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Recently Sold Old Pine Grove Homes

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  • /33

    $240,000 Sold Sep 10, 2025

    • 2,472 Sq Ft
    • $97/SF
    • 18 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1969

    752 Wayland Dr, Winchester, KY 40391

    This ranch style house is located minutes from Fayette County line and minutes from the I-64 and I-75 corridors. This house features 4 bedrooms and 2 full baths on a walk-out basement. The owners remodeled several years ago with new kitchen and primary suite. The house is situated on a .53 acre lot within a quiet residential neighborhood. Looking for a house to make your home? come see this

    Craig Bridgewater Bridgewater Real Estate

    752 Wayland Dr, Winchester, KY 40391
  • /33

    $385,000 Sold Sep 04, 2025

    • 2,741 Sq Ft
    • $140/SF
    • 12 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1985

    113 Shala Mar Rue, Winchester, KY 40391

    Beautifully maintained brick ranch on a full basement, offering over 4,000 square feet under roof in a highly desirable location just minutes from Hamburg, I-64, Lexington, and Clark County Regional Hospital. This spacious home features 4 bedrooms, 3 full baths, and stunning hardwood floors. Two impressive floor-to-ceiling fireplaces add charm on both levels. The kitchen includes new stainless

    Rebakah Goodpaster Keller Williams Legacy Group

    113 Shala Mar Rue, Winchester, KY 40391
  • /41

    $259,900 Sold Aug 31, 2025

    • 1,544 Sq Ft
    • $168/SF
    • 6 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2006

    315 Newcastle Ln, Winchester, KY 40391

    Nestled in a cul-de-sac in Winchester's Oakmont neighborhood, this 3-bedroom, 2.5-bath home offers comfort and convenience. The main level features vinyl plank flooring throughout, a spacious living room, and an eat-in kitchen, plus a laundry area and half bath. Upstairs, you'll find three generously sized bedrooms, including a primary suite with a walk-in closet and private bath. A second full

    Terra Long Keller Williams Commonwealth

    315 Newcastle Ln, Winchester, KY 40391
  • /34

    $369,500 Sold Aug 22, 2025

    • 2,456 Sq Ft
    • $150/SF
    • 11 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2022

    148 Gibson Way, Winchester, KY 40391

    NEW PRICE!Better Than New Construction!!! This Spacious 4 Bedroom 2 1/2 Bath Home Is Move In Ready And Has A Beautiful Farm View From Your Covered Porch. Features Include A Large Open Living Room And Kitchen With Plenty Of Cabinet Space; Large Island With Faucet; Granite Countertops; Tile Backsplash; Stainless Steel Appliances; Large pantry; Gas Log Fireplace; Gas Heat; Gas Water Heater;

    W Patrick Arvin Keller Williams Commonwealth

    148 Gibson Way, Winchester, KY 40391
  • /54

    $269,900 Sold Aug 12, 2025

    • 1,536 Sq Ft
    • $176/SF
    • 11 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2006

    137 Sturbridge Ln, Winchester, KY 40391

    This lovely story and a half home is conveniently located close to Bypass road with easy access to everything Winchester has to offer. The main floor offers a comfortable living area that connects to the spacious eat-in kitchen, a convenient half bathroom, and the laundry room. Take a step out the back patio door to experience the generous, shaded, privacy fenced back yard perfect for kids or

    Josh Wood Freedom Realty & Property Management

    137 Sturbridge Ln, Winchester, KY 40391
  • /41

    $279,900 Sold Aug 12, 2025

    • 1,808 Sq Ft
    • $155/SF
    • 8 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2006

    225 Prescott Ln, Winchester, KY 40391

    What are your thoughts on a residence featuring a prime location, within walking distance to several schools? Now that I've got your interest, the primary bedroom is situated on the main level. How do three or possibly four bedrooms, accompanied by 2.5 bathrooms, sound? This residence is located in the Oakmont subdivision and has been under the same ownership for over 15 years. Don't miss your

    Teresa Richmond Freedom Realty & Property Management

    225 Prescott Ln, Winchester, KY 40391
  • /21

    $285,000 Sold Jul 29, 2025

    • 1,696 Sq Ft
    • $168/SF
    • 8 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2004

    219 Bartram Ct, Winchester, KY 40391

    This charming residence features a desirable first-floor primary bedroom and a spacious kitchen complete with a breakfast bar—perfect for everyday living and entertaining. Enjoy peace of mind with a brand-new roof and updated systems throughout. Located in a sought-after neighborhood close to everything you need. Don't miss the opportunity to make this home yours—schedule your showing today!

