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Oakland MD Real Estate

Browse the latest real estate listings in Oakland MD below. You may also be interested in viewing available real estate in other Caroline County towns.

Oakland Real Estate for Sale

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199 Gnegy Church Road Oakland MD 21550

Oakland, MD199 Gnegy Church Road

Price$169,900

Est. Mortgage: $/month

MLS Number MDGA2004210

  • Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,680
  • Acreage 0.99

Charming farm style rancher located in the rolling hills of Southern Garrett County! This 3 Bed, 2 Bath single story home is conveniently located 15 minutes from downtown Oakland with lots of restaurants and shopping, and just 25 minutes from all the amenities at Deep Creek Lake. All newer flooring with modern kitchens and bathrooms. Covered porch to relax and soak in the rolling pasture views. Walk-out unfinished basement is perfect for a workshop and to store all your tools. Level one acre lot and large patio provide plenty of space for outdoor entertaining and activities. Call today for your private showing

Listed by Jonathan D Bell of Railey Realty,Inc.

$
$
%
$/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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86 Tarn Drive Oakland MD 21550

Oakland, MD86 Tarn Drive

Price$79,900

Est. Mortgage: $/month

MLS Number MDGA2004226

  • Land
  • Association Name MOUNTAINSIDE

Welcome to Mountainside at Deep Creek Lake. Build your dream home on one of the largest, forested lots remaining in this preferred Deep Creek Community of 137 paved lots on the Mountain. Mountainside offers a lake front Marina Clubhouse as well as private Tennis and Pickle Ball Courts and a picnic pavilion on the Mountain. The Marina Clubhouse has a pool table, game tables, conversation area w/fireplace, small kitchenette, lakeside deck with dining tables and opportunity to store your inflatables and kayaks on the lower level. This lot has "A Class" ownership which allows the owner to participate with a limited number of other A owners in an annual lottery to lease one of 9 boat slips at the Mountainside Docks. Deep Creek lake allows power boats, jet skis, kayaks and fishing. Your new Mountain retreat will be minutes away from the Wisp 4-Season Resort with snow skiing & tubing, golf, mountain bike riding, confidence course and more. The U.S. Kayak Olympic Training facility is at the top of Wisp Mountain and is open to the public for white water rafting. Take your friends and family to Swallow Falls State Park where you will find not one, but 3 separate waterfalls, including Muddy Falls, Maryland's largest waterfall. The next day, take them to Deep Creek State Park for trails, nature center and sand beach, then enjoy an evening meal at one of the many dining opportunities at Deep Creek Lake. Oakland, the County Seat, boasts a Hospital, more dining opportunities, many small retailers and a Walmart.

Listed by Jonathan S Lahey and Richard E. Saunders of EXP Realty,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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2816 Steyer Mine Road Oakland MD 21550

Oakland, MD2816 Steyer Mine Road

Price$500,000

Est. Mortgage: $/month

MLS Number MDGA2004214

  • Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,534
  • Acreage 103.93

103 Acre Hunters and Fisherman's Paradise! Property is improved with a 3 bedroom/2 bathroom double wide mobile home with an attached 2-car oversized garage and an unfinished basement for storage. Also included are a barn and a hunting cabin. Laurel RunTrout Stream runs through the property. Raspberry and blackberry bushes are planted throughout the property, as well as apple and peach trees. This property is secluded enough to forget about the craziness of busy life yet still only minutes away from Deep Creek Lake activities and Oakland shopping.

Listed by Justin D Liller of Railey Realty,Inc.

$
$
%
$/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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Lot 6 Hoye Crest Road Oakland MD 21550

Oakland, MDLot 6 Hoye Crest Road

Price$44,900

Est. Mortgage: $/month

MLS Number MDGA2004192

  • Land

Opportunity to own over 6 acres on Backbone Mountain adjoining the Highest Point in Maryland! This lot will offer some of the best views from Maryland's highest point with western exposure. Approved perc and electric on site . Ready for you to build your dream home! Lots in this community have been selling fast. Call today to claim this one before it sells too!

Listed by Nick Fratz-Orr of Railey Realty,Inc.

