Saint Matthews, KY Homes for Sale under $500,000

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  /7

  $335,000

  $40K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,730 Sq Ft

  4022 Gilman Ave, Louisville, KY 40207

  Fantastic opportunity in the heart of sought-after St. Matthews! This solid brick ranch sits in one of Louisville's most desirable 40207 neighborhoods, just a short walk to top-rated schools, shopping, dining, parks, and the busline. Loved for years, the home is ready for your updates and personal touch — bring your vision and add instant equity in an area where charming, updated homes command a

  

  Yalonda Buckner

  Buckner Real Estate Services, LLC

  4022 Gilman Ave, Louisville, KY 40207
• Explore Saint Matthews

• 

  

  

  /66

  $375,000

  $20K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,318 Sq Ft

  209 Fairfax Ave Unit 1, Louisville, KY 40207

  UPDATED PRICE! This two-story condominium is the original house on this property and offers the ideal blend of low-maintenance living and the privacy of a single-family home. Perfect for a multi-generational household and perfectly positioned in the heart of St. Matthews—just steps from City Hall, the St. Matthews Police Station and the public library—this spacious 4-bedroom, 3 full bath

  

  Carl Horton

  Semonin Realtors

  209 Fairfax Ave Unit 1, Louisville, KY 40207
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  /18

  $325,000

  • 4 Beds
  • 2 Baths
  • 1,922 Sq Ft

  309 S Hubbards Ln, Louisville, KY 40207

  Rare opportunity to lock in a classic 1946 Colonial in the heart of St. Matthews and build instant equity! Located in desirable Parkside, this 4-bedroom, 2-full-bath home offers 1,682 sq ft above grade plus a partially finished basement yielding nearly 1,900 total finished sq ft. Character details include original hardwood floors, a cozy fireplace, an attached 1-car garage, and a fenced yard. The

  

  Yalonda Buckner

  Buckner Real Estate Services, LLC

  309 S Hubbards Ln, Louisville, KY 40207
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  /13

  $380,000

  • 3 Beds
  • 2.5 Baths
  • 4,275 Sq Ft

  5817 Prince William St, Louisville, KY 40207

  Rare size in the heart of St. Matthews — over 4,000 finished square feet on a quarter acre in Jamestown Manor, nearly double most homes in the neighborhood. A two-story foyer with a curved staircase opens to a formal living room and a large family room with fireplace and built-ins. Granite kitchen with room for a crowd, formal dining room, and a four-season Florida room overlooking the deck and

  

  Yalonda Buckner

  Buckner Real Estate Services, LLC

  5817 Prince William St, Louisville, KY 40207
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  /53

  $445,000

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,695 Sq Ft

  4600 Beaver Rd, Louisville, KY 40207

  WHAT A GREAT OPPORTUNITY! A significant price reduction PLUS a $12,000 ALLOWANCE makes this Beechwood Village home one to see! Offering over 2,600 finished sq ft, 4 bedrooms and 2 full baths, this spacious home sits on a large corner lot and is filled with character and possibilities. Hardwood floors, granite countertops and generously sized rooms create a warm, inviting feel. The second level

  

  Rita Walker

  Eline Realty Company

  4600 Beaver Rd, Louisville, KY 40207
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  /48

  $284,900

  $15K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,688 Sq Ft

  3619 Brownsboro Rd Unit 3619, Louisville, KY 40207

  Spacious, low-maintenance living in an unbeatable Louisville location! Ideally situated along the sought-after Brownsboro Road corridor, this beautifully maintained townhome offers an impressive combination of space, comfort, and convenience. Hardwood flooring extends through much of the main level, where you'll find an inviting living room filled with natural light, a spacious dining area, and

  

  Jeremy Byers

  RE/MAX Premier Properties

  3619 Brownsboro Rd Unit 3619, Louisville, KY 40207
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  /68

  $445,000

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft

  208 Oxford Place, Louisville, KY 40207

  Welcome home to the heart of Saint Matthews and this fantastic three bedroom, two bath home! Within walking distance of Seneca Park and a multitude of shops and restaurants, here is your private oasis. You're greeted with a beautiful blend of classic elements and modern amenities in the cozy living room, large dining (or activity) room, wood floors, and kitchen with granite countertops. Enjoy a

