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Chester, MD Homes for Sale with Pool

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  • 47 D Queen Anne Way, Chester, MD 21619
    47 D Queen Anne Way, Chester, MD 21619
    47 D Queen Anne Way, Chester, MD 21619
    /45

    $598,000 Open House 9/28

    • 2 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    47 D Queen Anne Way, Chester, MD 21619

    Enjoy resort style living every day in the gorgeous waterfront condo. 42' boat slip w/ water/electric & 25K lb magnum lift conveys - WOW!! Watch the sun & moon rise as you sip your favorite beverage or entertain as everyone will want to come visit you now. Professional pics coming soon. This sought after townhome/condo has extensive view of the Chester River & Eastern Neck Island. The owner has

    Agent Photo

    Brenda Fornos

    Taylor Properties

    (410) 623-7650

    47 D Queen Anne Way, Chester, MD 21619
  • 131 Flycatcher Way Unit 36469043, Chester, MD 21619
    131 Flycatcher Way Unit 36469043, Chester, MD 21619
    131 Flycatcher Way Unit 36469043, Chester, MD 21619
    /26

    $811,900 New Construction

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

    Kerr Plan at K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series, 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.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36469043, Chester, MD 21619
  • 131 Flycatcher Way Unit 36476268, Chester, MD 21619
    131 Flycatcher Way Unit 36476268, Chester, MD 21619
    131 Flycatcher Way Unit 36476268, Chester, MD 21619
    /40

    $840,900 New Construction

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

    Tuscaloosa Plan at K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series, 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.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36476268, Chester, MD 21619
  • 131 Flycatcher Way Unit 36493007, Chester, MD 21619
    131 Flycatcher Way Unit 36493007, Chester, MD 21619
    131 Flycatcher Way Unit 36493007, Chester, MD 21619
    /12

    $474,990 New Construction

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

    Magothy Plan at K. Hovnanian’s® Four Seasons at Kent Island - Luxury Condos, 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 inclusive of an average location premium.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36493007, Chester, MD 21619
  • 131 Flycatcher Way Unit 36474700, Chester, MD 21619
    131 Flycatcher Way Unit 36474700, Chester, MD 21619
    131 Flycatcher Way Unit 36474700, Chester, MD 21619
    /10

    $744,900 New Construction

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

    Taylor Plan at K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series, 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.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36474700, Chester, MD 21619
  • 131 Flycatcher Way Unit 36477689, Chester, MD 21619
    131 Flycatcher Way Unit 36477689, Chester, MD 21619
    131 Flycatcher Way Unit 36477689, Chester, MD 21619
    /12

    $876,900 New Construction

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

    Mykonos Plan at K. Hovnanian’s® Four Seasons at Kent Island - 60' Island Series, 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 storage.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36477689, 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

    $415,000

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

    54A Queen Caroline Ct, Chester, MD 21619

    Price Improvement...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, stainless steel

    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
    /71

    $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
  • 131 Flycatcher Way Unit 36451844, Chester, MD 21619
    131 Flycatcher Way Unit 36451844, Chester, MD 21619
    131 Flycatcher Way Unit 36451844, Chester, MD 21619
    /27

    $848,900 New Construction

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

    Franklin Plan at K. Hovnanian’s® Four Seasons at Kent Island - 60' Island Series, 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.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36451844, Chester, MD 21619
  • 131 Flycatcher Way Unit 36466218, Chester, MD 21619
    131 Flycatcher Way Unit 36466218, Chester, MD 21619
    131 Flycatcher Way Unit 36466218, Chester, MD 21619
    /24

    $663,900 New Construction

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

    Jenkins II Plan at K. Hovnanian’s® Four Seasons at Kent Island - River Series, 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.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36466218, Chester, MD 21619
  • 141 Switchgrass Way Unit 34, Chester, MD 21619
    141 Switchgrass Way Unit 34, Chester, MD 21619
    141 Switchgrass Way Unit 34, Chester, MD 21619
    /61

    $684,950

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

    141 Switchgrass Way Unit 34, Chester, MD 21619

    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, 2.5 bath end-unit boasting an expansive open floor plan with over 2600 square feet of luxurious living space. This home features a lavish gourmet kitchen

