Crestwood Homes with Entry Side Parking

Welcome home to 2003 OakShade Court, a spacious Craftsman-style home nestled on 1.35 acres in the desirable Grand Oaks subdivision of Crestwood. Located on a quiet cul-de-sac, this five-bedroom, three-and-a-half-bath home offers the perfect blend of comfort, space, and peaceful country living. The inviting open-concept layout is ideal for everyday living and entertaining, while the kitchen features beautiful granite countertops plus the added convenience of a first floor primary bedroom. The second floor offers 3 additional bedrooms and full bath. An added bonus is also a flex space that could be a play room or teen hangout. The finished walkout basement adds an additional family room, bedroom, and bath, perfect for overnight guests or anyone seeking a comfortable space of their own. Step outside onto the back deck and enjoy the wooded backdrop and tranquil sounds of a water feature from a pond on the neighboring property, creating a peaceful and relaxing backyard setting. A tractor garage provides convenient space for lawn equipment, tools, and additional storage. Grand Oaks residents also enjoy access to a neighborhood lake and pond with docks for fishing and relaxing by the water. Surrounded by natural beauty yet conveniently close to shopping, dining, award winning schools, and everyday amenities. This property offers room to spread out without sacrificing convenience.

2003 Oakshade Ct, Crestwood

$529,000

3 Beds ⋅ 3 Baths ⋅ 1731757 MLS

Discover the charm of this custom-built, one-owner home, lovingly maintained inside and out and situated on nearly 3.5 acres across two lots in a desirable Crestwood location. Surrounded by mature trees and beautifully landscaped grounds, this inviting property offers a peaceful setting with plenty of room to relax, garden, and enjoy the outdoors. Inside, the coveted first-floor primary bedroom suite offers the convenience and option of one-level living. The thoughtfully designed eat-in kitchen features a peninsula, roll-out shelving, a pull-out pantry, and abundant solid-wood cabinetry, creating a functional and welcoming space for everyday meals and entertaining. The main level also includes a comfortable living room, a separate dining room, a second full bathroom, and a cozy family room centered around a fireplace. Upstairs, two generously sized bedrooms and a full bathroom with a double vanity provide comfortable accommodations for family or guests. The finished basement expands your living options, with endless possibilities for a recreation room, home office, hobby area, or media space. Notable updates include HVAC replacement in 2024 and Andersen Renewal window replacements, adding to the home's appeal and long-term enjoyment. With its thoughtful design, versatile living areas, and nearly 3.5 acres to enjoy, this well-cared-for home offers a wonderful blend of comfort, privacy, and opportunity in sought-after Croftboro Farms. Come explore all this special property has to offer and envision making it your own!

