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Chesapeake Bay Waterfront Homes for Sale

Waterfront Home in MarylandMany of the waterfront homes on Chesapeake Bay offer spectacular views of some of the best sunsets on the Eastern Shore. Whether you’re looking for Chesapeake Bay real estate with panoramic views, serenity, acreage, private dock, bayside deck, or all of the above, you’ll find a variety of waterfront homes to choose from. Discover the latest Chesapeake Bay homes for sale right here! You may also want to view all Eastern Shore waterfront homes for sale.

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4906 David Greene Road Cambridge MD 21613

Cambridge, MD4906 David Greene Road

Price$549,000

Est. Mortgage: $/month

MLS Number MDDO2003792

  • Single Family
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 1,200
  • Acreage 1.3

Discover Your paradise in the "Heart of the Chesapeake! You will feel peace and tranquility at this waterside home nestled on the shores of Fishing Creek, a tributary off of the Little Choptank River in Dorchester County, known for its rich history and natural beauty. The area provides activities for everyone's enjoyment so get out and explore the great outdoors! Stretching out 125 feet over the creek with 3-5' of water is the pier that will excite any boater enthusiast. It features water/electric/lights/a fish cleaning station and is outfitted with 4 boat lifts....a 10,000 lb., a 20,000 lb., a lift for a skiff and a lift for a jet ski. The Chesapeake Bay is just a 10 minute boat cruise giving access to the bountiful fishing grounds best known for it's rock fish, blue's, cobia and mackerel.. Tie your crab pot to the pier or learn to "trot-line" and catch fresh Maryland blue crabs. There's nothin' like 'em! A sandy beach is a rare feature of the landscape at this extraordinary retreat. Build sandcastles with the kids, float on rafts, swim, enjoy a good book, launch a kayak or canoe, your family dog will love it too! Afterward, rinse off in the outdoor shower and unwind in the hot tub. The turnkey cottage is tucked away on a large lot with expansive south westerly views, you'll love the feel of the breezes. The home provides an open concept living/dining/kitchen plan allowing the entire family to share time together. Plenty of bedroom space and 2 full bathrooms easily accommodate your crew. Hang out in the 40' screened porch--it's the perfect space to have a feast of fresh caught crabs and fish from the day with all of your favorite trimmings. Play games, do puzzles, laugh and create special memories. Bike riding and late afternoon walks are healthy activities to experience in the neighborhood abundant with wildlife...you're likely to spot deer, turkey, fox, Delmarva Fox squirrels, countless species of birds...endless possibilities. After a fun day on the water with a "belly full" grab a refreshing drink, head for the beach, gather 'round to relax and watch the sky turn magnificent shades of pinks, yellows, orange & reds, purple & blues as the sun tucks itself in over the horizon. It's truly a magical time of day. Enjoy the benefit of the extensive renovations to surrounding properties located in this quant Eastern Shore community. The perfect mixture of traditional and contemporary, where older homes are expanding with modern improvements. The property is centrally located within a short drive to Annapolis, BWI Airport and the MD/DE Beaches. Currently, enrolled in VRBO. Income generated generously offsets property taxes, insurances, mortgage, maintenance & improvements. For details please talk with listing agent. Don't delay scheduling a preview of your future paradise!

Listed by Rhonda L Richardson of Charles C. Powell,Inc. Realtors

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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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9088 Point Lane Chestertown MD 21620

Chestertown, MD9088 Point Lane

Price$1,100,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDKE2002104

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,426
  • Acreage 1.28

Spectacular sunsets guaranteed with panoramic views of the Chesapeake Bay. Eastern shore waterfront home features gourmet kitchen , outdoor pergola, updated bedrooms and baths, waterside deck , new roofing, outdoor waterfront porch, wet bar, and multiple zones for heating and cooling. Close proximity to Philadelphia and Baltimore/DC metro area make it a perfect weekend get away. Enjoy scenic Chestertown and the quaint town of Rock Hall and the bounties they have to offer. Abundant marinas and restaurants are near by . Relax with your morning cup of coffee watching the cargo ships ply the bay in the comfort of your sunroom. Take a tour of the local art galleries, shops and taste the bays bounty at local culinary establishments. This secluded home offers peace and serenity. Call today to schedule a viewing.