  Courtney Dietrich Enrich Realty LLC

  208 Oxford Place, Louisville, KY 40207
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  /45

  $365,000

  $45K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,620 Sq Ft

  307 Fairmeade Rd, Louisville, KY 40207

  Nestled in the heart of the highly desirable St. Matthews area! This charming home offers incredible potential for buyers looking to add their personal touch. The home has great bones and ready for a fresh vision to make it shine. A functional layout with 3 bedrooms, 2 full baths, a corner fireplace separates the living room and dining room with a laundry room all on the first floor. The basement

  Karla Wright G. Starks Realty Co.

  307 Fairmeade Rd, Louisville, KY 40207
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  /26

  $279,000

  • 2 Beds
  • 2 Baths
  • 1,540 Sq Ft

  5800 Coach Gate Wynde Unit 295, Louisville, KY 40207

  Beautiful unit in secured building with garage parking! Spacious living room with newer patio doors onto covered patio and adjoining dining area with built-in bookcases. Cozy den space with wet bar area as well as more built-in bookcases. The kitchen is has good counter space, a pantry cabinet as well as a built-in corner hutch. The primary bedroom is very good sized and has an adjoining bath

  Michael Jones Cornerstone Group REALTORS

  5800 Coach Gate Wynde Unit 295, Louisville, KY 40207
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  /62

  $399,000

  • 2 Beds
  • 3 Baths
  • 2,817 Sq Ft

  265 Leland Ct Unit 3, Louisville, KY 40207

  Welcome to this updated first-floor condo in the heart of St. Matthews, offering the perfect mix of comfort, space, and convenience. Beautifully remodeled throughout with high-end finishes, this spacious unit features refinished hardwood floors, three full bathrooms, and a layout that blends functionality with style. Step inside to a bright and inviting living area with plenty of room for dining

  Elizabeth Monarch EXP Realty LLC

  265 Leland Ct Unit 3, Louisville, KY 40207
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  /41

  $399,900

  • 3 Beds
  • 2 Baths
  • 2,349 Sq Ft

  407 Macon Ave, Louisville, KY 40207

  Welcome to this charming 3 bedroom, 2 bathroom home in the heart of St. Matthews. From the refreshed landscaping to the inviting front porch, this home makes a great first impression and offers the perfect spot to sit back, relax, and enjoy your favorite drink. Inside, the first floor has an easy, comfortable flow with an updated kitchen that opens to the family room, making it a great setup for

  Michael Weisberg BERKSHIRE HATHAWAY HomeServices, Parks & Weisberg Realtors

  407 Macon Ave, Louisville, KY 40207
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  /29

  $272,000

  • 2 Beds
  • 2 Baths
  • 1,540 Sq Ft

  5800 Coach Gate Wynde Unit 273, Louisville, KY 40207

  Great condo in beautifully maintained Coach House in super convenient location in building--one of the closest units to the elevator AND to parking garage spots. This main floor unit has a very large living/dining room, nice sized eat-in kitchen ( all with easy care vinyl plank flooring), a very large primary suite with multiple closets, a full bath with double vanity as well as a walk-in closet.

  Michael Jones Cornerstone Group REALTORS

  5800 Coach Gate Wynde Unit 273, Louisville, KY 40207
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  /35

  $395,000

  • 3 Beds
  • 2 Baths
  • 1,954 Sq Ft

  221 Ring Rd, Louisville, KY 40207

  Conveniently situated near an abundance of shops, restaurants, & easy access to the Watterson Expressway, this charming home offers both comfort & convenience. The living room & dining room feature beautiful hardwood floors that continue throughout all three bedrooms. The spacious kitchen provides plenty of cabinet & counter space, plus a bonus mudroom offering excellent add'l storage &