2019 Montfort Cir, Crestwood

$3,000,000

4 Beds ⋅ 5 Baths ⋅ 1731647 MLS

Experience the absolute best of both worlds on this spectacular Custom Built Estate on 28.67 ACRES, bordering the New Clore Station Development - 4 BEDROOM, 5 BATH, 4773 SQ FT FINISHED ABOVE GROUND - Offering a private country setting, stretching entirely FROM HIGHWAY 329 TO THE 329 BYPASS - Vast acreage with PRIVATE LAKE & mature woods - ensuring total seclusion while keeping premier shopping, dining, and entertainment just around the corner - Stunning Lake Views in Every Direction - Designed & lovingly maintained by its original owner - Expansive covered front porch with wood ceiling - Brick walkways - Hand-crafted front staircase with custom millwork from a template designed exclusively for this home - Private Study/Music Room off entry - Formal Dining Room with custom wainscoting, columns, & extraordinary trim work - Butler's Pantry connects the Dining Room to the Kitchen - Enormous Gourmet Kitchen with double ovens, warming drawer, microwave, extensive custom cabinetry, appliance garage, sink & vegetable sink, wraparound island with abundant seating, & back staircase to the second floor - Separate Dining Area with vaulted wood ceiling, large enough for big gatherings, surrounded by windows with wooded & lake views - Access to the maintenance-free Deck, NEW in 2026 - Great Room with soaring two-story vaulted ceiling, hand-cut stone wood-burning fireplace with gas starter, Palladian window, & custom built-in bookcases - Double doors to a massive screened porch with a compass set in the floor, so you always know which way you're facing - Columned alcove leads to the Primary Suite, with room for a sitting area, office, or reading retreat; spa-inspired bath with large soaking tub, etched glass accents, shower, dual sinks, vanity, & an enormous walk-in closet - Upstairs, an oversized hallway overlooks the Great Room, ideal for a sitting area or study nook; Jack-&-Jill Bedrooms with shared bath, plus an Additional Bedroom & Full Bath - IN THE LOWER LEVEL 3,300 SQUARE FEET OF ADDITIONAL UNFINISHED LIVING SPACE - Highlights include a Fireplace, large Finished Bathroom with shower, plumbed for an additional Bath, steps with access to the oversized 3-car Garage, & direct access to a Private Patio, Handcrafted stone walls & steps—designed, carved and placed by the owner-builder--lead down to the back of the property, creating a truly remarkable outdoor setting - Additional features include: NEW CARPET in all 2nd floor bedrooms, Refinished Hardwood Floors throughout the first floor (2026) - First Floor Laundry Room with closet, outside entrance & washtub sink - Three HVAC systems - Pull Down Attic Steps in the Garage - House Generator - Smoking Porch - Oversized 3-Car Garage with extra depth & width, Large Turnaround Driveway - Circle Driveway - Private country driveway leading to a Barn with electricity & Silo. Perfectly situated easy access to I-71 - Custom-built, thoughtfully designed, & impeccably maintained - A rare opportunity to own a truly distinctive home in an outstanding location

6711 Highway 329, Crestwood

$589,900

4 Beds ⋅ 3 Baths ⋅ 1731588 MLS

Beautiful 4-bedroom ranch on 1.3 acres in Oldham County featuring an open-concept floor plan, vaulted ceilings, and a primary bedroom with direct deck access. Two additional bedrooms are located on the first floor. Enjoy the full front porch, sunroom, mature trees, and inground pool. The walkout basement offers a fourth bedroom, full bath, family room, and additional space ideal for a home gym. Solar system included. HSA Home Warranty included for added peace of mind. Don't miss this spacious home with exceptional indoor and outdoor living!

2010 Clarke Pointe Dr, Crestwood

$825,000

5 Beds ⋅ 5 Baths ⋅ 1731424 MLS

BRENTWOOD SUBDIVISION- Oldham County White brick, a walkout lower level, and a fenced corner lot in Brentwood. This two-story sits on 0.45 acres in Crestwood's highly sought-after Brentwood neighborhood. The kitchen has Cambria Quartz Counter and island under brass pendants, a gas range, a butler's pantry with a beverage refrigerator, and a walk-in pantry, opening to a great room with a gas fireplace and built-ins. Upstairs, the primary bath has a freestanding tub, a frameless glass shower, and a double vanity with backlit mirrors. The walkout lower level adds a media wall, a bonus room, and a full bath, with a covered patio, a covered deck, and a fully fenced yard outside. Brentwood amenities include a clubhouse, pool, and tennis courts in the Oldham County School District.

5800 Sumner Pl, Crestwood

$814,900

4 Beds ⋅ 4 Baths ⋅ 1731246 MLS

Welcome to 6300 Leyton Ct, located in the highly sought-after Brentwood neighborhood in Oldham County. Built in 2023 and situated on a spacious corner lot, this 4-bedroom, 3.5-bath home has been thoughtfully designed with upscale finishes and exceptional craftsmanship throughout. The main floor features beautiful engineered hardwood flooring, an open-concept layout, abundant natural light, a coffered ceiling in the living room, and a gas fireplace. Interior selections and design were completed by award-winning Lisa Lynn Designs, creating a timeless yet modern aesthetic. The gourmet kitchen is equipped with top-of-the-line KitchenAid appliances, custom cabinetry, quartz countertops, a 5-burner gas cooktop, and generous prep and storage space, including a coffee bar/butler's pantry area. The spacious primary suite offers a luxurious bath with dual vanities and a walk-in shower featuring body sprays. Upstairs, a convenient Jack-and-Jill bath connects two bedrooms, while the third bedroom includes its own private ensuite bath. Additional highlights include designer lighting fixtures, custom blinds, high-efficiency zoned HVAC, and an oversized 2-car garage. The unfinished walkout basement features 9-foot ceilings, plumbing for a future bathroom, and the potential to add a 5th bedroom and additional finished living space. Enjoy outdoor living from the oversized covered deck and covered patio overlooking the fully fenced backyard. Brentwood neighborhood amenities include a pool, clubhouse, and tennis courts, all conveniently located within the award-winning Oldham County School District.

