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Eastern Shore Luxury Homes for Sale

View all luxury homes for sale on the Eastern Shore of Maryland. These properties are priced at $1M and higher. You'll find a variety of beautiful high end homes on the Eastern Shore.

Maryland Luxury Real Estate Listings

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33376 Fox Road Easton MD 21601

Easton, MD33376 Fox Road

Price$4,750,000

Est. Mortgage: $/month

MLS Number MDTA2004342

  • Single Family
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 5,361
  • Acreage 437

Tamsey Farms offers over 400 acres with productive farm fields, mature woods, tidal marsh, elevated home site with a brick, two-story farmhouse, caretaker cottage, pole barns, sheds, workshop, pool and pier. Located at the confluence of Tuckahoe Creek and the Choptank River, this offering is sure to please with an abundance of wildlife habitat, privacy and the potential through a conservation easement for two additional residences. Two parcels are identified as 434 +/- acres just ten miles to Easton and eight miles to Denton. Photos of the residence as well as floorplan and 3-D Tour Coming Soon!

Listed by Coard A Benson of Benson & Mangold,LLC

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$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 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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13512 Yellow Banks Court Ocean City MD 21842

Ocean City, MD13512 Yellow Banks Court

Price$1,519,900

Est. Mortgage: $/month

MLS Number MDWO2011380

  • Single Family
  • Bedrooms 5
  • Bathroom 3
  • Square Feet 3,000
  • Acreage 0.14

You're going to want to see this elegant and fully-furnished luxury-waterfront home located just outside of Ocean City proper. These sellers lovingly upgraded every aspect of this home. Pay attention because no detail was overlooked. In essence, this home is as close to new construction as it can get. When you first arrive at this home you'll can appreciate the quality of the brand-new roof, new siding, new fascia and soffit, new energy efficient windows & Pella Sliders, new hvac systems and a newly conditioned crawlspace. As you enter into an open foyer with cathedral ceilings, complimented by timeless trim details on the walls, all new lighting, all new flooring, and so much more. Passing into the living room you'll notice the soaring tongue-and-groove ceilings complimented by recessed LED lighting, and stunning antique-style beams. The open floor-plan of the main living area boasts an array of windows overlooking the water, and an oversized dining room with room for all your family and friends. No expense was spared in the kitchen, with new cabinets, granite counter-tops and top-of-the-line appliances. The first floor owners-suite is as luxe as we've seen, with an expansive bedroom space overlooking the water, a spacious walk-in closet, and a on-suite bathroom worthy of it's own magazine spread. Simply put, the character, charm, and elegance this property exudes will be appreciated by those that have the opportunity to see it in person. *Fifth bedroom is a converted den/bonus-room over the garage. Saving the best for last, we'd be remiss to not mention that this home features a private bulkheaded dock and boat lift (large enough for the sellers 26' deep-v hull). The small HOA features a community pool, perfect for a refreshing dip on a hot summer day. This home has all the best features of both Fenwick Island and Ocean City MD, with easy and immediate access to both beaches residing less than a few blocks away.

Listed by Grant K Fritschle of Keller Williams Realty Delmarva

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$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 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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155 Old Wharf Road Ocean City MD 21842

