Crestwood, KY Homes for Sale with Acreage

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  /49

  $1,074,900

  $5K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,540 Sq Ft

  5607 Farmhouse Lot 19 Dr, Crestwood, KY 40014

  Welcome home! This custom built home features an open floor plan with a vaulted ceiling in the great room, 2 fireplaces, and a cozy private retreat. Located in Farmhouse Estate, it is one of the last opportunities to have new construction in Centerfield's most desirable neighborhood! Custom built home features many amazing finishes and unique items...The''Keeping Room'' is easily accessible from

  

  Walt Schumm

  RE/MAX Real Estate Champions

  5607 Farmhouse Lot 19 Dr, Crestwood, KY 40014
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  /2

  $99,000

  • Land
  • 1 Acre
  • $99,000 per Acre

  7000 Middlebrook Dr Unit Lot 1, Crestwood, KY 40014

  Discover the freedom and flexibility of country living on this exceptional lot in a community where outbuildings and barndominiums are fully approved. With horses permitted on parcels over 4 acres, this property is ideal for anyone seeking space, privacy, and the ability to create a personalized homestead. Enjoy wide open acreage, peaceful surroundings, and the opportunity to design a lifestyle

  

  Walt Schumm

  RE/MAX Real Estate Champions

  7000 Middlebrook Dr Unit Lot 1, Crestwood, KY 40014
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  /46

  $798,900

  $51K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,421 Sq Ft

  2003 Wooded Oak Ln, Crestwood, KY 40014

  Set on a secluded 1.59 acre wooded estate in Grand Oaks, this refined residence offers a rare blend of privacy, elegance, and timeless architectural presence. Surrounded by mature trees and natural landscape, the home feels like a serene retreat moments from Crestwood. Inside, soft natural light and elevated finishes create an atmosphere of quiet luxury. The great room's fireplace adds

  

  Walt Schumm

  RE/MAX Real Estate Champions

  2003 Wooded Oak Ln, Crestwood, KY 40014
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  /2

  $175,000

  • Land
  • 1.8 Acres
  • $97,222 per Acre

  7008 Middlebrook Dr Unit Lot 2, Crestwood, KY 40014

  A rare opportunity to craft a private luxury estate on one of the most flexible and desirable parcels in the community. Middlebrook subdivision offers expansive acreage with full approval for outbuildings and barndominiums, giving you the freedom to design a residence that blends architectural creativity with refined country elegance. With generous space, exceptional privacy, and a well

  

  Walt Schumm

  RE/MAX Real Estate Champions

  7008 Middlebrook Dr Unit Lot 2, Crestwood, KY 40014
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  /61

  $525,000

  • 4 Beds
  • 2.5 Baths
  • 2,770 Sq Ft

  4205 Evergreen Rd, Crestwood, KY 40014

  Bear's Gone Fishing! Welcome to your own private retreat on 2.6 beautiful acres in Crestwood, Kentucky-where peaceful mornings, stocked pond fishing, and tree-lined surroundings create the perfect escape from the everyday. Set well back from the road for added privacy, this lovingly maintained 4-bedroom, 2.5-bath home has been thoughtfully updated by the same owner since 2011. Inside, you'll find

  

  Kristin Kidwell

  Kentucky Select Properties

  4205 Evergreen Rd, Crestwood, KY 40014
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  /2

  $299,000

  • Land
  • 6.9 Acres
  • $43,333 per Acre

  7007 Middlebrook Dr Unit Lot 19, Crestwood, KY 40014

  

  Walt Schumm

  RE/MAX Real Estate Champions

  7007 Middlebrook Dr Unit Lot 19, Crestwood, KY 40014
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  /2

  $229,000

  • Land
  • 2 Acres
  • $114,500 per Acre

  7012 Middlebrook Dr Unit Lot 3, Crestwood, KY 40014

  Discover elevated rural living on this distinguished parcel, where modern design possibilities meet serene natural surroundings. Lot 3 welcomes high end outbuildings and luxury barndominiums, allowing you to create a custom residence that reflects your personal style and standards.

