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Homes for Sale in 21629

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  • /102

    $1,395,000

    • 4 Beds
    • 3.5 Baths
    • 3,356 Sq Ft

    23296 Wilder Way, Denton, MD 21629

    Right out of HGTV! Custom Built in 2020, this 3,350+/- sq ft one-level home offers an abundance of amenities including high ceilings, 4 bedrooms, 3.5 Baths, large open floorplan with huge gourmet kitchen with quartz/ss appliances, separate pantry, family room with stacked stone gas fireplace. The Primary Bedroom is located at one end of the house and includes a large bath with double vanity,

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (443) 232-1392

    23296 Wilder Way, Denton, MD 21629
  • /71

    $500,000

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

    25699 Auction Rd, Federalsburg, MD 21632

    Mortgage savings may be available for buyers of this home.Discover the perfect blend of comfort, versatility, and investment potential in this completely remodeled 1,986 sq ft home set on 17.36 acres. Every detail has been thoughtfully upgraded—from new luxury vinyl plank flooring and Advantech subfloors to a fully replaced middle beam for lasting structural integrity. Nearly all windows

    Barbara McCaffrey Redfin Corp

    25699 Auction Rd, Federalsburg, MD 21632
  • /3

    $465,000

    • 4 Beds
    • 3 Baths
    • 3,206 Sq Ft

    8534 Duffers Dell, Denton, MD 21629

    Don't Miss This Stunning Cape Cod w/ A Spacious Open Floor Plan and Welcoming Front Porch. You Will Love The Two Story Great Room w/ Pine Floors and Ceiling As Well As Wood Fireplace That Is Open To The Bright Kitchen w/large Island, Granite Counters. Retreat To The First Floor Primary Suite w/ Full Bath and Walk In Closet. The Home Also Boasts A Beautiful Formal Dining Room and Office / Living

    Vincent Damico RE/MAX Advantage Realty

    8534 Duffers Dell, Denton, MD 21629
  • /40

    $395,000

    • 4 Beds
    • 2.5 Baths
    • 2,138 Sq Ft

    1111 Trice Meadows Cir, Denton, MD 21629

    Welcome to 1111 Trice Meadows Circle in Denton, MD!This charming 4-bedroom, 2-bath detached single-family home offers comfort, style, and convenience in the sought-after Trice Meadows community. Featuring an open and inviting floor plan, this home is perfect for both everyday living and entertaining.The spacious living room flows seamlessly into a modern kitchen, complete with ample

    LaTanya Drayton United Real Estate Premier

    1111 Trice Meadows Cir, Denton, MD 21629
  • /34

    $480,000

    • 3 Beds
    • 2 Baths
    • 2,132 Sq Ft

    25790 Herring Ln, Denton, MD 21629

    Beautiful 3 bedroom 2 bathroom rancher sitting on just over 3 acres. Quiet, friendly neighborhood with plenty of space for your animals too! There are Brazilian hardwoods running through most of the home. Both bathrooms have been remodeled. Generous sized bedrooms with large closets, primary bedroom has two with his and her closets. Tankless instant hot water. Oversized two car garage. It’s also

    Elizabeth Tryon Meredith Fine Properties

    25790 Herring Ln, Denton, MD 21629
  • /49

    $435,000

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    8556 Tuckahoe Rd, Denton, MD 21629

    USDA ELIGIBLE -"LOW TO NO DOWN" PAYMENT with loan qualification -PLUS **Seller offering 10,000 CLOSING COST HELP with acceptable offer by 8/31/25 ** WON'T LAST LONG WITH THESE OFFERINGS -Welcome to 8556 Tuckahoe Road—your gorgeous private retreat on over an acre just minutes from Tuckahoe State Park! Step outside to your own backyard oasis featuring a large, fenced-in inground pool,

