61

Chester, MD Homes for Sale with Pool

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  • 306 Teal Ct, Chester, MD 21619
    306 Teal Ct, Chester, MD 21619
    306 Teal Ct, Chester, MD 21619
    /24

    $279,900

    • 2 Beds
    • 2 Baths
    • 1,073 Sq Ft

    306 Teal Ct, Chester, MD 21619

    PRICE IMPROVEMENT!! Motivated Seller! Beautifully maintained first-floor condominium offering serene lake views and an open, inviting floor plan. This residence features two spacious bedrooms and two full bathrooms. The light-filled living and dining areas provide direct access to a private patio overlooking the lake, perfect for enjoying peaceful mornings. Located in a highly desirable community

    Cindy Jacobs Maryland Residential Management Co

    306 Teal Ct, Chester, MD 21619
  • 176 Flagstaff Way Unit 43, Chester, MD 21619
    176 Flagstaff Way Unit 43, Chester, MD 21619
    176 Flagstaff Way Unit 43, Chester, MD 21619
    /31

    $999,990 New Construction

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

    176 Flagstaff Way Unit 43, Chester, MD 21619

    Central island anchors the gourmet kitchen for everyday use. Home office with lited French doors add character. Dining area includes a convenient dry bar for hosting. Fireplace highlights the great room’s inviting design. Private balcony off the great room for outdoor relaxation. Owner’s suite features a generous walk-in closet. Spa-inspired owner’s bath with dual sinks & glass-enclosed shower.

    K. Hovnanian Homes Builder
    176 Flagstaff Way Unit 43, Chester, MD 21619
  • 1916 Stevens Dr, Chester, MD 21619
    1916 Stevens Dr, Chester, MD 21619
    1916 Stevens Dr, Chester, MD 21619
    /40

    $495,000

    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft

    1916 Stevens Dr, Chester, MD 21619

    Discover this beautifully updated 3-bedroom, 2 full and 1 half bathroom home located on a scenic 0.35-acre corner lot in the highly desirable Harbor View community, just two miles east of the Chesapeake Bay Bridge. Inside, enjoy a bright, modern kitchen with new countertops and backsplash, hardwood floors on the main and upstairs evels, and cathedral ceiling with skylights. Relax in the spacious

    Kimberly O'Connor Coldwell Banker Realty

    1916 Stevens Dr, Chester, MD 21619
  • 131 Flycatcher Way Unit 36471203, Chester, MD 21619
    131 Flycatcher Way Unit 36471203, Chester, MD 21619
    131 Flycatcher Way Unit 36471203, Chester, MD 21619
    /11

    $773,990 New Construction

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

    Kelly Plan at K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series, 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 Homes Builder
    131 Flycatcher Way Unit 36471203, Chester, MD 21619
  • 176 Flagstaff Way Unit 2443, Chester, MD 21619
    176 Flagstaff Way Unit 2443, Chester, MD 21619
    176 Flagstaff Way Unit 2443, Chester, MD 21619
    /52

    $999,900 New Construction

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

    176 Flagstaff Way Unit 2443, Chester, MD 21619

    The Chester at Lot 2443 offers a thoughtfully designed open-concept layout with a projected settlement date of August 2026, making it a great opportunity for buyers planning ahead. This home includes 2 bedrooms, 2.5 baths, and a 1-car garage, delivering comfort, functionality, and efficient use of space. Highlighted features include a dedicated home office with lighted French doors, a stylish dry

    Mary Anne Kowalewski KOVO Realty

    176 Flagstaff Way Unit 2443, Chester, MD 21619
  • 259 Redstart Dr, Chester, MD 21619
    259 Redstart Dr, Chester, MD 21619
    259 Redstart Dr, Chester, MD 21619
    /11

    $824,990 New Construction

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

    259 Redstart Dr, Chester, MD 21619

    Kitchen with stacked white cabinetry & glass-front uppers. Great room with fireplace creates a warm focal point. Covered patio off the great room for outdoor living. Primary suite with ceiling treatment adds refined detail. Primary bath with dual freestanding vanities. Home office tucked away for quiet work time. Second-floor loft open to the great room below.

