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Explore Similar Condos Within 2 Miles of Castlewood, KY

  • /21

    $400,000

    • 2 Beds
    • 2 Baths
    • 1,434 Sq Ft

    355 S Broadway Unit 202, Lexington, KY 40508

    A rooftop pool and stunning downtown Lexington views are just two favorite features of Centre City Condominiums. Add to that close proximity to LexLive and Rupp Arena, and you have a winning combination! A generous entry foyer leads to a great room and spacious kitchen with lots of cabinets and updated appliances. Two full bathrooms and in-unit laundry are perfect for hosting guests or

    Kyle Rogers Keller Williams Louisville East

    355 S Broadway Unit 202, Lexington, KY 40508
  • /29

    $459,900

    • 2 Beds
    • 2 Baths
    • 1,727 Sq Ft

    200 W Second St Unit 300, Lexington, KY 40507

    Rare opportunity to own a two-story penthouse in a prime downtown location—just steps from Rupp Arena, Transylvania University, Gratz Park, the Opera House, and a variety of local dining and entertainment options. This open-concept loft features exposed brick, hardwood floors, and a striking spiral staircase. Large windows flood the space with natural light. The first-floor bedroom includes a

    Emily Miller Bluegrass Sotheby's International Realty

    200 W Second St Unit 300, Lexington, KY 40507
  • /27

    $330,000

    • 1 Bed
    • 1.5 Baths
    • 851 Sq Ft

    369 E Main St Unit 304, Lexington, KY 40507

    Welcome to a sleek, updated modern condo nestled in the vibrant heart of downtown Lexington. This home is ideal for anyone looking to experience urban living at its finest, with easy walking access to a variety of shops, exciting events, and nightlife spots. Inside, the condo boasts a sophisticated design, blending contemporary finishes with clean lines and an open-concept layout that maximizes

    Michelle Gunter Bluegrass Home Group

    369 E Main St Unit 304, Lexington, KY 40507
  • /46

    $394,900

    • 2 Beds
    • 1.5 Baths
    • 937 Sq Ft

    369 E Main St Unit 501, Lexington, KY 40507

    Upscale Downtown Living at its Finest, located Across the Street from Carson's and Within Walking Distance to Everything—Don't Miss Out on this 2 Bedroom, 1.5 Bath Condo—Large Master 12x14 and Home Office 10x12 that Can Easily be Used as a 2nd Bedroom (no closet)---Top Floor Unit Allows for Taller Ceilings than the Other Units Providing a Much More Spacious Feel---Checkout ALL the

    Bret Hansen Four Seasons Realty

    369 E Main St Unit 501, Lexington, KY 40507
  • /32

    $387,000

    • 2 Beds
    • 2 Baths
    • 1,442 Sq Ft

    355 S Broadway Unit 402, Lexington, KY 40508

    Welcome to this beautiful 2-bedroom condo in downtown Lexington. This updated condo blends historic charm with modern amenities. Just steps from Rupp Arena, dining, shopping, and more, it offers the best of downtown living. The spacious interior features a fully equipped kitchen, in-unit washer and dryer, and elegant design throughout. Enjoy two comfortable bedrooms, two full bathrooms, a

    Donna Mink Mink Realty

    355 S Broadway Unit 402, Lexington, KY 40508
  • /49

    $2,299,000

    • 3 Beds
    • 3 Baths
    • 2,876 Sq Ft

    505 W Main St Unit 501, Lexington, KY 40507

    Experience refined downtown living in this elegant, two-story penthouse perched atop the 500s on Main, offering stunning views of Lexington's skyline. Ideally located with downtown attractions, dining, and shopping right outside your door. This three-bedroom, three-bath condo features upscale, thoughtfully curated finishes & stylish decor throughout. Floor-to-ceiling windows flood the open living

    Rusty Underwood Christies International Real Estate Bluegrass

    505 W Main St Unit 501, Lexington, KY 40507
  • /21

    $240,000

    • 2 Beds
    • 1 Bath
    • 910 Sq Ft

    200 W Second St Unit 10, Lexington, KY 40507

    Welcome home to The Lofts at Gratz Park! This charming condo offers two spacious bedrooms and one full bathroom. With an open layout that showcases exposed brick walls. The beautifully restored building features a private entry foyer, secure exterior entrance, building security cameras, and elevator access. Ideally located in the heart of downtown—just steps from Rupp Arena, Transylvania

    Sarah Weber Keller Williams Louisville East

    200 W Second St Unit 10, Lexington, KY 40507
  • /23

    $699,500

    • 6 Beds
    • 1 Bath

    342 Waller Ave Unit 4B, 4C, 4J, 4F, 6K, Lexington, KY 40504

    Unique opportunity to purchase 5 beautifully renovated condos in the desirable Waller place community. This secure building feathers an elevator, swimming pool, and easy living with HOA amenities that include central heating and air, common area maintenance, management, sewer, water and trash collection. Four are 1/1, and one is a 2/1.5. All are occupied, renovated and have recent appraisals.

