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$199,900
1 Beds ⋅ 1 Baths ⋅ 202608700 MLS
Experience downtown living at its finest in this sunny first-floor condo located in a beautiful historic building on Main Street in Madison. Offering approximately 1,000 square feet, this charming condo features soaring 12-foot ceilings throughout, creating a bright and spacious atmosphere. The large one-bedroom, one-bath layout includes a walk-in shower, inviting family room with a fireplace, and a charming eat-in kitchen perfect for everyday living. Additional highlights include bonus exterior storage space, shared patio area, off-street parking, and several newer appliances. Conveniently located just steps from local shops, restaurants, wineries, popular festivals, and the scenic Ohio River, this condo offers the perfect blend of historic charm and downtown convenience. A must-see opportunity!

512 E Main Street Unit 1, Madison

Listing courtesy of F.C. Tucker/Scott Lynch Group.

$234,900
2 Beds ⋅ 2 Baths ⋅ 202608635 MLS
Charming two-story home located in the heart of downtown Madison! This well-maintained property offers 2 bedrooms, 2 full baths, a spacious living room, cozy family room, large laundry room, separate dining area, and an inviting kitchen with plenty of space for everyday living. Enjoy relaxing on the covered front porch with Main Street views. Take advantage of alley access to the backyard with convenient off-street parking. Recent updates include a newer roof approximately 5 years old and Thermopane windows throughout. Just a short walk to downtown shops, local eateries, wineries, and the picturesque Ohio River waterfront, this home combines comfort, convenience, and small-town charm in an ideal location.

931 W Main Street, Madison

Listing courtesy of F.C. Tucker/Scott Lynch Group.

$1,100,000
4 Beds ⋅ 2 Baths ⋅ 202608456 MLS
Welcome to an extraordinary property in the highly desirable Rykers Ridge area of Jefferson County, Indiana—where refined living meets breathtaking natural beauty. Situated on 57 pristine acres of rolling pasture & wooded acreage, this private retreat offers a rare combination of elegance, tranquility, & space. From the moment you arrive, the home’s timeless charm is evident in its inviting covered front porch & wraparound veranda—perfect for enjoying sweeping views & peaceful surroundings. Designed for both relaxation & entertaining, the outdoor spaces include a covered back porch & patio, all immersed in a serene landscape rich with wildlife. Inside, impeccable craftsmanship shines through with high ceilings, exquisite cabinetry, & two striking fireplaces that anchor the home’s sophisticated living spaces. The residence features two beautifully appointed kitchens, ideal for seamless multi-generational living or hosting guests in style with dedicated private quarters. Offering 4 spacious bedrooms & 2 spa-inspired bathrooms, every detail has been curated to provide comfort & luxury. A detached two-car garage with lean-to & a barn add both function & versatility to this remarkable property. Located just minutes from the charm & culture of Madison, Indiana, this estate delivers an unparalleled lifestyle of privacy, beauty, & elevated country living. If you’ve been dreaming of space, privacy, & a place to truly unwind—this Rykers Ridge property in Jefferson County is it.

2904 N Rykers Ridge Road, Madison

Listing courtesy of F.C. Tucker/Scott Lynch Group.

$49,000
202608287 MLS
Prime vacant lot in highly sought-after neighborhood. This lot offers the perfect canvas to build your dream home, nestled among beautifully designated residences in a vibrant and established community. With a cul-de-sac location, this property provides both privacy and convenience. Enjoy easy access to historic and award-winning downtown Madison. Schedule your showing today!

581 S Indian Cave Road, Madison

Listing courtesy of Coldwell Banker Harrell & Asso.

$310,000
3 Beds ⋅ 2 Baths ⋅ 202608313 MLS
You don't want to miss this beautifully updated 3 bedroom, 2 bath home offering over 1500 sq. ft. in a quiet cul-de-sac just minutes from town. Recent upgrades include new West Shore doors and windows, new flooring, new carpet, and fresh paint throughout. The kitchen also features new appliances! The roof is less than 2 years old and it has a brand new sump pump. Inside you'll love the spacious feel created by both tray and vaulted ceilings. The perfect blend of comfort, style, and convenience!

401 Maple Hill Drive, Madison

Listing courtesy of Coldwell Banker Harrell & Asso.

