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Explore Similar Homes Within 25 Miles of Chestertown, MD

  • 16 Lexie Ct, Dover, DE 19904
    16 Lexie Ct, Dover, DE 19904
    16 Lexie Ct, Dover, DE 19904
    /65

    $398,900

    • 2 Beds
    • 2 Baths
    • 1,444 Sq Ft

    16 Lexie Ct, Dover, DE 19904

    Welcome to this thoughtfully designed 2-bedroom, 2-bath home perfectly situated on a corner lot in the highly desirable Noble’s Pond community. From the moment you arrive, you’ll see that every detail has been carefully considered to create a home that is both functional and inviting. The primary suite is a true retreat, featuring a tray ceiling, a large walk-in closet, and a spacious,

    Agent Photo

    Patricia Haney

    Century 21 Home Team Realty

    (302) 271-6241

    16 Lexie Ct, Dover, DE 19904
  • 225 Opera Ct, Centreville, MD 21617
    225 Opera Ct, Centreville, MD 21617
    225 Opera Ct, Centreville, MD 21617
    /41

    $499,900

    • 3 Beds
    • 2 Baths
    • 2,274 Sq Ft

    225 Opera Ct, Centreville, MD 21617

    Come fall in love with this amazing sought after 55+ community of Symphony Village with tons of amenities & activities. Enjoy having solar with super low $118 a month electric bills! Wonderful location yet close to hospitals, doctors, shopping, restaurants, beaches, parks, boat ramps & more. Gorgeous custom 3BR, 2BA rancher with stunning hardwood floors and lots of upgrades. New roof only 3 years

    Agent Photo

    Brenda Fornos

    Taylor Properties

    (410) 734-3652

    225 Opera Ct, Centreville, MD 21617
  • 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
    /70

    $560,000

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

    4000 Herons Nest Way Unit 22, Chester, MD 21619

    ** New Listing! Four Seasons @ Kent Island - 55+ Community - Turnkey & 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 with quartz counters, propane

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    (410) 390-0346

    4000 Herons Nest Way Unit 22, Chester, MD 21619
  • 135 Nauset Ln, Chester, MD 21619
    135 Nauset Ln, Chester, MD 21619
    135 Nauset Ln, Chester, MD 21619
    /81

    $814,900

    • 3 Beds
    • 3 Baths
    • 2,795 Sq Ft

    135 Nauset Ln, Chester, MD 21619

    If you’ve ever dreamed of waking up and feeling like you’re on vacation—but with the comforts of home—welcome to 135 Nauset Lane. Tucked into a quiet corner of Kent Island’s Four Seasons community, this home isn’t just beautiful—it’s part of a lifestyle that’s hard to find and even harder to leave. The sellers were first drawn here by the energy of the community and the resort-style amenities.

    Agent Photo

    Riley White

    Real Broker, LLC - Annapolis

    (667) 295-8334

    135 Nauset Ln, Chester, MD 21619
  • 209 Lupine Dr, Smyrna, DE 19977
    209 Lupine Dr, Smyrna, DE 19977
    209 Lupine Dr, Smyrna, DE 19977
    /31

    $455,000

    • 2 Beds
    • 2 Baths
    • 1,762 Sq Ft

    209 Lupine Dr, Smyrna, DE 19977

    Welcome to easy, low-maintenance living in this desirable 55+ community—where comfort, convenience, and peace of mind come together beautifully!***Enjoy the freedom of a lifestyle where the HOA takes care of lawn maintenance and snow removal (including sidewalks, streets, and driveway)—giving you more time to relax and do what you love. ***And with a low HOA fee, it’s the perfect blend of value

    Agent Photo

    Doreen Sawchak

    RE/MAX Associates-Hockessin

    (302) 495-5598

    209 Lupine Dr, Smyrna, DE 19977
  • 198 Indigo Cir, Smyrna, DE 19977
    198 Indigo Cir, Smyrna, DE 19977
    198 Indigo Cir, Smyrna, DE 19977
    /39

