Crestwood Homes with Entry Side Parking

Crestwood Homes with Entry Side Parking

Welcome to Crestwood, Kentucky, a charming city nestled in the heart of Oldham County. Known for its picturesque landscapes and friendly community, Crestwood offers a perfect blend of suburban tranquility and easy access to urban amenities. Just a short drive from Louisville, residents enjoy the best of both worlds—serene living paired with the vibrancy of city life.

Crestwood is characterized by its beautiful neighborhoods, where tree-lined streets and well-maintained parks create an inviting atmosphere. Families are drawn to the area for its excellent schools, making it a fantastic place to raise children. The community is active and engaged, with various local events and activities that foster a strong sense of belonging among residents.

One of the appealing features of homes in Crestwood is the availability of properties with entry side parking. This thoughtful design not only enhances curb appeal but also provides convenient access to your home, making it easier for families and guests to come and go. These homes often boast spacious interiors, perfect for entertaining, while the side parking allows for additional vehicles without compromising on outdoor space.

Whether you're a first-time homebuyer or looking to settle down in a welcoming community, Crestwood has something for everyone. Explore the charm of this delightful city and discover your dream home with entry side parking, where comfort and convenience meet in a vibrant neighborhood setting. Experience Crestwood—where community spirit thrives and every day feels like home.

Newest Crestwood Homes with Entry Side Parking

4620 Grand Dell Dr, Crestwood
$699,900
4 Beds ⋅ 4 Baths ⋅ 1732653 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
6311 Breeze Hill Rd, Crestwood
$680,000
4 Beds ⋅ 5 Baths ⋅ 1732372 MLS
Discover refined living at 6311 Breeze Hill Road in Crestwood. This stately two-story residence offers 4 bedrooms, 4 full baths and 1 half bath, complemented by a beautifully finished walkout lower level. Gleaming hardwood floors grace the first floor, where the great room is anchored by an elegant gas fireplace. The primary suite is a true retreat, with a generously proportioned bedroom, an expansive walk-in closet and a spacious ensuite bath. Upstairs, three additional bedrooms include two connected by a Jack-and-Jill bath and one with its own private ensuite. The finished walkout basement offers a second great room with its own gas fireplace and seamless access to the grounds, an ideal setting for entertaining, guests, fitness or a private office. An impressive 3-car attached garage plus a separate 2-car detached garage offer exceptional space for collector vehicles, a workshop or storage. Outdoors, the deck overlooks a tranquil, shaded lot. Arrange your private showing today. Briar Hill Park is in the front of the neighborhood. It offers a playground, tennis/pickleball courts, basketball courts, hiking and biking trails.

6311 Breeze Hill Rd, Crestwood
2003 Oakshade Ct, Crestwood
$689,900
5 Beds ⋅ 4 Baths ⋅ 1732132 MLS
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
2019 Montfort Cir, 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
6711 Highway 329, 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
2010 Clarke Pointe Dr, 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
5800 Sumner Pl, 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
6300 Leyton Ct, 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
4703 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
7308 Kavanaugh Rd, Crestwood
$399,000
3 Beds ⋅ 2 Baths ⋅ 1729037 MLS
You lucked out, we're back on the market!! Updated, move-in ready, and sitting on nearly half an acre in highly sought-after Crestwood—time to move quick. This 3-bedroom, 1.5-bath brick ranch gives you the best of both worlds: the charm and solid construction of an established home, paired with thoughtful updates throughout. The kitchen and full bathroom have both been beautifully renovated with modern finishes while preserving the warmth and character that makes an older home so special—the kind of details and personality you just don't find in a new build. Fresh paint throughout ties it all together and makes the home truly feel move-in ready. One of the best surprises is the HUGE additional living space, filled with natural light and anchored by a beautiful brick fireplace. Two cozy window seats add even more charm (and might just become your favorite spots in the house). Whether you picture curling up with a book, cozy movie nights by the fireplace, a playroom that doesn't take over the rest of the house, or a space made for hosting a crowd, this room is something special. And there's still more space downstairs. The partially finished basement has been refreshed with brand-new LVP flooring and newly carpeted stairs, giving you even more flexibility for a home office, gym, hobby space, second hangout area, or whatever else your lifestyle calls for. Outside, the sellers have kept the improvements going with a new front deck and poured concrete patio out back. The fenced backyard sits on a generous .4-acre lot, giving you plenty of room for kids, dogs, gardening, entertaining, or simply enjoying a little extra breathing room. With a desirable Crestwood location, classic brick construction, a first floor primary and laundry room, thoughtful updates, multiple living spaces, and a backyard you'll actually want to use, this home brings together a combination that's getting harder and harder (near impossible) to find. Modern where it matters, full of character where it counts, and already updated so you can simply move in and make it yours. You'd better come see it today!

7308 Kavanaugh Rd, Crestwood
5700 Old Floydsburg Rd, Crestwood
$599,900
5 Beds ⋅ 3 Baths ⋅ 1728908 MLS
Seller is offering $10,000 towards rate buydown or closing costs with an accepted offer. If you've been searching for newer construction with acreage in Crestwood, 5700 Old Floydsburg Road offers a combination that's becoming increasingly difficult to find. Built in 2023 and situated on 1.30 acres, this 5-bedroom, 3-bath home offers plenty of space along with a layout that provides some interesting possibilities for its next owner. With few neighboring homes in sight and a privacy fence surrounding much of the property, the homesite offers a sense of separation that's hard to duplicate in a traditional neighborhood. Inside, you'll find generous living space and a large primary bedroom with plenty of room to create a comfortable retreat. Multiple bedrooms provide options for family, guests, a home office, hobbies, or whatever best fits your lifestyle. Upstairs may be one of the home's most versatile spaces. An expansive open loft-style room with its own full bath could function as a second primary suite, private guest quarters, a space for extended family, or an oversized bedroom with its own sitting or living area. For buyers looking for a home that can accommodate different living arrangements under one roof, this space opens up some great possibilities. Outside, the 1.30-acre lot gives you something that's increasingly hard to come by this close to Crestwood's everyday conveniences—room. Room for pets, a garden, outdoor entertaining, hobbies, or simply a little more distance between you and neighboring homes. A deck and separate sunroom add even more usable space, while the side-entry garage and separate outbuilding provide additional room for vehicles, lawn equipment, tools, storage, or recreational gear. The location keeps shopping, dining, schools, and everyday necessities within easy reach, while the acreage and limited neighboring homes give the property a character all its own. Five bedrooms, three full baths, 1.30 acres, newer construction, an outbuilding, and the potential for two separate primary suites—all in Crestwood. 5700 Old Floydsburg Road offers plenty of space and plenty of possibilities for its next owner.

5700 Old Floydsburg Rd, Crestwood
4402 Abbott Grove Dr, Crestwood
$549,900
4 Beds ⋅ 2 Baths ⋅ 1728727 MLS
Set on 1.04 acres in Crestwood with Oldham County Schools, this brick ranch keeps everyday living on one level. The great room rises to a vaulted ceiling with arched transom windows and a fireplace framed by floor to ceiling built-ins, and a separate living room means everyone gets their own space. The kitchen pairs granite counters and hardwood floors with a bar-height peninsula, gas range, and eat-in area, with a formal dining room off the foyer. A split plan puts the primary on its own side of the house, away from the secondary bedrooms, with a walk-in closet, jetted tub, tiled glass shower, and double vanity. The walkout basement adds a fourth bedroom and family room opening to the patio. Updated HVAC, fresh paint inside and out, newly sealed drive, deck over a level yard.

4402 Abbott Grove Dr, Crestwood
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