    Ralph Kennedy RE/MAX Executive

    141 Switchgrass Way Unit 34, Chester, MD 21619
  • 2865 Cox Neck Rd, Chester, MD 21619
    2865 Cox Neck Rd, Chester, MD 21619
    2865 Cox Neck Rd, Chester, MD 21619
    /38

    $2,259,000

    • 4 Beds
    • 3.5 Baths
    • 5,122 Sq Ft

    2865 Cox Neck Rd, Chester, MD 21619

    An impressive open two-story foyer welcomes you to this custom 4 BR, 3.5BA waterfront residence on 1.9 acres boasting an enchanting open space floorplan. A first floor Ensuite BR has a walk-in closet plus a separate jacuzzi and shower in the updated full bath. The sumptuous approximately 39'X26' Primary Suite with a large sitting room area offers front and rear balconies specifically designed by

    Michele Sinclair Long & Foster Real Estate, Inc.

    2865 Cox Neck Rd, Chester, MD 21619
  • 130 Sunrise Ct, Chester, MD 21619
    130 Sunrise Ct, Chester, MD 21619
    130 Sunrise Ct, Chester, MD 21619
    /80

    $949,900

    • 3 Beds
    • 4 Baths
    • 3,494 Sq Ft

    130 Sunrise Ct, Chester, MD 21619

    Welcome to Four Seasons at Kent Island, where luxury and comfort meet coastal living. This stunning Santorini model at the end of a cul-de-sac with loft offers 3 bedrooms, 4 full baths, and thoughtfully curated designer upgrades throughout. From the moment you step inside, you’ll feel the ease of open-concept living — soaring 10’ ceilings, cozy gas fireplace, abundant natural light, neutral color

    Meg Richardson Engel & Völkers Annapolis

    130 Sunrise Ct, Chester, MD 21619
  • 132 Kestrel Ln, Chester, MD 21619
    132 Kestrel Ln, Chester, MD 21619
    132 Kestrel Ln, Chester, MD 21619
    /45

    $1,049,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 3.5 Baths
    • 3,634 Sq Ft

    132 Kestrel Ln, Chester, MD 21619

    Welcome to 132 Kestrel Lane, an exceptional home in the premier waterfront community of Four Seasons at Kent Island. Offering over 3,600 square feet of thoughtfully designed living space, this residence combines elegant design, modern functionality, and a lifestyle centered around comfort, connection, and the natural beauty of the Chesapeake Bay.From the moment you arrive, the covered

    Brad Kappel TTR Sotheby's International Realty

    132 Kestrel Ln, Chester, MD 21619
  • 200 Harrier Way Unit 21, Chester, MD 21619
    200 Harrier Way Unit 21, Chester, MD 21619
    200 Harrier Way Unit 21, Chester, MD 21619
    /44

    $699,900

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

    200 Harrier Way Unit 21, Chester, MD 21619

    Welcome to Luxury Condo Living at The Four Seasons at Kent Island, An active 55+ Community packed with tons of amenities . Move -in to this turn key luxury condo with plenty of natural light with "Perfect Fit" planation shutters and ample privacy on all windows and doors. The kitchen has a gourmet package including quartz countertops and a large island with space for barstool eating, subway

    shannon Gompers Long & Foster Real Estate, Inc.

    200 Harrier Way Unit 21, Chester, MD 21619
  • 108 Bodys Neck Rd, Chester, MD 21619
    108 Bodys Neck Rd, Chester, MD 21619
    108 Bodys Neck Rd, Chester, MD 21619
    /49

    $499,900

    • 3 Beds
    • 2.5 Baths
    • 1,791 Sq Ft

    108 Bodys Neck Rd, Chester, MD 21619

    Resort-Style Island Living with Unmatched Water Views!Discover the perfect blend of coastal charm and modern luxury in this rarely available, oversized end-unit townhome Perfectly positioned to capture water views and marina, this meticulously updated 3-bedroom, 2.5-bath home offers a true resort-style experience in one of the Eastern Shore’s most desirable locations.Step inside

    Bill Longest Realty Navigator

    108 Bodys Neck Rd, Chester, MD 21619
  • 124 Nauset Ln, Chester, MD 21619
    124 Nauset Ln, Chester, MD 21619
    124 Nauset Ln, Chester, MD 21619
    /45