Listed by Kenneth J Roderick and Amy L Larrauri of RE/MAX Executive

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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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901 Marion Quimby Drive Stevensville MD 21666
Pending

MLS Number MDQA2005166

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 1,789

Welcome to 901 Marion Quimby Drive. The pictures don't do the views justice! Schedule your private showing, step inside and be prepared to fall in love with this Artist's Waterfront Retreat. The details found throughout the 1800 sq ft of living space including the walls of windows, built in bookshelves and hardwood floors enhance the charm of this home and the updates are sure to make you swoon. The open concept of the main floor allows you to admire the southwest views from every room. Or use the slider to your private balcony to enjoy your morning coffee or afternoon beverage while watching the sunset. There is a full bath, guest room and laundry on the main level. The second floor boasts two suites each with walk in closet and en suite. One currently used as an art studio has a it's own private waterfront balcony and updated en suite with floor to ceiling tile walk in shower and double vanity. All of this just steps away from the waterline of Thompson creek - 2 Kayaks convey! Watch the wildlife, birds and boaters alike all from the comfort of your own piece of paradise. Thompson Creek Condos is a water front community with a pier, clubhouse, pool, tennis courts and walking path all just minutes from shopping, dining and the Chesapeake Bay Bridge. Escape the city and exhale on Kent Island. *May be sold furnished.

Listed by Kathleen M Higginbotham of Keller Williams Flagship of Maryland

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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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5738 Beach Road Rock Hall MD 21661

Rock Hall, MD5738 Beach Road

Price$800,000

Est. Mortgage: $/month

MLS Number MDKE2002020

  • Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,819
  • Acreage 0.96

A rare offering of an in-town waterfront parcel offering incomparable views from a point of land on the Chesapeake Bay. The house is valuable for the large footprint it provides (would not be able to build at this size on this lot otherwise. ). Town water and sewer, the public beach just steps away, sunsets and the sparkling Bay at your door. House needs extensive renovation and you will be required to build first level to higher flood code regulations. renovation permits/regulations need to be verified with the Town of Rock Hall by the Buyer.

Listed by Lynn M Hilfiker of Gunther-McClary Real Estate

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$
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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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9806 Martingham Circle Saint Michaels MD 21663

MLS Number MDTA2004178

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2,517
  • Acreage 2.34

Looking for that special waterfront ? Look no further! This one's been waiting for you. Breathtaking views of Hambleton Cove out to the Miles River. This home offers easy one level living and is situated on 2.34 +/- acres. Don't miss your chance to own a home that is ideally accessible by land and boat to the very best the Eastern Shore has to offer. The community of Martingham is located on the Miles River and the Chesapeake Bay, just over a mile from historic St. Michaels where you will find great restaurants, shops, the Chesapeake Maritime Museum and so much more. The views from this home are stunning from the minute you walk through the front door. The floorplan is open and bright offering walls of windows, vaulted ceilings and one of a kind views from many of the rooms. This home features 4 spacious bedrooms and 3 ½ baths. You will have your choice of 2 primary bedrooms, one bedroom features a magnificent water view, large deck, hardwood floors, a full bath with dual vanities, spacious shower and walk in closet. The 2nd choice for a primary bedroom offers hardwood floors, full bathroom with vaulted ceiling, dual vanity, large, jetted corner tub and separate water closet. Two additional spacious bedrooms offer hardwood floors and plenty of closet space. One of your favorite spots in this home will surely be the sunroom offering panoramic views of Hambleton Cove that extend far beyond to the Miles River. The outdoor space is expansive with two large decks, a beautiful paver patio surrounding a Gunite inground pool. The pool is heated which allows you to extend the summer season. A few other noteworthy features are new HVAC in 2019, Pool replastered and new coping in 2016, washer/dryer 2020, crawl space encapsulated with dehumidifier, gas grill attached to propane gas line, partially floored attic space over garage and primary bedroom. central vac, fireplace in family room, storage shed, large private laundry room with lots of storage and utility sink. The pier features a 6500lb Magnum boat lift and two jet ski lifts with plenty of water depth for all. MLW estimated at 3 to 4 ft. From the moment you drive in, your greeted by serene elegance , surrounding you with mature trees, abundant wildlife and a premiere golf course that meanders through this prestigious , well-established community. This home and property are all about relaxing and enjoying the peaceful life on the Eastern Shore. If you are a golfer join the private 18 hole Links at Perry Cabin, designed by the highly renowned Pete Dye. Membership to the Links at Perry Cabin also gives you access to some of the amenities of the exclusive and historic Perry Cabin Inn. Take a quick ride into nearby historic St. Michaels or the charming town of Oxford. This is a very special location, community, home and property.