    Nora Williams Keller Williams Commonwealth

    219 Bartram Ct, Winchester, KY 40391
  • /40

    $240,000 Sold Jul 29, 2025

    • 2,617 Sq Ft
    • $92/SF
    • 12 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1980

    400 Verna Dr, Winchester, KY 40391

    Spacious Brick Ranch with Dual Master Suites & Investor Potential! This charming 5-bedroom, 3-bath brick ranch is nestled in a well-established neighborhood and offers a rare opportunity for customization and value-add. With some renovation projects already started, this home is ideal for an investor or handy homeowner ready to build instant equity.Enjoy the flexibility of two master

    Melodie Lincavage RE/MAX Elite Realty

    400 Verna Dr, Winchester, KY 40391
  • /28

    $234,500 Sold Jul 29, 2025

    • 1,200 Sq Ft
    • $195/SF
    • 45 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2004

    108 Sturbridge Ln, Winchester, KY 40391

    Gorgeous one story home located just off the Winchester Bypass. This lovely home has three bedrooms and two full baths with a two car attached garage and deck out back. Fenced in yard!!!! Don't miss out; this one will go FAST!!! NOTE: Property must be listed for 5 days before seller will look at any offers

    Jason Szaks EXIT TOWN & COUNTRY REALTORS

    108 Sturbridge Ln, Winchester, KY 40391
  • /32

    $285,000 Sold Jul 03, 2025

    • 1,690 Sq Ft
    • $169/SF
    • 168 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1976

    602 Laura Dr, Winchester, KY 40391

    MOTIVATED SELLERS. Find peace in this updated all-brick ranch that's made for summer fun and year-round comfort — complete with an in-ground pool, walk-out basement, and a backyard that's calling for your next BBQ. Tucked in a quiet neighborhood just over the Fayette County line, you're only 10 minutes from Hamburg, giving you the best of both convenience and calm.Inside, this 3 bedroom,

    Ryan O'Gara Real Broker, LLC

    602 Laura Dr, Winchester, KY 40391
  • /28

    $265,000 Sold Jul 02, 2025

    • 1,305 Sq Ft
    • $203/SF
    • 2 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1980

    609 Clintonville Rd, Winchester, KY 40391

    Location, location, location! This house is located on a .48 Kentucky Bluegrass lot in a residential neighborhood, Wayland Heights. And within minutes you can be at the Hamburg area of Lexington or to the Historical Downtown Winchester. The owners of this home remodeled interior, added new windows, gutters and facia trim and painted the exterior of the house. The great room is a welcoming space

    Craig Bridgewater Bridgewater Real Estate

    609 Clintonville Rd, Winchester, KY 40391
  • /22

    $334,327 Sold Jul 01, 2025

    • 1,997 Sq Ft
    • $167/SF
    • 219 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2024

    136 Gibson Way, Winchester, KY 40391

    The Laurel Square, part of the Trend Collection by Ball Homes, is two story plan with a very open first floor layout. The island kitchen offers both a breakfast area and countertop dining, and a large pantry. Granite kitchen counter tops with stainless steel 50/50 under-mount sink and full back splash. Stainless steel appliances including smooth top range, microwave and dishwasher. The kitchen

    Neshia Gaines Christies International Real Estate Bluegrass

    136 Gibson Way, Winchester, KY 40391
  • /31

    $231,000 Sold Jun 30, 2025

    • 1,404 Sq Ft
    • $165/SF
    • 17 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1980

    619 Laura Dr, Winchester, KY 40391

    This beautiful 3-bedroom ranch is ready for you to make it your own. The home boasts 1400 SQ FT and has a wonderful floor plan. Step inside and check out the living room, which has great natural light and lots of space to relax or enjoy company. Home also has a bonus room next to the living room that adds a ton of space for living, work, or play. The formal dining area allows for easy mealtimes

    Kevin Bradley KB Realty Group

    619 Laura Dr, Winchester, KY 40391
  • /58

    $850,000 Sold Jun 27, 2025

    • 2,980 Sq Ft
    • $285/SF
    • 1 Day On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1988

