Benson & Mangold Real Estate, 31 Goldsborough St, Easton, MD 21601 410.822.6665 | Office

Search Homes:

Eastern Shore Homes with a Guest House

Home with Guest House in BackyardView listings for homes with a guest house on the Eastern Shore of Maryland. Whether you are looking for a guest house for inlaws, family, friends, or all of the above, a guest house gives them plenty of room and privacy when they come to visit. 

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. 

Save time! Create a free account to save your favorite listings and get notified when similar properties become available. You may also be interested in browsing all Eastern Shore homes.

121 Lyons Lane Chestertown MD 21620

Chestertown, MD121 Lyons Lane

Price$875,000

Est. Mortgage: $/month

Coming Soon

MLS Number MDQA2004878

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,327
  • Acreage 1.9

This listing offers the unique opportunity to own two waterfront parcels, one improved by a beautiful 3-4 bedroom cape, and an adjacent perc approved lot all located less than a mile from Chestertown. The addresses are 121 Lyons Ln. which is 1.9 acres, 118 Lyons Ln. which is 1.2 acres and 117 Lyons Ln. which is .44 for a total of 3.5 acres. They are being sold together and the tax information is for all three lots. The cape is on the 1.9 acre wooded lot and features premium materials and finishes. There are yellow pine floors reclaimed from Camden Yards, crown moulding, wainscoting, panel doors, fireplace, sun room and a master bedroom on the first floor. The second floor has two bedroom and a third room which could be a bedroom, office or 2nd floor family room. The second floor bathroom is huge and has just been remodeled. There is also a separate studio or home office, also recently remodeled, in the rear yard with AC/Heat. A Williamsburg inspired garden surrounds the studio and the rear yard is partially fenced. The waterfront is a quiet creek right across the Chester River from the historic district. The owners have a permit for a new dock and it will convey. By the water is a large screened in Gazebo perfect for crab feasts or for enjoying the abundant wildlife. The second waterfront lot is 1.2 acres, not buildable, but it does allow for more water access. The third lot is .44 acres, perc approved, level, cleared but with some mature trees . A second home could be built for a family compound or a carriage house, guest house or barn. Or, simply hold on to it as an investment. Lots of options so come take a look!

Listed by Tracy A Stone of Coldwell Banker Chesapeake Real Estate Company

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

24622 Pealiquor Road Denton MD 21629

Denton, MD24622 Pealiquor Road

Price$474,000

Est. Mortgage: $/month

MLS Number MDCM2002162

  • Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,416
  • Acreage 1.38

Two stunning homes set upon your private 1.38 acre oasis, with lush landscaping & charm galore await you! Beautiful Colonial Home with exposed beams, gleaming hardwood floors, built-ins, 2 wood burning fireplaces, spacious eat-in kitchen and tons of character, featuring 3 Bedrooms and 1.5 Bathrooms. Relax or entertain on your fabulous porch, surrounded by beautiful cedar shake siding! Must see to appreciate! Guest Home is fully equipped with kitchen, living room, 1 Bedroom & 1 Bathroom & it's own laundry area with washer & dryer hookups! Multigenerational Living at a price you can afford, situated on a lush landscape with mature trees, and lovely 1.38 acre yard. Huge Garage workshop with a finished bonus room above & lean-to so you never run out of storage space! Lovingly maintained, and waiting to be your new perfect oasis! Country, neighborhood feeling in a rural setting, yet close to downtown Denton for shopping, dining & more! Only a 1 hour drive to the Beaches! Main house built in 1994 with approximately 1696 SF and Guest House built in 1999 with approximately 720 SF. You don't want to miss this one!

Listed by Erin Anderson of Chesapeake Real Estate Associates,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

4025-4135 Elliott Island Road Vienna MD 21869

MLS Number MDDO2003402

  • Single Family
  • Bedrooms 11
  • Bathroom 14
  • Square Feet 10,350
  • Acreage 997.12

