58

Chester, MD Homes for Sale with Pool

Section Image Section Image
  • 330 Macum Creek Dr, Chester, MD 21619
    330 Macum Creek Dr, Chester, MD 21619
    330 Macum Creek Dr, Chester, MD 21619
    /55

    $1,050,000

    • 4 Beds
    • 3.5 Baths
    • 3,949 Sq Ft

    330 Macum Creek Dr, Chester, MD 21619

    Welcome home to luxurious living Gibson's Grant! This stunning home offers a perfect blend of luxury and functionality, featuring extensive upgrades throughout. The backyard is an entertainer’s dream with a custom patio, covered outdoor kitchen, bonus grassy area for pets or play, and a fully fenced yard. A former screened porch has been converted into a bright and inviting four-season sunroom,

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (667) 256-7961

    330 Macum Creek Dr, Chester, MD 21619
  • 34 Queen Anne Way, Chester, MD 21619
    34 Queen Anne Way, Chester, MD 21619
    34 Queen Anne Way, Chester, MD 21619
    /57

    $469,000

    • 2 Beds
    • 2.5 Baths
    • 1,104 Sq Ft

    34 Queen Anne Way, Chester, MD 21619

    Price Improvement on this CHESTER RIVER WATERFRONT Eastern Shore! Nestled within the water-privileged resort-style community of Queen's Landing, along the scenic Chester River and Macum Creek off the Chesapeake Bay. Step into the light-filled foyer and head up the stairs to the main level, you will find this lovely 2 bedroom, 2.5 bath condominium is move in ready. Just bring your patio chairs,

    Agent Photo

    Lona Todd

    Taylor Properties

    (667) 291-8898

    34 Queen Anne Way, Chester, MD 21619
  • 4000 Herons Nest Way Unit 22, Chester, MD 21619
    4000 Herons Nest Way Unit 22, Chester, MD 21619
    4000 Herons Nest Way Unit 22, Chester, MD 21619
    /62

    $530,000

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    4000 Herons Nest Way Unit 22, Chester, MD 21619

    Four Seasons @ Kent Island - 55+ Community - $10,000 Closing Cost Assistance Available - Turn Key & Lovely 2nd Floor Condo in Elevator Building with 1 Car Garage plus 1 Car Outdoor Parking and Private, Secure Indoor Storage Area. This Chester Model offers 1900 sf with pond view and winter water views of Macum Creek. Enter to find an expansive, open floor plan featuring a beautiful white Kitchen

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    (410) 936-3917

    4000 Herons Nest Way Unit 22, Chester, MD 21619
  • 54A Queen Caroline Ct, Chester, MD 21619
    54A Queen Caroline Ct, Chester, MD 21619
    54A Queen Caroline Ct, Chester, MD 21619
    /43

    $465,000

    • 2 Beds
    • 2.5 Baths
    • 1,280 Sq Ft

    54A Queen Caroline Ct, Chester, MD 21619

    OPEN HOUSE, Sunday, July 20, 12-2pm...End Unit in Sought-After Queens Landing – A Waterfront Lifestyle Awaits!Don’t miss this spacious end unit in the highly desirable Queens Landing community! Featuring two primary bedroom suites with private baths, this home offers the perfect blend of comfort and functionality. The expansive kitchen is a chef’s dream, boasting granite countertops,

    Darlene Winegardner RE/MAX Executive

    54A Queen Caroline Ct, Chester, MD 21619
  • 170 Harrier Way Unit 11, Chester, MD 21619
    170 Harrier Way Unit 11, Chester, MD 21619
    170 Harrier Way Unit 11, Chester, MD 21619
    /74

    $499,000

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    170 Harrier Way Unit 11, Chester, MD 21619

    ***Redfin powered by Rocket Mortgage Preferred Pricing*** Enjoy with a 1% lower interest rate for your initial year or potential savings of up to $6,000 on your closing costs when you finance with Rocket Mortgage*** Move-In Ready 2-Bedroom Condo in Four Seasons at Kent Island! Discover this stunning 2-bedroom, 2.5-bath condo in the sought-after 55+ community of Four Seasons at Kent