6300 Leyton Ct, Crestwood

$845,000

6 Beds ⋅ 5 Baths ⋅ 1730853 MLS

With generous gathering spaces on all three levels and inviting covered porches, this beautifully maintained Brentwood home offers room to spread out and come together. Built in 2020, the home features more than 3,600 finished square feet, a main-level primary suite and thoughtful custom details throughout. The great room's coffered ceiling and gas fireplace with a reclaimed wood mantel create a welcoming centerpiece for the open main floor. The kitchen features custom cabinetry extending to the ceiling, granite and butcher block countertops, and a walk-in pantry with an appliance station. A custom bar area just off the kitchen includes a drink refrigerator for easy entertaining. A light-filled laundry room and mudroom with built-in storage add everyday convenience. The primary suite includes vaulted ceilings, direct backyard access, a spacious walk-in closet and a bath with heated floors, a deep soaking tub, dual vanities and a tiled shower with multiple showerheads. Upstairs are three bedrooms, two full baths and an exceptionally large bonus room with windows and a walk-in closet, offering flexibility for a den, additional bedroom or both. The finished lower level includes a family room with custom, built-in bunk beds and a guest bedroom with an en suite bath. Unfinished space provides expansion potential, and a safe room sits beneath the front porch. Covered front and rear porches, a fountain, a custom swing set and a level backyard extend the home's appeal outdoors. The rear patio is wired for a hot tub, and the front porch includes a 220-volt connection for an infrared heater. Posts at the rear of the double-wide driveway are ready for a basketball hoop. Newly planted evergreens will provide additional privacy as they mature. New custom exterior paint, irrigation and a three-car garage complete the property. Brentwood amenities include sidewalks, a clubhouse, pool, tennis and pickleball courts making this a friendly and desirable neighborhood.

6370 Clore Ln, Crestwood

$729,900

4 Beds ⋅ 4 Baths ⋅ 1730698 MLS

Welcome home to this custom built 3 story Victorian dream house in the highly sought after neighborhood of Grand Dell. An absolute vision of timeless elegance sitting on 4 luscious acres lined with trees! Prepare to be wowed by the most incredible lot available in the neighborhood with its long grande entrance off the road, and one of the largest rolling lots. Featuring an above ground pool, private garden house, extra detached garage and custom fenced garden with incredible panoramic views of your old Kentucky Home! This is a must see to believe available for the first time ever since its build in 30 years by its only owners. Your very own living dollhouse on a picturesque lot offering private glassed sunrooms and front porches to gaze at the stunning land that surrounds you! Inside features over 3000 finished square feet, 4 bedrooms and 4 baths with custom carpentry and gorgeous hardwoods throughout! Enormous updated kitchen with granite counter tops, beautiful handcrafted carpentry and cabinetry, and stainless appliances. In the great room, cozy up all winter long to the wood burning fireplace with surrounding built ins. Unique for its time offering 2 glassed in porches off the back and side of house made for all seasons to enjoy . Large first floor laundry room and 2 car attached garage! Upstairs you will find another bonus area serving many functions with 3 bedrooms, 2 full baths and that's not all! The third floor has been completely renovated with enormous family room or bedroom, hardwoods, vaulted ceilings with tons of natural light and own full bath providing a unique element of layout functionality for any buyers varying needs. Recently updated mechanicals throughout and extra detached garage for storage and land maintenance. Unfinished walkout basement providing tons of additional storage! The beautiful above ground pool overlooks the amazing views of the entire backyard with its own garden and garden house and pond! Truly a breath of heaven with this rare Crestwood Oldham Co. find! Schedule your private showing today! You don't want to miss this incredible opportunity to own your forever home!

