Highland Park Real Estate

Highland Park Real Estate

Welcome to Highland Park, a picturesque subdivision nestled in the heart of Florida, where charm meets convenience. This vibrant community is a hidden gem, offering residents a perfect blend of suburban tranquility and proximity to urban amenities. Highland Park is characterized by its beautifully landscaped streets, friendly neighbors, and a strong sense of community spirit.

As you stroll through the neighborhood, you’ll be greeted by an array of stunning homes, each exuding unique architectural styles and warm curb appeal. From modern designs to classic Floridian aesthetics, there’s something for everyone in Highland Park. The thoughtfully planned layout features spacious lots, allowing for plenty of outdoor living space, perfect for family gatherings or quiet evenings under the stars.

One of the standout features of Highland Park is its commitment to outdoor recreation. Residents enjoy access to well-maintained parks, walking trails, and playgrounds, making it an ideal setting for families and active individuals alike. The community also hosts various events throughout the year, fostering connections among neighbors and creating lasting memories.

Highland Park is conveniently located near major highways, providing easy access to the vibrant cities of Orlando and Tampa. Whether you’re looking for shopping, dining, or entertainment, you’ll find it all just a short drive away. Additionally, top-rated schools and essential services are within reach, ensuring a seamless living experience for families.

In Highland Park, you’re not just buying a home; you’re investing in a lifestyle filled with community, comfort, and endless opportunities. Discover your future in this enchanting Florida subdivision today!

Newest Listings in Highland Park

$325,000
Highland Park SubDv. ⋅ 33770 Zip Code
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, Largo
$325,000
4 Beds ⋅ 2 Baths ⋅ Highland Park SubDv. ⋅ 33770 Zip Code
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, Largo
$349,000
2 Beds ⋅ 2 Baths ⋅ Highland Park SubDv. ⋅ 33770 Zip Code
Centrally located duplex with long term tenants. No flood zone insurance required. Each side is 1 bed 1 bath.

905 Beverly Avenue, Largo
$253,900
3 Beds ⋅ 2 Baths ⋅ Highland Park SubDv. ⋅ 33770 Zip Code
ATTENTION ALL CONTRACTORS, FLIPPERS, & INVESTORS! THIS IS THE PROPERTY YOU ARE LOOKING FOR. THIS IS A CASH ONLY DEAL. 3 BEDROOM 1 BATH HOUSE UP FRONT WITH A SEPRATE MOTHER-IN-LAW COTTAGE IN THE BACK. BOTH SIT ON ONE PARCEL. HOUSE & MOTHER-IN-LAW COTTAGE HAVE THEIR OWN ELECTRIC AND WATER METERS. ALL UTILITIES ARE PASSED THROUGH TO THE TENANTS. PARTIAL UPGRADES TO THE HOUSE, NO UPGRADES TO THE COTTAGE. HOUSE HAD NEW SHINGLE ROOF INSTALLED (9/24/24), HOUSE WAS TENTED FOR TERMITES IN MAY 2026. VACATED BOTH TENANTS TO SELL THE PROPERTY. THIS SITE HAS TREMENDOUS CASH FLOW POTENTIAL. LAST (2) LEASES PRODUCED $2495 GROSS MONTHLY. PROPERTY SITS ACROSS THE STREET FROM LUXURY APPARTMENTS AND WITHIN A BLOCK FROM THE PINELALS COUNTY TRAIL& ENTRANCE TO BELLAIR. LIVE IN THE HOUSE AND RENTT THE COTTAGE TO OFFSET YOUR MONTHLY LIVING EXPENSES. A TRUE DIAMOND FOR THE INVESTOR LOOKING FOR MONTHLY INCOME OR VERY AFFORDABLE LIVING BY HAVING MONTHLY IMCOME FOR THE LIVE-IN-OWNER. IF YOU ARE LOOKING FOR THE RENOVATION PROJECT THIS SITE HAS MUCH POTENTIAL.

1010 Rosery Road Nw, Largo
$539,800
3 Beds ⋅ 2 Baths ⋅ Highland Park SubDv. ⋅ 33770 Zip Code
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, Largo
$749,000
3 Beds ⋅ 2 Baths ⋅ Highland Park SubDv. ⋅ 34239 Zip Code
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, Sarasota
$259,000
2 Beds ⋅ 1 Baths ⋅ Highland Park SubDv. ⋅ 33770 Zip Code
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, Largo
$1,725,000
7 Beds ⋅ 6 Baths ⋅ Highland Park SubDv. ⋅ 33770 Zip Code
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, Largo
$429,000
3 Beds ⋅ 2 Baths ⋅ Highland Park SubDv. ⋅ 33770 Zip Code
Fantastic development opportunity! Due to a recent zoning change, this double lot can now accommodate UP TO FOUR DWELLING UNITS! The City of Largo has confirmed that permissible configurations include a quadplex, two duplexes, or four single-unit cottages, subject to applicable development standards. The property currently consists of two structures: a fully renovated single-family home plus a separate two-story accessory structure. The accessory structure features a garage/workshop on the first floor, with an unfinished upper level that can be remodeled for residential use, subject to permitting and current code requirements. The renovated front home is 846 sq. ft. 3BR/2BA, with new flooring, kitchen, appliances, windows and roof, and is move-in ready. Come tour this rare opportunity to create your own multifamily investment property in Largo!

1006 15th Avenue Nw, Largo
$159,500
2 Beds ⋅ 1 Baths ⋅ Highland Park SubDv. ⋅ 32117 Zip Code
Priced below appraised value and ready for new owners! This charming 2-bedroom, 1-bath Daytona Beach home is a great opportunity for first-time buyers, downsizers, or investors looking for a move-in-ready property with plenty of updates already completed. Major improvements include a newer roof (2021), updated windows, plumbing, and well pump. Inside, you'll find a remodeled kitchen featuring shaker-style cabinetry, and an updated bathroom. The indoor laundry area adds extra convenience, and the washer and dryer are included. Enjoy your morning coffee on the welcoming front porch or unwind on the private rear porch. This home offers a great combination of comfort and value. Whether you're looking for your first home, a low-maintenance place to downsize, or your next investment property, this one is worth a look! Information recorded in MLS is intended to be accurate but cannot be guaranteed. Everything should be independently verified.

1636 Valencia Avenue, Daytona Beach
$145,000
3 Beds ⋅ 1 Baths ⋅ Highland Park SubDv. ⋅ 33844 Zip Code
Calling all investors! This 1930 home offers an excellent opportunity for renovation or rental income. With over 1,400 square feet of living space, this property features 3 bedrooms, 1 bathrooms, and plenty of potential. The classic block home with original character provide a solid foundation for restoration or updates. Located in a revitalized area, this property is perfect for investors looking to capitalize on the neighborhood’s growth. Whether you're planning to flip or hold as a rental, this home has the layout and potential for a great return on investment. Don’t miss this opportunity—schedule a showing today! Seller will create a package deal and included lots 1 & 2 for a purchase price of $250,000.

1813 Robinson Drive, Haines City
$294,400
Highland Park SubDv. ⋅ 34251 Zip Code
This property is 1.43 acres. According to Sarasota County Building & Zoning, based on the Plat of Record, 1 to 5 residential homes can be built on this property. Zoned for horses. It is near Lakewood Ranch close to the corner of HWY 70 and Verna Rd. Development in the area is happening at a rapid pace. This property along with the surrounding properties are ripe for development with their close proximity to HWY 70.

Verna Road, Sarasota
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