Denton Homes under $500,000

Denton Homes under $500,000

Welcome to Denton, Maryland – a charming town nestled in the heart of Caroline County, where small-town charm meets modern convenience. With its rich history, friendly community, and stunning natural beauty, Denton is the perfect place for families, young professionals, and retirees alike.

Denton boasts a vibrant downtown area filled with quaint shops, delightful eateries, and cultural attractions. Stroll through the historic streets and you’ll discover the Caroline County Courthouse, a beautiful example of 19th-century architecture. The local parks and scenic waterways offer endless opportunities for outdoor activities, from kayaking on the Choptank River to enjoying a leisurely picnic in one of the many green spaces.

One of the most appealing aspects of Denton is its affordability. With homes available for under $500,000, this charming town provides a fantastic opportunity for homebuyers looking to settle in a welcoming community without breaking the bank. Whether you’re searching for a cozy single-family home, a modern townhouse, or a spacious property with room to grow, Denton has a diverse selection of real estate options that cater to every lifestyle and budget.

With a strong sense of community, excellent schools, and a wealth of recreational activities, Denton is not just a place to live; it’s a place to thrive. Experience the warmth and hospitality of this lovely town, and discover why so many are choosing to call Denton home. Come explore the possibilities and find your dream home in this delightful Maryland gem!

Newest Denton Homes under $500,000

no property photo
$379,000
3 Beds ⋅ 3 Baths
This charming ranch-style home, conveniently located outside of Denton, offers a perfect blend of comfort and functionality. Set on a partially wooded 1-acre lot, the property features a level landscape with both front and rear yards, ideal for outdoor gatherings or peaceful retreats. The screened porch is perfect for enjoying a relaxing evening or hosting a crab feast. With 3 bedrooms and 3 full bathrooms, this well-maintained residence boasts 2026 sq ft of living space, providing ample room for relaxation and entertainment. The property includes not one, but two garages-an attached 2 bay garage and a detached 2 bay garage with workshop-offering plenty of space for projects as well as storage and parking options. Located in a tranquil rural setting, this home is a haven for those seeking a peaceful lifestyle while still being conveniently accessible. Embrace the charm of country living with modern comforts, making this property a true sanctuary to call home.

8654 Legion Rd, Denton

Listing courtesy of Wright Real Estate. Contact:

25900 Shore Hwy, Denton
$340,000
4 Beds ⋅ 1 Baths
This charming ranch-style home, nestled in the desirable Denton area, offers a perfect blend of comfort and functionality. With 1,858 square feet of thoughtfully designed living space, this residence features four bedrooms, ideal for guests or multi-generational living. The heart of the home is the spacious eat-in kitchen. The kitchen is equipped with essential appliances, including a stove, refrigerator, ensuring that daily tasks are a breeze. The traditional floor plan offers a warm and welcoming atmosphere, the full bathroom features a tub shower. Step outside to discover your own personal oasis on 1.44 acres, complete with a private pool-ideal for summer fun and relaxation. The property also boasts a side-entry detached garage with space for three vehicles, along with ample driveway parking for guests. This home is not just a place to live; it's a sanctuary where memories are made. With its inviting features and spacious layout, it's ready to welcome you home. Don't miss the opportunity to make this delightful property your own!

25900 Shore Hwy, Denton

Listing courtesy of Benson & Mangold, LLC. Contact:

