Kentucky Square Homes under $500,000

Kentucky Square Homes under $500,000

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

Kentucky Square features an array of well-designed homes, many of which are attractively priced under $500,000. This affordability does not compromise quality; the homes boast modern amenities, spacious layouts, and inviting outdoor spaces, perfect for enjoying the beautiful Florida weather. Whether you’re seeking a cozy three-bedroom family home or a stylish two-bedroom retreat, Kentucky Square has something for everyone.

Living in Kentucky Square means embracing a vibrant lifestyle. Residents can enjoy nearby parks, recreational facilities, and a host of shopping and dining options just minutes away. The historic downtown Sanford area is a short drive or leisurely bike ride away, where you can explore local boutiques, savor delicious cuisine, and experience the lively arts scene.

Families will appreciate the excellent schools in the area, providing quality education for children of all ages. Additionally, the community is conveniently located near major highways, making commuting to Orlando and other surrounding areas a breeze.

Discover the charm and affordability of Kentucky Square, where your dream home awaits. Experience the perfect balance of comfort, community, and convenience in this inviting Sanford neighborhood. Don’t miss out on the opportunity to make Kentucky Square your new home!

Newest Kentucky Square Homes under $500,000

3656 Triple Crown Loop, Sanford
$401,990
3 Beds ⋅ 2 Baths ⋅ Kentucky Square SubDv. ⋅ 32773 Zip Code
Virtually Staged. Under Construction. **DECEMBER DELIVERY! 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 ⋅ Kentucky Square SubDv. ⋅ 32773 Zip Code
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.

3659 Triple Crown Loop, Sanford
3888 Triple Crown Loop, Sanford
$479,990
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
3660 Triple Crown Loop, Sanford
$471,990
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
3960 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
3924 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
3975 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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