Highland Park Real Estate

Welcome to Highland Park, a picturesque subdivision nestled in the heart of Florida, where serene living meets vibrant community spirit. This charming neighborhood is designed for those seeking a perfect blend of tranquility and convenience, making it an ideal place to call home.

Highland Park boasts a variety of beautifully crafted homes that cater to diverse lifestyles, from cozy family residences to modern townhouses. Each property is thoughtfully designed with quality finishes and spacious layouts, ensuring comfort and style. The lush landscaping and tree-lined streets create an inviting atmosphere, perfect for evening strolls and neighborhood gatherings.

One of the highlights of Highland Park is its close-knit community. Residents enjoy a range of amenities, including well-maintained parks, walking trails, and playgrounds, all designed to encourage outdoor activities and foster connections among neighbors. The community hosts regular events, from seasonal festivals to weekly farmers' markets, providing ample opportunities to engage with fellow residents and celebrate the joys of suburban living.

Convenience is at your doorstep in Highland Park, with easy access to shopping, dining, and entertainment options. Nearby schools are highly rated, making it a great location for families. Plus, the proximity to major highways ensures that you are just a short drive away from the beautiful beaches and vibrant culture of Florida's coastal cities.

Discover the charm of Highland Park, where a welcoming community and a beautiful environment come together to create the perfect setting for your next chapter. Come explore this enchanting subdivision and envision your future in this delightful corner of Florida!

Newest Listings in Highland Park

$320,000

2 Beds ⋅ 2 Baths ⋅ TB8547589 MLS

Welcome home to this charming 2-bedroom, 2-bath home in the desirable Archwood-South Haven area of Largo! Offering a spacious split-bedroom floor plan, this home provides plenty of privacy with the primary bedroom and en-suite bath on one side and the guest bedroom and second bath on the other. A versatile bonus room adds even more living space and is perfect for a home office, den, playroom, or reading room. The home also offers an attached one-car garage for added convenience. Major updates include a roof replaced in 2018 and a water heater installed in 2021. Best of all, the property is located outside of a designated flood zone. This is a great opportunity for a first-time homebuyer looking for a place to call their own! Conveniently located near shopping, dining, parks, beautiful Gulf beaches, and everything Largo and the surrounding area have to offer. Come see all this home has to offer!

520 14th Avenue Nw, Belleair Bluffs

Listing courtesy of LUXURY & BEACH REALTY INC. 727-800-5906

$174,000

3 Beds ⋅ 2 Baths ⋅ V4950626 MLS

Virtually Staged. You will step inside to an open concept living - dining area featuring a decorative fireplace. The adjacent eat-in kitchen provides white shaker cabinets, granite countertops and a breakfast nook, plus the inside laundry room is nearby. Down the hall, you'll find three bedrooms and two bathrooms, offering comfortable space for whatever fits your lifestyle. There is also a deep one-car offering parking and room for storage and a covered back porch. Bring this 1,356 sq. ft. concrete block home back to life with some vision and elbow grease. This home was updated several years ago and is ready for a new owner to unlock its full potential again. Situated on .24 acres, the location is hard to beat! Conveniently situated just off the LPGA corridor, you'll be close to schools, public transportation, shopping at the outlets and The Towne Center, as well as major highways for an easy commute. Space, convenience, and opportunity--all in one package for under $175K. Whether you're looking for your next investment or a property you can make your home, this one is worth a closer look. Owner occupants using financing may qualify the the $100 down financing program. Ask how! Schedule your private showing today and discover the possibilities! Buyer pays doc stamps and utility connection fees required for inspections. Sold AS-IS. No warranties expressed or implied. All measurements are approximate. Owner-occupant bids are given priority during the exclusive listing period. For bidding information and property details we are here to help, or you can visit the HUDHomeStore case # 094-926064.