7922 Detour Rd, Denton
$395,000
3 Beds ⋅ 2 Baths
Completely Renovated from Top to Bottom and No HOA or Community Restrictions! Enjoy the best of country living in this beautiful 3 bedroom, 2 bath rancher, tucked away on a quiet road less traveled! Situated on a spacious, level ¾-acre lot, this home offers plenty of room to relax, entertain, and enjoy the peaceful surroundings. Take in the scenic views of open farmland while appreciating the added privacy of a backyard that backs to trees. Renovated from top to bottom, this home features an impressive list of updates, including a NEW roof, windows, siding, flooring, kitchen, bathrooms and so much more! Thoughtfully updated throughout, this home offers modern style, comfortable one-level living, and the peace of mind of knowing so much of the work has already been done for you. Again, there's NO HOA, NO COMMUNITY RESTRICTIONS! Enjoy the freedom of owning your own piece of the countryside without HOA fees or community imposed restrictions. With a spacious property, there's plenty of room to spread out and enjoy your property your way. The home is currently undergoing final finishing touches, with installation of a new septic system in progress. If you've been searching for a beautifully updated home with room to breathe, privacy, and the freedom to enjoy country living, this is your opportunity! Why take on the time, expense, and hassle of renovating when you can move into a home where the work has already been done? Select photos have been digitally enhanced with added color for visual presentation purposes only.

7922 Detour Rd, Denton

Listing courtesy of Clark & Co Realty, LLC. Contact:

23255 Magnolia Hills Rd, Denton
$445,000
3 Beds ⋅ 2 Baths
Welcome home to this spacious 3-bedroom, 2-bath home offering over 2,000 square feet of comfortable living space, situated on a beautiful 1-acre lot! The inviting open floor plan provides a seamless flow between the main living areas, creating the perfect setting for everyday living and entertaining. The desirable split-bedroom floor plan offers added privacy, with the primary suite thoughtfully separated from the additional bedrooms. The spacious living area features a cozy gas fireplace, perfect for those cooler evenings, while the kitchen boasts stainless steel appliances and plenty of space for gathering with family and friends. Step outside and enjoy the wonderful patio area, ideal for outdoor dining, entertaining, or simply relaxing while overlooking the spacious rear yard enclosed with vinyl fencing. The attached 2-car garage provides convenient parking and additional storage space. Recent improvements include an Rinnai water heater for added efficiency and convenience. With over an acre to enjoy, generous living space, and a thoughtfully designed floor plan, this home offers the perfect blend of comfort, functionality, and outdoor enjoyment. Don't miss your opportunity to make this wonderful property your new HOME!

23255 Magnolia Hills Rd, Denton

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

8275 New Bridge Rd, Denton
$379,900
3 Beds ⋅ 1 Baths
COMING SOON!! Well-maintained and updated 3 bedroom rancher offering over 1,300 square feet of living space on over 1.5 acres. Enjoy comfortable living with a spacious living room, a nice-sized kitchen, and a designated dining area with access to the back deck — perfect for grilling, entertaining, or simply relaxing outdoors. The large backyard is partially fenced and offers plenty of room to spread out and enjoy the space. Need extra storage? This property has you covered with two sheds and a metal outbuilding, ideal for storing equipment, tools, and outdoor essentials. The interior has been freshly painted in a neutral color and new flooring is being installed. And, the roof is just 8 years old, offering added peace of mind for years to come. Conveniently located between Routes 50 and 404, making commuting to Easton and Denton a breeze, with easy access to the Bay Bridge and Maryland/Delaware's beautiful beaches. This property offers a great combination of space, updates, storage, and convenience! Make sure you add this one to your MUST SEE list when it officially hits the market!

8275 New Bridge Rd, Denton

Listing courtesy of Clark & Co Realty, LLC. Contact:

