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$788,900
5 Beds ⋅ 4 Baths ⋅ 1721036 MLS
Set on a secluded 1.59 acre wooded estate in Grand Oaks, this refined residence offers a rare blend of privacy, elegance, and timeless architectural presence. Surrounded by mature trees and natural landscape, the home feels like a serene retreat moments from Crestwood. Inside, soft natural light and elevated finishes create an atmosphere of quiet luxury. The great room's fireplace adds understated warmth, while the gourmet kitchen pairs clean lines with beautifully crafted cabinetry and surfaces. The primary suite offers a calming, spa inspired escape, and every room reflects a commitment to simplicity, comfort, and refined design. Expansive outdoor spaces overlook the wooded backdrop, offering unmatched tranquility and connection to nature.

2003 Wooded Oak Ln, Crestwood

Listing courtesy of RE/MAX Real Estate Champions.

$219,000
2 Beds ⋅ 2 Baths ⋅ 1720923 MLS
Rare investment opportunity for a 1,000 sqft, 100-year old cottage in highly desirable Crestwood - just minutes from I-71 and I-265, the Paddock and Springhurst shopping areas, and Norton Commons. Kenwood Station, SOMS, and SOHS school district. Situated on over 1 acre, this property offers tremendous potential for redevelopment as a rental cottage, renovation for a precious new home, or a private, but convenient land site for a custom new build. Bring your vision and unlock the potential of this exceptional homesite.

8330 Ballardsville Rd, Crestwood

Listing courtesy of Premier Homes Realty.

$865,000
4 Beds ⋅ 4 Baths ⋅ 1720814 MLS
Come view this absolutely stunning 3-year old Brentwood ranch, packed to the brim with upgrades. From the elegant trim and built-ins by the fireplace, to the GE Cafe appliances, to the luxurious steam shower in the primary, this home has features to spare. By the entryway, theres an office room with french doors, that opens into the spacious open living room. This home sings with natural light, as the sun rises on the front of the home and sets over the back yard. The kitchen isn't just beautiful, its functional as well, with ample storage, counter space, and room to entertain. The primary suite is elegant with tray ceilings and large enough for your suite of furniture to fit comfortably. The primary closet is massive with upgraded shelving, and opens in to the laundry room for easy access. The two additional bedrooms on the other side of the first floor share a gorgeously tiled bathroom. The basement was recently finished in style, with high end trim, stately color schemes, and no wasted spaces. The hobby room in the basement is large enough to be walled into a home theater, made into a billiards or poker room, or could be an open space for enjoyment. The basement features a bedroom and full bathroom as well as an office space. Additionally, theres a massive utility and storage room that could be finished in to add extra space OR left to give you more storage than you could hope to fill up. As we head outside, you'll find a stunning screened in porch overlooking the backyard. The large space is perfect for letting the pets enjoy the sun, entertaining guests, or for tossing a football around. The home has solar panels installed on the roof, which serve to heavily reduce your electric bills. Schedule your private showing today, this home will not last long!

7395 Edith Way, Crestwood

Listing courtesy of Reserve Realty Group.

$342,500
3 Beds ⋅ 3 Baths ⋅ 1720616 MLS
Welcome to the charming community of Garden Homes at Stone Ridge. Tucked away near Buckner city limits, this intimate neighborhood features just 22 patio homes, offering a peaceful setting with the convenience of nearby shopping at Oldham County's newest Kroger, an easy drive to historic downtown Lagrange, and accessibility of nearby I-71. This well-maintained 3 bedroom, 3 full bath home combines comfortable living with the ease of a low maintenance lifestyle. The vaulted great room serves as the heart of the home, featuring a cozy gas fireplace and an open, inviting atmosphere. Freshly painted in Sherwin-Williams' popular "Utterly Beige" creates a warm, neutral palette for a move-in ready backdrop, perfect for any decorating style. Designed for convenient first floor living, this home features a spacious primary suite with an updated walk-in shower, a second bedroom with new carpet, an additional full bath, and a first floor laundry room located just off the garage. The kitchen offers charming glass-front upper cabinets that add both character and functionality, pantry for extra storage, and access to both a cozy breakfast nook and a space large enough to host a dining room experience. Upstairs, a private third bedroom with its own ensuite full bath creates the perfect retreat for guests, a home office, or flexible bonus living space. Step outside to enjoy your own private patio, ideal for morning coffee or simply relaxing in a peaceful setting. An attached two-car garage provides secure parking and storage, while the private driveway offers space for two additional vehicles. Residents enjoy the benefits of low-maintenance living, with monthly HOA fees covering master insurance, exterior maintenance, groundskeeping, water, sewer, and trash services. Enjoy the simplicity of a patio home lifestyle where comfort, convenience, and low maintenance living come together in the heart of Oldham County.