Ocean City, MD155 Old Wharf Road

Price$1,220,000

Est. Mortgage: $/month

MLS Number MDWO2011426

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,002
  • Acreage 0.17

Relish in luxury as you sit on your expansive waterfront deck, shaded by a lovely pergola and soak in the relaxing sights and sounds of coastal living in this stunning Ocean City home. Improved with enchanting and tasteful elements, this 2-story home sits along a canal that provides quick and direct access to the Assawoman Bay. Thoughtful coastal details are carried throughout both the interior and exterior with fresh paint, decorative lighting, decorative moldings, and more. A welcoming foyer invites you in from the hot summer sun and opens to an airy floor plan that flows seamlessly from space to space and allows for ease of conversation and entertaining. A lovely living room welcomes family and friends in from the front door to engage in memorable conversation. Gourmet kitchen is equipped with granite counters, double wall oven, plenty of counter space, and a central entertainer's island hosting a breakfast bar and gas cooktop with griddle. Extraordinary solarium is embellished with T&G wood accented vault ceiling and multiple windows framing waterfront views. An en-suite bedroom and second bedroom are both present on the main level allowing for the opportunity for single-level living. A second full bath has been renovated with gorgeous marble shower surround and vanity. Ascending to the upper level along the stained wood and iron rod staircase, you are presented with high vaulted ceilings and a generous family room loft. This space is perfect for many different uses as a recreation room, movie room, and more. Escape your worries as you enter the gracious owner's suite oasis, crafted to facilitate relaxation and serenity. Soaring high ceilings, large walk-in closet, sitting area, and personal waterfront deck. Unwind and replenish in the lavish, spa-inspired full bath. A beautiful combination of sand tone tile, jetted soaking tub, and remarkable glass enclosed steam shower with seat make this the perfect getaway every day. An additional bedroom and full bath are also present on the upper level. An attached garage allows for additional space for useful storage or to become a flex space, as HVAC exists to condition the area. Gather with family and friends on the patio to enjoy the warmth of an evening fire or fish in the canal right from your back yard. New landscaping provides additional prestige to the exterior of this home. A multitude of upgrades are present throughout this home creating a delightful coastal sanctuary ready to welcome you home!

Listed by Tom Ruch of Northrop Realty

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$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 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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113 Prospect Bay Drive W Grasonville MD 21638

MLS Number MDQA2004996

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,071
  • Acreage 1.06

Beautiful waterfront property in Prospect Bay community. Four bedrooms plus potential for inlaw suite or second owners suite on the first level. Second floor deck with amazing views of the sunset. Calmer waters because you're in the boat basin marina without compromising the expansive waterfront views of Eastern Bay! Crawl space and two attics are encapsulated and heated . Irrigation system. Wood burning stove and open floorplan ideal for entertaining. Fabulous Community of Prospect Bay Golf & Country Club! A beautiful 18 hole golf course, golf shop, driving range & putting green, swimming pool, lighted tennis & pickle ball courts, marina, boat ramp, children's playground, and a 12,000 square foot Club House that includes a restaurant & bar! Only 15 min to the Bay Bridge! Welcome Home.

Listed by Biana J Arentz of Coldwell Banker Realty

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Federal 30-year interest rate: 6.49% last updated on Dec 1, 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 Drive Saint Michaels MD 21663

Saint Michaels, MD7751 Rollyston Drive

Price$12,500,000

Est. Mortgage: $/month

MLS Number MDTA2004414

  • Single Family
  • Bedrooms 9
  • Bathroom 13
  • Square Feet 13,617
  • Acreage 91.19