4620 Grand Dell Dr, Crestwood

$635,000

4 Beds ⋅ 4 Baths ⋅ 1730624 MLS

Gorgeous, Well-Maintained Property! Nestled on a picturesque 1.82-acre lot in the Grand Dell neighborhood, this beautiful custom-built 4-bedroom, 3.5-bath home offers the perfect blend of spacious living, timeless design, and exceptional privacy. A dramatic two-story Great Room with a fireplace and walls of windows fills the home with natural light, while the formal Dining Room provides an elegant space for entertaining. The Kitchen is a chef's dream, featuring abundant cabinetry, generous counter space, a center island, and a sunny dining area overlooking the park-like backyard. A versatile Living Room or Home Office, inviting sunroom, convenient Laundry Room, and Half Bath complete the first floor. Upstairs, the spacious Primary Suite offers a relaxing retreat with a luxurious ensuite bath featuring double vanities, a soaking tub, separate walk-in shower, and ample closet space. Two additional bedrooms and a full bath complete the second level. The finished walkout lower level is designed for entertaining and everyday living, offering a large Family Room with a second fireplace, a Game Room with a wet bar and full-size refrigerator, a fourth bedroom, and a full bath—ideal for guests or multi-generational living. Outdoor living is just as impressive with an expansive deck, lower-level patio, and beautifully landscaped grounds surrounded by mature trees, creating a peaceful and private setting. Recent updates include a new septic system, chimney, and both fireplaces updated with new liners, inserts & sealed, new 2nd-floor ceiling fans in two bedrooms, new primary bath exhaust fan, fresh landscaping.

4740 Grand Dell Dr, Crestwood

$720,000

4 Beds ⋅ 4 Baths ⋅ 1730307 MLS

Opportunities like this do not come often: a four bedroom, three and a half bath, walk-out, on over four acres, two car attached garage, and separate 40' x 48' shop in Oldham County. Inside the house, you are welcomed into the spacious front foyer. The first floor has an eat-in kitchen with pantry, separate dining room, living room, office, beautiful half bath, and laundry room. As a bonus, there is a laundry chute from the second floor to the first floor laundry. Plus, the two car attached garage has extra space for storage too. The second floor has a large en suite space with walk-in closet, three other bedrooms, and an additional full bathroom. Also, the basement is amazing—with its bar, entertaining space, full bathroom, extra room, and storage, it provides extra space to play or rest. An incredible, stand-out feature of this property is the separate shop. It has its own, dedicated 12' wide concrete driveway. The door is 10' high by 20' wide. The shop is almost 2,000 square feet of heated space with endless possibilities. It has a fully concreted floor for high PSI strength, and it is completely insulated. The building has 200 amp service, with a 30 amp camper/trailer plug on the outside wall. If you are looking for a great outside, this has it. There is a front porch, back deck, and back patio coming from the basement walk-out. And, the land is an amazing 4.2 acres, which includes part of a shared pond that is viewable from the house. The views of the wildlife are a bonus to the serene setting. The property gives you an oasis spot while still being tucked back into a neighborhood. In terms of location, it is very close to where Highway 53 and Highway 22 meet, providing quick access to many great amenities in LaGrange and beyond, while still feeling tucked away. Make an appointment to make this wonderful property your own.