    Scott Swahl Redfin Corp

    170 Harrier Way Unit 11, Chester, MD 21619
  • Mykonos, Chester, MD 21619
    Mykonos, Chester, MD 21619
    Mykonos, Chester, MD 21619
    /12

    $872,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,512 Sq Ft

    Mykonos, 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 closet. Relaxing primary bath with optional freestanding tub. Convenient 3-car tandem garage for additional

    K Hovnanian's Four Seasons

    Mykonos, Chester, MD 21619
  • Kerr, Chester, MD 21619
    Kerr, Chester, MD 21619
    Kerr, Chester, MD 21619
    /26

    $807,900 New Construction

    • 3 Beds
    • 3 Baths
    • 2,789 Sq Ft

    Kerr, 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 primary bath with split vanities and walk-in closet. Convenient 3-car tandem garage for additional storage space.

    K Hovnanian's Four Seasons

    Kerr, Chester, MD 21619
  • Jenkins II, Chester, MD 21619
    Jenkins II, Chester, MD 21619
    Jenkins II, Chester, MD 21619
    /24

    $659,900 New Construction

    • 2 Beds
    • 2 Baths
    • 1,993 Sq Ft

    Jenkins II, 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 vanities. Convenient HovHall off garage for keeping home tidy.

    K Hovnanian's Four Seasons

    Jenkins II, Chester, MD 21619
  • Taylor, Chester, MD 21619
    Taylor, Chester, MD 21619
    Taylor, Chester, MD 21619
    /10

    $740,900 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,010 Sq Ft

    Taylor, Chester, MD 21619

    Secluded bedroom 2 and 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 oversized walk-in closet.Palatial primary bath with roomy shower.Convenient 3-car tandem garage for additional storage.

    K Hovnanian's Four Seasons

    Taylor, Chester, MD 21619
  • Magothy, Chester, MD 21619
    Magothy, Chester, MD 21619
    Magothy, Chester, MD 21619
    /12

    $474,990 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    Magothy, 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 owner’s suite with spa bath . Fantastic great room with large windows for your viewing pleasure. Large secondary bedroom with opt. door to access patio. Pricing is

    K Hovnanian's Four Seasons

    Magothy, Chester, MD 21619
  • Franklin, Chester, MD 21619
    Franklin, Chester, MD 21619
    Franklin, Chester, MD 21619
    /27

    $844,900 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,930 Sq Ft

    Franklin, 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 optional freestanding tub. Convenient 2-car garage with storage space.

    K Hovnanian's Four Seasons

    Franklin, Chester, MD 21619
  • Tuscaloosa, Chester, MD 21619
    Tuscaloosa, Chester, MD 21619
    Tuscaloosa, Chester, MD 21619
    /40

    $836,900 New Construction

    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft

    Tuscaloosa, 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. Relaxing primary bath with optional freestanding tub. Convenient 3-car tandem garage for additional storage.

    K Hovnanian's Four Seasons

    Tuscaloosa, Chester, MD 21619
  • 255 Sailcloth Way, Chester, MD 21619
    255 Sailcloth Way, Chester, MD 21619
    255 Sailcloth Way, Chester, MD 21619
    /56

    $950,000

    • 4 Beds
    • 4 Baths
    • 3,450 Sq Ft

    255 Sailcloth Way, Chester, MD 21619

    COMING SOON - The Double Primary Bedroom Santorini model with 3,500 sq ft that everyone loves, perfectly situated on a cul de sac lot with a long list of upgrades including the gourmet kitchen, luxury baths in BOTH primary bedrooms, the loft with full bath and sky basement, Screened porch and so much more! This is perfect for multi-generational living! Four Seasons on Kent Island is a resort

    Kathleen Higginbotham Keller Williams Flagship

    255 Sailcloth Way, Chester, MD 21619
  • 162 Kirwans Landing Ln, Chester, MD 21619
    162 Kirwans Landing Ln, Chester, MD 21619
    162 Kirwans Landing Ln, Chester, MD 21619
    /37

