5,162

Queen Annes, MD Homes

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  • /55

    $989,000

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

    330 Macum Creek Dr, Chester, MD 21619

    Great price on this home with tons of upgrades! Sellers have found Home of Choice. 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

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (667) 256-7961

    330 Macum Creek Dr, Chester, MD 21619
  • /2

    $4,300 per month

    • 2 Beds
    • 2 Baths
    • 2,147 Sq Ft
    • House for Rent

    137 Warbler Way, CHESTER, MD 21619

    Welcome to this charming single-family home in the heart of coveted Four Seasons. Built in 2024, this delightful '55 or better' residence offers two bedrooms and two bathrooms within 2,147 square feet of living space, perfect for anyone seeking comfort and convenience.Key property features include a modern, open design with soaring ceilings ranging 10-13'- throughout the home! Enjoy the

    137 Warbler Way, CHESTER, MD 21619
  • /47

    $435,000 Sold Aug 04, 2025

    • 1,568 Sq Ft
    • $277/SF
    • 34 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1995

    2707 Cox Neck Rd, Chester, MD 21619

    Welcome to Harborview, a long established community on Maryland's eastern shore, home of some of the best seafood on the eastern seaboard! Come see everything that living on "The Shore" has to offer. Fantastic dining on the Kent Narrows, shopping at the outlets, the new pickleball courts in nearby Stevensville and Grasonville, the dog park and of course the new skate park! The Cross Island trail

    Samantha Hernandez Douglas Realty, LLC

    2707 Cox Neck Rd, Chester, MD 21619
    • /81

      Est $769,689 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,771 Sq Ft

      136 Evelyne St, Chester, MD 21619

      136 Evelyne St, 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) 634-7627

    4000 Herons Nest Way Unit 22, Chester, MD 21619
  • /43

    $495,000 Sold Jul 31, 2025

    • 1,400 Sq Ft
    • $354/SF
    • 2 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2023

    2614 Ellicott Dr, Chester, MD 21619

    Like-New Construction | Turn-Key Living | Prime Chester Location. Welcome to 2614 Ellicott Drive, a stunning 2023-built home that blends modern design with everyday comfort — all nestled in the heart of Kent Island. Move-in ready and in absolute mint condition, this beautifully appointed property offers the perfect blend of style, space, and location. Step inside to discover rich, wide-plank

    Wendy Oliver Coldwell Banker Realty

    2614 Ellicott Dr, Chester, MD 21619
    • /44

      Est $857,958 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,225 Sq Ft

      326 Thomas White Blvd, Chester, MD 21619

      326 Thomas White Blvd, Chester, MD 21619
  • /106

    $650,000

    • 6 Beds
    • 3 Baths
    • 3,760 Sq Ft

    204 Skipper Ln, Chester, MD 21619

    Welcome home to spacious comfort and thoughtful design in this inviting six-bedroom, three-bath residence nestled on a quiet lane in Chester. With over 3,700 square feet of interior living space, there’s room here for everyone—and maybe even that home office or gym you’ve been dreaming about.Step inside to find an updated kitchen ready for your culinary adventures, featuring modern

    Agent Photo

    Andy Schweigman

    Douglas Realty, LLC

    (410) 324-6571

    204 Skipper Ln, Chester, MD 21619
  • /51

    $485,000 Sold Jul 31, 2025

    • 1,840 Sq Ft
    • $264/SF
    • 15 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2001

    412 Hanna Ct, Chester, MD 21619

    Welcome to 412 Hanna Court, Chester, MD – DID YOU KNOW THIS HOME HAS AN 2.75% ASSUMABLE VA MORTGAGE of $294K!!! Nestled at the end of a quiet cul-de-sac in the highly sought-after Claybourne Woods community, this beautifully maintained 4-bedroom, 2.5-bath home blends modern upgrades with everyday comfort in an ideal Eastern Shore location. Enjoy a quick 30-minute commute to Downtown

    Sarah Miller Hubble Bisbee Christie's International Real Estate

    412 Hanna Ct, Chester, MD 21619
    • /59

      Est $844,460 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,840 Sq Ft

      237 Evelyne St, Chester, MD 21619

      237 Evelyne St, 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
  • /27

    $340,000 Sold Jul 31, 2025

    • 1,104 Sq Ft
    • $308/SF
    • 34 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1983

    15G Queen Anne Way, Chester, MD 21619

    Welcome to Queens Landing - Easy Living in this 2 bed 1.5 bath Waterfront Townhome ! Home features private balcony and patio overlooking the Chester River. Open floor plan with dining/living combo and main level powder room. So many amenities including Club House, In-ground heated pool, fitness center, and tennis and pickleball courts. Enjoy marina views and biking and walking trails. You'll

