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Eastern Shore Homes with a Guest House

View listings for homes with a guest house on the Eastern Shore of Maryland. 

Eastern Shore Homes for Sale with a Guest House

Call Chuck Mangold at 410-924-8832 with any questions or to see any of these properties in person.

12512 Fleetway Dr Ocean City MD 21842

Ocean City, MD12512 Fleetway Dr

Price$420,700

Est. Mortgage: $/month

Pending

MLS Number MDWO122364

  • Single Family
  • Address 12512 Fleetway Dr
  • Bathroom 3
  • Bedrooms 5
  • Square Feet 1992

TWO HOUSES FOR THE PRICE OF ONE! This well maintained West Ocean City property has a 24' X 60' rancher and a 24' X 34' two bedroom cottage that would be perfect as a guest house or income producing rental. The 3 bedroom, 2 bath main home boasts an open floor plan with an abundance of upgrades including engineered hardwood floors, granite countertops, custom tile work and custom paint, new lighting fixtures, office/den, new windows, new HVAC, encapsulated crawlspace, an oversized front porch, screened in patio, manicured landscaping and much more. Located on a 1/2 acre, one will be sure to enjoy the tranquility of the maple shade trees and spacious fenced in back yard. An additional 12x16 storage shed has work benches and electric. These homes are convenient to the areas public marinas, Assateague Seashore, shopping centers, and schools. NO HOA fees or city taxes. This property is a must see!

Listed by Barbara Busch of Resort Real Estate Inc

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$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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401 Kidwell Ave Centreville MD 21617

Centreville, MD401 Kidwell Ave

Price$485,000

Est. Mortgage: $/month

Open House

MLS Number MDQA147586

  • Single Family
  • Next Open House: Sun 05/16 11:00 am. to 1:00 pm.
  • Address 401 Kidwell Ave
  • Bathroom 4
  • Bedrooms 5

Welcome Home! This Unique Move-In READY HOME, has everything you could want and more!(UPDATED PICTURES MAY 6th) 5 bedrooms and 4 full baths, home office, wood burning fireplace, inground pool, any many updates. Main house has New Metal Roof 2016, New Heat Pump 2016, New Siding 2016, New Appliances 2016, New Kitchen and Baths 2016, New Windows in 3 Season Room 2018 overlooking back yard and pool. Guest House with separate utilities has New Roof 2021, New Siding 2021, New Windows 2021 and ready for your vision! The property located in the town of Centreville, walking distance to all the town restaurants, shops, schools, and parks. Property includes a Main House with In-ground pool and Guest House with full bath and kitchenette. The guest house offers endless possibilities with separate utilities and driveway, can be used as an In-Law Suite/Home Gym/Pool House/Home Office/Small Business/Efficiency Rental. This home is located on .85 acres. There is NOTHING like this on the market!!!

Listed by Lisa A. Knotts of Chesapeake Real Estate Associates, LLC

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$
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$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5018-5020 David Greene Rd Cambridge MD 21613
Pending

MLS Number MDDO126994

  • Single Family
  • LocationType River
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2053

Westerly Sunset and broad water views enjoyed daily from this very special property with 4' MLW. A quick boat ride and you'll be in the Chesapeake Bay with easy access to some of the best fishing spots in the Mid Bay region. You'll catch everything from Striped Bass, Flounder, Cobia, Trout, Croaker and more. Quieter waters of Fishing Creek & Church Creek are terrific water sports areas for water skiing & wakeboarding or to launch your trot line to catch the 1st crabs of the season. Oversized T-shaped pier with water & electric offers a minimum of 6 slips which is ideal for multiple boats or visiting guests. Launch your small boat, jet ski, kayak, canoe or paddle board from the boat ramp and then put your chair in the sand and relax on the SANDY BEACH. Also included is a separate buildable lot with BAT septic installed for 3BR house - yes you can build a 2nd dwelling, guest house, main house or whatever you desire. Extremely well maintained open floor plan home offers Cathedral Ceiling Great Room concept and split floor plan with Water View 1st Floor Owner's Suite & direct access to screened porch plus walk-in closet, jetted tub, dual sink vanities, and walk-in shower. Oversized 2 car attached garage, oversized detached garage plus separate 1 car garage. Plenty of room for car storage, boat storage, hobbies & workshop space. Enjoy the best of Eastern Shore Living!

Listed by Sharon Spedden of Sharon Real Estate P.C.