    $1,195,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 2.5 Baths
    • 2,404 Sq Ft

    162 Kirwans Landing Ln, Chester, MD 21619

    Welcome to 162 Kirwans Landing Lane—a beautifully updated residence located in the sought-after, water-privileged community of Kirwans Landing. Set on 1.4 private acres, this 4-bedroom, 2.5-bath home offers a seamless blend of refined comfort and exceptional outdoor living.Inside, you’ll find hardwood floors throughout both levels, a renovated kitchen with granite countertops, custom

    Brad Kappel TTR Sotheby's International Realty

    162 Kirwans Landing Ln, Chester, MD 21619
  • 25 Queen Elizabeth Ct, Chester, MD 21619
    25 Queen Elizabeth Ct, Chester, MD 21619
    25 Queen Elizabeth Ct, Chester, MD 21619
    /39

    $569,000

    • 3 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    25 Queen Elizabeth Ct, Chester, MD 21619

    Experience breathtaking sunrises over the Chester River and Chesapeake Bay from this beautifully updated, three-level townhouse-style condo. Located in a serene waterfront community, this home offers the perfect blend of modern amenities and natural beauty. The front entrance welcomes you with a porcelain-tile foyer and a river-rock inset, leading into an open living area with stunning water

    Evguenia Mathur Samson Properties

    25 Queen Elizabeth Ct, Chester, MD 21619
  • 312 Blenny Ln, Chester, MD 21619
    312 Blenny Ln, Chester, MD 21619
    312 Blenny Ln, Chester, MD 21619
    /39

    $479,000

    • 3 Beds
    • 4 Baths
    • 1,899 Sq Ft

    312 Blenny Ln, Chester, MD 21619

    You do not want to miss this opportunity to enjoy island living in this maintenance free, WATER VIEW-End UNIT! Come enjoy island living in the Bayside Community. Offering POND views from every window in this sought after end unit home complete with beautiful landscaping. Relax on your spacious deck overlooking the pond complete with 2 fountains or invite family and friends to enjoy a cookout

    Judith Brown Samson Properties

    312 Blenny Ln, Chester, MD 21619
  • 49 Queen Guinivere Way, Chester, MD 21619
    49 Queen Guinivere Way, Chester, MD 21619
    49 Queen Guinivere Way, Chester, MD 21619
    /79

    $529,250

    • 2 Beds
    • 2.5 Baths
    • 1,600 Sq Ft

    49 Queen Guinivere Way, Chester, MD 21619

    Welcome to Queens Landing, where resort-style living meets the comfort of home. This beautifully updated townhome offers 1,440 square feet of thoughtfully designed living space plus an open sunroom, adding approximately 160 additional square feet, creating a seamless and spacious floor plan ideal for everyday living and entertaining.Enjoy panoramic water views from every room - lake and

    Julia Stevens Realty Navigator

    49 Queen Guinivere Way, Chester, MD 21619
  • 15 Queen Anne Way Unit E, Chester, MD 21619
    15 Queen Anne Way Unit E, Chester, MD 21619
    15 Queen Anne Way Unit E, Chester, MD 21619
    /68

    $539,000

    • 2 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    15 Queen Anne Way Unit E, Chester, MD 21619

    Price Improvement and a full year of Condo Fees paid!! Wake up to shimmering Chester River views and let every day feel like a getaway!This beautifully maintained 2.5-level townhome offers 1,680 square feet of stylish and functional living space in the sought-after waterfront community of Queens Landing. The main level features a cozy living area with a gas fireplace, luxury vinyl plank

    Julia Stevens Realty Navigator

    15 Queen Anne Way Unit E, Chester, MD 21619
  • 112 Harbour Sound Dr, Chester, MD 21619
    112 Harbour Sound Dr, Chester, MD 21619
    112 Harbour Sound Dr, Chester, MD 21619
    /40

