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Chesapeake Bay Waterfront Homes for Sale

Waterfront Home in MarylandMany of the waterfront homes on the Chesapeake Bay offer spectacular views and some of the best sunsets on the Eastern Shore. Whether you’re looking for a waterfront home in Stevensville, Queenstown, or another Eastern Shore town, you’ll find a variety of waterfront homes to choose from. Discover the latest waterfront homes for sale on the Chesapeake Bay right here! You may also want to view all Eastern Shore waterfront homes for sale.

Search Chesapeake Bay Waterfront Homes for Sale Maryland

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7402 Kent Point Rd Stevensville MD 21666

Stevensville, MD7402 Kent Point Rd

Price$5,500,000

Est. Mortgage: $/month

MLS Number 1001760382

  • Single Family
  • LocationType Bayfront
  • Address 7402 Kent Point Rd
  • Bathroom 11
  • Bedrooms 8

Maryland's most beautiful and prestigious address. Stunning views, majestic grounds, gracious and stylish home. Come home to PARADISE EAST - 22,000 sqft of superb living space on 30 gorgeous acres of Chesapeake Bay waterfront. Recently re-mastered with updates to the main level Master Suite, Atrium, Chef's Kitchen, Gathering Room, Main Great Room, Pool and Smart-Home technologies. One visit is all it takes to fall in love. Boasting 2 level Private Movies Theater with Balcony seating, Club Room, Billiard and Game Room, Observatory with Widow's Walk, Fitness Room, Elevator, Safe Room, plus a huge Carriage House with Showroom and 3-bedroom Guest Quarters, separate Pool House with Kitchen and Spa Bath, Private Pool and Spa, Fire Pit, complete with private 150' Pier with multiple lifts. Your own private oasis, and within easy reach of WASHINGTON DC, BALTIMORE, PHILADELPHIA, NEW YORK CITY, all major commuter lines and 3 major east coast airports - DULLES, BWI, REAGAN NATIONAL. Less than 10 Miles to Bay Bridge Airport for private travel options.

Listed by Peter A Fettig Jr. and John F Reynolds of Keller Williams Flagship of Maryland

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$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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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220 Lighthouse View Dr Stevensville MD 21666

Stevensville, MD220 Lighthouse View Dr

Price$4,995,000

Est. Mortgage: $/month

MLS Number MDQA144968

  • Single Family
  • LocationType Bayfront
  • Bathroom 9
  • Bedrooms 6
  • Square Feet 9000

Escape to another world with this striking New England-inspired waterfront estate resting on the banks of the Chesapeake Bay. Situated on 1.8 acres with 422 feet of water frontage, this ultra-luxe 9,000 square-foot, 6 bedroom, 9 bathroom custom Nantucket Shingle-style home was built in 2016 and curated with premium quality, low-maintenance materials. Combined with the breath-taking sunset views, exquisite design, waterfront pool and top-tier finishes, 220 Lighthouse View Drive is truly one-of-a-kind and showcases unparalleled craftsmanship. The property both inside and out is an absolute entertainer's dream. The 2-story light-filled entrance graciously welcomes you with a marvelous grand staircase and soaring ceilings above. An elevator, 6 bedroom suites plus the separate bonus space with full bath above the three-car garage provide a high level of comfort for all. The interior flow is open and spacious, complemented with a chef's kitchen complete with commercial-grade appliances, waterside bar and billiard room, 700-bottle wine room, circular dining booth and 2 main level powder rooms. The owner's suite is second to none and every detail from the expansive private waterside deck to the seating area overlooking the fireplace and the Chesapeake Bay is breathtaking. The master bath feels like a spa retreat with a cavernous steam shower, free-standing soaking tub, dual vanities, private waterfront balcony and the spacious master closet with a plethora of custom built-in's is a fashionista's dream. The voluminous covered porch spans the entire waterside of the home and features Marvin doors that fold flush to create an open-air space plus electric screens that easily retract. The home was designed to be super efficient with state -of-the-art features including a geothermal system, gas furnaces, tankless water heaters and a backup generator. Outside, you can find lush landscaping, an infinity edge saltwater heated pool, in-ground hot tub, outdoor kitchen, gas fire accents plus a stone patio with a gas fireplace. There, you can behold a unique view - a trifecta of the Bloody Point Bar Lighthouse, Thomas Point Lighthouse and the Bay Bridge. The private pier with 5 feet of water depth is fitted out with a 35,000-pound boat lift, 4 jet ski lifts and is a quick 15-mile cruise by boat to St. Michael's or the Annapolis harbor. Why look anywhere else? This is the one! Don't miss your opportunity to secure arguably the nicest waterfront home currently for sale on the Chesapeake Bay! To explore the property without leaving your home, be sure to view the Matterport virtual tour and the HD video tour: https://youtu.be/YVbPFH_iSvA

