Southwind

Southwind is a luxurious, waterfront community located in Chester, Maryland,

Community Profile

Life in Southwind

Welcome to Southwind

Southwind is a luxurious, waterfront community located in Chester, Maryland, on the Eastern Bay. Known for its expansive custom-built homes, Southwind features properties that offer stunning views of the bay and access to the water through private piers and docks. Homes in the community are typically large, with square footage ranging from 3,150 to over 6,000 square feet, offering 3 to 5 bedrooms and ample living space. The neighborhood provides residents with a peaceful, scenic lifestyle, perfect for boating enthusiasts and those seeking luxury living in a serene setting.

 

By the Numbers

Data based on information from Jan 1, 2020 to Jan 1, 2025

  • Average Sales Price: $1,095,000 - $2,050,000
  • Average Number of Annual Sales: 5
  • Average List-to-Sale Price Ratio: 96.6%
  • Average Days on Market: 95
  • Average Price Per Square Foot: $346
  • Average Bedrooms: 4
  • Average Bathrooms: 4

Highlights

  • Lifestyle: Estates, Water Access, Rural
  • Community Association: Mandatory
  • Community Amenities: Clubhouse, Tennis and Pickleball Courts, Trails, Boat Launch

Visit the Community Website
 

 

About the Area

Regional Background

The Eastern Shore is characterized by waterfront towns, agricultural landscapes, and a slower, more intentional pace of life. Buyers are often motivated by lifestyle considerations, privacy, and long-term ownership, including second-home purchasers and those seeking an alternative to more densely populated markets. Real estate activity in the region reflects a strong connection to place and a preference for quality over speed.

 

Lifestyle Pillars

Waterfront, Second-Home, Historic towns, Agriculture, Quiet luxury

Current Opportunities

Property Listings

Filter neighborhood properties
300 WOODS POINT ROAD
For Sale MLS® MDQA2017820

300 WOODS POINT ROAD

CHESTER, MD 21619

$2,840,000

5 BD 3.5 BA 1,704 Sq.Ft.
2702 SHERMAN DRIVE
Active Under Contract MLS® MDQA2017858

2702 SHERMAN DRIVE

CHESTER, MD 21619

$989,000

5 BD 3 BA 2,752 Sq.Ft.
215 KINGFISHER LANE
For Lease MLS® MDQA2018684

215 KINGFISHER LANE

CHESTER, MD 21619

$4,800

5 BD 4.5 BA 3,225 Sq.Ft.
1717 HARBOR DRIVE
For Sale MLS® MDQA2018534

1717 HARBOR DRIVE

CHESTER, MD 21619

$1,250,000

3 BD 2.5 BA 2,742 Sq.Ft.
402 MACUM CREEK DRIVE
Coming Soon MLS® MDQA2018418

402 MACUM CREEK DRIVE

CHESTER, MD 21619

$789,000

3 BD 2.5 BA 2,787 Sq.Ft.
330 SERENITY LANE
Pending MLS® MDQA2016472

330 SERENITY LANE

CHESTER, MD 21619

$5,400,000

7 BD 8 BA 10,667 Sq.Ft.
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Around the Community

Around Southwind, MD

There's plenty to do around Southwind, including shopping, dining, nightlife, parks, and more. Data provided by Walk Score and Yelp.

2
Car-Dependent
Walking Score
36
Somewhat Bikeable
Bike Score

Points of Interest

Explore popular things to do in the area, including C Legg's Seafood, Strongs Bay Seafood, and Papa Johns Pizza.

Name Category Distance Reviews
Ratings by Yelp
C Legg's Seafood Logo
Dining 0.37 miles 1 review 5/5 stars
Dining 0.48 miles 0 reviews 0/5 stars
Dining · $ 0.71 miles 10 reviews 1.9/5 stars
Charlies Chicken & Eats Logo
Dining 0.71 miles 4 reviews 4.8/5 stars
Stony Man Logo
Dining 0.71 miles 8 reviews 4.1/5 stars
Dining 0.93 miles 0 reviews 0/5 stars

Education & Local Resources

Schools in Southwind, MD

The following schools are within or nearby Southwind. The rating and statistics can serve as a starting point to make baseline comparisons on the right schools for your family. Data provided by the U.S. Census Bureau.
Type
Name
Category
Grades
School Rating

Southwind, MD

By the Numbers

Population Households Employment

Southwind has 2,441 households, with an average household size of 2.41. Data provided by the U.S. Census Bureau. Here’s what the people living in Southwind do for work — and how long it takes them to get there. Data provided by the U.S. Census Bureau. 5,905 people call Southwind home. The population density is 636 and the largest age group is Data provided by the U.S. Census Bureau.

5,905

Total Population

High

Population Density Population Density This is the number of people per square mile in a neighborhood.

46.3 years

Median Age

50 / 50%

Men vs Women

Population by Age Group

0-9:

10.5%

0-9 Years

10-17:

8.7%

10-17 Years

18-24:

5.9%

18-24 Years

25-64:

53.6%

25-64 Years

65-74:

12.8%

65-74 Years

75+:

8.6%

75+ Years

Education Level

  • Less Than 9th Grade
  • High School Degree
  • Associate Degree
  • Bachelor Degree
  • Graduate Degree
2,441

Total Households

2.41

Average Household Size

$63,189

Average individual Income

Households with Children

With Children:

Without Children:

Marital Status

Married
Single
Divorced
Separated

Blue vs White Collar Workers

Blue Collar:

White Collar:

Commute Time

0 to 14 Minutes
15 to 29 Minutes
30 to 59 Minutes
60+ Minutes

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CONTACT the HOUSECATS company

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Contact Details

The HOUSECATS COMPANY
Phone: (410) 991-1382
Email: [email protected]
COMPASS REAL ESTATE
Phone: (410) 429-7425
Address 2077 SOMERVILLE RD, SUITE 200, Annapolis, MD 21401

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