Arguably one of the most important new builds on the Eastern Shore, 7751 Rollyston Drive is a 91-acre estate on two parcels with 1500 feet of shoreline along a wide stretch of the beautiful Miles River. This turnkey property, just outside the town of St. Michaels, was completed in 2016. Prioritizing waterfront views, outdoor living spaces and comfortable living as well as for entertaining guests, the stately main house is accessed by a private, pea gravel road bordered by a pond with two gazebos and lighted fountains. The graceful circular driveway can accommodate multiple vehicles and leads to the rear entrance of the 4-car garage. The main residence with 12' to 14' ceilings offers 9 bedrooms with ensuite baths and 4 half baths. Accessible from the second floor of the main house as well as the garage, a stand-alone apartment showcases a great room with cathedral ceiling, pool table and game table with refreshment center, sound system, bedroom, and 1 ½ baths. Two outdoor porches are perfect for dining and entertaining and a porch off the second floor Primary Suite offers spectacular river views. Built by a prominent DC builder for his own personal use, the structure of the house is truly commercial- grade and no detail was spared. All carpentry and flooring were custom designed and built with unparalleled craftsmanship, as evidenced by the moldings, staircases, and woodwork throughout the residence. Baths are Waterworks with marble tops and hardware is Baldwin Satin nickel. Media, HVAC, outdoor lighting, and security systems are controlled remotely through apps. Designed with an eye to entertaining there is a room for every occasion: a large eat-in Gourmet kitchen with granite countertops and Wolf/Sub-Zero appliances; a formal dining room that comfortably seats 14, two offices, a cozy family room with adjacent bar and living room, and a main level full bedroom with ensuite bath. Additionally, there is a Media room with 12 theater chairs, full bar, spa room and a large multi-purpose room in the lower level. Outdoors, a flagstone path leads from the southern side porch to a heated salt-water pool, pool house with two full baths, a covered outdoor kitchen and dining area with Wolf/Sub Zero appliances, and a 100” pier. The property houses a climate-controlled barn with plumbing, potential for 10 horse stalls and a second- floor hay loft or, the entire structure can become a car collector's paradise. Next to the barn is a paddock and further down a service road is a cleared area for a future tennis/sport court. The caretaker's house at the entry to the private drive has two levels, front and rear porches, three bedrooms, three and one-half baths and a two-car garage with two outdoor spaces. When the current owners built the property, the expansive view of the Miles River became the focal point of the interior public rooms and now provides exquisite sunrise views. The partially rip-rapped shoreline has a small beach accessible by canoe, kayak, or shallow water boat. Co-Lister includes Cynthia Howar.

Listed by Thomas A Keane and Marc Bertinelli of Washington Fine Properties,LLC

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$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 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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3896 Eastern Neck Road Rock Hall MD 21661

Rock Hall, MD3896 Eastern Neck Road

Price$1,300,000

Est. Mortgage: $/month

MLS Number MDKE2002162

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,792
  • Acreage 1.02

Spectacular Bayfront with clear, uncompromising views. Hard to find one-floor-design, and completely out of the flood zone. Wake up to the sparkling bay views every day in the beautiful primary bedroom. Views from all rooms. There is a family room with a rustic lodge feel, incorporating the charm of the original cottage, and spacious decking surrounding the house. The perfect place for coffee, a cocktail, catching bay breezes and watching the sunset. Only minutes into downtown Rock Hall with it's charming Main Street, coffee shop, jazz and blues venue, restaurants, and many marinas. Just under two hours to Philadelphia, Baltimore, DC, Wilmington and South Jersey. Make an appointment soon to see this one.

Listed by Lynn M Hilfiker of Gunther-McClary Real Estate

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$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 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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8533 Deep Cove Road Easton MD 21601

Easton, MD8533 Deep Cove Road

Price$3,295,000

Est. Mortgage: $/month

Pending

MLS Number MDTA2004400

  • Single Family
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 5,345
  • Acreage 5.28

Stunning open floor plan living, fabulous screened porch, large water side deck, second floor balcony. Inground pool with electric cover, small pool house and a large barn workshop/artist studio Property subject to a right of way.

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

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$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 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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13129 Cherry Lane Queen Anne MD 21657

Queen Anne, MD13129 Cherry Lane

Price$1,445,000

Est. Mortgage: $/month

MLS Number MDCM2002454

  • Single Family
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4,430
  • Acreage 39.27