    $539,500

    • 3 Beds
    • 3.5 Baths
    • 2,131 Sq Ft

    112 Harbour Sound Dr, Chester, MD 21619

    Resort Living at it's best!! Available furnished or unfurnished. Enjoy stunning, unobstructed water views in the highly sought after community of Bayside! Many recent upgrades and improvements to this home include renovated bathrooms (2024) , New garage door, with fresh sealing floor paint (2023) New Kitchen cabinets (2022), New Double Oven (2022) , New Quartz Countertops (2022) New flooring

    Carlos Larraz Annapolis Properties LLC

    112 Harbour Sound Dr, Chester, MD 21619
  • 132 Claiborne St, Chester, MD 21619
    132 Claiborne St, Chester, MD 21619
    132 Claiborne St, Chester, MD 21619
    /77

    $750,000

    • 3 Beds
    • 3.5 Baths
    • 2,400 Sq Ft

    132 Claiborne St, Chester, MD 21619

    Sitting pretty on one of the largest, level lots in the prestigious Gibson's Grant Community, w/ beautiful landscaping, flowers now blooming, and a lawn irrigation system. The lot is enhanced with landscape lighting and a wood fence. This front porch Chatham model is inviting w/sidewalk extension and has a good view of the peaceful pond and natural surroundings. The foyer and main level have

    Melanie Mcknight RE/MAX Professionals

    132 Claiborne St, Chester, MD 21619
  • 164 Redstart Dr, Chester, MD 21619
    164 Redstart Dr, Chester, MD 21619
    164 Redstart Dr, Chester, MD 21619
    /57

    $889,900 New Construction

    • 3 Beds
    • 3 Baths
    • 2,789 Sq Ft

    164 Redstart Dr, Chester, MD 21619

    Discover the charm and versatility of the Kerr, a thoughtfully designed 3-bedroom, 3-bath home offering an open layout, high-end finishes, and spaces tailored for comfort. With a 3-car garage and flexible rooms throughout, this home adapts beautifully to everyday living or entertaining.The main level features durable Luxury Vinyl Plank flooring, a warm fireplace, and a screened patio for

    Mary Anne Kowalewski KOVO Realty

    164 Redstart Dr, Chester, MD 21619
  • 327 Kingfisher Ln, Chester, MD 21619
    327 Kingfisher Ln, Chester, MD 21619
    327 Kingfisher Ln, Chester, MD 21619
    /45

    $999,900 New Construction

    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft

    327 Kingfisher Ln, Chester, MD 21619

    Welcome to the Tuscaloosa, a stunning 5-bedroom, 4.5-bath home designed for flexible living and modern style. With a 3-car garage, open-concept layout, and high-end finishes, this home is the perfect blend of comfort and sophistication.Enjoy thoughtful details throughout, including a cozy fireplace, versatile home office, bright loft, and a relaxing screened patio. The kitchen features a full

    Mary Anne Kowalewski KOVO Realty

    327 Kingfisher Ln, Chester, MD 21619
  • Severn, Chester, MD 21619
    Severn, Chester, MD 21619
    Severn, Chester, MD 21619
    /21

    $559,990 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    Severn, Chester, MD 21619

    Expansive end home condominium with 3 bedrooms.Lavish gourmet kitchen and formal dining area.Huge great room with large corner balcony.Fantastic owner’s suite and sitting room with access to balcony.Extravagant owner’s spa bath with two walk-in closets.Large secondary bedrooms for all of your company.Pricing is inclusive of an average location premium.

    K Hovnanian's Four Seasons

    Severn, Chester, MD 21619
  • Munich ESP, Chester, MD 21619
    Munich ESP, Chester, MD 21619
    Munich ESP, Chester, MD 21619
    /12

    $869,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,601 Sq Ft

    Munich ESP, 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 bath with split vanities and optional freestanding tub. Private home office off foyer for working from home.

    K Hovnanian's Four Seasons

    Munich ESP, Chester, MD 21619
  • Kelly, Chester, MD 21619
    Kelly, Chester, MD 21619
    Kelly, Chester, MD 21619
    /11

    $762,900 New Construction

    • 2 Beds
    • 2 Baths
    • 2,143 Sq Ft

    Kelly, 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 closet. Convenient covered patio with screen patio option.

