Chestertown Area Waterfront Homes for Sale, $300,000 - $400,000

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• Under $100,000
• $100,000 - $200,000
• $200,000 - $300,000
• $300,000 - $400,000
• $400,000 - $500,000
• $500,000 - $600,000
• $600,000 - $700,000
• $700,000 - $800,000
• $800,000 - $900,000
• $900,000 - $1,000,000
• Over $1,000,000

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$1,499,900

43446 Freeport, STERLING

4 Beds 4.5 Baths 5,731 SqFt Residential MLS® # VALO2136066

EXP Realty, LLC

Open House

$1,499,900

3705 Linda Ln, ANNANDALE

5 Beds 4.5 Baths 5,552 SqFt Residential

Open House

Sun, Oct 11th, 2026 @ 1pm - 3pm

MLS® # VAFX2338846

Samson Properties

$1,499,900

1303 Coastal Hwy, FENWICK ISLAND

0 Beds 0 Baths 0 SqFt Land MLS® # DESU2115042

JOHN KLEINSTUBER AND ASSOC INC

Open House

$1,499,900

733 Euclid St Nw #303, WASHINGTON

4 Beds 4 Baths 2,960 SqFt Residential

Open House

Sat, Oct 10th, 2026 @ 2pm - 4pm

MLS® # DCDC2264278

TTR Sotheby's International Realty

Open House

$1,499,500

4821 Montgomery Ln #206, BETHESDA

2 Beds 2.5 Baths 1,803 SqFt Residential

Open House

Sat, Oct 10th, 2026 @ 2pm - 4pm

MLS® # MDMC2255924

Compass

New

$1,499,000

1385 Bishop Crest Ct, ALEXANDRIA

5 Beds 4.5 Baths 4,386 SqFt Residential MLS® # VAFX2345354

TTR Sotheby's International Realty

New Open House

$1,499,000

5901 Cromwell Dr, BETHESDA

5 Beds 3 Baths 3,300 SqFt Residential

Open House

Sun, Oct 11th, 2026 @ 1pm - 3pm

MLS® # MDMC2259128

Washington Fine Properties, LLC

New Open House

$1,499,000

963 N Rochester St, ARLINGTON

4 Beds 3 Baths 2,544 SqFt Residential MLS® # VAAR2080512

Corcoran McEnearney

Open House

$1,499,000

103a E Oxford Ave, ALEXANDRIA

4 Beds 3.5 Baths 2,012 SqFt Residential

Open House

Sat, Oct 10th, 2026 @ 12pm - 1:30pm

MLS® # VAAX2066924

Compass

New

$1,499,000

8313 Ivy Green Rd, FAIRFAX STATION

7 Beds 5.5 Baths 6,120 SqFt Residential MLS® # VAFX2342856

TTR Sotheby's International Realty

New

$1,499,000

779 Shavertown Rd, GARNET VALLEY

4 Beds 3.5 Baths 3,800 SqFt Residential MLS® # PADE2122968

United Real Estate

$1,499,000

↓ $80,000

1434 Corcoran St Nw, WASHINGTON

0 Beds 0 Baths 2,520 SqFt Multi-Family MLS® # DCDC2279278

TTR Sotheby's International Realty

$1,499,000

↓ $80,000

1434 Corcoran St Nw, WASHINGTON

4 Beds 3.5 Baths 2,520 SqFt Residential MLS® # DCDC2279268

TTR Sotheby's International Realty

New

$1,499,000

151 N Main St, NEW HOPE

3 Beds 3 Baths 1,746 SqFt Residential MLS® # PABU2126784

BHHS Fox & Roach-New Hope

Open House

$1,499,000

1430 Swann St Nw, WASHINGTON

3 Beds 3.5 Baths 2,199 SqFt Residential

Open House

Sun, Oct 11th, 2026 @ 2pm - 4pm

MLS® # DCDC2265922

Realty ONE Group Capital

$1,499,000

↓ $101,000

14121 Caine Stable Rd, OCEAN CITY

4 Beds 3 Baths 2,044 SqFt Residential MLS® # MDWO2038428

Realty Plus Associates

$1,499,000

1903 Kalorama Rd Nw, WASHINGTON

4 Beds 4 Baths 4,192 SqFt Residential MLS® # DCDC2255966

Samson Properties

$1,495,900

8130 Hillcrest Dr, MANASSAS

5 Beds 5.5 Baths 4,805 SqFt Residential MLS® # VAPW2124892

Fairfax Realty Select

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