52

Homes for Sale in 21629

Section Image Section Image
  • /38

    $479,000

    • 4 Beds
    • 2.5 Baths
    • 2,747 Sq Ft

    8605 Hickory Place, Denton, MD 21629

    Beautiful Colonial Farmhouse nestled on a wooded lot at the end of a cul-de-sac private lane. This 4 bedroom, 2.5 bath home has been meticulously maintained and features a traditional floor plan with a large kitchen/breakfast area, large family room with vaulted ceilings and a gas fireplace, separate dining room, living room/office. Second floor includes a primary suite with large bathroom with a

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    8605 Hickory Place, Denton, MD 21629
  • /87

    $1,550,000

    • 5 Beds
    • 4.5 Baths
    • 4,853 Sq Ft

    322 S 2nd St, Denton, MD 21629

    Wake up to sunrise on the Choptank River and wind down with some of the most stunning sunsets on the Eastern Shore — with Ospreys, Eagles, Herons, and an abundance of wildlife as your daily backdrop. This stunning 4,853 sq ft waterfront estate sits on 2.44 acres with 268 feet of private river frontage, putting you right on the water and just steps from the best of historic downtown Denton. Built

    Agent Photo

    Elizabeth Osborn

    Coldwell Banker Realty

    322 S 2nd St, Denton, MD 21629
  • /27

    $369,900

    $5K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 2,268 Sq Ft

    803 Market St, Denton, MD 21629

    This inviting Victorian offers 4 bedrooms and 1.5 baths, that’s perfect for unwinding at the end of the day. Inside, natural light fills the main level, highlighting warm hardwood floors and comfortable living spaces. The living and dining areas connect seamlessly, creating an easy flow for everyday living. The kitchen features ample cabinet and counter space, stainless steel appliances, and a

    Steven Parsons Coldwell Banker Realty

    803 Market St, Denton, MD 21629
  • /46

    $445,000

    • 4 Beds
    • 2 Baths
    • 1,986 Sq Ft

    25699 Auction Rd, Federalsburg, MD 21632

    Opportunity to purchase this remodeled residence situated on over 18 acres. Improements include new luxury vinyl plank flooring and Advantech subfloors to a fully replaced middle beam for lasting structural integrity. Nearly all windows and doors are brand new, the heating system has been upgraded to an efficient heat pump, and the electrical system now features a 200-amp panel, a dedicated

    Barbara McCaffrey Redfin Corp

    25699 Auction Rd, Federalsburg, MD 21632
  • /48

    $374,900

    Open Sat 2PM - 4PM
    • 4 Beds
    • 2.5 Baths
    • 2,176 Sq Ft

    8548 Dogwood Blossom Ln, Denton, MD 21629

    Nestled along a private road in a peaceful, tucked-away setting, this well-maintained Colonial offers the perfect blend of privacy, space, and convenience. Situated on more than 1.2 acres, the property backs to mature woods, providing beautiful wooded views and a serene backdrop to everyday living. The home needs only minor cosmetic updates, making it an excellent opportunity to add your own

    Barbara McCaffrey Redfin Corp

    8548 Dogwood Blossom Ln, Denton, MD 21629
  • /50

    $419,000

    • 5 Beds
    • 2.5 Baths
    • 2,382 Sq Ft

    225 S 2nd St, Denton, MD 21629

    Welcome to one of Denton's most charming historic homes, where timeless Victorian architecture, thoughtful updates, and small-town living come together beautifully. Situated on a picturesque corner lot in Denton's historic district, this lovingly maintained five-bedroom home offers more than 2,300 square feet of character-filled living space, abundant natural light, original architectural