Listed by Terri L Murray of RE/MAX Executive

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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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100 Tred Avon Avenue Oxford MD 21654

Oxford, MD100 Tred Avon Avenue

Price$2,500,000

Est. Mortgage: $/month

Pending

MLS Number MDTA2003742

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 3,715
  • Acreage 0.3

Historic Oxford - Spectacular home on one of the quietest streets in Oxford. Very peaceful yet close to all that Oxford offers. Western Exposure offering expansive sunset views from Primary Bedroom, living room and sun room. Views across the Tred Avon River, Choptank River and the Chesapeake Bay. First floor primary suite, great room with beamed cathedral ceiling, gourmet kitchen, sunroom with incredible views, 1 car garage and second floor waterfront deck. Deepwater dock with 18,000 lb. lift. This house is truly one of a kind!

Listed by Henry S Hale of Benson & Mangold,LLC

$
$
%
$/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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7722 Latchstring Lane Bozman MD 21612

Bozman, MD7722 Latchstring Lane

Price$744,000

Est. Mortgage: $/month

Open House

MLS Number MDTA2004100

  • Single Family
  • Next Open House: Sat 12/10 10:00 am. to 2:30 pm.
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,344

You don't want to miss this charming turnkey 3 bedroom, 2 bath WATERFRONT home on Grace Creek. Sit, relax, and take in the amazing water views and sunsets from your back deck or private dock. This turnkey home has been updated with new bamboo wood floors, updated master bath, all new exterior and interior paint, new interior doors, and much more. Enjoy crabbing and fishing from your private dock with boat lift. Easy access to the Chesapeake Bay. Lots of room for outside entertainment. Minutes to downtown St. Michaels with fabulous restaurants, shopping and entertainment.

Listed by Sharon Fisher of Coldwell Banker Chesapeake Real Estate Company

$
$
%
$/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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106 Tred Avon Avenue Oxford MD 21654

Oxford, MD106 Tred Avon Avenue

Price$3,000,000

Est. Mortgage: $/month

MLS Number MDTA2004024

  • Single Family
  • Bedrooms 6
  • Bathroom 5
  • Square Feet 4,293
  • Acreage 0.4

This remarkable waterfront property with a large waterside concrete pool within 25' of the Tred Avon River and looks west over the river and across the Chesapeake Bay. Pier with lift, rip-rapped shoreline and southwest breezes and sunsets year round. Located in the heart of Oxford's Historic District. Tree-lined streets on two sides, private, fenced and landscaped.