Almost 40 Acres nestled in a serene setting in the quaint town of Queen Anne, and just around the corner from amenity-rich Tuckahoe State Park, this 5 bedroom, 4.5 bath Custom Farmhouse Retreat boasts scenic views from every room. Upon entry of the 4400+ sq. ft. home, the open concept Living room, Dining room, and Kitchen flow toward a Screened-in Porch overlooking the Gunite Pool and beautifully landscaped grounds. Upstairs in the Main House are three additional Bedrooms and another full Bath. The main level also consists of an expansive Family room with cathedral ceilings and a free-standing Wood Stove, a Primary Suite with a luxurious Bath, a huge Walk-in Closet, a Private Office, and Loft Space. Above the oversized attached 2 Car Garage, is an In-Law Suite with a Bedroom, full Bath, Living room, and Kitchen, complete with a Separate Entrance and Screened Porch. Overlooking the 33,000-gallon Saltwater Pool is a Pool House with Kitchenette, Full Bathroom, Screened Porch, Outdoor Shower, and Storage Area surrounded by lush Landscaping and a spacious Pool Deck, making this home the ideal place to entertain guests. The Backyard also has a detached Barn with 2 stalls, a Run-In shed, and 2 other separate storage areas. With the adjoining lot, this property boasts 39.27 acres of privacy combined with fishing, boating, riding, hiking, skill course, camping, Adkins Arboretum, and biking in Tuckahoe State Park providing countless ways to enjoy Maryland's natural environment. This fantastic property is within an hour's commute to Baltimore, DC, and Rehoboth! Don't miss this opportunity to make this amazing Retreat your own! HOME IS ALSO LISTED SEPARATELY. SEE MLS #MDCM2002082 and See the Farm Listing #MDCM2002474

Listed by Travis O Gray and Tonia M Falkowski of Engel & Volkers Annapolis

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$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 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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7332 Pea Neck Road Saint Michaels MD 21663

Saint Michaels, MD7332 Pea Neck Road

Price$2,500,000

Est. Mortgage: $/month

Pending

MLS Number MDTA2004366

  • Single Family
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 3,200
  • Acreage 2.88

This may be the most attractive home you have seen in a long time. Architect-designed and built to the highest standards in 2013, it is artfully proportioned, oriented to southerly and westerly views over Barrett Cove, and outfitted with high end appliances and every am.enity for the comfort of both owners and guests. The 3200 +/- sq. ft. main house is augmented by a charming guest cottage. *** The location puts you right next to St. Michaels and an unimpeded 20-minute drive to Easton. *** Entertaining is a pleasure with a flowing floor plan that leads from the gracious entry hall to the water-facing living room and adjacent dining room, and decks beyond. The 18 x 24 sq ft gourmet kitchen is a chef's delight with silestone quartz countertops, Wolf oven, warming oven, microwave and gas range-top, two refrigerators (one in the butler's pantry), custom cabinets, instant hot water, trash compacter, and a monorail lighting system. There are four gas fireplaces in the house -- in the family room/den, in the sun room, the living room, and outdoors on the wrap-around deck. Ceilings are high, inspired by a converted barn that was once the owner's home; most floors are sawn white oak save the Bluestone floor in the Sunroom. Windows and doors are Kolbe. The primary bedroom has its own water views, a private deck steps from the pool and a sumptuous bathroom with heated floor. The secondary bedroom is en suite and can double as office. *** The cottage completes the offering with a bright living room, good bedroom space, bathroom and kitchenette. Close by is the gunite pool, a private oasis set amid professionally designed gardens, hardscaping and woods where colorful camelias grow. The recently renovated two-car garage provides workshop space, and the double circle driveway handles parking for many vehicles. The pier sports a gazebo, has water and electricity and a boat lift, with spaces for two boats. The shoreline is protected with a Living Shoreline/Riprap combination. *** Note that the Tax Assessor's information is incorrect - the building referred to was lost in a fire, then replaced with the house described here. A survey gives the parcel 2.88 Acres. PLEASE DO NOT ENTER THE PROPERTY WITHOUT APPOINTMENT.

