Chester, Maryland Homes For Sale & Real Estate
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Real Estate Homes For Sale In Chester, MD
![*Open House Saturday 6/29 from 1 to 3pm and Sunday 6/30 from 10am-12pm* Nestled in the desired Waterfront privileged Neighborhood of Marling Farms , this stunning 4 BR (w/Main Level Primary), 2 BA, 2-level Coastal Home epitomizes modern luxury....](https://lh.rdcpix.com/26fb5be43a3a09feab3ee732a70ed8f0l-f2934319923x.jpg)
$569,000 | Active Home listing
4 Beds | 2 Baths | 2,208 Sqft | 0 Acres Lot
1600 CHESTER ROAD, CHESTER, MD 21619 QUEEN ANNES County
![FABULOUS renovations on this gorgeous 3 bedroom, 2 bath home. Hardwood floors thru out, New carpet in the office. Lovely galley kitchen with stainless appliances, ceramic backsplash and leathered granite counters. Updated bathes with designer....](https://lh.rdcpix.com/c9677ac6044b7e06a06a0f2572b92dcbl-f2656114977x.jpg)
$589,900 | Active Home listing
3 Beds | 2 Baths | 0 Sqft | 0 Acres Lot
1303 SAINT MARYS DRIVE RD #1303, CHESTER, MD 21619 QUEEN ANNES County
![Welcome to Four Seasons at Kent Island resort living at its finest, where unparalleled active living meets luxury and convenience. This premier community offers resort-style amenities, including a swimming pool, tennis and pickleball courts, and....](https://lh.rdcpix.com/75f0419fd3937db645ca2300fd04607dl-f2435956263x.jpg)
$549,000 | Active Home listing
2 Beds | 3 Baths | 2,003 Sqft | 0 Acres Lot
2000 HERONS NEST WAY, CHESTER, MD 21619 QUEEN ANNES County
![Welcome to 105 Pilot Ct. in Chester, MD! Located within the sought after community of Castle Marina, this wonderfully updated and renovated 5 bedroom, 3 full bath split level home features 5 bedrooms offers a blend of serene suburban living with....](https://lh.rdcpix.com/0b98a731b1f801f38bc77d71a1ad881al-f2677228494x.jpg)
$570,000 | Active Home listing
5 Beds | 3 Baths | 2,726 Sqft | 1 Acres Lot
105 PILOT COURT, CHESTER, MD 21619 QUEEN ANNES County
![**Wonderful Waterfront Town Home w/out the High Taxes**Three Full Levels of Living on the Chester River!**Open Lower Level has the Living Room Facing the Water**Updated Kitchen w/Granite Counters and SS Appliances**Double Oven and Gas Cook....](https://lh.rdcpix.com/c7bb7f0344c212e040da2323ae2099d9l-f2946539250x.jpg)
$595,000 | Active Home listing
4 Beds | 4 Baths | 0 Sqft | 0 Acres Lot
1006 AUCKLAND WAY, CHESTER, MD 21619 QUEEN ANNES County
![Located in the amenity rich Four Seasons at Kent Island, this ORIGINAL-OWNER property has been meticulously taken care of with many special, unique additions having been made! An open concept great room introduces a decorator neutral paint....](https://lh.rdcpix.com/4a5f169b8c10c38c6c0f91cd6ac52019l-f305248304x.jpg)
$875,000 | Active Home listing
3 Beds | 3 Baths | 0 Sqft | 0 Acres Lot
171 SPINNAKER WAY, CHESTER, MD 21619 QUEEN ANNES County
![OPEN HOUSE, Sat, June 29 from 2:30 - 4 pm...Welcome to your dream home! Nestled in a charming community, this exquisite 5-bedroom sanctuary boasts luxurious features and thoughtful design elements, ensuring comfort and elegance at every turn.
As....](https://lh.rdcpix.com/658c73f3d4307b4e47c9445f26cac8e6l-f3359307598x.jpg)
$650,000 | Active Home listing
5 Beds | 3 Baths | 3,103 Sqft | 0 Acres Lot
1326 QUEEN ANNE DRIVE, CHESTER, MD 21619 QUEEN ANNES County
![Imagine waking up every day in a home that combines the ease of low-maintenance living with the relaxation of a vacation getaway. This dream can become your reality with this stunning 1,440 sqft, 2-bedroom, 2.5-bathroom townhome nestled in the....](https://lh.rdcpix.com/5c90190988e3457e3bcc21581f39cbc2l-f3304214730x.jpg)
$364,900 | Active Home listing
2 Beds | 3 Baths | 1,440 Sqft | 0 Acres Lot
37 QUEEN ANNE WAY, CHESTER, MD 21619 QUEEN ANNES County
![TONS OF EQUITY!!! SELLER IS HIGHLY MOTIVATED!!
