Highlands Real Estate

Highlands Real Estate

Welcome to Highlands, a picturesque subdivision nestled in the heart of Florida, where the sun shines bright and the community spirit thrives. This charming neighborhood offers a perfect blend of tranquility and convenience, making it an ideal place for families, retirees, and anyone in between.

Highlands is renowned for its lush landscapes, featuring beautifully manicured lawns and vibrant gardens that create a serene atmosphere. The subdivision boasts a variety of well-designed homes, each offering unique architectural styles that cater to diverse tastes. Whether you’re looking for a cozy single-family home or a spacious property to accommodate your growing family, Highlands has something for everyone.

Residents of Highlands enjoy a wealth of amenities that enhance their lifestyle. Take leisurely strolls along the tree-lined streets or enjoy a day at one of the nearby parks, perfect for picnics, playdates, or simply soaking up the Florida sun. For those who love outdoor activities, the subdivision is conveniently located near several golf courses, hiking trails, and recreational facilities.

Highlands is also strategically positioned close to major highways, providing easy access to shopping, dining, and entertainment. With a variety of local boutiques, restaurants, and cafes just a short drive away, residents can indulge in the vibrant culture that Florida has to offer.

In Highlands, community matters. Neighbors become friends, and local events foster a sense of belonging. With its welcoming atmosphere and prime location, Highlands is not just a place to live; it’s a place to thrive. Come discover the charm of Highlands and envision your new life in this delightful subdivision!

Newest Listings in Highlands

$155,000
2 Beds ⋅ 2 Baths ⋅ Highlands SubDv.
You will not want to miss this beautifully appointed 2 bedroom/2 bath end-unit Highlands condo with expansive golf course views. Every room has been updated and it comes TURNKEY, so you can move right in and start enjoying all the community amenities. This unit is set up great for entertaining featuring an open living area with triple sliders out to the screened lanai, open dining area AND breakfast bar, nice sized guest room with full bath that has been updated with granite, tile & cabinetry. The kitchen has been updated with stunning quartzite tops, wood cabinetry, pantry cabinet, and stainless steel appliances. The master suite features a full bath with new quartz tops, beautiful tiled shower, dual sinks and TWO reach-in closets. The condo is light, bright and open with living and dining space, carport w/storage closet, NEW ROOF in 2023,...all this and it is just steps to the inviting community pool and has fantastic views of #13 of the Loch Ness golf course. Don't miss this opportunity to own in one of Ft. Myers finest low-density Country Club communities with 36 holes of championship golf, practice facility, two putting greens, clubhouse with fine dining, lighted Har-Tru tennis courts, heated community pool & spa with cabana offering full food and bar service, staffed fitness center, dog park, pickleball & bocce ball courts, very active social calendar. Fiddlesticks is located close to shopping, restaurants, schools, I-75, airport, ball parks and a short drive to the beautiful white sandy beaches. Mandatory $115,000 membership fee due at closing. No CDD fees. Own your own golf cart. NO WAIT LIST HERE.

15091 Bagpipe Way Unit 101, Fort Myers
$799,000
3 Beds ⋅ 3 Baths ⋅ Highlands SubDv.
Welcome to your private Florida retreat! Situated on a tranquil, 1.3-acre agricultural lot at the end of a quiet dead-end street, this modern 3-bedroom, 3-bathroom sanctuary offers the perfect blend of rural freedom, with no HOA or CDD fees, and ultimate convenience. Surrounded by mature shade trees and sitting high at 80 feet above sea level (no flood insurance required!), this estate features nearly 3,000 sq. ft. of air-conditioned living space and over 5,000 sq. ft. total under cover, including the garage, screen-enclosed pool with expansive lanai, and a dedicated custom catio. Designed for low-cost, energy-efficient, and worry-free living, the home comes equipped with 40 solar panels (slashing electric bills to near zero), a whole-home generator with a 250-gallon propane tank, a roof under 2 years old, fresh exterior paint, dual-zone HVAC systems, and a full-property irrigation system fed by abundant local spring water. Security is complete with an ADT system, while outdoor enthusiasts will love the fully fenced backyard for pets, an area already cleared for a chicken coop, and the beginnings of a cozy backyard fire pit amidst nature visits from local owls, hawks, and hummingbirds. Under 10 minutes to daily shopping; 1.4 miles to Tampa General Hospital Spring Hill and 3.1 miles to Planet Fitness. Endless top-tier local restaurants within a 15-minute drive. 15 minutes to historic Brooksville, 30 minutes to Tampa International Airport (TPA) & downtown Tampa, and under 45 minutes to virtually everything the Suncoast has to offer.