1111 Whistling Pine Rd, Denton
$409,000
4 Beds ⋅ 3 Baths
Enjoying a quiet cul-de-sac setting and a private wooded backdrop, this spacious 4-bedroom, 2.5-bath home offers approximately 3,117 square feet of comfortable, well-planned living space in Savannah Overlook. With no through traffic and woods beyond the rear yard, the setting is one of the home's standout features. Inside, a neutral color palette, some newer flooring and fresh paint create a warm, welcoming feel. The spacious gourmet kitchen is designed for both everyday living and entertaining, featuring newer stainless-steel appliances, a generous center island and solid-surface countertops. This area flows to an adjoining casual dining area, where sliding glass doors bring in abundant natural light and provide an easy connection to the outdoor space. The kitchen and dining areas transition seamlessly into the family room, anchored by a dramatic floor-to-ceiling stone fireplace that serves as the focal point of the room. Upstairs, additional flex space adds even more versatility to the floor plan and can easily function as a home office, exercise room, den, media area or second family room, depending on your needs. Important improvements include a new roof in 2021 and a new HVAC system in 2025, featuring an electric heat pump with propane backup. Outside, enjoy established hardscaping, a fully fenced rear yard, a newer storage shed and an existing rough-in for a hot tub. The remarkably versatile two-car garage is another distinctive feature, enhanced with an epoxy-coated floor, extensive organized storage and an easy-to-use retractable screened-door system. This thoughtful setup allows the garage to transition into additional indoor-outdoor living, entertaining or hobby space while retaining its everyday functionality. Thoughtfully maintained and improved over time, 1111 Whistling Pine Road combines generous living space, a desirable lot and the appeal of an established neighborhood community. Conveniently located near Denton's historic downtown, enjoy the charm of a true hometown-USA setting with local shops, restaurants, parks and access to the Choptank River. Route 404 is also nearby, with the Chesapeake Bay Bridge approximately 45 minutes away, providing convenient access toward Annapolis, Baltimore and the Washington metropolitan are

1111 Whistling Pine Rd, Denton

Listing courtesy of Benson & Mangold, LLC. Contact:

211 S 6th St, Denton
$265,000
INVESTOR ALERT! Duplex in Denton. Comprised of one 3 Bedroom, 1 bath unit and one 3 bedroom, 2 bath unit. Separately metered and all electric. Laundry in both units. Unit A is freshly painted and ready for a tenant or owner occupant. Unit B is currently rented.

211 S 6th St, Denton

Listing courtesy of Wright Real Estate. Contact:

533 Gay St, Denton
$270,000
Investment opportunity! This two-unit duplex offers a functional layout with two separate residences, each featuring 2 bedrooms, 1 full bathroom, a kitchen, and in-unit laundry. The property offers separate entrances for each unit, providing privacy and convenience for occupants. With one unit located on the main level and the second unit upstairs, the setup offers flexibility for investors looking to add a multifamily property to their portfolio. Whether you're looking for a traditional rental investment or the opportunity to occupy one unit while renting the other, this property offers plenty of potential.

533 Gay St, Denton

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

104 Riverton Ave, Denton
$467,900
3 Beds ⋅ 3 Baths
Be sure to schedule a tour of this beautiful home in the heart of Denton, small town living at it's best! Built in 1916 and lovingly updated and maintained throughout the years! Beautiful hardwood floors throughout! Lovely updated custom kitchen with soaring vaulted ceilings, radiant heat flooring, walk in pantry, recessed lighting, farm sink and granite counter tops. Mud room with built-in storage and slide out shelving. Replacement windows, mini-split in TV room heats and cools the downstairs, leaded mahogany front door and lovely entry foyer leads to a formal living room. Upstairs you will find three gracious sized bedrooms, a full bath with jacuzzi style tub and laundry room with newer washer and dryer in 2021. A fully insulated attic. A/C is just 3 years old with 2 yrs left on warranty. The basement has been converted into a yoga studio with private entrance, 1/2 bath with room to ad a tub or shower, LVP flooring and electric heat. Additional storage and work room on the other side. This expandable space has endless possibilities, guest suite, art studio, rec room. A glass enclosed atrium is a perfect place to relax and read a book or have a glass of wine or both. Outside is a gardeners paradise with endless mature plantings that come back year after year. 4 large rain barrels keep the water bill in check. The back yard is fully fenced with a brick patio, deck and pavilion for outside entertaining and an inground pool with concrete surround patio and a rock edged goldfish pond. The front of the home features wide brick steps and brick walk way leading up to a freshly painted home with a welcoming front porch with vinyl maintenance-free flooring. Solar panels are leased and will help with the electric costs. Located just a block from the Choptank River and within walking distance to local shops and restaurants this home won't disappoint! Please be sure to stop by the open house on Sunday Oct 4th 11 to 2 pm and if you can't make it be sure to schedule your private tour!!