    Barbara McCaffrey Redfin Corp

    225 S 2nd St, Denton, MD 21629
  • /43

    $424,900

    • 3 Beds
    • 1.5 Baths
    • 1,800 Sq Ft

    509 S 2nd St, Denton, MD 21629

    Welcome to one of Denton’s most enchanting hidden retreats — a beautifully restored and thoughtfully updated 1941 Cape Cod tucked among towering trees, lush gardens, and comfortable living spaces in the heart of town.Lovingly renovated while preserving its original charm and architectural character, the main residence offers timeless warmth and understated elegance throughout. Rich hardwood

    Judith Germain Benson & Mangold, LLC

    509 S 2nd St, Denton, MD 21629
  • /30

    $52,000

    • Land
    • 5.2 Acres
    • $10,000 per Acre

    American Corner Rd, Denton, MD 21629

    5.20 Acres Wooded Land on Paved American Corner Road in Caroline County, MarylandCash Price: $52,000Reservation Fee: $900 non-refundable reservation fee secures this property. Reservation fee will be counted toward purchase price or down payment.With your Purchase You Get:1. A Deed in Your Own Name2. 4. NO Closing Fees if you Close Directly In-House with our BBB A+

    Elegment Land Elegment.com

    American Corner Rd, Denton, MD 21629
  • /15

    $118,000

    • 3 Beds
    • 1.5 Baths
    • 1,664 Sq Ft

    501 Lincoln St, Denton, MD 21629

    Property is being sold As/ Is. Located on a corner lot. Owner has completed some work to the property, but additional work will be required. Please contact Denton Planning and Codes to verify remaining requirements to obtain an occupancy permit.

    Diane Wenk Wright Real Estate

    501 Lincoln St, Denton, MD 21629
  • /28

    $405,000

    • 3 Beds
    • 2 Baths
    • 1,740 Sq Ft

    25214 Smith Landing Rd, Denton, MD 21629

    Waterfront parcel on the Choptank River! 3 (possibly 4) bedroom, 2 full bath 2-story home on a 3.15 +/- acre fee simple parcel. Numerous shade trees and perennial plantings surround the home. Two (2) outbuildings await your vision. Located approximately 15 miles from the Harrington Raceway & Casino, 30 miles from the Bay Bridge and 50 miles from local beach resorts. Owner say to bring

    John Fifer Brokers Realty Group, LLC

    25214 Smith Landing Rd, Denton, MD 21629
  • /83

    $779,000

    Coming Soon
    • 5 Beds
    • 5 Baths
    • 3,816 Sq Ft

    8821 Dorothy Ln, Denton, MD 21629

    " Diamond in the Rough" This property is being sold to settle an estate and no repairs will be made. Offering considerable upside potential, this private 5 bedroom, 5 bath home is tucked away on the Choptank River in the community of Asbury.

    Andrew Beaven Wright Real Estate

    8821 Dorothy Ln, Denton, MD 21629
  • /32

    $625,000

    • 3 Beds
    • 2 Baths
    • 1,834 Sq Ft

    28402 Liden School Rd, Denton, MD 21629

    This is the one! Approx. 16.77 acres with an owner built 3 bedroom home. One acre with home plus additional acreage. Some acreage is wooded with wild life including, but not limited to, rabbit, deer, and turkey. This home has magnificent kitchen with custom cabinetry and SS appliances, including a 5 burner stove and double wall oven. Pellet stove is included for those cool evenings and damp days.

    Michael Shipley Benson & Mangold, LLC.

    28402 Liden School Rd, Denton, MD 21629
  • /4

    $200,000

    • 3 Beds
    • 1 Bath
    • 2,020 Sq Ft

    22971 Tuckahoe Springs Dr, Denton, MD 21629

    Ranch style home situated on a 1.18 acre lot. There is no access to the interior of the home. Priced below assessed value, home to be transferred occupied, as-is. Please do not disturb the occupants.

    Michael Johnson Marathon Real Estate

    22971 Tuckahoe Springs Dr, Denton, MD 21629
  • /2

    $25,000

    • Land
    • 22,651 Sq Ft
    • $48,077 per Acre

    10291 Bridge St, Denton, MD 21629

    1/2 ACRE LOT IN DENTON. THIS PROPERTY WAS PURCHASED THROUGH TAX SALE, SELLER IS BRYNN, LLC.