    Kathleen Armiger Coldwell Banker Realty

    8556 Tuckahoe Rd, Denton, MD 21629
  • /47

    $625,000

    • 3 Beds
    • 2 Baths
    • 1,616 Sq Ft

    300 S 1st St, Denton, MD 21629

    Peaceful Living on the Choptank River!!! One level Living! Offering 3 Bed and 1.5 Bath. Home features an open Floor Plan with Large Living Room w/ Gas Burning Stove., Spacious Kitchen with Tons of Storage, Breakfast Bar, and plenty of space for your Table and Chairs! Primary Bedroom facing the Water with Great Waterfront Views. Home also features a paved driveway with 2 door garage and a full

    Kathleen Brenton Brenton Realty Group

    300 S 1st St, Denton, MD 21629
  • /45

    $724,900

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

    28402 Liden School Rd, Denton, MD 21629

    This home is on one acre with an additional 15.77 acres - possibly one additional acre in deed. This home says "home from the time you drive up the drive and into this gorgeous rancher with comfort written all over." The kitchen has all stainless steel appliances and a large pantry. Large Island with cabinetry as well as seating for meals or snacks or just relaxing in the kitchen. The pellet

    Bonnie Duley Long & Foster Real Estate, Inc.

    28402 Liden School Rd, Denton, MD 21629
  • /30

    $430,000

    • 4 Beds
    • 2.5 Baths
    • 3,838 Sq Ft

    1111 Daylily Ln, Denton, MD 21629

    Welcome to your dream home at 1111 Daylily Ln, nestled in the desirable community of Cattail Commons. This spacious 4-bedroom, 2.5-bath home offers the perfect blend of functionality and style, thoughtfully designed for everyday living and effortless entertaining.The bright and airy main level features an open-concept kitchen and dining area, ideal for hosting gatherings, along with a

    Joni Barrow Keller Williams Realty

    1111 Daylily Ln, Denton, MD 21629
  • /59

    $374,000

    • 4 Beds
    • 1.5 Baths
    • 2,974 Sq Ft

    107 Butler Dr, Denton, MD 21629

    Charming Home with Timeless Character, Modern Updates & Expansion PotentialStep into this beautifully maintained 4-bedroom, 1.5-bath home that perfectly blends classic charm with thoughtful modern updates. Nestled on a generous 1/3-acre fenced-in town lot, this property offers the privacy and space you’ve been looking for, complete with mature shade trees that create a peaceful,

    Justin Pokrywka Meredith Fine Properties

    107 Butler Dr, Denton, MD 21629
  • /62

    $365,900

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

    1010 S 2nd St, Denton, MD 21629

    1010 S 2nd Street offers in-town living WITHOUT in-town Taxes!!! This home rests at the edge of town on 1.06 acres with mature plantings. This 3-bed 2-bath home boasts hardwood, LVP, and tile floors. A fireplace insert for the pellet stove for heat, while the seller uses the Hot water baseboard as a backup. Full basement for additional entertaining or storage. Screened-in porch overlooks

    Roger Boyce Chesapeake Real Estate Associates, LLC

    1010 S 2nd St, Denton, MD 21629
  • /34

    $440,000

    • 4 Beds
    • 2.5 Baths
    • 3,096 Sq Ft

    1207 Painted Fern Rd, Denton, MD 21629

    Welcome to 1207 Painted Fern Road — a beautifully maintained and thoughtfully upgraded home nestled in the heart of Denton. This spacious residence offers the perfect blend of modern comfort, functional design, and serene natural surroundings.Step inside to a dramatic two-story foyer that sets an elegant tone for the rest of the home. To the right, a private office provides an ideal space

    Trudie Colvin Coldwell Banker Realty

    1207 Painted Fern Rd, Denton, MD 21629
  • /30

    $385,000

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    313 S 3rd St, Denton, MD 21629

    Meticulously Maintained & Move In Ready!! Many recent Improvements to this 3 bedroom, 2 bath, Open floor plan rancher with Large Yard, Deck, Multiple Organically prepped Gardens (including an asparagus) ready for your harvest this summer, Covered Porch, Pool with Decking, Oversized 2 Car Garage. Top is off with a large bonus room ready to make it your own! Plenty of off street parking. Close

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    313 S 3rd St, Denton, MD 21629
  • /13

    $389,999

    • 3 Beds
    • 2 Baths
    • 1,764 Sq Ft

    314 Kerr Ave, Denton, MD 21629

    Huge open backyard will easily accommodate a pool, playground, or outdoor games. There is a handicap ramp in the garage entry. The internal walls will allow wheelchair passage (37.5 inches). work bench in garage, shelving installed in garage. New carpeting installed in the three bedrooms on June 27, 2025. The new roof was put on and finished June 11,2025. Seller is motivated.