4703 Grand Dell Dr, Crestwood

$750,000

5 Beds ⋅ 5 Baths ⋅ 1730104 MLS

Space is a luxury and at 1911 Clarke Pointe Drive, there is an extraordinary amount of it in all the right places. Set on just over an acre in Crestwood's Clarke Pointe, this impressive residence delivers more than 3,000 square feet of living space on the main level alone, an oversized 3 car garage, and an expansive finished walkout lower level offering an entirely additional dimension for entertaining, recreation and everyday life. From the moment you enter, the home feels substantial yet inviting. Hardwood floors, vaulted ceilings, designer finishes and beautifully updated baths set the tone, while oversized living spaces provide the freedom to gather on a grand scale without sacrificing warmth or comfort. The home has also been repainted over time, including recent paint updates on portions of the main level, creating a fresh and well-cared-for presentation. At the heart of the home is a kitchen designed to bring people together. Granite countertops, abundant cabinetry, updated appliances and a generous center island create an impressive workspace, while the oversized casual dining area easily accommodates family and friends. A walk-in pantry and spacious laundry room add exceptional everyday functionality, and the adjoining formal dining room provides an elegant setting for holidays and special occasions. The vaulted great room is centered around a beautiful fireplace and flows naturally to the expansive rear deck, where peaceful views across the surrounding Oldham County landscape create a picturesque backdrop for morning coffee, evening dinners or weekends spent entertaining outdoors. The landscaping was refreshed approximately two years ago, further enhancing the home's acre-plus setting and outdoor spaces. The main-level primary suite offers a private retreat of its own, highlighted by a beautifully renovated bath with dual vanities, tiled shower and soaking tub. Additional bedrooms and baths complete a remarkably spacious main floor—making the home especially appealing for those seeking the convenience of predominantly one-level living without compromising on size. Then there is the walkout lower level. Far more than simply additional finished space, this level lives almost like a second home. An additional bedroom with a full-size window and walk-in closet is joined by a spacious recreation and billiards area, family room with a second fireplace, full kitchen and dining area, additional bath, game or craft space, workshop and dedicated safe room. French doors open directly to the large rear patio and backyard, seamlessly connecting another level of indoor and outdoor living. Beyond its impressive living spaces, several meaningful improvements add to the home's comfort and convenience. The furnace was replaced approximately three years ago, the high-capacity water heater approximately five years ago, and an EV charger has been installed in the garage—an especially convenient addition for today's household. Offering exceptional scale, extensive main-level living, multiple entertaining spaces, thoughtful updates and an acre-plus setting within the Oldham County School District, 1911 Clarke Pointe Drive is the kind of home that is increasingly difficult to find - one with the space to gather, the flexibility to evolve and the setting to enjoy it all.

1911 Clarke Pointe Dr, Crestwood

$3,200,000

4 Beds ⋅ 3 Baths ⋅ 1729405 MLS

Situated across 44.4 acres of pristine Oldham County land, this exceptional property delivers the best of both worlds: a private, elegant residence for gracious country living along with a fully operational, revenue-ready equestrian center built to professional standards. Only 1.5 miles from Exit 14 on I-71 and less than 20 minutes to Downtown Louisville, this farm's location is truly rivaled by none, making it the perfect opportunity for breathtaking acreage in the heart of horse country without compromising on convenience or location. Whether seeking a personal sanctuary with the option to lease out a best-in-class training facility, or a hands-on horseman's dream with room to expand a boarding and lesson business, this estate is designed to inspire awe and appreciation from equestrian enthusiasts at every turn. Tucked between scenic paddocks and mature trees, the 5,000+ sq. ft brick farmhouse features 4 bedrooms and 2.5 baths, 3-car garage, in-ground pool, and stocked 1/3-acre pond. Just off the main road for convenient client access, the equestrian center has been designed to meet the highest of standards, with a main barn holding 16 comfortable stalls with compacted limestone bases and full mats, while the adjoining 210' x 80' indoor arena is outfitted with Trutex footing, mirrors, and 10 large sliding windows for airflow. Supporting spaces include a lockable feed room, dedicated hay storage, and climate controlled tack room with washer/dryer, 16 individual cabinets, sink, and additional storage. The added bonus of a climate-controlled viewing lounge with bathroom makes it the perfect place to spectate the indoor riding arena on even the hottest summer days. For additional convenience, an on-site 30-yd waste container makes disposing of manure hassle-free, while the barn's AT&T Fiber connection, whole-barn watering system with two wash stalls with hot and cold water, and first class security system elevate the usability of the space. The property's second barn adds 6 matted stalls, hay loft with capacity for over 1,000 bales, tack/storage room with instant hot water, and machinery overhang, along with flexible space that could convert to additional stalls. Beyond the barns, riders will appreciate the 9 rolling paddocks (6 of which feature automatic waters for added convenience, one featuring a 12 x 14 run-in shed) with iconic four-board fencing, 250' x 125' outdoor sand arena, field with cross-country jumps for eventing and conditioning work, and winding wood trails along the perimeter of the property.

6801 Old Zaring Rd, Crestwood

Crestwood Homes with Entry Side Parking

Newest Crestwood Homes with Entry Side Parking

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