Kentucky Square Homes with Shingle Roof

Kentucky Square Homes with Shingle Roof

Welcome to Kentucky Square, a delightful subdivision nestled in the heart of Sanford, Florida, within the vibrant Seminole County. This charming community offers a perfect blend of comfort, convenience, and a touch of Southern hospitality, making it an ideal place to call home.

Kentucky Square features a variety of beautifully designed homes, each adorned with classic shingle roofs that not only enhance their curb appeal but also provide durability and protection from the elements. These homes are thoughtfully crafted to cater to diverse lifestyles, whether you're a first-time homebuyer, a growing family, or looking to downsize. The spacious layouts and modern amenities ensure that every resident can find their perfect sanctuary.

One of the standout features of Kentucky Square is its prime location. Residents enjoy easy access to a plethora of local amenities, including shopping centers, dining options, and recreational facilities. The nearby parks and nature trails offer ample opportunities for outdoor activities, whether it’s a leisurely stroll or a weekend picnic with loved ones. The community is also conveniently located near major highways, making commutes to Orlando and other surrounding areas a breeze.

In Kentucky Square, you’ll find not just a home, but a welcoming community where neighbors become friends. With its picturesque streets and friendly atmosphere, this subdivision is the perfect spot to create lasting memories. Come explore the charm of Kentucky Square, where your dream home awaits!

Newest Kentucky Square Homes with Shingle Roof

3652 Triple Crown Loop, Sanford
$459,990
4 Beds ⋅ 3 Baths ⋅ O6452780 MLS
Virtually Staged. Under Construction. MAIN LEVEL LIVING! Move in before the end of the year! The Seaton II B on Lot 144 at 3952 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 pool, cabana, and tot lot—perfect for connecting, unwinding, and enjoying Florida living. Opportunities are limited—ask about current incentives and schedule your visit today. *Photos are of a similar home and may vary from actual home.

3652 Triple Crown Loop, Sanford
3656 Triple Crown Loop, Sanford
$394,990
3 Beds ⋅ 2 Baths ⋅ O6446923 MLS
Virtually Staged. Under Construction. **MOVE IN READY!**! MAIN LEVEL LIVING, OPEN-CONCEPT DESIGN, KITCHEN ISLAND, WALK-IN CLOSET, LANAI! Discover the Portland G on Lot 145 at Kentucky Square. This thoughtfully designed single-level home features an inviting covered entry, spacious connected living areas, a well-appointed kitchen with a center island, two secondary bedrooms, and a private primary suite with dual vanities, a standing shower, and a generous walk-in closet. Step outside to the lanai and enjoy effortless indoor-outdoor living—perfect for quiet mornings, casual gatherings, and the Florida lifestyle. Located in desirable Sanford, Kentucky Square offers convenient access to Lake Mary, Orlando Sanford International Airport, SR 417, I-4, shopping, dining, recreation, and everyday essentials. Community amenities include a sparkling pool, cabana, and kiddy play yard, creating inviting spaces to relax, connect, and play. December opportunities are limited—schedule your visit today and ask about CURRENT INCENTIVES! *Photos are of a similar home and may vary from the actual home.

3656 Triple Crown Loop, Sanford
3659 Triple Crown Loop, Sanford
$450,000
4 Beds ⋅ 2 Baths ⋅ O6445824 MLS
Under Construction. Picture mornings in a bright, open living space, evenings gathered on your covered lanai, and future afternoons by the community pool. The Wellington at Kentucky Square offers 4 bedrooms, 2 bathrooms, and 1,819 square feet designed for everyday living and entertaining. The kitchen features stainless steel appliances, quartz countertops, a tile backsplash, and 42-inch frost cabinets. Tall ceilings and 6-by-36-inch tile flooring add to the airy feel of the main living areas, while the primary suite offers a spacious walk-in closet and a frameless glass shower. At Kentucky Square, the community pool and cabana are coming soon. Explore the Sanford Riverwalk about 6 miles away, enjoy downtown waterfront dining, or spend the day in nearby Lake Mary. The community also features a playground and smart home conveniences and is located within the A-rated Seminole County school district. Sanford International Airport is minutes away, with access to major roads connecting you to Orlando and the East Coast beaches. *Exterior image is an artist’s rendering for illustrative purposes. Landscaping is included with the home; however, actual plant colors, sizes, varieties, and placement may vary slightly from those depicted.