Listed by Anna C Larkin of Benson & Mangold,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 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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26561 N Point Road Easton MD 21601

Easton, MD26561 N Point Road

Price$2,800,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDTA2004384

  • Single Family
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4,816
  • Acreage 2.89

Stunning waterfront ideally located in estate area between Easton and St. Michaels. Minutes by boat to historic Oxford for dinner and the Choptank River for fishing. Easy drive to St. Michaels for fun and festivals. Saltwater gunnite pool, hot tub, separate guest suite, gourmet kitchen with quartz counters, farm sink and hardwood flooring. Primary bedroom is on the main level with completely renovated primary bath, lovely soaking tub with waterviews. This is the perfect house for entertaining. Gas fireplace in the living room and in the family room. Just off the Tred Avon river this property has Southwesterly views

Listed by Margaret W Moran of Long & Foster Real Estate,Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 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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12922 Riggin Ridge Road Ocean City MD 21842

Ocean City, MD12922 Riggin Ridge Road

Price$1,199,000

Est. Mortgage: $/month

MLS Number MDWO2011226

  • Single Family
  • Bedrooms 4
  • Bathroom 6
  • Square Feet 3,236
  • Acreage 0.3

Steps out of Coastal Living Magazine... Spectacular sunsets over the Marshes and water of the Assawoman Bay. Almost new construction, this home was designed, crafted and built by a sought after local custom builder. Hand cut and stained pine flooring throughout Living area with vaulted ceilings and high windows. Remarkable chefs kitchen with Stainless appliances including separate built in ice maker,gas cooking, solid surface coastal counters, white 42" cabinets with glass accents. An in -in law style wing with guest bedrooms, living area with custom pine floors, coffered ceilings, kitchenette with one of a kind granite counter. Fully tiled showers with designer insets, granite counters, double vanities and walk in closets.. Owners suite with soaking tub, marble surround and marble double vanity countertop, tile shower and walk in closets. No detail overturned with coastal flared lighting fixtures and more.. 2 exterior decks with private marsh views- maintenance free decking material with uniquely designed floating exterior staircase. Enjoy all season ambiance with a two sided fireplace from living room to deck. Built -in cabinet for outdoor entertainment. Oversized attached 2 car garage with epoxy flooring in addition to a detached 2 car garage with 100 amp service. 12 ft ceilings on each level of this home. Impact rated windows, tankless hot water heater, gas rough in for grill on outside deck. CertainTeed t-45 siding and 30 year architectural roofing shingle. Enjoy all that West Ocean City has to offer with the local favorites for restaurants, shopping and watersports yet tucked away with beautiful marsh views. Additional Upgrades: Under cabinet & above cabinet lighting in kitchen, foam insulation in 2 x 6 outer walls, Wolfe composite decking, tongue & groove ceilings on deck ceilings, hurricane impact windows, upgraded premium siding, recessed lighting throughout the entire home, Christmas lighting package, outdoor propane hook up for a grill on top deck, set up for outdoor TVs on decks & outdoor shower. (Custom bar is excluded) Now is the time to "Invest In The Beach Lifestyle"

Listed by R. Erik Windrow of Keller Williams Realty Delmarva

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$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 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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12304 Coastal Highway Ocean City MD 21842

Ocean City, MD12304 Coastal Highway

Price$1,590,000

Est. Mortgage: $/month

MLS Number MDWO2011202

  • Single Family
  • Bedrooms 8
  • Bathroom 4
  • Square Feet 2,912
  • Acreage 0.23

This 4 unit building and additional lot are ready to go with everything being completely remodeled down to the studs and the electric all the way from the pole. New roof, siding, windows and doors were placed on the outside and the stairs were rebuilt to accommodate additional storage for each unit. Three head split units keep the temperature at your demand and a surrounding fence and storage unit makes the property very easy to manage. Continue to rent out this income producing property through 2023 as per the contract, but then use the unit at your leisure. Better yet, purchase the property as a primary residence, and let three additional units pay your mortgage. One day in the future, you can build an additional two units even with a garage underneath on the addition lot that is part of the sale. Possibilities are endless. Professional Photos to come

Listed by Shawn Kotwica of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 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 December 8, 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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