    $168,750

    • 3 Beds
    • 2 Baths
    • 1,428 Sq Ft

    198 Indigo Cir, Smyrna, DE 19977

    Looking for an affordable, new home without the wait? Here's your chance! This home is less than 3 years young, in the quiet 55+, highly secluded rear section of Ridgewood Manor, just off of Rt 13 and close to shopping & healthcare. The corner, premium lot features a custom ordered 14x10 shed to perfectly match the home. Sit back and relax with your morning coffee on the low-maintenance front

    Agent Photo

    Jenna LaFermine

    Burns & Ellis Realtors

    (302) 305-5487

    198 Indigo Cir, Smyrna, DE 19977
  • 714 Harmony Way, Centreville, MD 21617
    714 Harmony Way, Centreville, MD 21617
    714 Harmony Way, Centreville, MD 21617
    /47

    $540,000 Open Thu 5PM - 7PM

    • 4 Beds
    • 3 Baths
    • 2,804 Sq Ft

    714 Harmony Way, Centreville, MD 21617

    Nestled within the award-winning Symphony Village active adult community, this stunning contemporary residence offers a luxurious lifestyle tailored for those seeking comfort and elegance. Strategically priced and designed with an age requirement in mind, this home is a sanctuary of tranquility and sophistication, perfect for enjoying the finer things in life. Spanning an impressive 2,804 square

    Agent Photo

    Deborah Shiley

    Long & Foster Real Estate, Inc.

    (410) 873-7404

    714 Harmony Way, Centreville, MD 21617
  • 1415 Pennfield Dr Unit 36482401, Middletown, DE 19709
    1415 Pennfield Dr Unit 36482401, Middletown, DE 19709
    1415 Pennfield Dr Unit 36482401, Middletown, DE 19709
    /29

    $639,990 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,493 Sq Ft

    Carver Plan at K. Hovnanian’s® Four Seasons at Pennfield, Middletown, DE 19709

    Foyer with ceiling treatment welcoming you home. Private home office with barn doors, perfect for telecommuting. Spacious great room and dining area with vaulted ceiling. Striking kitchen with lots of counterspace and large pantry. Secluded primary suite with ceiling treatment and walk-in closet. Luxurious primary bath with freestanding vanities and large shower.

    K. Hovnanian Homes Builder
    1415 Pennfield Dr Unit 36482401, Middletown, DE 19709
  • 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

    $752,990 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.

    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

    $886,990 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.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36477689, Chester, MD 21619
  • 1415 Pennfield Dr Unit 36502364, Middletown, DE 19709
    1415 Pennfield Dr Unit 36502364, Middletown, DE 19709
    1415 Pennfield Dr Unit 36502364, Middletown, DE 19709
    /12

    $499,990 New Construction

    • 3 Beds
    • 2 Baths
    • 1,811 Sq Ft

    Asheville Plan at K. Hovnanian’s® Four Seasons at Pennfield, Middletown, DE 19709

    Modern kitchen with large island, walk-in pantry, & Looks interior options. Covered front porch & back deck, to welcome guests and unwind in the fresh air. Impressive great room with vaulted ceiling. Luxurious primary suite with triple windows and tray ceiling. Relaxing primary bath with dual sinks, walk-in closet, & optional freestanding tub.

    K. Hovnanian Homes Builder
    1415 Pennfield Dr Unit 36502364, Middletown, DE 19709
  • 1020 Robinson Rd, Townsend, DE 19734
    1020 Robinson Rd, Townsend, DE 19734
    1020 Robinson Rd, Townsend, DE 19734
    /31

    $514,400 Open Sun 10AM - 5PM

    • 3 Beds
    • 2 Baths

    1020 Robinson Rd, Townsend, DE 19734

    READY NOW!Welcome to your new home in the sought-after 55+ community of the Preserve at Robinson Farms! This Quick Delivery home is packed with over $68,000 worth of upgrades and enhancements, tailored just for you. As you approach, you'll be greeted by a charming front porch that invites you into the Lakeland II floor plan. The foyer sets an elegant tone with dual tray ceilings, leading you