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

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$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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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6558 Bozman Neavitt Rd Neavitt MD 21652

Neavitt, MD6558 Bozman Neavitt Rd

Price$4,495,000

Est. Mortgage: $/month

MLS Number MDTA132860

  • Single Family
  • LocationType River
  • Bathroom 6
  • Bedrooms 5
  • Square Feet 7462

"Clear Waters at Turkey Neck Point" is located just 10 miles (

Listed by Thomas M Crouch of Benson & Mangold, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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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6201 Swan Creek Rd Rock Hall MD 21661

Rock Hall, MD6201 Swan Creek Rd

Price$4,490,000

Est. Mortgage: $/month

MLS Number 1000487872

  • Single Family
  • LocationType Bayside
  • Address 6201 Swan Creek Rd
  • Bathroom 8
  • Bedrooms 8

To view the entire video tour with drone footage please visit: https://youtu.be/yxc_tvc6RO4 (or Search Swan Point Farm within YouTube)Live your dream and enjoy an elegant and serene waterfront estate nestled on 177+ acres of a private and secluded peninsula along Maryland's Eastern Shore. Delight in the commanding and expansive views of the surrounding farmland and the picturesque Chesapeake Bay. The views are rivaled only by the impressive and completely renovated 5,500+ square foot classic 19th-century farmhouse. This majestic property features beautiful 100-year-old reclaimed heart pine flooring, an open floor plan with an abundance of natural light, four master suites, two additional guest bedrooms, a powder room, and a home office with custom bookshelves. Enjoy many options for casual or formal entertaining inside the house, outside on the sprawling lawn or around the relaxing pool and hot tub. You or your guests can also retreat to the one bedroom cottage situated along the shoreline. Its oversized windows provide captivating panoramic views of the bay. No matter what you feel like doing, there is something for everyone. You might take a refreshing dip in the pool, barbecue with guests on the large side deck, play a few rounds of tennis on the fenced-in hardtop court, enjoy the sunset from a rocking chair on the front porch or stargaze from the widow's walk. The estate is also the ultimate retreat for outdoor sportsmen & enthusiasts. Boaters will appreciate the private pier tucked in a protective cove on Tavern Creek. It is the perfect place to fish and crab for the evening's meal. You may also launch boats from the property's boat lift, floating dock or cement boat ramp. Grab your kayak from the boathouse and spend the day watching ospreys and blue herons while exploring the bay and the surrounding waterways. With its ideal location, you are just minutes away from some of the Chesapeake Bay's finest marinas and authentic waterside restaurants. Private and remote while being close to major Mid-Atlantic metropolitan areas, this Eastern Shore jewel is sure to give you and your family a lifetime of memories. The Main House: This 1870s farmhouse had a complete renovation from the foundation up along with a major addition in 1998. 5,500+ sq. ft. - 6 bedrooms/5.5 bath home. 3 full levels w/ partly finished basement. 3 woodburning fireplaces / 2 propane. Widow's walk / sundeck with 360 degree views. Large, covered front porch. Designed for both formal entertaining and causal living. Reclaimed heart pine flooring throughout. Original staircase and mouldings. The Cottage on the water's edge: 1 bed/1 bath with expansive waterviews. Situated along the Chesapeake Bay and protected Tavern Creek. Large, waterside deck. Waterside patio. Wood flooring throughout. Open floorplan designed for every room to have a view of the water. The Accessory Structures: Garage with 1 bed/1 bath above, attached fenced in dog pen. Converted dairy barn with two levels of storage. Storage shed for fuel & decoys. Dry boat house with a cement ramp for ease of launching small boats and running water. Pier with electric boatlift, floating dock, power and running water located on Tavern Creek with easy access to the Chesapeake Bay. Heated inground pool with built-in hot tub. Tennis court - fenced-in hardtop. The Grounds & Property Features: Ultimate privacy on 177+ acre waterfront peninsula. Gated entrance providing additional privacy. Two waterfowl ponds & 3 duck blinds. More than 1.5 miles of waterfront shoreline. All 4 contiguous lots are waterfront and each have separate tax ID's. Lot 2 / 36.74 acres - Lot 3 / 22.28 acres - Lot 4 / 78.18 acres - Lot 5 - / 40.63 acres- Agricultural conservation easements are available for review by request.