    Henry Gibbons-Neff Meredith Fine Properties

    10291 Bridge St, Denton, MD 21629
  • /27

    $265,000

    • 2 Beds
    • 1 Bath
    • 1,092 Sq Ft

    10819 Greensboro Rd, Denton, MD 21629

    This home will be a Total Renovation in 2026. Consisting of 2 BR and 1 Bath. Situated on almost a half ac. Lovely back yard, and new Well, Septic has been inspected and is in acceptable working condition. Stones have been added to the driveway . A few more touches and it is move in ready. Don't wait to view this Newley redone home.

    Barbara Beaudet Brenton Realty Group

    10819 Greensboro Rd, Denton, MD 21629
  • /2

    $499,999

    New Construction
    • 4 Beds
    • 2 Baths
    • 1,613 Sq Ft

    25660 Cherry Blossom Ln, Denton, MD 21629

    Beautiful to be built new construction on 1.8 acres just outside Denton. This home offers 4 bedrooms, 2 full baths, great open kitchen with island, pantry, separate laundry room, large family room plus dining area. The crawl space will be conditioned for total peace of mind. The garage is huge measuring 32x22 and will be fully insulated with R19 Batts insulation. There will be a slider leading to

    Bonnie Johnson Keller Williams Realty

    25660 Cherry Blossom Ln, Denton, MD 21629
  • /33

    $340,000

    Open Sat 10AM - 12PM $29K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,560 Sq Ft

    401 S 2nd St, Denton, MD 21629

    This charming 2-story colonial home in Denton offers a perfect blend of classic character and modern updates. Featuring 3 bedrooms and 11⁄2 bathrooms, this well-maintained home is conveniently located close to downtown, giving you easy access to local restaurants, shopping, and community events. Inside, you’ll find beautiful hardwood floors that add warmth and timeless appeal throughout much of

    Wes Russum Coldwell Banker Chesapeake Real Estate Company

    401 S 2nd St, Denton, MD 21629
  • /5

    $900,000

    • Land
    • 26.15 Acres
    • $34,417 per Acre

    1017 Camp Rd, Denton, MD 21629

    Approximately 27.16 acres of development land located within the Town of Denton. The property is currently zoned UR (Urban Residential). Public water and sewer are available in the area; purchasers should independently verify utility capacity, connection requirements, and all development approvals with the Town of Denton and Caroline County. The property is being offered for sale as raw land. A

    Benjamin Alder The Land Group

    1017 Camp Rd, Denton, MD 21629
  • /55

    $435,000

    $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,720 Sq Ft

    25485 Hignutt Rd, Denton, MD 21629

    Welcome to 25485 Hignutt Rd. in Denton, MD — a completely renovated 3-bedroom, 2.5-bath home situated on nearly a half-acre in a peaceful country setting, while still being just minutes from all the shopping, dining, and conveniences Denton has to offer. This beautifully updated and meticulously maintained home is truly move-in ready. Inside, you'll find durable luxury vinyl plank flooring

    Justin Pokrywka Taylor Properties

    25485 Hignutt Rd, Denton, MD 21629
  • /32

    $450,000

    • 1 Bed
    • 1.5 Baths
    • 1,596 Sq Ft

    23629 Willow Pond Rd, Denton, MD 21629

    A Distinctive Live/Work Opportunity on Marylands Eastern Shore. This prime location tucked away between Easton & Denton, is this remarkable and beautifully maintained, 6.18 acre property that combines the tranquility of a pastoral countryside with the practicality of a live/work lifestyle. Set on 6.18 acres of gently rolling land, this is One Lot, divided into 2 parcels, (one 2 .18 Acre and one 4

    Stephany Barrett Long & Foster Real Estate, Inc.