Wonderful and well maintained home in Gibson's Grant. This 3/4 Bedroom, 3 Full Bath with Loft Home is 5 Minutes off of Route 50 but has a resort lifestyle. The Community is located on the shores of....](https://lh.rdcpix.com/001dfc9725f33629cf01037fad533f06l-f4075682716x.jpg)
$599,900 | Active Home listing
4 Beds | 3 Baths | 2,464 Sqft | 0 Acres Lot
104 JOHN GIBSON DRIVE, CHESTER, MD 21619 QUEEN ANNES County
![This beautiful Bayside waterfront boasts an open floor plan with gorgeous views. Some of the wonderful highlights include a spacious granite kitchen, living room with built-ins, hardwood floors and garage. Master bedroom has walk-in closet and....](https://lh.rdcpix.com/6590bed1b74b75edbc8003a211ddc4dbl-f3340984951x.jpg)
$579,950 | Active Home listing
3 Beds | 4 Baths | 2,172 Sqft | 0 Acres Lot
703 BLENNY LANE, CHESTER, MD 21619 QUEEN ANNES County
![Welcome to your dream retreat in the heart of a vibrant bayside community! This stunning three-level villa offers breathtaking views of the serene Chester River, ensuring a tranquil ambiance throughout. Step inside to discover a modern haven....](https://lh.rdcpix.com/34dc954a27cda4c2abe6d661ee639a8al-f3577584675x.jpg)
$475,000 | Active Home listing
3 Beds | 4 Baths | 2,112 Sqft | 0 Acres Lot
603 AUCKLAND WAY, CHESTER, MD 21619 QUEEN ANNES County
![Absolutely impeccable 4 bedroom plus office home in the water access community of Gibson’s Grant with outdoor living space including front porch, rear deck and paver patio. Recently remodeled and upgraded with high-end appliances and finishes....](https://lh.rdcpix.com/44bbed9ac1664ae200234c429829041fl-f2719884252x.jpg)
$895,000 | Active Home listing
4 Beds | 3 Baths | 2,856 Sqft | 0 Acres Lot
239 CLAIBORNE STREET, CHESTER, MD 21619 QUEEN ANNES County
![OPEN HOUSE, Sat, June 29 from 10-11:30am Wow! Priced to Sell!! Situated in a picturesque community known for its manicured yards and welcoming atmosphere, this attractive colonial home with a 2-car garage features 4 oversized bedrooms and 2.5....](https://lh.rdcpix.com/dfde7333ada3bbdb2bd97a81e39f5269l-f2557383101x.jpg)
$555,000 | Active Home listing
4 Beds | 3 Baths | 2,356 Sqft | 0 Acres Lot
518 CROSS CREEK COURT, CHESTER, MD 21619 QUEEN ANNES County
![WELCOME HOME TO FOUR SEASONS - KENT ISLAND. This magnificent condo property offers turn-key luxury and a serene resort lifestyle in one of the fastest growing desired communities on the Eastern Shore of Maryland. The meticulousy maintained 2nd....](https://lh.rdcpix.com/1df086251403cc4512e2e160e682a4a1l-f78556735x.jpg)
$599,900 | Active Home listing
2 Beds | 3 Baths | 1,900 Sqft | 0 Acres Lot
3000 HERONS NEST WAY, CHESTER, MD 21619 QUEEN ANNES County
![Why Wait to Build Your Dream Home! This Kent Island Home in Four Seasons is available immediately.
Yard Maintenance included in HOA.
You WILL NOT have to spend THOUSANDS of dollars on the following upgrades. We already have them!