    Donald Schloss Taylor Properties

    314 Kerr Ave, Denton, MD 21629
  • /52

    $344,900

    • 3 Beds
    • 2 Baths
    • 1,961 Sq Ft

    7881 Dyer Rd, Denton, MD 21629

    Country location - 3BR, 2BA Home on Private 1± Acre Lot!This beautifully maintained home offers comfort, updates, and space both inside and out. Enjoy peace of mind with recent upgrades including a new well, septic system, HVAC, roof, and driveway. The home features gleaming wood floors, a bright, updated kitchen and bathrooms, and flexible living spaces – potential for a first-floor

    Valerie Brown Charles C. Powell, Inc. Realtors

    7881 Dyer Rd, Denton, MD 21629
  • /3

    $109,895

    • 3 Beds
    • 2 Baths
    • 2,312 Sq Ft

    9709 Foy Rd, Denton, MD 21629

    Priced To Sell Fast! Investor Alert! Renovate & Resell, Buy and Hold or Tear Down and Develop. Major Rehab Needed, City Will Require Permits. Per the City Lot Can be Split into 3 Parcels. 1.72 Acres Total. 3 Level Colonial, Spacious Kitchen, Spacious Bedrooms, Hardwood Floors, Much More!! Just Waiting For Your Personal Cosmetics and Renovations to Make it Shine. Close to Schools, Shopping and

    Matthew Altizer ANR Realty, LLC

    9709 Foy Rd, Denton, MD 21629
  • /35

    $350,000

    • 4 Beds
    • 2 Baths
    • 1,326 Sq Ft

    1203 Tuckahoe Ct, Denton, MD 21629

    Take a look at this charming 4 BR 2 Bath Cape Cod. Many improvements have been done to make this place your sweet dream. The kitchen has all new cabinets with a new gas range and Corian countertops and the living room has new vinyl flooring. The kitchen and the dining area overlook the new contracted deck that leads to the large backyard with 2 sheds, 1 being new (2023), along with new

    Stephen Brown Iron Valley Real Estate Ocean City

    1203 Tuckahoe Ct, Denton, MD 21629
  • /21

    $269,000

    • 3 Beds
    • 1 Bath
    • 1,019 Sq Ft

    529 N 6th St, Denton, MD 21629

    Welcome to this beautifully maintained 3 bedroom, 1 bath home that blends classic character with modern updates. Inside, you’ll find original hardwood floors that add warmth and charm throughout the living space.Enjoy a spacious backyard perfect for entertaining or relaxing, plus a brand new oversized back deck completed in 2025, ideal for outdoor gatherings. The home also features new

    Cody Weese Weese Properties, LLC

    529 N 6th St, Denton, MD 21629
  • /20

    $199,900

    • 3 Beds
    • 1 Bath
    • 1,904 Sq Ft

    21948 Main St, Hillsboro, MD 21641

    This home is high on a hill so little chance of flooding from the Choptank River that is across the street -- with some winter views. The park is across the street with a ramp for boats, kayaks, and canoes. The home has 3 bedrooms and a small room for office or nursery or whatever you want it to be;, and one full bath -- all upstairs. The front porch entrance opens to a foyer and the living

    Bonnie Duley Long & Foster Real Estate, Inc.