    Mark Handler Mark L Handler Real Estate

    1020 Robinson Rd, Townsend, DE 19734
  • 78 Old Mill Bottom Rd N Unit 36791896, Annapolis, MD 21409
    78 Old Mill Bottom Rd N Unit 36791896, Annapolis, MD 21409
    78 Old Mill Bottom Rd N Unit 36791896, Annapolis, MD 21409
    /14

    $459,900 New Construction

    • 1 Bed
    • 2 Baths
    • 1,076 Sq Ft

    Element 1 Bed Plan at Element at Mill Creek, Annapolis, MD 21409

    The Christopher Companies Builder
    78 Old Mill Bottom Rd N Unit 36791896, Annapolis, MD 21409
  • 78 Old Mill Bottom Rd N Unit 36791900, Annapolis, MD 21409
    78 Old Mill Bottom Rd N Unit 36791900, Annapolis, MD 21409
    78 Old Mill Bottom Rd N Unit 36791900, Annapolis, MD 21409
    /17

    $472,070 New Construction

    • 2 Beds
    • 2 Baths
    • 1,210 Sq Ft

    Element 2 Bed Plan at Element at Mill Creek, Annapolis, MD 21409

    The Christopher Companies Builder
    78 Old Mill Bottom Rd N Unit 36791900, Annapolis, MD 21409
  • 784 Moorings Cir, Stevensville, MD 21666
    784 Moorings Cir, Stevensville, MD 21666
    784 Moorings Cir, Stevensville, MD 21666
    /57

    $659,900

    • 2 Beds
    • 3 Baths
    • 2,074 Sq Ft

    784 Moorings Cir, Stevensville, MD 21666

    This beautifully maintained 2-bedroom, 3-bath home is located in a desirable 55 community and offers comfort, style, and convenience. Enter through a charming courtyard into a bright, open floor plan featuring cathedral ceilings and a spacious great room with a gas fireplace, perfect for relaxing or entertaining. The kitchen features granite countertops, ample cabinetry, and flows seamlessly into

    Deb Trombley Core Partners Realty LLC

    784 Moorings Cir, Stevensville, MD 21666
  • 230 Anglesey Dr, Middletown, DE 19709
    230 Anglesey Dr, Middletown, DE 19709
    230 Anglesey Dr, Middletown, DE 19709
    /45

    $560,000 Open Sat 12PM - 2PM

    • 2 Beds
    • 3 Baths
    • 2,475 Sq Ft

    230 Anglesey Dr, Middletown, DE 19709

    Welcome to 230 Anglesey Drive, a stunning home where luxury and thoughtful design meet everyday comfort. Step inside and be greeted by soaring 9-foot ceilings and rich 6-inch hardwood planks that flow throughout the main living areas, setting the tone for the elegance that awaits within. The open-concept floor plan creates a seamless transition between living, dining, and entertaining spaces,

    Deneen Sweeney Keller Williams Real Estate - West Chester

    230 Anglesey Dr, Middletown, DE 19709
  • 90 Resort Blvd, Dover, DE 19904
    90 Resort Blvd, Dover, DE 19904
    90 Resort Blvd, Dover, DE 19904
    /14

    $745,995

    • 3 Beds
    • 3 Baths
    • 3,395 Sq Ft

    90 Resort Blvd, Dover, DE 19904

    BUILDER CLOSEOUT. This upgraded designer Greenwold Model home is for sale. Features include: 4-Season room ,Faux Beams matching flooring, 2' extension in owner suite, doorway from laundry room to owner-s walk-in closet, Loft space with bonus room, bedroom and bathroom. Beverage Center w/additional cabinetry PLUS Wine Refrigerator. Tray Ceiling in den, an OUTDOOR KITCHEN AND OUTDOOR FIREPLACE!