    23629 Willow Pond Rd, Denton, MD 21629
  • /40

    $350,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,056 Sq Ft

    608 Market St, Denton, MD 21629

    Full Re-Hab 2023! Home shows well. The best of Downtown Living! This refurbished Farmhouse, has all the feels of intown country living with all the new modern ammenties! Large Eat- in Kitchen with Tons of Storage! Family Room with Fireplace, leads to a side yard Patio for entertaining! Upstairs you will find three nice size Bedrooms, 2 Full Baths, and a Loft area. Attic has finished space

    Kathleen Brenton Brenton Realty Group

    608 Market St, Denton, MD 21629
  • /3

    $69,000

    • Land
    • 2.08 Acres
    • $33,173 per Acre

    0 Goldsboro Rd Unit MDCM2006720, Denton, MD 21629

    Beautiful 2.08 acre flat lot. Was approved for a potential mound system in 1991. All paperwork is included in the disclosures. Buyer to verify well and septic approval before closing.

    Toni Lynne Advance Realty, Inc.

    0 Goldsboro Rd Unit MDCM2006720, Denton, MD 21629
  • /48

    $395,000

    • 4 Beds
    • 2.5 Baths
    • 2,040 Sq Ft

    502 Kathryn Ct, Denton, MD 21629

    Updated + Upgraded - Turn-key 4BR/2.5BA contemporary 2-story home on a culdesac lot backing to trees, near historic downtown Denton - a true gem of an Eastern Shore town, perched on the banks of the Choptank River - but tucked away on a residential court. New flooring + paint throughout, new granite counters, new kitchen appliances, new fixtures. Wide open floorplan boasts tall ceilings, spacious

    Charlene Reaser EXP Realty, LLC

    502 Kathryn Ct, Denton, MD 21629
  • /37

    $299,900

    $10K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,280 Sq Ft

    1624 Blue Heron Dr, Denton, MD 21629

    Move-in ready and thoughtfully updated—this is one you won’t want to miss. Step inside this newly renovated 2,200 sq. ft. townhome located in the heart of Denton, MD. Featuring four spacious bedrooms and 3.5 bathrooms, this home offers a perfect blend of comfort, functionality, and modern design. The entry level includes a versatile first-floor bedroom with a walk-in closet—ideal for guests, a

    Michelle DiDonato Island Realty, LLC

    1624 Blue Heron Dr, Denton, MD 21629
  • /20

    $309,900

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    510 Lincoln St, Denton, MD 21629

    Discover effortless one‐level living in this newly constructed three-bedroom, two-bathroom rancher, completed in 2024 and perfectly positioned in the center of downtown Denton. Modern design, thoughtful upgrades, and an open, airy layout make this home stand out from the moment you step inside. The open-concept living, dining, and kitchen area creates a warm and welcoming flow—ideal for everyday

    Amanda Morgan Brenton Realty Group

    510 Lincoln St, Denton, MD 21629
  • /28

    $669,000

    $131K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,880 Sq Ft

    1108 Camp Rd, Denton, MD 21629

    Price Reduction! Motivated Seller. Welcome to 1108 Camp Street, sits on over 14 acres of land where modern comfort meets elegant design through an extensive list of upgrades that enhance both functionality and style. This home features stunning stone work on both the front and back, framing the house in natural beauty and providing a warm welcome. The meticulously crafted stone walls create an

    Michelle Anderson Coldwell Banker Premier - Rehoboth

    1108 Camp Rd, Denton, MD 21629
  • /31

    $399,000

    $70K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 2,885 Sq Ft

    112 S 5th Ave, Denton, MD 21629

    Reduced, sellers are ready to move on! Homes like this is what they use for Christmas cards, large wrap around porch, entry foyer, detailed fireplaces, hard wood floors, and so much more. This is waiting for the right owner to continue the 126 years this home has stood. Everything in this home is in grand size. Large rooms, make this an easy home for a large family . The house current owners have

    Kat Thompson Benson & Mangold, LLC.

