Darlene Winegardner Real Estate Agent - RE/MAX Executive

2006 Bennett Point Rd, Queenstown, MD For Sale $1,500,000 - listed by Darlene Winegardner — For Sale $1,500,000

Darlene Winegardner listing agent for 406 Holly Dr, Annapolis, MD - sold for $420,000 — Sold $420,000

1340 Queen Anne Dr, Chester, MD For Rent $2,700/month - listed by Darlene Winegardner — For Rent $2,700/month

509 Teal Ct, Chester, MD Under Contract $300,000 - listed by Darlene Winegardner — Under Contract $300,000

Darlene Winegardner buyer's agent for 108 Claiborne Fields Dr, Centreville, MD - sold for $627,000 — Sold $627,000

Darlene Winegardner

Chester MD

RE/MAX Executive

93 Closed Sales

$44.9M Total Value

$193K - $2.3M Price Range

$483.1K 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, Mobile Homes, Lot/Land, Other

Years of Experience: 26

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	10
Total Value	$6,043,000
Average Sale Price	$604,300
Price Range	$259K - $1.1M

Buyer Deals
Total Deals	3
Total Value	$1,326,000
Average Sale Price	$442,000
Price Range	$325K - $627K

Seller Deals
Total Deals	21
Total Value	$12,892,400
Average Sale Price	$613,924
Price Range	$250K - $1.3M

Buyer Deals
Total Deals	12
Total Value	$6,822,900
Average Sale Price	$568,575
Price Range	$175K - $2.3M

Seller Deals
Total Deals	46
Total Value	$23,719,800
Average Sale Price	$515,648
Price Range	$70K - $1.3M

Buyer Deals
Total Deals	47
Total Value	$21,210,099
Average Sale Price	$451,279
Price Range	$136K - $2.3M

5 Year View

Areas Darlene is Experienced In

Darlene's Listings and Deals

Darlene's Active Listings

$1,500,000
- 4 Beds
- 3 Baths
- 2,721 Sq Ft
2006 Bennett Point Rd

Queenstown, MD
Spectacular Waterfront Retreat on almost 7 Acres in Exclusive Bennett Point!Welcome to your private paradise on the shores of serene Greenwood Creek! This extraordinary waterfront estate offers almost 7 acres of pure tranquility and luxury, surrounded by water on two sides for a true feeling of seclusion and peace.Your deep-water private pier is a boater’s dream — complete with 3

Darlene Winegardner RE/MAX Executive

$424,990
- 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
Perc Approved! 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.

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

$300,000

Under Contract
- 2 Beds
- 2 Baths
- 1,100 Sq Ft
509 Teal Ct

Chester, MD
Welcome to your perfect island retreat in the sought-after waterfront community of Bayside! This beautifully positioned end-unit condominium offers the ideal blend of comfort, convenience, and breathtaking scenery. Enjoy tranquil pond views with a charming fountain, along with glimpses of the Chester River and marina—all from the privacy of your own deck. Whether you're sipping your morning

Darlene Winegardner RE/MAX Executive

$2,700 per month
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
1340 Queen Anne Dr

Chester, MD
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 accented with stylish

Darlene Winegardner RE/MAX Executive

Recently Sold

$420,000

Sold Aug 14, 2026
- 3 Beds
- 1.5 Baths
- 1,368 Sq Ft
406 Holly Dr

Annapolis, MD
- 16% Below List
- 15 Days On Market
- $307/SF
- Current Est. Value $496K
Darlene Winegardner RE/MAX Executive

$1,125,000

Sold Aug 3, 2026
- 4 Beds
- 3 Baths
- 3,017 Sq Ft
2812 Harvest Ct

Chester, MD
- 2% Above List
- 4 Days On Market
- $373/SF
- Current Est. Value $1M
Darlene Winegardner RE/MAX Executive

$510,000

Sold Jul 31, 2026
- 4 Beds
- 3 Baths
- 2,464 Sq Ft
101 Birch Rd

Stevensville, MD
- 2% Above List
- 2 Days On Market
- $207/SF
- Current Est. Value $499K
Darlene Winegardner RE/MAX Executive

$650,000

Sold Jun 4, 2026
- 3 Beds
- 2 Baths
- 2,218 Sq Ft
1165 Green Holly Ct

Annapolis, MD
- 430 Days On Market
- $293/SF
- Current Est. Value $658K
Darlene Winegardner RE/MAX Executive

$1,050,000

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

Annapolis, MD
- 9% Below List
- 76 Days On Market
- $580/SF
- 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
- 21 Days On Market
- $328/SF
- 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
- 73 Days On Market
- $205/SF
- Current Est. Value $675K
Darlene Winegardner RE/MAX Executive

$590,000

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

Stevensville, MD
- 11 Days On Market
- $295/SF
- Current Est. Value $585K
Darlene Winegardner RE/MAX Executive

$279,000

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

Millington, MD
- 61 Days On Market
- $258/SF
- Current Est. Value $281K
Darlene Winegardner RE/MAX Executive

Awards and Designations

CRS - Certified Residential Specialist

Agent License: Maryland 509819

Darlene Winegardner

(443) 214-3465

Nearby Homes

Darlene Winegardner

About Darlene

Transaction History

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Areas Darlene is Experienced In

Darlene's Listings and Deals

Darlene's Active Listings

Recently Sold

Awards and Designations