Kentucky Square Homes for Sale

Kentucky Square Homes for Sale

Welcome to Kentucky Square, a delightful subdivision nestled in the heart of Sanford, Florida, within the scenic Seminole County. This charming community offers a perfect blend of suburban tranquility and convenient access to urban amenities, making it an ideal choice for families, retirees, and professionals alike.

Kentucky Square boasts a variety of homes for sale, each with its own unique character and appeal. From cozy single-family residences to more spacious options, there’s something to suit every lifestyle and budget. Many of these homes feature modern designs, open floor plans, and beautiful outdoor spaces, perfect for enjoying Florida's sunny climate.

Residents of Kentucky Square enjoy a strong sense of community, with friendly neighbors and well-maintained common areas that enhance the neighborhood's charm. The subdivision is conveniently located near top-rated schools, parks, and recreational facilities, making it easy for families to enjoy the great outdoors and engage in community activities.

For those who appreciate a vibrant lifestyle, Kentucky Square is just a short drive away from Sanford's historic downtown area, where you can explore an array of shops, restaurants, and cultural attractions. With easy access to major highways, commuting to nearby cities like Orlando is a breeze.

Whether you’re searching for your first home, looking to downsize, or seeking an investment opportunity, Kentucky Square offers a welcoming environment and a range of homes for sale that cater to your needs. Experience the charm and convenience of Kentucky Square—your dream home awaits!

Newest Kentucky Square Homes for Sale

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.

3895 Triple Crown Loop, Sanford

3 Beds ⋅ 2 Baths ⋅ O6442502 MLS

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 ⋅ 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.

3884 Triple Crown Loop, Sanford

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.

3888 Triple Crown Loop, Sanford

4 Beds ⋅ 3 Baths ⋅ O6438779 MLS

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 ⋅ 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

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

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

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

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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Donna M. Rose, Owner - Broker in Charge - Lic. Realtor

Precision, Expertise and Results I am the key to your new home!! Say YES to a change of address!!! The Legal Edge: I am not your typical Realtor. With a legal background and a paralegal degree specializing in Real Estate and Family Law, I bring a level of precision to the table that is rare in this industry. Having spent years as a Real Estate Closer for a major local title company, I understand the "moving parts" of a transaction from the inside out. I don't just navigate deals; I anticipate hurdles before they arise. Award-Winning Service: Customer service isn't just a buzzword for me—it is my reputation. In 2006, I was honored with a prestigious customer service award nominated by my own peers. That award still sits on my desk today as a daily reminder of the standard I set for myself. When you work with me, you aren't just another file on my desk; my goal is to make you feel like my only client. Why Work With Me? As one of the most respected Realtors in the county with a consistent 5-star rating across major real estate platforms such as Zillow, Realtor.com and HomeLight, etc, I offer a RESULTS NOT GIMMICKS approach. * Negotiation with Precision: My legal training ensures your interests are protected at every turn. * Seamless Closings: I keep all parties on point and focused to ensure a successful, stress-free closing. * Total Dedication: Every client receives 100% of my effort from the first meeting to the final signature. Choosing the right Realtor is more than finding someone to open doors; its about finding a partner who can navigate the complexities of a legal contract and ensure a seamless closing. Call me, message me or text me. Let's get to work. 386-334-2264 donna@drpropertiesnow.com 130 Sycamore Sunshine Lane New Smyrna Beach, FL @donnaismyrealtor #donnaismyrealtor

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Stefani Turco, Broker Associate, Lic. Realtor

Turning Dreams into Addresses: Helping You Find Your Perfect Slice of Florida Paradise As a proud Florida resident for over 50 years, I’m not just invested in real estate—I’m deeply committed to this community, both professionally and personally. Married for over 23 years with four amazing children, and a lover of horses and German Shepherds, I’m passionate about helping families and investors find their perfect slice of paradise here in this beautiful state. Being a Broker Associate isn’t just about closing deals for me; it’s about turning dreams into reality. Whether you’re looking for a dream home, a vacation getaway, or a smart investment, I’m here to guide you through every step of the process with care, expertise, and a genuine commitment to your goals. In addition to being a Real Estate Broker Associate, I’m also a business owner and someone with a solid understanding of construction. This well-rounded background allows me to provide valuable insights into a property’s potential, helping you make informed decisions. My business experience has also sharpened my negotiation skills, ensuring that you get the best possible outcome—whether you’re buying or selling. With integrity, attention to detail, and a true heart for service, my goal is to make your real estate journey seamless, stress-free, and rewarding. Let’s work together to turn your vision into reality and help you find the Florida paradise you’ve always dreamed of! 130 Sycamore Sunshine Lane, New Smyrna Beach, FL 32168 386.316.7303 stefani@drpropertiesnow.com

