Chester MD Luxury Homes

71 results

$1,400,000
5 bds
5 ba
3,225 sqft
New construction
111 Flycatcher Way, Chester, MD 21619
K. Hovnanian Homes, KOVO REALTY
Inviting fireplace
$1,400,000
3 bds
4 ba
2,930 sqft
New construction
117 Flycatcher Way, Chester, MD 21619
K. Hovnanian Homes, KOVO REALTY
Cozy fireplace
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$1,300,000
3 bds
3 ba
2,789 sqft
New construction
123 Flycatcher Way, Chester, MD 21619
K. Hovnanian Homes, KOVO REALTY
Inviting fireplace
$1,167,890
4 bds
4 ba
-- sqft
New construction
1757 Harbor Dr, Chester, MD 21619
Lacrosse Homes, KELLER WILLIAMS FLAGSHIP
Rec room area
$1,100,000
3 bds
3 ba
1,830 sqft
House for sale
1704 Bayside Dr, Chester, MD 21619
COTTAGE STREET REALTY LLC
Elegant interior updates
$1,100,000
2 bds
2 ba
1,993 sqft
New construction
127 Flycatcher Way, Chester, MD 21619
K. Hovnanian Homes, KOVO REALTY
Cozy fireplace
$1,099,900
5 bds
4 ba
3,036 sqft
New construction
203 Riverside Dr, Chester, MD 21619
Laine Street Homes, LONG & FOSTER REAL ESTATE, INC.
Waterfront home
$999,990
2 bds
3 ba
1,900 sqft
New construction
176 Flagstaff Way Unit 43, Chester, MD 21619
K Hovnanian's Four Seasons
Price cut: $22,000 (2/3)
$999,900
2 bds
3 ba
1,900 sqft
New construction
176 Flagstaff Way #2443, Chester, MD 21619
K. Hovnanian Homes, KOVO REALTY
Price cut: $22,090 (2/2)
$995,000
5 bds
4 ba
2,496 sqft
House for sale
2613 Cecil Dr, Chester, MD 21619
BENSON & MANGOLD, LLC
Open: Sat 10am-12pm (3/7)
$949,990
5 bds
5 ba
3,225 sqft
New construction
311 Kingfisher Ln, Chester, MD 21619
K. Hovnanian Homes, KOVO REALTY
Price cut: $15,000 (2/13)
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$911,990+
4 bds
4 ba
3,512 sqft
New construction
Mykonos Plan, K. Hovnanian's® Four Seasons at Kent Island - Single Family
K Hovnanian's Four Seasons
Oversized walk-in closet
$908,990+
4 bds
4 ba
3,601 sqft
New construction
Munich ESP Plan, K. Hovnanian's® Four Seasons at Kent Island - Single Family
K Hovnanian's Four Seasons
Price increase: $25,000 (2/27)
$899,990
5 bds
5 ba
3,225 sqft
New construction
110 Kinglet Ct, Chester, MD 21619
K. Hovnanian Homes, KOVO REALTY
Price cut: $50,000 (2/18)
$899,990
3 bds
3 ba
2,602 sqft
New construction
110 Boatswain Way Unit 31, Chester, MD 21619
K Hovnanian's Four Seasons
Price cut: $30,000 (2/18)
$883,990+
3 bds
4 ba
2,930 sqft
New construction
Franklin Plan, K. Hovnanian's® Four Seasons at Kent Island - Single Family
K Hovnanian's Four Seasons
Slider to covered patio
$872,990+
5 bds
5 ba
3,225 sqft
New construction
Tuscaloosa Plan, K. Hovnanian's® Four Seasons at Kent Island - Single Family
K Hovnanian's Four Seasons
Resort-style pool
$849,990
2 bds
3 ba
1,900 sqft
New construction
176 Flagstaff Way #2433, Chester, MD 21619
K. Hovnanian Homes, KOVO REALTY
Price cut: $20,000 (2/2)
$849,990
2 bds
3 ba
1,900 sqft
New construction
176 Flagstaff Way Unit 33, Chester, MD 21619
K Hovnanian's Four Seasons
Price cut: $20,000 (2/3)
$843,990+
3 bds
3 ba
2,789 sqft
New construction
Kerr Plan, K. Hovnanian's® Four Seasons at Kent Island - Single Family
K Hovnanian's Four Seasons
Resort-style pool
$814,900
3 bds
3 ba
2,399 sqft
House for sale
135 Nauset Ln, Chester, MD 21619
REAL BROKER, LLC - ANNAPOLIS