4213 Garden Ridge Rd, Crestwood

Listing courtesy of RE/MAX Results.

$285,000
3 Beds ⋅ 2 Baths ⋅ 1717497 MLS
This fully renovated 3-bedroom, 2-bath home in Pewee Valley gives you the fresh start you've been hoping for - without the projects, surprises, or extra costs. From the moment you walk in, you'll feel the difference. New roof, new flooring, fresh paint, updated electrical panel, new windows, siding, lighting, kitchen cabinets, and more—so you can focus on living, not fixing. The open flow between the living room and eat-in kitchen makes everyday life easier, whether you're hosting friends or just enjoying a quiet night in. With everything on one level, this layout is designed for simplicity and comfort. Your primary bedroom offers a private bath, while two additional bedrooms and a second full bath give you flexibility for family, guests, or a home office. Step outside and picture your weekends here. The deck is ready for entertaining friends and family - summer cookouts, quiet morning coffee, or winding down at the end of the day. The fenced backyard offers a comfortable outdoor space for pets, play, or simply enjoying a little fresh air. Above the detached garage, you'll find a fantastic bonus space that adapts to your life. Whether you need a home office, guest retreat, creative studio, workout area, or playroom, this extra space gives you options without sacrificing your main living areas. Set on a peaceful, scenic lot in Pewee Valley, you get the best of both worlds - quiet surroundings with convenient access to the Gene Snyder Freeway, shopping, dining, medical facilities, and highly regarded Oldham County schools. If you've been searching for a move-in ready home with flexibility, updates, and space that works for your lifestyle, this is your opportunity to step into it. Schedule your private showing today!

7614 Fraziertown Rd, Pewee Valley

Listing courtesy of Keller Williams Collective.

$215,000
3 Beds ⋅ 1 Baths ⋅ 1720160 MLS
This adorable, charming home includes 3 bedrooms and 1 full bath. You will notice this home is filled with natural light with larger windows throughout. The eat in kitchen is nicely sized with freshly painted cabinets along with newer countertops and backsplash. Flooring has been updated throughout the home as well. The full bath is stylish with beautiful flooring and updated as well. Outside you will enjoy the large front yard with very nice landscaping as well as a very large fully fenced in backyard that includes a nice sized back deck off of the kitchen. The sellers have always used window AC units and space heaters for the seasons and have found it to be very comfortable!

4513 Timothy Way, Crestwood

Listing courtesy of Homepage Realty.

$400,000
3 Beds ⋅ 3 Baths ⋅ 1719985 MLS
This bungalow style home sits on 1 acre of beautiful land near the heart of Crestwood, just over the Pewee Valley line! Enjoy the peaceful feel of country living, while being located close to all the amenities of the city. This home has been freshly painted throughout. This home has been completely redone; New flooring, New plumbing, New bathrooms and much more!! Don't miss out on this one and schedule a showing today!

6621 Sumac Ln, Crestwood

Listing courtesy of Weichert Realtors-H. Barry Smith Co..

$524,700
4 Beds ⋅ 3 Baths ⋅ 1719280 MLS
Welcome to 1002 Heron Cove. This beautiful 4 bedroom, 2.5 bath home has so much to offer. Enter into an open floor plan. Living room with a large window for a great view of the backyard. Kitchen with a large island, lots of cabinets and counter space. Shelving was added to the walk-in pantry for more storage. Refrigerator, gas stove, dishwasher and microwave to remain. Nice size dining area. A half bath and an area with a bench and closet. Second floor has a large Primary bedroom with a large walk-in closet. The primary bath has a double sink vanity and enclosed shower. There are three additional bedrooms with nice size closets, full bathroom and a hall closet. Basement, 2 car garage and a covered deck to enjoy. This home is located in a cul-de-sac.

