Homes for Sale near Caldwell County Middle School

• 

  

  

  /35

  $650,000

  • 2 Beds
  • 3 Baths
  • 1,773 Sq Ft

  762 Pleasant Valley Rd, Princeton, KY 42445

  This stunning, custom built home has character galore! Everything has been tastefully designed and crafted to provide the feel of a rustic, log home retreat. The logs, inside and out, are actually cast cement! From the soaring ceilings of the living room to the custom made cabinets, masonry work and the beautiful, live edge countertop you will be wowed from the moment you enter! The primary suite

  

  Ryals Farless

  Farless Realty

  (270) 518-2544

  762 Pleasant Valley Rd, Princeton, KY 42445
• 

  

  

  /22

  $270,000

  • 3 Beds
  • 2 Baths
  • 1,430 Sq Ft

  364 Farmersville Rd, Princeton, KY 42445

  This 3 bedroom, 2 bath home is just outside the city limits and is move-in ready! It offers an updated interior with newer flooring, fresh paint, updated bath, and HVAC & generator that are just a couple years old! Outside you'll find a relaxing covered patio to enjoy your afternoons overlooking the large 1.74 acre yard! There is an attached, 2 car garage AND a detached, 2 car garage! Just a

  

  Ryals Farless

  Farless Realty

  (270) 545-5181

  364 Farmersville Rd, Princeton, KY 42445
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  /33

  $180,000

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft

  613 Madisonville St, Princeton, KY 42445

  This 3 bedroom, 2 bath home is recently updated and move-in ready! The exterior provides a new roof, vinyl windows, gravel drive and a new concrete back porch. The interior of the home offers an unfinished basement, new flooring throughout, fresh paint, new kitchen cabinets and countertops, updated fixtures, new water heater, new hvac unit and an enclosed front porch. The only thing left to do is

  

  Ryals Farless

  Farless Realty

  (270) 751-6633

  613 Madisonville St, Princeton, KY 42445
• 

  

  

  /33

  $170,000

  • 3 Beds
  • 2 Baths
  • 1,314 Sq Ft

  201 W Sandra Dr, Princeton, KY 42445

  This 3 bedroom, 2 bath home is move-in ready! Outside you'll find a covered front porch, covered patio, fenced back yard, carport, an outbuilding with concrete floor and electricity and a large, corner lot. The interior of the home offers updated flooring, Fresh paint, vinyl windows, equipped kitchen and a washer & dryer. This one-level home provides an excellent opportunity fort most any buyer!

  

  Ryals Farless

  Farless Realty

  (270) 398-6944

  201 W Sandra Dr, Princeton, KY 42445
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  /45

  $370,000

  • 3 Beds
  • 2 Baths
  • 2,834 Sq Ft

  330 Alexander Rd, Dawson Springs, KY 42408

  Nestled in the woods of the hills overlooking Lake Beshear is this cozy 3 bedroom, 2 bath home. Tons of privacy, yet just up the hill from all the fun Lake Beshear has to offer. The main floor provides a large primary bedroom, walk-in closet, renovated bathroom, equipped kitchen and living room. Upstairs offers 2 more bedrooms, full bath and a large finished bonus room perfect for storage or

  

  Ryals Farless

  Farless Realty

  (270) 817-6435

  330 Alexander Rd, Dawson Springs, KY 42408
• 

  

  /30

  $684,000

  0 Donahue Rd, Princeton, KY 42445

  This sprawling farm near the Tradewater River offers an excellent opportunity for any outdoor enthusiast! Throughout this timber tract you will find varying topography, including rock bluffs, rolling timbered ridges and two cleared areas, ideal for food plots or a basecamp. The woods consist of both softwoods and hardwoods to provide a good food source while the cedar thickets offer shelter for

  

  Ryals Farless

  Farless Realty

  (270) 518-2323

  0 Donahue Rd, Princeton, KY 42445
• 

  