    K. Hovnanian Homes Builder
    259 Redstart Dr, Chester, MD 21619
  • 110 Warbler Way Unit 3021, Chester, MD 21619
    110 Warbler Way Unit 3021, Chester, MD 21619
    110 Warbler Way Unit 3021, Chester, MD 21619
    /44

    $829,990 New Construction

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

    110 Warbler Way Unit 3021, Chester, MD 21619

    The Severn is thoughtfully designed for comfort and everyday entertaining, with a projected settlement of November 2026. This home offers 3 bedrooms, 2.5 baths, and a 1-car garage, all wrapped in a smart, functional layout. Inside, you’ll find stylish touches like an electric fireplace and a built-in dry bar, perfect for hosting or winding down at home. The owner’s suite is a true retreat,

    Mary Anne Kowalewski KOVO Realty

    110 Warbler Way Unit 3021, Chester, MD 21619
  • 131 Flycatcher Way Unit 36492116, Chester, MD 21619
    131 Flycatcher Way Unit 36492116, Chester, MD 21619
    131 Flycatcher Way Unit 36492116, Chester, MD 21619
    /12

    $599,990 New Construction

    • 2 Beds
    • 2 Baths
    • 1,690 Sq Ft

    Bernstein II Plan at K. Hovnanian’s® Four Seasons at Kent Island - 35' River Series, 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 bath. Laundry room and HovHall with plenty of space to store and organize.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36492116, Chester, MD 21619
  • 8 Queen Victoria Way, Chester, MD 21619
    8 Queen Victoria Way, Chester, MD 21619
    8 Queen Victoria Way, Chester, MD 21619
    /46

    $369,900

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

    8 Queen Victoria Way, Chester, MD 21619

    Beautifully upgraded 2.5 story townhouse ideally located directly across from the community marina and close to the clubhouse, offering exceptional convenience for boat owners and resort style living. The main level features a bright open living area with ceramic flooring that complements the home’s coastal style and blends seamlessly with the wood-burning fireplace. Sliding doors open to a

    Julia Stevens Realty Navigator

    8 Queen Victoria Way, Chester, MD 21619
  • 132 Wheelhouse Way, Chester, MD 21619
    132 Wheelhouse Way, Chester, MD 21619
    132 Wheelhouse Way, Chester, MD 21619
    /68

    $1,299,990 New Construction

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

    132 Wheelhouse Way, Chester, MD 21619

    This beautifully designed Chester Model Home offers sophisticated comfort and modern convenience, ready for immediate move-in with a flexible month-to-month leaseback opportunity. Featuring 2 bedrooms, 2.5 baths, and a 1-car garage, this home blends style and function seamlessly. Thoughtful touches include a fully furnished interior, a dry bar perfect for entertaining, and an electric fireplace

    Mary Anne Kowalewski KOVO Realty

    132 Wheelhouse Way, Chester, MD 21619
  • 131 Flycatcher Way Unit 36503530, Chester, MD 21619
    131 Flycatcher Way Unit 36503530, Chester, MD 21619
    131 Flycatcher Way Unit 36503530, Chester, MD 21619
    /21

    $579,990 New Construction

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

    Severn Plan at K. Hovnanian’s® Four Seasons at Kent Island - Luxury Condos, 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 Homes Builder
    131 Flycatcher Way Unit 36503530, Chester, MD 21619
  • 110 Boatswain Way Unit 21, Chester, MD 21619
    110 Boatswain Way Unit 21, Chester, MD 21619
    110 Boatswain Way Unit 21, Chester, MD 21619
    /18

    $829,990 New Construction

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

    110 Boatswain Way Unit 21, Chester, MD 21619

    Gourmet kitchen with spacious central island. Dining area includes a convenient dry bar. Great room features an electric fireplace. Beautiful balcony extends off of the great room. Owner’s suite with dual walk-in closets. Private sitting room with balcony access. Luxurious owner’s bath with dual sinks.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 21, Chester, MD 21619
  • 176 Flagstaff Way Unit 11, Chester, MD 21619
    176 Flagstaff Way Unit 11, Chester, MD 21619
    176 Flagstaff Way Unit 11, Chester, MD 21619
    /9

    $649,990 New Construction

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

    176 Flagstaff Way Unit 11, Chester, MD 21619

    Gourmet kitchen featuring designer cabinetry & center island. Spacious great room with electric fireplace. Inviting dining area featuring lovely dry bar. Pristine owner's suite & spa bath with walk-in closet. Versatile outdoor patio, perfect for spending time with friends. Productive home office with lited double doors. Functional laundry room for added convenience.

    K. Hovnanian Homes Builder
    176 Flagstaff Way Unit 11, Chester, MD 21619
  • 110 Warbler Way Unit 3034, Chester, MD 21619
    110 Warbler Way Unit 3034, Chester, MD 21619
    110 Warbler Way Unit 3034, Chester, MD 21619
    /44

    $979,990 New Construction

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

    110 Warbler Way Unit 3034, Chester, MD 21619

    The Severn combines an open floorplan with thoughtful design elements, with a projected settlement date of November 2026. Designed for comfortable and modern living, this home features 3 bedrooms, 2.5 baths, and a 1-car garage. The owner’s suite includes a sitting room, large walk-in closets, and a spa-inspired bath with a shower featuring a seat and handheld shower wand, double sinks, and quartz

    Mary Anne Kowalewski KOVO Realty

    110 Warbler Way Unit 3034, Chester, MD 21619
  • 117 Flycatcher Way, Chester, MD 21619
    117 Flycatcher Way, Chester, MD 21619
    117 Flycatcher Way, Chester, MD 21619
    /49