104 Riverton Ave, Denton

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

23171 Tuckahoe Springs Dr, Denton
$499,000
3 Beds ⋅ 2 Baths
Welcome to Tuckahoe Springs, a peaceful waterfront-oriented community nestled along the scenic Tuckahoe River. This well-maintained 3-bedroom, 2-bath home offers over 1,800 square feet of comfortable one-level living on a 1 acre wooded lot, providing both privacy and a relaxing Eastern Shore setting. The current owners have completed numerous updates, including a new roof in 2024, new double-hung windows throughout, new whole house water treatment system, and new flooring across much of the home. Outside, you'll find a detached two-car garage, additional storage shed, and plenty of room to enjoy the natural surroundings. Outdoor enthusiasts will appreciate the community's proximity to the Tuckahoe River and a public boat landing located less than a mile away, offering convenient access for boating, fishing, kayaking, and enjoying the waterfront lifestyle. Although the property carries a Denton address, its location just across the Tuckahoe River Bridge places you within easy reach of Easton and all that Talbot County has to offer, including shopping, dining, healthcare, and entertainment. Commuters will also appreciate convenient access to Route 50 and other major travel routes. If you're looking for a move-in-ready home with thoughtful updates, a wooded setting, and a location that combines Eastern Shore tranquility with everyday convenience, this property deserves a closer look.

23171 Tuckahoe Springs Dr, Denton

Listing courtesy of Eastern Shore Real Estate, LLC. Contact:

216 S 3rd St, Denton
$250,000
3 Beds ⋅ 2 Baths
Why rent when you can own and start building equity and an asset of your own? Priced at just $250,000, this charming home in the heart of downtown Denton offers an affordable opportunity to put your personal touches into a home and make it your own. The main level features a spacious living room with updated flooring, kitchen with separate dining area, office/flex space, mudroom, and a full bathroom, while upstairs you'll find three bedrooms and another full bathroom. An unfinished basement provides additional storage space & laundry and the inviting front porch with swing is the perfect spot to relax and enjoy the charm of this walkable downtown location. Conveniently located near the Choptank River, shops, dining, and everything downtown Denton has to offer. This home offers plenty of space, character, and potential for someone looking for an opportunity to own rather than rent. Seller will need a short 1 week rent back & subject to finding a home of choice. Don't delay and schedule your showing on this adorable bungalow today!

216 S 3rd St, Denton

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

105 S 5th Ave, Denton
$290,000
4 Beds ⋅ 2 Baths
Step into a charming piece of history with this beautiful Colonial home in the desirable Denton area. Built in 1900, this 2,759-square-foot residence offers the character and craftsmanship of a bygone era while providing the space and conveniences today's buyers desire. From the moment you arrive, the large wrap-around front porch with beautiful wood decking welcomes you home. It's the perfect spot to enjoy your morning coffee, relax on a summer evening, or simply take in the charm of small-town living. And with local festivals, parades, and community events passing right by your front porch, you'll have a front-row seat to all that makes Denton special! Inside, you'll find four spacious bedrooms and two full bathrooms, along with generously sized living areas featuring a mix of hardwood and carpet flooring. The large dining room provides plenty of space for holiday gatherings and entertaining, while a separate office offers the perfect setting for working from home, hobbies, or a quiet study. The well-appointed kitchen features a built-in range, cooktop, dishwasher, and disposal, making everyday cooking and entertaining a pleasure. A cozy fireplace adds warmth and character to the home, creating an inviting place to gather on chilly evenings. Step outside and discover the property's unique carriage house, offering additional storage, workshop space, or the opportunity for a creative project. The approximately 0.19-acre lot also provides an asphalt driveway with ample parking. If you've been dreaming of a home filled with character, space, and front-porch charm, this Denton Colonial deserves a closer look. Enjoy the history, embrace the community, and experience the best of small-town living—all from your own front porch!

105 S 5th Ave, Denton

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

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