Listed by Brent J Allen of Long & Foster Real Estate, Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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$4,250,000

Est. Mortgage: $/month

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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$
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$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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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24378 Deep Neck Rd Royal Oak MD 21662

Royal Oak, MD24378 Deep Neck Rd

Price$4,200,000

Est. Mortgage: $/month

Open House

MLS Number MDTA139296

  • Single Family
  • Next Open House: Thu 10/1 10:00 am. to 1:00 pm.
  • LocationType Bayfront
  • Address 24378 Deep Neck Rd
  • Bathroom 7

Deep Neck Farm - Beautiful 19th century farmhouse impeccably restored and updated with modern amenities and the recent addition of an open kitchen / family room with enormous views across the Choptank River to the Chesapeake Bay. On 15 acres with nearly 900 feet of secured waterfront this farm provides solace and privacy in a mature country setting. The house boasts ample room for extended family and guests with a large primary suite enjoying a waterside balcony, another large guest suite / studio with waterside balcony, a guest room with bath en-suite and three additional guest rooms. The historic wing of the residence is a step-in time with exposed beams in a den with adjoining screened porch and formal living and dining rooms with beautiful wood floors. The modern kitchen with large center isle opens to informal dining around and a casual waterside family room. There is another foyer leading to the guest suite / studio and mud room with laundry, walk-in wine cooler, two car garage and mechanical room. The grounds of Deep Neck Farm are tastefully simple and elegant. Mature landscaping with outdoor lighting and irrigation is manicured and kept to high standards. There is a dark gunite pool with outdoor shower, patio and immense western exposure taking in broad water views. The shoreline is secured with rip-rap and the pier provides over four feet at mean low tide and is equipped with boat and personal water craft lift. Deep Neck Farm is a unique opportunity for an Eastern Shore retreat providing the historic charm of traditional tidewater architecture with modern improvements sure to please the discerning buyer.

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

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$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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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6520 Swan Creek Rd Rock Hall MD 21661

Rock Hall, MD6520 Swan Creek Rd

Price$3,950,000

Est. Mortgage: $/month

MLS Number 1009997570

  • Single Family
  • LocationType Bayfront
  • Address 6520 Swan Creek Rd
  • Bathroom 7
  • Bedrooms 7

200K PRICE ADJUSTMENT! Amazing opportunity. Located on the Chesapeake Bay, Rock Hall Stud is a 240 acre property featuring a 12,520 SF unique, waterfront main residence built in 1986, swimming pool, private beach, stud farm with facilities, and beautiful private and sub-dividable acreage. An outside observation deck that spans the entire length of the home's copper roof boasts panoramic views of Bay Bridge and Baltimore skyline. Note: Photo #2 is a RENDERING of a possible renovation.

Listed by Maura F Shannon of TTR Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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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1965 Love Point Rd Stevensville MD 21666

Stevensville, MD1965 Love Point Rd

Price$3,399,000

Est. Mortgage: $/month

MLS Number MDQA140618

  • Single Family
  • LocationType Bayfront
  • Address 1965 Love Point Rd
  • Bathroom 7
  • Bedrooms 4

You pull into your long driveway, noticing as if for the first time the beauty that is the Chesapeake Bay in the distance. Your eyes quickly avert to the grandeur of the luxury estate that is your home. You remember that your family is home, eagerly waiting for your return. As you enter through your 11-foot steel doors, you take a deep breath and silently begin to take it all in, but quickly refocus. You find your favorite people relaxing in the private theatre room that is sure to be the envy of all that experience it. Soon after, more guests arrive, all in awe of the detail, the attention, the pure magnificence that is the space you are fortunate to call home. As you begin to tour your guests, each is astonished at all that your home is. All 18 of you settle in for dinner in your grand dining space, your private chef shares the particulars of the meal. After dinner, everyone heads to the rear patio and settles in around the fire pit with a glass of wine, some running through the expansive rear yard, waves crashing on the shoreline, in the distance the sun begins to set over the bay. The evening seems to be nearly perfect. Soon, those exhausted, find themselves back in the private theatre room, asleep to their favorite movie. Others full of love and peace, split up, some heading to the game room, others to the grand living room for conversation and laughs while the fire crackles in your carved stone fireplaces. As the evening comes to an end, you remember, you earned this, you deserve this, your life is what you dreamed it would become. Welcome Home.