Luxury Spa Bath,....](https://lh.rdcpix.com/7fc7ca5203eb68f1d3698b798475e621l-f3283850900x.jpg)
$798,500 | Active Home listing
3 Beds | 2 Baths | 2,597 Sqft | 0 Acres Lot
224 SALTWORKS DRIVE, CHESTER, MD 21619 QUEEN ANNES County
![Welcome to your dream waterfront retreat! This exquisite 3-level, 3-bedroom, 2.5-bathroom condo offers breathtaking water views from every window. Enjoy your days and nights overlooking the boating acitivty from the marina and Chester River.....](https://lh.rdcpix.com/7a5150f9da79d9cd649c0e6bc4056d41l-f3735438768x.jpg)
$579,000 | Active Home listing
3 Beds | 3 Baths | 1,680 Sqft | 0 Acres Lot
23 QUEEN VICTORIA WAY, CHESTER, MD 21619 QUEEN ANNES County
![K Hovnanian's Four Seasons at Kent Island is an active 55+ community on Maryland's Chesapeake Bay, offering island resort-style and maintenance-free living at its finest! Shows Like a Model!!! The Severn design is a spacious and airy 3 bedroom,....](https://lh.rdcpix.com/76c1a749a94d9c1113ae66d7813bd843l-f1315120342x.jpg)
$736,000 | Active Home listing
3 Beds | 3 Baths | 2,600 Sqft | 0 Acres Lot
141 SWITCHGRASS WAY, CHESTER, MD 21619 QUEEN ANNES County
![Welcome home to island living in this great three bedroom two full and two half bath townhouse with a garage. Walk in from the front door or garage to new LVP flooring downstairs, a fine family room to the back with a slider to the patio, a half....](https://lh.rdcpix.com/67c1d33ca8bb1c0edd2b12fc9b104b5al-f294892353x.jpg)
$385,000 | Active Home listing
3 Beds | 4 Baths | 0 Sqft | 0 Acres Lot
206 BLENNY LN, CHESTER, MD 21619 QUEEN ANNES County
![This house is large and in charge, over 3900 sq feet and 3 levels of living space and it is waiting for new owners. From the spacious kitchen with granite counters, tons of cabinets, downdraft stove, and separate formal dining room. *Corner lot....](https://lh.rdcpix.com/a6523ac96c6317480fb40c399fbb06b9l-f1465956699x.jpg)
$749,989 | Active Home listing
5 Beds | 5 Baths | 3,900 Sqft | 1 Acres Lot
203 SKIPPER LANE, CHESTER, MD 21619 QUEEN ANNES County
![With this MAJOR PRICE IMPROVEMENT, you can save even more while adding your personal touch!! Make an Offer!! This 2 bed, 2.5 bath townhome located in the charming Waterfront community of Queens Landing on Kent Island offers low-maintenance,....](https://lh.rdcpix.com/d104d859d78d7b91fbc6f8b70f62b77dl-f1129212208x.jpg)
$319,000 | Active Home listing
2 Beds | 3 Baths | 1,280 Sqft | 0 Acres Lot
53 QUEEN CAROLINE COURT, CHESTER, MD 21619 QUEEN ANNES County
![Open floorplan with plenty of room for your family. Wonderful gourmet kitchen and formal dining area. Private home office for your personal space. Large great room off balcony with large windows to capture the day. Luxurious owners suite with spa....](https://lh.rdcpix.com/d90d0dabe4b1c61d134f7e55139944abl-f2710614917x.jpg)
$1,004,000 | Active Home listing
2 Beds | 3 Baths | 1,900 Sqft | 0 Acres Lot
224 Switchgrass Way, Unit 42, Chester, MD 21619
![Open floorplan with plenty of room for your family. Wonderful gourmet kitchen and formal dining area. Private home office for your personal space. Large great room off balcony with large windows to capture the day. Luxurious owners suite with spa....](https://lh.rdcpix.com/3425b9c826f7b508c3008cd29d82fde0l-f2710614917x.jpg)
$1,006,000 | Active Home listing
2 Beds | 3 Baths | 1,900 Sqft | 0 Acres Lot
224 Switchgrass Way, Unit 43, Chester, MD 21619
![Why wait for new home to be built. Immediate occupancy for this popular Severn model. Price reduced for quick sale. No steps. No exterior maintenance. One car garage. Plenty of additional parking.