    Nancy Smith Rector Hayden Realtors

    342 Waller Ave Unit 4B, 4C, 4J, 4F, 6K, Lexington, KY 40504
  • /15

    $215,000

    • 3 Beds
    • 2 Baths
    • 989 Sq Ft

    1081 S Broadway Unit 405, Lexington, KY 40504

    Updated and move-in ready, this 3-bedroom, 2-bath top-floor condominium offers comfort, convenience, and low-maintenance living near the University of Kentucky. Enjoy brand-new LVP flooring, fresh interior paint, and peace of mind with a heating and air system that's just one year old and a water heater less than six months old. The spacious layout provides a functional design for roommates or a

    Brad Lawson Show Place Realty

    1081 S Broadway Unit 405, Lexington, KY 40504
  • /24

    $170,000

    • 1 Bed
    • 1 Bath
    • 456 Sq Ft

    145 Virginia Ave Unit 106, Lexington, KY 40508

    Charming Studio Condo in Prime Lexington LocationWelcome to 145 Virginia Ave, #106 a delightful studio/efficiency condo nestled in the heart of Lexington, KY. Perfect for those seeking a blend of convenience and comfort, this charming unit offers a fantastic opportunity for first-time homebuyers, young professionals, or investors.

    Suresh Mallichettiar Jayaraman Keller Williams Bluegrass Realty

    145 Virginia Ave Unit 106, Lexington, KY 40508
  • /35

    $270,000

    • 1 Bed
    • 1.5 Baths
    • 862 Sq Ft

    121 N Martin Luther King Blvd Unit 401, Lexington, KY 40507

    If you are looking for a great corner unit with a view than you have found it. This 4th floor unit has a great view of downtown Lexington along with garage parking and an elevator and secured entry. Unit 401 is located in the historic Nunn building and just moments from the Kentucky Theater, Rupp, The Opera House, Gratz Park, UK and Transy along with Bars, Dining and so so much more.

    Brandon Hedinger Keller Williams Bluegrass Realty

    121 N Martin Luther King Blvd Unit 401, Lexington, KY 40507
  • /40

    $659,000

    • 2 Beds
    • 2 Baths
    • 1,437 Sq Ft

    355 S Broadway Unit 102, Lexington, KY 40508

    Coming Soon!! In the heart of downtown Lexington. No expense spared in this head turning remodeled '23, 2 full BDRM 2 full BA condo. Experience true indoor/outdoor living in the city with the folding glass doors open to the wrap around terrace with its' own living/bar area. Terrace area also features gas fire-pit and turf. Seldom offered 1st floor unit. Only 4 in the building have this extended

    Lynne Sneed Lynne Sneed Real Estate

    355 S Broadway Unit 102, Lexington, KY 40508
  • /19

    $245,000

    • 1 Bed
    • 1 Bath
    • 1,358 Sq Ft

    201 Price Rd Unit 103, Lexington, KY 40511

    Enjoy living in a true loft building in downtown Lexington. FULLY FURNISHED from sheets to silverware. High ceilings, large windows and lots of flexible space, indoor garage and storage building. Gym also included. This is an estate sale, call for your private showing today

    Melisa McDonald Wrenn Realty

    201 Price Rd Unit 103, Lexington, KY 40511
  • /61

    $3,795,000

    • 3 Beds
    • 3.5 Baths
    • 5,989 Sq Ft

    103 S Limestone Unit 1150, Lexington, KY 40507

    Welcome to this stunning high-end fully furnished luxury condo located in The Penthouses of City Center in the heart of downtown Lexington. This state of the art condo boasts of marble flooring throughout and breathtaking floor-to-ceiling glass windows that offer panoramic views of three different city skylines. Step outside onto one of the two balconies and experience the bustling energy of

    Whitney Durham Bluegrass Sotheby's International Realty

    103 S Limestone Unit 1150, Lexington, KY 40507
  • /17

    $268,800

    • 1 Bed
    • 1 Bath
    • 582 Sq Ft

    650 S Mill St Unit 219, Lexington, KY 40508

    Discover the perfect blend of comfort and convenience in this condo located in the heart of Lexington. Featuring sleek stainless steel appliances and an open-concept layout, this second-floor unit provides ample natural lighting. Enjoy your morning coffee or unwind after a long day on your private balcony. Just steps away from the University of Kentucky's campus, this prime location offers easy