    21948 Main St, Hillsboro, MD 21641
  • /30

    $289,000

    • 3 Beds
    • 1.5 Baths
    • 1,092 Sq Ft

    312 Fountain Ave, Denton, MD 21629

    Charming in-town living in this Beautifully Remodeled 3-Bedroom Rancher! Updates include Fresh Paint, NEW Luxury Vinyl Plank Flooring, NEW Kitchen Cabinets, NEW Tile Backsplash and NEW Quartz Countertops! Ceiling Fans in all Bedrooms, Living Room and Dining area to ensure comfort throughout. Turn-Key and ready for you to move right in! Situated on a large Corner Lot with a Spacious Driveway

    Pamela Ackermann-Doll RE/MAX Executive

    312 Fountain Ave, Denton, MD 21629
  • /25

    $299,900

    • 4 Beds
    • 3.5 Baths
    • 2,640 Sq Ft

    1904 Blue Heron Dr, Denton, MD 21629

    Welcome to Mallard Landing and your own private townhouse in the quiet, peaceful outskirts of Denton. This charming 2,640 sq ft townhouse offers thoughtfully designed living space, including four spacious bedrooms, four bathrooms, a bar-counter dine-in kitchen, and a formal dining room. As you step inside the front door, you’ll notice three levels of spacious room sizes, a walk-in closet in the

    Ralph Harvey ListWithFreedom.com

    1904 Blue Heron Dr, Denton, MD 21629
  • /20

    $199,900

    • 2 Beds
    • 1.5 Baths
    • 1,196 Sq Ft

    341 Academy Ave, Denton, MD 21629

    Welcome to Denton! Small town living with all the amenities nearby! Cute townhouse with two bedrooms, one and a half baths with washer/dryer in unit. Low maintenance and No HOA. Walk into town for coffee or a meal then walk down to the water along the Choptank River. Boat ramp and kayak/paddle board launch minutes away. Super Walmart and other shopping just minutes away. Don't miss this

    Jason Dey Kevin Dey Realty

    341 Academy Ave, Denton, MD 21629
  • /40

    $475,000

    • 3 Beds
    • 2 Baths
    • 1,952 Sq Ft

    8452 Harmony Rd, Denton, MD 21629

    Huge price improvement! Your Own Slice of Paradise!Pride of ownership shines throughout this beautifully updated rancher, perfectly nestled on 4 acres of serene countryside complete with a pond stocked with koi, catfish and goldfish—a dream setting for nature lovers and outdoor enthusiasts alike. Step inside and fall in love with the modern touches and thoughtful upgrades throughout.

    Tracey Bellotte Coldwell Banker Realty

    8452 Harmony Rd, Denton, MD 21629
  • /29

    $325,000

    • 3 Beds
    • 2.5 Baths
    • 2,508 Sq Ft

    614 Market St, Denton, MD 21629

    PRICE IMPROVEMENT! Welcome to 614 Market Street. Situated on a corner lot, conveniently located in town of Denton. Just a short walk to downtown to enjoy the local shops, eateries, parks, and the beautiful Choptank River. This historical, charmer will not let you down. Home features a spacious, traditional floor plan, table space in the large kitchen, separate/formal dining room, large home

    Michael Bozek Michael J. Bozek

    614 Market St, Denton, MD 21629
  • /49

    $310,000

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    8409 Harmony Rd, Denton, MD 21629

    Charming Single-Level Living on 1.14 Acres – Modern Updates & Income Potential!Welcome to this beautifully updated, move-in-ready home set on 1.14 peaceful acres with mature trees and dual road access (Towers Rd. & Harmony Rd.). Offering comfort, versatility, and potential rental income of up to $2,000/month, this property is a rare find.Interior HighlightsBright, open

    Sandra Gendleman Long & Foster Real Estate, Inc.

