Hillsborough Homes with Cottage Architectural style

Hillsborough Homes with Cottage Architectural style

Welcome to Hillsborough County, Florida, a vibrant community that perfectly blends urban sophistication with the charm of suburban living. Nestled along the Gulf Coast, Hillsborough is renowned for its lush landscapes, picturesque parks, and an array of cultural and recreational activities. From the bustling streets of Tampa to the serene shores of the Bay, this county offers an ideal backdrop for families, professionals, and retirees alike.

One of the most delightful architectural styles you’ll find in Hillsborough is the enchanting cottage style. These homes exude warmth and character, often featuring quaint details such as gabled roofs, inviting porches, and charming gardens. Cottage-style homes are perfect for those who appreciate a cozy, intimate atmosphere, showcasing an aesthetic that harkens back to simpler times while still providing modern comforts.

In Hillsborough, cottages come in various sizes and layouts, catering to diverse lifestyles. Whether you’re looking for a charming two-bedroom retreat or a spacious family cottage, you’ll find a variety of options that embody the spirit of Florida living. Many of these homes are nestled in friendly neighborhoods, where community bonds are strong, and local amenities are just a stone’s throw away.

With its rich history, vibrant arts scene, and a wealth of outdoor activities, Hillsborough County is not just a place to live; it’s a place to thrive. Embrace the charm of cottage living in this beautiful corner of Florida, where every day feels like a vacation and home is truly where the heart is.

Newest Hillsborough Homes with Cottage Architectural style

$769,999
3 Beds ⋅ 2 Baths ⋅ Excelsior Sub SubDv. ⋅ 33603 Zip Code
Welcome to an almost-new Key West–style cottage in the heart of historic Tampa Heights—where timeless charm, modern comfort, and one of Tampa’s most vibrant urban lifestyles come together beautifully. Just moments from Armature Works, the Tampa Riverwalk, neighborhood parks, and nearby public and private schools, this home places you right in the center of everything buyers love about Tampa Heights. Downtown Tampa, Channelside, Water Street, and Ybor City are all less than 10 minutes away, while Tampa International Airport is approximately 20 minutes from your door. From the moment you arrive, the home makes a memorable first impression with its inviting oversized front porch and distinctive arched entry door. Step inside and you’ll immediately notice the craftsmanship, thoughtful design, and attention to detail that make this residence feel truly special. Designed with beauty, efficiency, and everyday comfort in mind, this 3-bedroom, 2-bath home offers an open great room that is ideal for entertaining, relaxing, or gathering at the end of the day. Outside, enjoy Florida evenings around the gas backyard fire bowl, bike along the Riverwalk, or stroll to dinner at Armature Works and take in sunset views over the Hillsborough River. Custom built in 2021, this home offers the ease and confidence of newer construction while capturing the character and charm that makes Tampa Heights so desirable. Furnishings are negotiable if desired, creating a potentially exceptional turnkey opportunity in one of Tampa’s most connected and sought-after neighborhoods.

3016 N Massachusetts Avenue, Tampa
$449,900
4 Beds ⋅ 2 Baths ⋅ Hamners Marjory B First Add SubDv. ⋅ 33603 Zip Code
Located in the heart of Tampa, this 4-bedroom, 2-bath home has been completely remodeled and features many upgrades both inside and out. From the white picket fence to the stone-like paver driveway that leads to a peaceful courtyard fountain, this move-in ready home is a peaceful outdoor oasis for relaxing and equipped for entertaining family and friends.. Inside, the beautiful wood floors, and calming, fresh colors provide a peaceful backdrop to get away from the hustle and bustle of the city. An open layout facilitates a space where everyone can be involved in activities and conversations from anywhere. The bright and cheerful kitchen, enhanced by the skylight, is designed to be efficient and comfortable with plenty of storage. All bedrooms are spacious, have large closets, and plenty of room for additional furniture. The fourth bedroom, just off the living room, can also serve as an office or playroom. Exiting the laundry room, you will enter a screened-in porch. This is the perfect place to listen to the birds sing while enjoying a cup of coffee in the morning, read a book on the slider bench in the afternoon, or, in the evening, select a soothing color on the cafe lights, and enjoy a nice glass of wine. Outside the screened patio, you will find a beautifully landscaped, fenced-in back yard oasis. No matter which direction you look, you’ll see that each space is created with purpose. The hot tub under the canopy is a favorite on the cool Florida nights or after a hard day at work. There is a cozy sitting area to spend time with friends, a nearby BBQ, and an al fresco dining area under the giant oak tree. For even more fun, challenge your family and friends to a putting contest on your very own putting green. Day or night, this yard has something for everyone. Mechanically, the home has a new air conditioning system (Jan. 2024), water heater (2023), metal roof (2019), refrigerator, disposal, as well as recent termite treatment, promising years of worry-free ownership. The solar system is four years old and keeps the electric bill to a minimum.