$
$
%
$/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 Mountainview Court Oakland MD 21550

Oakland, MD113 Mountainview Court

Price$759,900

Est. Mortgage: $/month

Pending

MLS Number MDGA2004186

  • Single Family
  • Bedrooms 5
  • Bathroom 4
  • Acreage 1.38

*NEW CONSTRUCTION* Beautiful new Mountain Chalet just finished in Winter of 2022! Located in the Mountainside Community, this 5BR 4Bath home is centrally located in the heart of everything Deep Creek Lake has to offer. Enjoy the community lake access and tennis courts. The Chalet sits on over an acre of wooded land and is the perfect setting for a peaceful mountain getaway. Fully modern kitchen and bathrooms. Open concept living with a large recreation room downstairs makes this a dream for entertaining. Brilliantly designed to accommodate multiple families making this home perfect for a vacation rental as well. Ready for your finishing touches, don't miss your chance to make this brand new home your own! Call today for more details.

Listed by Jonathan D Bell of Railey Realty,Inc.

$
$
%
$/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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Lot 22 Backbone Drive Oakland MD 21550

Oakland, MDLot 22 Backbone Drive

Price$34,900

Est. Mortgage: $/month

MLS Number MDGA2004184

  • Land

Escape from it all on this impressive, 10.06 acre property in the Backbone Ridge community located adjacent to the highest point in Maryland! Driveway in place, electric to site and approved perc site. Capture some of the best western views from the building site on this property at almost 3000' in elevation! Call today for more info. At this price, this property won't last long!

Listed by Nick Fratz-Orr of Railey Realty,Inc.

$
$
%
$/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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181 Skippers Point Road Oakland MD 21550

Oakland, MD181 Skippers Point Road

Price$1,399,900

Est. Mortgage: $/month

MLS Number MDGA2004178

  • Condo
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 3,209

Completely remodeled Lake Front Log Cabin with Dock Slip! This recently renovated lake cottage features all new floors & fixtures, updated kitchen and bathrooms, and fresh paint inside and out. With 5 Bedrooms and 4 full baths, you'll have plenty of space to house multiple families, excellent for a vacation rental or your personal mountain retreat. Several living/rec rooms provides ample space for entertaining. Fully modern kitchen with all new stainless appliances, granite tops and walk-in pantry. The massive stacked stone fireplace and exposed wood beams offer a rustic touch to compliment the elegant modern finishes throughout. Upstairs primary suite has its own wet bar and living room for when you need to get away on your “get-away”. Adjoining the lake access trail to your community dock, and centrally located minutes from state parks, restaurants and WISP resort, this home has everything you need to enjoy what Deep Creek Lake has to offer. Call today for details!

Listed by Jonathan D Bell of Railey Realty,Inc.

$
$
%
$/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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115 Fingerboard Road Oakland MD 21550

Oakland, MD115 Fingerboard Road

Price$75,000

Est. Mortgage: $/month

MLS Number MDGA2004174

  • Land

.44 acre parcel on Fingerboard Rd, just outside of town and within Crellin School District. This property has a well, septic, and electric service already in place, and features a foundation. Bring your modular home or stick-build on top of the existing foundation. This one is ready to go!

Listed by Justin D Liller of Railey Realty,Inc.

$
$
%
$/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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17 Old Chestnut Drive Oakland MD 21550

Oakland, MD17 Old Chestnut Drive

Price$825,000

Est. Mortgage: $/month

MLS Number MDGA2004154

  • Single Family
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 966
  • Acreage 0.27

This charming 3 bedroom cabin is the quintessential Deep Creek Lake getaway! With a private Type A Dock walking distance from the home, and an original stone, wood burning fireplace inside, this cozy abode checks every box for year round enjoyment. Play on the lake during summertime, and hit the slopes all winter long. With recent updates such as a brand new roof and granite countertops, this property is turn key & ready to go. Established rental with Vacasa and currently producing impressive income. Schedule your showing today!

Listed by Nina A Beitzel of Railey Realty,Inc.

$
$
%
$/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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Bailiff Lane Oakland MD 21550

Oakland, MDBailiff Lane

Price$135,000

Est. Mortgage: $/month

MLS Number MDGA2004146

  • Land

25 acres lot d, e/s shady dell road- bailiff lane in oakland, md. All mineral rights convey. Electric at main road.

Listed by Michael Haywood of The Mike Haywood Group

$
$
%
$/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.