    112 S 5th Ave, Denton, MD 21629
  • /123

    $679,000

    • 3 Beds
    • 4 Baths
    • 2,756 Sq Ft

    4 S 1st St, Denton, MD 21629

    Outstanding Business Opportunity! Rare Find with-in Downtown Denton! Property would make an excellent Restaurant, Bar, great Venue , or a Large Victorian Home! Features include but not limited to Residential, Commerical or Mixed Use. Large Wrap around Porch for entertaining, Patio with plenty of room for seating with Firepit. Park like setting with Open Space and Large Pond! Town ERU's are

    Kathleen Brenton Brenton Realty Group

    4 S 1st St, Denton, MD 21629
  • /62

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft

    1010 S 2nd St, Denton, MD 21629

    Nestled on the edge of town, 1010 S 2nd Street delivers the convenience of in-town living without in-town taxes. Situated on 1.06 beautifully landscaped acres with mature plantings, this 3-bedroom, 2-bath home offers a spacious feel inside and out. Interior features include hardwood, LVP, and tile flooring, along with a cozy pellet stove fireplace insert for efficient heating, complemented by hot

    Roger Boyce Chesapeake Real Estate Associates, LLC

    1010 S 2nd St, Denton, MD 21629
  • /37

    $299,000

    • 3 Beds
    • 1 Bath
    • 1,222 Sq Ft

    7192 American Corner Rd, Denton, MD 21629

    Come make this updated and move in ready rancher your new home. Considerable improvements have been made over the last two years to include the following. This home has a new deep well, new septic system, new tankless propane water heater, new washer/dryer. new range and refrigerator, new roof, new siding, new hvac, renovated bathroom, new flooring, fresh paint, new privacy and chain link fencing

    Andrew Beaven Wright Real Estate

    7192 American Corner Rd, Denton, MD 21629
  • /11

    $3,700,000

    8019 Patten Rd, Denton, MD 21629

    Poultry farm features a total of 60.57 acres (40 acres tillable, 8.5 acres wooded, 1.5-acre retention pond) and a 40x72 shop that has garage parking and a separate space that could be finished for permanent living. Located approx. 5 miles from the DE line. Expired site evaluation-no septic on property.

    Tambra Reagan CALLAWAY FARNELL AND MOORE

    8019 Patten Rd, Denton, MD 21629
  • /50

    $609,000

    • 5 Beds
    • 2.5 Baths
    • 2,920 Sq Ft

    24276 Asbury Dr, Denton, MD 21629

    Nestled in the shadows of the Choptank River is a meticulously maintained home in the water-privileged neighborhood of Asbury. Beautiful Expansive lot size gives you the privacy needed within a walkable neighborhood. The flat level lot opens up future pool and other amenity possibilities. Sit in your rocker with a cocktail while enjoying the dream turned into a reality of a wrap-around porch. A

    Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    24276 Asbury Dr, Denton, MD 21629
  • /20

    $850,000

    $250K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,320 Sq Ft

    6401 Laurel Grove Rd, Denton, MD 21629

    Nestled on an expansive 52.08-acre estate, this stunning ranch-style farm offers a harmonious blend of luxury and tranquility, perfect for those seeking an exclusive lifestyle in a serene rural setting. The property boasts a traditional architectural design, complemented by aluminum siding that enhances its timeless appeal. Step inside to discover a thoughtfully designed interior that exudes

    Michelle Anderson Coldwell Banker Premier - Rehoboth

    6401 Laurel Grove Rd, Denton, MD 21629
  • /19

    $850,000

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

    6401 Laurel Grove Rd, Denton, MD 21629

    Nestled on an expansive 52.08-acre estate, this stunning ranch-style farm offers a harmonious blend of luxury and tranquility, perfect for those seeking an exclusive lifestyle in a serene rural setting. The property boasts a traditional architectural design, complemented by aluminum siding that enhances its timeless appeal. Step inside to discover a thoughtfully designed interior that exudes