  Samuel Osbourne Family Realty LLC

  221 Ring Rd, Louisville, KY 40207
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  /48

  $389,900

  • 3 Beds
  • 1.5 Baths
  • 1,692 Sq Ft

  3717 Hillsboro Rd, Louisville, KY 40207

  Welcome to this beautifully updated 3-bedroom, 2-bath home in the heart of highly desirable St. Matthews! Ideally located just minutes from restaurants, shopping, hospitals, and everyday conveniences, this home offers the perfect combination of charm, comfort, and location. Inside, you'll find refinished hardwood floors, fresh paint throughout, an updated kitchen featuring granite countertops, a

  Jeffrey Logsdon DREAM J P Pirtle REALTORS

  3717 Hillsboro Rd, Louisville, KY 40207
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  /51

  $394,500

  $31K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,579 Sq Ft

  3718 Hillsboro Rd, Louisville, KY 40207

  Nestled on one of St. Matthews' most charming streets, complete with a picturesque park in the center, this delightful 3-bedroom, 2-bath home offers the perfect blend of character, comfort, and opportunity. From the moment you arrive, you'll appreciate the inviting curb appeal and welcoming neighborhood. Inside, you'll find a warm and spacious layout, along with a fully finished basement that

  Emily Blanford Homepage Realty

  3718 Hillsboro Rd, Louisville, KY 40207
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  /50

  $399,000

  • 3 Beds
  • 1.5 Baths
  • 1,640 Sq Ft

  243 Fairfax Ave, Louisville, KY 40207

  Welcome home to this charming stone-front Cape Cod offering 3 bedrooms, 1.5 baths, a detached one-car garage, a partially finished basement, and an incredible backyard retreat in the heart of St. Matthews. Step inside to a spacious living room featuring beautiful original hardwood flooring that continues throughout much of the main level. The living room flows seamlessly into the dining room and

  Gary Aronov Real Estate Go To

  243 Fairfax Ave, Louisville, KY 40207
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  /61

  $469,900

  • 3 Beds
  • 3 Baths
  • 2,710 Sq Ft

  107 Cornell Place, Louisville, KY 40207

  Welcome to 107 Cornell Place, where timeless architecture meets modern versatility in the heart of St. Matthews. Originally built in 1885 and thoughtfully renovated, with additional recent improvements enhancing its everyday functionality and long-term value, this one-of-a-kind residence offers the rare opportunity to enjoy historic charm with the flexibility today's lifestyle demands. Rich in

  Elizabeth Oldham Trueblood Real Estate

  107 Cornell Place, Louisville, KY 40207
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  /38

  $409,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,490 Sq Ft

  3811 Grandview Ave, Louisville, KY 40207

  Welcome to 3811 Grandview Ave, a charming cape cod nestled in the highly coveted St. Matthews area of Louisville! This inviting 3-bedroom, 2-bathroom home offers an ideal setting for those seeking comfort, convenience, and community. You'll love being just minutes away from scenic parks, vibrant downtown Louisville, popular restaurants and bars, cozy coffee shops, and so much more. Step inside to

  Jamie Gardner Real Broker, LLC

  3811 Grandview Ave, Louisville, KY 40207
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  /52

  $369,900

  $5K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 2,936 Sq Ft

  323 N Hubbards Ln, Louisville, KY 40207

  Welcome home to this charming classic St. Matthews gem, where timeless character meets modern comfort. This beautifully maintained 3-bedroom, 11⁄2-bath home is filled with distinctive details, including gorgeous hardwood floors, built-in cabinetry, and a charming black-and-white tile bathroom that adds vintage appeal. Fresh new carpet on the second floor and throughout the spacious finished

  Emily Blanford Homepage Realty

  323 N Hubbards Ln, Louisville, KY 40207
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  /24

  $335,000

  $35K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,410 Sq Ft

  316 Monohan Dr, Louisville, KY 40207

  Great location in St. Matthews! Cozy living room with fireplace, large eat in kitchen with new counter top and appliances, open to dining room, 2 bedrooms and full bathroom complete 1st floor with hardwood floors and fresh paint. 2nd floor has 2 bedrooms and could easily be converted into a primary bedroom and bathroom. Room to expand living area in unfinished basement. 1 car garage and fenced in