    2158 Venable Rd, Winchester, KY 40391

    Perched upon 5.34 acres of flat land, this idyllic white farmhouse is ready to be loved by new owners! The property is fully fenced and has a gated entry. Step inside to an open floor plan with gleaming hardwoods throughout the main level. The family room with wood-burning stove flows into a spacious dining area. The beautifully renovated kitchen is complete with custom cabinetry, large walk-in

    Emily Miller Bluegrass Sotheby's International Realty

    2158 Venable Rd, Winchester, KY 40391
  • /65

    $290,000 Sold Jun 18, 2025

    • 1,844 Sq Ft
    • $157/SF
    • 1 Day On Market
    • 3 Beds
    • 2 Baths
    • Built 1980

    13 Robyn Dr, Winchester, KY 40391

    It is hard to find a home that has been as meticulously maintained as this one! Nestled in the wonderful neighborhood of Verna Hills, this 3 bedroom, 2 full bath, one level brick home is turn key ready to move in! All of the major expense items have been replaced in the last few years such as the HVAC, water heater, and the metal roof! Out back you will find a lovely covered patio, a storage

    Jason Townsend Kentucky Residential Real Estate, LLC

    13 Robyn Dr, Winchester, KY 40391
  • /35

    $265,000 Sold Jun 18, 2025

    • 2,240 Sq Ft
    • $118/SF
    • 82 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1974

    606 Laura Dr, Winchester, KY 40391

    Exceptional value! Now offered at a compelling new price. This charming ranch home with a full finished walkout basement in Verna Hills offers incredible space and comfort. Just minutes from Lexington & Winchester. This spacious ranch home offers 3 bedrooms and 2.5 baths. New vinyl windows throughout (except the front living room). Large kitchen with new appliances that is open and offers

    Bradley Morgan The Local Agents

    606 Laura Dr, Winchester, KY 40391
  • /27

    $275,000 Sold Jun 13, 2025

    • 1,726 Sq Ft
    • $159/SF
    • 129 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2008

    216 Prescott Ln, Winchester, KY 40391

    Conveniently located near shopping centers, schools and 6 minutes from the hospital. This home opens to a large den area which could easily be used for dining or flex space. The kitchen has plenty of room for entertaining with an island that opens to a spacious living room with fireplace. Plenty of room for parking in the attached garage. Upstairs features a separate laundry room, bedrooms and

    Brittany Lewis National Real Estate

    216 Prescott Ln, Winchester, KY 40391
  • /15

    $249,900 Sold Jun 09, 2025

    • 1,463 Sq Ft
    • $171/SF
    • 17 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2005

    234 Prescott Ln, Winchester, KY 40391

    Welcome Home! This stunning 1.5-story home is ready for its next owner! The primary suite is conveniently located on the ground floor, featuring a large walk-in closet for all your storage needs. The cozy living room boasts vaulted ceilings, creating an open, airy feel, while the brand-new tile shower in the full downstairs bathroom adds a touch of modern elegance. Upstairs, you'll find two

    Darrell Tackett Dream Maker Realty, LLC

    234 Prescott Ln, Winchester, KY 40391
  • /34

    $366,500 Sold Jun 05, 2025

    • 2,496 Sq Ft
    • $147/SF
    • 56 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2020

    112 Gibson Way, Winchester, KY 40391

    Amazing space in this 4 bedroom 3 bath home located in a great neighborhood, almost brand new well maintained, call today, close to shopping, churches, schools, I-64 and I-75, Richmond and Lexington,

    Mila Ensor Ensor Real Estate, LLC

    112 Gibson Way, Winchester, KY 40391
  • /37

    $207,000 Sold May 23, 2025

    • 1,120 Sq Ft
    • $185/SF
    • 41 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1974

    632 Laura Dr, Winchester, KY 40391

    Discover the perfect blend of comfort and convenience in this charming 3-bedroom home, nestled in a sought-after neighborhood. Boasting a spacious fenced-in backyard, it's an ideal retreat for privacy and outdoor enjoyment. This gem offers a harmonious balance of community feel and personal sanctuary. Welcome to your dream home where memories await!'