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Jayce A. Rose, Lic. Realtor

Meet Jayce Rose - A Legacy of Excellence in Real Estate Real estate is about more than property; it's about people and the community we build together. For Jayce, real estate isn't just a career path, it’s a straightforward calling. It's literally in his blood, as the son of the founder of DR Properties, Jayce was raised in the heart of the industry. He was by his mother’s side, assisting with preparing and activating new listings, attending open houses, mastering the nuances of client communication, and observing his mother successfully navigate complex real estate transactions with grace and expertise. This early immersion provided him with a "boots-on-the-ground" education that few can match, instilling in him the core values that define his practice today. A Legacy of Excellence and a Foundation of Trust: From a young age, Jayce was more than just an observer; he was a fixture in the industry. Acting as a dedicated assistant to his mother on countless occasions, he gained an "over-the-shoulder" education that no classroom could provide. This experience instilled in him a high level of discipline, teamwork, and the competitive drive necessary to succeed in today’s fast-paced real estate market. This hands-on upbringing allowed him to witness the intricacies of the market, the art of the deal, and the importance of client relationships long before he ever held a license. Jayce understands that a successful real estate transaction is built on more than just paperwork; it’s built on trust and transparency. His years of experience have taught him the vital importance of proactive communication and expert negotiations. While using a sharp, articulate approach to advocate for his clients with an independent spirit and a relentless work ethic. he has earned a stellar reputation as a professional who is honest, trustworthy, reliable, and deeply rooted in the local community. Academic Excellence & Professional Dedication: After earning his Bachelor’s degree in Business from Daytona State College, Jayce is able to bring a strategic and well balanced edge to the team. He is able to combine his formal business education with a modern approach to a classic industry. The Tech-Forward Edge: In today’s fast-paced market, Jayce brings a vital, fresh look to the industry. He has an expert grasp of technology and social media. He knows exactly how to leverage these platforms to give properties the maximum exposure and connect with the modern buyer. Why Work With Jayce? Jayce is the "Modern Day Professional". Now, having officially passed his real estate exam, he is ready to step onto the front lines. He combines his formal business education with real-world experience to offer his clients a distinct advantage Beyond his professional credentials, Jayce is recognized by friends, colleagues and neighbors as an all-around great human being. His kindness and smart, empathetic nature makes him not just a capable Realtor, but a trusted partner in your next real estate journey.

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Dylan B. Rose, Lic. Realtor

Meet Dylan B. Rose - The Next Generation of Real Estate I believe that a successful closing is built on a foundation of honesty and data. My goal is to ensure every client feels empowered and educated at every turn. A lifelong resident with deep roots in the community, Dylan doesn’t just work in real estate, she was raised in it. For Dylan, real estate isn't just a career, its a natural progression. As the daughter of the founder of DR Properties, Dylan’s education in the industry began at the kitchen table and on-site at properties. Having served as a dedicated assistant within the family business from a young age, she developed an intuitive understanding of the market that few can match. Dylan spent her youth assisting her mother, gaining a "behind-the-scenes" education in the industry long before earning her professional credentials. A Foundation of Excellence: Dylan’s journey is backed by both experience and education. After years of hands-on training in the family business, she earned her degree from Daytona State College, blending traditional industry wisdom with a modern, academic perspective. Dylan enters the family legacy with a bold, fresh vision. She bridges the gap between traditional real estate values and the high-tech demands of today’s market. The Tech-Forward Edge: In today’s fast-paced market, Dylan brings a vital, fresh look to the industry. Recognized as a digital powerhouse in social media and technology, with a massive following across YouTube, Instagram, and Snapchat, she possesses the unique ability to turn digital engagement into real-world results. She understands that in the modern era, a property’s online presence is just as important as its curb appeal, and she uses her tech-savvy skill set to ensure her clients’ listings stand out in a crowded digital landscape. She is a true digital native with an expert grasp of technology and social media. This isn't just a hobby - ii’s a powerful marketing tool. She knows exactly how to leverage these platforms to give properties maximum exposure and connect with the modern buyer. When you work with Dylan, you aren't just getting a Realtor; you are gaining a tech-forward powerhouse who is committed to excellence, driven to succeed, and backed by a lifetime of industry expertise. She has been preparing for this role her entire life.

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Carter Brackett, Lic. Realtor

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Andrea Marlot, Lic. Realtor

As a transplant from MN, I’ve been a New Smyrna resident for only 5 years, but I was a devoted annual visitor for 25 years before relocating. I’m very acquainted with Volusia County. I’ve been a licensed Realtor since 2015 and love guiding people on their journey to homeownership. In addition to being a Realtor, I also work for an exterior home remodeling company, specifically dealing with storm related insurance claims. My knowledge of the claims industry has been very beneficial to buyers, sellers and home inspectors when issues arise during a home inspection. I have a keen eye for spotting potential damage, and I know how to seamlessly navigate the muddy waters of the claims process. Whether you’re looking to buy, sell or rent, I would love the opportunity to support your ambition!

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Susan Logan, Lic. Realtor

I have been a New Smyrna Beach resident for over 35 years and am very familiar with the area. I would love to work with you, family, or friends for all of your real estate needs.

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Marianne Breitenbruck, Event Assistant

Recently becoming a full time resident in the beautiful sunshine state, I have always believed and now I know for sure, LIFE IS BETTER AT THE BEACH!!! Come on down, the water is great. The only salt we use here is to rim the top of our margarita glass.

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