8 - Douglas Hills / Hurstbourne / Middletown / Anchorage Homes under $400,000

8 - Douglas Hills / Hurstbourne / Middletown / Anchorage Homes under $400,000

Welcome to the enchanting region of Douglas Hills, Hurstbourne, Middletown, and Anchorage, nestled in the heart of Jefferson County, Kentucky. This vibrant area is renowned for its picturesque neighborhoods, lush landscapes, and a warm sense of community that welcomes families, professionals, and retirees alike.

Douglas Hills, with its charming tree-lined streets, offers a serene suburban atmosphere perfect for those seeking tranquility without sacrificing convenience. Hurstbourne is known for its beautiful parks and recreational facilities, providing ample opportunities for outdoor activities and family fun. Meanwhile, Middletown boasts a rich history and a lively downtown area filled with delightful shops and eateries, making it a favorite among locals. Lastly, Anchorage stands out with its quaint, small-town feel and a strong sense of community spirit, making it an ideal place to call home.

One of the most appealing aspects of this region is the availability of homes under $400,000. Whether you're a first-time homebuyer or looking to downsize, you’ll find a diverse selection of charming single-family homes, modern townhouses, and cozy condos that fit your budget. This affordability allows you to enjoy the benefits of suburban living without compromising on quality or comfort.

With excellent schools, convenient access to shopping, dining, and major highways, Douglas Hills, Hurstbourne, Middletown, and Anchorage offer a perfect blend of lifestyle and affordability. Come explore the possibilities and discover your dream home in this delightful Kentucky enclave!

Newest 8 - Douglas Hills / Hurstbourne / Middletown / Anchorage Homes under $400,000

105 Beckley Woods Dr, Louisville
$400,000
3 Beds ⋅ 2 Baths ⋅ 1730839 MLS
Welcome to 105 Beckley Woods Dr, ideally located in the established Beckley Woods neighborhood in Middletown! This 3-bedroom, 2-bath home offers a comfortable and functional layout with approximately 1,709 square feet of finished living space, plus an unfinished basement providing excellent potential for additional living, recreation, or storage space. The inviting living areas include a fireplace, while the attached two-car garage adds everyday convenience. Outside, enjoy a spacious, tree-lined yard with plenty of room to relax, entertain, garden, or play. Conveniently located near shopping, dining, parks, and major roadways, this home combines and established neighborhood setting with easy access to everything the Middletown area has to offer. Bring your personal touches and make this Beckley Woods home your own!

105 Beckley Woods Dr, Louisville
513 Cheskirk Pl, Louisville
$379,500
3 Beds ⋅ 3 Baths ⋅ 1730820 MLS
Welcome to easy living in desirable Douglass Hills! This inviting ranch-style home offers comfortable one level living with additional finished space in the lower level, all in a community filled with amenities. The welcoming entry foyer opens to a formal living room and dining room, creating an ideal flow for both everyday living and entertaining. The family room features a cozy fireplace and direct access to the rear deck, providing a wonderful spot to relax or enjoy outdoor gatherings. The kitchen offers an abundance of cabinetry and plenty of storage.. For those who prefer a main level laundry area, the laundry was previously in this area and the hookups can likely be moved back to their original location. The spacious primary suite includes a dressing area and private primary bath, while two additional bedrooms and a full bath complete the main level. The finished lower level adds valuable flexibility with a comfortable family room plus an additional finished room with a closet—perfect for a home office, craft room, hobby space or guest area. Enjoy the many amenities of Douglass Hills, including a community pool, playground, tennis and volleyball facilities, two parks, and a gazebo available for rental and community events. The shingles were replaced in March 2026, and the seller is offering a one-year home warranty for added peace of mind. Conveniently located near shopping, dining, parks and everyday amenities, this home offers the space, flexibility and community lifestyle you've been looking for. Don't miss your opportunity to make this your new home. Schedule your private showing today!