    Michelle Anderson Coldwell Banker Premier - Rehoboth

    6401 Laurel Grove Rd, Denton, MD 21629
  • /23

    $190,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,860 Sq Ft

    1507 Blue Heron Dr, Denton, MD 21629

    3-Story Townhome Ready for Its New Owners!Home offers 3 bedrooms and 2.5 baths with a functional layout and comfortable living spaces. The spacious first floor features an open living area and convenient half bath for guests.The second floor includes two bedrooms, a full bath, and laundry area, providing everyday convenience. The third-floor primary suite offers a private retreat with a

    KL Harris Keller Williams Select Realtors of Cambridge

    1507 Blue Heron Dr, Denton, MD 21629
  • /30

    $355,000

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft

    8140 Haven St, Denton, MD 21629

    This charming ranch-style home, built in 1986, offers a perfect blend of comfort and functionality. Minutes to Tuckahoe Creek boat ramp! With 1,300 sq. ft. of well-designed space, it features three inviting bedrooms and two full bathrooms, including a primary suite with a walk-in closet and a tub/shower. The traditional floor plan is enhanced by built-ins and ceiling fans, creating a cozy

    Mary Haddaway Benson & Mangold, LLC

    8140 Haven St, Denton, MD 21629
  • /67

    $659,000

    $20K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,744 Sq Ft

    132 Deep Shore Rd, Denton, MD 21629

    Welcome to 132 Deep Shore Rd—an inviting homestead set on more than 3 acres of beautifully maintained gardens, thoughtfully designed outdoor spaces, and versatile outbuildings. From greenhouse and herb beds to a dedicated drying room and casual nooks for lounging, every corner invites you to savor the seasons. Inside, this spacious home offers over 2,700 sq ft with 4 bedrooms and 2.5 baths. An

    Roger Boyce Chesapeake Real Estate Associates, LLC

    132 Deep Shore Rd, Denton, MD 21629
  • /2

    $272,000

    $2K PRICE INCREASE
    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    325 Carter Ave, Denton, MD 21629

    Excellent cozy home just waiting for you in the town of Denton with the small town atmosphere and a lot of amenities. Affordably priced, close to shopping, easy commute to the Western Shore and close enough to Delaware and Maryland beaches. Come see today because this home will not last long.

    George Thompson Long & Foster Real Estate, Inc.

    325 Carter Ave, Denton, MD 21629
  • /59

    $1,500,000

    • 4 Beds
    • 3 Baths
    • 3,358 Sq Ft

    23071 Tuckahoe Springs Dr, Denton, MD 21629

    Beautifully positioned along the deep protected waters of the Tuckahoe, this exceptional residence has been transformed through an extensive renovation that blends timeless design with comfortable waterfront living. Every improvement was carefully planned, resulting in a home that feels as inviting as it is impressive. The heart of the home is the custom kitchen, where blue marble countertops,

    Sydney Johnson Cohee Sharon Real Estate P.C.

    23071 Tuckahoe Springs Dr, Denton, MD 21629
  • /74

    $525,000

    • 3 Beds
    • 3 Baths
    • 3,088 Sq Ft

    22005 Main St, Hillsboro, MD 21641

    PLEASE NOTE that the Owner has listened to the current market, Price has been reduced to $525,000. It is a property of beautifully preserved quality on 3⁄4 of an acre in an urban setting. Most unusual! When compared to equivalent historic properties it is now very competitively priced! This fine, brick dwelling originating from the18th c. is situated in Hillsboro on Maryland's peaceful Eastern

    Nancy McGuire Maryland Heritage Properties

    22005 Main St, Hillsboro, MD 21641

Showing Results 1 - 40, Page 1 of 2

How to Buy a Home How to Finance a Home How to Sell a Home