    Cherise Wilson Diamond Key Realtors

    650 S Mill St Unit 219, Lexington, KY 40508
  • /21

    $254,500

    • 3 Beds
    • 2 Baths
    • 959 Sq Ft

    1081 S Broadway Unit 104, Lexington, KY 40504

    Rare opportunity to own a unit in Campus View Condominiums. Walking distance to UK, close to downtown, Transylvania University, St.Joseph Hospital, UK Hospitals and Red Mile. 3 bedroom, 2 full bath condo are great for investors, first-time homebuyers, or someone who wants to downsize. Walking distance to nearby restaurants-great location!

    Diana C Brooker Lifstyl Real Estate

    1081 S Broadway Unit 104, Lexington, KY 40504
  • /19

    $251,500

    • 2 Beds
    • 1 Bath
    • 850 Sq Ft

    251 Simpson Ave Unit 222, Lexington, KY 40504

    Great investment opportunity within walking distance of the University of Kentucky.

    Diana C Brooker Lifstyl Real Estate

    251 Simpson Ave Unit 222, Lexington, KY 40504
  • /21

    $255,000

    • 3 Beds
    • 2 Baths
    • 1,050 Sq Ft

    251 Simpson Ave Unit 220, Lexington, KY 40504

    Rare opportunity to own a unit in Campus Downs Condominiums. Walking distance to UK, close to downtown, Rupp Arena, Transylvania University, St.Joseph Hospital, UK Hospitals and Red Mile. 3 bedroom, 2 full bath condo are great for investors, first-time homebuyers, or someone who wants to downsize. Walking distance to nearby restaurants-great location! 3 BR 2 BA Condo

    Diana C Brooker Lifstyl Real Estate

    251 Simpson Ave Unit 220, Lexington, KY 40504
  • /21

    $258,850

    • 3 Beds
    • 2 Baths
    • 1,025 Sq Ft

    209 Simpson Ave Unit 302, Lexington, KY 40504

    Rare opportunity to own a unit in Campus Downs Condominiums. Walking distance to UK, close to downtown, Rupp Arena, Transylvania University, St.Joseph Hospital, UK Hospitals and Red Mile. 3 bedroom, 2 full bath condo are great for investors, first-time homebuyers, or someone who wants to downsize. Walking distance to nearby restaurants-great location!

    Diana C Brooker Lifstyl Real Estate

    209 Simpson Ave Unit 302, Lexington, KY 40504
  • /18

    $263,850

    • 3 Beds
    • 2 Baths
    • 1,025 Sq Ft

    205 Simpson Ave Unit 310, Lexington, KY 40504

    Rare opportunity to own a unit in Campus Downs Condominiums. Walking distance to UK, close to downtown, Rupp Arena, Transylvania University, St.Joseph Hospital, UK Hospitals and Red Mile. 3 bedroom, 2 full bath condo are great for investors, first-time homebuyers, or someone who wants to downsize. Walking distance to nearby restaurants-great location! 3 BR 2 BA Condo

    Diana C Brooker Lifstyl Real Estate

    205 Simpson Ave Unit 310, Lexington, KY 40504
  • /8

    $285,000

    • 2 Beds
    • 1 Bath
    • 870 Sq Ft

    1802 Carolyn Dr Unit 3, Lexington, KY 40502

    Updated condo in highly sought after 40502 area. The condo features hardwood floors, updated bathroom and kitchen, wonderful new light fixtures and tile work, storage area in the basement, and lots of parking in the private lot and on a quiet street. The patio area is in the process of being expanded.

    Hill Parker Turf Town Properties

    1802 Carolyn Dr Unit 3, Lexington, KY 40502
  • /23

    $299,000

    • 2 Beds
    • 1 Bath
    • 850 Sq Ft

    1802 Carolyn Dr Unit 4, Lexington, KY 40502

    Updated condo in highly sought after 40502 area. The condo features hardwood floors, updated bathroom and kitchen, wonderful new light fixtures and tile work, storage area in the basement, and lots of parking in the private lot and on a quiet street. The patio area is in the process of being expanded. A similar unit is coming in March if you want to pick your own colors and cabinets.