16547 Crossandra Lane, Spring Hl
$265,000
3 Beds ⋅ 2 Baths ⋅ Highlands SubDv.
Great starter home in Dade City! This well-designed 3 bedroom, 2 bath residence offers approximately 1,370 square feet of living space with an open floor plan, comfortable living areas, and a practical layout that makes everyday living easy. Built in 2015, the home features block and stucco construction, a shingle roof, central HVAC, ceramic tile and luxury vinyl plank flooring, and an attached 2 car garage. The kitchen offers wood cabinetry, in kitchen dining, and essential appliances, while the primary suite includes a private bath with a large dual sink vanity. Situated on approximately 0.15 acres in Highland Bluff, the property provides an excellent opportunity for a buyer looking for an affordable Dade City home with room to make it their own. A smart opportunity for a first time buyer or anyone seeking a management home in a well established neighborhood.

37154 Highland Bluff Circle, Dade City
$281,000
3 Beds ⋅ 2 Baths ⋅ Highlands SubDv.
Country Living on Nearly 4 Acres in Spring Hill! Looking for space, privacy, and endless possibilities? Welcome to 16036 Bosley Drive, a rare opportunity to own approximately 3.85 acres of Agricultural Residential (AR) land in the heart of Spring Hill. This charming 3-bedroom, 2-bath manufactured home offers 1,056 square feet of comfortable living space and features a beautifully updated kitchen, spacious living areas, and a desirable split-bedroom layout. The primary suite includes its own private bathroom and walk-in closet for added comfort and convenience. Step outside and enjoy the freedom that comes with nearly four acres of usable land. Whether you dream of keeping animals, creating a garden, storing your recreational vehicles, building a workshop, or simply enjoying the peace and privacy of country living, this property provides the space to make it happen. With Agricultural Residential zoning, you'll enjoy flexibility rarely found on properties this close to everyday conveniences. Located just minutes from shopping, dining, schools, and major roadways, you'll have the best of both worlds: a rural lifestyle with easy access to everything you need. Properties with acreage in Spring Hill are becoming harder to find. Don't miss this opportunity to create your own private retreat and enjoy the freedom of country living.

16036 Bosley Drive, Spring Hl
$485,000
3 Beds ⋅ 2 Baths ⋅ Highlands SubDv.
MOVE-IN-READY ACREAGE WITH NO HOA OR CDD! Seller will contribute $5,000 toward the buyer’s closing costs and/or interest-rate buydown. Escape the restrictions and crowded lots of subdivision living without sacrificing modern finishes or everyday convenience. This completely renovated 3-bedroom, 2-bath block home offers more than 2,000 square feet of living space on 1.92 private, flat, and usable acres. Inside, the open-concept design features a bright kitchen with quartz countertops, generous gathering spaces, and beautifully updated bathrooms with tiled showers. Crown molding, tray ceilings, and marble tile flooring add style throughout, while built-in speakers, smart light switches, and a security system provide modern convenience. Relax or entertain on the large screened porch overlooking the peaceful property. Major improvements per prior seller, all NEW in 2021: Roof, electrical system, septic system, well tank, water heater, and HVAC. A whole-house water softener was installed 2025. Zoned Agricultural-Residential with no HOA or CDD, the property provides the freedom and space to create the lifestyle you have been looking for. Bring your dogs, chickens, up to two horses, RV, boat, trailer, or recreational equipment. Plant a garden, grow your own food, enjoy the existing greenhouse and storage shed, or explore possibilities for future improvements. Enjoy peaceful country living while remaining convenient to shopping, dining, schools, medical facilities, the Suncoast Parkway, Weeki Wachee Springs, Gulf Coast beaches, and Tampa. If you have been searching for an updated home with usable acreage, privacy, and room to enjoy your hobbies, animals and outdoor lifestyle, this property is ready to welcome you home.