$324,900
2 Beds ⋅ 3 Baths ⋅ 202608000 MLS
Spacious, comfortable condominium in downtown Madison. Features tall ceilings, beautiful woodwork, and great natural light throughout. Cherry kitchen cabinets, granite counter top, all appliances, and breakfast bar. Large main suite with oversized window overlooking gardens and rooftops. Main suite includes well designed walk-in closet. Besides the main suite bath additional full bath and half bath off the second bedroom. Fireplaces are decorative. Beautiful staircase in common area with landing at this unit and additional back staircase. Large front porch for residence use. Front and back staircase. One car garage space with storage. Great location blocks away from the river front, shopping, dining, festivals, and all that Madison---USA Today's Best Small Town in the Midwest"--has to offer.

612B W Second Street Unit 4, Madison

Listing courtesy of Century 21 River Valley.

$475
202608143 MLS
Unit K2: 336 sq ft of efficient space at just $475/month. Secure building with convenient location. Perfect small-office. Contact us for availability.

220 Clifty Drive Unit Unit K2, Madison

Listing courtesy of eXp Realty, LLC.

$275,000
202608094 MLS
Located in the heart of downtown Madison on Main Street, this versatile three-story building offers 2,745 sq ft and endless possibilities. The main floor is currently operating as a t-shirt shop, but the space could easily accommodate a variety of retail, office, or service-based businesses. The upper floors provide excellent rental or residential potential. The second floor offers additional usable space, while the third floor is unfinished and ready for a buyer to customize to fit their needs. With the option to live and work in the same building or generate additional rental income, this property presents a unique investment opportunity. Situated on Main Street in Madison IN with high foot and vehicle traffic, you’ll be just steps away from popular restaurants, shops, wineries, and local attractions. A prime location with incredible potential in one of southern Indiana’s most charming historic downtowns.

225 E Main Street, Madison

Listing courtesy of F.C. Tucker/Scott Lynch Group.

$350,000
202608072 MLS
Value-Add Investment Opportunity in Madison, Indiana! This mobile home park features 8 total rental spots along with an additional single-family home and garage located on the property, providing multiple income streams. Property is being sold strictly as-is and priced to reflect its current condition. Exterior components, mechanical systems, and interior finishes will all require attention and a substantial capital improvement budget should be anticipated prior to stabilization. Significant deferred maintenance is present throughout the property. Cash buyers with construction resources and value-add experience strongly preferred. Conveniently located near local amenities, employment centers, and major routes, this property is well-positioned in a market with consistent affordable housing demand. Value-add opportunities include rental increases, infill optimization, and property-wide improvements. A rare chance to acquire a distressed multi-unit income property at a price that reflects the work ahead and strong long-term upside for the right investor.

3471 W Pin Oak Court, Madison

Listing courtesy of NextHome Wilson Real Estate.

$649,000
4 Beds ⋅ 3 Baths ⋅ 202607868 MLS
Check out this truly rare opportunity in Madison, where you can enjoy the convenience of being just minutes from town while owning over 6 acres of private, picturesque land. Properties like this are hard to find, offering the accessibility and peaceful country living. This stunning home lives up to the hype with beauty, quality, space, and a sense of tranquility that’s hard to match. Inside, you’ll find beautiful living space filled with custom finishes and intricate detailing. From crown molding and unique ceilings with ambient lighting to the impressive fireplace, every element has been thoughtfully designed to impress. The versatile floor plan offers flexibility to fit your lifestyle, with options for a first-floor bedroom or office, and additional rooms upstairs that could serve as a nursery or sitting area. Entertaining is a breeze with a formal dining room, breakfast nook, and open-concept main living areas that flow seamlessly together. In addition to the attached 2+ car garage, a detached 2-car pole barn provides ample storage for vehicles, hobbies, or recreational equipment. If you're seeking privacy, high-quality finishes, and room to roam—all while staying close to town—this exceptional property is truly a must-see.

4502 N SR 7, Madison

Listing courtesy of Coldwell Banker Harrell & Asso.