    $847,500

    • 3 Beds
    • 3 Baths
    • 2,583 Sq Ft

    124 Nauset Ln, Chester, MD 21619

    NEW UPDATED PHOTOS!! Take another look!Turnkey Luxury with Over $175K in Upgrades – Four Seasons at Kent IslandThis beautifully enhanced Killarney with Loft model in Phase I offers the ultimate in resort-style living, featuring over $100K in builder upgrades and $75K in custom renovations. To build this home new through the builder would be over 1 million dollars. For added peace

    Jennifer Thomas RE/MAX Executive

    124 Nauset Ln, Chester, MD 21619
  • 104 Woods Rd, Chester, MD 21619
    104 Woods Rd, Chester, MD 21619
    104 Woods Rd, Chester, MD 21619
    /38

    $800,000 Open Sun 11AM - 1PM

    • 5 Beds
    • 3.5 Baths
    • 3,065 Sq Ft

    104 Woods Rd, Chester, MD 21619

    OPEN SUNDAY 9/21/25 11;00AM -1:00PM PERFECT MULTI GENERATIONAL HOME!!!! LIST PRICE ADJUSTED !!FANTASTIC HOME! THE COMPLETE PACKAGE AND THEN MORE! INGROUND POOL! TWO PRIMARY BEDROOM/BATH SUITES! BOTH WITH GIANT WALK IN CLOSETS! EACH PRIMARY BATH HAS A STEP IN SHOWER, DOUBLE STONE VANITY PLUS SOAKING TUB! THIS HOME HAS A TOTAL OF 5 BEDROOMS PLUS 3 AND ONE HALF BATHS! PLENTY OF SPACE FOR THE

    Temple Peirce Cummings & Co. Realtors

    104 Woods Rd, Chester, MD 21619
  • 314 Thomas White Blvd, Chester, MD 21619
    314 Thomas White Blvd, Chester, MD 21619
    314 Thomas White Blvd, Chester, MD 21619
    /73

    $769,000

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

    314 Thomas White Blvd, Chester, MD 21619

    Open Sunday 11-1PM WOW! This is your opportunity to get into this sought after community for UNDER $800k! Welcome to 314 Thomas White Blvd. Nestled in the sought-after waterfront community of Gibson’s Grant, this 4-bedroom, 3.5-bath home offers the perfect blend of refined living and relaxed coastal comfort. You will fall in love with the inviting front porch to the detached garage with the 4th

    Kathleen Higginbotham Keller Williams Flagship

    314 Thomas White Blvd, 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 1:30PM - 3:30PM

    • 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
  • 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
  • 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
  • 807 Auckland Way, Chester, MD 21619
    807 Auckland Way, Chester, MD 21619
    807 Auckland Way, Chester, MD 21619
    /34

    $482,090

    • 3 Beds
    • 3.5 Baths
    • 2,100 Sq Ft

    807 Auckland Way, Chester, MD 21619

    PRICE REDUCED! Waterside Living on Kent Island! Discover the perfect blend of comfort and convenience in this spacious 3-bedroom, 3.5-bathroom condo located on Kent Island, in the Bayside Condominiums waterside community. This 3-level condo offers a wonderful combination of space, style, and serene coastal living.The open-concept main floor features a freshly painted, inviting living

    Andrew Spagnolo Samson Properties

    807 Auckland Way, 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

    $574,900 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.

    Builder Photo

    K. Hovnanian Homes

    Builder

    630 Warbler Way Unit 22, Chester, MD 21619
  • 630 Warbler Way Unit 12, Chester, MD 21619
    630 Warbler Way Unit 12, Chester, MD 21619
    630 Warbler Way Unit 12, Chester, MD 21619
    /8

    $549,900 New Construction

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

    630 Warbler Way Unit 12, Chester, MD 21619

    Charming gourmet kitchen featuring center island & ample counter space. Electric fireplace adds warmth to spacious great room. Refined dining area with dry bar. Functional home office for studying or reading. Private owner's suite & spa bath with walk-in closet. Versatile covered patio for outdoor relaxation.