1102 Old Kings Road, Daytona Beach

Listing courtesy of CALNAN REAL ESTATE. 386-675-1137

$279,900

4 Beds ⋅ 2 Baths ⋅ O6438517 MLS

Welcome to 1481 Derbyshire Rd — Where Charm, Space & Possibility Come Together! Step inside this beautifully updated, Staged to Perfection, and move-in-ready home where timeless charm meets modern comfort! Situated on a spacious corner lot, this inviting 4-bedroom, 2-bath residence offers something truly special — a versatile fifth room currently designed as an office, but ready to become whatever your lifestyle calls for. Imagine a playroom, home gym, library, creative studio, media room, or your own private retreat. The possibilities are endless! From the moment you arrive, the gorgeous wraparound front porch sets the tone. Picture yourself enjoying your morning coffee as the day begins or unwinding in the evening breeze — this is the kind of outdoor space that makes a house feel like home. Enter through the welcoming foyer and discover a spacious living room to the right, offering plenty of room to gather with family and friends or entertain guests. Continue into the heart of the home, where the abundant kitchen and dining area create an inviting hub for everyday living and memorable gatherings. The kitchen offers abundant cabinet storage, beautiful countertops, and generous workspace, with plenty of room to customize it even further with an island, additional shelving, or the coffee bar you've always dreamed of! Throughout the home, you'll find generously sized rooms offering comfort and flexibility. The owner's suite is a true standout, featuring its own private sunroom — a premium bonus space that could become your morning coffee retreat, reading nook, home office, or peaceful escape at the end of the day. Enjoy a 2020 Roof and AC as well! And the location? It's hard to beat! Enjoy convenient access to the Halifax River, Daytona Beach's world-famous beaches, Tanger Outlets, Robert Strickland Park, Daytona International Speedway, Daytona Lagoon Waterpark & Arcade, Volusia Mall, plus an abundance of shopping, dining, medical facilities, parks, and entertainment. Whether you're searching for a primary residence, vacation getaway, or investment opportunity, 1481 Derbyshire Rd delivers the space, flexibility, charm, and location you've been looking for. Come see all the possibilities this special home has to offer — your next chapter starts here!

1481 Derbyshire Road, Daytona Beach

Listing courtesy of THE NAVY HOUSE. 321-438-1318

$325,000

TB8542120 MLS

Rare Multi-Structure Investment: 2 Detached Homes on 1 Parcel in Historic Largo Redevelopment District. Position your portfolio in one of Pinellas County’s key redevelopment zones. This unique dual-dwelling property features two independent Old Florida detached homes on a single lot, delivering built-in diversification, immediate cash-flow potential, and multiple execution strategies: dual rental income, house-hacking/live-in investment, or long-term value-add play. Property Highlights & Key Capital Improvements: Primary Residence (1001 15th Ave NW): Well maintained by a long-term owner; features a brand-new central A/C system (2022), sturdy metal roof, and attached covered carport. Classic pine flooring throughout. Secondary Cottage (1455 10th St NW): Proven rental history, fixer upper, with strong value-add potential. Fully detached with its own driveway access and covered carport. Shared Utility Outbuilding: Centralized communal barn-shed equipped with full washer/dryer hookups and auxiliary storage to serve both units. Low Risk Exposure: Located in FEMA Flood Zone X (no mandatory flood insurance required). Location & Infrastructure: Situated just 1 mile from the West Bay Drive urban corridor, minutes to downtown Largo redevelopment projects, and 2.5 miles to the Gulf Coast beaches. Investment Flexibility: Whether you're executing a buy-and-hold strategy, maximizing gross yield via distinct leases, or building equity in a growing coastal submarket, this turn-key layout minimizes overhead while offering clear upside. Check it out today!

1455 10th Street Nw, Belleair Bluffs

Listing courtesy of DONOVAN HOME SALES INC. 800-822-1222

$240,000

2 Beds ⋅ 1 Baths ⋅ 2161517 MLS

All-Brick, move-in-ready, and packed with character--this 2 bedroom, 1 bath home makes smart use of its charming 1,002 sq ft where it counts. Even better, the home received a Brand-New Roof in July. Natural light fills every room, highlighting original oak hardwood floors. A stone fireplace graces the living room. A formal dining room adds dedicated space for entertaining, while the bonus flex room--with its rich wood-paneled ceiling--offers a stylish setting for a home office, creative space, or whatever fits your lifestyle. The kitchen features oak cabinetry and granite countertops, while the recently renovated bathroom adds a distinctive touch with gorgeous wood ceiling paneling. Kitchen leads to a covered breezeway connecting the home to the detached one-car garage, complete with a washer and dryer. Outside, the large corner lot offers a mix of sunny and shaded spaces, plus a serene and spacious fenced backyard with plenty of room to spread out and make it your own. A hidden side-yard retreat adds even more outdoor potential, featuring a shaded paved patio with built-in table and a vintage outdoor barbecue - all surrounded by natural greenery and dappled shade giving it an almost secret-garden feel. Conveniently located near Riverside, Avondale, NAS, and Downtown, you're also just a short ride from local cafés, restaurants, boutique shopping, and Boone Park. Classic brick construction, flexible spaces, a new roof, and a location that keeps you connected--this one is ready for its next chapter to unfold.

1522 Murray Drive, Jacksonville

Courtesy of FLORIDA HOMES REALTY & MTG LLC

Listing courtesy of FLORIDA HOMES REALTY & MTG LLC.

Listing courtesy of KATHALEEN CAISSE from FLORIDA HOMES REALTY & MTG LLC.