  /29

  $175,000

  • 3 Beds
  • 1.5 Baths
  • 1,539 Sq Ft

  307 Maple St, Princeton, KY 42445

  This one level, 3 bedroom, 1.5 bath home is just what you've been looking for! The interior offers hardwood flooring, open kitchen/dining/den, formal living room and washer/dryer hook-ups. Outside you'll find a low maintenance brick exterior, screened patio on the side of the home, large patio on the rear, detached garage and a partially fenced back yard! There is also a detached garage with

  

  Ryals Farless

  Farless Realty

  (270) 606-7906

  307 Maple St, Princeton, KY 42445
• 

  

  /55

  $941,250

  • Land
  • 251 Acres
  • $3,750 per Acre

  Littlefield Rd Unit LotWP001, Princeton, KY 42445

  All timber hunting tract with a proven history of big bucks! This property offers an outstanding layout for serious deer and turkey hunters, featuring a large timbered ridge system and an ideal mix of habitat types throughout. The rolling topography and diverse structure naturally create numerous funnels and pinch points that concentrate deer movement, making it highly effective for stand

  Justin Mason Whitetail Properties Real Estate

  Littlefield Rd Unit LotWP001, Princeton, KY 42445
• 

  

  /86

  $749,000

  • 6 Beds
  • 3.5 Baths

  141 Leech Hill Cemetery Rd, Fredonia, KY 42411

  This 10.62+/- acre property in Caldwell County, KY, features a beautiful home, multiple outbuildings, and a fully operational livestock setup. Built in 2014, the 4,251 S.F. home offers 6 bedrooms, 3.5 baths, and a spacious layout with an additional 2,834 S.F. unfinished basement. A 900 S.F. attached 2-car garage provides convenience, while the landscaped yard, shade trees, and garden area add to

  Mark Williams Whitetail Properties Real Estate

  141 Leech Hill Cemetery Rd, Fredonia, KY 42411
• 

  

  /86

  $975,000

  • 6 Beds
  • 3.5 Baths
  • 4,251 Sq Ft

  141 Leech Hill Cemetery Rd, Fredonia, KY 42411

  This exceptional property offers a spacious 6-bedroom, 3.5-bath home with 4,251 square feet of above-grade living space and an additional 2,834-square-foot unfinished basement. Built in 2014, the home features an attached 2-car garage (900 square feet), a large yard with mature shade trees, and a gravel driveway with ample parking. The property is fully equipped for livestock operations with

  Mark Williams Whitetail Properties Real Estate

  141 Leech Hill Cemetery Rd, Fredonia, KY 42411
• 

  

  /27

  $245,000

  • 3 Beds
  • 2 Baths
  • 1,328 Sq Ft

  106 Dogwood Ln, Princeton, KY 42445

  Location, Location, Location. This Home is located in the Country Club Subdivision, with a very short golf-cart ride to a great golf course, pool, tennis, pickleball, and much more. Home features 3 bedrooms, 2 full baths, split-level home with a gas fireplace in the living room, wonderful kitchen with stainless steel appliances, Master bedroom with Master bath, Unfinish basement area for storage

  Jesse Case RE/MAX Real Estate Services

  106 Dogwood Ln, Princeton, KY 42445
• 

  

  /25

  $284,500

  • 3 Beds
  • 2 Baths
  • 1,496 Sq Ft

  11774 Hopkinsville Rd, Princeton, KY 42445

  Remodeled brick home on 4 acres of land. Upgraded kitchen, with island and black stainless steel appliances. Breakfast nook. Large living room. Brand new bathroom with soaking tub and separate walk-in shower. Second bathroom with walk-in shower. Nice sized primary, large enough for a king bed and two additional bedrooms. There is also an unfinished basement with cellar. Outside, enjoy family time

  Lisa Boren Payne Real Estate Group

  11774 Hopkinsville Rd, Princeton, KY 42445
• 

  

  /11

  $299,000

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  20 Cravens Rd, Princeton, KY 42445

  New construction Home featuring 3 bedrooms and two full Baths. Large living room with high ceilings. Large master with large bath. Covered front porch and large deck. Attached 2 car garage