    Carol Daniels Samson Properties of DE, LLC

    90 Resort Blvd, Dover, DE 19904
  • 206 Northern Oak St Unit 39839252, Middletown, DE 19709
    206 Northern Oak St Unit 39839252, Middletown, DE 19709
    206 Northern Oak St Unit 39839252, Middletown, DE 19709
    /17

    $550,400 New Construction

    • 3 Beds
    • 2 Baths
    • 2,032 Sq Ft

    St. Michael's Plan at K. Hovnanian’s® Four Seasons at Baymont Farms, Middletown, DE 19709

    Impressive single-story foyer graciously welcoming you home. Spacious kitchen with center island and dining area. Convenient Stuff of Life Room with separate laundry area. Large great room opening to kitchen and dining area. Luxury owner's suite with oversized closet & bath. Gourmet kitchen option perfect for your inner chef. Optional loft for guests.

    K. Hovnanian Homes Builder
    206 Northern Oak St Unit 39839252, Middletown, DE 19709
  • 206 Northern Oak St Unit 39821536, Middletown, DE 19709
    206 Northern Oak St Unit 39821536, Middletown, DE 19709
    206 Northern Oak St Unit 39821536, Middletown, DE 19709
    /22

    $580,400 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,378 Sq Ft

    Rockford Plan at K. Hovnanian’s® Four Seasons at Baymont Farms, Middletown, DE 19709

    Gorgeous kitchen with oversized island and spacious pantry. Oversized great room ideal for entertaining. Spacious owner’s suite with luxurious bath. Private home office, perfect for telecommuting. Secluded secondary bedrooms away from owner’s suite. Opt. outdoor living space with deck or screen porch.

    K. Hovnanian Homes Builder
    206 Northern Oak St Unit 39821536, Middletown, DE 19709
  • 115 Hengst Farm Ln, Smyrna, DE 19977
    115 Hengst Farm Ln, Smyrna, DE 19977
    115 Hengst Farm Ln, Smyrna, DE 19977
    /14

    $467,489 New Construction

    • 2 Beds
    • 2 Baths
    • 1,760 Sq Ft

    115 Hengst Farm Ln, Smyrna, DE 19977

    Move-in ready and thoughtfully upgraded, this Aston model offers the perfect blend of style, comfort, and flexibility. Featuring 1,760 square feet of single-level living, this home includes 2 spacious bedrooms and 2 full baths, along with a full basement for extra storage or future living space.Enjoy the extended owners suite for added luxury, along with premium kitchen cabinetry, upgraded

    Benchmark Builders Builder
    115 Hengst Farm Ln, Smyrna, DE 19977
  • 14 White Oak Dr, Perryville, MD 21903
    14 White Oak Dr, Perryville, MD 21903
    14 White Oak Dr, Perryville, MD 21903
    /18

    $239,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    14 White Oak Dr, Perryville, MD 21903

    Build your Dream Home in this Beautiful 55+ Community of Chestnut Point Estates & Marina in Perryville, Md. Four Beautiful Models to choose from (3B-2B) that include: Open Floor Plan, Living Room Custom Entertainment Wall, Fireplace, Granite Countertops in Kitchen, Cultured Marble in Guest & Master Spa Bath, Walk-in Pantry and Bedroom Closets. Stainless Steel Appliances included: Side by Side

    Suzy Schurman Patterson-Schwartz-Newark

    14 White Oak Dr, Perryville, MD 21903
  • 1071 Robinson Rd Unit DELRAY PLAN, Townsend, DE 19734
    1071 Robinson Rd Unit DELRAY PLAN, Townsend, DE 19734
    1071 Robinson Rd Unit DELRAY PLAN, Townsend, DE 19734
    /27

    $439,900 New Construction

    • 3 Beds
    • 2 Baths
    • 2,004 Sq Ft

    1071 Robinson Rd Unit DELRAY PLAN, Townsend, DE 19734

    Visit our 55+ community of The Preserve at Robinson Farm, The Villas. This Delray is to be built just for you! The floor plan has style and simplicity in one, with 3 bedrooms and 2 full baths. This home features a Cottage or Traditional exterior with a covered entry. Once you enter, you will be welcomed by a cozy foyer with luxury vinyl plank flooring. Add a 10' tray ceiling for loft. The open