$325,000

4 Beds ⋅ 2 Baths ⋅ TB8540892 MLS

Two for the price of one! Two Florida Classic quaint Old Florida Homes on the same lot! 1001 15th Ave. NW and 1455 10th St. NW. The larger main home at 1001 15th Ave. NW. was lived in by the owner for many years and lovingly maintained. The smaller "income rental house" at 1455 10th St. was rented out and has much potential. Both homes have sturdy, convenient carports. In between the two homes is a communal barn- shed housing washer & dryer, plus storage. Pick up this package and rent out both or live in one and rent the other! Both have long-lasting metal roofs. The main house at 1001 has a newer central A.C system installed in 2022. Conveniently located in non-flood zone X near all kinds of restaurants and shopping and from Clearwater/Largo Rd it's just 1 mile to West Bay Drive, 2.5 miles to the beach!

1455 10th Street Nw, Belleair Bluffs

Listing courtesy of DONOVAN HOME SALES INC. 800-822-1222

$344,900

2 Beds ⋅ 2 Baths ⋅ TB8540127 MLS

Investment opportunity located in central Largo is this duplex with long term tenants eager to stay. 1 is section 8 with opportunity to increase monthly income. Separately metered with each tenant paying all utilities. No flood zone insurance required. Each side is 1 bed 1 bath.

905 Beverly Avenue, Belleair Bluffs

Listing courtesy of BEST BEACH RENTALS & SALES PA. 727-827-7112

$519,900

3 Beds ⋅ 2 Baths ⋅ TB8527914 MLS

New Construction in Largo! Welcome to 1117 15th Ave NW — a stunning brand-new 3-bedroom, 2-bathroom home offering 1,760 sq ft of thoughtfully designed living space, just minutes from the Gulf beaches. Located in Flood Zone X and sitting at 52 feet above sea level, this home offers added peace of mind in a desirable, elevated location. Step inside to an open-concept floor plan featuring 10-foot-high ceilings and abundant natural light, creating an airy, spacious feel throughout. The kitchen is designed to impress, showcasing upgraded cabinetry, premium countertops, and modern finishes that flow seamlessly into the living and dining areas—perfect for entertaining or everyday living. The split-bedroom layout provides privacy for the owner's suite, complete with a luxurious en-suite bathroom and an oversized walk-in closet large enough to double as a dressing room. Additional highlights include a 2-car garage, brand-new systems and appliances, and quality craftsmanship throughout. Enjoy direct access to the Pinellas Trail right outside your door, perfect for biking, walking, or jogging. You'll also be just minutes from Largo Central Park, the boutique shops and restaurants of Belleair Bluffs and Clearwater, with the beautiful Gulf beaches only a short drive away. Don't miss the opportunity to own a beautifully crafted new construction home, schedule your showing today!!

1117 15th Avenue Nw, Belleair Bluffs

Listing courtesy of CHARLES RUTENBERG REALTY INC. 866-580-6402

$329,000

3 Beds ⋅ 2 Baths ⋅ TB8524897 MLS

**Exceptional Value with Incredible Potential!** Welcome to 900 Beverly Ave in Largo, a 3-bedroom, 2-bath fully furnished pool home offering 1,333 square feet of living space in a highly desirable location just minutes from the Gulf beaches while situated in preferred **Flood Zone X**, helping reduce flood insurance concerns. Inside, you'll find brand-new luxury vinyl plank flooring throughout and a functional layout highlighted by a spacious primary suite featuring a walk-in closet, private en-suite bath, and sliding glass doors leading to the backyard. The kitchen also opens to the rear deck, creating an excellent foundation for future indoor-outdoor entertaining. The rear yard offers incredible potential and already features a large deck surrounding the pool along with a detached workshop with electricity—perfect for a workshop, hobby space, home gym, studio, or additional storage. Located in Largo where short-term rentals are permitted with no minimum rental period, this property has previously operated successfully as an Airbnb, making it an attractive opportunity for both investors and owner-occupants seeking additional income potential. The home is also being sold fully furnished, with all existing furnishings conveying with the sale, making it even easier to begin enjoying or renting the property immediately. The home is priced to reflect the roof, which is believed to require repair or replacement, presenting an outstanding opportunity for buyers to customize the home while building immediate equity. With only minor cosmetic improvements, this home has tremendous upside. Whether you're looking for a primary residence, vacation home, or investment opportunity, this is a rare chance to purchase a pool home with a detached workshop, short-term rental flexibility, and significant upside in one of Largo's most convenient locations.