    Mackenzie Hoffer CENTURY 21 New Millennium

    15G Queen Anne Way, Chester, MD 21619
    • /69

      Est $749,641 Not Listed For Sale

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

      334 Thomas White Blvd, Chester, MD 21619

      334 Thomas White Blvd, Chester, MD 21619
  • /43

    $450,000

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

    54A Queen Caroline Ct, Chester, MD 21619

    OPEN HOUSE, Saturday, August 2, from 11 am to 12 pm...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

    Darlene Winegardner RE/MAX Executive

    54A Queen Caroline Ct, Chester, MD 21619
  • /55

    $829,900 Sold Jul 30, 2025

    • 1,900 Sq Ft
    • $437/SF
    • 17 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 2025

    218 Switchgrass Way Unit 1732, Chester, MD 21619

    Experience the perfect blend of form and function in the Chester, a thoughtfully designed 2-bedroom, 2.5-bath home with a 1-car garage and smart upgrades throughout. Whether you're looking for a comfortable everyday retreat or a low-maintenance second home, this property offers it all.Enjoy the warmth of an electric fireplace, the convenience of a built-in dry bar, and the flexibility of

    Mary Anne Kowalewski KOVO Realty

    218 Switchgrass Way Unit 1732, Chester, MD 21619
    • /46

      Est $591,746 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,824 Sq Ft

      163 Claiborne St, Chester, MD 21619

      163 Claiborne St, 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
  • /24

    $320,000 Sold Jul 30, 2025

    • 800 Sq Ft
    • $400/SF
    • 79 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1983

    34B Queen Anne Way Unit B, Chester, MD 21619

    EXCELLENT PRICE reduction!! Waterfront...waterfront! Super one bedroom/bathroom condo. Largest of the one-bedroom units. Absolutely gorgeous view across the Chester River from the living area . Private patio on waterside. Luxury vinyl wood-look flooring throughout! The condo is quite roomy and easy to take care of! No outstanding assessments on it! Low condo fee, as well! Community has wonderful

    Mary Stevens Long & Foster Real Estate, Inc.

    34B Queen Anne Way Unit B, Chester, MD 21619
    • /38

      Est $670,286 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,320 Sq Ft

      121 Henry Stoupe Way, Chester, MD 21619

      121 Henry Stoupe Way, Chester, MD 21619
  • /27

    $844,900 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
  • /10

    $541,900 Sold Jul 28, 2025

    • 2,003 Sq Ft
    • $271/SF
    • 2 Beds
    • 2.5 Baths
    • Built 2025

    121 Wheelhouse Way Unit 12, Chester, MD 21619

    Efficient gourmet kitchen featuring vast center island & designer cabinets.Cozy electric fireplace adds character & warmth to great room.Refined dining area featuring convenient dry bar.Lavish owner's suite & spa bath with walk-in closet.Productive home office with double doors.Inviting covered patio for relaxing outdoors.

    K. Hovnanian Homes

    121 Wheelhouse Way Unit 12, Chester, MD 21619
    • /20

      Est $535,500 Not Listed For Sale

      2629 Cecil Dr, Chester, MD 21619

      2629 Cecil Dr, Chester, MD 21619
  • /25

    $659,900 New Construction

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

    Jenkins II Plan at K. Hovnanian’s® Four Seasons at Kent Island - Single Family, 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
  • /63

    $775,000 Sold Jul 28, 2025

    • 2,331 Sq Ft
    • $332/SF
    • 1 Day On Market
    • 3 Beds
    • 2 Baths
    • Built 2021

    320 Bayberry Dr, Chester, MD 21619

    Have it all at 320 Bayberry Drive in the award-winning Four Seasons at Kent Island! This stunning 2021-built home sits on a premium lot adjacent to open space, offering exceptional privacy and abundant natural light. Beautifully upgraded throughout, the home features 10-foot ceilings, a gourmet kitchen with upgraded cabinetry and tile, designer lighting, luxury flooring, and a cozy gas fireplace.