Listed by Ray R Stevens of Benson & Mangold,LLC

$
$
%
$/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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4699 World Farm Road Oxford MD 21654

Oxford, MD4699 World Farm Road

Price$2,995,000

Est. Mortgage: $/month

MLS Number MDTA2004046

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 5,004
  • Acreage 9.01

Bright, sunny house with panoramic views of Island Creek. Very private setting. House appears bluish color in pix, but in fact is a deep gray color. You can paint the house any color you like. 9.01 acres (approx 2 acre homesite, 1 acre woods, 6 acres agriculture) off Rt.333 ("the Oxford Road"). Field currently planted in soy beans but is ideal for horse pasture. Oxford 3 miles; Easton 7 miles One of the finest points of land in Oxford Neck. High ground with well drained soil. 1000 feet of shoreline, mostly rip-rapped, on Island Creek, with quick access to the mouths of the Choptank and Tred Avon Rivers and the Chesapeake Bay beyond. Eastern, southern and southwestern exposures. Sunrises and winter sunsets over the water. Bailey dock with 6 to 8 ft MLW. Controlling depth at the mouth Island Creek is 6 ft mlw Residence: ---designed by Margaret M. Garey, AIA, taking advantage of the 180 degree water views. --- built in 1987 by Lloyd H. "Bill" Fleming Heated living area 5,004 square feet. Garage 809 sq ft; decks 932 sq ft Redwood and Hardy-plank siding. Oak floors in foyer, hallways, dining room, den. Living Room has two-story ceiling and French doors opening onto 15 x 15 deck, plus 4 x 20 wrap-around deck Den has ca. 1830 mantel from “Ashland Farm”; bi-fold doors open to Living Room; shelves around the room; bookcases over cupboards flank the fireplace. Dining Room with French doors leading to 20 x 4 deck. Crystal chandelier. Bi-fold doors can close off dining room from living room. Oversize two-car Garage with electric door (remotes), recently drywalled and painted. Work bench. Master electric panel/breaker box. Access to crawlspace. Crawlspace has poured concrete floor. Pull-down steps to storage over Garage. Roof replaced ca. 2014 House has gutters and downspouts Marvin thermopane casement windows Utilities: Heat and cooling by three heat pumps Electric: Delmarva Power. Television: by satellite (former owner had “Dish TV“) Internet: Unknown. Probably WiFi Shannahan artesian well. Septic system approved for a 4 bedroom house. Has been pumped on a regular basis.

Listed by Robert G Shannahan of Shoreline 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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3019 Bennett Point Road Queenstown MD 21658

Queenstown, MD3019 Bennett Point Road

Price$3,745,000

Est. Mortgage: $/month

MLS Number MDQA2004720

  • Single Family
  • Bedrooms 7
  • Bathroom 9
  • Square Feet 10,000
  • Acreage 5.71

Spectacular contemporary waterfront estate on 5.7+ private acres with 250 +/- feet of rip rapped waterfrontage on the Wye River. Situated in the private and exclusive Bennett Point peninsula, the home offers stunning water views of the Wye River to the east and the Chesapeake Bay to the west. Highlights include approximately 11,000+/- sq.ft of living space, 7 Bedrooms, 8.5 updated Baths, indoor salt-water pool, elevator, rear trex-type deck, tennis court with gazebo, treehouse, 2-car attached garage, pier with 2 boat lifts and slips, and updates throughout. The main level features a sunbathed open floor plan foyer, leading directly to the dining room and grand living room with wood burning fireplace and multiple exposures overlooking the water. The updated gourmet eat-in kitchen with breakfast area offers large island with bar seating, Thermador & Viking stainless steel appliances, granite topped counters, sitting area, and a walk-in pantry. Off the kitchen are 3 bedrooms, 1 with ensuite bathroom, and an additional bathroom. The main level is completed by his & her office, screened front porch, powder room, elevator to 3 levels, saltwater pool with desert air climate control & retractable cover, walk-in sauna & full bathroom, laundry, and large 2-car garage. The second level offers the primary suite, 3 additional bedrooms with ensuite bathrooms, laundry room, balcony overlooking the Wye, open exercise area, and elevator access. The large primary suite has a gas fireplace, two large walk-in closets and direct access to the laundry. The upgraded luxurious primary bathroom features a double vanity, separate seamless glass shower, free standing tub, powder room, and access via double doors to a large balcony overlooking the rear yard and Wye River. The 3rd level offers a large crow's nest with wet bar and is a perfect spot to enjoy 360-degree views east across the Wye River towards the Wye River Nature Preserve, south down Bennett Point, and west to the Eastern Bay. The main house is completed by a full lower level with access via staircase, elevator, and walk-out stairs. Offering a theater room, game area with wet bar and dishwasher, billiard area, bonus room that can be used as a bedroom, full bathroom, and ample storage. Set on 5.7+ acres the private property features mature landscaping, a first-class tennis/pickle ball court with a new screened gazebo, hot tub, tree house, redone dock with two lifts (25,000lbs, 1,500lbs) and a paddle board launching float, paddle board rack, natural shoreline. Easy access to Washington DC, Annapolis, Easton, St. Michael, Baltimore, 2 Hours from Philadelphia, and less than 4 hours from New York City. All interion/exterior furnishings available for purchase separately.