    Builder Photo

    K. Hovnanian Homes

    Builder

    630 Warbler Way Unit 12, Chester, MD 21619
  • 519 Warbler Way, Chester, MD 21619
    519 Warbler Way, Chester, MD 21619
    519 Warbler Way, Chester, MD 21619
    /20

    $919,900 New Construction

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

    519 Warbler Way, Chester, MD 21619

    Convenient Extra Suite for guests to stay overnight. Functional home office off foyer for working from home. Breathtaking kitchen with Winstead Maple Flagstone cabinetry. Beautiful Calacatta Abezzo quartz countertops & island. Refined great room & equisite fireplace. Intimate dining area for hosting dinner parties. Private primary suite & spa-like bath with dual vanities. Stunning screened patio

    Builder Photo

    K. Hovnanian Homes

    Builder

    519 Warbler Way, Chester, MD 21619
  • 630 Warbler Way Unit 2222, Chester, MD 21619
    630 Warbler Way Unit 2222, Chester, MD 21619
    630 Warbler Way Unit 2222, Chester, MD 21619
    /48

    $574,900 New Construction

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

    630 Warbler Way Unit 2222, Chester, MD 21619

    Chester|| Available May 2026This home offers 2 bedrooms, 2.5 baths, and a 1-car garage. Standout features include a dry bar, an electric fireplace, and a dedicated home office with lited French doors. The kitchen is thoughtfully designed with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lights, and a tile backsplash, all accented by quartz countertops.The

    Mary Anne Kowalewski KOVO Realty

    630 Warbler Way Unit 2222, 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

    $766,900 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.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36471203, 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
    /12

    $873,900 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

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36455262, 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

    $559,990 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.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36503530, Chester, MD 21619
  • 312 Teal Ct Unit F, Chester, MD 21619
    312 Teal Ct Unit F, Chester, MD 21619
    312 Teal Ct Unit F, Chester, MD 21619
    /42

    $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
  • 224 Bayberry Dr, Chester, MD 21619
    224 Bayberry Dr, Chester, MD 21619
    224 Bayberry Dr, Chester, MD 21619
    /51

    $610,000

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

    224 Bayberry Dr, Chester, MD 21619

    Welcome to Easy Living on the Eastern Shore! ***Discover the perfect blend of comfort, style, and resort-style living in this impeccably maintained, one-owner home — tucked into the highly sought-after, water-privileged 55+ community of Four Seasons at Kent Island.From the moment you walk in, you’ll notice the difference. The open-concept floor plan is thoughtfully designed and

    Petra Quinn Realty Navigator

    224 Bayberry Dr, Chester, MD 21619
  • 9B Queen Victoria Way, Chester, MD 21619
    9B Queen Victoria Way, Chester, MD 21619
    9B Queen Victoria Way, Chester, MD 21619
    /48

    $425,000

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

    9B Queen Victoria Way, Chester, MD 21619

    This 1680 sq ft , 2 1/2 story townhome & this community have it all! It features many updates within the last year, and it shows beautifully! It is "move-in ready",!.. The updates include a new main-level half bath & a new full bathroom on the top level, both have new flooring, ADA-compliant toilets, new vanity/sink & faucets, and paint. Interior doors are 6 panel colonial replaced in

    Melanie Mcknight RE/MAX Professionals

    9B Queen Victoria Way, 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
  • 49 Queen Guinivere Way, Chester, MD 21619
    49 Queen Guinivere Way, Chester, MD 21619
    49 Queen Guinivere Way, Chester, MD 21619
    /79

    $519,500

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

    49 Queen Guinivere Way, Chester, MD 21619

    PRICE IMPROVEMENT!! 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

    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

    $499,000

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

    15 Queen Anne Way Unit E, Chester, MD 21619

    The BIGGEST price drop yet!! 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 flooring, and access to a

    Julia Stevens Realty Navigator

    15 Queen Anne Way Unit E, 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
  • 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

    $795,000

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

    170 Harrier Way Unit 34, Chester, MD 21619

    Open House this Sunday 9/14 from 12-2. New improved price of $795,000 and immediate occupancy! This is the only 3 bedroom condo on the market in Four Seasons with the immediate availability. The other two will not be ready until February 2026. 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 –

    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 Queen Annes County Chester

Homes for Sale with Pool in Chester, MD

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 42 days on the market compared to the national average of 52 days. The median sale price for homes in Chester, MD over the last 12 months is $602,400, up 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$602,400
Median Single Family Sale Price
$639,900
Median Townhouse Sale Price
$420,000
Median 2 Bedroom Sale Price
$514,750
Median 1 Bedroom Sale Price
$306,500
Average Price Per Sq Ft
$294
Number of Homes for Sale
62
Last 12 months Home Sales
178
Months of Supply
4.20
Median List Price
$595,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
4%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 51 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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