  Thomas Hughes Coldwell Banker Service 1st Realty

  20 Cravens Rd, Princeton, KY 42445
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  /62

  $349,900

  • 2 Beds
  • 1 Bath
  • 1,322 Sq Ft

  315 Amon Lisanby Spur Rd, Dawson Springs, KY 42408

  Discover the perfect blend of comfort and outdoor living in this stunning 2-bedroom, 1-bath barndominium in Dawson Springs, KY. Built in 2022, this 1,322-square-foot home sits on a picturesque 1-acre lot overlooking a tranquil lake. Enjoy breathtaking views from your very own outdoor recreational area, complete with an outdoor kitchen and bar—ideal for entertaining or relaxing by the water. A

  Josh Parish Bhg Realty

  315 Amon Lisanby Spur Rd, Dawson Springs, KY 42408
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  /33

  $176,000

  • 3 Beds
  • 2 Baths
  • 1,964 Sq Ft

  707 Vivian Dr, Princeton, KY 42445

  Check out this 3 bed 2 bath brick ranch home located in the Dixie Heights Subdivision of Princeton! Inside, this home features a versatile den or bonus room complete with a cozy gas log fireplace and walk-in closet perfect for an additional living space, office or guest area. The formal dining room offers a great spot for family meals and entertaining. The very large utility room is a standout

  Brandon Warfield Benchmark Realty

  707 Vivian Dr, Princeton, KY 42445
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  /30

  $239,900

  • 4 Beds
  • 2 Baths
  • 1,860 Sq Ft

  16475 Dawson Rd, Dawson Springs, KY 42408

  Are you looking for a spacious four-bedroom home with over four acres of land? This is your opportunity to own a beautifully updated property for under $250,000. This home features matching LVT flooring throughout and includes a fenced backyard, a deck, and even a chicken coop. It's conveniently located less than 10 miles from Princeton and just 3 miles from Dawson Springs.

  Kimberly Ann Clapp The Jeter Group

  16475 Dawson Rd, Dawson Springs, KY 42408
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  /33

  $220,000

  • 5 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  212 N Plum St, Princeton, KY 42445

  This is more than a house—it’s the space your life has been waiting for. With 5 bedrooms, 2.5 baths, and storage in every direction, there’s room for everyone and everything. A brand new roof and water heater mean you can move in with confidence. Host family dinners, work from home, throw birthday parties, or just enjoy a quiet evening in—the layout adapts to your every need. Natural light fills

  Lauren Hawkins Benchmark Realty

  212 N Plum St, Princeton, KY 42445
• 

  

  /11

  $189,000

  • 3 Beds
  • 2 Baths
  • 2,389 Sq Ft

  123 S Highland Ave, Princeton, KY 42445

  This 2300+ square ft brick home offers 3 bedroom 2 bath and an in-law suite equipped with kitchenet. This property has been a rental home for 20 plus years and is currently rented. The home features over half acre lot with 2 separate entrances. This home would make a great investment or wonderfully large home for a family.

  Sherry Thomas Keller Williams Experience Realty Eddyville Branch

  123 S Highland Ave, Princeton, KY 42445
• 

  

  /49

  $941,250

  000 Littlefield Rd Unit (Caldwell Co. KY 251, Princeton, KY 42445

  This all-timber hunting property offers an outstanding layout for serious deer and turkey hunters, featuring a large timbered ridge system and an ideal mix of habitat types throughout. A 2019 timber cruise valued the standing timber at $312,958.57, adding notable long-term investment value. A landing area near the access point provides a great location for a cabin, hunting camp, or equipment

  Justin Mason Whitetail Properties Real Estate LLC

  000 Littlefield Rd Unit (Caldwell Co. KY 251, Princeton, KY 42445
• 

  

  /20

  $89,000

  • 2 Beds
  • 1 Bath
  • 824 Sq Ft

  530 N Donnivan St, Princeton, KY 42445

  Welcome to this cozy 2 bedroom 1 bath home located in the heart of Princeton! Whether you're looking for a primary residence or an addition to your investment portfolio check this one out! Inside, you’ll find two bedrooms a full bath and a flexible third room that could easily serve as a 3rd bedroom, office or bonus space to fit your lifestyle needs. This home offers a comfortable layout perfect