Designer light fixtures, custom window....](https://lh.rdcpix.com/53b19326af205fd73a2c542c898f7035l-f2062948219x.jpg)
$677,600 | Active Home listing
3 Beds | 3 Baths | 2,600 Sqft | 0 Acres Lot
3000 HERONS NEST WAY, CHESTER, MD 21619 QUEEN ANNES County
![Expansive end home condominium with 3 bedrooms. Lavish gourmet kitchen and formal dining area. Huge great room with large corner balcony. Fantastic owners suite and sitting room with access to balcony. Extravagant owners spa bath with two walk-in....](https://lh.rdcpix.com/36cbd8e9a500e62bae7f17c64e476e35l-f2710614917x.jpg)
$899,900 | Active Home listing
3 Beds | 3 Baths | 2,602 Sqft | 0 Acres Lot
129 Wheelhouse Way, Unit 21, Chester, MD 21619
![Open airy floorplan on the first floor with private patio. Large gourmet kitchen and dining area, great for entertaining. Wonderful home office for your telecommuting needs. Sumptuous owners suite with spa bath . Fantastic great room with large....](https://lh.rdcpix.com/e4ed1522036f43c8f613246a871bb5e3l-f2710614917x.jpg)
$709,900 | Active Home listing
2 Beds | 3 Baths | 2,003 Sqft | 0 Acres Lot
129 Wheelhouse Way, Unit 11, Chester, MD 21619
![Wow! A Waterfront with one floor living under $900k! Crab Alley Bay on Kent Island offers stunning views of wildlife, including ducks, swans, and geese. The residence showcases an open floor plan with over 2,000 sf and three distinct living....](https://lh.rdcpix.com/ad76d89f30785be4bbfd3b9f7a4907abl-f3199128387x.jpg)
$829,000 | Active Home listing
3 Beds | 2 Baths | 2,000 Sqft | 0 Acres Lot
1518 SAINT MARYS ROAD, CHESTER, MD 21619 QUEEN ANNES County
![Open floorplan with plenty of room for your family. Wonderful gourmet kitchen and formal dining area. Private home office for your personal space. Large great room off balcony with large windows to capture the day. Luxurious owners suite with spa....](https://lh.rdcpix.com/fcc9f0c520ed2e7b66a03fe0224f47bel-f2710614917x.jpg)
$589,900 | Active Home listing
2 Beds | 3 Baths | 1,900 Sqft | 0 Acres Lot
212 Switchgrass Way, Unit 23, Chester, MD 21619
![Secluded bedroom 2 & bath off foyer for overnight guests. Stylish home office off foyer for working from home. Open & airy great room with adjacent dining area. Striking kitchen with island & tons of cabinet space. Luxurious primary suite with....](https://lh.rdcpix.com/3a1f1bce29fd1eb6c3290a309af901fcl-f1335221472x.jpg)
$685,900 | Active Home listing
2 Beds | 2 Baths | 2,041 Sqft | 0 Acres Lot
131 Flycatcher Way, Chester, MD 21619
![Formal dining room off foyer for entertaining guests. Stylish kitchen with plenty of cabinet space and large island. Open and airy great room with slider to covered patio. Luxurious primary suite with triple windows. Private primary bath with....](https://lh.rdcpix.com/c81e231076e328c392389a18b34a3d3dl-f1335221472x.jpg)
$789,900 | Active Home listing
3 Beds | 4 Baths | 2,963 Sqft | 0 Acres Lot
131 Flycatcher Way, Chester, MD 21619
![Extra Suite Plus for multi-generational living. Striking kitchen with large center island and corner pantry. Spacious great room with tons of windows for natural sun light. Luxurious primary suite with oversized walk-in closet. Relaxing primary....](https://lh.rdcpix.com/172be98869b2593b332f9aec7fcf40fcl-f1335221472x.jpg)
$814,900 | Active Home listing
4 Beds | 4 Baths | 3,570 Sqft | 0 Acres Lot
131 Flycatcher Way, Chester, MD 21619
![Private home office off foyer for working from home. Formal dining room off foyer for entertaining guests. Open and airy floorplan with spacious great room. Striking kitchen with large center island. Luxurious primary suite with oversized walk-in....](https://lh.rdcpix.com/f3e94912dd8163769097f62de61db42cl-f1335221472x.jpg)
$817,900 | Active Home listing
4 Beds | 4 Baths | 3,472 Sqft | 0 Acres Lot
131 Flycatcher Way, Chester, MD 21619
![Extra Suite with full bath for overnight guests. Private home office off foyer for working from home. Spacious great room with adjacent dining area. Beautiful kitchen with large center island. Luxurious primary suite with oversized walk-in closet.....](https://lh.rdcpix.com/614acd4fbeccbfa2734ed22f7b039783l-f1335221472x.jpg)
$781,900 | Active Home listing
5 Beds | 5 Baths | 3,210 Sqft | 0 Acres Lot
131 Flycatcher Way, Chester, MD 21619