AUCTION! AUCTION!! AUCTION!!! For MLS purposes only, the list price is Suggested Opening Bid. Bid YOUR price at auction. Steam Mill Farm consists of nearly 1000 acres and over 8000 feet of unobstructed deep-water frontage with five houses (11 bedrooms, 10 full, 4 half baths), office/library building, stable and support buildings. Each of the farms have their own private entrance from Elliott Island Road and have continuously remained individually deeded. Boog Farm with its 330 acres at 4135 Elliott Island Road comprises the primary farm house, flawless stable, stand-alone office/library, impeccable guest house, a separate laundry/storage and a spa pool. The equestrian facility encompasses a stunning, expansive 8 stall stable with its stately finishes and refined design surrounded by magnificent paddocks and miles of scenic riding trails. Additionally, the property includes 1720 (+/-) feet of fabulous unobstructed river frontage, significant wooded Sika deer hunting grounds and as with all the farms, active, rotating crops managed with a local farmer. Webb Farm with its 130 acres at 4125 Elliott Island Road contains the totally refurbished guest house, dock house, deep water dock reaching depths of 12 feet, duck pond and 4-bay maintenance barn. With its dramatic 2410 (+/-) feet of unobstructed river frontage, tillable farm acres, secluded duck pond and tranquil setting, the property is a magnate for wild turkeys and waterfowl of numerous species. The 3800 (+/-) sq. ft. maintenance barn represents opportunities for additional diverse uses. Willey Farm with its 120 acres at 4025 Elliott Island Road includes the original farm house (guest quarters), an inviting swimming pool with a separate cocktail pool, pool house and impeccable guest cottage. Its tillable farmland and the 181 acre adjacent hunting marsh make for a matchless private setting. Every structure has been meticulously constructed, restored and refurbished with the finest materials and craftsmanship. By way of example, the cedar shake roofs, all wood siding, hand-made doors and shutters demonstrate that no detail has been overlooked. Each property is equipped with a top-of-the-line HVAC system, foam insulation, French drains, water purification systems and high-end appliances to name but a few of the many discriminate attributes each structure enjoys. The properties have individually and collectively been painstakingly renovated to appropriately represent the history of the region with touches such as hand crafted, exquisite cabinetry while incorporating the most modern technological advances. Three original farmsteads and two additional duck marsh parcels for conservation and hunting are to be offered separately and in the entirety. Auction to be held on Wednesday, October 12th at 2:00 pm (ET) online and onsite at 4135 Elliott Island Road, Vienna, MD. For MLS purposes only, the list price is low Agricultural use tax assessment Bid YOUR price at auction. Please be sure to view all the virtual tours. 4135 Elliott Island Rd 329.87 acres Parcel 1011001394 4125 Elliott Island Rd 129.75 acres Parcel 1003044785 4025 Elliott Island Rd 120.00 acres Parcel 1011001394 Parcel 19 Elliott Island Rd 181 acres marshland Parcel 1011002404 Parcel 13 Hurleys Neck Rd 236.5 acres marshland Parcel 1001005049

Listed by Jeffrey E Stein of Jefferson Realty Group,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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

32180 Wilson Point Road Galena MD 21635

Galena, MD32180 Wilson Point Road

Price$5,800,000

Est. Mortgage: $/month

MLS Number MDKE2001420

  • Single Family
  • Bedrooms 6
  • Bathroom 9
  • Square Feet 18,440
  • Acreage 18.31

Can your investments pay these dividends. Sassafras River Compound uniquely centered in between New York City, Philadelphia, Baltimore and Washington DC. Less than one hour from Philadelphia International Airport. 17 bedrooms 16.5 baths, 1900's renovated Manor house with spectacular down river views and summer sunsets. Find your favorite resting spot on the dock, the Manor house the Cottage, Pool house, Guest house or in the Barn tavern. Perfect location for plenty of water sports, Water skiing, Wakeboarding, Sailing, Paddle boarding and fishing. Just minutes by boat to Georgetown Harbor, with 5 restaurants. Must see to appreciate, but make sure you block out enough time to see all this Upper Eastern Shore gem has to offer.

Listed by John J Burke of Gunther-McClary Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

4135 Elliott Island Road Vienna MD 21869

Vienna, MD4135 Elliott Island Road

Price$1,290,433

Est. Mortgage: $/month

MLS Number MDDO2003386

  • Single Family
  • Bedrooms 5
  • Bathroom 8
  • Square Feet 6,350
  • Acreage 329.87

