Darlene Winegardner Real Estate Agent - RE/MAX Executive

406 Holly Dr, Annapolis, MD Under Contract $430,000 - listed by Darlene Winegardner — Under Contract $430,000

Darlene Winegardner listing agent for 704 Cloverfields Dr, Stevensville, MD - sold for $490,000 — Sold $490,000

8890 Fairlee Rd, Chestertown, MD For Rent $2,500/month - listed by Darlene Winegardner — For Rent $2,500/month

101 Birch Rd, Stevensville, MD Pending $500,000 - listed by Darlene Winegardner — Pending $500,000

Darlene Winegardner buyer's agent for 914 Petinot Place, Stevensville, MD - sold for $374,000 — Sold $374,000

Darlene Winegardner

Chester MD

RE/MAX Executive

93 Closed Sales

$43.9M Total Value

$175K - $2.3M Price Range

$472.2K 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: Townhouse, House, Condo, Manufactured, Lot/Land, Other

Years of Experience: 26

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	7
Total Value	$3,988,000
Average Sale Price	$569,714
Price Range	$259K - $1.1M

Buyer Deals
Total Deals	2
Total Value	$699,000
Average Sale Price	$349,500
Price Range	$325K - $374K

Seller Deals
Total Deals	18
Total Value	$10,837,400
Average Sale Price	$602,078
Price Range	$250K - $1.3M

Buyer Deals
Total Deals	11
Total Value	$6,195,900
Average Sale Price	$563,264
Price Range	$175K - $2.3M

Seller Deals
Total Deals	44
Total Value	$22,539,800
Average Sale Price	$512,268
Price Range	$70K - $1.3M

Buyer Deals
Total Deals	49
Total Value	$21,370,999
Average Sale Price	$436,143
Price Range	$136K - $2.3M

5 Year View

Neighborhoods Darlene is Experienced In

Darlene's Active Listings

$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

$430,000
- 3 Beds
- 1.5 Baths
- 1,368 Sq Ft
406 Holly Dr

Annapolis, MD
Nestled in the highly sought-after Hillsmere community—one of Annapolis' premier waterfront neighborhoods—this charming home offers access to an exceptional array of amenities, including a private beach, boat ramp, community pool, playground, and more. This 3-bedroom, 1.5-bath residence features a full, partially finished basement, a spacious screened porch perfect for relaxing or entertaining,

Darlene Winegardner RE/MAX Executive

$500,000
- 4 Beds
- 3 Baths
- 2,464 Sq Ft
101 Birch Rd

Stevensville, MD
Beautiful Home with Finished Waterproofed Basement & Chesapeake Bay Water Access! Don't miss this exceptional home featuring a professionally waterproofed basement with a transferable warranty. The lower level offers a spacious recreation/living room, full bath, bedroom, and abundant storage space—perfect for guests, extended family, or a home office. You are first greeted by a cozy front porch

Darlene Winegardner RE/MAX Executive

$1,100,000
- 4 Beds
- 3 Baths
- 3,017 Sq Ft
2812 Harvest Ct

Chester, MD
Welcome to this pristine contemporary ranch in the coveted waterfront community of South Wind on Kent Island, where luxury, comfort, and resort-style living come together on 1.21 beautifully landscaped acres. From the moment you arrive, the home’s lush green lawn, vibrant gardens, and custom walkways create a picture-perfect setting worthy of a magazine cover. Inside, the open-concept floor plan

Darlene Winegardner RE/MAX Executive

$2,500 per month
- 3 Beds
- 2 Baths
- 1,232 Sq Ft
8890 Fairlee Rd

Chestertown, MD
Beautiful and clean ranch featuring open floor plan and separated primary bedroom. Adorable kitchen and dining area with slider to rear deck. laundry included

Darlene Winegardner RE/MAX Executive

Recently Sold

$650,000

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

Annapolis, MD
- $293/SF
- 430 Days On Market
- Current Est. Value $631K
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
- $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 $477K
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 $680K
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 $588K
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 $282K
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 $280K
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 $546K
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 $255K
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