Consider our listings of homes for sale in Chester and nearby areas.

You may filter our residential listings by specifying price ranges of houses, number of bedrooms and baths, as well as by the total square footage. Let your search for new homes for sale for Chester begin here!

1840 SqFt House In Clayborne Woods
	1840 SqFt House In Clayborne Woods Chester, MD $365,000 Homes for Sale Open House on Saturday, 3/14 from 11am-1pm! Welcome to the sought after, private community of Clayborne Woods where life is simple! Have you looked at other homes and just can't find the one? This......

1976 SqFt House In Marling Farms
	1976 SqFt House In Marling Farms Chester, MD $359,900 Homes for Sale Nearly 2000 SF of ONE-Level, Updated Living with Attached 2-Car Garage, Tucked in the Coveted Water-Access Community of Marling Farms, Just 10 Mins from Bay Bridge- GORGEOUS Updated Kitchen w/......

1069 SqFt House In Bayside
	1069 SqFt House In Bayside Chester, MD $220,000 Homes for Sale Open Sunday 1-3pm You have been waiting for this one and here it is! The only Bayside Condo on the market and it is ground level with hardwood floors throughout! Come right in and fall in love with......

Move In Ready New Home In K. Hovnanians Four Seasons at Kent Island Community
	Move In Ready New Home In K. Hovnanians Four Seasons at Kent Island Community Chester, MD $765,506 Homes for Sale  NEW! This new construction, quick move-in home is the "Santorini Loft" plan by K. Hovnanian's Four Seasons, and is located in the community of The K. Hovnanians Four Seasons at Kent Island at 227......

Renovated 5-Bedroom House In Bentons Pleasure
	Renovated 5-Bedroom House In Bentons Pleasure Chester, MD $439,000 Homes for Sale  NEW! Fantastic Opportunity to live on Kent Island with a Water View.... Don't Miss out on this one. Short Distance and Easy commute to the Bridge. Beautifully Renovated 5 Bedroom 3 Full Bathroom house......

Upgraded 3-Bedroom House In Chester
	Upgraded 3-Bedroom House In Chester Chester, MD $269,750 Homes for Sale  NEW! LOCATION LOCATION LOCATION- A COMMUTERS DREAM WITH EASY ACCESS TO ROUTE 50 AND THE BAY BRIDGE! WELCOME TO YOUR MOVE-IN READY, NEWLY RENOVATED HOME! 3 BEDROOM 2 FULL BATH RANCHER WAS TOTALLY REDONE......

1635 SqFt House In Bridgepointe
	1635 SqFt House In Bridgepointe Chester, MD $299,000 Homes for Sale  NEW! Beautiful move-in ready, all updated! Stainless appliances, new HVAC, new roof, new upstairs carpet, a must-see home. This home is located on the beautiful eastern shore,.Kent Island. It's close to......

3571 SqFt House In Bentons Pleasure
	3571 SqFt House In Bentons Pleasure Chester, MD $1,075,000 Homes for Sale  NEW! JUST LISTED!! Summer IS Coming... Better Hurry to. This GORGEOUS Custom-Built Kent Island WATERFRONT! It's what 'Island Living' is All About! Private Pier, w/ Boat Lift & Jet Ski Lift Just Begging......

2925 SqFt House In Marling Farms
	2925 SqFt House In Marling Farms Chester, MD $825,000 Homes for Sale  NEW! Quality custom construction with panoramic waterviews, large site, and state-of-the art systems. Features include...geothermal two-zone HVAC, 2x6 construction, 10' ceilings and vaulted ceilings on......

1132 SqFt House In Chester
	1132 SqFt House In Chester Chester, MD $260,000 Homes for Sale  NEW! Retreat to your own little private escape on Kent Island. Forget condo living when you can have your own driveway and fenced in back yard!~This peaceful home rest on a 1/2 + acre located on a quiet......

3694 SqFt House In Southwind
	3694 SqFt House In Southwind Chester, MD $1,195,000 Homes for Sale  NEW! Come see the new look to this beautiful custom home on Crab Alley Bay. Gourmet chef's kit w/new quartz X large island and backsplash. Outside deck now offers waterfall steps to a multi level very......

Ready To Build Home In Covell Signature Homes Community
	Ready To Build Home In Covell Signature Homes Community Chester, MD $589,900 Homes for Sale  NEW! This build-on-your-lot home is the "Port Royal Executive" plan by Covell Communities. This single family plan home is priced from $589,900 (price typically does not include lot cost). This plan......

2791 SqFt House In Bentons Pleasure
	2791 SqFt House In Bentons Pleasure Chester, MD $599,900 Homes for Sale  NEW! Do not miss this gorgeous, custom-built home in Benton's Pleasure that sits on a One Acre Lot. This stone-front home boasts a gourmet kitchen and open floor plan making it an entertainer's dream.......

