Winchester Homes under $150,000

Winchester Homes under $150,000

Welcome to Winchester, Kentucky, a charming city nestled in the heart of Clark County, where southern hospitality meets vibrant community spirit. Known for its rich history and picturesque landscapes, Winchester offers a unique blend of small-town charm and modern convenience. With a population that cherishes its heritage, residents enjoy a welcoming atmosphere that makes it easy to feel right at home.

One of the standout features of Winchester is its affordability, particularly in the housing market. For those searching for homes under $150,000, this city presents a wealth of opportunities. Whether you’re a first-time homebuyer, a growing family, or looking to downsize, Winchester has a variety of options that cater to diverse needs and budgets. From cozy bungalows to quaint cottages, you’ll find properties that reflect the character of this delightful community.

The local amenities are plentiful, with parks, shops, and dining options just a stone’s throw away. The vibrant downtown area is perfect for leisurely strolls, and the surrounding countryside offers stunning views and outdoor activities for nature lovers. With excellent schools and a strong sense of community, Winchester is an ideal place to create lasting memories.

Imagine waking up in a charming home that fits your budget while enjoying all the benefits of living in a warm, inviting city. Winchester, KY, is not just a place to live; it’s a place to thrive. Discover your dream home today and experience the beauty and warmth of Winchester living!

Newest Winchester Homes under $150,000

208 Buffalo Trce, Winchester
$149,000
2 Beds ⋅ 3 Baths ⋅ 26029736 MLS
Multiple offers have been received on this property. Please submit your offer before the deadline shown below, or If your buyer would like to make any revisions to their submitted offer, follow the steps below: Navigate to VRM Properties (web address in private remarks) Sign In with Username & Password Click the Menu Icon (the 3 orange bars in the upper right side of the screen) Click "My Offers" and Submit your revisions by clicking on the Next Action: Submit Highest & Best link For detailed instructions, please see the attached Multiple Offers Job Aid attached to this listing. The Highest & Best deadline for revisions is 1:00PM Central Time on 10-30-2026. If no revisions are submitted by the deadline, the existing offer will be considered your final Highest & Best offer. Ranch style home on full, finished, walk out basement. Home features entry foyer, primary bedroom with adjoining bath, second full bath off the foyer, Great room style kitchen and living room area and a formal dining area/den. Lower level is finished with half bath, one bonus room with closet and second bedroom with windows but no closet. as well as a family room area. Additional bonus is the unfinished storage/storm shelter area. Home has off street parking, backyard deck and is ready for a new owner. This property has discoloration. Will be REHAB type loan

208 Buffalo Trce, Winchester
121 Ralston Ln, Winchester
$56,700
3 Beds ⋅ 1 Baths ⋅ 26029234 MLS
INVESTMENT OPPORTUNITY — BUILD YOUR VISION! The existing home is in poor condition and may be suitable for renovation or a tear-down project. The property consists of almost 1/2 Acre (.45 acre) with a newer metal building 20 X 25. An excellent opportunity for investors, builders, or buyers looking to create something new! This could be an excellent place for storing equipment, boats, RVs, or other recreational toys! 1,000-gallon septic system installed in 2023.

121 Ralston Ln, Winchester
3208 Ford Hampton Rd, Winchester
$135,000
2 Beds ⋅ 1 Baths ⋅ 26023193 MLS
Set on a half-acre in a rural Winchester setting, this 2-bedroom, 1-bath home offers an efficient one-level layout with approximately 807 square feet of living space. The eat-in kitchen provides a comfortable spot for everyday meals, while main-level laundry hookups add convenience. Front and rear porches extend the living space outdoors and offer places to enjoy the surrounding trees, countryside, and views. A metal roof adds practicality, and the property's location near the Kentucky River provides easy access to one of the area's notable natural features. Whether you're looking for a primary residence, weekend getaway, or a smaller property with a little room around it, 3208 Ford Hampton Road offers a straightforward home in a scenic rural setting.

