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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. 

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.

7103 First Avenue Queenstown MD 21658

Queenstown, MD7103 First Avenue

Price$995,000

Est. Mortgage: $/month

MLS Number MDQA2003172

  • Single Family
  • LocationType Bayfront
  • Address 7103 First Avenue
  • Subdivision Queenstown
  • Bathroom 4

THE BEST waterfront location for this portion of the bay just had a major price reduction. Look out your window to the water: to the Left a 100+ y/o Willow tree, a quiet creek, the Queenstown Golf Course, their boat house and often a skipjack docked there. To the right the Chester River, yet protected by a white sand spit knocking down the wave action but allowing the breezes to cool you all summer long. This is a must see location! Feel free to stay and soak up the 205' of waterfrontage as you Meet This House. Sitting outside the flood plain this 4 bedroom, 2 full/2 half bath coastal colonial has stacked enclosed porches and many recent upgrades including updated kitchen and bathrooms, hardwood flooring, recess lighting, wood burning fireplace and moldings to name a few. With more than 3000 sqft of living space you will enjoy your best life here. We can't overlook that this property has 1.5 acres so stepping out the front door provides a completely flat open yard with gorgeous 100+ y/o Magnolia. Being on the 1st street of downtown Queenstown, enjoy taking a stroll of this quant little town. While this property may become your short stay vacation rental investment, 2nd home, or primary home you or your guests will truly enjoy this slice of heaven. The subject property is being sold as a package consisting of 3 waterfront lots per the included plat, with the existing dwelling on two of these lots. The third lot may provide development flexibility for a carriage house or guest house. (buyer and agent must do their do diligence to understand to what extent this 3rd lot can further be developed)

Listed by Justin Disborough of Long & Foster Real Estate,Inc.

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$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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.

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7751 Rollyston Dr Saint Michaels MD 21663

Saint Michaels, MD7751 Rollyston Dr

Price$16,000,000

Est. Mortgage: $/month

MLS Number MDTA2002950

  • Single Family
  • Address 7751 Rollyston Dr
  • Subdivision None Available
  • Year Built 2016
  • Bedrooms 9

2 parcels totaling 91 acres on the Miles River. 4-level, furnished, 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.

Listed by Clifford E Meredith of Meredith Fine Properties

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$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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.

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10468 Golf Course Rd Ocean City MD 21842

Ocean City, MD10468 Golf Course Rd

Price$3,999,999

Est. Mortgage: $/month

MLS Number MDWO2000211

  • Single Family
  • LocationType Bayfront
  • Subdivision Captains Hill
  • Address 10468 Golf Course Rd
  • Bedrooms 5

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 Guesthouse, which combines over 5,000 sq ft of living space, offer 270-degree 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. This is a great property for all your "toys".......canal can easily accommodate large sport fishing boats, kayaks, wave runners and more. And with all the garage space - 5 car - park your fancy sports cars to cruise around the beach! Detached garage with guest house /bedroom and bath for added square footage. 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 Dolphins 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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$
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$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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.

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32180 Wilson Point Rd Galena MD 21635

Galena, MD32180 Wilson Point Rd

Price$7,900,000

Est. Mortgage: $/month

MLS Number MDKE2001420

  • Single Family
  • LocationType River
  • Subdivision Sassafras Cove
  • Year Built 1900
  • Bathroom 18

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

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$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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.

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235 Great Neck Rd Stevensville MD 21666

Stevensville, MD235 Great Neck Rd

Price$3,747,000

Est. Mortgage: $/month

Pending

MLS Number MDQA2003348

  • Single Family
  • LocationType Creek/Stream
  • Subdivision Stevensville
  • Address 235 Great Neck Rd
  • Bathroom 6

A true legacy property, this historic residence dates back to 1649 with deed signed by 2nd Lord Baltimore Cecil Calvert. This is your chance to become the 6th owner of this distinguished centuries old property and residence along Warehouse Creek. Once functioning as a major trading location for the region, Warehouse Creek features a deep channel to allow large boats of that era to maneuver up the creek to the 18th century warehouse and in return take tobacco and other trade items back to England. The main residence, looking strikingly similar to the home from centuries ago was thoughtfully renovated and expanded in 1997 by Winchester Construction. The charm and elegance was respectfully maintained and gracefully elevated to accommodate modern living. The telescoping floor plan effortlessly flows from room to room and delights with glimpses into the past. Beamed ceiling in the breakfast nook/gathering room, built-in cabinets, shelving and glass in the kitchen cabinets are constructed from the original home. The original doorway greets you as you step into the newly expanded entryway leading into the original structure of the home including the formal Living Room and Dining Room flanking the stairwell. Bringing the past to life is the custom mural depicting life on the water years ago which envelopes the walls of the dining room., conveniently painted on canvas to be easily removed if desired. Highlights of this spectacular home include the exquisite mahogany woodwork throughout the Library/TV room, tumbled marble flooring in sunroom with beadboard ceiling and floor to ceiling windows, 5 fireplaces, spacious bedrooms with ensuite baths and 3rd level sleeping loft or additional family room with full bath. Encompassing 34.6 acres, this magnificent property is surrounded by water with a small creek meandering through the site putting the main house, 2 car garage with arcade room above, and crab house on a private island. Enjoy the shady waterfront stone patio with gardens and lush lawn leading to the private pier and boat ramp for easy kayak/canoe launching The adjacent 5 acre parcel, 233 Great Neck Road (Tax ID:#1804076974) is included and provides a 3 bdrm, 2 bath waterfront guest house plus a multi-stall horse stable and a fenced pasture. Peaceful, serene, rural location just minutes from the Bay Bridge, Annapolis and beyond. Come tour this property in person to take in all it has to offer!