16700 Auburndale Lane, Spring Hl
$425,000
3 Beds ⋅ 2 Baths ⋅ Highlands SubDv.
Escape to your own private retreat on 2.36 acres in Spring Hill! Built in 2020, this beautifully maintained home offers the perfect blend of modern comfort, outdoor living, and room to spread out. Step inside to discover an open-concept floor plan featuring elegant tray ceilings, crown molding, and abundant natural light throughout. The spacious kitchen is designed for gathering, complete with a large center island, ample cabinetry, and plenty of prep space for entertaining family and friends. Equipped with a whole house water system and additional kitchen water filtration system! Unwind year-round in the sparkling pool or hot tub, kick back under the covered patio featuring a laid-back beach-inspired atmosphere complete with relaxing hammocks. Enjoy the privacy of your gated entrance with convenient remote and keypad access, and take advantage of multiple storage sheds for tools, equipment, hobbies, or extra storage needs. Bring your RV, boat, or recreational vehicles—this property includes an RV hookup and plenty of room to park and play. Whether you're looking for a peaceful country setting, space for outdoor activities, or a property that can accommodate your toys and hobbies, this home delivers. Enjoy the freedom of acreage living while remaining conveniently located near shopping, dining, schools, and the Suncoast Parkway for an easy commute. Don't miss this rare opportunity to own a move-in ready home with acreage, a pool, RV hookup, secure gated entry, and endless possibilities in Spring Hill!

16947 Auburndale Lane, Spring Hl
$700,000
4 Beds ⋅ 3 Baths ⋅ Highlands SubDv.
Just listed for sale- the 1924 Haynie House is the quintessential Florida Craftsman Bungalow. This beautiful home has 3 bedrooms plus an office and 2 full bathrooms in the main house, a detached 1 bedroom/1 bathroom apartment, a 1 car garage/workshop and sits on one of the largest properties in the Duckpond. Located on the main Boulevard on the duck pond, you will love the gorgeous views of the city-maintained, park-like setting with a meandering creek as it flows into the pond. The Duckpond is an area of 900 homes in the NE Gainesville Residential District. It is walking distance to downtown Gainesville, 2.5 miles to the University of Florida, UF Health/Shands and just 10 minutes to the Gainesville airport. One of the most walkable neighborhoods in Gainesville, it is just blocks to area shops and restaurants as well as Tom Petty and Roper Parks and the Thomas Center and gardens. This beautiful home emphasizes horizontal lines, local fieldstone and building materials and maintains a strong connection to the natural Florida landscape. From the front covered entry you enter the foyer with beautiful red oak wood floors. To the left is the large Great Room with a wood-burning fireplace and French Doors to the backyard. Off the Great Room is a Florida Room with walls of windows, built-in shelves and a Murphy bed to double as a guest room. To the right of the front door is the dining room with views of the creek across the street. Off the dining room is a large pantry and utility room. Beyond the dining room is the updated and beautiful kitchen with solid cypress wood cabinets, quartz countertops, custom tile backsplash and stainless steel appliances including a gas range and microhood. The floors have newer travertine tile. Off the Kitchen is a full bathroom with updated tile, fixtures and lighting throughout. Many updates have been done to the home, including a new roof in 2026, new HVAC in 2023 and new wiring in 2008. The water supply lines are copper and the sewer has been replaced. The crawlspace has a new Dryzone dehumidification system. Upstairs is the Primary Suite with a separate office and walk-in closet. There is an updated Jack-and-Jill Bathroom with new tile, vanity and shower glass enclosure. There are two additional upstairs guest bedrooms. All the upstairs bedrooms have heart pine floors. Some windows have been replaced. The large .26-acre lot spans to the street behind the home as well. Parking can be from the front under the Port Cochere or from the rear driveway and 1 car garage. Above the garage is the detached 1-bedroom/1-bathroom apartment. The open space has a kitchen complete with updated appliances. The bedroom is separate from the living space with large windows on three sides. Downstairs is a separate washer and dryer as well as additional storage space. The garage has automatic doors on both sides. Just off the garage is a detached, separate laundry room for the main house with a ton of additional storage. The large, fenced rear yard includes a paver patio perfect for grilling. The outdoor fireplace takes center stage for entertaining family and friends. This is a rare, updated home with a great location.

