Chestertown Area Waterfront Homes for Sale

• All Listings
• 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

Save Search

Sort by:

Price, high to low

New Open House

$3,375,000

1451 Cola Dr, MCLEAN

6 Beds 7 Baths 8,083 SqFt Residential MLS® # VAFX2344860

Keller Williams Realty

Open House

$3,375,000

25 Sandringham Rd, BALA CYNWYD

6 Beds 6 Baths 6,743 SqFt Residential MLS® # PAMC2182976

RE/MAX Professional Realty

Open House

$3,350,000

2 E 47th St, LONG BEACH TOWNSHIP

5 Beds 5 Baths 3,461 SqFt Residential

Open House

Sat, Oct 10th, 2026 @ 12pm - 2pm

MLS® # NJOC2045422

BHHS Zack Shore REALTORS

$3,350,000

1493 John Tyler Memorial Hwy, WILLIAMSBURG

5 Beds 4.5 Baths 5,367 SqFt Residential MLS® # VAJC2000728

Howard Hanna Real Estate Services

$3,350,000

9223 Elk Run Rd, CATLETT

0 Beds 0 Baths 456,944 SqFt Commercial Sale MLS® # VAFQ2012740

EXIT Realty Pros

Open House

$3,300,000

13442 Loyalty Rd, LEESBURG

5 Beds 7 Baths 9,172 SqFt Residential

Open House

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

MLS® # VALO2136460

Hunt Country Sotheby's International Realty

$3,299,999

19 Bayard Street Ext, FENWICK ISLAND

4 Beds 3.5 Baths 3,500 SqFt Residential MLS® # DESU2103900

JOHN KLEINSTUBER AND ASSOC INC

Open House

$3,299,000

242 N 8th St, SURF CITY

4 Beds 4.5 Baths 3,065 SqFt Residential

Open House

Sat, Oct 10th, 2026 @ 10am - 12pm

MLS® # NJOC2044750

BHHS Zack Shore REALTORS

$3,295,000

113-115 Arch St #penthouse 2, PHILADELPHIA

4 Beds 3.5 Baths 3,556 SqFt Residential MLS® # PAPH2612844

Compass Pennsylvania, LLC

New Open House

$3,258,888

2101 Grayson Pl, FALLS CHURCH

7 Beds 7.5 Baths 9,659 SqFt Residential MLS® # VAFX2344940

Innovation Properties, LLC

Open House

$3,250,000

142 Torquay Ct, REHOBOTH BEACH

6 Beds 4 Baths 4,500 SqFt Residential

Open House

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

MLS® # DESU2119096

Monument Sotheby's International Realty

$3,238,888

7601 Maryknoll Ave, BETHESDA

7 Beds 7.5 Baths 7,142 SqFt Residential MLS® # MDMC2231174

Rory S. Coakley Realty, Inc.

New

$3,200,000

5013 Chalk Point Rd, WEST RIVER

4 Beds 2 Baths 1,232 SqFt Residential MLS® # MDAA2158318

RE/MAX Executive

New

$3,200,000

5011 Chalk Point Rd, WEST RIVER

3 Beds 1 Bath 2,322 SqFt Residential MLS® # MDAA2158254

RE/MAX Executive

$3,200,000

↓ $2,591,250

Lot 3 (principal Lot And Rural Economy Lot), LEESBURG

0 Beds 0 Baths 0 SqFt Land MLS® # VALO2132098

Pearson Smith Realty, LLC

New

$3,150,000

28041 Old Country Club Rd, EASTON

5 Beds 5 Baths 4,478 SqFt Residential MLS® # MDTA2015318

TTR Sotheby's International Realty

Open House

$3,149,000

2209 18th St N, ARLINGTON

5 Beds 5.5 Baths 5,272 SqFt Residential

Open House

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

MLS® # VAAR2079506

TTR Sotheby's International Realty

Open House

$3,049,000

48 11th St N #48, SURF CITY

4 Beds 4.5 Baths 2,812 SqFt Residential

Open House

Fri, Oct 9th, 2026 @ 3pm - 5pm

MLS® # NJOC2045128

BHHS Zack Shore REALTORS

Prev

1 2 3 4 5 6 7 420

Next