$265,000
3 Beds ⋅ 2 Baths ⋅ 202607860 MLS
Modern Luxury Meets Historic Convenience! This fully remodeled home offers a "brand new" living experience in the heart of downtown Madison. Interior Reinvention: The floor plan was strategically reconfigured to embrace a modern, open-concept layout. By merging the kitchen, dining, and living areas, the home now feels significantly more expansive and fluid. Complete Overhaul: Brand new roof, HVAC, double pane windows, and upgraded systems to include washer/dryer hookup. Privacy: A newly installed privacy fence secures the backyard, creating a dedicated, quiet sanctuary for outdoor living. Storage Galore: Multiple large closets throughout—rare for the area! Layout: 3 spacious bedrooms with primary suite on 1st floor and 2 full baths with modern finishes. Move-In Ready: Open layout perfect for entertaining or everyday living. Don't miss this opportunity to own a high-quality, low-maintenance home steps away from shopping, dining, and the Ohio River! -- Also, off-street parking perfect for golf cart/car!!

423 Mill Street, Madison

Listing courtesy of F.C. Tucker/Scott Lynch Group.

$139,900
202607751 MLS
Rare opportunity to own a beautiful 10 acre buildable lot in one of the area’s most desirable locations. Enjoy the peace and privacy of country living while being just minutes from town conveniences, shopping, dining, and schools. This property offers city water and city sewer access, making it ready for your dream home. Plenty of space for a custom build, gardens, workshop, or recreational use. A perfect blend of rural charm and modern convenience. Taxes currently reflect the full 30 acre parcel and will be adjusted accordingly for each individual 10 acre parcel. Soybeans have been planted for the 2026 season; seller will retain all rights to the 2026 crops.

2000+ E Cross Road Unit Lot 1, Madison

Listing courtesy of eXp Realty, LLC.

$139,900
202607753 MLS
Discover the ideal setting for your future home on this scenic 10 acre vacant lot. Located in a highly sought-after area, this property offers the best of both worlds, quiet country surroundings with quick access to town. City water and city sewer are available, adding exceptional value and ease for development. With a unique layout and generous acreage, there is ample room for a home, barn, outdoor entertaining space, and more. Taxes currently reflect the full 30 acre parcel and will be adjusted accordingly for each individual 10 acre parcel. Soybeans have been planted for the 2026 season; seller will retain all rights to the 2026 crops.

2000+ E Cross Road Unit Lot 2, Madison

Listing courtesy of eXp Realty, LLC.

$324,900
3 Beds ⋅ 2 Baths ⋅ 202607581 MLS
Beautiful first floor Federal style condominium blocks away from the river front, shopping, dining, festivals, and all that Madison---USA Today's Best Small Town in the Midwest"--has to offer. Amazing remodeled kitchen boasts all major appliances, granite counter top, track lighting, under-cabinet lighting and plenty of counter space. Open floor plan with 10 ft ceilings, crown molding, recess lighting, chandeliers, hardwood flooring in foyer, living room and kitchen. Split bedrooms with owner using third bedroom as a sitting room. Owners suite has large dressing closet with additional vanity and built in desk. Large front porch for residence use. Small patio for owners use. One car garage space with storage and easy access from the condo. Don't let this move-in ready maintenance-free home pass you by.

610A W Second Street Unit 1, Madison

Listing courtesy of Century 21 River Valley.

$464,500
4 Beds ⋅ 4 Baths ⋅ 202607755 MLS
Completely remodeled and thoughtfully designed, this stunning 4-bedroom, 3.5-bath home offers 2,544 sq ft of beautifully updated living space in the heart of downtown Madison. Blending modern updates with timeless character, you’ll find exposed brick, wood beams, and quality craftsmanship throughout. The spacious kitchen features abundant cabinetry, a pantry, large island, and an attached dining area—perfect for everyday living and entertaining. The primary suite offers a generous layout with a large bath, and large closet. while natural light fills the home, creating a warm and inviting atmosphere, you wont want to miss what outside has to offer! Enjoy a private courtyard ideal for relaxing or outdoor dining, which leads to a detached two-car garage for added convenience and storage. Located just moments from shops, dining, wineries, and all that downtown Madison has to offer, this home is truly a must-see.

422 St Michaels Avenue, Madison

Listing courtesy of F.C. Tucker/Scott Lynch Group.

