbermarsh Ln

Woolford, MD
- 159 Days On Market
- $290/SF
- Current Est. Value $1M
Penny Windsor Benson & Mangold, LLC

Agent License: Maryland 634648

Penny Windsor

(667) 243-8567

Nearby Homes

Penny Windsor

About Penny

Transaction History

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Areas Penny is Experienced In

Penny's Listings and Deals

Penny's Active Listings

Recently Sold