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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. You may also be interested in browsing all Eastern Shore homes.

7927 Maiden Point Ct Easton MD 21601

Easton, MD7927 Maiden Point Ct

Price$2,250,000

Est. Mortgage: $/month

Open House

MLS Number MDTA141278

  • Single Family
  • Next Open House: Sat 10/23 11:00 am. to 1:00 pm.
  • LocationType River
  • Address 7927 Maiden Point Ct
  • Bedrooms 5

One of Easton Village's Crown Jewels! Enjoy the sun rise over the Tred Avon River from this Custom built Farmhouse Style ILEX built home. The most Spectacular Water Views in Easton Village. This luxurious home calls to the most sophisticated buyer, with hardwood floors throughout, marble bathrooms, granite countertops, custom cabinetry, coffered ceilings, elevator, 3 wood burning fireplaces, screened porch, wrap around porches, air soaking tub, custom showers, commercial grade appliances, lighted wet bar with wine cooler, and room for a pool, guest house with 1 br, 1 ba, kitchenette, 1 deeded deep water boat slip, and 2 car oversized garage. This cul de sac lot is the most secluded lot in Easton Village, with a preserved wood waterfront lot next door. An amazing location to restaurants, shopping and hospitals. This home is one of a kind and won't last in the fast moving market. Make an appointment today to preview this amazing property.

Listed by Clifford E Meredith of Meredith Fine Properties

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$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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10565 Sherwood Manor Dr Claiborne MD 21624

Claiborne, MD10565 Sherwood Manor Dr

Price$3,998,000

Est. Mortgage: $/month

MLS Number MDTA2001036

  • Single Family
  • LocationType River
  • Bathroom 5
  • Bedrooms 4
  • Year Built 1970

*NOTE: Use directions provided in listing GPS inaccurate* Just five miles from St. Michaels travel past some of the most bucolic waterfront farms and properties in Talbot County to the end of Sherwood Manor Drive where you will find a peninsula surrounded by the deep, protected waters of Tilghman Creek off the Miles River. Located here are the two waterfront parcels offered in this new listing: Parcel 21, “Eagles Nest”, improved by a gorgeous 5500+ fsf four bedroom Colonial and adjacent unimproved waterfront Parcel 20 complete with a newly established 6 bedroom Septic Reserve Area. With Tilghman Creek on two sides Parcel 21 at 10565 Sherwood Manor Drive is improved by a very high quality two story residence built in 1970 and since expanded and updated. The property enjoys a 6 foot wide private pier on the protected side of Tilghman Creek (sailboat heaven!) with a massive main slip, additional slip with lift and 7-8ft mlw (to be confirmed by buyer). From the other side of the peninsula this property enjoys fantastic broad views of the Creek and out to the Miles River and Eastern Bay. This home features 4 bedrooms and 4.5 baths including an expansive first floor primary bedroom wing that includes a 26 x 17 bedroom, multiple large closets, a 13 x 12 full bath, separate den with built-ins and a laundry. In addition to the primary bedroom wing the first floor also includes a spacious formal living room with fireplace and built-ins, private office with built-ins, 37 x 22 Great room with two massive fireplaces at each end, formal dining room, gorgeous solarium, and a spacious kitchen with premium cabinetry, counter tops and appliances. On the second floor you will find a guest suite with bedroom, sitting room, bath and waterfront balcony plus two additional bedrooms and two baths and large 10 x 5 cedar closet. This home has a variety of ceiling heights, hardwood floors, custom moldings and built-ins, solid interior doors, excellent quality windows and abundant French doors that access multiple outdoor patios. There is an iron gated entrance anchored by brick pillars, impressive wide brick circular drive and parking areas, 3 bay garage with workshop space and staired storage above. Included are top of the line hvac units, including two Buderas gas furnaces, a whole house Generac generator, security system, and full yard/bed irrigation. Adjacent unimproved Parcel 20 enjoys Tilghman Creek on two sides as well. With the completion of a lot line revision currently underway Parcel 20 will be 10.22 acres, have an established 6 br Septic Reserve Area and potentially 3-4 ft mlw +/- on protected side and 3 ft mlw +/- on the broad view/riprapped side of Tilghman Creek (to be confirmed by buyer). The lot line revision in process will increase improved parcel 21 to 5.88 acres (adding 3 acres to increase impervious allowance for the addition of a potential addition, pool, guest house, etc.) and reduce unimproved parcel 20 to 10.267 acres with no ill effect. The draft plat is included in the document tab. Both parcels enjoy excellent X flood elevation. Parcel 20 and 21 are in two separate trusts and require two separate contracts with disclosures provided.