$160,000
2 Beds ⋅ 1 Baths ⋅ 202607644 MLS
Price adjustment! This charming home on a corner lot is perfectly positioned in the heart of downtown Madison, just minutes from the bridge and all the activities this vibrant community is known for. Enjoy the convenience of walkable living while still having your own private retreat. This home features hardwood and tile flooring, a dining room, and a layout ideal for everyday living and entertaining. The kitchen comes equipped with a gas stove and refrigerator (both new in 2022) Downstairs, you’ll find a partially finished full basement, offering additional living space and room to customize to your needs. There’s also attic access with a wood floor for even more storage. Step outside to enjoy the fenced yard, perfect for pets or gatherings. The property also includes a single-car detached garage and sits on a desirable corner lot. Key Updates & Features Include: Tankless water heater 2021 Water softener 2021 New interior water lines 2020 New exterior water & sewer lines 2025 HVAC system 2017 Roof, gutters, and aluminum siding 2019 Exterior cameras stay with the home (interior cameras function as live monitors only) As a unique bonus, the tanning bed will remain. With its prime location near the bridge for easy commuting, plus numerous updates, this home offers both convenience and peace of mind. Property is being sold AS IS. Buyers are welcome to complete any inspections, however the Sellers will not make repairs or provide repair concessions.

904 E Second Street, Madison

Listing courtesy of eXp Realty, LLC.

$1,375,000
10 Beds ⋅ 8 Baths ⋅ 1713737 MLS
Own a Piece of Historic Downtown Madison Discover a rare investment opportunity in the heart of downtown Madison. This versatile corner lot property features four beautifully maintained Airbnb units, offering both charm and strong income potential. The thoughtfully designed layout includes: Main Floor: Two spacious 2 bedroom, 1.5 bath units Upper Level: Two expansive 3 bedroom, 2 bath units Currently operating as a successful short-term rental, this property delivers excellent returns and comes as a true turnkey investment complete with future bookings and all furnishings included, allowing for a seamless transition. Endless Possibilities: Continue as a high performing Airbnb, Multi generational living setup, convert to condo-style rentals, Owner occupy one unit while renting the others. Recent Updates Include: complete rehab, all systems new. Perfectly positioned in a highly walkable downtown location, you're just steps from local boutiques, dining, and the scenic Ohio River. Blending historic character with modern upgrades, this property is a standout opportunity in one of Indiana's most sought after river towns.

513 & 515 West St, Madison

Listing courtesy of EXP Realty LLC.

$1,375,000
10 Beds ⋅ 8 Baths ⋅ 202607078 MLS
Own a Piece of Historic Downtown Madison Discover a rare investment opportunity in the heart of downtown Madison. This versatile corner lot property features four beautifully maintained Airbnb units, offering both charm and strong income potential. The thoughtfully designed layout includes: Main Floor: Two spacious 2 bedroom, 1.5 bath units Upper Level: Two expansive 3 bedroom, 2 bath units Currently operating as a successful short-term rental, this property delivers excellent returns and comes as a true turnkey investment complete with future bookings and all furnishings included, allowing for a seamless transition. Endless Possibilities: Continue as a high performing Airbnb, Multi generational living setup, convert to condo-style rentals, Owner occupy one unit while renting the others. Recent Updates Include: complete rehab, all systems new. Perfectly positioned in a highly walkable downtown location, you’re just steps from local boutiques, dining, and the scenic Ohio River. Blending historic character with modern upgrades, this property is a standout opportunity in one of Indiana’s most sought after river towns.

513 & 515 West Street, Madison

Listing courtesy of eXp Realty, LLC.

$379,000
3 Beds ⋅ 2 Baths ⋅ 202606645 MLS
Historic Federal style home built in 1850 in the heart of historic downtown Madison. Step into a beautifully maintained home by its owners. You will be welcomed by a open staircase, sunny living, and dining rooms with original, restored pine floors. Living room features the orginal fireplace (now decorative) and leaded glass hangings in the front windows. Large kitchen is highlighted with vintage General Electric steel kitchen cabinets in amazing condition. Granite counter top and tile back-splash. The unique kitchen floor is plank eucalyptus. The rear project/utility/garden room has a large storage closet and big picture window looking at the landscaped and peaceful fenced yard and patio. Covered back door entrance. Three spacious bedrooms. Second and third bedrooms currently used by the homeowners as TV/reading room and office. Completely remodeled baths (full and half) with tile flooring, shower, refinished claw-foot tub and stainglass window hangings in the full bathroom. Home is located close to dining, shopping, riverfront, festivals and all that Madison---USA Today's "Best Small Town in the Midwest"--has to offer.