2301 W Idlewild Avenue, Tampa
$390,000
3 Beds ⋅ 2 Baths ⋅ Lesleys SubDv. ⋅ 33603 Zip Code
Rare DUPLEX in the heart of Old Seminole Heights! Whether you're an investor looking to add a strong cash-flowing asset to your portfolio or a savvy house hacker looking to offset your mortgage with rental income, opportunities like this are few and far between. Offering two completely separate residences on one property, this unique investment combines privacy, character, and long-term income potential in one of Tampa's most desirable rental markets. Most recently leased for $1,700 and $1,750 per month, this property offers proven income potential from day one. Unlike a traditional duplex, these are two completely detached homes with no shared walls, giving each residence the feel and privacy of a single-family home. The front 1-bedroom, 1-bath 658sqft main house immediately stands out with its distinctive Cape Cod-inspired cedar shingle exterior—a rare architectural style that adds charm and timeless character. Inside, you'll find fresh interior paint, newer windows, white shaker cabinetry, granite countertops, wood-look laminate flooring, a spacious walk-in closet, in-unit laundry, and a full kitchen appliance package including the refrigerator, range, microwave, and dishwasher. Privately tucked behind the main home is a detached 2-bedroom, 1-bath 680sqft carriage house with its own alley access and off-street parking, creating an ideal setup for long-term tenants, multigenerational living, or an owner-occupant looking to generate passive income. A privacy fence separates the two homes, creating the feel of two independent residences rather than a typical duplex. Each home features its own water, sewer, and electric meters, central heat and air, and private laundry, making ownership and management simple. Major improvements include roofs and water heaters replaced in 2018, HVAC systems installed in 2019 and 2020, termite tenting completed in 2018, and more. Additional storage is conveniently located beneath the carriage house. Located in the heart of highly sought-after Old Seminole Heights, you'll be just minutes from neighborhood favorites including award-winning restaurants, breweries, coffee shops, parks, Downtown Tampa, Armature Works, and the Tampa Riverwalk. Investment opportunities with this level of character, privacy, and flexibility rarely become available in Seminole Heights. Whether you're building long-term wealth through rental income or looking for one of the best house-hacking opportunities on the market, this is a property you'll want to see.

405 E Cayuga Street, Tampa
$499,000
4 Beds ⋅ 2 Baths ⋅ Deanes Percy SubDv. ⋅ 33603 Zip Code
Welcome to this beautifully maintained Riverside Heights home offering exceptional flexibility with a private attached guest apartment. An increasingly rare find less than two miles from Downtown Tampa. Situated on an oversized lot, the property combines comfortable everyday living, modern updates, abundant outdoor space, and the potential for multigenerational living or supplemental rental income. The light-filled main residence features three bedrooms, a fully renovated bathroom and an open, airy floor plan that creates an easy flow between the living and dining areas. Warm wood-look flooring extends throughout the primary living spaces, while a distinctive sliding barn door adds character. The bright kitchen offers crisp white cabinetry with generous storage. With many of the home’s major improvements already completed, this home is move-in ready and prepared for its next chapter. A standout feature is the private guest apartment, thoughtfully designed to function independently from the main home. The suite includes its own designated parking area, private side entrance, a full kitchen, full bathroom, washer and dryer, and a dedicated AC Mini-Split system. Outside, a fenced red-brick courtyard gives the suite its own inviting private outdoor retreat. This versatile space is ideal for extended-stay guests, multigenerational living, a private home office, fitness or recreation studio, or potential short term rentals.* The oversized, fully fenced backyard provides an impressive amount of space for pets, play, gardening or future outdoor enhancements. A large covered patio with a ceiling fan offers a shaded setting for dining, entertaining or relaxing year-round, while mature trees contribute privacy and character. A storage shed provides additional convenience. Located in one of Tampa’s most desirable urban neighborhoods, this Riverside Heights property places you just minutes from Armature Works, Ulele, the Tampa Riverwalk, Water Works Park, several popular restaurants, entertainment and cultural attractions of Downtown Tampa. Whether you are searching for a primary residence with room to grow, a flexible multigenerational layout or a home with potential supplemental-income opportunities, this unique property delivers space, versatility and an outstanding Tampa location. *Buyer should independently verify zoning, permitting, leasing eligibility and any restrictions governing rental or income-producing use.