    K Hovnanian's Four Seasons

    Kelly, Chester, MD 21619
  • Simone, Chester, MD 21619
    Simone, Chester, MD 21619
    Simone, Chester, MD 21619
    /13

    $691,900 New Construction

    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft

    Simone, 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 suite with oversized walk-in closet. Relaxing primary bath with split vanities. Versatile loft on second

    K Hovnanian's Four Seasons

    Simone, Chester, MD 21619
  • 121 John Gibson Dr, Chester, MD 21619
    121 John Gibson Dr, Chester, MD 21619
    /2

    $825,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 2.5 Baths
    • 2,760 Sq Ft

    121 John Gibson Dr, Chester, MD 21619

    PHOTOS COMING SOON! Welcome home to 121 John Gibson Drive in the waterfront community of Gibson's Grant on Kent Island. This beautifully maintained 4-bedroom, 2.5-bath home offers the perfect blend of charm, functionality, and comfort. Step inside to discover a bright and open floor plan featuring a cozy gas fireplace, ideal for relaxing evenings or entertaining guests. The heart of the home

    Tara Trout Keller Williams Flagship

    121 John Gibson Dr, Chester, MD 21619
  • 137 Warbler Way, Stevensville, MD 21666
    137 Warbler Way, Stevensville, MD 21666
    137 Warbler Way, Stevensville, MD 21666
    /81

    $739,950 New Construction

    • 2 Beds
    • 2 Baths
    • 2,147 Sq Ft

    137 Warbler Way, Stevensville, MD 21666

    No waiting on the builder here! Treat yourself to this STUNNING move-in-ready Four Seasons beauty- Boasting soaring ceilings, flooded with natural light, spacious, open-floor plan nearly 2200 SF, with generously-sized primary suite & spa-like bath with walk-in-closet, double sinks & walk-in-shower. 2nd bedroom & bath across home offers privacy for guests. Custom barn doors open to bonus space-

    Jennifer Chaney Chaney Homes, LLC

    137 Warbler Way, Stevensville, MD 21666
  • 31C Queen Anne Way, Chester, MD 21619
    31C Queen Anne Way, Chester, MD 21619
    31C Queen Anne Way, Chester, MD 21619
    /46

    $334,900

    • 2 Beds
    • 1.5 Baths
    • 1,104 Sq Ft

    31C Queen Anne Way, Chester, MD 21619

    Welcome to 31-C Queen Anne Way, a beautifully updated two-bedroom, 1.5-bath located in Condo located in the desirable waterfront community of Queens Landing. This well-maintained unit offers 1,104 square feet of thoughtfully designed living space spread across the second and third levels. Enjoy unobstructed views of Lake Amletto and the community water tower, along with partial but striking

    Julia Stevens Realty Navigator

    31C Queen Anne Way, Chester, MD 21619
  • 224 Bayberry Dr, Chester, MD 21619
    224 Bayberry Dr, Chester, MD 21619
    224 Bayberry Dr, Chester, MD 21619
    /47

    $619,900

    • 2 Beds
    • 2 Baths
    • 1,913 Sq Ft

    224 Bayberry Dr, Chester, MD 21619

    Discover the charm of this meticulously maintained, one-owner Donegal model nestled in the highly desirable, water-privileged 55+ community of Four Seasons at Kent Island. This stunning single-family home features an expansive open-concept layout, enhanced with designer lighting and custom finishes that elevate the home's ambiance.Step into a spacious kitchen that serves as the heart of

    Petra Quinn Realty Navigator

    224 Bayberry Dr, Chester, MD 21619
  • 190 Harrier Way Unit 11, Chester, MD 21619
    190 Harrier Way Unit 11, Chester, MD 21619
    190 Harrier Way Unit 11, Chester, MD 21619
    /32

    $540,000

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    190 Harrier Way Unit 11, Chester, MD 21619