720 Ne Boulevard, Gainesville
$750,000
3 Beds ⋅ 2 Baths ⋅ Highlands SubDv.
One or more photo(s) has been virtually staged. Welcome to the historic Thomas House and Gardens, a concrete block home built in 1934 and nestled within Gainesville's beloved Duckpond Historic District. From the moment you arrive, you'll be captivated by the timeless charm of original hardwood floors, crystal doorknobs, abundant natural light, and a stunning marble fireplace that serves as the heart of the home. Thoughtfully updated for today's lifestyle, the spacious kitchen features stone countertops, extensive cabinetry, a generous pantry, and modern conveniences without taking away from the home's historic character. The bright sunroom, complete with terracotta tile floors, provides the perfect space for reading, working, or simply enjoying views of the gardens. Beyond the interior, this over half-acre property (a rarity in the Duckpond) unfolds into a series of enchanting outdoor spaces. A private courtyard offers a peaceful retreat for morning coffee or evening gatherings, while winding garden paths lead through an English garden filled with blooming azaleas, jasmine, camellias, ferns, and agapanthus. Peak around one corner to find a charming teak gazebo with bench swings. Another turn invites you to go back to the days of lawn games and garden parties. Enjoy the gentle flurry of activity of cardinals, blue jays, and woodpeckers, in a setting that feels worlds away from the city while remaining just a 10 minute walk to downtown Gainesville with its restaurants, Hippodrome Theatre and booming nightlife. The Thomas House seamlessly blends historic elegance with modern comfort. Significant updates include a stunning chef’s kitchen, a newer roof (2022), and updated bathrooms. The Thomas House is more than a home, it's an opportunity to become the next steward of a remarkable piece of Gainesville history. Rich in character and architectural detail, this exceptional property offers the rare combination of historic significance, modern updates, and expansive outdoor living spaces in one of the city's most treasured neighborhoods. 4 Point Inspection Report available upon request