    Melanie Wood Berkshire Hathaway HomeServices PenFed Realty

    320 Bayberry Dr, Chester, MD 21619
    • /34

      Est $434,456 Not Listed For Sale

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

      7 Queen Victoria Way, Chester, MD 21619

      7 Queen Victoria Way, Chester, MD 21619
  • /27

    $807,900 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
  • /43

    $595,000 Sold Jul 28, 2025

    • 2,656 Sq Ft
    • $224/SF
    • 59 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 2003

    1614 Postal Rd, Chester, MD 21619

    Welcome to this Lovingly and Well-Maintained Colonial Style Home! Looking for a Home based business? This one is it, as it offers a rare opportunity with incredible versatility with Town Center Zoning, making it perfect for a private residence, bed & breakfast, Airbnb, or the opportunity to live where you work. Nestled on a Large Lot backing to Woods offers both Privacy and Charm! Spanning

    Pamela Ackermann-Doll RE/MAX Executive

    1614 Postal Rd, Chester, MD 21619
    • /12

      Est $538,448 Not Listed For Sale

      2510 Roberta Dr, Chester, MD 21619

      2510 Roberta Dr, Chester, MD 21619
  • /41

    $836,900 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
  • /19

    $739,900 Sold Jul 24, 2025

    • 2,602 Sq Ft
    • $284/SF
    • 3 Beds
    • 2.5 Baths
    • Built 2025

    211 Switchgrass Way Unit 31, Chester, MD 21619

    Striking gourmet kitchen with designer cabinets & chef-worthy island.Elegant dining area featuring fancy dry bar.Refined great room featuring stunning fireplace.Serene owner's suite with maginificnet sitting room & walk-in closets.Owner's spa bath with dual sinks and lavish shower.Wonderful balcony for relaxing outdoors.

    K. Hovnanian Homes

    211 Switchgrass Way Unit 31, Chester, MD 21619
    • /48

      Est $332,272 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,370 Sq Ft

      55 Queen Caroline Ct, Chester, MD 21619

      55 Queen Caroline Ct, 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

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36493007, Chester, MD 21619
  • /11

    $259,000 Sold Jul 24, 2025

    • 960 Sq Ft
    • $270/SF
    • 160 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1984

    107 Lee Rd, Chester, MD 21619

    OPEN HOUSE, Saturday, May 24, from 11am to 1pm...Best 3 Br buy on Kent Island! Recent upgrades! Hurry!

    Darlene Winegardner RE/MAX Executive

    107 Lee Rd, Chester, MD 21619
    • /66

      Est $916,808 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 3,475 Sq Ft

      221 John Gibson Dr, Chester, MD 21619

      221 John Gibson Dr, Chester, MD 21619
  • /10

    $740,900 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
  • /24

    $684,900 Sold Jul 23, 2025

    • 1,900 Sq Ft
    • $360/SF
    • 2 Beds
    • 2.5 Baths
    • Built 2025

    201 Switchgrass Way Unit 33, Chester, MD 21619

    Gourmet kitchen with wall oven & spacious central island.Dry bar in the dining area adds a stylish touch.Great room features an electric fireplace for cozy evenings.Sliding doors open to a private balcony off the great room.Owner’s suite with direct balcony access for fresh air.Dual vanities in the spa-inspired owner’s bath.Thoughtfully designed layout with

    K. Hovnanian Homes

    201 Switchgrass Way Unit 33, Chester, MD 21619
    • /59

      Est $850,718 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,076 Sq Ft

      134 Henry Stoupe Way, Chester, MD 21619

      134 Henry Stoupe Way, Chester, MD 21619
  • /12

    $872,900 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
  • /26

    $999,900 Sold Jul 23, 2025

    • 1,900 Sq Ft
    • $526/SF
    • 2 Beds
    • 2.5 Baths
    • Built 2025

    218 Switchgrass Way Unit 32, Chester, MD 21619

    Private home office offers a quiet & functional workspace.Gourmet kitchen features a center island & built-in wall oven.Dining area with a dry bar adds convenience for hosting.Great room includes an electric fireplace & balcony access.Sliding glass doors connect indoor & outdoor living spaces.Owner's suite with private balcony creates a serene

    K. Hovnanian Homes

    218 Switchgrass Way Unit 32, Chester, MD 21619
    • /60

      Est $548,304 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 2,048 Sq Ft

      107 Gibson Cir, Chester, MD 21619

      107 Gibson Cir, Chester, MD 21619

Showing Results 1 - 40, Page 1 of 18

Home Trends in Chester, MD

Housing Trends

Median Sale Price
$645,000
Median Single Family Sale Price
$654,650
Median Townhouse Sale Price
$469,000
Median 2 Bedroom Sale Price
$539,950
Average Price Per Sq Ft
$350
Number of Homes for Sale
12
Last 12 months Home Sales
111
Months of Supply
1.30
Median List Price
$637,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-12%
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