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

$
$
%
$/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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922 Waterview Drive Crownsville MD 21032

Crownsville, MD922 Waterview Drive

Price$1,350,500

Est. Mortgage: $/month

Active With Contract

MLS Number MDAA2039330

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,600
  • Acreage 0.34

SEVERN RIVER WATERFRONT! Exceptional Quality! To-Be-Built Custom Waterfront Coastal Farmhouse presented by Whitehall Building & Co. Open layout with expansive views overlooking the Severn River on every level. Spacious 4bed/3.5 bath 3600sq' home with upgraded standard features including Hardiplank siding, two-car garage, 9' ceilings, wood floors, ceramic tile in baths, granite countertops, SS kitchen appliances, 42" soft close custom Shaker kitchen cabinets, two-zone heating & cooling, upper-level laundry center, fully finished lower level with 4th bedroom, 3rd full bath & recreational space -great for entertaining friends and family on the water! The list price also includes an allowance for a new pier! Build at the base price with the standard floor plan options, or elevate your dream home finishes; buyers' custom selections/upgrades are welcome! Buyers must be pre-qualified before meeting with the Builder at the property. $10,000 credit toward buyer selections when you use one of the Builder's preferred construction-perm financing lenders and title company. Note: The interior photos in the listing are representative of other houses completed by this builder. Visit whitehallbuilding site for further information about the Builder. Convenient to DC/Balt/Annapolis/NoVA. Easy marine access along the Severn River, the Chesapeake Bay, and all surrounding waterways.

Listed by Arian Sargent Lucas and Julie C Knott of Lofgren-Sargent Real Estate

$
$
%
$/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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3509 Greenpoint Road East New Market MD 21631

MLS Number MDDO2002832

  • Single Family
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 2,466
  • Acreage 0.26

One-of-a-kind Multi-Residential property with a private deep water marina nestled at the end of Green Point on the Choptank River! Whether you are looking for an investment, new business venture, weekend getaway or family compound, this property offers something for everyone! The secluded waterfront dwelling is surrounded by water, nature, and wildlife. Enjoy stunning sunsets from your porch and catch fresh seafood, crabs, and oysters from your dock. Explore the Choptank River from private launch via canoe, kayak, or jet ski. A quick boat ride will take you to nearby towns | attractions like Oxford and Saint Michaels, or The Hyatt Regency Chesapeake Bay and Suicide Bridge Restaurant. Enjoy all the Eastern Shore has to offer from your backyard! Coastal cape cod has been freshly painted and offers 2B | 1BA. Recent improvements include a new roof & well, LVP flooring, and updated appliances and fixtures. The Guest cottage offers an additional 1B | 1Ba with living space, kitchen, and screened-in porch! With a little tlc this would make a fantastic home office or lucrative short term rental! Protected marina offers a 14-ft concrete ramp, 2-electric boat lifts, 6 additional tie-up slips, running water and electric, and offshore duck blind. The main dock and pier have been completely replaced (2021). RV's welcome with (2) 50-amp hookups! Rare opportunity to establish yourself in the Seafood industry, personally enjoy, or create something new!

Listed by Katie Marie Lowry 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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