    8409 Harmony Rd, Denton, MD 21629
  • /9

    $99,000

    • Land
    • 3.05 Acres
    • $32,459 per Acre

    10440 Burrsville Branch Rd, Denton, MD 21629

    3+ ACRES PARTLY WOODED AND BACKS TO FARMLAND. NOT LOCATED IN A COMMUNITY AND NO HOA. (PLAT REFLECTS 3.235 +- ACRES, WHILE SDAT REFELCTS 3.05+- ACRES) PROPERTY IS IMPROVED WITH A 2 STORY HOME THAT WAS BUILT IN 1900 . THIS IS A TEAR DOWN OR PERHAPS POSSIBLY A FIXER UPPER. ***** DO NOT ENTER RESIDENCE***** THERE IS ALSO AN EXISTING WELL AND SEPTIC ON THE PROPERTY. HOUSE, WELL AND SEPTIC ARE

    Deborah Callahan Benson & Mangold, LLC

    10440 Burrsville Branch Rd, Denton, MD 21629
  • /10

    $249,000

    • Land
    • 0.23 Acre
    • $1,082,609 per Acre

    520 S 5th Ave, Denton, MD 21629

    LET’S MAKE A DEAL***INVEST IN A PRIME MULTI USE SITE * DESIRABLE LOCATIONS * BUYERS CHOICEDEVELOP NOW? Or HOLD AND LET TIME INCREASE YPUR PROFIT OPPORTUNITY.... FOUR 10,000 SQ FT ADJOINING LOTS IN A GREAT IN TOWN SETTING S DUPLEX. IS ONE OF SEVERAL PERMITTED USES SO EASILY to build total 8 UNITS. Office, Shop or Studio with 2nd floor Residential for a Live Work

    Phil Riordan Meredith Fine Properties

    520 S 5th Ave, Denton, MD 21629
  • /55

    $950,000

    • 4 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    11142 Log Cabin Rd, Denton, MD 21629

    Welcome to 11142 Log Cabin Road! This unique property offers the perfect combination of residential living and valuable commercial space, all on one expansive, 4.53 acre lot. This beautiful colonial-style home has great curb appeal with its classic look, neatly trimmed landscaping, and a spacious front yard shaded by mature trees. The main home spans over 2,700 square feet and features four

    Courtney Gallagher Keller Williams Realty Central-Delaware

    11142 Log Cabin Rd, Denton, MD 21629
  • /54

    $250,000

    • 4 Beds
    • 1.5 Baths
    • 2,406 Sq Ft

    108 S 2nd St, Denton, MD 21629

    Historic charm meets endless potential in this spacious corner-lot home in the heart of downtown Denton—formerly home to the beloved local flower shop! With 4 bedrooms and 1.5 bathrooms, this well-maintained property offers incredible space, character, and small-town walkability.From the welcoming front porch to the large family room that opens to an oversized deck, this home is perfect

    Crystal Smith RE/MAX Executive

    108 S 2nd St, Denton, MD 21629
  • /25

    $259,000

    • Studio
    • 1,820 Sq Ft

    207 Gay St, Denton, MD 21629

    Price Improvement! Great investment. Perfect opportunity for an investor or owner-occupied duplex as first floor unit generates $1100/month and second floor unit is currently vacant.Conveniently located, multi-family in Downtown Denton with the Denton Police Department directly across the street.Vinyl siding, replacement windows, ductless mini split HVAC and off-street parking in the rear.

    Andrew Beaven Wright Real Estate

    207 Gay St, Denton, MD 21629
  • /24

    $153,000

    • Land
    • 3.00 Acres
    • $51,000 per Acre

    0 Asbury Dr, Denton, MD 21629

    Discover your ideal homesite in the scenic Asbury on the Choptank community, where peaceful living meets convenient access. This expansive 3-acre lot is perc approved for a three-bedroom septic system.Within this sought-after community, residents enjoy well-maintained roads, a private nature trail, and exclusive access to a community deepwater dock on the Choptank River. Ideal for boating

    Coard Benson Benson & Mangold, LLC

    0 Asbury Dr, Denton, MD 21629
  • /71

    $1,150,000

    • 4 Beds
    • 3.5 Baths
    • 4,092 Sq Ft

    8816 Dorothy Ln, Denton, MD 21629

    Nestled on over six acres of pristine land with direct access to the Choptank River, this contemporary waterfront estate offers the ultimate in Eastern Shore luxury living. Designed to impress, the home features four spacious bedrooms, three and a half baths, and soaring cathedral ceilings that crown a dramatic two-story living room with floor-to-ceiling windows—flooding the home with natural