1002 Heron Cove, La Grange

Listing courtesy of RE/MAX Performance Realty.

$324,900
3 Beds ⋅ 2 Baths ⋅ 1719168 MLS
This townhome is not only convenient to amenities, but is also affordable, new construction with an attached garage in new development, close to EVERYTHING! Across from Maples Park that features a walking trail, dog area, and amphitheater. This townhome is very spacious with the "farmhouse" look.

7302 Park Vue Dr, Crestwood

Listing courtesy of RE/MAX Real Estate Champions.

$525,000
4 Beds ⋅ 2 Baths ⋅ 1718733 MLS
Great cape cod on over an acre in Crestwood not in a subdivision! This charming cap cod has been beautifully updated and is move in ready! The house sits on just over an acre minutes to the local schools. The home has a first floor primary, hardwood floors on the main level. Two bedrooms and a bath on the second level. Lovely finished walk out basement. Outside you have a beautiful treed yard with a great barn set up partly as a garage and part as storage. Tons and tons of charm!

1105 E HWY 22, Crestwood

Listing courtesy of Pollard Realty.

$399,900
3 Beds ⋅ 4 Baths ⋅ 1718059 MLS
Directly across from Maples Park in Crestwood, this townhome is not only convenient to amenities, but it is priced to sell quickly. 7401 Park Vue Dr has been finished with no detail missed- from the large windows only an end unit can feature, to high end stainless GE appliances, a deluxe washer / dryer in the home, french door refrigerator, beautiful Brecher's Lighting fixtures, tiled backsplash, large common living areas, two separate full baths on the bedroom floor, and upgraded flooring.

7401 Park Vue Dr, Crestwood

Listing courtesy of RE/MAX Real Estate Champions.

$1,600,000
5 Beds ⋅ 7 Baths ⋅ 1718050 MLS
An exceptional opportunity awaits in prestigious Brentwood Estates, where luxury, privacy, and personalization come together to bring your dream home to life. Perfectly positioned on over an acre at the end of a quiet cul-de-sac, this custom-built residence offers a rare combination of peaceful surroundings and refined living in one of Oldham County's most desirable communities. Thoughtfully designed with both elegance and everyday functionality in mind, this expansive floor plan features 5 bedrooms and an open-concept layout ideal for comfortable living and effortless entertaining. The luxurious first-floor primary suite serves as a private retreat, while dedicated laundry rooms on both the first and second levels provide added convenience for modern lifestyles. Crafted with exceptional attention to detail, the home will showcase premium finishes, timeless architectural elements, and superior craftsmanship throughout. What truly sets this opportunity apart is the ability to personalize the design—working directly with the builder to curate selections and tailor finishes to reflect your vision and style. This is more than a home—it's an opportunity to create a one-of-a-kind living experience in one of Oldham County's premier neighborhoods. This is a proposed build and the builder is open to the buyer adjusting plans to make the build accommodate appropriately. Also the buyer could have an option in making certain cosmetic selections- paint, lighting, flooring, etc.

6405 Chatham Ct, Crestwood

Listing courtesy of Lenihan Sotheby's Int'l Realty.

$685,000
3 Beds ⋅ 3 Baths ⋅ 1717025 MLS
Motivated seller!! Escape to your own private retreat in beautiful Oldham County with this rare 3-bedroom, 2.5-bath ranch on over 5 scenic acres. Perfectly blending comfort and adventure, this property offers an incredible lifestyle both inside and out. You'll find spacious living areas filled with natural light, a kitchen ideal for entertaining, and a primary suite overlooking the serene landscape. Step outside to your backyard oasis featuring an above-ground pool, a picturesque pond with fountain, and wide-open views that invite relaxation. Explore wooded trails, spend the afternoon cooling off in your private swimming hole on the creek, or for outdoor enthusiasts, the huntable acreage and shooting range are make this a sportsman's paradise. Truly a one-of-a-kind property.

2010 Clearview Dr, La Grange

Listing courtesy of Parkside Realty.