717 Ne Boulevard, Gainesville
$500,000
4 Beds ⋅ 3 Baths ⋅ Highlands SubDv.
Virtually Staged. Welcome home to this beautiful 4-bedroom, 2.5-bathroom, 2-car garage home located in the highly desirable Highlands community—with no HOA or CDD fees. Situated on just over an acre of land, this property offers the perfect blend of space, privacy, and functionality. As you approach, you’ll be greeted by a gated entrance and lush, mature trees that create a peaceful and inviting setting. The fully fenced yard provides both privacy and room to enjoy the outdoors, while the property also features a detached 2-car garage with a workbench, along with two additional storage sheds—ideal for hobbies, tools, or extra storage. Step inside to discover a bright and airy interior with high ceilings and abundant natural light. The home offers a thoughtful layout, including a formal living room, a dedicated dining room, and a spacious bonus room complete with a convenient half bathroom—perfect for entertaining guests or creating a flexible living space. The kitchen is generously sized and well-equipped with a full appliance package, ample cabinetry, and plenty of counter space. Enjoy casual meals at the breakfast nook, sip your morning coffee or tea, or gather around the additional bar-top seating for effortless entertaining. The primary suite is conveniently located on the first floor and features a large walk-in closet and a private ensuite bathroom with dual vanities and a spacious walk-in shower. Upstairs, you’ll find the secondary bedrooms, offering comfort and privacy for family or guests. Just off the kitchen and primary bedroom, step out onto the screened-in back porch—an ideal spot to relax, unwind, and take in the natural surroundings. Conveniently located near the Veterans Expressway, Hwy. 41, Hwy. 52, and Hwy. 19, this home offers easy access to shopping, dining, and commuting routes while still providing a serene, private setting. Don’t miss your opportunity to own this exceptional property—schedule your private showing today!

18731 Firethorn Drive, Spring Hl
$749,900
5 Beds ⋅ 3 Baths ⋅ Highlands SubDv.
Exceptional opportunity to own a beautiful and versatile property in the peaceful countryside of Venus, Highlands County, FL, featuring over 16 acres of land ideal for agricultural use, expansion, or building your dream estate. This unique property offers a total of 2,026 sq ft of living space, including a main block home (3 bedrooms, 2 bathrooms) and a separate mobile home (2 bedrooms, 1 bathroom) — perfect for multi-generational living, guest accommodations, or potential rental income. In total, the property features 5 bedrooms and 3 bathrooms. The main house has been extensively upgraded, including a new shingle roof with skylight (2023, with permits), stainless steel kitchen appliances (2022), tankless water heater (2021), and fresh exterior paint (2023). The home also features a dual gated entrance ready for automatic openers, offering privacy and convenience. Designed for outdoor living and functionality, the property includes an exterior kitchen and bathroom, a pump with Kinetico water system, and a reverse osmosis system (2024). Water is available throughout all animal areas, making it ideal for livestock, along with a sprinkler system for trees and landscaping. The mobile home has also been updated and is move-in ready, featuring a new water pump and pressure tank (2024), new outlets and switches (2025), recessed ceiling lighting (2025), AC system and ductwork (2019), tankless water heater (2019), electric stove (2019), and refrigerator (2021). Surrounded by nature and located in a quiet, private area, this property offers the perfect blend of comfort, functionality, and endless potential. Whether you’re looking for a family compound, agricultural investment, or a serene retreat, this property is a rare find in Highlands County.

615 Graham Dairy Rd, Venus
$575,000
3 Beds ⋅ 2 Baths ⋅ Highlands SubDv.
If you’ve been searching for space, privacy, and the ability to live more intentionally — without giving up modern luxury — this custom-built 2024 home on 1.1 fully fenced acres delivers. Built by Cobra Custom Builder, this 3-bedroom, 2-bath residence offers 2,622 sq ft of thoughtfully designed living space in Spring Hill’s AR1 agricultural zoning district, blending rural freedom with contemporary comfort — and no HOA. Inside, soaring 10-foot ceilings and professional-grade luxury vinyl plank flooring set the tone. The open-concept layout flows seamlessly into a chef-inspired kitchen featuring Diamond soft-close cabinetry, custom organizers, granite countertops, an oversized island with seating, organized cabinet pantry storage, and smart Wi-Fi connected appliances — all conveying. The private primary suite is thoughtfully designed with its own dedicated A/C zone for personalized comfort and includes a versatile bonus room ideal for a sitting area, reading retreat, extended walk-in closet, nursery, office, or dressing lounge. An additional shoe closet enhances storage and flexibility, allowing the space to adapt to your lifestyle needs. The primary bath features a large walk-in shower with double rain shower fixtures, creating a true retreat experience. Smart-home features include electric shades throughout, smart thermostats, security system, exterior cameras, and number-code entry. Additional highlights include a finished 2-car garage (552 sq ft), expansive concrete driveway and patio areas, well and septic system. Step outside and experience what truly sets this property apart. The fully fenced backyard combines relaxation and self-sufficiency with a conveying heated Spool, a 12x24 storage shed with reinforced flooring, irrigation shed, and a fully developed homestead farm representing approximately $25,000 in infrastructure. Enjoy a 75-ft grape trellis, 8 metal raised beds, 20 wood raised beds, cinder block potato bed, hot house trellis, grow trellis, two compost areas, 7-zone irrigation system, and an extensive collection of established fruit trees and berry bushes. Located approximately 4 miles from the Suncoast Parkway, 1.5 miles from Tampa General Hospital – Spring Hill, and about 45 minutes to Tampa and Tampa International Airport, this property offers peaceful acreage living in Florida with everyday conveniences just a short drive away.