  

  Walt Schumm

  RE/MAX Real Estate Champions

  7012 Middlebrook Dr Unit Lot 3, Crestwood, KY 40014
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  /99

  $652,000

  Open Sun 2PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 3,772 Sq Ft

  3205 W Mount Zion Rd, Crestwood, KY 40014

  "Living the dream," is what you will say about living here! Wonderful lakefront house in Oldham County's Lake Pointe neighborhood is located on a 1.18-acre lot with direct lake access. New carpeting, fresh paint, ready to move in! First floor primary suite! Kitchen opens to the breakfast room and the fabulous 2 story great room with vaulted ceilings, great light and views! The adjoining glassed

  Joanne Owen Kentucky Select Properties

  3205 W Mount Zion Rd, Crestwood, KY 40014
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  /84

  $739,000

  $11K PRICE DROP

  • 6 Beds
  • 4.5 Baths
  • 5,782 Sq Ft

  5314 High Crest Dr, Crestwood, KY 40014

  Welcome to your dream home in the highly sought-after Oldham County School District! Offering over 5,700 square feet of beautifully designed living space on a spacious 1.3-acre lot, this exceptional home offers the perfect blend of luxury, comfort, and functionality—with room for everyone and everything you need to live, work, & entertain with ease. Thoughtfully updated & truly move-in ready,

  Wendy Watson Homepage Realty

  5314 High Crest Dr, Crestwood, KY 40014
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  /62

  $899,900

  • 6 Beds
  • 4.5 Baths
  • 4,953 Sq Ft

  5600 Chapel View Way, Crestwood, KY 40014

  Freshly updated with new flooring throughout the second floor and basement, plus fresh interior paint throughout the home, this move-in ready property is better than ever! This stunning 6-bedroom (3 ensuite), 4.5-bath home with a finished walk-out basement is located in a desirable single-entry neighborhood in South Oldham County, featuring just 46 homes on 1+ acre lots and only 25 minutes from

  Jeni McNickle Homepage Realty

  5600 Chapel View Way, Crestwood, KY 40014
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  /56

  $460,000

  $20K PRICE DROP

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

  1618 Whittaker Rd, Crestwood, KY 40014

  Welcome to your peaceful retreat! Nestled on a beautiful 1-acre lot in the highly desirable Whit Acres subdivision, this charming 2-story split-level home offers 4 spacious bedrooms , 2 full bathrooms and a cozy family room with wood-burning fireplace, providing plenty of space for family and guests. The perfect balance of quiet country living and modern convenience. Enjoy the small-town feel of

  Caroline Gonzales EXP Realty LLC

  1618 Whittaker Rd, Crestwood, KY 40014
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  /16

  $220,000

  $20K PRICE DROP

  • Land
  • 1.7 Acres
  • $129,412 per Acre

  5508 Clover Ridge Dr, Crestwood, KY 40014

  Rare opportunity to build a custom house on 1.7 flat acres in the desirable neighborhood of Croftboro Farms in Oldham County. This lot provides a recently paved driveway, landscape curbing, and a large pole barn. There are plenty of mature trees for privacy with fruit bearing trees lining the back of the property. The pole barn was built in 2015, and features a 220-amp electrical panel, water

  Jillian Fritz Weichert Realtors-ABG

  5508 Clover Ridge Dr, Crestwood, KY 40014
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  /5

  $375,000

  • Land
  • 5.45 Acres
  • $68,807 per Acre

  0 W Hwy 22 Hwy Unit 1720637, Crestwood, KY 40014

  Excellent and rare opportunity to own this 5+ acre lot off Hwy 22. There is a barn on the property.

