Highland Park Homes with Sidewalk Exterior Features

Highland Park Homes with Sidewalk Exterior Features

Welcome to Highland Park, an enchanting subdivision nestled in the heart of Florida, where southern charm meets modern living. This vibrant community is renowned for its picturesque streets lined with beautiful homes, each boasting delightful sidewalk exterior features that invite leisurely strolls and foster a strong sense of community.

Highland Park offers a variety of homes that cater to diverse lifestyles, from cozy single-family residences to spacious family homes, all designed with comfort and style in mind. The sidewalks winding through the neighborhood are perfect for morning jogs, evening walks, or simply enjoying the fresh Florida air while chatting with friendly neighbors. Children can be seen riding their bikes, while families gather for weekend barbecues in their front yards, creating a warm and inviting atmosphere that feels like home.

The subdivision is conveniently located near top-rated schools, lush parks, and local shopping centers, making it an ideal place for families and professionals alike. Residents can easily access major highways, ensuring a quick commute to nearby cities and attractions.

In Highland Park, you’ll find more than just a house; you’ll discover a community where neighbors become friends and every day feels like a retreat. With its charming sidewalks and vibrant community spirit, Highland Park is not just a place to live, but a place to thrive. Come experience the magic of Highland Park, where your dream home awaits!

Newest Highland Park Homes with Sidewalk Exterior Features

$266,900
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
$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
$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
$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, 2 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
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