    Mark Handler Mark L Handler Real Estate

    1071 Robinson Rd Unit DELRAY PLAN, Townsend, DE 19734
  • 1067 Robinson Rd Unit LAKELAND PLAN, Townsend, DE 19734
    1067 Robinson Rd Unit LAKELAND PLAN, Townsend, DE 19734
    1067 Robinson Rd Unit LAKELAND PLAN, Townsend, DE 19734
    /32

    $467,900 New Construction

    • 3 Beds
    • 2 Baths
    • 2,534 Sq Ft

    1067 Robinson Rd Unit LAKELAND PLAN, Townsend, DE 19734

    Visit our 55+ community of The Preserve at Robinson Farm, The Villas. The Lakeland II is a ranch style home with pizzazz and unlike old style ranch homes of the past, this floor plan is exciting and glamorous. The foyer welcomes you in, passing two large bedrooms leading to an amazing kitchen boasting granite with abundant cabinets and a 6' kitchen island workspace that includes an overhang for

    Mark Handler Mark L Handler Real Estate

    1067 Robinson Rd Unit LAKELAND PLAN, Townsend, DE 19734
  • 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

    $858,990 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.

    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

    $669,990 New Construction

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

    Jenkins II Plan at K. Hovnanian’s® Four Seasons at Kent Island - 35' 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.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36466218, 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
    /27

    $819,990 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.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36469043, Chester, MD 21619
  • 206 Northern Oak St Unit 36495347, Middletown, DE 19709
    206 Northern Oak St Unit 36495347, Middletown, DE 19709
    206 Northern Oak St Unit 36495347, Middletown, DE 19709
    /22

    $504,400 New Construction

    • 2 Beds
    • 2 Baths
    • 1,780 Sq Ft

    Eastwood Plan at K. Hovnanian’s® Four Seasons at Baymont Farms, Middletown, DE 19709

    Elegant foyer entry welcoming friends and family. Generous ceiling height for maximum natural light and openness. Open, single-story home design boasting dream kitchen with island. Spacious great room with optional fireplace creating relaxing atmosphere. Secluded owner's suite with oversized closet and private bath.

    K. Hovnanian Homes Builder
    206 Northern Oak St Unit 36495347, Middletown, DE 19709
  • 206 Northern Oak St Unit 36451018, Middletown, DE 19709
    206 Northern Oak St Unit 36451018, Middletown, DE 19709
    206 Northern Oak St Unit 36451018, Middletown, DE 19709
    /19

    $553,400 New Construction

    • 2 Beds
    • 2 Baths
    • 2,080 Sq Ft

    Killarney I Plan at K. Hovnanian’s® Four Seasons at Baymont Farms, Middletown, DE 19709

    Cozy porch welcoming guests to your home. Inviting dining room, ideal for hosting dinner parties. Kitchen with large island and corner pantry. Great room with optional HovHub and wet bar. Owner's suite with private bath and oversized walk-in closet. Three-car tandem garage with additional storage. Opt. loft for additional living with bed and full bath.

    K. Hovnanian Homes Builder
    206 Northern Oak St Unit 36451018, Middletown, DE 19709
  • 1415 Pennfield Dr Unit 36480087, Middletown, DE 19709
    1415 Pennfield Dr Unit 36480087, Middletown, DE 19709
    1415 Pennfield Dr Unit 36480087, Middletown, DE 19709
    /26

    $535,990 New Construction

    • 3 Beds
    • 2 Baths
    • 2,148 Sq Ft

    Aberdeen II Plan at K. Hovnanian’s® Four Seasons at Pennfield, Middletown, DE 19709

    Spacious kitchen with island and ample counterspace. Sunlit great room adjacent to kitchen and dining area. Relaxing primary suite with sitting room and luxurious bath. HovHub makes for a great home office or study space. Expansive covered patio, perfect for dining al fresco. HovHall with closet and access to 2-car garage.

    K. Hovnanian Homes Builder
    1415 Pennfield Dr Unit 36480087, Middletown, DE 19709
  • 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

    $848,990 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.