  Ellen Kronauer Family Realty LLC

  0 W Hwy 22 Hwy Unit 1720637, Crestwood, KY 40014
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  /64

  $865,000

  $35K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 4,791 Sq Ft

  4405 W State Highway 22, Crestwood, KY 40014

  Welcome home to 4405 W Hwy 22 - 4.4+ acres in Southern Oldham County surrounded by large-acreage properties and quiet country living. This home is ideal for the buyer who values a private pond, flat usable land, extensive garage and shop space, and outdoor living areas designed for everyday enjoyment. The 4400+ sq ft brick home has been meticulously updated and maintained, delivering both comfort

  Matt Weaver Coldwell Banker McMahan

  4405 W State Highway 22, Crestwood, KY 40014
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  /58

  $555,000

  • 4 Beds
  • 2 Baths
  • 2,700 Sq Ft

  1105 E Hwy 22, Crestwood, KY 40014

  Great cape cod on over an acre in Crestwood not in a subdivision! This charming cap cod has been beautifully updated and is move in ready! The house sits on just over an acre minutes to the local schools. The home has a first floor primary, hardwood floors on the main level. Two bedrooms and a bath on the second level. Lovely finished walk out basement. Outside you have a beautiful treed yard

  Patrick Pollard Pollard Realty

  1105 E Hwy 22, Crestwood, KY 40014
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  /5

  $200,000

  • Land
  • 1 Acre
  • $200,000 per Acre

  5504 Farmhouse Dr, Crestwood, KY 40014

  Beautiful pond view lot in Farmhouse Estates! Come build the home of your dreams with the builder you choose! Excellent fallaway ready for you to build your dream home! Nice mature trees and great views. The pond makes for a private rear yard. This is a great neighborhood in an excellent location with strong home values!

  Patrick Pollard Pollard Realty

  5504 Farmhouse Dr, Crestwood, KY 40014
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  /69

  $539,000

  • 4 Beds
  • 3 Baths
  • 4,882 Sq Ft

  4612 Glenarm Rd, Crestwood, KY 40014

  This spacious ranch-style home offers almost 3200 sq ft on the main level plus 1,688 sq ft of finished living space in the lower level. Nestled on a flat 1.77-acre lot, this property provides the perfect blend of comfort, versatility, and room to grow. Step inside to a welcoming foyer that opens to a large great room with access to the rear deck—ideal for indoor/outdoor living. The open floor

  Cindy Hack Finish Line Realty LLC

  4612 Glenarm Rd, Crestwood, KY 40014
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  /4

  $175,000

  $15K PRICE DROP

  • Land
  • 2.66 Acres
  • $65,789 per Acre

  6403 New Cut Rd Unit Tract 2, Crestwood, KY 40014

  Bask in nature on this wooded 2.663-acre retreat. This gorgeous property in Oldham County is the perfect place for your dream home. A successful percolation test has already been performed. Additional acreage is available and adjoins this property. Don't miss this incredible opportunity and schedule your showing today.

  Wendy Hayden Persimmon Tree Realty

  6403 New Cut Rd Unit Tract 2, Crestwood, KY 40014
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  /70

  $660,000

  $30K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 4,139 Sq Ft

  4615 Northridge Cir, Crestwood, KY 40014

  This Southern-style farmhouse welcomes you with a wonderful covered front porch in a well-kept neighborhood with sidewalks. Over 4,000 square feet of finished living space with 5 bedrooms and 4.5 baths, a finished walkout basement on 2 partially wooded acres in sought-after Northridge Farms subdivision located directly next to the award-winning Oldham County schools, East Oldham Middle and Locust

  David Ackerman United Real Estate Louisville

  4615 Northridge Cir, Crestwood, KY 40014
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  /49

  $400,000

  $15K PRICE DROP

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

  3107 Thoroughbred Ct, Crestwood, KY 40014

  Welcome to 3107 Thoroughbred Court. This fabulous, renovated, walkout ranch is located on a quiet cul-de-sac in the Kentucky Acres subdivision in Crestwood. Come fall in love with this gorgeous, semi secluded 1.13 property surrounded by mature trees. Turning onto this property brings you onto a newly paved driveway that leads up to the side entry 2 car garage. Follow the stairs around the front