  Brandon Warfield Benchmark Realty

  530 N Donnivan St, Princeton, KY 42445
• 

  

  /13

  $160,000

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft

  9025 Ky-902 E, Fredonia, KY 42411

  If you’re looking for a property to start homesteading or even just somewhere to relax on a covered porch—this is the one! With a little over a spacious acre you’ve got plenty of room to start harvesting your own garden or tending to your chickens. Recently built chicken coop conveys! Move in ready home with a newer roof covering. (2023) Hot tub will be removed off property unless negotiated

  Harley Parr Benchmark Realty

  9025 Ky-902 E, Fredonia, KY 42411
• 

  

  /12

  $185,000

  • Land
  • 7.65 Acres
  • $24,183 per Acre

  000 N Jefferson St, Princeton, KY 42445

  7.65 +/- surveyed acres loaded with commercial and/or residential potential! Just off of I-69 & 383 feet of North Jefferson st road frontage for great commercial potential & 293 feet of Skyline Dr road frontage for your residential potential. If it would better suit your needs, this property can be divided and purchased in sections if desired with approval from planning and zoning. This property

  Austin Thomas Keller Williams Experience Realty Paducah Branch

  000 N Jefferson St, Princeton, KY 42445
• 

  

  /28

  $169,000

  • 3 Beds
  • 1 Bath
  • 1,165 Sq Ft

  307 W Wyatt St, Fredonia, KY 42411

  Small town living at it's finest! Perfect Ranch style home located in Fredonia, Ky. Minutes from Marion, Princeton, Eddyville and Lake Barkley. Whether you are retiring or need space for your family this is it. Approximately 1200 sq ft., 2 car attached garage and a 50x50 three car detached garage or workshop, with a wood burner stove, on it's own water and electric meter. Backyard backs up to a

  Angie Cornish Keller Williams Experience Realty Eddyville Branch

  307 W Wyatt St, Fredonia, KY 42411
• 

  

  /8

  $10,000

  • Land
  • 0.5 Acre
  • $20,000 per Acre

  1027 N Jefferson St, Princeton, KY 42445

  This .5 acre vacant lot in Princeton, Kentucky is the perfect opportunity for a new home site.

  Rhett Hughes WTC Realty LLC

  1027 N Jefferson St, Princeton, KY 42445
• 

  

  /23

  $172,500

  • 2 Beds
  • 2 Baths
  • 1,190 Sq Ft

  415 E Green St, Princeton, KY 42445

  Welcome to this well maintained 2 bed 2 bath home situated on a spacious lot in the city limits of Princeton! Inside, you’ll find gorgeous hardwood floors throughout and a cozy living room making for the perfect place to relax. The kitchen offers plenty of cabinetry and workspace for all your cooking needs. The newly completed ensuite bathroom (2025) adds a touch of modern comfort to the primary

  Brandon Warfield Benchmark Realty

  415 E Green St, Princeton, KY 42445
• 

  

  /22

  $50,000

  • 3 Beds
  • 1 Bath
  • 1,532 Sq Ft

  217 Baldwin Ave, Princeton, KY 42445

  Great investment property located at 217 Baldwin Ave. Princeton, KY42445. Home offers a total of three to four bedrooms and one bath with approximately 1532 ft.2 of living space, sitting on approximately 1/2 acre. Close to shopping and restaurants. Home would make a great investment property or with some TLC, be made into a great first home. Home is being SOLD AS IS.