    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

    $499,990 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.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36493007, Chester, MD 21619
  • 206 Northern Oak St Unit 36472277, Middletown, DE 19709
    206 Northern Oak St Unit 36472277, Middletown, DE 19709
    206 Northern Oak St Unit 36472277, Middletown, DE 19709
    /19

    $579,400 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,462 Sq Ft

    Mont Blanc Plan at K. Hovnanian’s® Four Seasons at Baymont Farms, Middletown, DE 19709

    Spacious, inviting front entry porch. Kitchen with expansive island and dual pantries. Open great room and dining area ideal for entertaining. Convenient secondary bedrooms for guests. Owner's suite with private bath and walk-in closet. Direct access to laundry room keeping your home tidy. Three-car tandem garage with additional storage.

    K. Hovnanian Homes Builder
    206 Northern Oak St Unit 36472277, Middletown, DE 19709
  • 206 Northern Oak St Unit 36472485, Middletown, DE 19709
    206 Northern Oak St Unit 36472485, Middletown, DE 19709
    206 Northern Oak St Unit 36472485, Middletown, DE 19709
    /13

    $588,400 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,457 Sq Ft

    Lewes Plan at K. Hovnanian’s® Four Seasons at Baymont Farms, Middletown, DE 19709

    Open and airy kitchen with pantry and oversized island. Cozy dining area adjacent to kitchen for enjoying casual meals. Luxurious owner's suite with dual walk-in closets and large bath. Hall walk-in closet for additional storage. Direct access to laundry room from garage. Covered porch to enjoy evenings outdoors.

    K. Hovnanian Homes Builder
    206 Northern Oak St Unit 36472485, Middletown, DE 19709
  • 614 Virdin Dr, Smyrna, DE 19977
    614 Virdin Dr, Smyrna, DE 19977
    614 Virdin Dr, Smyrna, DE 19977
    /31

    $449,000 Open Sat 12PM - 2PM

    • 2 Beds
    • 2 Baths
    • 1,797 Sq Ft

    614 Virdin Dr, Smyrna, DE 19977

    Welcome to 614 Virdin Dr in Auburn Meadows, Smyrna’s premier 55+ community where quiet convenience meets a truly low-maintenance lifestyle. Built in 2025 and just under a year old, this nearly 1,800 sq ft Tuscany model offers the benefit of new construction without the wait complete with thoughtful upgrades already in place. Step inside to a bright, open-concept layout featuring wide plank LVP

    Michelle Rawley Bryan Realty Group

    614 Virdin Dr, Smyrna, DE 19977
  • 199 Indigo Cir Unit 199, Smyrna, DE 19977
    199 Indigo Cir Unit 199, Smyrna, DE 19977
    199 Indigo Cir Unit 199, Smyrna, DE 19977
    /30

    $175,500

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft

    199 Indigo Cir Unit 199, Smyrna, DE 19977

    Come see this beautiful, manufactured home in the desirable 55+ section of Ridgewood Manor—showcasing true showroom condition with exceptional attention to detail throughout! Offering 3 bedrooms, 2 full baths, and 1,404 sq ft of luxury living, this home is perfectly situated on a premium privacy lot backing to a tree-lined setting. This exceptional property delivers the perfect blend of privacy,

    Faith Streett BHHS Fox & Roach-Concord

    199 Indigo Cir Unit 199, Smyrna, DE 19977
  • 854 Moorings Cir Unit 12, Stevensville, MD 21666
    854 Moorings Cir Unit 12, Stevensville, MD 21666
    854 Moorings Cir Unit 12, Stevensville, MD 21666
    /16

    $505,000 Open Sat 1PM - 3PM

    • 2 Beds
    • 2 Baths
    • 1,464 Sq Ft

    854 Moorings Cir Unit 12, Stevensville, MD 21666

    OPEN SAT/SUN 4/11 & 4/12, 1:00–3:00. SHOWINGS AVAILABLE STARTING 4/10. BEST VALUE IN BAY BRIDGE COVE! Welcome to Bay Bridge Cove, a premier 55+ community on beautiful Kent Island! This adorable Easton offers cottage charm with a paved entry courtyard, hardwood floors, professional painting, and main-level living. The open-flow floor plan features an island kitchen with custom pendant and

    Deborah Laggini Long & Foster Real Estate, Inc.