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$
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$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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32123 Clarks Wharf Rd Trappe MD 21673

Trappe, MD32123 Clarks Wharf Rd

Price$3,950,000

Est. Mortgage: $/month

MLS Number MDTA138290

  • Single Family
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 8600
  • Year Built 1995

Mallard Point Farm , 255+/- acres. Includes Tax ID 03153223. Main house boasts 8,600 sq ft of living space on one level, 3 Bedrooms with en-suite baths. 10' ceilings through out, hardwood floors, solid construction. Gourmet kitchen features Wolf stainless steel commercial stove w/hood, Kitchen Aid appliances include double wall ovens, dishwasher, refrigerator, Island with granite counter tops, walk-in pantry, recessed lighting and water views. Family room, living room, master bedroom, and Florida room all have french doors that lead to the waterside deck. 3 car attached garage, multiple outbuildings, and pier. Guest house, 4 bedrooms, 3 baths, Living room with wood burning fireplace, dining area, and large kitchen with screened porch. Great Hunting & Fishing!

Listed by Clifford E Meredith of Meredith Fine Properties

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$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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31539 Bruceville Rd Trappe MD 21673

Trappe, MD31539 Bruceville Rd

Price$250,000

Est. Mortgage: $/month

MLS Number MDTA140416

  • Single Family
  • Address 31539 Bruceville Rd
  • Bathroom 2
  • Bedrooms 2
  • Square Feet 1280

Cozy farmhouse featuring 2 bedrooms and 2 full bathrooms. Natural stone floors throughout the first floor. Big garage, screened gazebo, big shed. The property also includes an extra building that can be used as a summer guest house or storage. Big back yard.

Listed by Nataliya Moskalyuk of Coldwell Banker Chesapeake Real Estate Company

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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25511 Bruffs Island Rd Easton MD 21601

Easton, MD25511 Bruffs Island Rd

Price$7,900,000

Est. Mortgage: $/month

Pending

MLS Number 1003265299

  • Single Family
  • LocationType River
  • Bathroom 6
  • Bedrooms 3
  • Square Feet 8971

5 separate parcels.16 feet water depth at boat house. Sandy beaches. Magnificent specimen trees. Broad views in every direction with sunsets and sunrises. 2 acre pond. Two guest houses. Pool. Pool house. Tennis court. Multiple barns and outbuildings. Very high elevation. By appointment only.

Listed by Clifford E Meredith of Meredith Fine Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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11165 Shaw Bay Lane Easton MD 21601

Easton, MD11165 Shaw Bay Lane

Price$7,900,000

Est. Mortgage: $/month

Pending

MLS Number MDTA138046

  • Single Family
  • Address 11165 Shaw Bay Lane
  • Bathroom 6
  • Bedrooms 3
  • Square Feet 8971

SHOWN BY APPOINTMENT ONLY. 5 separate parcels. 16 feet water depth at boat house. Sandy beaches. Magnificent specimen trees. Broad views in every direction with sunsets and sunrises. 2-acre tidal pond. Two guest houses. Pool. Pool house. Tennis court. Multiple barns and outbuildings. Very high elevation.

Listed by Clifford E Meredith of Meredith Fine Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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22020 Benders Ln Sherwood MD 21665

Sherwood, MD22020 Benders Ln

Price$5,350,000

Est. Mortgage: $/month

MLS Number MDTA135344

  • Single Family
  • LocationType River
  • Address 22020 Benders Ln
  • Bathroom 6
  • Bedrooms 4

Harris Creek Farm - 128 acres with development potential, improved by a 10,525 sq' residence with full basement, three bedroom guest house, stable, paddocks, sheds, ponds, pier with six+ feet of water at mean low tide, mature woods and open fields, including a 1,920 ft turf airstrip registered with the FAA. The shoreline is protected and the elevations surrounding this home are above the 500-year flood plain. Broad, very broad views over Harris Creek and down the Choptank River. The farm has numerous sites to accommodate additional homes if subdivision or estate planning is in order and there is abundance of wildlife and waterfowl. The house provides a number of living spaces with a great room/kitchen and casual living space to accommodate large gatherings or quiet retreats. Additional family rooms, media rooms, recreation rooms and whole house basement offering an abundance of storage and easy access to mechanical equipment. First-floor guest suite, second floor master with three additional guest rooms with baths en-suite. Designed by the late architect, Alan Meyers, Bald Eagle Point captures the scenic vistas across Harris Creek providing a view of all the Chesapeake has to offer. Located between St. Michaels and Tilghman, Bald Eagle Point is a unique opportunity to own Talbot County Waterfront with division potential and/or conservation measures. Please contact listing agent for additional information or scheduling.

