55

Chester, MD Homes for Sale with Pool

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  • 312 Teal Ct Unit F, Chester, MD 21619
    312 Teal Ct Unit F, Chester, MD 21619
    312 Teal Ct Unit F, Chester, MD 21619
    /40

    $305,000

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

    312 Teal Ct Unit F, Chester, MD 21619

    This is a highly sought-after location on Kent Island, known for its limited availability.Sellers have updated shiplap in the living room, paint throughout the house. This second-floor condo offers breathtaking views of the pond. You will enjoy an updated backsplash in the kitchen, featuring granite countertops and stainless steel appliances. Hardwood flooring is throughout the house. The

    Mary Rice Engel & Völkers Ocean City

    312 Teal Ct Unit F, Chester, MD 21619
  • 201 Golden Eye Ct, Chester, MD 21619
    201 Golden Eye Ct, Chester, MD 21619
    201 Golden Eye Ct, Chester, MD 21619
    /50

    $285,000

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

    201 Golden Eye Ct, Chester, MD 21619

    Welcome to this bright and inviting 2-bedroom, 2-bathroom lower-level end unit condo, ideally located in a desirable water-oriented community on Kent Island! The open living and dining area flows seamlessly into a galley-style kitchen with a breakfast bar, now updated with new granite countertops and a new stainless steel stove. The Primary suite is your private retreat, complete with a walk-in

    Melissa Tippett TTR Sotheby's International Realty

    201 Golden Eye Ct, 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,

    Lona Todd Taylor Properties

    34 Queen Anne Way, Chester, MD 21619
  • 10 B Queen Elizabeth Ct, Chester, MD 21619
    10 B Queen Elizabeth Ct, Chester, MD 21619
    10 B Queen Elizabeth Ct, Chester, MD 21619
    /19

    $330,000

    • 1 Bed
    • 1 Bath
    • 724 Sq Ft

    10 B Queen Elizabeth Ct, Chester, MD 21619

    WATERFRONT !!! Spectacular sunrise views on display over the Chester River from this cozy 1 bedroom, 1 bath condo in the popular community of Queens Landing. Known for its amenities, you are sure to enjoy living here whether as a full-time resident or just to have as a week-end getaway! Minutes from the Bay Bridge, you can be here without ever getting on route 50!Amenities are as follows:

    Mary Stevens Long & Foster Real Estate, Inc.

    10 B Queen Elizabeth Ct, Chester, MD 21619
  • 109 John Gibson Dr, Chester, MD 21619
    109 John Gibson Dr, Chester, MD 21619
    109 John Gibson Dr, Chester, MD 21619
    /78

    $915,000

    • 6 Beds
    • 4.5 Baths
    • 4,165 Sq Ft

    109 John Gibson Dr, Chester, MD 21619

    Start the New Year as a resident of Gibson’s Grant!Discover over 4,100 sq. ft. of high-end, custom elegance in this exceptional Eastern Shore home—perfectly located in one of Chester’s most sought-after waterfront communities. With 6 bedrooms, 4.5 baths, and designer touches at every turn, this residence offers the space, craftsmanship, and lifestyle today’s buyers crave.Step inside the

    Lisa Barton Coldwell Banker Realty

    109 John Gibson Dr, 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

    $574,990 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
  • 630 Warbler Way Unit 22, Chester, MD 21619
    630 Warbler Way Unit 22, Chester, MD 21619
    630 Warbler Way Unit 22, Chester, MD 21619
    /21

    $565,990 New Construction

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

    630 Warbler Way Unit 22, Chester, MD 21619

    Functional home office with elegant French doors. Beautiful gourmet kitchen with pendant lighting. Spacious dining area and great room with electric fireplace. Palatial owner's suite with triple windows & balcony access. Glamorous owner's spa bath featuring split vanities. Beautiful balcony for outdoor enjoyment.

    K. Hovnanian Homes Builder
    630 Warbler Way Unit 22, Chester, MD 21619
  • 2907 Cox Neck Rd E, Chester, MD 21619
    2907 Cox Neck Rd E, Chester, MD 21619
    2907 Cox Neck Rd E, Chester, MD 21619
    /43

    $1,899,000

    • 4 Beds
    • 6 Baths
    • 3,460 Sq Ft

    2907 Cox Neck Rd E, Chester, MD 21619

    Set within Southwind, one of Kent Island’s most sought-after waterfront communities, this exceptional residence offers an elegant blend of craftsmanship and comfort with 10 foot ceilings and beautiful crown molding. Perfectly sited on an acre overlooking Crab Alley Bay and Eastern Bay, the home’s peaceful setting is enhanced by sweeping water views, mature landscaping, and a private waterside

    Brad Kappel TTR Sotheby's International Realty

    2907 Cox Neck Rd E, 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
  • 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
    /15

    $480,000 Open House 1/03

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

    15 Queen Anne Way Unit E, Chester, MD 21619

    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 flooring, a gas fireplace, and a

    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
  • 527 Warbler Way, Stevensville, MD 21666
    527 Warbler Way, Stevensville, MD 21666
    527 Warbler Way, Stevensville, MD 21666
    /45

    $799,990 Open Sat 11AM - 4PM

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

    527 Warbler Way, Stevensville, MD 21666

    Ready NOW! This stunning Kerr home offers an inviting open floor plan designed for both comfort and functionality. Featuring 3 bedrooms, 3 baths, and a spacious 3-car garage, this home perfectly blends everyday ease with elevated style. Highlights include a dedicated home office, a cozy screened patio for outdoor relaxation, and a dramatic 2-story stone fireplace that serves as the heart of the

    Mary Anne Kowalewski KOVO Realty

    527 Warbler Way, Stevensville, MD 21666

Showing Results 41 - 55, 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 55 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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