    Hill Parker Turf Town Properties

    1802 Carolyn Dr Unit 4, Lexington, KY 40502
  • /50

    $2,620,000

    • 3 Beds
    • 2 Baths

    205 Simpson Ave Unit 111, Lexington, KY 40504

    Multi Condominium Package Deal in Campus Downs Condominiums. Walking distance to UK, close to downtown, Rupp Arena, Transylvania University, St.Joseph Hospital, UK Hospitals and Red Mile. Walking distance to nearby restaurants-great location! 3 BR 2 BA Condo. 10 Properties - 9 Condominiums in Campus Downs on 205 Simpson Ave Units 111, 209, 216, 309, 310. 209 Simpson Ave Units 107, 302. 251

    Diana C Brooker Lifstyl Real Estate

    205 Simpson Ave Unit 111, Lexington, KY 40504
  • /46

    $2,249,000

    • 1 Bed
    • 2.5 Baths
    • 3,147 Sq Ft

    103 S Limestone Unit 1020, Lexington, KY 40507

    Elevate your living experience with this extraordinary City Center penthouse, offered fully furnished for effortless luxury. The avant-garde chef's kitchen features a stunning 16-foot quartz island with a waterfall edge, complemented by state-of-the-art Subzero and Wolf appliances—perfect for entertaining or indulging your culinary passions. A glass-enclosed flex space offers versatility as a

    James Turek Bluegrass Sotheby's International Realty

    103 S Limestone Unit 1020, Lexington, KY 40507
  • /2

    $247,000

    • 3 Beds
    • 2 Baths
    • 1,025 Sq Ft

    205 Simpson Ave Unit 216, Lexington, KY 40504

    Rare opportunity to own a unit in Campus Downs Condominiums. Walking distance to UK, close to downtown, Transylvania University, St.Joseph Hospital, UK Hospitals and Red Mile. 3 bedroom, 2 full bath condo are great for investors, first-time homebuyers, or someone who wants to downsize. Walking distance to nearby restaurants-great location! 3 bedroom 2 bathrooms

    Diana C Brooker Lifstyl Real Estate

    205 Simpson Ave Unit 216, Lexington, KY 40504
  • /2

    $255,000

    • 3 Beds
    • 2 Baths
    • 1,025 Sq Ft

    205 Simpson Ave Unit 309, Lexington, KY 40504

    Rare opportunity to own a unit in Campus Downs Condominiums. Walking distance to UK, Rupp Arena, close to downtown, Transylvania University, St.Joseph Hospital, UK Hospitals and Red Mile. 3 bedroom, 2 full bath condo are great for investors, first-time homebuyers, or someone who wants to downsize. Walking distance to nearby restaurants-great location! 3 BR 2 BA Condo

    Diana C Brooker Lifstyl Real Estate

    205 Simpson Ave Unit 309, Lexington, KY 40504
  • /2

    $255,000

    • 3 Beds
    • 2 Baths
    • 1,025 Sq Ft

    205 Simpson Ave Unit 209, Lexington, KY 40504

    Rare opportunity to own a unit in Campus View Condominiums. Walking distance to UK, close to downtown, Transylvania University, St.Joseph Hospital, UK Hospitals and Red Mile. 3 bedroom, 2 full bath condo are great for investors, first-time homebuyers, or someone who wants to downsize. Walking distance to nearby restaurants-great location! 3 bedroom 2 bathrooms

    Diana C Brooker Lifstyl Real Estate

    205 Simpson Ave Unit 209, Lexington, KY 40504

Why Live in Castlewood

Castlewood, a neighborhood in Lexington, features a variety of home styles including Craftsman, Cape Cod, ranch-style, and English Tudor cottages. These homes are generally modest in size, with most under 1,500 square feet and situated on lots no larger than a quarter-acre. The area is known for its walkability, thanks to narrow streets and sidewalks. Castlewood Park, one of Lexington’s largest and oldest parks, offers a range of recreational activities including basketball, tennis, baseball, and a popular Aquatic Center and Sprayground. The Loudoun House, managed by the Lexington Art League, provides historic tours and art exhibits. Castlewood's proximity to the eclectic North Limestone (NoLi) neighborhood adds to its appeal, with residents enjoying easy access to shops, restaurants, and venues like Greyline Station, North Lime Coffee & Donuts, and the Bespoken Spirits Lounge. For grocery shopping, ALDI and Walmart are nearby. The neighborhood is about 2 miles from downtown Lexington and close to major roads like New Circle Road and Interstates 64 and 75. Public transportation is available via Lextran bus stops on the neighborhood’s outskirts. Castlewood is also near Legends Field, home to the Lexington Legends baseball team, and Charles Young Park, which hosts the Eastside Evenings concert series.

Home Trends in Castlewood, KY

Housing Trends

Median Sale Price
$228,250
Median Single Family Sale Price
$238,500
Average Price Per Sq Ft
$187
Number of Homes for Sale
3
Last 12 months Home Sales
16
Months of Supply
2.30
Median List Price
$248,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
30%
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