$370,000
3 Beds ⋅ 3 Baths ⋅ 1716259 MLS
More photos to come! Welcome to your private retreat in highly desirable Oldham County, where comfort and lifestyle come together in this beautifully maintained 3-bedroom, 2.5-bath home featuring a spacious layout and a fully finished basement perfect for additional living or entertainment space; step outside to a fully fenced backyard designed for unforgettable gatherings with a sparkling pool, a custom tiki hut, and a one-of-a-kind outdoor bread and pizza oven, creating the perfect blend of relaxation and entertaining in one exceptional property.

5213 Manor Dr, Crestwood

Listing courtesy of BERKSHIRE HATHAWAY HomeServices, Parks & Weisberg Realtors.

$685,000
4 Beds ⋅ 5 Baths ⋅ 1713639 MLS
BRIAR HILL ESTATES, ALL-BRICK TRADITIONAL TWO-STORY WITH FINISHED WALK-OUT BASEMENT. OPEN CONCEPT ON THE MAIN FLOOR--WELCOMING ENTRY FOYER AND TAPERED COLUMN ACCENTS CREATE DIVIDED LIVING SPACES AND YET AN OPEN FEEL. HARDWOOD FLOORING IN THE GREAT ROOM, FORMAL LIVINGROOM/OFFICE AND DINING ROOM. EAT-IN KITCHEN WITH UPDATED CUSTOM CABINETRY, WRAP-AROUND COUNTERTOPS, AND CERAMIC TILE FLOORING, NICE FOR ENTERTAINING. THERE IS A MUDROOM FROM THE KITCHEN TO THE OVERSIZED ATTACHED 3-CAR GARAGE W/MODINE GAS GARAGE HEATER. NICE TRIM WORK AND MOLDINGS THROUGHOUT. UPSTAIRS, THE SPACIOUS PRIMARY BEDROOM SUITE IS ACCENTED BY A BEAUTIFUL BAY WINDOW AND HAS A LARGE L-SHAPED WALK-IN CLOSET OFF THE SPACIOUS PRIMARY BATH. THREE OTHER BEDROOMS, ONE WITH A PRIVATE BATH, ALL BOAST OF GENEROUS CLOSET SPACES. A THIRD FULL BATH SERVES THE REMAINING TWO BEDROOMS. THE FINISHED WALK-OUT BASEMENT OFFERS A 2ND FAMILY ROOM AREA W/FIREPLACE, LARGE HOME-OFFICE AREA, FULL BATH, AND ANOTHER RESOURCE AREA GREAT FOR A SCRAP BOOKING ROOM, ETC. BEAM CENTRAL VACUUM SYSTEM. LARGE LOT, .75 ACRE ACCORDING TO OLDHAM CO. PVA, WITH MATURE TREES AND LANDSCAPING. DETACHED ALL-BRICK OVERSIZED 2-CAR GARAGE (IN ADDITION TO THE ATTACHED 3 CAR SIDE ENTRY GARAGE) WITH MODULAR FLOORING TILES. BRIAR HILL PARK IS LOCATED AT 7400 E. ORCHARD GRASS BLVD. OFFERING TENNIS COURTS, PLAYGROUND, PAVILLION, SAND VOLLEYBALL, FULL COURT BASKETBALL & WALKING TRAIL, VISIT: OLDHAMKYLEWISANDCLARK.COM SELLER IS PROVIDING 1 YEAR HSA HOME WARRANTY TO BUYER AT CLOSING, MUST SEE!!!

6311 Breeze Hill Rd, Crestwood

Listing courtesy of Semonin Realtors.