Listed by Phillippe Gerdes of Long & Foster Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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 MDQA141708

  • Single Family
  • LocationType River
  • Bathroom 7
  • Bedrooms 6
  • Square Feet 8494

Amazing Kent Island Estate! The beautiful main house built in 1991 sits on 57+acres with 2,800 feet of water-frontage on Warehouse Creek. This 6 bedroom, 6.5 bath home is ready for you to make it your own. Enjoy the large attached 3 car garage as well as the beautiful 4 car carriage house. Oversized in ground pool. Perfect location for boating, fishing, and hunting. Only a few minutes to Chesapeake Bay by boat! The treasure of this property is the exquisite historic home built in 1700 and on the MD historical society list! Ideal for Wedding parties, Hunting groups, and vacationers who appreciate being in one of the oldest homes in Maryland. It is currently on Air BnB as a source for extra income. This charming historic house has 4 bedrooms and 3 bathrooms. Take advantage of the amazing potential this property offers for a Family, Wedding Venue, Retreat Center, or Equestrian estate. The opportunities are endless with this gorgeous estate abundant with wildlife, deer, and fowl and two private docks along with many acres of farm land. 3 Miles to the Chesapeake Bay Beach club and the Bay Bridge Airport.

Listed by Bret L Merson and VANCE WESLEY MERSON of Keller Williams Realty Centre

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$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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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7280 Swan Creek Rd Rock Hall MD 21661

Rock Hall, MD7280 Swan Creek Rd

Price$2,970,000

Est. Mortgage: $/month

MLS Number MDKE116788

  • Single Family
  • LocationType Bayfront
  • Address 7280 Swan Creek Rd
  • Bathroom 3
  • Bedrooms 3

"Gliding Gander Farm" Spectacular Chesapeake Bay waterfront farm with over 1/2 mile of protected shoreline with sandy beaches. Sunrises over the ponds & Sunsets over the bay. Rockfish out your front door and ducks and geese out your back door. 117.57 acres includes two (2) 10+ acres perced waterfront lots & one (1) Bay view lot. 100 acres of highly productive Mattapex soils with 3 ponds including well service. 2900 SF residence with 3 bedrooms & 3 full bathrooms with views to the Chesapeake from every room. 40 X 80 heated metal workshop for all your toys and more. We are following the COVID-19 guildlines issued by MAR.

Listed by Francis J Hickman and Richard C Evans of Cross Street Realtors LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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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24848 Deepwater Point Dr Saint Michaels MD 21663

MLS Number MDTA139294

  • Single Family
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 5406
  • Year Built 1985

Extraordinary panoramic views of the Miles River come with this Nantucket Cottage sited on 1.48 +/- acres. With over 400 feet of protected shoreline, with 8ft of MLW and an 8ft wide pier, 600 square foot viewing platform and 15,000 pound boat lift with remote. Enjoy the parade of boats on their way to St. Michaels Harbour, the Chesapeake Bay Maritime Museum, and the Miles River Yacht Club. Unobstructed view without trees or vegetation. Enter La Peniche to a warm open floor plan with stunning views from most rooms. Many renovations from 2008 until now. Low maintenance siding and Azek trim, gutter with leaf guards, remediated crawl space with drains, dry wells, and flood vents. Roof replace in 2019 with architectural shingles carrying a silver plate 50 year warranty with remaining transferable. ADT alarm system, whole house smart panel for dish TV, data, and telephone. 3 zones of heating and cooling, with heated floors throughout. 2 car garage plus work shop. With 720 square feet of heated and cooled space above with enclosed staircase, offering a myriad of uses. Located in the private community of Martingham, just 2 miles from historic St. Michaels. With a newly renovated 18 hole golf course designed by Pete Dye located within its bountaries. A truly a unique property with too may appointments and details to list. A MUST SEE!!!

Listed by Mary J Baker of Benson & Mangold, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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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26561 North Point Rd Easton MD 21601

Easton, MD26561 North Point Rd

Price$2,199,000

Est. Mortgage: $/month

MLS Number MDTA138940

  • Single Family
  • Address 26561 North Point Rd
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 5066

Beautiful Coastal style water front home, first time offered. In ground pool with hot tub. with custom pool deck. 2.89 acres of professionally maintained lawn and gardens. Off the Tred Avon river with access to Oxford and Chesapeake Bay. Very deep water at the private pier. Close to Easton and St. MIchaels in an estate development with SE exposure. Bonus room over the garage with full bath, main house with entrance foyer, dinning , living and family room. Eat in gourmet kitchen featuring granite counter tops. First floor master bed room and bath and large walk-in closet space. Second floor features three bed rooms two baths and a private office. Two car attached garage

Listed by Mark W Lappen of Meredith Fine Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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 2020 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 September 29, 2020. 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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