    Luxury 55+ Living at Four Seasons on Kent Island – Move-In Ready & Priced to Sell!Welcome to the resort-style lifestyle of Four Seasons on Kent Island, an amenity-rich 55+ waterfront community where luxury, comfort, and convenience meet. Inside, you'll find open-concept layouts filled with natural light, gourmet kitchens with quartz countertops, GE Profile stainless steel

    Jennifer Thomas RE/MAX Executive

    190 Harrier Way Unit 11, Chester, MD 21619
  • 205 Anchor Ln, Chester, MD 21619
    205 Anchor Ln, Chester, MD 21619
    205 Anchor Ln, Chester, MD 21619
    /47

    $566,000

    • 5 Beds
    • 3 Baths
    • 3,500 Sq Ft

    205 Anchor Ln, Chester, MD 21619

    Price Improvement! Need more room? This expansive home is ready to welcome your whole family! With 5 bedrooms, 3 full bathrooms and an over-sized 4-car garage, there's plenty of space for everyone to spread out and enjoy their own privacy.You'll be delighted by a mix of formal and casual living spaces, including a bright formal living room, a cozy lower-level family room, and a huge

    Darlene Winegardner RE/MAX Executive

    205 Anchor Ln, Chester, MD 21619
  • 28E Queen Mary Ct, Chester, MD 21619
    28E Queen Mary Ct, Chester, MD 21619
    28E Queen Mary Ct, Chester, MD 21619
    /34

    $365,000

    • 3 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    28E Queen Mary Ct, Chester, MD 21619

    Just painted. One more thing allowing you to move right in and enjoy life overlooking the lake!Welcome to 28E Queen Mary Court — one of the largest condos in the sought-after Queens Landing community, offering 1,660 square feet of thoughtfully designed living space. This spacious 3-bedroom, 2.5-bath home is ideally positioned to take in the best of the neighborhood, with serene lake

    Justin Disborough Samson Properties

    28E Queen Mary Ct, Chester, MD 21619
  • 208 Ringneck Ct, Chester, MD 21619
    208 Ringneck Ct, Chester, MD 21619
    208 Ringneck Ct, Chester, MD 21619
    /57

    $359,900

    • 2 Beds
    • 2.5 Baths
    • 1,747 Sq Ft

    208 Ringneck Ct, Chester, MD 21619

    NEW PRICE! 208 Ringneck Court is a great home for the smart buyer! This three-level, 2 bedroom, 2 1/2 bathroom garage town-home, located in the coveted Bayside Condominium neighborhood, was updated within the past 3 years. As you enter the south-facing home, you'll notice that the floor plan is a bit different than others...the kitchen has been reconfigured to create an open concept design

    Phyllis Endrich Long & Foster Real Estate, Inc.

    208 Ringneck Ct, Chester, MD 21619
  • 242 Peregrine Dr, Chester, MD 21619
    242 Peregrine Dr, Chester, MD 21619
    242 Peregrine Dr, Chester, MD 21619
    /36

    $715,000

    • 4 Beds
    • 3 Baths
    • 3,151 Sq Ft

    242 Peregrine Dr, Chester, MD 21619

    Introducing the Simone – Where Modern Comfort Meets Farmhouse Charm. This 6 month old Simone offers the perfect blend of open-concept living and timeless Farmhouse style with 4 spacious bedrooms, 3 full baths, and a 2-car garage, this home is designed with both functionality and flair. Step inside to find stylish laminate flooring flowing through the foyer, hallways, home office, great room,

    Pamela Owens Anchor Group Realty, LLC

    242 Peregrine Dr, Chester, MD 21619
  • 202 Ringneck Ct, Chester, MD 21619
    202 Ringneck Ct, Chester, MD 21619
    202 Ringneck Ct, Chester, MD 21619
    /72

    $364,900

    • 2 Beds
    • 2.5 Baths
    • 1,956 Sq Ft

    202 Ringneck Ct, Chester, MD 21619

    Seller New Home is Complete! Packing has started....Dont miss out, still time to enjoy summer near the water!Beautifully Updated End-Unit Townhouse in Sought-After Bayside Community!This spacious 2-bedroom, 2.5-bath end-unit townhome with a 1-car garage offers the perfect blend of comfort, style, and convenience. Step inside to discover a beautifully remodeled kitchen and updated