    $1,400,000 New Construction

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

    117 Flycatcher Way, Chester, MD 21619

    The Franklin Model Home offers a beautifully designed open-concept layout enriched with elevated designer finishes—available now for immediate settlement with a rent-back opportunity. With 3 bedrooms, 3.5 baths, and a 2-car garage, this home provides a refined blend of comfort, versatility, and modern style. Standout features include a dedicated home office, a cozy fireplace, and a screened patio

    Mary Anne Kowalewski KOVO Realty

    117 Flycatcher Way, Chester, MD 21619
  • 123 Flycatcher Way, Chester, MD 21619
    123 Flycatcher Way, Chester, MD 21619
    123 Flycatcher Way, Chester, MD 21619
    /24

    $1,389,667 New Construction

    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft

    123 Flycatcher Way, Chester, MD 21619

    Well-equipped kitchen with stacked dark stained cabinetry & glass uppers. Cozy fireplace adds warmth & character to spacious great room. Tranquil primary suite with generous walk-in closet. Productive home office for studying or reading. Private Extra Suite, great for overnight guests. Inviting screened patio for outdoor entertaining. Second floor loft provide addtionial living space.

    K. Hovnanian Homes Builder
    123 Flycatcher Way, Chester, MD 21619
  • 110 Warbler Way Unit 3033, Chester, MD 21619
    110 Warbler Way Unit 3033, Chester, MD 21619
    110 Warbler Way Unit 3033, Chester, MD 21619
    /52

    $789,990 New Construction

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

    110 Warbler Way Unit 3033, Chester, MD 21619

    The Chester offers a thoughtfully designed open floorplan with a projected settlement date of October 2026. Ideal for modern living, this home features 2 bedrooms, 2.5 baths, and a 1-car garage. The main living area is anchored by an electric fireplace, while a dry bar adds both function and style for entertaining. A dedicated home office with lighted French doors provides a flexible space

    Mary Anne Kowalewski KOVO Realty

    110 Warbler Way Unit 3033, Chester, MD 21619
  • 3000 Herons Nest Way Unit 11, Chester, MD 21619
    3000 Herons Nest Way Unit 11, Chester, MD 21619
    3000 Herons Nest Way Unit 11, Chester, MD 21619
    /66

    $555,900

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

    3000 Herons Nest Way Unit 11, Chester, MD 21619

    Love Where You Live! Experience resort-style living that blends comfort, luxury, and convenience—just steps from the waterfront. Enjoy peaceful mornings without the disruption of construction nearby. This highly sought-after first-floor condo is move-in ready and has been meticulously maintained, featuring numerous upgrades throughout. Step inside to an open, light-filled layout enhanced by crown

    John Freeman Coldwell Banker Realty

    3000 Herons Nest Way Unit 11, 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
    /18

    $465,000

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

    15 Queen Anne Way Unit E, Chester, MD 21619

    PRICE DROP! Motivated Seller! Escape to the water — without the waterfront price. This Chester River–front townhome in Queens Landing is the perfect second home or low-maintenance retreat, all for under $500K. Enjoy sunrise water views from your private patio and balcony, and lock-and-leave peace of mind when you head back home. Inside, the layout is easy and functional with luxury vinyl plank

    Jennifer Thomas RE/MAX Executive

    15 Queen Anne Way Unit E, Chester, MD 21619
  • 131 Flycatcher Way Unit 36455262, Chester, MD 21619
    131 Flycatcher Way Unit 36455262, Chester, MD 21619
    131 Flycatcher Way Unit 36455262, Chester, MD 21619
    /16

    $883,990 New Construction

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

    Munich ESP Plan at K. Hovnanian’s® Four Seasons at Kent Island - 60' Island Series, 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. Large covered patio for enjoying the outdoors.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36455262, Chester, MD 21619
  • 528 Warbler Way, Stevensville, MD 21666
    528 Warbler Way, Stevensville, MD 21666
    528 Warbler Way, Stevensville, MD 21666
    /29

    $799,500 Open Sun 10AM - 12PM

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

    528 Warbler Way, Stevensville, MD 21666

    Like-new luxury living in Four Seasons at Kent Island.Completed in August and only lightly lived in, this 2,800 sq ft home offers 4 bedrooms and 3 baths with a pristine, move-in-ready feel. Highlights include luxury vinyl plank flooring, quartz countertops, and over $20,000 in custom window treatments, can you say "plantation shutters". Professionally decorated throughout—with the option to

    Jennifer Thomas RE/MAX Executive

    528 Warbler Way, Stevensville, MD 21666

Showing Results 41 - 61, Page 2 of 2

Maryland Queen Annes County Chester

Homes for Sale with Pool in Chester, MD

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In Chester, there are currently 61 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.

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