513 Cheskirk Pl, Louisville
209 S Dorsey Ln, Louisville
$249,000
2 Beds ⋅ 2 Baths ⋅ 1730661 MLS
SELLER IS OFFERING AN APPLIANCE ALLOWANCE! Freshly updated paint and flooring and easy to enjoy, this first-floor 2-bedroom, 2-bath condo in 40223 is ready for its next owner. New flooring and fresh paint throughout give the home a bright, welcoming feel. The spacious living room opens to the dining area, with a convenient kitchen nearby. The primary bedroom has its own full bath, while the second bedroom and bath offer room for guests or a home office. Step out to the private back patio for a quiet morning or a relaxing evening. A 1-car garage adds everyday convenience, and shopping, dining, and major interstates are just minutes away.

209 S Dorsey Ln, Louisville
1326 Peaceful Way, Louisville
$399,990
4 Beds ⋅ 3 Baths ⋅ 1730628 MLS
Welcome to this Aspen II at 1326 Peaceful Way in Louisville, Kentucky, offering spacious living areas, flexible rooms, and thoughtfully selected modern finishes. With four bedrooms, a private study, an upstairs loft, and an open-concept main level, this two-story home provides plenty of room for everyday living, entertaining, working from home, and creating lasting memories.

1326 Peaceful Way, Louisville
431 Logsdon Ct, Douglass Hills
$185,000
2 Beds ⋅ 2 Baths ⋅ 1730617 MLS
Quiet community that backs up to Douglass Hills Park. Two Bedroom, Two bath condo with in unit laundry. A carpet allowence is being offered.

431 Logsdon Ct, Douglass Hills
1102 Timber Oak Dr, Louisville
$380,000
4 Beds ⋅ 2 Baths ⋅ 1730591 MLS
1102 Timber Oak Dr combines a convenient Middletown location with inviting interior features, multiple living spaces, and an entertaining-friendly backyard. Set on a corner lot in the walkable Woodcroft neighborhood, this home is located just outside Douglas Hills and Plainview and offers convenient access to Warren Walker Park, tennis courts, and sand volleyball—without the need to join an HOA. Inside, bamboo hardwood flooring and new carpet create a fresh, comfortable feel throughout. The functional brick fireplace adds warmth and character to one of the home's living areas, while the additional living spaces offer flexibility for relaxing, gathering, working from home, hobbies, or hosting guests. Outside, thoughtfully arranged landscaping provides curb appeal, while the backyard offers room to grill, garden, play, or unwind. The corner-lot setting adds to the home's overall presence and inviting outdoor setting. With its convenient location, versatile layout, nearby recreation, and well-designed outdoor space, 1102 Timber Oak Dr offers a great opportunity to enjoy life in the Woodcroft neighborhood.

1102 Timber Oak Dr, Louisville
1202 Pickings Pl Unit 202, Louisville
$215,000
2 Beds ⋅ 2 Baths ⋅ 1730588 MLS
The bright and airy great room features a vaulted cathedral ceiling, cozy fireplace with gas logs and access to a private balcony. There is a nice sized dining area which offers plenty of room for entertaining and flows into the galley- style kitchen and is open to the large great room. Luxury vinyl plank flooring extends through the foyer, dining room, kitchen and laundry room while updated carpeting adds warmth and comfort to the great room and both bedrooms. The spacious primary bedroom offers lots of natural light and features a partially vaulted ceiling and a large walk-in closet. The second bedroom also offers excellent natural light and its own large walk-in closet. With 2 full baths, an in-unit laundry and updated flooring throughout, this home is comfortable fresh and move in ready. There is an additional storage unit on the same floor. It is conveniently located in the hallway just outside the unit. Swan pointe residents enjoy wonderful community amenities including a clubhouse, swimming pool fitness room and tennis courts.