    854 Moorings Cir Unit 12, Stevensville, MD 21666
  • 1000 Herons Nest Way Unit 42, Chester, MD 21619
    1000 Herons Nest Way Unit 42, Chester, MD 21619
    1000 Herons Nest Way Unit 42, Chester, MD 21619
    /54

    $599,000

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

    1000 Herons Nest Way Unit 42, Chester, MD 21619

    Rarely on the market Penthouse level Chester model available immediately! Balcony views from the top floor leftside provide view of the Chester River, Macum Creek and the Community Kayak's. Located within the serene and vibrant community of Four Seasons at Kent Island, this exquisite 2-bedroom, 2.5 bath Built in 2020, this elegant unit combines modern design with high-end finishes, creating a

    Dan Judge RE/MAX United Real Estate

    1000 Herons Nest Way Unit 42, Chester, MD 21619
  • 38 Leander Dr, Dover, DE 19904
    38 Leander Dr, Dover, DE 19904
    38 Leander Dr, Dover, DE 19904
    /29

    $493,000 Open Sat 12PM - 2PM

    • 2 Beds
    • 2 Baths
    • 2,242 Sq Ft

    38 Leander Dr, Dover, DE 19904

    Welcome to 38 Leander Drive, a beautifully upgraded, nearly-new home offering over 2,200 square feet of thoughtfully designed first-floor living in the highly desirable 55+ community of Nobles Pond. With a spacious layout that lives larger than expected, this home combines the ease of single-level living with the space and functionality often missing in similar homes. Built just three years ago

    Carol Wick Bryan Realty Group

    38 Leander Dr, Dover, DE 19904
  • 330 Colony Point Place, Edgewater, MD 21037
    330 Colony Point Place, Edgewater, MD 21037
    330 Colony Point Place, Edgewater, MD 21037
    /27

    $575,000

    • 2 Beds
    • 2 Baths
    • 1,778 Sq Ft

    330 Colony Point Place, Edgewater, MD 21037

    Welcome to the Villas at South River Colony- the sought-after active 55+ community with carefree living! This spacious one level townhome with 2 bedrooms and 2 baths has soaring ceilings for an open and airy feel. Since October 2024, there have been many significant upgrades and improvements which include: new LVP flooring throughout, new paint and upgraded baseboards throughout, new quartz

    Pamela Debnam Houwzer, LLC

    330 Colony Point Place, Edgewater, MD 21037
  • 917 Moorings Cir Unit 131, Stevensville, MD 21666
    917 Moorings Cir Unit 131, Stevensville, MD 21666
    917 Moorings Cir Unit 131, Stevensville, MD 21666
    /82

    $715,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 3 Baths
    • 2,284 Sq Ft

    917 Moorings Cir Unit 131, Stevensville, MD 21666

    Welcome to this exceptional model home, fully loaded with upgrades and offering over 2,200 square feet of luxurious living space. The main level showcases beautiful luxury plank flooring and an open-concept design that seamlessly connects the dining room, kitchen, and great room—ideal for both everyday living and entertaining. Stylish shiplap wall accents and a whole-house sound system add to the

    Deborah Savoie Long & Foster Real Estate, Inc.

    917 Moorings Cir Unit 131, Stevensville, MD 21666
Maryland Kent County Chestertown

Homes for Sale in a Senior Community in Chestertown, MD

Home Trends in Chestertown, MD

On average, homes in Chestertown, MD sell after 50 days on the market compared to the national average of 55 days. The median sale price for homes in Chestertown, MD over the last 12 months is $375,000, up 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$375,000
Median Single Family Sale Price
$389,000
Median Townhouse Sale Price
$280,000
Median 2 Bedroom Sale Price
$375,000
Median 1 Bedroom Sale Price
$242,500
Average Price Per Sq Ft
$215
Number of Homes for Sale
38
Last 12 months Home Sales
95
Months of Supply
4.80
Median List Price
$375,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
1%
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