Save FavoriteSchedule TourAsk A QuestionMore Details

325 Coolidge Avenue Oakland MD 21550

Oakland, MD325 Coolidge Avenue

Price$131,800

Est. Mortgage: $/month

Active With Contract

MLS Number MDGA2004136

  • Single Family
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 834
  • Acreage 0.32

Just 1/2 mile from Hospital and downtown services, live simply in this easy maintenance home. Elevated above the town, take in scenic views. Enjoy outdoor living with your fully fenced back yard, sunny deck space, and a comfortable screened covered back porch, just off the dining area. Easy living is yours with handy kitchen laundry space and upgraded bath. Live with just the right amount of space with windows creating a bright and airy feeling.

Listed by Lana K Roby of Keller Williams Premier 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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2078 Sanders Lane Oakland MD 21550

Oakland, MD2078 Sanders Lane

Price$279,900

Est. Mortgage: $/month

MLS Number MDGA2004142

  • Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,904
  • Acreage 1

Well maintained 4BR / 2.5 BA home sitting on nicely landscaped 1 acre parcel. Located in serene neighborhood, but close to historical Oakland, MD, state parks, and Youghiogheny River. Minutes to Deep Creek Lake and WISP resort areas. Amenities include first floor BR, BA, and laundry hookups. Spacious open kitchen/dining room layout. Attached 2 car garage with attic. Library, back enclosed porch, and shed.

Listed by Paul A Macy of Garrett Land Sales,PC

$
$
%
$/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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Lot 5 Spring Bottom Road Oakland MD 21550
Pending

MLS Number MDGA2004122

  • Land

Looking for a secluded homesite adjacent to the Highest Point in Maryland? Look no further! This 4.36 acre has an approved perc site for a 5 bedroom home and is ready for you to build your dream cabin in the woods. Call today to setup a private showing!

Listed by Nick Fratz-Orr of Railey Realty,Inc.

$
$
%
$/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.

Save FavoriteSchedule TourAsk A QuestionMore Details

122 N 8Th Street Oakland MD 21550

Oakland, MD122 N 8Th Street

Price$249,000

Est. Mortgage: $/month

MLS Number MDGA2004110

  • Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,376
  • Acreage 0.28

Take advantage of this rare opportunity. The level lot with one level floor plan is ideal for just about any use or need. Completely updated 3 bedroom, 2 bath one level home in Oakland. Exterior Improvements include new doors and windows, recently replaced roof, new gutters and downspouts, stamped concrete sidewalk. Redesigned open floor plan, including bathrooms with tile showers, new vanities with granite tops, & glass shower door in primary bath. New kitchen layout with island, custom cabinetry, granite counter tops, new appliances, and appliances including granite counters. Interior improvements includes new walls, doors, trim, LVT waterproof flooring, and new insulation. Mechanical improvements include new: heating and air conditioning, plumbing, 200 amp wiring, LED lighting, hot water heater, & blue tooth sound systems in both bathrooms.

Listed by Bill G Weissgerber Jr. of Railey Realty,Inc.

$
$
%
$/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.

Save FavoriteSchedule TourAsk A QuestionMore Details

875 Mountainview Drive Oakland MD 21550

Oakland, MD875 Mountainview Drive

Price$880,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDGA2004098

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2,346
  • Acreage 1.17

Impressive, custom built home in the beautiful Mountainside Community. The open floor plan, oversized kitchen, granite counter tops, hardwood flooring and cathedral ceilings are just a few of the great features this home offers. Three levels of living space carefully thought out to really flow with friends and family. The lower level is partially finished, just waiting for your finishing touches. The large loft is a great space for an office and family room, providing one more area to enjoy. The abundance of windows brings the outside in during any season. Combine this with the stone fireplace, this home is very warm and inviting. The outside offers two cozy covered porches, which are plumbed for radiant heaters. If all of this isn't enough, the Mountainside community also allows you to enjoy the tennis courts, lake access and a club house. The location is also just minutes to Wisp Ski Resort! This home is sure to check off all the boxes!

