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Eastern Shore Antique & Historic Homes for Sale

Antique House in MDBrowse all antique & historic homes for sale on the Eastern Shore of Maryland. You may also be interested in exploring all Eastern Shore homes.

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26020 Marengo Rd Easton MD 21601

Easton, MD26020 Marengo Rd

Price$5,850,000

Est. Mortgage: $/month

MLS Number MDTA141104

  • Single Family
  • LocationType Rural
  • Address 26020 Marengo Rd
  • Square Feet 6468
  • Bathroom 5

Knightly is one of the most iconic properties on Maryland's Eastern Shore. This historic waterfront estate was built in the 1820s by Edward Lloyd for his daughter, Elizabeth, and her husband, Edward Winder. Today, Knightly is an 81-acre farm on Leeds Creek in Talbot County located just across the Miles River from St. Michaels and seven miles from Easton. The Federal-style, two-story, three-bay, brick residence maintains a bucolic setting with farm fields on either side of a long tree-lined driveway approaching the front circle with immense trees. The house overlooks three acres of formal English gardens with views to Leeds Creek. The farm consists of 42 tillable acres, fenced pastures, a horse stable, outbuildings, including a caretaker cottage and farm office. The property has 1,200 feet of shoreline along Leeds Creek, including a dock with 6 feet of water at low tide. 'Knightly' has recently seen major improvements throughout the house and grounds. Meaningful upgrades with modern amenities and features to protect and preserve the structure, along with substantial updates rebuilding the pool, gardens, irrigation system, additional storage, and barn structures, combine to create an ideal Eastern Shore retreat.

Listed by Coard A Benson of Benson & Mangold,LLC

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$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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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101 N Water St Chestertown MD 21620

Chestertown, MD101 N Water St

Price$4,150,000

Est. Mortgage: $/month

MLS Number MDKE2000342

  • Single Family
  • Address 101 N Water St
  • Bedrooms 6
  • Square Feet 7440
  • Year Built 1769

"Widehall" is the most acclaimed historic downtown waterfront estate in Chestertown MD, since 1769. The many stewards of this magnificent residence, including two Maryland governors and two US Senators, have been ambassadors of hospitality for both town folk and national leaders. Each have protected and enhanced its authentic beauty ... from the original mahogany hanging staircase (c 1769) to geothermal heating and air (c 2013). Widehall is quite special to our town. The more formal main floor rooms provide the ideal setting for both parties and intimate gatherings. The flow between each of the rooms is perfect. Three of the six wood burning fireplaces add only a part of the warmth and ambiance of the main level of this residence. The chilled air or warm summer breeze is steps away on the first of two grand verandas overlooking the Chester River, thoughtfully added in 1911. Ascending the mahogany stairs to the second floor maintains the elegant feel of a grand home but immediately establishes a feeling of comfort and relaxation with a large family room. Surrounded by three bedrooms, each with their private baths, there are two doorways to the second of the very large waterfront verandas. A former servants wing provides for a bath, laundry room and windowed closet space. The top floor (number three) boasts three bedrooms, two baths and an additional laundry. Architects of a by-gone era creatively used dormer space for exquisite closet and storage space. Currently, each bedroom is named in honor of an acclaimed figure with close connections to Chestertown and the Eastern Shore. Your journey is not quite finished. A gracious staircase, discreetly hidden behind a wainscoted door, brings you to the unmatched "Widow's Walk" or rooftop deck with the most spectacular views of the Chester River and Chestertown. In many cities, a visit to this rooftop would be worth the price of a hefty admission. Our beautiful town and its people want to welcome you to continue the history and stories of "Widehall". Prospective buyers should be informed of the vital socio-economic trend this small town of America is experiencing and that of its acclaimed Arts & Entertainment District. Yes, our weekly Farmer's Market is "gossip central" and awesome for river and farm fresh provisions .... but it is the community that makes us a great place to to live. From monthly First Friday evenings for gallery and shop visits to a variety of annual festivals that include Downrigging weekend, Legacy Day, the Chestertown Tea Party reenactment, Dickens of a Christmas, and more add to the vibrancy of our town with Widehall enjoying the best viewing action. The convenience of a deep water dock and great lawn combined with short-walks to morning coffee and fresh pastries, evening cocktails and fine dining is unparalleled on the Eastern Shore.