Listed by Janet R Larson of Benson & Mangold,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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5708 Adams Rd Federalsburg MD 21632

Federalsburg, MD5708 Adams Rd

Price$279,000

Est. Mortgage: $/month

MLS Number MDDO126774

  • Single Family
  • Address 5708 Adams Rd
  • Bedrooms 2
  • Year Built 1974
  • Bathroom 2

Country rancher, close to town. Remoldeled 2013 HW floors, open floor plan, large rooms, large closets, Custom built brick Rancher, close to Federalsburg an Seaford. Two to three berooms, open floor plan, private separte guest house refinised 2014. Gas fireplace and stream in rear of property

Listed by Barbara G Nichols of Results Realty Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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5748 Hopkins Neck Rd Easton MD 21601

Easton, MD5748 Hopkins Neck Rd

Price$4,995,000

Est. Mortgage: $/month

MLS Number MDTA2000588

  • Single Family
  • Address 5748 Hopkins Neck Rd
  • Bedrooms 5
  • Square Feet 6815
  • Year Built 1994

Wind Song is conveniently located between Easton and St. Michaels and enjoys some of the most spectacular water views in Talbot County with 7 Miles of Southwest exposure on the Tred Avon River looking past the Town of Oxford and all the way to Todd's Point in Dorchester County. It has the rare and desirable combination of very deep water 5' MLW, protection from winter storms and the perfect exposure to catch the summer's prevailing breezes. These features along with the large mature trees which bathe the home in shade provide a rarely replicated combination. The home is a lovely brick French Country style with first floor primary bedroom, a total of five bedrooms including a one bedroom apartment, open floor plan, gourmet kitchen, pool house, tennis court, attached and detached garages, 3 fireplaces, guest house and waterside pool at the 50' buffer.

Listed by Schuyler G Benson of Benson & Mangold,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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10468 Golf Course Rd Ocean City MD 21842

Ocean City, MD10468 Golf Course Rd

Price$4,299,000

Est. Mortgage: $/month

MLS Number MDWO2000211

  • Single Family
  • LocationType Bayfront
  • Address 10468 Golf Course Rd
  • Bathroom 5
  • Square Feet 4310

The property you have been waiting for is now on the market and available for purchase! Located on the Thorofare/Assawoman Bay in the lovely community of Captain's Hill in West Ocean City, this home resides on over an acre of land with the most gorgeous views of the bay and the OC skyline. The house and Guest house offer 270Â water views from every window. Watch the beautiful sunrises and sunsets from the large decks, one of which completely wraps around the entire second floor. There are a total of five Bedrooms, four Baths and 2 Half Baths; Great Room with a wood burning fireplace; formal Dining Room with a pretty tray ceiling and French doors; Family Room with a gas fireplace and an additional deck that offers the best view in the house; a Gym; gourmet Kitchen with top of the line appliances; large Pantry; Laundry Room; and hurricane shutters. Additionally, the finishes include granite counters and vanity tops, bamboo and marble flooring, crown moulding, chair rail, 9 ft ceilings, Lutron lighting, an elevator with a cherry, raised panel interior, sprinkler system, and over-sized windows and sliders. Ocean City Proper is just minutes away by boat, bike or car. Twenty minutes away is the world famous Assateague Island, home to the spectacular wild ponies, which have roamed freely for over 400 years. There are world class marinas nearby, as well as fabulous restaurants, shopping, doctor's offices, schools, etc. There is an abundance of incredible waterfowl, including Great Blue Herons, Snowy Egrets, ducks, geese, and regularly seen pods of Seals racing through the Thorofare that add to the enjoyment and peaceful tranquility this property offers. Chart your own course...set your own sails...relax and enjoy one of Ocean City's premier properties!

Listed by Katherine G. Wright Payne of Coastal Life Realty Group

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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7950 Bloomfield Rd Easton MD 21601

Easton, MD7950 Bloomfield Rd

Price$3,250,000

Est. Mortgage: $/month

Pending

MLS Number MDTA2000930

  • Single Family
  • Address 7950 Bloomfield Rd
  • Bathroom 5
  • Year Built 1958
  • Bedrooms 5