    Sheila Washburn Benson & Mangold, LLC

    202 Ringneck Ct, Chester, MD 21619
  • 206 Blenny Ln, Chester, MD 21619
    206 Blenny Ln, Chester, MD 21619
    206 Blenny Ln, Chester, MD 21619
    /23

    $359,900

    • 3 Beds
    • 4 Baths
    • 1,899 Sq Ft

    206 Blenny Ln, Chester, MD 21619

    Come see this town home with 1 car garage and offering 1900' of living space with interesting options on the first floor. Family room w/fp is connected to bright kitchen and sliders lead to 2nd floor deck. There are 3 Bedrooms and the Primary has a private bath with skylight. This light filled home is ready for your touches. New flooring on main level. Newer carpet on 3rd level. HVAC is

    Jimmy White Long & Foster Real Estate, Inc.

    206 Blenny Ln, Chester, MD 21619
  • 170 Harrier Way Unit 22, Chester, MD 21619
    170 Harrier Way Unit 22, Chester, MD 21619
    170 Harrier Way Unit 22, Chester, MD 21619
    /73

    $510,000

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    170 Harrier Way Unit 22, Chester, MD 21619

    For a limited time, $4000 credit towards Capital Contribution Fee for full price offer.When I asked the seller what is the best part of living here, she said......"the best things about my place is the balcony and view !! Unobstructed. No buildings directly between my unit and the river". Easy place to live !! Lock the door and leave everything to someone else !!

    Vic Pascoe Keller Williams Select Realtors of Annapolis

    170 Harrier Way Unit 22, Chester, MD 21619
  • 170 Harrier Way Unit 34, Chester, MD 21619
    170 Harrier Way Unit 34, Chester, MD 21619
    170 Harrier Way Unit 34, Chester, MD 21619
    /81

    $825,000

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    170 Harrier Way Unit 34, Chester, MD 21619

    Immediate Occupancy! No need to wait five months for a new condo to be built. And price just reduced! Welcome to luxury condo living at Four Seasons at Kent Island, an active 55+ community packed with amenities. No need to wait for a new condo to be built – you can move in now to 170 Harrier Way #34. This third floor Severn model (3 BR / 2 1⁄2 Bath / 2,602 sqft) offers beautiful views of the

    Barry Davis Long & Foster Real Estate, Inc.

    170 Harrier Way Unit 34, Chester, MD 21619
  • 1000 Herons Nest Way Unit 32, Chester, MD 21619
    1000 Herons Nest Way Unit 32, Chester, MD 21619
    1000 Herons Nest Way Unit 32, Chester, MD 21619
    /26

    $499,000

    • 2 Beds
    • 2 Baths

    1000 Herons Nest Way Unit 32, Chester, MD 21619

    Priced to Sell! Seller is ready for their next adventure! Move in, in May! Enjoy low-maintenance living in the amenity-rich, 55+ community of Four Seasons on Kent Island. This 2-bedroom, 2-bath home offers comfortable one-level living with an open layout, perfect for entertaining or relaxing. The property includes a 1-car garage with additional storage units—ideal for keeping your home organized

    Jennifer Thomas RE/MAX Executive

    1000 Herons Nest Way Unit 32, Chester, MD 21619

Showing Results 1 - 40, Page 1 of 2

Maryland Chester

Homes for Sale with Pool in Chester, MD

How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 58 homes for sale with a pool, providing a refreshing retreat and a space for leisure. Whether it's a house for sale with a pool for those warm summer days, or a property featuring an indoor or screened-in pool for year-round enjoyment, these homes offer recreation right at home. Additionally, buyers can consider properties with access to community pools, offering a convenient space for relaxation and socializing. Whether you prefer a private pool or the convenience of a community pool, browse homes for sale with a pool in Chester, MD and discover your ideal residence.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group