Listed by Richard Keaveney of Cross Street Realtors LLC

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$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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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22598 Davis Creek Dr Rock Hall MD 21661

Rock Hall, MD22598 Davis Creek Dr

Price$3,500,000

Est. Mortgage: $/month

Pending

MLS Number MDKE100044

  • Single Family
  • LocationType Creek/Stream
  • Address 22598 Davis Creek Dr
  • Bathroom 4
  • Bedrooms 3

Enchanting Eastern Shore waterfront residence is nestled on 56-acres on Davis Creek in Rock Hall. Expert craftsmanship and style distinguish Winding Creek House, designed by Chestertown architect, Peter Newlin. A series of pavilions are linked to create an interior of inviting, flowing spaces. Each pavilion enjoys its own river views and landscape in perfect harmony with the tranquil and naturally beautiful eastern shore setting. A charming summer house (free-standing screen porch), 100 dock (4-ft mlw) with boat ramp, floating dock and boathouse are lovely settings to enjoy outdoor activities. Outstanding features of the home include an elevator, exquisite wood trim detail, built-in cabinetry, radiant floor heat, soaring two story living room, copper roof, granite kitchen and relaxing sauna. The small waterfront town of Rock Hall located on the Chesapeake Bay offers shops and dining. Historic Chestertown, home to Washington College, is just 20-minutes away and boasts the Chester River Walk, brick sidewalks lined with18th century homes, galleries, live theater, boat tours, cafes and restaurants. It also has a vibrant arts community, outdoor educational programs and waterfront park. Chestertown is about 90-minutes from Washington and Philadelphia.

Listed by Richard F Budden and Mary C Carlisle of Coldwell Banker Chesapeake Real Estate Company

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$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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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314 Friendship Manor Dr Stevensville MD 21666

MLS Number MDQA2000966

  • Single Family
  • Bathroom 10
  • Bedrooms 9
  • Year Built 1991
  • Square Feet 8494

Your Oasis awaits at this spectacular Kent Island Estate. Friendship Manor singularly connects the past and present offering a myriad of possibilities on a grand scale for the discerning buyer. With an unrivaled location this Fifty Seven +acres with Twenty Eight Hundred feet of water-frontage and Two Private Docks on Warehouse Creek offers the best in a rare close-in sanctuary for those seeking privacy. Luxury and Comfort for Living as well as Entertaining, a magical Guest Cottage, Detached Four Car Garage with Carriage House above (electric and plumbing rough outs in place) , Horse Paddocks and an oversized In-Ground Pool. This is the perfect location for Boating, Fishing, and Hunting. Only Three Miles to the Chesapeake Bay Beach club, Bay Bridge Airport and only a few minutes to Chesapeake Bay by Boat! The Main House was custom built in Nineteen Ninety One and boasts Five Bedrooms and Six and One Half Baths. You are greeted by Cathedral Ceiling and a Marble floor entryway. The expansive Great Room with immense natural light is adorned with a distinctive Fireplace. The Gourmet open Kitchen has absolutely stunning views. Large open flowing rooms and multiple Balconies and walls of Windows for spectacular views of the Warehouse Creek on all levels. Over Eight Thousand Square feet, this truly Low Maintenance and exquisite Custom Home offers everything you desire. The treasure of this property is the magical Historic Guesthouse. This historic home built in 1680 is on the National Historical Society list. This Charming and well cared for Historic House has Four Bedrooms and Three Bathrooms.

Listed by Adam E Light and Monika D Lynde of Monument Sotheby's International Realty

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$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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$2,795,000

Est. Mortgage: $/month

MLS Number MDTA136806

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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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26341 Arcadia Shores Ln Easton MD 21601

Easton, MD26341 Arcadia Shores Ln

Price$2,295,000

Est. Mortgage: $/month

Pending

MLS Number MDTA2001052

  • Single Family
  • Bedrooms 3
  • Year Built 1989
  • Square Feet 4907
  • Bathroom 4

Matterport 3D Walkthrough Aerial Video This is it! Private and ideally located between the historic towns of Easton and St Michaels, this waterfront estate checks every box. Huge southwest vista of the Miles River, brick construction, main-level owner's suite, waterside concrete pool, pier, and detached two car garage. All this and more on an exceptional, and very private, lushly landscaped park-like point lot at end of the street.