'Gratitude' truly represents the best of the Eastern Shore. Sited on 3.76 private acres and located just minutes from Easton and St Michaels (Oxford by boat), this special property features a beautiful main home, gorgeous boat house, and quaint separate guest house. The owners have lovingly cared for and renovated almost all of the property which is evident from the moment you turn into the welcoming drive. The brick 5 bedroom/4.5 bathroom house is filled with light and offers water views from nearly every room. A gracious foyer leads to the living room, dining room, and den which all have fireplaces and exude charm. The waterside sunroom is everyone's favorite as it has high ceilings, multiple french doors, and takes in Shipshead Creek's quiet and stunning scenery. In 2009, the kitchen was renovated and added to with walls of windows, and features Viking appliances, a six burner gas range, granite countertops, double sinks, 2 dishwashers, bar area, and island with bar stools. A wonderful breakfast area and vaulted ceiling family room (with fireplace) are adjacent and add to the great design and flow. A large first floor bedroom and bath have it's own wing and separate outside entrance, making it ideal for guests/family. On the second floor, the primary bedroom has a fireplace and lovely balcony overlooking the garden courtyard. The bath was completely remodeled in 2011 with a large steam shower, double sinks, marbled floor with radiant heat, and a large custom built-in closet. Two additional waterside bedrooms (one with fireplace) and full bath are down the hall. On the third floor is another bedroom, sitting room, and renovated bathroom. On the lower level is a wine cellar with small tasting area, and dumbwaiter up to the dining room plus storage and cellar outside of the entrance. The coveted boathouse is good sized and ample for most boats while the pier offers 3 large slips and has 4'MLW (buyer to verify). The setting is one that is simply magical! A 1 bedroom/bath guest cottage (referred to as the 'Retreat' by the owners) was renovated in 2015 and includes a living room, bar kitchen, wood stove, and deck. Behind the cottage is the 'Barn' with boat storage and a 3 car adjacent garage with workshop. Extensive hardscaping and landscaping are evident throughout the property and include full irrigation and beautiful exterior lighting. There is ample room for a pool on the side which would have water views and the seller will consider selling furnishings.

Listed by Laura H Carney of TTR Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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101 Strand Oxford MD 21654

Oxford, MD101 Strand

Price$1,795,000

Est. Mortgage: $/month

MLS Number MDTA2000740

  • Single Family
  • Address 101 Strand
  • Bathroom 4
  • Year Built 1920
  • Bedrooms 4

C1880, this home has been meticulously and lovingly restored to combine the finest antique materials with the best available green features by the owners, Barbara Paca, Landscape Architect and her husband Philip Logan, the architect for the project in 2006. Together they transformed an Oxford Victorian into a masterpiece of light and amazing spaces. This 4 bedroom home must be seen to be appreciated. The 2 story contemporary guest house and the swimming pool with its marble deck, all compliment the old house. Geothermal, wheelchair accessible, German solar panels, Buderus and Rinnai continuous hot water systems, three floor elevator, all hardwood floors, radiant heated floors in the primary bath and the marble floored studio, are just a few of its many features. 2 story guest house with 1 1/2 bath, wood burning tile stove, kitchen, large bedroom.

Listed by Jane M McCarthy of Benson & Mangold,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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$2,795,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDTA136806

  • Single Family
  • LocationType Rural
  • Address 6243 Boston Cliff Rd
  • Square Feet 2699
  • Bathroom 4

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: 3.05% last updated on Oct 14, 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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736 Honeysuckle Trl Crownsville MD 21032

Crownsville, MD736 Honeysuckle Trl

Price$750,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDAA2003554

  • Single Family
  • LocationType River
  • Address 736 Honeysuckle Trl
  • Year Built 1934
  • Square Feet 1728

Get two homes for the price of one. Two separate parcels for .34 acres of waterfront! Priced for both separately deeded properties: 734 and 736 Honeysuckle Trail. Tear down, renovate, use for AirBnB or a weekend getaway. Two level bungalow and the in-law cottage are on the Valentine Creek of the Severn River. The two-level 1934 bungalow home at 736 sits on a gentle sloping hill to the sandy beach of a private deep water pier, deeded. The bungalow is a throwback to days-gone-by when Herald Harbor was a vacation getaway for the city folks and homes were just for sleeping because the outdoors was where it was at! This home has beautiful original rustic hardwood flooring on the entry level with a wood-burning fireplace. This is not fancy but everything is functional and you can live on the upper level in general comfort--HVAC keeps the home comfortable with central heating and air conditioning and energy-efficient replacement windows do their job. The waterside all-seasons room is a perfect hang-out year round and the rear deck is great for lounging or eating al-fresco waterside. The top level has a dressing room/bedroom with an antique armoire for your wardrobe and a larger room for the main bedroom. The lower level needs finishing and work: bedrooms are framed out. There is a full bath, open living area and a laundry room with washer/dryer. The lower level is a completely separate unit that is not accessible from the top floor so you have two distinctly different living spaces -- live in one and rent the other out! Or do a complete renovation to bring both levels together or do a tear down for a custom re-build. Need a mother-in-law or guest house? BONUS: When you buy this home you also get the the "tiny home" at 734 Honeysuckle Trail at one price that has a kitchen, full bathroom and bedroom. Best part: both of these homes are deeded waterfront and expand your waterfront lot to 189feet. 734 Honeysuckle also has old pier pilings remnants for additional tie-ups. Don't miss this one! Looking for more land or bigger waterfront? No problem because these homes are part of a larger family compound with 739 Honeysuckle which is also for sale. Each of these are separately-deeded, stand-alone homes and buying all three could expand your potential. Buy the entire compound and move your family or friends in! Waterfront getaway delight! This could also make an incredible site for a custom built home. Call the listing agent for the details or for recommended architects & builders to complete your custom home vision. See other listing at: 739 #MDAA2003586 for sale, sold separately..