Listed by Bradley R Kappel of TTR Sotheby's International Realty

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$
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$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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.

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111 Murphy Ln Grasonville MD 21638

Grasonville, MD111 Murphy Ln

Price$3,890,000

Est. Mortgage: $/month

MLS Number MDQA2001462

  • Single Family
  • LocationType Bayfront
  • Subdivision None Available
  • Address 111 Murphy Ln
  • Bathroom 9

This is it! “The Owl's Playground” at 111 Murphy Lane in Grasonville, MD offers stunning water views and opportunities for fun or serenity no matter which way one's head turns. The property includes a main(complete renovation 2002) house and a separate guest house(built in 2013) with large windows, allowing one to appreciate all the surrounding waterfront, from just about every window. Set on 2.64 acres, this is the ultimate entertaining, private property offering so many amenities, as well as an additional property right down the road. The main residence has an open floor plan, high ceilings, two bedrooms plus bonus room/bedroom, three full bathrooms (one with a high-tech steam shower), custom closets, and a laundry room. The interior entertainment space includes a living room and dining area with a two-sided gas fireplace, four-season room and bar complete with two wine coolers. The kitchen boasts an impressive island, double ovens, a six-burner stove and large pantry. A separate room off the kitchen provides an additional refrigerator, wine cooler and a second dishwasher, to help with all your entertaining needs. Additionally, the property offers a bocce court, boat ramp, a Trex surface dock with (4' MLW), 2 boat lifts, jet ski lift, paddle board racks, heated concrete pool and state-of-the-art outdoor kitchen and grill area with additional refrigerators, an ice maker, misters and a nearby wood burning oven. After a day on the water, you may grab some drinks from two refrigerators in the outdoor entertaining shed off the main home and wash off using the outdoor shower. The guest house with glorious water views in all directions includes a living room with high ceilings, fully equipped kitchen, three bedrooms, three full bathrooms, custom closets, a washer/dryer and an equipped gym. The flooring is engineered hardwood and the home offers outside decking for appreciating the expansive water views and natural surroundings. The guest house has its own septic. Both homes on Murphy Lane are equipped with installed generators, expansive outdoor lighting providing a resort-like feel at night, the grounds are fully irrigated, and the shoreline is rip rapped and bulkhead protected. Included with this listing is an additional property known as “Pebble Lane” at 112 Greenwood Point Rd(complete renovation 2014). This property is just a short ride from the main property and includes a cedar shake home set on nearly 3.5 plush green acres. The cozy home has two bedrooms, 2 ½ bathrooms, a living room, dining area, modern kitchen and washer/dryer. The property also contains a steel barn equipped with A/C and WiFi and can be used for storage and/or entertaining. Both properties convey with designer furnishings/custom bedding, linens, decorations, wall art, dishes/glassware/cookware, and includes 3 golf carts, a gator, and many water toys, making this entire, property one that is all about having around-the-clock fun with friends and family. Not to mention, Prospect Bay Country Club is right around the corner, offering golf, tennis, and a lovely club house! The acreage information provided in this listing is believed to be accurate, but should be confirmed by the Buyer. This listing is by appointment only, to be shown with the listing agents. Please do not enter the properties without having an appointment. Co-Listers- Tracy Wagner and Tiffany Cloud

Listed by Clifford E Meredith and Tracy Higgs Wagner of Meredith Fine Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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.

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22020 Benders Ln Sherwood MD 21665

Sherwood, MD22020 Benders Ln

Price$5,650,000

Est. Mortgage: $/month

Pending

MLS Number MDTA135344

  • Single Family
  • LocationType River
  • Address 22020 Benders Ln
  • Subdivision None Available
  • Square Feet 10781

Harris Creek Farm - 128 acres with development potential, improved by a 10,525 sq ft 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 an 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 a whole house basement offering an abundance of storage and easy access to mechanical equipment. First-floor guest suite, second-floor primary suite 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 the listing agent for additional information or scheduling.