900 Beverly Avenue, Belleair Bluffs

Listing courtesy of EXP REALTY LLC. 888-883-8509

$749,000

3 Beds ⋅ 2 Baths ⋅ A4695132 MLS

Welcome to a refined corner-lot home directly across from Arlington Park — one of Sarasota's most beloved neighborhood amenities. With 1,955 sqft of thoughtful living space, three bedrooms with walk-in closets, two updated baths, and a true 2-car garage, this property offers a combination that simply doesn't exist at this price point in the heart of the city. Every detail has been considered for Florida living. A 2022 metal roof with a 50-year warranty, two new Trane HVAC systems, impact-resistant windows, and a new water heater mean lower insurance, lower utilities, and no deferred maintenance. Located in evacuation Zone E and high and dry through every recent storm season, this is the rare home that lets you stop worrying about Florida ownership. Inside, character meets quality: stained solid wood doors, crown molding, hardwood bamboo flooring, a maple stairwell, and warm wooden ceilings. Walk out to a generous screened lanai, private hot tub, and lush tropical landscaping framed by palms, bamboo, and fruit trees. The fully fenced yard provides quiet privacy in a setting most Sarasota buyers only dream about. Step out your front door to Arlington Park's 50-meter lap pool, tennis courts, basketball courts, dog park, and walking trails. Sarasota Memorial Hospital, Southside Village dining, and downtown are all within minutes. Beaches at Siesta Key are a short drive away. Zoned for top-rated Southside Elementary (A-rated). A rare opportunity: turnkey, insurable, and irreplaceable location — directly across from the park.

2690 Temple Street, Central Sarasota

Listing courtesy of MICHAEL SAUNDERS & COMPANY. 941-907-9595

$259,000

2 Beds ⋅ 1 Baths ⋅ TB8487879 MLS

Charming 1925 bungalow with high ceilings -- Roof (2018), stainless steel appliances, granite countertops, 48" upper kitchen cabinets, and original hardwood floors -- on of the only 1920's Bungalows left in the area. This home offers excellent walkability with the 47-mile Pinellas Trail biking/walking trail just at the end of the block, at the other end of the block is Jam's Produce, a Greek restaurant and more! Featuring high ceilings, built-ins, and large windows bringing in an abundance of natural light, this rare 1925 Bungalow can be an excellent investment for an Airbnb, long-term tenant or mid-term tenant with several hospitals in proximity. The property is just a short bike ride or car ride from Largo Central Park, more shops, retail, and a new mixed-use development. Less than a mile from TJ Maxx, LA Fitness, Ross, and other shopping + dining options. Situated in a non-flood zone and just a 7-minute drive to sugar sand beaches. HVAC 2018 *Huge back deck but half of it needs work*

1010 14th Avenue Nw, Belleair Bluffs

Listing courtesy of JAY ALAN REAL ESTATE. 855-529-2526

$1,725,000

7 Beds ⋅ 6 Baths ⋅ A4682296 MLS

Price Improvement! This rare 5-unit short-term rental property offers an exceptional opportunity to own a fully established Airbnb-style compound just a short drive to the Gulf beaches and a central hub for nature trails, festivals, and events in downtown Clearwater. ** Listing includes includes Parcel Id 27-29-15-38970-003-0050. Spread across three lots on two parcels, the property includes a spacious main residence along with four individual guest cottages, creating multiple income-producing retreats in one highly desirable Pinellas County location. The property consists of five total units, including four well-appointed 1-bedroom, 1-bath cottages, each approximately 576 square feet, ideal for couples or small families seeking a private Florida getaway. The larger main home spans approximately 1,148 square feet and serves as the centerpiece of the compound with 3 bedrooms and 2 baths, luxury finishes, LVP flooring, a true primary suite with a walk-in closet, a bunk room, and inviting outdoor living spaces. Guests enjoy a side patio for dining plus a screened back porch complete with darts and foosball, creating a resort-style experience. Three of the four cottages share nearly identical layouts for ease of operation and consistent guest appeal, while all units offer generous backyard areas, ample secure parking, and convenient Yale smart lock access. Offered fully furnished and professionally designed, this property is truly turnkey and has been well maintained, while still presenting additional upside, including the potential to add a swimming pool. Laundry is thoughtfully arranged with a washer and dryer inside the main house, plus an additional centrally located utility room with washer and dryer access for cottage guests or cleaning teams. Each unit is separately metered for electric and water, providing added flexibility for future ownership strategies and long-term operational value. Adding to the uniqueness of the offering is the street-to-street frontage between 15th Avenue Northwest and 16th Avenue Northwest, along with mixed-use zoning that may provide future redevelopment or expansion potential as the surrounding area continues to grow. Surrounded by tropical landscaping with palm and orange trees, and located minutes from Clearwater, Belleair, and Indian Rocks Beach, yet positioned in Airbnb-friendly Largo, this is a truly rare chance to operate a well-performing short-term rental compound in one of Florida’s most in-demand coastal markets.

1500 Clearwater Largo Road N, Belleair Bluffs

Listing courtesy of WILLIAM RAVEIS REAL ESTATE. 941-894-1255

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