Listed by Elizabeth S Spiker Holcomb of Taylor Made Deep Creek Vacations & Sales

$
$
%
$/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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169 Acres Near Mayhew Inn Garrett Highway Oakland MD 21550

MLS Number MDGA2004092

  • Land

Live, Play, Work with Deep Creek Lake, Wisp Ski Resort, and the best of the Maryland Mountaintop in your back yard. Let your entrepreneurial imagination run wild with 169 acres for development and business opportunities. Choose to create anything from a High Density townhouse community (Town Residential Zoning), with an indoor/outdoor Ice Center/Waterpark (Commercial Resort Zoning), to Farmettes, with an Equestrian Center (Lake Residential Zoning with Grandfathered Commercial use). Choose your pleasure, as multiple zoning districts uniquely intersect in this spot. Alternatively, you might want to keep most of it to yourself. Construct your mountaintop home that takes in panoramic lake views, while also enjoying the myriad of well developed trails, designed for walking, biking, motorized vehicle or horse riding. With an existing home and farm buildings, start enjoying the property the day of closing. This listing includes 3 Parcels: Map 58, parcels 184, 82 & 505

Listed by Lana K Roby of Keller Williams Premier 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

4009 Mayhew Inn Road, Garrett Highway & 62 Mitchellee Lane Oakland MD 21550

MLS Number MDGA2004062

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,864
  • Acreage 169

Live, Play, Work with Deep Creek Lake, Wisp Ski Resort, and the best of the Maryland Mountaintop in your back yard. Let your entrepreneurial imagination run wild with 169 acres for development and business opportunities. Choose to create anything from a High Density townhouse community (Town Residential Zoning), with an indoor/outdoor Ice Center/Waterpark (Commercial Resort Zoning), to Farmettes, with an Equestrian Center (Lake Residential Zoning with Grandfathered Commercial use). Choose your pleasure, as multiple zoning districts uniquely intersect in this spot. Alternatively, you might want to keep most of it to yourself. Construct your mountaintop home that takes in panoramic lake views, while also enjoying the myriad of well developed trails, designed for walking, biking, motorized vehicle or horse riding. With an existing home and farm buildings, start enjoying the property the day of closing. This listing includes 3 Parcels: Map 58, parcels 184, 82 & 505

Listed by Lana K Roby of Keller Williams Premier 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

932 Underwood Road Oakland MD 21550

Oakland, MD932 Underwood Road

Price$264,900

Est. Mortgage: $/month

Active With Contract

MLS Number MDGA2004070

  • Single Family
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,340
  • Acreage 1.38

You'll enjoy the Beautiful Country setting at this 2-story 3/4 Bedroom home located outside of Oakland on a 1.38 Acre level lot. The covered wrap around porch is a great spot to relax and grill out with family and friends. Indoors the spacious rooms on both floors provide privacy for your family. The Oak window seat in the Dining Room enhances that space. Upstairs are 3 bedrooms with a 4th bedroom option combined with the Utility Room. The attic space has potential for additional living area but serves as great storage space currently. Call today for you private showing.

Listed by Richard B Orr of Railey Realty,Inc.

$
$
%
$/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.

Save FavoriteSchedule TourAsk A QuestionMore Details

King Wildesen Road Oakland MD 21550

Oakland, MDKing Wildesen Road

Price$85,000

Est. Mortgage: $/month

Pending

MLS Number MDGA2004056

  • Land

22 acres of privacy in Western, MD! Looking for hunting property? A getaway place to camp or build a small cabin in the mountains? Look no further! Situated on the backside of Backbone Mountain, there is plenty of wildlife to suit your hunting goals and desires. No zoning restrictions, no HOA. Call today to schedule a private showing!

Listed by Nick Fratz-Orr of Railey Realty,Inc.

$
$
%
$/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.

Save FavoriteSchedule TourAsk A QuestionMore Details

2918 Oakland Sang Run Road Oakland MD 21550

MLS Number MDGA2003986

  • Single Family
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 1,382
  • Acreage 4.88

NEW PRICE! Beautifully renovated bright and sunny rancher on a spectacular almost 5-acre lot just minutes to Oakland and Deep Creek Lake! Just about everything is brand new! Custom lighting and fans throughout! Black six-panel doors throughout! Spacious living room and dining room with LVT floors, a kitchen fit for a chef with white cabinets, custom backsplash, stainless steel appliances, and beautiful granite counters! Built-in storage! Spacious laundry room with lots of storage! Three big bedrooms and a gorgeous full bath with subway tile in the shower, upgraded cabinetry, quartz counters, and beautiful lighting! HVAC '22! HWH '22! Windows '22! Siding '22! Ready for immediate delivery!

Listed by Charlotte Savoy and Patrick A Hawkins of Keller Williams Integrity

$
$
%
$/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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