    Dustin Parker The Parker Group

    8816 Dorothy Ln, Denton, MD 21629
  • /73

    $545,000

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

    22005 Main St, Hillsboro, MD 21641

    This fine, brick dwelling originating from the18th c. is situated in Hillsboro on Maryland's peaceful Eastern Shore. Hillsboro, nestled along the Tuckahoe River, conveniently located to all that is important to the Eastern Shore's sought-after lifestyle.The WILLIAM SMITH HOUSE, built in 1794, exemplifies the world of a successful Grain Merchant living in an important hub for grain and

    Nancy McGuire Maryland Heritage Properties

    22005 Main St, Hillsboro, MD 21641
  • /20

    $70,000

    • 3 Beds
    • 1 Bath
    • 768 Sq Ft

    25035 Auction Rd, Denton, MD 21629

    Little rough and sold AS-IS. Near chicken houses. Inspections welcome at buyers expense. I don't want to say shed or garage is tear down because enterprising individual may 'Repair' without permits. The electric is still on but suggest day time showings. Make an offer!

    Michael Shipley Benson & Mangold, LLC.

    25035 Auction Rd, Denton, MD 21629
  • /15

    $135,000

    • 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
  • /8

    $225,000

    • Land
    • 0.06 Acre
    • $3,750,000 per Acre

    245 Briarwood Cir, Denton, MD 21629

    LETS MAKE A DEAL****Hard to Find Great Construction Project waiting for you.Improved 4 adjoining townhouse parcels with concrete slab (check with governmental officials for usability?)Or remove and build new for this special block of 4 town house lots. Beginning of the Sandy Meadows community that is its own block offering privacy outside of crowded downtown for you to Build and sell or

    Phil Riordan Meredith Fine Properties

    245 Briarwood Cir, Denton, MD 21629
  • /8

    $225,000

    • Studio

    245 Briarwood Cir, Denton, MD 21629

    Improved 4 adjoining townhouse parcels with concrete slab (check with governmental officials for usability?)Beginning of the Sandy Meadows community that is its own block offering privacy outside of crowded downtown for you to Build and sell or rent.Listing shows one lotLots 55, 56, 57 & 58 This is a unique opportunity for small project in a nice setting.Call for details.

    Phil Riordan Meredith Fine Properties

    245 Briarwood Cir, Denton, MD 21629
  • /6

    $85,000

    • Land
    • 1.15 Acres
    • $73,913 per Acre

    0 Laurel Ln, Denton, MD 21629

    Beautiful, wooded lot ready to be built on available in established Forest Landing. Conveniently located between Denton and Easton. Lot has approved perc for a 4 bedroom mound system. Community offers a private beach area, picnic tables, great spot to launch your canoe or kayak or do a little fishing. Not many opportunities to build your next home in a mature neighborhood left around.

    Michael Bozek Michael J. Bozek

    0 Laurel Ln, Denton, MD 21629
  • /16

    $249,900

    • Land
    • 3.40 Acres
    • $73,500 per Acre

    0 Shore Highway-404 Unit MDCM2004050, Denton, MD 21629

    Farm land or a Home site. Convenient to Denton and 404. 3 parcels totaling 21.11 acres are included in the offering. Tillable land and wooded. Great spot for someone with horses or that wants to hunt. Perk approval on Parcel 83. Approx. 3.7 tillable acreage.

    Eddie Matthews Benson & Mangold, LLC

    0 Shore Highway-404 Unit MDCM2004050, Denton, MD 21629
  • /2

    $21,000

    • Land
    • 0.18 Acre
    • $116,667 per Acre

    523 High St, Denton, MD 21629

    Check with the town on building your home on this lot.

    Pamela Geib Long & Foster Real Estate, Inc.

    523 High St, Denton, MD 21629

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