3913 N Lynn Avenue, Tampa
$464,900
3 Beds ⋅ 2 Baths ⋅ Hanleys Sub SubDv. ⋅ 33603 Zip Code
Historic Charm. Modern Peace of Mind.Experience the timeless character of this beautifully preserved 1920s bungalow, thoughtfully updated to blend classic architectural charm with today’s modern conveniences. The beautifully renovated kitchen features elegant quartz countertops and solid wood cabinetry, creating the perfect balance of vintage character and modern living. Luxury vinyl plank flooring flows throughout the home, complementing its timeless appeal with durability and easy maintenance. Thoughtfully preserved original details—including charming built-in cabinetry and generous linen storage in the main bathroom—celebrate the craftsmanship that makes historic bungalows so beloved.Major capital improvements provide lasting peace of mind, including a new asphalt fiberglass shingle roof (2022), complete drain line and sewer line replacement with whole-home re-piping (2022) by Benjamin Franklin Plumbing, a 150-amp electrical panel upgrade (2020), new ductwork (2020), and a 2.5-ton Bryant heat pump A/C system (2016). The home also features a whole-house 3-stage water filtration system with premium catalytic carbon filtration and a built-in scale inhibitor.Outside, the detached garage offers exceptional flexibility for parking, additional storage, a workshop, or the opportunity to create a future guest house, home office, or income-producing ADU (buyer to verify zoning and permitting).Located in the heart of historic Seminole Heights, this home is just a short walk (approximately 1 mile) from the Hillsborough River and benefits from ongoing Riverwalk expansions that continue to improve connectivity and outdoor recreation throughout the area. Nearby, the major $800 million redevelopment of Robles Park Village is bringing significant new investment, community amenities, and neighborhood improvements—further elevating the long-term value and appeal of this location.With inviting curb appeal and a prime Seminole Heights address, this move-in-ready home offers the rare combination of authentic 1920s charm, thoughtful updates, and lasting peace of mind.

813 E New Orleans Avenue, Tampa
$474,900
3 Beds ⋅ 2 Baths ⋅ Unplatted SubDv. ⋅ 33563 Zip Code
Rare opportunities like this don't come along often! Situated on **1.3 unrestricted acres with NO HOA**, this versatile property offers endless possibilities for homeowners, business owners, investors, and outdoor enthusiasts alike. Whether you're looking for space to park your RV, boat, work trucks, trailers, or recreational toys, this property gives you the freedom that is becoming increasingly difficult to find. A **dedicated RV pad with full hookups (water, electric, and septic)** makes it ideal for guests, extended family, travel enthusiasts, or future income potential. The property features a **large workshop with updated lighting**, multiple storage buildings, and plenty of room to expand your hobbies or operate a home-based business. With the area's continued commercial growth and development nearby, this property presents a unique opportunity for those looking to secure land in an increasingly desirable location while still enjoying the privacy and tranquility of country living. Inside, the home has been thoughtfully updated and is truly move-in ready. Enjoy an inviting wraparound porch, abundant natural light, built-in shelving, an electric fireplace, granite countertops, stainless steel appliances, remodeled bathroom, and brand-new windows with updated blinds throughout. Major improvements provide peace of mind for years to come, including a **new roof (2025), A/C (2022), new well and pump (2026), new drain field**, and numerous additional updates already completed. If you've been searching for acreage without restrictions, room for your business, equipment, RV, or future plans—all while being just minutes from shopping, dining, and everyday conveniences—this is the property you've been waiting for. **Properties with this much flexibility, usable land, and future potential are becoming increasingly rare. Don't miss your chance to own a property that offers not just a home, but an investment in your lifestyle and tomorrow's opportunities.**