Ready To Build Home In Covell Signature Homes Community
	Ready To Build Home In Covell Signature Homes Community Chester, MD $579,900 Homes for Sale  NEW! This build-on-your-lot home is the "Belle Haven Classic" plan by Covell Communities. This single family plan home is priced from $579,900 (price typically does not include lot cost). This plan......

Private House With Fireplace
	Private House With Fireplace Chester, MD $595,000 Homes for Sale  NEW! Southern/Coastal-inspired design in Gibson~s Grant. Open floor plan, this 3 Bedroom/2.5 Bath home is impeccably maintained, featuring Granite tops, Hardwoods & SS appl. Family room with stacked......

Move In Ready New Home In K. Hovnanians Four Seasons at Kent Island Community
	Move In Ready New Home In K. Hovnanians Four Seasons at Kent Island Community Chester, MD $492,060 Homes for Sale  NEW! This new construction, quick move-in home is the "Donegal - River Series" plan by K. Hovnanian's Four Seasons, and is located in the community of The K. Hovnanians Four Seasons at Kent Island at......

Ready To Build Home In Covell Signature Homes Community
	Ready To Build Home In Covell Signature Homes Community Chester, MD $589,900 Homes for Sale  NEW! This build-on-your-lot home is the "East Port Classic" plan by Covell Communities. This single family plan home is priced from $589,900 (price typically does not include lot cost). This plan offers......

Ready To Build Home In K. Hovnanians Four Seasons at Kent Island Community
	Ready To Build Home In K. Hovnanians Four Seasons at Kent Island Community Chester, MD $429,990 Homes for Sale  NEW! This to-be-built home is the "Magothy - Condominium" plan by K. Hovnanian's Four Seasons, and is located in the community of The K. Hovnanians Four Seasons at Kent Island. Special Offer!: Four......

2184 SqFt House In Chester
	2184 SqFt House In Chester Chester, MD $594,990 Homes for Sale  NEW! Do not miss out on One level living in our Stanford floorplan. 3 bedrooms, 2. full baths, 2 car garage. Finished garage studio available. Do not miss out on living in Gibson Grant with community......

Ready To Build Home In Covell Signature Homes Community
	Ready To Build Home In Covell Signature Homes Community Chester, MD $649,900 Homes for Sale  NEW! This build-on-your-lot home is the "East Port Legacy" plan by Covell Communities. This single family plan home is priced from $649,900 (price typically does not include lot cost). This plan offers......

Ready To Build Home In K. Hovnanians Four Seasons at Kent Island Community
	Ready To Build Home In K. Hovnanians Four Seasons at Kent Island Community Chester, MD $429,990 Homes for Sale  NEW! This to-be-built home is the "Ibiza - Bay Series" plan by K. Hovnanian's Four Seasons, and is located in the community of The K. Hovnanians Four Seasons at Kent Island. Special Offer!: Four Seasons......

Move In Ready New Home In K. Hovnanians Four Seasons at Kent Island Community
	Move In Ready New Home In K. Hovnanians Four Seasons at Kent Island Community Chester, MD $493,368 Homes for Sale  NEW! This new construction, quick move-in home is the "Chester - Condominium" plan by K. Hovnanian's Four Seasons, and is located in the community of The K. Hovnanians Four Seasons at Kent Island at......

Ready To Build Home In Covell Signature Homes Community
	Ready To Build Home In Covell Signature Homes Community Chester, MD $599,900 Homes for Sale  NEW! This build-on-your-lot home is the "Kitty Hawk Legacy" plan by Covell Communities. This single family plan home is priced from $599,900 (price typically does not include lot cost). This plan offers......

2844 SqFt House In Chester
	2844 SqFt House In Chester Chester, MD $599,000 Homes for Sale  NEW! Marling Farms Waterfront - The views and sunsets are everything you want and more from this property. The home has a new kitchen, hardwood flooring, pier and boat lifts. Three Bedrooms and Three......

Ready To Build Home In Covell Signature Homes Community
	Ready To Build Home In Covell Signature Homes Community Chester, MD $549,900 Homes for Sale This build-on-your-lot home is the "Kitty Hawk Classic" plan by Covell Communities. This single family plan home is priced from $549,900 (price typically does not include lot cost). This plan......

Ready To Build Home In K. Hovnanians Four Seasons at Kent Island Community
	Ready To Build Home In K. Hovnanians Four Seasons at Kent Island Community Chester, MD $394,990 Homes for Sale This to-be-built home is the "Grenada - River Series" plan by K. Hovnanian's Four Seasons, and is located in the community of The K. Hovnanians Four Seasons at Kent Island. Special Offer!: Four......