  Kenneth Kaiser simpler.realestate

  316 Monohan Dr, Louisville, KY 40207
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  /34

  $499,900

  $100K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 4,300 Sq Ft

  2406 Phoenix Hill Dr, Louisville, KY 40207

  Nestled in the heart of prestigious Indian Hills, this all-brick home offers exceptional space. All bedrooms are thoughtfully positioned on the second floor, creating a classic and functional layout. A walkout basement adds versatility for entertaining or extended living, while the private backyard showcases an inviting in-ground pool—ideal for summer enjoyment. Surrounded by mature trees and

  Karen Fox simpler.realestate

  2406 Phoenix Hill Dr, Louisville, KY 40207
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  /40

  $200,000

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft

  211 Fairfax Ave Unit 6, Louisville, KY 40207

  Welcome to 211 Fairfax Avenue, Unit 6 a move-in-ready corner-unit townhouse in the heart of highly desirable St. Matthews. Priced at $200,000, this spacious two-story condo offers 2 bedrooms, 1.5 bathrooms, an open living room, and a second-floor laundry. Updated flooring, carpet, and fresh paint create a clean, comfortable interior, while the private fenced patio provides the perfect space for

  Max Hargis DREAM J P Pirtle REALTORS

  211 Fairfax Ave Unit 6, Louisville, KY 40207
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  /29

  $350,000

  • 4 Beds
  • 1 Bath
  • 1,405 Sq Ft

  3706 Grandview Ave, Louisville, KY 40207

  Check out this charming St. Matthews bungalow perfectly located just minutes from shopping, restaurants, coffee shops, and beautiful Seneca Park! This inviting 4-bedroom, 1-bath home blends classic character with thoughtful updates, starting with a welcoming front porch — the perfect spot to relax and enjoy the neighborhood. Inside, you'll find original hardwood floors, a cozy brick fireplace,

  Zach Wedding Six Degrees Real Estate, LLC

  3706 Grandview Ave, Louisville, KY 40207
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  /35

  $410,000

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,548 Sq Ft

  422 Fairlawn Rd, Louisville, KY 40207

  This St. Matthews home is the kind of place that just feels easy to live in. It has plenty of character and charm, a friendly neighborhood, and a location close to Seneca Park, schools, shopping, and dining. Inside, you'll find beautiful hardwood floors, a cozy fireplace, lots of natural light, and a spacious primary suite upstairs. And with fall right around the corner, you'll have the perfect

  Melanie Jones Keller Williams Collective

  422 Fairlawn Rd, Louisville, KY 40207
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  /28

  $455,000

  $14K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 2,101 Sq Ft

  419 Wendover Ave, Louisville, KY 40207

  Nestled beneath a canopy of mature trees in the heart of St. Matthews, this beautifully updated stone cottage offers over 2,100 square feet of finished living space, blending timeless charm with modern amenities. Featuring 2 bedrooms, 2 full baths, gleaming hardwood floors, arched doorways, and a chef's kitchen with a Wolf gas cooktop, GE stainless steel appliances, breakfast bar, and hidden

  Peggy Ann Fairleigh Elite Realty of Kentucky

  419 Wendover Ave, Louisville, KY 40207
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  /41

  $399,500

  $16K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  4209 Alton Rd, Louisville, KY 40207

  Lovely 3 Bedroom 2 Bath brick Cape Cod in sought after St Matthews. This beautifully maintained residence features hardwood flooring, gas fireplace and LOTS of closet space (rare in St Matthews). Kitchen remodeled in 2022 features custom all-wood cabinets, quartz countertops and stainless steel appliances. Enjoy customized comfort and efficiency with a dual-zone HVAC system (2021 and 2023). A

  Shaun Wallace 1 Percent Lists Purple Door

  4209 Alton Rd, Louisville, KY 40207
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  /29

  $419,900

  $15K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,700 Sq Ft

  302 Iola Rd, Louisville, KY 40207

  New Price! Conveniently located St Mathews home. 3 bedrooms, 2.5 bathrooms, 1,700 square feet. Updated kitchen and bathrooms, open floorplan! Solid surface kitchen countertops. Hardwood floors throughout. Upstairs bedrooms have separate mini-split HVAC units. Large deck off kitchen and primary suite, overlooks a fence rear yard. 1 car detached garage with concrete driveway. Unfinished basement.