Listed by Chuck Mangold and C Edwin W Mangold of Benson & Mangold,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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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201 S Water St Chestertown MD 21620

Chestertown, MD201 S Water St

Price$2,100,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDKE2000704

  • Single Family
  • LocationType Downtown
  • Address 201 S Water St
  • Bathroom 2
  • Bedrooms 4

Eastern Shore magnificent Italianate style home, c.1857 with views of the Chester River is set in the historic district of Chestertown adjacent to the Hynson Ringgold House. In 2004 the carriage house was built next door and is designed with a water view apartment, garage and elevator. The main house spans three levels and greets owners through an elegant entry hall leading to the large porch overlooking the river. Gracious formal rooms project a welcoming yet sophisticated ambience enhanced with 11' ceilings, built-ins and fireplaces. The property is conveniently located just a walk away from the river, shops, restaurants, parks, cafes, oyster bar, theatre and walking trail. Founded in 1706, Chestertown is a lovely waterfront town and is home to Washington College. Residents and visitors alike enjoy the farmers market, parks, annual festivals, and river cruises on the Chester River Packet and the tall ship Schooner Sultana. Chestertown is located about 90 minutes from Washington, D.C. and Philadelphia.

Listed by Richard F Budden and Mary C Carlisle of Coldwell Banker Chesapeake Real Estate Company

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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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205 Cherry St Saint Michaels MD 21663

Saint Michaels, MD205 Cherry St

Price$2,025,000

Est. Mortgage: $/month

MLS Number MDTA2000072

  • Single Family
  • LocationType River
  • Address 205 Cherry St
  • Bathroom 9
  • Bedrooms 7

Once in a lifetime opportunity to own a St. Michaels iconic landmark waterfront property in a premier in-town location! This grand historic home is on the biggest waterfront lot overlooking the St Michaels harbor. Breathtaking views of the "Honeymoon" footbridge, Hollis Park, the Patriot Tour Boat, marinas & Navy Point, the home of Chesapeake Bay Maritime Museum. The main building is distinguished by it's elaborate 2nd Empire Mansard slate roof and Colonial Revival columned porches. Zoned R2 residential with a current home based business run as Aida's Victoriana Inn Bed and Breakfast. It's the only B&B in St. Michaels with a full, separate two bedroom, two bath Innkeepers house which would make a beautiful guest house. The property can be subdivided into two waterfront houses. There are seven bedrooms with four waterside bedrooms including a main level primary suite with a large private deck and sweeping views of the harbor. All rooms have separate controlled cooling. Three rooms have fireplaces. Plenty of access to the water via a public kayak launch, free Town day boat parking, overnight boat slips at the Museum and year round slip rentals next door at Higgins Yacht yard. Full basement in the main house provides ample storage. There is onsite parking for 10 cars. Commercial sprinklers throughout. Fully furnished with old world charm. Price is the same with or without furniture. Purchase price includes everything needed to start your own B&B business plus access to reservation and accounting system. Service for 120 person events is included. Town of St. Michaels B&B Inn license is good for unlimited events including weddings. Buyer must apply for license before settlement. Excellent high elevation with no current flood insurance. Financials only available after an in-person showing & a signed non-compete. This is a residential purchase with the ability for a buyer to start their own business. Current business is not for sale. Please do not go on the property without an appointment. Listing agent must accompany any showings. Showings must be scheduled around occupancy with at least 24 hours notice. Access to all rooms may need several showing appointments. History, plat and Features Sheet in MLS documents.

Listed by Kate Koeppen of Chesapeake Bay Real Estate Plus,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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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200 Wye Harbor Dr Queenstown MD 21658

Queenstown, MD200 Wye Harbor Dr

Price$1,975,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDQA147702

  • Single Family
  • LocationType Creek/Stream
  • Address 200 Wye Harbor Dr
  • Square Feet 5193
  • Year Built 1848