  Tonya Beadnell Wright Choice of Kentucky Realty & Auction

  217 Baldwin Ave, Princeton, KY 42445
• 

  

  /19

  $99,900

  • 3 Beds
  • 1 Bath
  • 925 Sq Ft

  402 E Locust St, Princeton, KY 42445

  Great opportunity to make this home your own! This property features new flooring, fresh paint throughout, a brand-new kitchen sink, and an updated bathroom. The unfinished basement offers additional storage. The home does not currently have an HVAC system and is being sold AS-IS. Cash or conventional financing only—this one will not qualify for FHA, USDA, or VA loans. Perfect for investors or

  Darren Ramey Farless Realty

  402 E Locust St, Princeton, KY 42445
• 

  

  /9

  $40,000

  • Land
  • 1.7 Acres
  • $23,529 per Acre

  240 Jeff Watson Rd, Princeton, KY 42445

  Discover the perfect spot to build your dream home with this beautiful lot located within the city limits of Princeton. Tucked away off the road, this property is surrounded by trees creating a private setting with a country feel. A creek runs along the front of the property adding to its natural appeal. With electric, water and sewer already available this lot is ready for your vision. Enjoy the

  Brandon Warfield Benchmark Realty

  240 Jeff Watson Rd, Princeton, KY 42445
• 

  

  /25

  $88,000

  • 3 Beds
  • 1 Bath
  • 1,206 Sq Ft

  934 Farmersville Rd, Princeton, KY 42445

  This 3-bedroom, 1-bath home with an attached 2-car garage is being sold AS-IS. It’s a fixer-upper with potential. Major bonus: brand new HVAC in 2023. Great opportunity to flip, rent, or make it your own with some sweat equity!

  Darren Ramey Farless Realty

  934 Farmersville Rd, Princeton, KY 42445
• 

  

  /14

  $99,900

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft

  17551 Dawson Rd, Dawson Springs, KY 42408

  A perfect starter home, retirement home or hunting cabin. All of this sitting on approx. four acres in the county with no city taxes. These homes do not come on the market very often and small acreage sites are in high demand. The majority of the acreage is wooded and private and behind the home. The basement has a laundry area and lots of storage room. There is no water heater or HVAC.

  Tim Beck Property Investment Solutions

  17551 Dawson Rd, Dawson Springs, KY 42408
• 

  

  /50

  $749,000

  • 6 Beds
  • 3.5 Baths

  141 Leech Hill Cemetery Rd Unit (Caldwell Co. KY 10., Fredonia, KY 42411

  This 10.62+/- acre property in Caldwell County features a beautiful home, multiple outbuildings, and a fully operational livestock setup. Built in 2014, the 4,251 S.F. home offers 6 bedrooms, 3.5 baths, and a spacious layout with an additional 2,834 S.F. unfinished basement. A 900 S.F. attached 2-car garage provides convenience, while the landscaped yard, shade trees, and garden area add to the

  Mark Williams Whitetail Properties Real Estate LLC

  141 Leech Hill Cemetery Rd Unit (Caldwell Co. KY 10., Fredonia, KY 42411
• 

  

  /48

  $235,000

  • 3 Beds
  • 2 Baths
  • 1,786 Sq Ft

  912 W Main St, Princeton, KY 42445

  Beautifully updated 3 bedroom, 2 bathroom brick home with an unfinished basement that could easily be finished for added living space. Recent updates include all new luxury vinyl plank flooring, fresh paint, new kitchen appliances, sink, cabinet hardware, bathroom vanities, and toilets. HVAC and roof are just 6 years old, and the water heater is 4 years old. Move-in ready and situated on a large

  Darren Ramey Farless Realty

  912 W Main St, Princeton, KY 42445
• 

  

  /24

  $154,000

  • 3 Beds
  • 2 Baths
  • 930 Sq Ft

  408 N Hawthorne St, Princeton, KY 42445

  This charming 3 bedroom 2 bathroom home is full of updates and ready for its new owners! Inside, you’ll find two bedrooms and a full bath on the main level along with a spacious living area featuring beautiful recessed lighting and a cozy gas log fireplace in the living room. Upstairs, you will appreciate the large private bedroom suite with its own bathroom and oversized closet perfect for a

  Brandon Warfield Benchmark Realty

  408 N Hawthorne St, Princeton, KY 42445
• 

  

  /50

  $245,000

  • 3 Beds
  • 2 Baths
  • 1,925 Sq Ft

  920 W Main St, Princeton, KY 42445

  Step back in time with this charming 1912 home offering 3 bedrooms and 2 bathrooms. Filled with character, it features a large foyer, formal living and dining rooms, and a cozy den with a gas fireplace just off the kitchen. Two bedrooms are located downstairs with a third upstairs. Sitting on a spacious lot in town, this property also includes two detached garages—plenty of space inside and out!