Listed by Kimberly Barton of Kinetic Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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6960 Thorneton Rd Royal Oak MD 21662

Royal Oak, MD6960 Thorneton Rd

Price$615,000

Est. Mortgage: $/month

MLS Number MDTA2000866

  • Single Family
  • Address 6960 Thorneton Rd
  • Bedrooms 4
  • Square Feet 2245
  • Year Built 1986

Amazing Contemporary home perfectly sited on a beautiful 4 acre parcel that allows so much privacy! This 2.5 story home has been meticulously maintained with many upgrades and shows incredibly well! It boasts an open floor plan with beautiful hardwood floors, 4 bedrooms, 3 1/2 baths. Enjoy the Living Room with vaulted ceiling and a corner wood stove! The Dining Room opens to a nice deck and outdoor dining area for entertaining! Read a book or watch a bit of TV in the Den. The Kitchen has silestone countertops and stylish cabinetry; there are stools at the counter as well as room for a table for casual meals. The entire home is light-filled with lovely views of the beautifully landscaped grounds. What the current owner calls a "meadow" allows room for a pool, pool house, guest house, tennis courts or whatever your heart desires! You will also enjoy an over-sized detached garage, two sheds for extra storage, a fire pit and so much more! It's important to mention that this is on public sewer, has an encapsulated crawl space and there are no town taxes! Also note, that though the Tax Records say it is Royal Oak, it actually is a 911 Easton address as well as for mail delivery. This is a must see!

Listed by Leslie J Stevenson of Long & Foster Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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5911 Elston Shore Rd Neavitt MD 21652

Neavitt, MD5911 Elston Shore Rd

Price$4,500,000

Est. Mortgage: $/month

MLS Number MDTA140742

  • Single Family
  • LocationType River
  • Address 5911 Elston Shore Rd
  • Year Built 2014
  • Bathroom 6

BREATHTAKING PRIVATE WATERFRONT ESTATE Turnkey 10-acre family Compound 1.5 hours from Washington DC and Baltimore, 2.5 hours from Philadelphia, and minutes from the nautical charm of St. Michaels. The recently constructed Main House and Carriage House, and the renovated Guest House invite numerous configurations to accommodate 14 guests. Every room affords gorgeous sunrises and spectacular water views at the confluence of the Tred Avon and the Choptank Rivers and the Broad Creek. Experience southerly breezes in a park-like setting at the Pool and 125' Dock with seating area, 2 power lifts, a swim/kayak platform and 4' MLW. Exceptional craftsmanship and finishes provide the ultimate in Chesapeake living. "Windsong"

Listed by Clifford E Meredith of Meredith Fine Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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7885 Avon Ct Easton MD 21601

Easton, MD7885 Avon Ct

Price$2,325,000

Est. Mortgage: $/month

Pending

MLS Number MDTA141240

  • Single Family
  • LocationType River
  • Address 7885 Avon Ct
  • Bathroom 7
  • Bedrooms 5

Spectacular waterfront family compound located off Mile Marker 21 on the Tred Avon River, one of Talbot County's finest and most prestigious waterways. Private beautifully landscaped point with 900+ feet of shoreline, broad East to West water exposure, high elevation, deep 6 foot mean low water multiple slip/lifts dock. Enjoy stunning sunsets and a mile-and-a-quarter long views down the Tred Avon from the rear of the main house, spectacular second story full length deck, heated pool and backyard patios. Property is ideally situated on private cul-de-sac off Oxford Road in Woodland Farms midway between downtown Easton (just four miles to shopping, restaurants, entertainment, medical services/hospital!) and Talbot Country Club, also conveniently located close to Easton airport, an hour from BWI and 1.5 to Baltimore and D.C. 3700+/- sf three bedroom main house , large 1680+/-sf two story two bedroom guest cottage with incredible family/game room, attached greenhouse, garage/workshop, storage sheds. Both main and guest have lightening protection systems; portable generator for guest house, six rear awnings, irrigation, exterior lighting. Pier is roughly 105' long with 6ft mlw verified by Bailey Marine; varies in width from 3'9" to 9'6"; has five lifts one at 12,000lb, two at 2800lb, one at 1200lb; two floating docks; five sets of well located stairs/ladders to water; three dock boxes; water, power, lights and a power washer. Property is a short distance from Easton Point for easy access to marine fuel. (Bedrooms 4 and 5, family room, 2nd kitchen, 2nd sunroom = greenhouse, 2nd half bath all in Guest Cottage.)

Listed by Janet R Larson of Benson & Mangold,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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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 October 20, 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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