AUCTION! AUCTION!! AUCTION!!! For MLS purposes only, the list price is low Agricultural use tax assessment Bid YOUR price at auction. Steam Mill Farm consists of nearly 1000 acres and over 8000 feet of unobstructed deep-water frontage with five houses (11 bedrooms, 10 full, 4 half baths), office/library building, stable and support buildings. Each of the farms have their own private entrance from Elliott Island Road and have continuously remained individually deeded. Boog Farm with its 330 acres at 4135 Elliott Island Road comprises the primary farm house, flawless stable, stand-alone office/library, impeccable guest house, a separate laundry/storage and a spa pool. The equestrian facility encompasses a stunning, expansive 8 stall stable with its stately finishes and refined design surrounded by magnificent paddocks and miles of scenic riding trails. Additionally, the property includes 1720 (+/-) feet of fabulous unobstructed river frontage, significant wooded Sika deer hunting grounds and as with all the farms, active, rotating crops managed with a local farmer. Every structure has been meticulously constructed, restored and refurbished with the finest materials and craftsmanship. By way of example, the cedar shake roofs, all wood siding, hand-made doors and shutters demonstrate that no detail has been overlooked. Each property is equipped with a top-of-the-line HVAC system, foam insulation, French drains, water purification systems and high-end appliances to name but a few of the many discriminate attributes each structure enjoys. The properties have individually and collectively been painstakingly renovated to appropriately represent the history of the region with touches such as hand crafted, exquisite cabinetry while incorporating the most modern technological advances. Three original farmsteads and two additional duck marsh parcels for conservation and hunting are to be offered separately and in the entirety. Auction to be held on Wednesday, October 12th at 2:00 pm (ET) online and onsite at 4135 Elliott Island Road, Vienna, MD. For MLS purposes only, the list price is low Agricultural use tax assessment Bid YOUR price at auction. Please be sure to view all three virtual tours

Listed by Jeffrey E Stein of Jefferson Realty Group,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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

4125 Elliott Island Road Vienna MD 21869

Vienna, MD4125 Elliott Island Road

Price$383,933

Est. Mortgage: $/month

MLS Number MDDO2003392

  • Single Family
  • Bedrooms 1
  • Bathroom 2
  • Square Feet 1,156
  • Acreage 129.75

AUCTION! AUCTION!! AUCTION!!! For MLS purposes only, the list price is low Agricultural use tax assessment Bid YOUR price at auction. Steam Mill Farm consists of nearly 1000 acres and over 8000 feet of unobstructed deep-water frontage with five houses (11 bedrooms, 10 full, 4 half baths), office/library building, stable and support buildings. Each of the farms have their own private entrance from Elliott Island Road and have continuously remained individually deeded. Webb Farm with its 130 acres at 4125 Elliott Island Road contains the totally refurbished guest house, dock house, deep water dock reaching depths of 12 feet, duck pond and 4-bay maintenance barn. With its dramatic 2410 (+/-) feet of unobstructed river frontage, tillable farm acres, secluded duck pond and tranquil setting, the property is a magnate for wild turkeys and waterfowl of numerous species. The 3800 (+/-) sq. ft. maintenance barn represents opportunities for additional diverse uses. Every structure has been meticulously constructed, restored and refurbished with the finest materials and craftsmanship. By way of example, the cedar shake roofs, all wood siding, hand-made doors and shutters demonstrate that no detail has been overlooked. Each property is equipped with a top-of-the-line HVAC system, foam insulation, French drains, water purification systems and high-end appliances to name but a few of the many discriminate attributes each structure enjoys. The properties have individually and collectively been painstakingly renovated to appropriately represent the history of the region with touches such as hand crafted, exquisite cabinetry while incorporating the most modern technological advances. Three original farmsteads and two additional duck marsh parcels for conservation and hunting are to be offered separately and in the entirety. Auction to be held on Wednesday, October 12th at 2:00 pm (ET) online and onsite at 4135 Elliott Island Road, Vienna, MD. For MLS purposes only, the list price is low Agricultural use tax assessment Actual price to be determined at AUCTION! Please be sure to view all three virtual tours

Listed by Jeffrey E Stein of Jefferson Realty Group,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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

301 Sportsman Neck Circle Queenstown MD 21658

MLS Number MDQA2002364

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 4,580
  • Acreage 20.66

20 acre estate located on the Wye River. Main 3 bedroom, three bath house with open first floor, outdoor living space with hot tub, separate two bedroom two bath guest house that generates $40,000. of income per year through AirBB. Large dog kennel with apartment above, 19 stall horse barn, tack room and wash room with 8 paddocks and 2 riding rings. Very successful businesses on site with the ability to continue operations.