    Dale Hatton Dream Maker Realty, LLC

    632 Laura Dr, Winchester, KY 40391
  • /2

    $366,363 Sold May 22, 2025

    • 2,269 Sq Ft
    • $161/SF
    • 162 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2024

    140 Gibson Way, Winchester, KY 40391

    This Haywood Park is framed and at plumbing stage, is part of the Trend Collection by Ball Homes. It's a two story plan on a walk-out basement with plenty of room to grow! When you walk through the front door, you're greeted with a versatile flex space then down the hall opens up to the large living room and spacious kitchen. Cozy up next to the fireplace or sip your morning coffee outside on

    Neshia Gaines Christies International Real Estate Bluegrass

    140 Gibson Way, Winchester, KY 40391
  • /2

    $374,738 Sold May 20, 2025

    • 2,519 Sq Ft
    • $149/SF
    • 9 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 2024

    138 Gibson Way, Winchester, KY 40391

    Contract writing period through 12:00 noon on Thursday, November 7th.The Sycamore Bend, part of the Trend Collection by Ball Homes, is a two-story plan that includes a first-floor guest bedroom. The plan offers a versatile flex room off the entry and an open kitchen and family room at the rear of the home. The kitchen offers both a breakfast area, countertop dining at the island, and a

    Jennifer Sisson Christies International Real Estate Bluegrass

    138 Gibson Way, Winchester, KY 40391
  • /22

    $332,000 Sold Apr 25, 2025

    • 2,384 Sq Ft
    • $139/SF
    • 203 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2004

    502 Hewlett Ct, Winchester, KY 40391

    OPEN HOUSE, Saturday, March 22, 2025 from 12-2Happiness is this two story home with lots of room, great corner lot, large patio for entertaining and grilling, great room, master bedroom with large closet, close to shopping, schools, hospital, restaurants, double garage, located on a cul-de-sac, call today!

    Mila Ensor Ensor Real Estate, LLC

    502 Hewlett Ct, Winchester, KY 40391
  • /49

    $442,500 Sold Apr 18, 2025

    • 3,882 Sq Ft
    • $114/SF
    • 134 Days On Market
    • 6 Beds
    • 3.5 Baths
    • Built 2005

    321 Frontier Way, Winchester, KY 40391

    OPEN HOUSE Saturday 3/1/25 2-4pm. Apart from home being in a great location, right across the street from the Elementary School, home is minutes from shopping, food and entertainment (Applebees,Woody's Bar and Grill, Tjmaxx, Kroger, Movie Theatre, Ft. Boonesborough) & only a 20 minute drive to Hamburg in Lexington or 15 miutes to Mt. Sterling. This beautiful home is complete with a newly

    Olivia White Deborah Ball Realty

    321 Frontier Way, Winchester, KY 40391
  • /32

    $283,000 Sold Apr 03, 2025

    • 1,650 Sq Ft
    • $172/SF
    • 3 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2004

    193 Prescott Ln, Winchester, KY 40391

    Step into a bright, airy living room filled with natural light. The spacious kitchen boasts ample cabinetry, generous workspace, and room for a dining table—perfect for creating memorable meals. Step through to a delightful patio and fenced backyard, ideal for entertaining, kids, or pets. A conveniently located laundry room sits just off the kitchen. Upstairs, a versatile loft awaits—ideal as an

    Justin Satterwhite SimpliHOM

    193 Prescott Ln, Winchester, KY 40391
  • /26

    $220,000 Sold Feb 28, 2025

    • 1,108 Sq Ft
    • $199/SF
    • 3 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1978

    636 Laura Dr, Winchester, KY 40391

    Be the first in line to view this ranch home, centrally located close to Lexington, Winchester, I75, I64, Hamburg shopping, churches, schools, hospital, 3 bedroom, 1/ 1/2 bath, hardwood, tile, LVT, remodeled bathroom, well maintained home, call today

    Mila Ensor Ensor Real Estate, LLC

    636 Laura Dr, Winchester, KY 40391
  • /38

    $221,700 Sold Feb 10, 2025

    • 1,952 Sq Ft
    • $114/SF
    • 63 Days On Market
    • 3 Beds
    • 1 Bath

    104 Caudill Dr, Winchester, KY 40391

    Outstanding LOCATION!!! Discover the perfect blend of convenience and comfort in beautiful Winchester, KY. This home offers 3 bedrooms, 1 full bath, a large den, a spacious living room, and a newly updated kitchen. Recently professionally painted interior and new carpet throughout makes this one move in ready. A partial basement offers a laundry area, a bonus room, and a mechanical area. The home