3659 Triple Crown Loop, Sanford
3895 Triple Crown Loop, Sanford
$568,990
5 Beds ⋅ 4 Baths ⋅ O6442534 MLS
Under Construction. Discover spacious, flexible living in the Monroe, a beautifully designed five-bedroom, three-and-a-half-bath home offering approximately 2,900 square feet. Situated on a desirable corner homesite near the community pool, this open-concept home features a formal living room, a spacious family room, and a covered lanai ideal for relaxing or entertaining. The thoughtfully designed kitchen showcases premium appliances, 42-inch cabinetry with crown molding, and elegant quartz countertops. A private first-floor guest suite with its own full bathroom and walk-in closet creates a comfortable retreat for overnight visitors. Upstairs, the spacious primary suite joins three additional bedrooms and a versatile loft, providing plenty of room for work, play, or relaxation. Every full bathroom includes dual sinks for added everyday convenience. Located in Kentucky Square, this home offers access to a community pool, cabana, playground, smart-home features, and A-rated Seminole County schools. Enjoy being just six miles from the Sanford Riverwalk, 13 minutes from Lake Mary-area amenities, and close to Downtown Sanford’s waterfront dining, breweries, and recreation. With Sanford International Airport only minutes away, Downtown Orlando approximately 30 minutes south, and convenient access to major roadways leading to Central Florida attractions and East Coast beaches, Kentucky Square keeps you close to what matters most. *Exterior image is an artist’s rendering for illustrative purposes. Landscaping is included with the home; however, actual plant colors, sizes, varieties, and placement may vary slightly from those depicted.

3895 Triple Crown Loop, Sanford
3884 Triple Crown Loop, Sanford
$554,990
4 Beds ⋅ 4 Baths ⋅ O6442399 MLS
Under Construction. Discover the Magnolia at Kentucky Square, a beautifully designed 2,557-square-foot home offering four bedrooms, three-and-a-half bathrooms, and a two-car garage. The gourmet kitchen features 42-inch cabinets with crown molding and beautiful finishes, while luxury vinyl plank flooring adds style and durability throughout the home. A private first-floor guest suite with a full bathroom creates a comfortable retreat for visitors. Upstairs, a versatile loft joins two secondary bedrooms, a full bathroom with dual sinks, and the spacious primary suite, complete with a large walk-in closet and spa-inspired bathroom. Enjoy outdoor living on the generous covered lanai and a homesite conveniently located near the community pool, cabana, and playground. Located in Sanford, Kentucky Square offers smart-home convenience and easy access to major roadways connecting residents to Downtown Orlando and Florida’s East Coast beaches. Enjoy proximity to A-rated Seminole County schools, Lake Mary area amenities, Sanford International Airport, and the Sanford Riverwalk along Lake Monroe. Downtown Sanford’s waterfront dining, breweries, parks, and recreation are also just minutes away. *Exterior image is an artist’s rendering for illustrative purposes. Landscaping is included with the home; however, actual plant colors, sizes, varieties, and placement may vary slightly from those depicted.

3884 Triple Crown Loop, Sanford
3888 Triple Crown Loop, Sanford
$477,990
4 Beds ⋅ 2 Baths ⋅ O6441715 MLS
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. *Exterior image is an artist’s rendering for illustrative purposes. Landscaping is included with the home; however, actual plant colors, sizes, varieties, and placement may vary slightly from those depicted.

3888 Triple Crown Loop, Sanford
3660 Triple Crown Loop, Sanford
$469,990
4 Beds ⋅ 3 Baths ⋅ O6438779 MLS
Virtually Staged. Pre-Construction. To be built. ***MOVE IN READY!***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
3727 Triple Crown Loop, Sanford
$501,490
5 Beds ⋅ 4 Baths ⋅ O6438748 MLS
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
3960 Triple Crown Loop, Sanford
$462,990
4 Beds ⋅ 3 Baths ⋅ O6438678 MLS
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
3924 Triple Crown Loop, Sanford
$456,385
4 Beds ⋅ 2 Baths ⋅ O6438630 MLS
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
3936 Triple Crown Loop, Sanford
$516,385
5 Beds ⋅ 4 Baths ⋅ O6438587 MLS
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.!***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
3975 Triple Crown Loop, Sanford
$424,490
3 Beds ⋅ 2 Baths ⋅ O6438343 MLS
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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