507 E Main Street, Madison

Listing courtesy of Century 21 River Valley.

$376,900
2 Beds ⋅ 2 Baths ⋅ 202606763 MLS
Scenic river view and comfortable downtown living in this two year old home. This two bedroom, two bath residence provides a designer kitchen with breakfast bar, granite counter top and tile backsplash. Open concept living and dining area with open staircase to basement. River view from living and dining areas. Large family room walk-out to covered patio and river view. Have your morning coffee or evening beverage with view of the sun shinging on the river or the sunset over the bridge. Home is located close to river walk, riverfront parks, dining, shopping, festivals and all that Madison---USA Todays's "Best Small Town in the Midwest"--has to offer.

1010 E First Street, Madison

Listing courtesy of Century 21 River Valley.

$264,900
3 Beds ⋅ 2 Baths ⋅ 202606836 MLS
Built around 1870, this charming 2-story Federal-style brick home is located in the heart of downtown Madison, just half a block from the Ohio River and outside the flood plain. Offering 1,668 sq ft, the home features 3–4 bedrooms and 2 full baths, blending timeless historic character with everyday convenience. Enjoy being within walking distance—or a quick golf cart ride—to local shops, dining, parks, festivals, and events. Inside, you’ll find spacious living areas filled with natural light and classic architectural details. The flexible layout allows for everyday living on the main level with additional space upstairs for guests. Recent updates, including a newer roof, windows, and water heater, add peace of mind while leaving room to make it your own. Outside, the low-maintenance yard includes a storage shed, with all appliances, blinds, and even lawn equipment included. Whether you're searching for a full-time residence, weekend retreat, or investment opportunity, this downtown gem offers location, charm, and versatility!

115 Walnut Street, Madison

Listing courtesy of F.C. Tucker/Scott Lynch Group.

$349,900
4 Beds ⋅ 3 Baths ⋅ 202606801 MLS
Fully renovated historic Federal-style brick home located in downtown Madison. This two-story property offers 4 bedrooms and 2.5 bathrooms and blends timeless character with modern updates. Features include a spacious open kitchen with new cabinetry, stainless steel appliances, center island with breakfast bar, coffee bar, and butler’s pantry. Main level includes living room, flex room that offers the potential for a main level bedroom or office, powder room, and large laundry room with sink. Home showcases three decorative fireplaces and a primary suite with ensuite bath featuring double vanity and tiled shower. Enjoy a private fenced backyard, detached 2-car garage, and cellar for storage. Located in the heart of historic downtown near local shops and dining.

518 Jefferson Street, Madison

Listing courtesy of F.C. Tucker/Scott Lynch Group.

$264,900
3 Beds ⋅ 2 Baths ⋅ 202606592 MLS
Motivated Seller!!! Beautiful new construction home offering 1,450 sq ft of thoughtfully designed living space. This 3-bedroom, 2 full bath home features an open floor plan connecting the kitchen, dining area, and living room—perfect for everyday living and entertaining. The eat-in kitchen includes stainless steel appliances, abundant cabinet space, a large pantry, and a center island with additional storage drawers. The spacious primary suite offers a private bath with double vanity, walk-in shower, and both a walk-in closet plus a second closet for extra storage. The second full bath features a convenient tub/shower combination. Additional highlights include plenty of natural lighting throughout, a separate laundry room that leads directly to the garage, and a paved driveway with a turnaround for easy access. Step outside to enjoy the fenced backyard and back deck—ideal for relaxing or entertaining.

3450 N Michigan Road, Madison

Listing courtesy of F.C. Tucker/Scott Lynch Group.

$40,000
202606516 MLS
One bedroom, one bath, wood frame structure on the property. Assessor information shows 495 Sq ft. Property is inhabitable, but possibilities of a Pace Grant. Sold "As Is"

801 Gerry Lane, Madison

Listing courtesy of Century 21 River Valley.

$494,900
202606336 MLS
Discover the possibilities with this stunning 101.54-acre property offering the perfect blend of privacy, recreation, and potential. Mostly wooded with some tillable ground, this diverse tract stretches down to the creek, creating a beautiful natural setting and attracting abundant wildlife. Previously used for hunting and camping, this land is ideal for outdoor enthusiasts looking for their own private getaway. Whether you envision a recreational retreat, hunting property, weekend camping spot, or building your country dream home tucked away in nature, the opportunities here are endless. Peaceful, private, and full of potential—make this acreage your own.