NEW PRICE! All the more reason to Saddle Up Your Horses & Start Living the Shore Life! Listed on the historic registry, 'Bryan Farm' is a beautifully restored manor that will take your breath away from the moment you enter the gates. You immediately sense its rich history and serene appeal. Nestled on nearly 17 acres along Sadlers Creek which leads to the renowned Wye River, the outdoor enthusiast will be in heaven... easy access to crab, fish, waterfowl hunt or simply take in the grandeur of life on Maryland's eastern shore. Plus with 15 acres fenced and a large dairy barn (built in 1870) complete with stalls, horses will frolic in the multiple pastures and peaceful setting. The nearly 5200 SF main house is the perfect blend of traditional and modern styles. You'll appreciate the over-sized rooms, 5 fireplaces (4 gas and 1 wood burning) and the comfortable flow giving everyone their own space. Major renovations in 2008 added a main level master suite with soaring cathedral ceilings and private bath, mudroom/laundry room, large family room with wood burning fireplace, built-ins and wet bar. The huge wrap porch was added at the same time and is a striking feature and a coveted place to gather in the warmer months. The second level features the original master suite with cozy gas fireplace that has balcony access to soak in the morning sun glistening across the pastures while enjoying a cup of coffee. Private bath features double vanities, standing shower and restored clawfoot tub. Across the hall is a sitting room that could serve as a private dressing room/walk in closet. There is a second sizeable bedroom with gas fireplace and direct entrance to the updated full bath in hallway. The third floor, like the entire home, is bursting with character with interesting rooflines and nooks. A fourth bedroom features a walk in closet and direct access to the remodeled full bath and access to another family room or living space. The third floor office has the potential to be used as a guest room or additional bedroom, school room, craft room--whatever your need! Outside the grounds are impeccable and feature a cement inground salt water pool with pergola. The setting is perfect for entertaining and has served as the stunning backdrop for family weddings. Just minutes to Route 50 this gem of a property is nicely tucked away from the hustle and bustle yet close enough to the outside world that you are never too far from anything.

Listed by Tricia Z Wilson of Chaney Homes,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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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8139 Stephen Decatur Hwy Ocean City MD 21842

Ocean City, MD8139 Stephen Decatur Hwy

Price$1,795,000

Est. Mortgage: $/month

MLS Number MDWO123034

  • Single Family
  • LocationType Creek/Stream
  • Bathroom 5
  • Square Feet 5643
  • Year Built 2003

Unique Waterfront Custom built Florida style home with indoor pool. Two Beautiful homes on this waterfront estate situated on 12.60 acres. Great for entertaining. Exceptionally well taken care off. Geothermal heat, boat dock with lift, beautiful fountain with s small fish pond. Large master suite of the pool with 2 walk-in closets, an office/den, large family room with game area, open floor concept, formal living room & more! Excellent location. Close to Ocean City and Assateaugue Island beaches as well as historic downtown Berlin, restaurants, water activities, schools, shopping and restaurants. The property features a 1,932 square foot guest house, with 3 bedrooms. 2 baths, Don't miss out on this unique opportunity! Contact you agent to schedule a private showing. Motivated seller and will consider serious offers from qualified buyers.

Listed by Imad Elali of Long & Foster Real Estate,Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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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23746 Mt Pleasant Landing Cir Saint Michaels MD 21663
Pending

MLS Number MDTA2001836

  • Single Family
  • LocationType River
  • Bedrooms 4
  • Year Built 1985
  • Square Feet 3870

Charming spacious one-level St. Michaels waterfront home on Broad Creek with sunset views! This home offers 4 bedrooms, a large open floor plan. A great room with a vaulted ceiling, skylights & fireplace adjoining dining area and an open concept kitchen with a beamed ceiling. A fabulous waterside sunroom with beautiful views. Waterview owner's suite with remodeled bathroom, and huge walk in closet. Game room/workroom/flex room, office. Paved driveway plus 3 car garage with auto openers. The 225 ft pier has a fairly new boat lift and deep water. Many recent renovations. Public sewer is coming soon. This home is deceivingly large. Minutes to Historic downtown St. Michaels.

Listed by Barbara C Watkins of Benson & Mangold,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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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10370 Bayside Dr Claiborne MD 21624

Claiborne, MD10370 Bayside Dr

Price$1,250,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDTA2001302

  • Single Family
  • LocationType Bayfront
  • Address 10370 Bayside Dr
  • Bathroom 2
  • Year Built 1900

Stunning sunsets with wide open views just 4+ miles to historic st michaels situated in the romantic village of claiborne . This hosue was raised, has 4 feet crawlspace, 2 sump pumps and french drain. It was also completly gutted and received all new windows, doors, foam insualtion, hardiplank siding, new roof, new electric, all systems, hvac 2 zones, new septic 2008, new well in 2012, travertine and reclaimed wood floors, gourmet kitchen with breakfast bar, ss appliances, gas range, mudroom, laundry room, and much more. Fabulous screened porch to enjoy the southwesterly views and breezes, waterside fire pit and enough space to install a waterside pool and/or deck.

Listed by Cornelia C Heckenbach of Long & Foster Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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 January 24, 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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