  Jeff Perellis BERKSHIRE HATHAWAY HomeServices, Parks & Weisberg Realtors

  302 Iola Rd, Louisville, KY 40207
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  /31

  $450,000

  • 3 Beds
  • 2 Baths
  • 2,300 Sq Ft

  1800 Rudy Ln, Louisville, KY 40207

  Welcome to 1800 Rudy Lane with the main entry conveniently located on the side of the home facing Rudy Lane. This 3 bedroom, 2 bathroom ranch offers a functional layout, generous living space, and an unbeatable location. The front foyer welcomes you and opens to a formal dining room on the right, with plenty of room for a large dining table. The perfect place for large family meals! A pocket door

  Katie Esterle White Picket Real Estate

  1800 Rudy Ln, Louisville, KY 40207
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  /34

  $397,500

  $2K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,011 Sq Ft

  3806 Napanee Rd, Louisville, KY 40207

  An exceptional opportunity awaits to personalize this charming Cape Cod nestled in the heart of Brownsboro Village. This inviting 3-bedroom, 2-bath home blends character and potential, featuring beautiful hardwood floors, an expansive dining room perfect for hosting, and a bright galley-style kitchen with abundant cabinetry and generous counter space. The vaulted family room is a true highlight,

  Allison Bartholomew Weichert Realtors-ABG

  3806 Napanee Rd, Louisville, KY 40207
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  /39

  $400,000

  $25K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,049 Sq Ft

  5939 Ashwood Bluff Dr, Louisville, KY 40207

  **Great Price Improvement on 5939 Ashwood Bluff Dr in desirable east end area.*** Enjoy effortless, maintenance-free living in this beautifully designed patio home, perfectly located off Brownsboro Road. Tucked into a highly desirable area with quick access to major freeways, this home offers both convenience and comfort. This home has had only one owner and cared for throughout the years.Inside,

  Dedre Morse simpler.realestate

  5939 Ashwood Bluff Dr, Louisville, KY 40207
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  /18

  $375,000

  • Land
  • 23,522 Sq Ft
  • $694,444 per Acre

  2301 Clovelly Springs Ct, Louisville, KY 40207

  LOT 10 / Experience the beauty and tranquility of Poplar Hill Bluff, an intimate community where nature's splendor meets thoughtful stewardship, and every detail is designed to enrich your living experience. Perched on a hill, surrounded by mature hardwoods and native vegetation, ten custom-built homesites designed by Doug Schmitt await. Each home features harmonious architecture, timeless curb

  Mac Barlow Kentucky Select Properties

  2301 Clovelly Springs Ct, Louisville, KY 40207
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  /17

  $380,000

  • Land
  • 23,086 Sq Ft
  • $716,981 per Acre

  Lot 3 Poplar Hill Bluff, Louisville, KY 40207

  LOT 3 / Experience the beauty and tranquility of Poplar Hill Bluff, an intimate community where nature's splendor meets thoughtful stewardship, and every detail is designed to enrich your living experience. Perched on a hill, surrounded by mature hardwoods and native vegetation, ten custom-built homesites designed by Doug Schmitt await. Each home features harmonious architecture, timeless curb

  Mac Barlow Kentucky Select Properties

  Lot 3 Poplar Hill Bluff, Louisville, KY 40207
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  /51