16090 Fringe Tree Drive, Spring Hl
$399,900
3 Beds ⋅ 2 Baths ⋅ Highlands SubDv.
Upgraded & Truly Move-In Ready, This Exceptional Home Stands Apart from Any New or Resale Property in Its Neighborhood or Price Range! Nothing But High-End Improvements Were made to This Home for Focus on Comfort Health, Energy Efficient, Safety & Modern Design! This Home Features 3 Bedroom 2 Bathrooms, Premium Trane Xv17 Variable Speed Heat Pump System with Smart Thermostat, Delivering Whisper-Quiet Operation, Superior Humidity Control, Outstanding Energy Control. All Windows Have Been Replaced with Fiberglass Triple-Pane Low-E Casement. A Custom Modern Fiberglass Door with a Triple Locking System & Heavy-Duty Triple Pane Sliding Glass Door Enhance Both Security & Style! The Heart of The Home Is Truly the Professionally Designed Custom Kitchen Showcasing Kraft Maid Flat-Panel Cabinetry with Dove-Tail Construction, New Quartz Countertops with Full Height Backsplash, Designer Lighting, And Under Cabinet Lighting with Adjustable Color Temperature. Bosch 800 Series Black Stainless-Steel Appliances Include an Induction Range & Convection Microwave, Complemented by an Exterior-Vented Range Hood, Deep Composite Sink, And Quiet Insulated Disposal. The Living Spaces Are Warm & Inviting with Recessed Lighting Added Throughout the Home, Including Upgraded Designed Fixtures in Key Areas. The Primary Suite Includes an Expansive Custom Closet System for Exceptional Storage & Organization. Outdoor Living Is Elevated with Screened in Saltwater pool Featuring a Pebble-Coated Interior, Led Lighting, New Pump & Filter, And Recently Updated Screening. The Covered Lanai Includes New Oversized Fan & Recessed Lighting, Creating A Perfect Space for Entertaining or Relaxing. The Garage Is the Standout Feature of This Home. Finished As Fully Conditioned & Functional Extension of the Home. It Includes Poly-Urea Coated Floor, Insulated Garage Door, Rock Wool Insulation, Recessed Lighting, Custom Garage Cabinetry, Additional 20-Amp Circuits, & Bosch Variable Speed Mini Split Ac System. The Attic Offers Floored Storage, Secured Walk Planks, And Extensive Lighting for Easy Access. Additional Highlights for This Exceptional Home Include a New Commercial Grade Water Heater, Architectural Privacy Fence, And A 50 Amp Generator Input Capable of Powering the Entire Home (Or Easily Converted to A Level 2 Ev Charger). Smart Home Features That Include Smart Switches, Remote Ac Control, Smart Garage Door System with Delivery Capability & Ring Door Camera. This Is a Rare Opportunity to Own a Thoughtfully Upgraded Home Where Quality, Efficiency, And Modern Convenience Have Been Prioritized at Every Level.

404 Country View Circle, Deland
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