3016 N Maryland Avenue, Plant City
$799,999
4 Beds ⋅ 3 Baths ⋅ Hamners Shadowlawn SubDv. ⋅ 33603 Zip Code
Ideally located in the desirable Seminole Heights neighborhood, this beautifully crafted new construction home is just minutes from local favorites like Duff's sports bar and Ebisu Sushi Shack. This custom Craftsman style residence offers 4 bedrooms, 2.5 bathrooms, a dedicated office and den, and an upstairs loft with a thoughtful and functional layout throughout. The open concept kitchen is designed for both everyday living and entertaining, featuring stainless steel appliances, solid surface countertops, custom wood cabinetry, and a large butcher block island overlooking the backyard. Expansive sliding doors lead to a covered rear porch, creating an inviting indoor outdoor living space. The dining area includes a stylish dry bar with shiplap accents for added character. The spacious primary suite includes built in closet storage, a double vanity, and a beautifully finished walk in shower with custom tile work. The backyard offers plenty of space to add a pool, while the oversized driveway and 1 car carport provide ample parking. Mature oak trees enhance the property’s curb appeal, and rear street access offers the potential for a future detached garage with City approval. Built with attention to detail and quality craftsmanship, this home stands out from typical new construction offerings.

920 E Shadowlawn Avenue, Tampa
$299,900
2 Beds ⋅ 2 Baths ⋅ Sun City Center Unit 274 & 2 SubDv. ⋅ 33573 Zip Code
Discover unparalleled golf course living in this exquisite two-bedroom, two-bath home located within the exclusive, gated, 55+, maintenance-free community of Verona at Renaissance. Perfectly positioned on the third hole of the prestigious Club Renaissance Golf Course, this residence effortlessly blends luxury, everyday comfort and breathtaking golf course and pond views. Inside, find gorgeous luxury vinyl plank flooring sweeping throughout the main living spaces, beautifully complemented by an elegant tray ceiling finished with classic crown molding. The stunning designer kitchen boasts crisp white shaker-style cabinetry with undermounted lighting, beautiful stone countertops, a gleaming glass subway tile backsplash and a premium Samsung kitchen appliance package including a brand-new range, dishwasher and garbage disposal. Retreat to the spectacular primary suite, accessible through a grand eight-foot entry door. This private oasis continues the home's architectural elegance with its own tray ceiling and crown molding, as well as even more golf course views through the large window. The spa-inspired primary bath features stone counters, a spacious dual vanity and a sleek frameless glass walk-in shower. Outdoor living is a breeze on the covered lanai, which features charming brick flooring and views of the golf course and pond. For ultimate peace of mind, permanent hurricane screens have been installed on the lanai and all windows, which is an extensive upgrade. Engineered with wind resistance in mind, these screens provide top-tier security during storm season without compromising the home’s stylish aesthetic. Other updates include a new roof installed in December 2024, an innovative in-wall pest control system, pre-plumbing for a future whole-home water softener system and a handy utility sink located in the garage. Even your storage needs are elevated with reinforced attic floors above the garage, an upgraded pull-down ladder for easy access and added attic lighting. Residents of Verona enjoy the exclusivity of a private heated community pool, complemented by membership to the esteemed Club Renaissance. This magnificent 43,000-square-foot facility features a resort-style pool, a comprehensive fitness center with group classes and track, premium spa services and exceptional dining experiences. Furthermore, residents benefit from the extensive amenities of the Sun City Center main campus, which include indoor and outdoor pools, supplementary fitness facilities, a dog park, a library and courts for tennis, pickleball, softball, volleyball and lawn bowling, alongside more than 150 active social clubs. Thoughtfully designed for convenience, the entire community is golf-cart accessible, fostering a connected and vibrant lifestyle.

718 Chipper Drive, Sun City Center
$159,900
2 Beds ⋅ 1 Baths ⋅ Unplatted SubDv. ⋅ 33511 Zip Code
Close to the Alafia River, .40-acre homesite. Small home existing on the property.