Listed by Coard A Benson of Benson & Mangold,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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.

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3104 Bayview Dr Church Creek MD 21622

Church Creek, MD3104 Bayview Dr

Price$470,000

Est. Mortgage: $/month

MLS Number MDDO2002506

  • Single Family
  • LocationType Canal
  • Address 3104 Bayview Dr
  • Subdivision Swan Harbor
  • Bathroom 1

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

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$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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.

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4568 Boone Creek Rd Oxford MD 21654

Oxford, MD4568 Boone Creek Rd

Price$2,695,000

Est. Mortgage: $/month

MLS Number MDTA2002954

  • Single Family
  • Subdivision Oxford
  • Address 4568 Boone Creek Rd
  • Square Feet 3967
  • Bathroom 3

Welcome to this beautifully maintained waterfront home on Boone Creek in Oxford, MD. This home has panoramic, sunset waterviews, a large waterside deck, stunning in-ground swimming pool, and cottage style guest house. The main residence is loaded with impeccable custom finishes, open floor plan great for entertaining, a stylish gourmet kitchen, great room with cozy fireplace, main level owner's suite with fabulous incredible views, plus 3 additional bedrooms. Overlooking Boone Creek, the guest house offers a full kitchen with stainless steel appliances, open living room with dining area, bedroom, bonus room and waterside deck, with close access to the swimming pool. Private pier, floating dock and protected shoreline. Located only minutes to the Historic waterfront town of Oxford, restaurants, parks, marinas, shopping, beach areas, dog park, tennis courts, and the Oxford Community Center.

Listed by Barbara C Watkins of Benson & Mangold,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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.

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10373 Locust Point Rd Princess Anne MD 21853

Princess Anne, MD10373 Locust Point Rd

Price$3,500,000

Est. Mortgage: $/month

MLS Number MDSO2001830

  • Single Family
  • Subdivision None Available
  • Year Built 1740
  • Bedrooms 5
  • Bathroom 6

"Almodington" is one of Somerset Counties most elaborate mid-18th Century Georgian Plantation properties consisting of 203 waterfront acres on the Manokin River. This property is improved by the Manor House, Guest House, Garage with apartment above and multiple outbuildings. Recent upgrades include new cedar shake roof, new dock, new geo-thermal heating and air, new Marvin windows and two 10+ acre waterfowl impoundments. Excellent waterfowl, deer, dove and turkey hunting with the guest house be a successful Airbnb Rental. Property has been preserved by a Conservation Easement.

Listed by Henry Gibbons-Neff Jr. of Meredith Fine Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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.

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6243 Boston Cliff Rd Easton MD 21601

Easton, MD6243 Boston Cliff Rd

Price$2,695,000

Est. Mortgage: $/month

MLS Number MDTA136806

  • Single Family
  • LocationType Rural
  • Address 6243 Boston Cliff Rd
  • Subdivision Easton
  • Year Built 1676

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: 5.25% last updated on May 19, 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.

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400 Greenwood Creek Ln Grasonville MD 21638

Grasonville, MD400 Greenwood Creek Ln

Price$2,179,000

Est. Mortgage: $/month

MLS Number MDQA2003162

  • Single Family
  • Subdivision Prospect Plantation
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 4200

Welcome to the Eastern Shore of Maryland. Beautiful waterfront on Greenwood Creek-off Prospect Bay- with private 6 + slip pier and all the amenities that you look for on the water! Over 5 acres with enough land for horses...and to have your own driving range in the front yard. The main residence (about 4200 sq ft ) offers four bedrooms, gourmet kitchen and great room overlooking the pool, attached garage with your own Tesla charging station and great views. The beautiful, detached guest house (about 640 sq ft) is expansive with its own kitchen and has a deck overlooking the water. The property also includes an attached 32 x 20 crab house with everything you need to enjoy your crabs this Summer and numerous decks and patios to enjoy the spectacular views. The 37 x 18 inground pool will be where you spend most of your days. The gardens and the fruit orchards will be an added bonus. Apricots, blueberries, peach, plum, cherries, figs, apples, pears and even your own concord grapes! All in your own front/back yard. The 60-foot pier will be ideal to catch your crabs, fishing, and to enjoy all watersports. Prospect Bay 18-hole golf course is only a short golf cart away. You can become a member or not, your preference. Social memberships also available for those with not enough time to golf. Just 10 minutes from the Chesapeake Bay Bridge and close to Easton and Annapolis. Welcome Home!

Listed by Biana J Arentz of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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.

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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 May 20, 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.

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