1202 Pickings Pl Unit 202, Louisville
10513 Eagle Pines Ln, Louisville
$399,900
3 Beds ⋅ 2 Baths ⋅ 1730585 MLS
Nestled in the coveted Pinehurst Green community, this tranquil patio home offers the space, layout, and lifestyle you've been waiting for! With 2483 total square feet, 3 bedrooms, and 2 bathrooms, this home offers a large yet warm and inviting atmosphere. Designed for both everyday relaxation and effortless entertaining, you are welcomed by a covered front porch into an open floor plan, beginning with a vaulted great room with warm, corner fireplace. Seamlessly into the spacious dining area and kitchen, you have beautiful white cabinetry, quartz countertops and gorgeous backsplash, a breakfast bar for casual seating, and tons of storage for all your culinary needs. An adjoining all-season sunroom provides a tranquil retreat filled with plantation shutters that allow natural light to pour in and an outdoor view year-round, perfect for morning coffee or unwinding at the end of the day. The split bedroom layout of the home provides two generously-sized bedrooms just off the sunroom and a hall bathroom, while the primary suite is at the opposite end of the home giving you extra privacy, an ensuite bath and a huge walk-in closet. Beyond this area is your laundry room which conveniently connects to a hallway with access to your outdoor patio with a privacy fence, as well as entrance into your attached 2-car garage. Complemented by a stairway leading to a generous attic area with flooring, you have a massive amount of room for storage and organization. The Pinehurst Green community provides a peaceful vibe and great amenities, including a clubhouse, fitness room, and outdoor pool. Conveniently located near shopping, dining, and major roadways in Middletown, St. Matthews, and Lyndon, this home truly delivers on both lifestyle and location, making it one of Louisville's most desirable patio home communities.

10513 Eagle Pines Ln, Louisville
902 La Fontenay Ct, Louisville
$132,500
2 Beds ⋅ 2 Baths ⋅ 1730518 MLS
Welcome home to this updated 2 Bedroom, 2 Bath Condo offering low maintenance living conveniently located in Middletown. Recent updates include new luxury vinyl plank flooring, new carpet, fresh paint and new faucets and light fixtures. The generous living room area opens through sliding glass doors to a private covered patio. The adjoining dining area flows easily into the kitchen, where convenient pass-through keeps the space open and connected for everyday living and entertaining. Both bedrooms offer comfortable living space. Enjoy the benefits of condo living with an HOA that includes gas heat, water, trash, sewer, exterior maintenance, snow removal and master insurance. Community amenities include a clubhouse , tennis court and pool. Move in ready.

902 La Fontenay Ct, Louisville
10605 Sycamore Trail, Louisville
$229,000
2 Beds ⋅ 2 Baths ⋅ 1730506 MLS
Welcome to 1605 Sycamore Trail in "The City of Sycamore". Great location near Middletown ! A Well maintained community. Convenient easy access to any area. Townhouse style condo unit, 2 bedrooms, 1.5 baths, partially fin. bsmt, fireplace, two car carport, fenced in patio with rear entry access to the unit. Community has a built in pool, clubhouse, tennis/pickleball court. A Modern living floor plan with the opportunity to create your own personal style and space. Immediate occupancy available. https://www.cityofsycamore.net/news/

10605 Sycamore Trail, Louisville
11905 Wetherby Ave, Louisville
$250,000
3 Beds ⋅ 1 Baths ⋅ 1730429 MLS
Welcome to 11905 Wetherby Ave, a beautifully renovated 3-bedroom, 1-bath ranch nestled in a quiet, established neighborhood just off Evergreen Road in the heart of Middletown. This move-in ready home offers modern updates while maintaining the comfort and functionality of single-level living. Inside, you'll find a bright, inviting layout with stylish finishes throughout. The spacious backyard provides plenty of room for entertaining, gardening, pets, or simply relaxing outdoors, while the attached 1-car garage adds everyday convenience. Centrally located near shopping, dining, parks, schools, and major highways, this home combines peaceful neighborhood living with easy access to everything Louisville has to offer. Whether you're a first-time homebuyer, downsizing, or looking for a turnkey investment, this home is one you won't want to miss. Schedule your private showing today!

11905 Wetherby Ave, Louisville
125 Dorsey Station Rd, Louisville
$217,900
2 Beds ⋅ 3 Baths ⋅ 1730325 MLS
What a DEAL ! Not many town homes come on the market around here. This 2 bed/ 2bath has 1181 sq ft of living space. First floor has Kitchen, living room with fireplace, laundry and powder room. There are sliding glass doors off the living room leading to your private patio overlooking a park like setting. The second floor has 2 private suite's and both have large closets and their own private bathrooms. There is a pool and tennis courts close to the town home and best thing is there are NO rental units. This is off Shelbyville Road at Dorsey Rd and close to loads of shopping and bus line. HOA fee covers Master Ins., Lawn care and snow removal, grounds maintenance, pool and Tennis courts, garbage.

125 Dorsey Station Rd, Louisville
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