$875,000
6 Beds ⋅ 5 Baths ⋅ 1712403 MLS
Refined living in Brentwood, part of the esteemed Oldham County School District. This beautifully appointed modern farmhouse with Craftsman architectural influence offers 6 bedrooms and 3,458 square feet of finished living space. A classic brick exterior complemented by freshly painted board-and-batten detailing is framed by curated landscaping and an irrigation system. The expansive front swinging porch - creates a welcoming, year-round gathering space. Inside, a light-filled open layout highlights custom craftsmanship throughout. The gourmet kitchen features ceiling-height cabinetry, granite and butcher-block counter space, a dedicated bar area with a beverage refrigerator, a coffee station, and a walk-in pantry with additional prep counter space, ideal for entertaining while maintaining an uncluttered workspace. The great room showcases attentive detail with a coffered ceiling and is anchored by a one-of-a-kind reclaimed wood mantel sourced from a historic barn in the Hoosier National Forest, paired with a gas-burning fireplace providing instant warmth and ambiance. Everyday living is effortless with a thoughtfully designed mudroom entry off the 3-car garage, offering an organized, functional space that supports busy routines while keeping the rest of the home pristine. The main-level primary suite is a private sanctuary with vaulted ceilings, direct access to the backyard and hot tub, heated bathroom floors, a deep soaking tub, and a spa-inspired shower with multiple shower heads, dual vanities and a walk-in closet. The second floor includes four bedrooms and two full bathrooms. The lower level expands the home's versatility with a full ensuite guest bedroom, a discreet safe room/storage shelter, and multiple unfinished areas ready to be customized into additional living, recreation, or wellness spaces. A covered rear porch overlooks a flat yard with a hot tub - ideal for relaxing or entertaining. The home is wired with CAT6 Ethernet throughout, readiness for wireless access points, and a private security system. Brentwood residents enjoy neighborhood amenities and activities, including clubhouse gatherings, pool days, tennis, pickleball, and a vibrant community atmosphere.

6370 Clore Ln, Crestwood

Listing courtesy of Semonin Realtors.

$1,185,000
4 Beds ⋅ 4 Baths ⋅ 1711473 MLS
Welcome to this exquisite luxury custom build by the renowned Mason Construction. Situated on over an acre in the sought after community of Brentwood, this 4-bedroom, 3.5-bath masterpiece showcases the builder's signature attention to detail and high-end masonry work.The open-concept floor plan is anchored by a gourmet kitchen and a light-filled great room, perfect for both intimate family evenings and grand-scale entertaining. The primary suite has a spa inspired ensuite and generous walk-in closet space. Three additional spacious bedrooms along with a loft and well-appointed baths ensure comfort for family and guests alike. A true must see!

7209 Sunset Ln, Crestwood

Listing courtesy of Keller Williams Collective.

$1,074,900
4 Beds ⋅ 4 Baths ⋅ 1708040 MLS
Welcome home! This custom built home features an open floor plan with a vaulted ceiling in the great room, 2 fireplaces, and a cozy private retreat. Located in Farmhouse Estate, it is one of the last opportunities to have new construction in Crestwood's most desirable neighborhood! Custom built home features many amazing finishes and unique items...The''Keeping Room'' is easily accessible from both the Primary Suite or the kitchen. Fall away wooded rear lot. Lower level finished with bedroom, bathroom, big family room and tractor room. Lots of large windows. Walkout to treed back yard.

5607 Farmhouse Lot 19 Dr, Crestwood

Listing courtesy of RE/MAX Real Estate Champions.

$1,700,000
2 Beds ⋅ 1 Baths ⋅ 1707458 MLS
Opportunity knocks! OLDHAM COUNTY DEVELOPMENT OPPORTUNITY 17.85 ACRES. Prime location at intersection of Hwy 22 and Hwy 329. Zoned R-2.

3300 W Highway 22, Crestwood

Listing courtesy of Semonin Realtors.

$499,900
2 Beds ⋅ 2 Baths ⋅ 1687337 MLS
Don't miss this unique opportunity to own a historic former plant nursery in the heart of Pewee Valley. Situated on a picturesque tract in Oldham County, this property offers a blend of charm, history, and untapped potential. The land features mature trees, open clearings, and remnants of its previous use, perfect for restoration or redevelopment. Whether you're looking to create a private estate, start a hobby farm, or reimagine the property for agricultural or residential use, this location offers endless possibilities. Enjoy the tranquility of country living with easy access to shopping, dining, and top-rated Oldham County schools. Zoned residential. Buyer to verify all zoning and development potential. Schedule your private showing today.

8725 Ash Ave Unit Lot 1, Pewee Valley

Listing courtesy of EXP Realty LLC.