3208 Ford Hampton Rd, Winchester
16 Denny Ave, Winchester
$58,500
3 Beds ⋅ 1 Baths ⋅ 26022585 MLS
Well priced and well located, 16 Denny Avenue is conveniently located near Eugene Gay Splash Park, downtown Winchester, shopping and schools. Home features 1152 sq ft with 3 bedrooms, 1 full bath, eat in kitchen and living room. Enclosed porch is located on front of house. Upgrades include laminate flooring, ductless heating and cooling and roof. Property has been tenant occupied and is sold as is. No repairs.

16 Denny Ave, Winchester
404 Mount Vernon Dr, Winchester
$124,000
2 Beds ⋅ 2 Baths ⋅ 26005794 MLS
Ready to Stop Renting? Your Opportunity Is Here Step into the comfort and freedom of homeownership with this spacious, well maintained 2-bedroom, 2-bath modular home — and yes, the lot is included. An attached room addition provides even more flexibility, easily adaptable into a third bedroom, home office, hobby room, or bonus space to suit your lifestyle. --- Interior Highlights • 2 full bathrooms • Large walk in shower • Wheelchair ramp for easy accessibility • Generous closet space throughout • Ample kitchen counter space • Clean, comfortable, and truly move in ready --- Exterior Features • Large corner lot offering extra privacy • Parking for up to 4 vehicles • Outbuilding for additional storage • Equipped with a Generac backup generator for peace of mind during outages --- This home offers affordable living without compromise—space, accessibility, convenience, and the security of owning your own land. $149,000

404 Mount Vernon Dr, Winchester
122 Callaway Street Se Callaway Street, Winchester
$124,500
2 Beds ⋅ 1 Baths ⋅ 26000228 MLS
Investment Opportunity or Perfect Starter Home This charming 2-bedroom, 1-bath property is full of potential! With a strong rental history and an excellent lease track record, it's ideal for investors or first-time buyers. The home requires only light maintenance, and the seller is even willing to fund minor repairs. Don't miss your chance to own a property with great value and endless possibilities! Property is AS IS! Bring me a offer.

122 Callaway Street Se Callaway Street, Winchester
563 Constitution Dr, Winchester
$99,500
2 Beds ⋅ 2 Baths ⋅ 26012893 MLS
Affordable housing! Check out this newly remodeled and updated home! 2 bedroom, 2 full bath! All new flooring, cabinets, vanities, and so much more! No lot rent here! You will own the lot as well, making this a great option for starter, downsizing, investment property (previously rented for $925), or just an affordable home. Nice covered porch, 2 storage sheds, brand new metal roof! $150 per month HOA fee covers your water, sewer, trash, and common area maintenance. Property is under a contingent contract with kick out clause.

563 Constitution Dr, Winchester
1860 Ford Rd, Winchester
$74,950
2 Beds ⋅ 1 Baths ⋅ 26004497 MLS
Freshly cleaned and ready for its next owner, this property offers exceptional potential. The spacious 1,800 sq. ft. block garage provides a solid foundation for countless uses — from a workshop or storage facility to a future business or hobby space. An older trailer is also located on the property. It will require a full renovation or removal, giving you the freedom to redesign the space exactly as you envision. Whether you're looking for a project, investment opportunity, or a versatile property with room to grow, this location delivers endless possibilities.

1860 Ford Rd, Winchester
65 Fitch Ave, Winchester
$139,900
3 Beds ⋅ 2 Baths ⋅ 26013935 MLS
Lovely older home, located witin waking distance to collage park whice offers Pickle Ball, Pool, Tennis, play gound and Walking Trail, also walking distance to Historic Downtown Winchester, with a little love house brings large rooms and a nostlogic atmosphire, take a look, view today, this a a great price for 3 bedrooms, 1 1/2 baths, nice back yard, with parking, call today! Selling "AS IS", inspections welcome, the are no utilties on at the present, Estate Please make sure all doors are locked when you leave, buyer to verifye size of home & Lot

65 Fitch Ave, Winchester
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