![Extra Suite perfect for overnight guests. Private home office off foyer for working from home. Spacious great room with slider to covered patio. Stylish kitchen with island and large pantry. Luxurious primary suite with triple windows. Relaxing....](https://lh.rdcpix.com/f1b62bd6897160e1763e89a730416064l-f1335221472x.jpg)
$752,900 | Active Home listing
3 Beds | 3 Baths | 2,809 Sqft | 0 Acres Lot
131 Flycatcher Way, Chester, MD 21619
![Private bedroom 2 located off foyer for overnight guests. Striking kitchen with large island and plenty of counter space. Open and airy great room with slider to covered patio. Convenient covered patio with screened patio option. Luxurious primary....](https://lh.rdcpix.com/165f9b37f67ffaa707dafde4ef9ccefal-f1335221472x.jpg)
$666,900 | Active Home listing
4 Beds | 3 Baths | 2,791 Sqft | 0 Acres Lot
131 Flycatcher Way, Chester, MD 21619
![Private home office for working from home. Spacious great room with slider to covered patio. Beautiful kitchen with large island and roomy pantry. Luxurious primary suite with triple windows. Relaxing primary bath with spacious shower and walk-in....](https://lh.rdcpix.com/95fad5591e4c1a7d08919308b8f45c27l-f1335221472x.jpg)
$707,900 | Active Home listing
2 Beds | 2 Baths | 2,166 Sqft | 0 Acres Lot
131 Flycatcher Way, Chester, MD 21619
![Elegant foyer welcoming guests to your home. Convenient single-story living. Kitchen with spacious pantry and oversized island. Open-concept great room and dining area adjacent to kitchen. Private primary suite with large walk-in closet and spa....](https://lh.rdcpix.com/fc3412ae0c640826181cf2a7e9e97ce0l-f1335221472x.jpg)
$601,900 | Active Home listing
2 Beds | 2 Baths | 1,693 Sqft | 0 Acres Lot
131 Flycatcher Way, Chester, MD 21619
![Private home office for working from home. Stylish kitchen with large center island and spacious pantry. Spacious great room with slider to covered patio. Luxurious primary suite with oversized walk-in closet. Palatial primary bath with split....](https://lh.rdcpix.com/20857bc5c6dbdc43840137f65fa43e27l-f1335221472x.jpg)
$631,900 | Active Home listing
2 Beds | 2 Baths | 1,996 Sqft | 0 Acres Lot
131 Flycatcher Way, Chester, MD 21619
![Open floorplan with plenty of room for your family. Wonderful gourmet kitchen and formal dining area. Private home office for your personal space. Large great room off balcony with large windows to capture the day. Luxurious owners suite with spa....](https://lh.rdcpix.com/726fde1ff0836373a6f9ad011ad96a66l-f2710614917x.jpg)
$459,990 | Active Home listing
2 Beds | 3 Baths | 1,900 Sqft | 0 Acres Lot
131 Flycatcher Way, Chester, MD 21619
![Open airy floorplan on the first floor with private patio. Large gourmet kitchen and dining area, great for entertaining. Wonderful home office for your telecommuting needs. Sumptuous owners suite with spa bath . Fantastic great room with large....](https://lh.rdcpix.com/5b9df6ef76311ebbec0e79c83e00bda8l-f2710614917x.jpg)
$459,990 | Active Home listing
2 Beds | 3 Baths | 2,003 Sqft | 0 Acres Lot
131 Flycatcher Way, Chester, MD 21619
Chester, MD Real Estate Home Trends
Queen Anne's County Buy Statistics
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Chester Types of Homes for Sale
Chester Real Estate Listings
Chester, MD Homes Prices
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Real Estate Home Mortgage Loan Rates Chester Maryland
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About Chester
Chester has total households of 19,351 with a real estate for sale median home value of $421,900 compared to the state median home price of $411,900. The median real estate taxes paid are $Not Available and the household income is $108,332. Not Available% of Chester homes with a mortgage have no second mortgage or home equity line of credit. Chester Maryland home types of MLS housing to buy including single family homes, condos, townhomes, residential studio, apartment, townhouse, and multi-family houses.
Homes in Nearby Cities
Housing Disclaimer: Certain information contained herein is derived from information provided by parties other than Airdeed.com. All information provided is deemed reliable, but is not guaranteed to be accurate and users should independently verify all information.
Chester Community Map
§ 442-H New York Standard Operating Procedures
TREC: Consumer protection notice
HUD: Equal Opportunity Housing