Kentucky Square Real Estate

Kentucky Square Real Estate

Welcome to Kentucky Square, a charming and inviting subdivision nestled in the heart of Sanford, Florida, within the picturesque Seminole County. This delightful community is a hidden gem, offering residents a perfect blend of suburban tranquility and convenient access to urban amenities.

Kentucky Square is known for its beautifully designed homes, featuring a variety of architectural styles that cater to diverse tastes. Whether you’re seeking a cozy single-family home or a spacious residence for your growing family, this subdivision has something for everyone. The well-maintained streets are lined with lush landscaping and mature trees, creating a serene environment that encourages outdoor living and community interaction.

One of the standout features of Kentucky Square is its family-friendly atmosphere. With nearby parks, playgrounds, and recreational facilities, children can enjoy an active lifestyle while parents can relax knowing their little ones are safe and engaged. The community is also in close proximity to top-rated schools, making it an ideal location for families looking to settle down.

For those who enjoy shopping, dining, and entertainment, Kentucky Square is just a short drive away from downtown Sanford, where you can explore a variety of charming boutiques, delicious restaurants, and vibrant nightlife. Additionally, the scenic Lake Monroe and the St. Johns River provide ample opportunities for outdoor recreation, from fishing to boating.

Embrace the warmth and charm of Kentucky Square, where community spirit meets modern living in the beautiful city of Sanford. Your dream home awaits in this inviting subdivision!

Newest Listings in Kentucky Square

$487,990
4 Beds ⋅ 2 Baths ⋅ Kentucky Square SubDv. ⋅ 32773 Zip Code
Under Construction. Discover modern style and thoughtful design in this Wellington home at Kentucky Square in Sanford. The privacy-focused layout features no shared bedroom walls, while the open-concept family room flows seamlessly into the kitchen and dining area. A large island creates a natural gathering space, and the covered lanai extends the living area outdoors. Elevated finishes include 9’4” ceilings, ceramic tile throughout the main living areas, plush bedroom carpeting, and quartz countertops in the kitchen and all bathrooms. The kitchen showcases 42-inch cabinetry with soft-close doors, stainless steel appliances, a natural gas range, and an exterior-vented microwave. Additional features include a wall-tile surround in the primary bath, gutters, a Wi-Fi-enabled garage door opener, and a smart thermostat. Kentucky Square offers a pool, cabana, and playground within the A-rated Seminole County school district. Enjoy easy access to major roadways, Sanford International Airport, Lake Mary, Downtown Orlando, and Central Florida’s east coast beaches. Located approximately six miles from the Sanford Riverwalk, the community also places waterfront dining, breweries, parks, and scenic trails along Lake Monroe within easy reach.

3888 Triple Crown Loop, Sanford
$475,490
4 Beds ⋅ 3 Baths ⋅ Kentucky Square SubDv. ⋅ 32773 Zip Code
Virtually Staged. Pre-Construction. To be built. ***MAIN LEVEL LIVING***, *GUEST SUITE*, *KITCHEN ISLAND*, *WALK-IN PANTRY*, *COVERED LANAI!* The Webber B on Lot 146 at 3660 Triple Crown Loop offers thoughtful single-story living with open-concept spaces, a designer kitchen, private guest suite, spacious primary retreat, and an inviting lanai for easy indoor-outdoor living. Experience the lifestyle of Kentucky Square in desirable Sanford, just minutes from Lake Mary, Orlando Sanford International Airport, major roadways, shopping, dining, and recreation. Enjoy community amenities including a sparkling pool, cabana, and tot lot—perfect for relaxing, connecting, and enjoying Florida living. ***JOIN US Saturday 9/12/26 10:00am-12:00pm for our GRAND OPENING!*** Opportunities are limited—ask about current incentives and schedule your visit today. *Photos are of a similar home and may vary from actual home.

3660 Triple Crown Loop, Sanford
$499,990
5 Beds ⋅ 4 Baths ⋅ Kentucky Square SubDv. ⋅ 32773 Zip Code
Virtually Staged. Pre-Construction. To be built. ***MAIN LEVEL BR/FLEX ROOM***, *LOFT,* *SMART STORAGE*, *KITCHEN ISLAND*, *WALK-IN PANTRY*, *COVERED LANAI!* The Linden C on Lot 115 at 3727 Triple Crown Loop offers spacious two-story living with a versatile main-level bedroom/flex room, open-concept living, designer kitchen, inviting gathering spaces, and an upstairs loft ideal for movie nights, work, or play. The thoughtful layout also features ample storage and a private primary suite for everyday comfort. Experience the lifestyle of Kentucky Square in desirable Sanford, just minutes from Lake Mary, Orlando Sanford International Airport, major roadways, shopping, dining, and recreation. Enjoy community amenities including a sparkling pool, cabana, and tot lot. **JOIN US Saturday 9/12/26 10:00am-12:00pm for our GRAND OPENING!** Opportunities are limited—ask about current incentives and schedule your visit today. *Photos are of a similar home and may vary.