Listed by Glenn M Sutton of TTR Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

31598 Miller Road Cordova MD 21625

Cordova, MD31598 Miller Road

Price$275,900

Est. Mortgage: $/month

MLS Number MDTA2003774

  • Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 1,968
  • Acreage 2

Looking for that country location on a wooded lot well come take a look at this 4 bedroom, 2.5 bath cape cod with an additional structure that houses a 1 bedroom, 1 bath guest house. Large wrap around porch off the back of the house. Bring your imagination to make this house your home.

Listed by Pamela L Geib of Long & Foster Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

3104 Bayview Drive Church Creek MD 21622

Church Creek, MD3104 Bayview Drive

Price$435,000

Est. Mortgage: $/month

MLS Number MDDO2002506

  • Single Family
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 1,120
  • Acreage 2.88

Your own private getaway on the Eastern Shore! Enjoy peace and quiet and watch the stars from this cute 3 BR cottage. Wide water views are offered over Tar Bay from the living room and the deck. Partially wooded with paths to the canal, and direct access to Houston Cove and the Bay. Take your boat to the sand bars for summer fun. Dock with boat lift. Nice detached two car garage plus another shed and carport. Three parcels - one of the additional parcels is Health Department approved - build a guest house or sell it.

Listed by Valerie P Brown of Charles C. Powell,Inc. Realtors

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

27189 Island Creek Road Trappe MD 21673

Trappe, MD27189 Island Creek Road

Price$19,950,000

Est. Mortgage: $/month

MLS Number MDTA2003356

  • Single Family
  • Bedrooms 4
  • Bathroom 8
  • Square Feet 14,137
  • Acreage 121.21

Cecilia's Point - First-time offered...Spectacular...Nothing like it! 4 BR/4 BA/4 HB main house, 5BR/5BA guest house, detached garage with 2 BR/2 BA guest apartment, exquisite finishes and craftsmanship throughout, elevator, heated, saltwater pool, spa, cabana with bath, pickle ball courts, fairway with putting green, bocce ball court, broad westerly views of Choptank River, sandy beach, riprapped shoreline, deep water dock, 2 boatlifts, 4 jet ski lifts, tidal pond, kayak launch, fire pit, built-in grills with direct propane, hardwired internet, raised bed gardens, fountains, balconies, porches, paved driveway, brick and slate walkways and parking pad, mature trees, garage space for 10 cars, 2-bay pole barn. Conveniently located near country club, Downtown Easton, shops, restaurants, healthcare, and jet airport.

Listed by Clifford E Meredith of Meredith Fine Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

7751 Rollyston Drive Saint Michaels MD 21663

Saint Michaels, MD7751 Rollyston Drive

Price$15,000,000

Est. Mortgage: $/month

MLS Number MDTA2002950

  • Single Family
  • Bedrooms 9
  • Bathroom 13
  • Square Feet 20,912
  • Acreage 91.19

2 parcels totaling 91 acres on the Miles River. 4-level, main house with elevator, full basement, 9 bedrooms, 9 full baths, 4 half baths, media room, main level bedroom. 4-car garage with rec room, bedroom, full bath and half bath. Heated, waterside pool, pool house with 2 full baths/changing area, covered outdoor kitchen. Pond with fountains, dock, 2 gazebos. Partially riprapped shoreline, sandy beach, dock with water and electric. Guest house with 3 bedrooms, 3 full baths, 1 half bath, barn. Property is priced at $15,000,000 unfurnished. Some furnishings could be included at a price to be determined prior to closing. Or, property can be bought furnished for $16,000,000 with the exception of artwork, personal items, and certain pieces of furniture, etc. that will not convey. Such items will be disclosed to the Buyer within 10 days of a satisfactory contract.

Listed by Clifford E Meredith of Meredith Fine Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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

26908 Plantation Road Crisfield MD 21817

Crisfield, MD26908 Plantation Road

Price$180,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDSO2002368

  • Single Family
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 1,100
  • Acreage 0.81

Cute and Cozy 3 bedroom 1 bath rancher on nice corner lot. Metal roof and wrap around porch add to the charm. Attached garage has been turned into a fully separate 1 bedroom apartment with it's own private entrance . Partially wooded lot gives plenty of shade. Live in main part of house and rent out apartment or use as a guest house / in law suite. Seller is willing to help with Closing Costs with an acceptable offer.

Listed by Wendy Stever of Long & Foster Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

Copyright 2022 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 6, 2022. 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.

Get In Touch Today

Contact Chuck