  Jack May May Team REALTORS

  3107 Thoroughbred Ct, Crestwood, KY 40014
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  /51

  $550,000

  • 3 Beds
  • 3 Baths
  • 2,776 Sq Ft

  3822 Carriage Hill Dr, Crestwood, KY 40014

  Welcome to your own private countryside retreat in the heart of Crestwood. Nestled on 2.19 picturesque rolling acres, this storybook cottage-style home offers the perfect blend of timeless charm, modern comfort, and breathtaking natural beauty. Surrounded by mature perennial gardens, sweeping green space, and a tranquil pond, every season brings a new reason to fall in love with this

  Aleksandra Dovedan Realty Advanced

  3822 Carriage Hill Dr, Crestwood, KY 40014
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  /9

  $180,000

  $20K PRICE DROP

  • Land
  • 1.39 Acres
  • $129,496 per Acre

  5502 Farmhouse Dr, Crestwood, KY 40014

  Beautiful pond view lot in Farmhouse Estates! Excellent fallaway ready for you to build your dream home! Nice mature trees and great views. The pond makes for a private rear yard. This is a great neighborhood in an excellent location with strong home values!

  Patrick Pollard Pollard Realty

  5502 Farmhouse Dr, Crestwood, KY 40014
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  $875,000

  • 5 Beds
  • 4.5 Baths
  • 4,419 Sq Ft

  4009 Lake Ridge Way, Crestwood, KY 40014

  Welcome to an exceptional executive residence in the prestigious Clarke Pointe Estates, where over $135,000 in thoughtful upgrades have elevated this custom-built home into a truly remarkable retreat. Perfectly situated on a picturesque 1.32-acre lot overlooking a beautiful, stocked pond, this property offers the rare combination of luxury, privacy, and breathtaking open views. Designed for both

  Garrett Ackles Semonin Realtors

  4009 Lake Ridge Way, Crestwood, KY 40014
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  /2

  $1,600,000

  • 5 Beds
  • 7 Baths
  • 6,760 Sq Ft

  6405 Chatham Ct, Crestwood, KY 40014

  An exceptional opportunity awaits in prestigious Brentwood Estates, where luxury, privacy, and personalization come together to bring your dream home to life. Perfectly positioned on over an acre at the end of a quiet cul-de-sac, this custom-built residence offers a rare combination of peaceful surroundings and refined living in one of Oldham County's most desirable communities. Thoughtfully

  Emily Hughes Lenihan Sotheby's Int'l Realty

  6405 Chatham Ct, Crestwood, KY 40014
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  /100

  $689,900

  $10K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,769 Sq Ft

  3707 High Crest Ct, Crestwood, KY 40014

  Situated on 1.7 picturesque acres in the highly sought-after Woods of Hillview subdivision in Crestwood, this stunning brick 1.5-story home offers the perfect blend of space, comfort, and timeless elegance. Offering 5 bedrooms, 3.5 baths, and thoughtful updates throughout, this home is designed for both everyday living and entertaining. The inviting two-story family room features soaring vaulted

  Jennifer Downs 85W Real Estate

  3707 High Crest Ct, Crestwood, KY 40014
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  /3

  $250,000

  • 2 Beds
  • 1.5 Baths
  • 1,000 Sq Ft

  8330 Ballardsville Rd, Crestwood, KY 40014

  Rare investment opportunity for a 1,000 sqft, 100-year old cottage in highly desirable Crestwood - just minutes from I-71 and I-265, the Paddock and Springhurst shopping areas, and Norton Commons. Kenwood Station, SOMS, and SOHS school district. Situated on over 1 acre, this property offers tremendous potential for redevelopment as a rental cottage, renovation for a precious new home, or a

  Katie Wells Premier Homes Realty

  8330 Ballardsville Rd, Crestwood, KY 40014
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  /31

  $412,500

  $3K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,860 Sq Ft

  3508 Rock Rose Ln, La Grange, KY 40031

  Immaculate, beautifully updated, and move-in ready! This stunning 3-bedroom, 3-bath brick ranch is nestled on a beautifully landscaped 1-acre lot in the highly desirable Greenbriar Farms neighborhood of Oldham County. Step inside to discover luxury laminate flooring, stylish ceramic tile, brand-new carpet, and beautiful custom trim work throughout, adding elegance and craftsmanship to every room.