3727 Triple Crown Loop, Sanford
$462,990
4 Beds ⋅ 3 Baths ⋅ Kentucky Square SubDv. ⋅ 32773 Zip Code
Virtually Staged. Pre-Construction. To be built. **MAIN LEVEL LIVING!** The Seaton II B on Lot 14 at 3960 Triple Crown Loop offers thoughtful single-story living with open-concept gathering spaces, a designer kitchen, Bed 4/Bath 3, and an extended LANAI ideal for relaxing or entertaining. Experience the lifestyle of Kentucky Square in desirable Sanford, just minutes from Lake Mary, Orlando Sanford International Airport, major roadways, shopping, dining, and recreation. Enjoy community amenities including a sparkling pool, cabana, and tot lot—perfect for connecting, unwinding, and enjoying Florida living. ***JOIN US Saturday 9/12/26 10:00am-12:00pm for our GRAND OPENING!*** Opportunities are limited—ask about current incentives and schedule your visit today. *Photos are of a similar home and may vary from actual home.

3960 Triple Crown Loop, Sanford
$456,385
4 Beds ⋅ 2 Baths ⋅ Kentucky Square SubDv. ⋅ 32773 Zip Code
Virtually Staged. Pre-Construction. To be built. ***MAIN LEVEL LIVING!*** The Juniper C on Lot 5 at 3924 Triple Crown Loop offers thoughtful single-level design with open-concept living, a designer kitchen, inviting gathering spaces, lanai, and a private primary suite designed for comfort, convenience, and everyday ease. Experience the lifestyle of Kentucky Square in desirable Sanford, just minutes from Lake Mary, Orlando Sanford International Airport, major roadways, shopping, dining, and recreation. Enjoy community amenities including a sparkling pool, cabana, and tot lot—perfect for relaxing, connecting, and enjoying Florida living. Join us Saturday 9/12/26 10:00am-12:00pm for our **GRAND OPENING!** Opportunities are limited—ask about current incentives and schedule your visit today. *Photos are of a similar home and may vary from actual home.

3924 Triple Crown Loop, Sanford
$516,385
5 Beds ⋅ 4 Baths ⋅ Kentucky Square SubDv. ⋅ 32773 Zip Code
Virtually Staged. Pre-Construction. To be built. ***The Chester D*** on Lot 8 at 3936 Triple Crown Loop offers spacious two-story living with an open-concept main level, designer kitchen, MAIN LEVEL GUEST SUITE, LOFT, generous gathering spaces, covered lanai, and a private primary suite designed for comfort and everyday convenience. Experience the lifestyle of Kentucky Square, a new community in a highly desirable location near Lake Mary, Sanford, major roadways, shopping, dining, and everyday conveniences. Enjoy community amenities including a sparkling pool, cabana, and kiddy play yard—perfect for relaxing, connecting, and enjoying Florida living. Join us Saturday 9/23/26 10:00am-12:00pm for our ***GRAND OPENING!***Opportunities are limited—ask about current incentives and schedule your visit today. *Photos are of a similar home and may vary from actual home.

3936 Triple Crown Loop, Sanford
$417,990
3 Beds ⋅ 2 Baths ⋅ Kentucky Square SubDv. ⋅ 32773 Zip Code
Virtually Staged. Pre-Construction. To be built. **GRAND OPENING!** Discover the Portland G at Kentucky Square on Lot 118, located at 3975 Triple Crown Loop. This thoughtfully designed single-level home features an inviting covered entry, open-concept living, a kitchen island, two secondary bedrooms, and a private primary suite with dual vanities, walk-in closet, and standing shower. Built for the way you live, the Portland G offers an easy Florida lifestyle with a relaxing lanai and connected spaces for everyday living and entertaining. Kentucky Square’s unique appeal brings thoughtfully designed homes, generous homesites, and everyday convenience together in desirable Seminole County near Lake Mary, Downtown Lake Mary, Orlando Sanford International Airport, SR 417, I-4, SR 46, Lake Jessup, and Lake Monroe. Enjoy community amenities including a sparkling pool, cabana, and kiddy play yard. Don’t wait—ask about current incentives and schedule your visit today! *Photos are from a similar home. Join us Saturday 9/12/26 10:00am-12:00pm for our ***GRAND OPENING!***

3975 Triple Crown Loop, Sanford
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