  $310,000

  $20K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,668 Sq Ft

  401 Country Ln Unit A, Louisville, KY 40207

  *** Owner financing available *** Location, Location, Location! Units in the Townhomes of Country Lane rarely come for sale. If you want maintenance free living in 40207, come see this updated condo on desirable Country Lane, just off Brownsboro Road near Crescent Hill, Indian Hills and St. Matthews. This 2 bedroom, 2.5 bath property has a 1-car attached garage, partially finished basement, and

  Michael O'brien United Real Estate Louisville

  401 Country Ln Unit A, Louisville, KY 40207
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  /36

  $409,950

  $65K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,978 Sq Ft

  5943 Ashwood Bluff Dr, Louisville, KY 40207

  Charming 3-bedroom, 2.5-bath patio home in a highly convenient Brownsboro Road location! This well-maintained home features an updated eat-in kitchen with modern finishes, that is perfect for everyday living. The spacious first-floor primary suite offers comfort and privacy, while ample closet space and large adjoining updated full bath. Enjoy the spacious open great room and dining area with

  Betty Radford simpler.realestate

  5943 Ashwood Bluff Dr, Louisville, KY 40207
• 

  

  /32

  $345,000

  • 3 Beds
  • 1 Bath
  • 1,354 Sq Ft

  313 Iola Rd, Louisville, KY 40207

  Welcome home to 313 Iola Rd! Step inside from the covered front porch to discover original hardwood floors that flow throughout the home. The front living room welcomes you in and is anchored by a cozy fireplace, creating a warm and welcoming gathering space. Just beyond, the dining room seamlessly connects to the updated kitchen and offers access to the charming sunroom, the perfect spot to

  Kyle Elmore White Picket Real Estate

  313 Iola Rd, Louisville, KY 40207
• 

  

  /24

  $389,000

  • 3 Beds
  • 2.5 Baths
  • 1,800 Sq Ft

  609 Wallace Ave Unit 3, Louisville, KY 40207

  Welcome to 609 Wallace Avenue, a charming Cape Cod on a quiet street in the heart of St. Matthews! This 3 bedroom, 2 1/2 bath home boasts a new roof and recently updated water heater and cedar fencing. The current owners have also replaced the windows and all kitchen appliances. Beautiful hardwood floors and a bright sunroom with original louvered windows add to the historic 1940s charm.

  Julie Pogue Julie Pogue Properties

  609 Wallace Ave Unit 3, Louisville, KY 40207
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  /43

  $439,000

  $11K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,069 Sq Ft

  4214 Churchill Rd, Louisville, KY 40207

  PRICED $11,000 BELOW APPRAISAL * Quick possession available on this charming, turnkey Cape Cod in one of Louisville's most desirable areas, just minutes from shopping, dining, parks, and easy access to interstates. A front porch welcomes you into a light-filled living room featuring hardwood floors, an inviting fireplace, arched doorways, and abundant natural light. The updated eat-in kitchen

  Joseph Simms simpler.realestate

  4214 Churchill Rd, Louisville, KY 40207
• 

  

  /34

  $340,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft

  357 Ridgeway Ave, Louisville, KY 40207

  For those who see beauty in the unexpected and inspiration in the extraordinary, this truly one-of-a-kind property offers a chance to own a home unlike anything else in Louisville. Part residence, part work of art, and part architectural treasure hunt, this remarkable property was thoughtfully created around salvaged pieces from some of the city's most beloved historic landmarks. Built in 1984

  Allison Bartholomew Weichert Realtors-ABG

  357 Ridgeway Ave, Louisville, KY 40207
• 

  

  /18

  $495,000

  • Land
  • 19,602 Sq Ft
  • $1,100,000 per Acre

  2305 Clovelly Springs Ct, Indian Hills, KY 40207

  LOT 12 / Experience the beauty and tranquility of Poplar Hill Bluff, an intimate community where nature's splendor meets thoughtful stewardship, and every detail is designed to enrich your living experience. Perched on a hill, surrounded by mature hardwoods and native vegetation, ten custom-built homesites designed by Doug Schmitt await. Each home features harmonious architecture, timeless curb

  Mac Barlow Kentucky Select Properties

  2305 Clovelly Springs Ct, Indian Hills, KY 40207

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