  David Meeron Premier Homes Realty

  3508 Rock Rose Ln, La Grange, KY 40031
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  /16

  $1,700,000

  $300K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,909 Sq Ft

  3300 W Highway 22, Crestwood, KY 40014

  Opportunity knocks! OLDHAM COUNTY DEVELOPMENT OPPORTUNITY 17.85 ACRES. Prime location at intersection of Hwy 22 and Hwy 329. Zoned R-2.

  Morgan Shallcross Semonin Realtors

  3300 W Highway 22, Crestwood, KY 40014
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  /42

  $520,000

  $10K PRICE INCREASE

  • 3 Beds
  • 2 Baths
  • 2,017 Sq Ft

  7705 Commonwealth Dr, Crestwood, KY 40014

  Welcome home to this immaculate and beautifully maintained all-brick walkout ranch in sought-after Kentucky Acres! Set on a private, park-like 1.18 acres, this 3-bedroom, 2-bath home offers a finished lower level and a stunning in-ground pool framed by mature Japanese maples and white vinyl fencing - your own backyard retreat. The main level features a vaulted great room with a brick fireplace

  Martha Hemminger simpler.realestate

  7705 Commonwealth Dr, Crestwood, KY 40014
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  /5

  $488,000

  • Land
  • 8 Acres
  • $61,000 per Acre

  6401 6403 6405 New Cut Rd, Crestwood, KY 40014

  Discover the perfect setting for your dream home on 8 wooded private acres in CRESTWOOD. Create your own secluded retreat surrounded by mature trees, natural beauty, and peaceful privacy. There are currently three tracts available, which may be purchased separately or together to create an expansive estate property. Each lot has successfully passed a percolation test and offers multiple potential

  Wendy Hayden Persimmon Tree Realty

  6401 6403 6405 New Cut Rd, Crestwood, KY 40014
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  /67

  $645,000

  • 2 Beds
  • 2.5 Baths
  • 2,214 Sq Ft

  1203 E Moody Ln, Crestwood, KY 40014

  Hobbyist or Multi Gen buyers, this is your dream come true!! This incredible property has been meticulously maintained since the seller built the home. Where to start! The main home is a fiber cement sided home with a metal roof. The HUGE front porch greets you as you approach the home. Inside you will find soaring ceilings with an open loft above and tongue and groove wood ceilings. The family

  Patrick Pollard Pollard Realty

  1203 E Moody Ln, Crestwood, KY 40014
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  /4

  $159,995

  • Land
  • 2.05 Acres
  • $78,046 per Acre

  3820 Carriage Hill Dr, Crestwood, KY 40014

  Don't miss this incredible opportunity to build the custom home you've always envisioned on this beautiful almost 2-acre lot in Oldham County. This scenic property provides plenty of space for your dream home, outdoor living, recreation, and gardening. Enjoy the peaceful surroundings while still being just minutes from shopping, dining, schools, parks, and major highways, which makes commuting

  Team Panella Keller Williams Collective

  3820 Carriage Hill Dr, Crestwood, KY 40014
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  /7

  $1,158,000

  • 4 Beds
  • 2.5 Baths
  • 2,848 Sq Ft

  6295 Sunset Cir, Crestwood, KY 40014

  Proposed custom home by Tracee Dore Builders in the highly desirable Brentwood community. Situated on a beautiful 1-acre wooded walkout lot in Crestwood, KY, this is your opportunity to build a home tailored to your lifestyle. Personalize every detail by selecting your own finishes from start to finish with the guidance of an experienced builder who also has a background in interior design.