2256 N Brooksburg Manville Road, Madison

Listing courtesy of F.C. Tucker/Scott Lynch Group.

$459,000
1 Beds ⋅ 1 Baths ⋅ 202605428 MLS
If you're looking for a ultimate log cabin retreat then look no more. Our cabin is a unique, small, authentic 19th century log home, nestled among cedar trees while overlooking a pond. The cabin offers the perfect retreat away from the hustle and bustle of everyday life. The log cabin has been completely restored with modern conveniences yet still retains all the rustic charm of an era gone by. Set on 30-/+ private scenic acres. This intimate retreat overlooks the beautiful backdrop of rolling ridges with expansive views of southern Indiana's Jefferson county. Refresh your body and spirit in the serene atmosphere of Francine's Log Cabin. Listed BELOW Appraisal Value.

2945 N Greenbrier Road, Madison

Listing courtesy of Trueblood Real Estate.

$219,000
2 Beds ⋅ 2 Baths ⋅ 2025013009 MLS
Charming and newly renovated home with fresh paint, updated flooring, and a sleek modern kitchen offers the perfect blend of comfort and functionality. The home offers 2 BD/2BA and a bonus room upstairs that can be a 3rd BD with spacious storage. The unfinished basement offers excellent potential for additional living space, making this home a fantastic opportunity with room to grow. This home blends comfort, character, and convenience in a great location on the hilltop. Schedule your showing today.

2159 Lanier Drive, Madison

Listing courtesy of Century 21 River Valley.

$129,000
2025012675 MLS
Open to interpretation!! How shall this property be finished? The preservation organization succeeded in stabilizing and beatifying its original footprint! This cottage needs to be made cozy by an individual ready to give it its layout and design. There are preservation covenants, held by Indiana Landmarks, with this property.

707 Walnut Street, Madison

Listing courtesy of Legacy Land Use & Realty.

$284,900
3 Beds ⋅ 1 Baths ⋅ 1703460 MLS
Immediate possession! Country Living with Convenience! Enjoy the best of both worlds with this brick 3 bedroom, 1.5 bath home situated in a rural setting, yet just 10 minutes from Madison's hilltop and about an hour from both Columbus and Jeffersonville, IN. The home offers multiple living spaces with a living room, family and a sunroom making this great for gatherings. The converted garage now serves as a spacious 19.7 x 13.9 bonus room, currently a laundry space, but ideal for storage, hobbies, a workshop, or even a man cave. A 26x32 detached 2 car garage and ample driveway parking add convenience. For horse enthusiasts, the property offers a 100x24 barn with 6 to 8 stalls, a tack room, and a large fenced pasture area. With so much space inside and out, this home provides endless possibilities for country living. This home has been recently inspected with no major defects found. Buyers are welcome to conduct any and all inspections; property is being sold in current condition, with no repairs to be made by the seller. With a full price offer, seller will give at closing a check to roofer for $9350.00 see attached estimate.

6734 N SR 7, Madison

Listing courtesy of EXP Realty LLC.

$284,900
3 Beds ⋅ 2 Baths ⋅ 2025011353 MLS
Immediate Possession! Country Living with Convenience! Enjoy the best of both worlds with this brick 3 bedroom, 1.5 bath home situated in a rural setting, yet just 10 minutes from Madison's hilltop and about an hour from both Columbus and Jeffersonville, IN. The home offers multiple living spaces with a living room, family and a sunroom making this great for gatherings. The converted garage now serves as a spacious 19.7 x 13.9 bonus room, currently a laundry space, but ideal for storage, hobbies, a workshop, or even a man cave. A 26x32 detached 2 car garage and ample driveway parking add convenience. For horse enthusiasts, the property offers a 100x24 barn with 6 to 8 stalls, a tack room, and a large fenced pasture area. With so much space inside and out, this home provides endless possibilities for country living. This home has been recently inspected with no major defects found. Buyers are welcome to conduct any and all inspections; property is being sold in current condition, with no repairs to be made by the seller.

6734 N SR 7, Madison

Listing courtesy of eXp Realty, LLC.