Listed by Coard A Benson and Alicia G Dulin of Benson & Mangold, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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6243 Boston Cliff Rd Easton MD 21601

Easton, MD6243 Boston Cliff Rd

Price$2,995,000

Est. Mortgage: $/month

MLS Number MDTA136806

  • Single Family
  • LocationType Rural
  • Address 6243 Boston Cliff Rd
  • Bathroom 4
  • Bedrooms 3

PLEASE VIEW AERIAL AND INTERIOR TOURS BY CLICKING THE MOVIE CAMERA ICON "VIRTUAL TOURS". "Boston Cliff", patented 1665. Phase one built ca. 1676; phase 2 in 1729; and phase 3 in 1954. Historically and architecturally one of the most important houses in the Chesapeake region. Georgian raised paneling, built-in cupboards, staircase with carved tulip step-ends, mantels with bolection moldings, 5 fireplaces, raised panel doors with original hinges, and paneled window seats. Gunstock cornerposts. Outbuildings including guest house designed by Dr. H. Chandlee Forman. A.I.A. Paddock, horse stalls, tack room. English garden. Large fenced dog yard. Pool. Bailey pier with 10 ft MLW. Minutes from Easton with its hospital, restaurants, museums, galleries; and from the famous sailing seaport Oxford. Current owner rebuilt the swimming pool. installed boat lift on the dock; re-roofed some of the cedar shingle roofs; converted from oil heat to LP Gas; refinished floors; painted interior in early original colors as determined by paint historican Susan Buck; opened the fireplace in the LR; and renovated the guest house. House written up in several books and has been on the Maryland House and Garden Pilgrimage. One of Maryland's few houses with a legitimate claim to 17th Century origin. Family room can also be used as a first story Master Bedroom with private bath.

Listed by Robert G Shannahan of Shoreline Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5733 Pecks Point Rd Easton MD 21601

Easton, MD5733 Pecks Point Rd

Price$7,995,000

Est. Mortgage: $/month

MLS Number MDTA140612

  • Single Family
  • LocationType Rural
  • Address 5733 Pecks Point Rd
  • Bathroom 9
  • Bedrooms 7

One of the most iconic properties in Talbot County on Maryland's Eastern Shore; Tred Avon Manor sits prominently on a 16+ acre south facing peninsula on the Tred Avon River, just across from Oxford, Md. The property has over 1,200 feet of rip-rapped and preserved shoreline and a deep water pier with boat lift, electric and fresh water. The historic Manor House has been completely restored and updated with impeccable attention to every detail. The main residence has over 9,000 sf of living space comprising 7 bedrooms, 6 full and 2 half baths. Grand entertaining spaces include a reception hall with fireplace, expansive dining rooms, library with fireplace and sizeable living room with fireplace, 15 foot ceilings, custom cabinetry and bookshelves, large wet bar, and walls of windows to admire the sweeping views of lawns and river. There is a large modern chef's kitchen with family room area and adjoining laundry, mud room and flower room. The Second floor has 4 Bedrooms, all en suite, and an Owner's Suite with large scale Bath and a separate Gym/Office with an attached half Bath. In addition, the home has a 3rd floor with two Bedrooms with Jack and Jill bath, and a separate apartment with full kitchen and Living Room and its' own Bedroom. The separate 2 BR, 2BA guest House has a huge Living Room with cathedral ceilings and wide outdoor porches. There is a 3 car detached garage with ample storage loft space above. The grounds are a gardener's paradise with a gunite swimming pool, rose covered pool house with changing rooms and a bar, and impeccable gardens including raised irrigated beds. This property offers absolutely everything that could be asked for in an Eastern Shore estate, including a sunken heated goose/duck blind. Don't miss this once in a lifetime opportunity.