  Wendy Hayden Persimmon Tree Realty

  6295 Sunset Cir, Crestwood, KY 40014
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  /89

  $2,375,000

  • 4 Beds
  • 4.5 Baths
  • 4,856 Sq Ft

  6711 Highway 329, Crestwood, KY 40014

  Exquisite Custom-Built Estate | One-Owner Home | Stunning Views in Every Direction - This extraordinary 1.5 story custom-built Estate, sitting on 6.57 acres, is a true one-of-a-kind masterpiece, meticulously designed & lovingly maintained by its original owner. From the moment you arrive, you'll appreciate the exceptional craftsmanship, timeless elegance, & breathtaking natural surroundings that

  Robin Hancock Semonin Realtors

  6711 Highway 329, Crestwood, KY 40014
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  /38

  $575,000

  $24K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 3,479 Sq Ft

  4416 Abbott Grove Dr, Crestwood, KY 40014

  Currently listed below appraised value in Oldham County, this beautiful, custom built home sits on 1.2 acres in Abbott Grove, a highly desirable Crestwood neighborhood that rarely has listings hit the market. The home has had one owner and is now ready for someone new to put their personal touch on the property and love it for the next 30 years. When you enter, the open concept immediately stands

  Craig Miller Keller Williams Collective

  4416 Abbott Grove Dr, Crestwood, KY 40014
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  /2

  $1,290,000

  • 5 Beds
  • 3.5 Baths
  • 4,069 Sq Ft

  316 Sunset Cir, Crestwood, KY 40014

  Beautiful ranch on more than an acre lot in highly sought after Brentwood subdivision. The open concept kitchen and living room with a vaulted ceiling, dual slider providing soft natural light, and tiled linear fireplace. The kitchen has it all with a large island with double sided cabinetry, beautiful custom cabinets to ceiling with glass lighted uppers, gorgeous quartz tops, a 36' cafe cooktop

  Stacy Conley Louisville Realty Group

  316 Sunset Cir, Crestwood, KY 40014
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  /45

  $435,000

  • 3 Beds
  • 2 Baths
  • 2,288 Sq Ft

  3612 Echo Valley Cir, Lagrange, KY 40031

  Enjoy peaceful country living just minutes from La Grange, with quick access to I-71 and shopping along the KY 393 corridor. This charming 3-bedroom, 2-bath brick ranch sits on approximately 1.22 acres and features new flooring, a recently remodeled kitchen and both bathrooms, a finished walkout basement, fireplace, and two-car garage. The versatile lower level offers space for recreation,

  Angela Klehr Biddle Realty

  3612 Echo Valley Cir, Lagrange, KY 40031
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  /40

  $450,000

  • 3 Beds
  • 1 Bath
  • 1,969 Sq Ft

  6123 W Highway 146, Crestwood, KY 40014

  A wonderful 125+ year old farmhouse with updates galore. This well taken care of home has 3 bedrooms and 1 full bath. Located in the Oldham school district. The buyer will love the tree lined driveway and circle drive that leads to the covered side porch or the front door. As you enter the house the history is abundant with beautiful trim work from a time past. Hardwood floors in the living room

  Betty Rodgers Weichert Realtors-H. Barry Smith Co.

  6123 W Highway 146, Crestwood, KY 40014
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  /12

  $2,850,000

  • Land
  • 61.4 Acres
  • $46,417 per Acre

  6296A Sunset Cir, Crestwood, KY 40014

  Over 60 acres of private unrestricted acres! A rare find in Oldham County Kentucky! just 10 minutes to Louisville and Eastern Jefferson County! This 61.4 acres is located just off I-71 Exit 14 and is a wooded private heavenly retreat with hiking trails, campsites, picnic area and even Long Creek frontage with multiple water falls and fishing holes. This Blueline Stream frontage is over 1800 feet

  Steve Hall Homepage Realty

  6296A Sunset Cir, Crestwood, KY 40014
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  /38

  $550,000

  • 4 Beds
  • 3 Baths
  • 3,073 Sq Ft

  2410 Eastwood Cir, Crestwood, KY 40014

  Great Room/Dining Area has an open floor plan concept with vaulted ceilings and oak hardwood floors. The Finished Walkout Basement has raised ceilings with additional storage space. Great space for a Family Room with built-in book shelves and access to the rear patio. The Fourth Bedroom located upstairs would make a great teen quarters, home office or game room. Kitchen offers granite counter

  Scott Kahle Keller Williams Collective

  2410 Eastwood Cir, Crestwood, KY 40014

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