5,141

Queen Annes, MD Homes

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  • /55

    $1,050,000

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

    330 Macum Creek Dr, Chester, MD 21619

    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 screened porch has been converted into a bright and inviting four-season sunroom,

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (667) 256-7961

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

    $1,650 per month

    • 2 Beds
    • 1 Bath
    • 850 Sq Ft
    • Condo for Rent

    1540 Postal Rd Unit 108, Chester, MD 21619

    Property Id: 1348539SENIOR APTS 62+ Two-bedroom, one bath on first flooravailable to see July 9th. Appliances included. Small petsallowed. Close to all your needs. Call today .

    1540 Postal Rd Unit 108, 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
    • /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
  • /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
  • /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
  • /27

    $340,000 Pending

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

    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
    • /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
  • /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) 639-3740

    4000 Herons Nest Way Unit 22, 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
    • /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
  • /43

    $450,000 Open Sat 11AM - 12PM

    • 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
  • /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
    • /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
  • /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
  • /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
    • /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
  • /12

    $872,900 New Construction

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

    Mykonos, 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

    K Hovnanian's Four Seasons

    Mykonos, 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
    • /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
  • /26

    $807,900 New Construction

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

    Kerr, 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's Four Seasons

    Kerr, 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
    • /20

      Est $535,500 Not Listed For Sale

      2629 Cecil Dr, Chester, MD 21619

      2629 Cecil Dr, Chester, MD 21619
  • /24

    $659,900 New Construction

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

    Jenkins II, 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's Four Seasons

    Jenkins II, Chester, MD 21619
  • /42

    $719,900 Sold Jul 22, 2025

    • 2,791 Sq Ft
    • $258/SF
    • 11 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2025

    510 Warbler Way, Chester, MD 21619

    Introducing the Simone – Where Modern Comfort Meets Farmhouse CharmProjected for settlement on July 2025, the Simone home design offers the perfect blend of open-concept living and timeless Farmhouse style. With 4 spacious bedrooms, 3 full baths, and a 2-car garage, this home is designed with both functionality and flair.Step inside to find stylish laminate flooring flowing

    Mary Anne Kowalewski KOVO Realty

    510 Warbler Way, 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
  • /10

    $740,900 New Construction

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

    Taylor, 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's Four Seasons

    Taylor, Chester, MD 21619
  • /44

    $295,000 Sold Jul 21, 2025

    • 1,073 Sq Ft
    • $275/SF
    • 22 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1996

    513 Teal Ct, Chester, MD 21619

    *Experience a getaway lifestyle at this stunning 2nd-floor condominium nestled within the prestigious Bayside Condominium Community. Enjoy peaceful views of the pond and fountain from the private balcony. You will delight in the pond views from the living room, dining and kitchen. The spacious living room features built-ins and seamlessly transitions into the dining area, complete with a sliding

    April Heim Rosendale Realty

    513 Teal Ct, Chester, MD 21619
    • /12

      Est $538,448 Not Listed For Sale

      2510 Roberta Dr, Chester, MD 21619

      2510 Roberta Dr, Chester, MD 21619
  • /12

    $474,990 New Construction

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

    Magothy, 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

    K Hovnanian's Four Seasons

    Magothy, Chester, MD 21619
  • /58

    $1,435,900 Sold Jul 17, 2025

    • 2,602 Sq Ft
    • $552/SF
    • 9 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2024

    218 Switchgrass Way Unit 1744, Chester, MD 21619

    Stylish Comfort & Thoughtful Design – SevernReady for June 2025 move-in, the Severn offers a refined take on condo living with 3 bedrooms, 2.5 baths, and a 1-car garage—all wrapped in elegant, low-maintenance style.The open-concept layout features laminate flooring throughout, with tile in both full baths, creating a clean and cohesive flow from room to room. At the heart of the

    Mary Anne Kowalewski KOVO Realty

    218 Switchgrass Way Unit 1744, 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
  • /27

    $844,900 New Construction

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

    Franklin, 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's Four Seasons

    Franklin, Chester, MD 21619
  • /55

    $649,900 Sold Jul 15, 2025

    • 2,003 Sq Ft
    • $324/SF
    • 8 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 2024

    218 Switchgrass Way Unit 1711, Chester, MD 21619

    Magothy | Projected Settlement: June 2025Welcome to the Magothy, a thoughtfully designed home with an anticipated move-in date of June 2025. This elegant residence offers 2 bedrooms, 2.5 bathrooms, and a 1-car garage, perfectly blending comfort and modern convenience.Interior Highlights:Spacious Home Office with lighted French doorsStylish dry bar – ideal for

    Mary Anne Kowalewski KOVO Realty

    218 Switchgrass Way Unit 1711, 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
  • /40

    $836,900 New Construction

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

    Tuscaloosa, 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's Four Seasons

    Tuscaloosa, Chester, MD 21619
  • /42

    $679,000 Sold Jul 15, 2025

    • 2,134 Sq Ft
    • $318/SF
    • 33 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2013

    194 Evelyne St, Chester, MD 21619

    Welcome to 194 Evelyne Street, located in the sought-after waterfront community of Gibson's Grant! Get ready to embrace the laid-back, coastal lifestyle you’ve always dreamed of—right from the comfort of home. If you've been searching for the ease and comfort of one-level living, your search ends here!This beautifully crafted Stanford model by Koch Homes offers just over 2,000 square feet of

    Tara Trout Keller Williams Flagship

    194 Evelyne St, 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
  • /61

    $799,000 Pending

    • 3 Beds
    • 3 Baths
    • 2,453 Sq Ft

    194 Sailcloth Way, Chester, MD 21619

    Welcome to your dream home situated on a coveted premium lot that backs to the woods giving you endless views of wildlife. The first-floor living is ideal for all homeowners and offers you a large primary bedroom, an office/2nd bedroom and a completely open concept on the main level. The kitchen boasts custom cabinets, stainless steel appliances, double oven, gas range with exhaust hood and

    Ross Hunsberger Coldwell Banker Realty

    194 Sailcloth Way, Chester, MD 21619
  • /66

    $1,700,000 Sold Jul 11, 2025

    • 2,824 Sq Ft
    • $602/SF
    • 2 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1992

    2921 Cox Neck Rd E, Chester, MD 21619

    Welcome to waterfront living at its finest in the highly sought-after Southwind community on Kent Island, where this stunning home offers one of the most breathtaking views of Crab Alley Bay. Perfectly positioned with an east-facing orientation, you'll enjoy spectacular sunrises that paint the sky and reflect off the water each morning. This beautifully designed 4-bedroom, 2.5-bath residence

    Lynn Tuozzo Berkshire Hathaway HomeServices PenFed Realty

    2921 Cox Neck Rd E, Chester, MD 21619

Showing Results 1 - 40, Page 1 of 18

Home Trends in Chester, MD

Housing Trends

Median Sale Price
$649,900
Median Single Family Sale Price
$671,400
Median Townhouse Sale Price
$469,000
Median 2 Bedroom Sale Price
$539,950
Average Price Per Sq Ft
$345
Number of Homes for Sale
19
Last 12 months Home Sales
115
Months of Supply
2.00
Median List Price
$647,450
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-12%
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