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Explore Our Properties
HELP YOU FIND YOUR DREAM HOME!

HELP YOU FIND YOUR DREAM HOME!

DISCOVERING WHERE YOU BELONG - LET US HELP YOU FIND YOUR DREAM HOME!

 

Offices in Queen Anne's, Talbot and Kent Counties

FEATURED LISTINGS

 
 

Finley Creek Drive

(Lot 6)

Centreville, MD 21617

 

$975,000

 

Finley Creek Estates, an exclusive new community nestled in between Centreville and historic Chestertown situated on 1 plus acre lots. This luxurious estate like home is to be built by Red Oak Properties. Featuring 3100 +/- square foot home.

 

 

Eagle Manor Drive

(Lot 20)

Church Hill, MD 21623

 

$940,000

 

Be one of the first to occupy the beautiful Mossy Oak Model home completed by Red Oak Properties, with all the bells and whistles. This 3100 +/- square foot home features, a home office on the first floor, gourmet kitchen with Island, wall oven, gas cook top, wine cooler, beverage cooler and gas fireplace sitting area.

 
 

435 Eagle Manor Drive (Lot 10)

Centreville, MD 21617

 

$740,000

 

Offers a nice open and entertaining floor plan with one level living, along with a finished room upstairs that could be a home office, rec room, play room etc. Red Oak is a custom builder and a buyer can work off of their existing popular plans or can design one for the buyer.

 

 

441 Eagle Manor Drive

Church Hill, MD 21623

 

$685,000

 

House in picture is to be built. This floor plan is a 3-bedroom  2.5 bath layout. Finished bonus room upstairs would make great home office or craft room. Unfinished basement for even more space. Upstairs has a separate laundry room with cabinets and countertop.

 
 

334 Eagle Manor Drive (Lot 22)

Church Hill, MD 21623

 

$614,700

 

To be built in the community of Condor Manor in Church Hill! This is Red Oak's most popular model with various options available . This Pin Oak model, built by Red Oak Properties, LLC is a must see home featuring LVP flooring all throughout the home, upgraded kitchen oversized Island, perfect for preparing meals or entertaining. Entertaining can continue outside to the maintenance free deck.

 

 

 

23678 Willow Pond Road

Denton, MD 21629

 

$525,000

 

This property rests on 5 acres, including much open field ready for horses, goats, chickens, or plenty of space for large gardens or more. Home offers updates throughout including new roof, also has been freshly painted, and new LVP flooring throughout, new Mini split on 2nd floor. updated bathrooms and all new appliances.

 

 
 

103 Liam Thomas Ln

Stevensville, MD 21666

 

$498,995

 

BRING ALL OFFERS ! 

Don't miss the opportunity to see this practically new Ellendale end unit. Built in 2018, this beautiful unit offers tons of living space and is ready for its new owners. Upon entering on lower level you are greeted by an open area that offers wood floors, powder room, large closet and access to the 2 car garage.

 

 

 

116 Kent Point Road

Stevensville, MD 21666

 

$475,000

 

Back on the market with a new roof! This Kent Island home is back to active due to the previous buyers’ circumstances changing. move-in ready home featuring thoughtful updates, including a brand new roof, new well pump, HVAC system, stove, and refrigerator. For added peace of mind, a one-year home warranty is included.

 

 

 

 
 

 

OPEN HOUSE: 9/28/2025 1:00 PM - 3:00 PM

29865 Hillary Avenue

Easton, MD 21601

 

$470,000.00

 

Welcome to easy Eastern Shore living in the sought-after 55+ age restricted community of Easton Club East! This pet and smoke-free home has been lovingly maintained and thoughtfully updated, offering comfortable one-level living with style and ease.

 

 

 

 

209 Kesley Court

Queen Anne, MD 21657

 

$424,900

 

a beautifully maintained ranch-style home nestled on a quiet cul-de-sac in the sought-after community of Deans Meadows. Located just minutes from Centreville, this property offers the perfect blend of privacy, comfort, and convenience.

 

 
 

321 Front Street

Crumpton, MD 21628

 

$420,000

 

Step inside to discover a well-maintained interior with a unique artistic flair. The cozy gas fireplace adds elegance and warmth to the living space, while the kitchen is fully equipped with stainless steel appliances, perfect for any home chef. A desirable first-floor primary bedroom and en suite bath offer comfort and convenience, along with a half bath for guests. Upstairs, two spacious bedrooms share a large full bath.

 

112 W Main Street

Sudlersville, MD 21668

 

$410,000

 

HOUSE TO BE BUILT!!! Pictures show what finished house will look like. Construction to start 7/1/2025. 3-bedroom 2 bath rancher. This one will be loaded with all kinds of goodies. Upgraded trim package, upgraded lighting. Flooring and kitchen cabinets are top of the line. Wait till you see the tiled shower with dual shower heads. 

 

 
 

1010 S 2nd Street

Denton, MD 21629

 

$365,900

 

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.

 

 

109 Wilton Road

Chestertown, MD 21620

 

$349,900

 

The home boasts a large primary bedroom with its own private bath and an impressive walk-in closet, which includes a cedar section for added storage and warmth. The kitchen and dining area, featuring newer flooring (installed just two years ago), create a modern, inviting space for meals and family gatherings. The kitchen is equipped with updated appliances, ensuring a functional and stylish area for cooking.

 

 
 

135 Kerney Street

Federalsburg, MD 21632

 

$336,500

 

This home boasts upgrades throughout. The kitchen features Granite countertops, stainless steel appliances large island, and a spacious pantry. Large dining room or convert to another living area. Well-appointed bedrooms and a primary with ex large walk-in closet and bathroom.

 

 

 

OPEN HOUSE: 9/28/25 11:00 AM - 2:00 PM

 

228 Phelps Avenue

Galena, MD 21635

 

$329,000

 

Nestled on a spacious corner lot in the heart of Galena, this historic American Four Square blends timeless character with modern updates. Known for its barn-style outbuildings--perfect for storage, workshop space, or future restoration--this property offers both charm and functionality.

 
 

305 Appley School Road

Cambridge, MD 21613

 

$285,000

 

You don't need to wait for new construction, when this home is MOVE IN READY & UPDATED!! And almost DOUBLE the SQUARE FEET of the new builds in this community!! So much more space for an amazing price!!!! Do yourself a favor and schedule a tour to see it first hand!

 

 

 

21245 Tanyard Road

Preston, MD 21655

 

$275,000

 

A spacious rancher with 3 bedrooms and 2 full baths nestled on a peaceful 0.62-acre lot in Preston. Built in 1987, this single-level home offers a solid foundation and a functional layout, ready for your personal touch and updates.

Are you ready to embark on an exciting journey in the world of real estate? At Chesapeake Real Estate Associates, we invite you to discover your true passion and unlock a realm of endless possibilities for success. Our unique agent-owned model fosters a supportive and collaborative environment, where new agents can thrive alongside experienced mentors. Join our friendly, community-oriented team and experience the difference of personalized service that prioritizes trust and client satisfaction. Together, let's explore the dynamic real estate market on Maryland's Eastern Shore and turn your aspirations into achievements. Team up with us and take the first step towards a fulfilling career in real estate!

 

 

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We live in a beautiful area on the Eastern Shore of Maryland, and we want you to experience that lifestyle as well. Call us today and we can get you started.

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