Kentucky Square Real Estate

Kentucky Square Real Estate

Welcome to Kentucky Square, an inviting subdivision nestled in the heart of Sanford, Florida, within beautiful Seminole County. This charming community is perfect for those seeking a tranquil suburban lifestyle while still enjoying the conveniences of city living.

Kentucky Square boasts a variety of well-designed homes that cater to diverse tastes and needs, from cozy single-family residences to spacious family-friendly layouts. With tree-lined streets and meticulously maintained lawns, the neighborhood exudes warmth and charm, making it an ideal place to call home.

Residents of Kentucky Square enjoy a plethora of local amenities just minutes away. The vibrant downtown Sanford area offers a delightful mix of boutique shops, delicious restaurants, and scenic waterfront parks along the St. Johns River. For outdoor enthusiasts, the nearby Lake Monroe and the scenic trails of the Black Bear Wilderness Area provide ample opportunities for hiking, boating, and enjoying Florida's natural beauty.

Families will appreciate the community’s proximity to excellent schools, recreational facilities, and family-friendly events that foster a strong sense of community. With easy access to major highways, commuting to nearby cities such as Orlando is a breeze, making Kentucky Square a convenient choice for professionals and families alike.

In Kentucky Square, you’ll find not just a house, but a place where memories are made and cherished. Discover the charm, community spirit, and vibrant lifestyle that await you in this delightful Sanford subdivision. Come experience the warmth of Kentucky Square – your dream home is just around the corner!

Newest Listings in Kentucky Square

5 Beds ⋅ 4 Baths ⋅ Kentucky Square SubDv.

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.

3895 Triple Crown Loop, Sanford

3 Beds ⋅ 2 Baths ⋅ Kentucky Square SubDv.

Under Construction. Experience the perfect blend of style, flexibility, and everyday comfort in this Meadowood home at Kentucky Square. This beautifully designed home offers 3 bedrooms, 2 bathrooms, a private office, a separate study space, and 2,090 square feet of thoughtfully planned living space. At the heart of the home, the deluxe kitchen showcases quartz countertops and 42-inch cabinetry with crown molding, opening effortlessly to the spacious living and dining areas. Luxury vinyl plank flooring flows throughout the main living spaces, creating a polished and inviting atmosphere. The spacious primary suite provides a relaxing retreat with a large walk-in closet and spa-inspired bathroom, while quartz countertops add an elevated finish to both bathrooms. Two secondary bedrooms are connected by a dedicated study area, perfect for homework, hobbies, or staying organized, and the secondary bathroom features convenient dual sinks. Step outside to enjoy the covered lanai or take advantage of the nearby community pool, cabana, and playground. Located within an A-rated Seminole County school district, Kentucky Square is just 13 minutes from Lake Mary area amenities and 6 miles from the Sanford Riverwalk, with convenient access to Sanford International Airport, Downtown Orlando, major roadways, and Florida’s East Coast beaches.

3896 Triple Crown Loop, Sanford

4 Beds ⋅ 4 Baths ⋅ Kentucky Square SubDv.

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.

3884 Triple Crown Loop, Sanford

4 Beds ⋅ 2 Baths ⋅ Kentucky Square SubDv.

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

4 Beds ⋅ 3 Baths ⋅ Kentucky Square SubDv.

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

5 Beds ⋅ 4 Baths ⋅ Kentucky Square SubDv.

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

4 Beds ⋅ 3 Baths ⋅ Kentucky Square SubDv.

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

4 Beds ⋅ 2 Baths ⋅ Kentucky Square SubDv.

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

5 Beds ⋅ 4 Baths ⋅ Kentucky Square SubDv.

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

3 Beds ⋅ 2 Baths ⋅ Kentucky Square SubDv.

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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