Listed by Frederick E Hoffman of TTR Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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28589 Brick Row Dr Oxford MD 21654

Oxford, MD28589 Brick Row Dr

Price$5,850,000

Est. Mortgage: $/month

MLS Number MDTA140774

  • Single Family
  • LocationType Creek/Stream
  • Address 28589 Brick Row Dr
  • Bathroom 6
  • Bedrooms 4

Red Oak Point Farm - Pristine Eastern Shore estate farm offering seclusion and privacy in a sportsman's paradise!160 +/- acres with 3,000' of shoreline, western exposure and panoramic views on Island Creek. The main parcel consists of 100 acres with gated entry featuring a 7500 +sf gracious Low Country Southern Cape Cod main house- defining understated elegance. 4 + bedrooms, 5 + bath with spacious open kitchen with soapstone counters, large bar and breakfast nook with fabulous walk in butlers pantry. Great room with beamed cathedral ceiling, fireplace. 2 story brick wall & french doors opening to pool and water. Den with fireplace and built-ins, large formal dining room with built-ins and home office with porch access. First and second floor primary bedroom suites, with custom baths, spa showers and walk-in closets. Second floor primary has a fireplace, deck overlooking water and waterside exercise room. Wide plank wood flooring and exceptional fit & finishes throughout. Tons of storage including 3000 + sf of basement and 2000 sf of attic space. Outdoor features fabulous screened porch, brick deck and patio, waterfront oversized gunite pool with hot tub(s) pool house with kitchen and full bath. 10k and 15k boat lifts, boat ramp and pier on Island Creek. 3 car garage with carport and additional storage. Additional residences on property include the Farm House, 3 Bedroom 2 Bath colonial guest house, with first floor primary suite, family room with fireplace and porch. The Stable House consists of 2 Bedroom 1 1/2 bath with hardwood floors throughout and custom cabinetry and breezeway to stables with tack room half bath and kitchenette overlooking 5 acres pond and pastures. Multiple outbuildings include 50 x 100 pole building with lean to and stables, 40 x 80 pole barn with attached conditioned workshop, 30 x 40 barn/shop. additional 3 car garage with shop. Stable barn with 4 stalls, heated tack room, kitchen, bath, run in shed, main shop- gathering barn with conditioned work space and club room. 3 ponds on property including 5 acre pond with wells and 2 fountains. 100 Acres of fenced pasture with feed shed make this ideal for horses! Fabulous hunting, waterfowl, deer and turkey. Additional parcel is 60 + acres with 40 acres in mature woods, open space and 10 acres in til.

Listed by Katherine M Christensen of Benson & Mangold, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5780 Shipyard Point Rd Royal Oak MD 21662

Royal Oak, MD5780 Shipyard Point Rd

Price$3,500,000

Est. Mortgage: $/month

Pending

MLS Number MDTA135338

  • Single Family
  • LocationType Bayfront
  • Bathroom 8
  • Bedrooms 5
  • Square Feet 9740

The gorgeous, private 9740+ square feet colonial nested on 22+ acre waterfront estate offering 6+ feet of water on Haskins Cove/Irish Creek. The 4100'+/- of shoreline allows water view from most all rooms. The main house offers 4 bedroom suites plus large, maids quarters which has its own entrance over one of the garages. You will enjoy the large great room with two fireplaces and the library with 9 foot+ ceilings is you own little getaway. The kitchen offers top of the line appliances with huge granite island, (new refrigerator 2018 sub-zero). Casual entertaining in the media room. Formal dining room offers elegant in style. Two attached garages. The 3 bedroom, 2 bath waterfront guest house allows privacy for your guest, they can enjoy your waterfront. Two extra-large barns with offices & wash stations, fully fenced for your horses. Get your exercise on the fully fenced Tennis Courts, then a swim in the diving pool and enjoy your special refreshing drink at the pool house. If you are still ready for more fun, power up you boat at the dock, which has 6+/- feet water depth at MLW, and sail the waters of Irish Creek and Haskins cove. For the nature lovers, you have your pond with all types of wild life. This estate meets most all lifestyles giving you privacy and seclusion yet only 10 minutes to Easton or ST Michael that offers the arts, shopping, and restaurants of all flavors. This home is considered be one of the finest estates in Talbot County, due to the waterfront and location The exterior is brick with sprawling lawn and mature plantings. The interior offers chair railing, crown molding and lovely stairway when entering the large open foyer. The kitchen offers a view of the waterfront (as do all rooms) the current owner has owned the property since 1993.

Listed by Glory Bee B Costa of Keller Williams Select Realtors

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Copyright 2021 BRIGHT, All Rights Reserved.  Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Chuck Mangold participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.Data last updated May 13, 2021. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.

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