Ready To Build Home In K. Hovnanians Four Seasons at Kent Island Community
	Ready To Build Home In K. Hovnanians Four Seasons at Kent Island Community Chester, MD $439,990 Homes for Sale This to-be-built home is the "Lille - Bay Series" plan by K. Hovnanian's Four Seasons, and is located in the community of The K. Hovnanians Four Seasons at Kent Island. Special Offer!: Four Seasons......

Move In Ready New Home In K. Hovnanians Four Seasons at Kent Island Community
	Move In Ready New Home In K. Hovnanians Four Seasons at Kent Island Community Chester, MD $595,854 Homes for Sale This new construction, quick move-in home is the "San Sebastian - Island Series" plan by K. Hovnanian's Four Seasons, and is located in the community of The K. Hovnanians Four Seasons at Kent......

Waterfront House With Fireplace
	Waterfront House With Fireplace Chester, MD $589,000 Homes for Sale Welcome Home! This one is a RARE find in Gibson's Grant - You will never have a neighbor across the street - just the peace of the protected pond view from your front porch on one of the only dead......

5328 SqFt House In Southwind
	5328 SqFt House In Southwind Chester, MD $1,400,000 Homes for Sale Great, Custom Colonial on Crab Alley Bay, located in the community of Southwind. Home features large open spaces on first and third floor, custom kitchen, new master bath, freshly painted......

Ready To Build Home In K. Hovnanians Four Seasons at Kent Island Community
	Ready To Build Home In K. Hovnanians Four Seasons at Kent Island Community Chester, MD $536,990 Homes for Sale This to-be-built home is the "San Sebastian Loft - Island Series" plan by K. Hovnanian's Four Seasons, and is located in the community of The K. Hovnanians Four Seasons at Kent Island. Special......

1764 SqFt House In Chester
	1764 SqFt House In Chester Chester, MD $359,900 Homes for Sale Beautiful home available in the lovely community of Calyborne Woods! Features include a main level master suite with vaulted ceilings, walk in closet, and master bath. Kitchen with new stainless......

1851 SqFt House In Chester
	1851 SqFt House In Chester Chester, MD $471,990 Homes for Sale You do not want to miss out with building a new Koch Home in Gibson's Grant! Build a Langley, 3 bedroom, 2.5 baths, 1 car garage, option for 2 car and optional bonus space above garage with......

Ready To Build Home In Covell Signature Homes Community
	Ready To Build Home In Covell Signature Homes Community Chester, MD $489,900 Homes for Sale This build-on-your-lot home is the "Oxford Legacy" plan by Covell Communities. This single family plan home is priced from $489,900 (price typically does not include lot cost). This plan offers 2......

1204 SqFt House In Chester
	1204 SqFt House In Chester Chester, MD $269,000 Homes for Sale Welcome Home! This bright and freshly painted home is move in ready. Full glass atrium door in the dining area open to the deck and large fenced back yard. Gleaming blonde wood tone flooring......

1844 SqFt House In Chester
	1844 SqFt House In Chester Chester, MD $444,900 Homes for Sale Lowest Price in Gibson's Grant! This Stunning 3 Br Koch Langley Model Offers Affordable Single Family Home Living in The Popular Water Privileged Community On Kent Island. Features Loads Of......

Ready To Build Home In Covell Signature Homes Community
	Ready To Build Home In Covell Signature Homes Community Chester, MD $569,900 Homes for Sale This build-on-your-lot home is the "Port Royal Legacy" plan by Covell Communities. This single family plan home is priced from $569,900 (price typically does not include lot cost). This plan offers......

1536 SqFt House In Chester
	1536 SqFt House In Chester Chester, MD $340,000 Homes for Sale Home complete and move in ready! Can close in 30 days. Quiet small new waterfront community of Waterman's Cove- Just a short mile off Rt 50 on Cox Neck Road for super easy commutes. This enclave of......

High-End 3-Bedroom House In Chester
	High-End 3-Bedroom House In Chester Chester, MD $585,000 Homes for Sale Main-Level Master Suite in Coveted Gibson's Grant!! High End Finishes Throughout! Over 2400 sq ft, 2 HUGE Upper-Level Bedrooms, Finished Room Over Garage for Large Bonus Space! Attached 2-Car......

Move In Ready New Home In K. Hovnanians Four Seasons at Kent Island Community
	Move In Ready New Home In K. Hovnanians Four Seasons at Kent Island Community Chester, MD $441,853 Homes for Sale This new construction, quick move-in home is the "Chester - Condominium" plan by K. Hovnanian's Four Seasons, and is located in the community of The K. Hovnanians Four Seasons at Kent Island at......