    Joshua Brown Mike Brown Real Estate & Auction Co, LLC

    104 Caudill Dr, Winchester, KY 40391
  • /28

    $278,500 Sold Dec 06, 2024

    • 1,825 Sq Ft
    • $153/SF
    • 52 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1970

    209 Robyn Dr, Winchester, KY 40391

    Welcome to this beautiful, newly renovated 3 bedroom 2 1/2 bathroom ranch on a finished basement. Inside you'll find all new flooring and new paint throughout. Brand new white cabinets and granite countertops located in the kitchen. On the first floor is a primary bedroom with en suite bathroom and 2 other bedrooms. Downstairs you''ll find a half bath and family room. Lastly, the nicely treed

    Allison Haas Building The Bluegrass Realty

    209 Robyn Dr, Winchester, KY 40391
  • /26

    $275,000 Sold Dec 05, 2024

    • 1,727 Sq Ft
    • $159/SF
    • 64 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2007

    425 Wellington Way, Winchester, KY 40391

    Move in and relax! This beautiful property has been meticulously updated and ready for you to enjoy. This spacious home sits on a huge corner lot with a fenced in backyard in an ideal location. Close to shopping, restaurants, I64 and 16 miles to Hamburg. The first floor offers a family room plus a living/dining room area open to the freshly updated kitchen with new quartz countertops, tiled

    Tonya Skeens RE/MAX Elite Lexington

    425 Wellington Way, Winchester, KY 40391
  • /30

    $219,900 Sold Nov 22, 2024

    • 1,220 Sq Ft
    • $180/SF
    • 4 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2005

    142 Sturbridge Ln, Winchester, KY 40391

    Charming ranch with open floor plan, vaulted ceilings, and laminate flooring throughout. No carpet anywhere and enjoy no steps! Spacious primary bedroom with ensuite and walk in closet. Separate utility room right off the garage. Fenced in back yard and last but not least a newer HVAC system. Conveniently located right off the bypass behind Lowe's and close to grocery, restaurants, and the

    Terra Long Keller Williams Commonwealth

    142 Sturbridge Ln, Winchester, KY 40391
  • /32

    $305,000 Sold Nov 08, 2024

    • 1,834 Sq Ft
    • $166/SF
    • 16 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1990

    118 Shala Mar Rue, Winchester, KY 40391

    Welcome to this attractive ranch brick home in the desirable Shala Mar neighborhood! Located on a spacious .41-acre corner lot, this property features a fenced-in yard with lush landscaping and plenty of shade, perfect for entertaining. Enjoy the outdoor amenities including a Trex/wood deck surrounding an 18' Stealth semi-inground pool (installed by Aurora in Aug. 2021), a cozy fire pit, and a

    Michelle Blackburn RE/MAX Creative, Winchester

    118 Shala Mar Rue, Winchester, KY 40391
  • /25

    $215,000 Sold Oct 25, 2024

    • 1,159 Sq Ft
    • $186/SF
    • 50 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2005

    141 Sturbridge Ln, Winchester, KY 40391

    Your wait is over, Dont drag your feet or this one will be gone. This beautiful home boast 3 bedrooms, 2 full baths, 2 car garage . The cathedral ceilings make it feel open and free . large Primary Bedroom with nice size walk in closet. Nice stainless steal appliances in the kitchen. HVAC system is only 3 years old along with recently replaced kitchen appliances as well. The home has a nice

    Wayne Elkins RE/MAX Creative Realty

    141 Sturbridge Ln, Winchester, KY 40391
  • /17

    $328,000 Sold Sep 26, 2024

    • 2,064 Sq Ft
    • $159/SF
    • 26 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2021

    106 Gibson Way, Winchester, KY 40391

    Home built in 2021 and located just minutes from Winchester bypass and 20 minutes to Lexington. Preschool, elementary and intermediate school within walking distance. Main floor features family room open to kitchen and dining area. Three bedrooms on second floor with two full bathrooms, washer/dryer hookup and bonus/loft area. Call today to schedule your showing! *Owner/Agent

    Brittany Lewis National Real Estate

    106 Gibson Way, Winchester, KY 40391
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