  Darren Ramey Farless Realty

  920 W Main St, Princeton, KY 42445
• 

  

  /26

  $139,000

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  309 N Eagle St, Princeton, KY 42445

  Welcome to this 3 bedroom 1 bathroom home offering both character and comfort. Inside, you’ll find tall ceilings that create an open and airy feel throughout along with a cozy gas log fireplace in the living room perfect for relaxing evenings at home. The spacious eat-in kitchen pairs wonderfully with the formal dining room making it easy to host family and friends. The beautiful oversized window

  Brandon Warfield Benchmark Realty

  309 N Eagle St, Princeton, KY 42445
• 

  

  /17

  $149,900

  • 4 Beds
  • 3 Baths
  • 2,879 Sq Ft

  501 W Main St, Princeton, KY 42445

  Spacious home with recent updates. This property features a durable metal roof, a welcoming front porch, and newer carpeting. The home is warmed by radiator heat and includes a new front door. An unfinished basement and attic provide ample storage or potential for a workshop. The garage offers a great opportunity for customization. **PLEASE call to set up showings which are by appointment only**

  Derek Eisenberg Continental Real Estate Group, Inc.

  501 W Main St, Princeton, KY 42445
• 

  

  /18

  $150,000

  • 2 Beds
  • 1 Bath
  • 1,729 Sq Ft

  10671 Ky-902 E, Fredonia, KY 42411

  This home offers 2 large bedroom, 1 bath, kitchen, dining room and a large family room with fireplace. a 2 car detached garage and a 24x34 shop building and a small smokehouse. This home is on county water but also offers well water to hydrant, sitting on 1 acre in a beautiful country setting. This home needs TLC, but if you can vision updates you should check it out. This home is an estate and

  Sherry Thomas Keller Williams Experience Realty Eddyville Branch

  10671 Ky-902 E, Fredonia, KY 42411
• 

  

  /34

  $93,000

  • 2 Beds
  • 2 Baths
  • 1,678 Sq Ft

  605 N Jefferson St, Princeton, KY 42445

  Looking for a nostalgic home in a small town? Early 1900 built, this home has high ceilings and vintage moldings, with updated windows, wood floors under the carpet. Fireplaces capped off in 2011 when new roof was installed. Driveway owned by this house, right of way easement in deed for neighbor to have access (607 N Jeff.), Bathrooms- Tub and Shower were replaced July 2025. Great Investment

  Eunice Stone Lakeland Realty

  605 N Jefferson St, Princeton, KY 42445
• 

  

  /38

  $240,000

  • Land
  • 39.98 Acres
  • $6,003 per Acre

  000 Edwards Rd, Princeton, KY 42445

  Whether you're looking for a place to get away, hunt, or build your dream house this could be that farm. 39.98 acres sitting on the end of a dead end road just 7 miles from Princeton and 5 miles from I-69. Water and electric are available at the road with some mature timber, a food plot, and shooting house already in place. With roughly 15 acres of open acres that could be planted or grazed, the

  Reese Johnson Keller Williams Experience Realty Paducah Branch

  000 Edwards Rd, Princeton, KY 42445
• 

  

  /29

  $400,000

  • 3 Beds
  • 2 Baths
  • 2,340 Sq Ft

  418 Lewistown Church Rd, Princeton, KY 42445

  Welcome home to 418 Lewistown Church Rd! Your own slice of country living with just over 20 acres of cleared & wooded land. A fully stocked pond for summer fishing, detached garage that makes a great workshop and a barn that has so much potential. You'll find two oversized living spaces inside, large laundry room and walk in closets. All within close proximity to convenient amenities. Now's the

  Dustin Gilbert eXp REALTY

  418 Lewistown Church Rd, Princeton, KY 42445

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