Brandon
$499,900
4 Beds ⋅ 3 Baths ⋅ Norma Park Sub SubDv. ⋅ 33611 Zip Code
WOW MUST SEE!! HUGE PRICE REDUCTION FOR A QUICK CONTRACT TO CLOSE QUICKLY on this RENOVATED South Tampa HOME Well BELOW Appraised $635,000 Value!! AMAZING FLOOR PLAN AFFORDS TREMENDOUS FLEXIBILITY AS 4 BEDROOM HOME PLUS Formal Living & Dining Rooms, OR as currently set up a 3 PLUS **ADDITIONAL SPACIOUS FAMILY ROOM/FLEX 4TH BEDROOM AS AN AMAZING IN LAW SUITE/GUEST ROOM w/PRIVATE 3RD BATH & WALK IN CLOSET! 3 FULL BATHROOMS ALL COMPLETELY REDONE w/STUNNING TILE TUB SURROUNDS & SHOWERS. **NEW DOUBLE PANE WINDOWS & SLIDER TO LANAI.** **BRAND NEW EXTERIOR & INTERIOR PAINT**, **PLUMBING IN 2022**, **BRAND NEW LIGHTING, FIXTURES, INTERIOR DOORS, FLOORING, TALL BASEBOARDS**, **BRAND NEW COMPLETELY REMODELED KITCHEN w/Stainless Steel High End Appliances w/SLEEK HI END HIDDEN CONTROL DISHWASHER & ULTRA MODERN DESIGN SIDE BY SIDE REFRIGERATOR w/IN DOOR WATER FILTRATION, SMOOTH TOP RANGE & BUILT IN MICROWAVE. TALL 42" Modern Shaker Cabinetry, Stunning QUARTZ COUNTERTOPS, Stainless Steel UNDERMOUNT SINK, Exquisite BRUSHED GOLD HARDWARE & PULL DOWN SPRAYER FAUCET, BUILT IN SPICE RACK & LAZY SUSAN, GORGEOUS TILE BACKSPLASH.** Spacious open Foyer & Living Room w/Stunning Bronze Fluted Accent Wall, Gorgeous BRAND NEW LVP Floors Throughout! **Absolutely no Carpeting Anywhere** LAYOUT HAS 2 WONDERFUL BEDROOMS UP FRONT to your right w/their own Beautifully remodeled bath, Stunning tub/shower combination w/Luxurious Finishes & Large Linen Closet for loads of excellent storage. Spacious Dining Room & Mud area just off the carport offers amazing convenience as a drop zone. **NOT YOUR TYPICAL SOUTH TAMPA HOME WITH NO STORAGE ** This home has LOADS OF CLOSET SPACE THROUGHOUT THE ENTIRE HOME & Large Kitchen Pantry just off the Hall. WONDERFUL MASTER SUITE **TRULY MADE for a KING SIZE BED** w/plenty of space to walk around with a dresser, nightstands, a desk & more!! TWO BUILT IN CUSTOM CLOSETS **PLUS AN ADDITIONAL WALK IN CLOSET IN THE PRIMARY SUITE. LUXURIOUS PRIVATE BATH w/LARGE WALK IN SHOWER, Exquisite Finishes- Elegant Tile Surround, Marble Curb, Brushed Gold Fixtures and Hardware & ADDITIONAL Private ACCESS TO THE BACK YARD. THE FAMILY ROOM IS AMAZING & HAS SO MUCH FUNCTIONALITY AS A FAMILY ROOM, AS A 4TH BEDROOM OR INLAW Guest SUITE W/ HUGE WALK IN CLOSET, ACCESS TO ITS OWN Luxuriously Appointed FULL BATHROOM with GORGEOUS REMODELED WALK IN SHOWER W/ LARGE SHOWER NICHE, EXTENDED VANITY, Gorgeous Hardware & Finishes as well as a large NEW SLIDING GLASS DOOR TO THE LARGE COVERED SCREENED LANAI facing the side yard & BACK YARD! LOADS OF FUNCTIONALITY AND STORAGE IN THIS REDONE DESIGN ON THIS SPACIOUS 65 FOOT WIDE OVERSIZED LOT!! The Huge Backyard offers a Large COVERED LANAI, Spacious DECK & PAVER PATIO for Entertaining, PLENTY OF ROOM FOR A POOL, Paver Walkways, Large Storage Shed w/power, Outdoor Shower. **Double Wide Driveway & Spacious 1 Car Covered Carport with room for 5 vehicles, or even a boat!!** LOW MAINTENANCE TURF & ADDITIONAL PARKING IN FRONT. A/C Mini Splits in 2021 & 2017, Main Roof in 2016, Entire Flat Roof in 2020 all in Excellent Condition! Located in the heart of South Tampa, this home offers the perfect balance of quiet residential living & unbeatable convenience. Just minutes from Bayshore Boulevard, the Selmon Expressway, Downtown Tampa, MacDill AFB, Hyde Park, Downtown St. Pete, Top-rated Cuisine, Shopping & Excellent Schools. Truly move-in ready & perfectly positioned in one of Tampa’s most desirable neighborhoods.

4105 W Bay Villa Avenue, Tampa
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