Darlene Winegardner

Chester MD

RE/MAX Executive

100 Closed Sales

$48.1M Total Value

$189.9K - $2.3M Price Range

$480.7K Average Price

Prior 5 years

About Darlene

Full-time local agent for over 21 years serving the Chesapeake Bay region. Specializing in meeting your needs whether your needs are to find your dream home or sell your home. Darlene's staging and furnishings will sell your home fast and for more! Some homes have even sold for thousands over list price!!

Home Types: House, Townhouse, Condo, Lot/Land, Manufactured, Other

Years of Experience: 26

Transaction History

1 Year
2 Year
5 Year

Seller Deals

Total Deals

Total Value

$3,808,000

Average Sale Price

$544,000

Price Range

$259K - $1.1M

Buyer Deals

Total Deals

Total Value

$699,000

Average Sale Price

$349,500

Price Range

$325K - $374K

Seller Deals

Total Deals

Total Value

$10,642,400

Average Sale Price

$591,244

Price Range

$250K - $1.3M

Buyer Deals

Total Deals

Total Value

$8,472,900

Average Sale Price

$605,207

Price Range

$175K - $2.3M

Seller Deals

Total Deals

Total Value

$24,217,800

Average Sale Price

$504,538

Price Range

$70K - $1.3M

Buyer Deals

Total Deals

Total Value

$23,855,574

Average Sale Price

$458,761

Price Range

$136K - $2.3M

5 Year View

Neighborhoods Darlene is Experienced In

Darlene's Active Listings

$444,900
- 6 Beds
- 2 Baths
- 2,486 Sq Ft
100 Wall St

Queenstown, MD
Seller has found a property out of state, so all reasonable offers will be considered...Step back in time—without sacrificing a single modern comfort—in this colonial masterpiece, where historic elegance and thoughtful renovations come together in perfect harmony. Nestled in the picturesque and walkable heart of Queenstown, this 6-bedroom, 2-bath showstopper is more than just a home—it's an

Darlene Winegardner RE/MAX Executive

$85,000
- Land
- 0.95 Acre
- $89,474 per Acre
Parcel 104 Pfalzgroff Rd

Millington, MD
Just Listed! Build your Dream Home! This is a beautiful lot sited on almost 1 acre and is perfect for your home! Mostly cleared and backs to trees. Located just 2 minutes from Route 301 and 5 minutes from the heart of Millington and Crumpton, this home combines tranquility with accessibility. 205 Pfalzgroff Rd, the home next door, is also available for sale...ideal for expansion, investment, or

Darlene Winegardner RE/MAX Executive

$439,900
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
1340 Queen Anne Dr

Chester, MD
PRICE Improvement...Discover the charm of this fully updated ranch in a serene, water-privileged community! With a spacious yard and an inviting open floor plan, this home features a stunning new kitchen complete with a large white granite island, sleek white cabinets, and stainless steel appliances. Sunlight floods the dining area through new sliding doors, while the generous living room is

Darlene Winegardner RE/MAX Executive

$650,000
- 3 Beds
- 2 Baths
- 2,218 Sq Ft
1165 Green Holly Ct

Annapolis, MD
Cape St. Claire Home sold with Extra Lot included! This lovely Cape St. Claire property boasts an extra lot, offering more space for your family to enjoy. Build a detached garage with extra living space or possible ADU. Upon entering the home, you’ll immediately feel at ease. The spacious living room, which could also serve as a formal dining area, features a cozy fireplace. The kitchen, with its

Darlene Winegardner RE/MAX Executive

Recently Sold

$1,050,000 Sold May 12, 2026
- 4 Beds
- 2 Baths
- 1,809 Sq Ft
2762 Bon Haven Ln

Annapolis, MD
- 9% Below List
- $580/SF
- 76 Days On Market
- Current Est. Value $1M
Darlene Winegardner RE/MAX Executive

$490,000 Sold Apr 16, 2026
- 1 Bed
- 4 Baths
- 1,496 Sq Ft
704 Cloverfields Dr

Stevensville, MD
- 1% Above List
- $328/SF
- 21 Days On Market
- Current Est. Value $479K
Darlene Winegardner RE/MAX Executive

$670,000 Sold Nov 17, 2025
- 5 Beds
- 3.5 Baths
- 3,268 Sq Ft
717 Cloverfields Dr

Stevensville, MD
- $205/SF
- 73 Days On Market
- Current Est. Value $683K
Darlene Winegardner RE/MAX Executive

$590,000 Sold Nov 7, 2025
- 3 Beds
- 2 Baths
- 2,000 Sq Ft
504 Main St

Stevensville, MD
- $295/SF
- 11 Days On Market
- Current Est. Value $587K
Darlene Winegardner RE/MAX Executive

$279,000 Sold Sep 11, 2025
- 3 Beds
- 1 Bath
- 1,082 Sq Ft
205 Pfalzgroff Rd

Millington, MD
- $258/SF
- 61 Days On Market
- Current Est. Value $286K
Darlene Winegardner RE/MAX Executive

$259,000 Sold Jul 24, 2025
- 3 Beds
- 1 Bath
- 960 Sq Ft
107 Lee Rd

Chester, MD
- $270/SF
- 160 Days On Market
- Current Est. Value $272K
Darlene Winegardner RE/MAX Executive

$470,000 Sold Jun 13, 2025
- 3 Beds
- 2.5 Baths
- 2,277 Sq Ft
107 Bayview

Grasonville, MD
- $206/SF
- 159 Days On Market
- Current Est. Value $529K
Darlene Winegardner RE/MAX Executive

$250,000 Sold Feb 26, 2025
- 4 Beds
- 2 Baths
- 1,536 Sq Ft
201 S 2nd St

Denton, MD
- $163/SF
- 135 Days On Market
- Current Est. Value $263K
Darlene Winegardner RE/MAX Executive

$290,000 Sold Feb 7, 2025
- 4 Beds
- 2 Baths
- 1,782 Sq Ft
206 Price Rd

Chester, MD
- $163/SF
- 116 Days On Market
Darlene Winegardner RE/MAX Executive

Awards and Designations

CRS - Certified Residential Specialist

Agent License: Maryland 509819

Darlene Winegardner

(443) 214-3465

Homes for Sale by City

Darlene Winegardner

About Darlene

Transaction History

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Neighborhoods Darlene is Experienced In

Darlene's Listings and Deals

Darlene's Active Listings

Recently Sold

Awards and Designations