Bonus loft space
$799,990
3 bds
3 ba
2,602 sqft
New construction
110 Boatswain Way Unit 21, Chester, MD 21619
K Hovnanian's Four Seasons
Price cut: $30,000 (2/18)
$798,990+
2 bds
2 ba
2,143 sqft
New construction
Kelly Plan, K. Hovnanian's® Four Seasons at Kent Island - Single Family
K Hovnanian's Four Seasons
Resort-style pool
$776,990+
2 bds
3 ba
2,010 sqft
New construction
Taylor Plan, K. Hovnanian's® Four Seasons at Kent Island - Single Family
K Hovnanian's Four Seasons
Resort-style pool
$769,990
2 bds
3 ba
1,900 sqft
New construction
110 Boatswain Way Unit 32, Chester, MD 21619
K Hovnanian's Four Seasons
Price cut: $21,000 (2/18)
$769,990
2 bds
3 ba
1,900 sqft
New construction
110 Boatswain Way Unit 33, Chester, MD 21619
K Hovnanian's Four Seasons
Price cut: $20,000 (2/18)
$769,500
5 bds
4 ba
3,250 sqft
House for sale
1868 Roberta Dr, Chester, MD 21619
COLDWELL BANKER REALTY
Open: Sun 12-2pm (3/8)
$764,900
3 bds
2 ba
2,303 sqft
Coming soon
129 Sailcloth Way, Chester, MD 21619
RE/MAX EXECUTIVE
On Market Mar 08
$750,000
4 bds
3 ba
2,870 sqft
Coming soon
266 Peregrine Dr, Chester, MD 21619
RE/MAX EXECUTIVE
On Market Mar 15
$725,990+
4 bds
3 ba
2,791 sqft
New construction
Simone Plan, K. Hovnanian's® Four Seasons at Kent Island - Single Family
K Hovnanian's Four Seasons
Resort-style pool
$694,500
3 bds
3 ba
2,602 sqft
Coming soon
230 Switchgrass Way Unit 21, Chester, MD 21619
LONG & FOSTER REAL ESTATE, INC.
On Market Mar 07
$693,990+
2 bds
2 ba
1,993 sqft
New construction
Jenkins II Plan, K. Hovnanian's® Four Seasons at Kent Island - Single Family
K Hovnanian's Four Seasons
Resort-style pool
$679,990
2 bds
3 ba
2,003 sqft
New construction
176 Flagstaff Way #2412, Chester, MD 21619
K. Hovnanian Homes, KOVO REALTY
Price cut: $20,000 (2/2)
$679,990
2 bds
3 ba
2,003 sqft
New construction
176 Flagstaff Way Unit 12, Chester, MD 21619
K Hovnanian's Four Seasons
Price cut: $20,000 (2/3)
$669,900
3 bds
3 ba
2,600 sqft
Condo for sale
200 Harrier Way #21, Chester, MD 21619
LONG & FOSTER REAL ESTATE, INC.
Price cut: $5,000 (3/2)
$660,990+
2 bds
2 ba
1,690 sqft
New construction
Bernstein II Plan, K. Hovnanian's® Four Seasons at Kent Island - Single Family
K Hovnanian's Four Seasons
Oversized island
$649,000
2 bds
2 ba
1,913 sqft
Coming soon
219 Broadwater Dr, Chester, MD 21619
RE/MAX EXECUTIVE
On Market Mar 09
$584,990+
3 bds
3 ba
2,602 sqft
New construction
Severn Plan, K. Hovnanian's® Four Seasons at Kent Island - Luxury Condos
K Hovnanian's Four Seasons
Price cut: $30,000 (2/21)
$560,000
2 bds
3 ba
1,900 sqft
Condo for sale
4000 Herons Nest Way Unit 22, Chester, MD 21619
RE/MAX LEADING EDGE
Resort-like pool
$555,900
2 bds
3 ba
2,003 sqft
Condo for sale
3000 Herons Nest Way Unit 11, Chester, MD 21619
COLDWELL BANKER REALTY
Open: Sun 11am-1pm (3/8)
$539,000
2 bds
3 ba
1,900 sqft
Coming soon
111 Marshgrass Way #22, Chester, MD 21619
LONG & FOSTER REAL ESTATE, INC.
On Market Mar 06

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The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. [Click here for more information](/mls-disclaimers/#5632)

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Chester MD Luxury Homes

71 results

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