Quick Clearwater FL MLS Search

Browse All Chesterfield Heights Properties for Sale

$320,000
2 Beds ⋅ 1 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
HIGH & DRY IN FLOOD ZONE X! This 2-bedroom, 1-bathroom, 1-car garage home in desirable Chesterfield Heights offers excellent potential for an investor, vacation rental, or owner-occupant. Situated on an oversized 10,000+ sq. ft. lot, the property provides plenty of room for outdoor enjoyment, future improvements, or expansion. Legal short-term vacation rentals are permitted in the area, subject to applicable regulations, adding additional investment potential. The home is located approximately 4 miles from the Gulf beaches, with convenient access to shopping, dining and entertainment. The property is in Flood Zone X, where flood insurance is generally not required by lenders. The current sellers have never occupied the property. A great opportunity to bring your vision and unlock the potential of this well-located property!

1347 Buckingham Drive, Clearwater
$555,000
3 Beds ⋅ 3 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
Virtually Staged. This UPDATED POOL home with 3 bedrooms, 3 bathrooms, 2 car garage, and a BONUS ROOM is nestled in the desirable Chesterfield Heights neighborhood. It is MOVE-IN READY and is ideal for buyers seeking a primary residence in a well-established neighborhood surrounded by pride of ownership. It is situated on a large well-manicured lot in a quiet neighborhood and is the perfect blend of comfort, efficiency, and Florida lifestyle living. As you pull up to this home, you will notice the long driveway that can easily accommodate 6 cars. Step into a seamless blend of style and functionality with this open-concept floorplan that connects the Living Room, Dining Room, and Kitchen into a VAST & INVITING space. This design is perfect for both everyday living and entertainment with its airy and bright environment with a perfect flow from room to room. The spacious Living Room is accented with a wood burning FIREPLACE and LARGE WINDOWS, allowing natural lighting throughout the day. The RENOVATED kitchen has crisp white cabinets, SOFT CLOSE cabinets & drawers, New STAINLESS-STEEL appliances ((2025), stylish GRANITE countertops, beautiful tile backsplash, and an oversized BREAKFAST BAR, providing ample seating for all. The generous owner's suite features an en-suite bathroom and can accommodate a king-size bedroom set. Step through the sliding glass doors into the spacious Bonus Room that is perfect for a home office, play area, workout room, or TV room and/or step into your screened patio from the Bonus Room to enjoy your morning coffee or evening glass of wine. Enjoy Florida living at its best relaxing in the serene and expansive SALTWATER POOL nestled in a fully fenced yard that offers both privacy and peace of mind. You will love the ambiance at nighttime with the colored pool light, Solar fence cap lighting, and back flood lights. The MAINTENANCE FREE backyard has a large brick paved area that is perfect for a fire pit area, grilling area, or sunbathing area. It is a great space for awesome pool parties and summer barbeques with friends & family while making unforgettable memories. Updates include: New main Roof (2017), New flat roof (2024), New HVAC (2020), New duct work (2021), New Garage Door (2017), New Electrical Panel (2010), Vinyl Fence (2017), Pebble Tech pool finish (2021), New Hot Water Heater (2024), New interior/exterior paint (2024), & New Luxury Vinyl Plank flooring throughout. It even has Mini Split A/C system (not included in SF) in the garage for those that enjoy working on your car or turn it into a fully equipped gym or game room. This home is all about the LOCATION: just minutes from popular parks like Eagle Lake Park, Highland Rec Complex, Largo Central Park, and more. Whether you’re looking for outdoor adventure, arts & entertainment, or a day at the beach, you’re just 10 minutes from the award-winning Clearwater Beach and minutes to East Bay golf course, shopping, and dining hotspots. This is more than just a house - it’s a LIFESTYLE! Imagine wrapping up a project or household chores on a Saturday afternoon and rewarding yourself with a SUNSET stroll along the Gulf of Mexico. Whether you're searching for your Forever home, a sun-soaked Florida vacation retreat, or a savvy investment property, this home checks the boxes. For peace of mind, this home is in a NON-FLOOD ZONE and a NON-EVACUATION ZONE. Schedule your private showing today!

1348 Buckingham Drive, Clearwater
$570,000
3 Beds ⋅ 2 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
Whether you're searching for your forever home, a sun-soaked Florida retreat, or a savvy investment property — 1389 Chesterfield Drive has you covered. This stunning coastal gem checks every box, and then some. MOVE-IN READY | NEWLY RENOVATED | NO FLOOD ZONE | NO HOA The hard work is already done: Roof (2023), water heater (2023), 125-amp electrical panel (2022), HVAC (2019), screened lanai (2023), gutters (2023), irrigation pump (2023), and appliances (2023). Pack your bags and start living — this home is ready when you are. A recently completed four-point inspection is available upon request, giving you even greater peace of mind. Tucked into a wonderful, established neighborhood within the city limits of Largo, this beautifully designed 3-bedroom, 2-bath coastal home sits just 10 minutes from the beach. From the moment you step through the front door, something shifts — the coastal vibe wraps around you, and it immediately feels like home with a bright open layout. Luxury vinyl plank flooring flows seamlessly throughout, anchoring the open-concept design. The updated kitchen features spectacular quartz countertops, handcrafted tile backsplash, new stainless steel appliances, a designer range hood, and floating shelves that are equal parts functional and gorgeous. Step through to the screened-in lanai and let Florida do its thing. A heated in-ground pool glistens over a paver patio, surrounded by a fully fenced, private backyard complete with a pool shed. A great space for gathering with friend and family, this outdoor space was made for making memories. The primary suite is your personal sanctuary, featuring an en-suite bath and a generous sitting area large enough for a dedicated home office. Both bathrooms have been refreshed with new vanities. The two-car garage offers built-in shelving to keep life organized. And a lawn with a fully automated irrigation system that runs off a private well, without the added water bill. The flexibility here is truly rare. Approved for short-term rentals by the City of Largo, this home works beautifully as a primary residence, a second home escape, or an income-generating investment property. Turnkey setup. Furniture negotiable with a strong offer. All of this, just minutes from the Gulf beaches, top-rated restaurants, shopping, and everything the Coast has to offer. Homes like this don't wait. Neither should you.

1389 Chesterfield Drive, Clearwater
$419,000
2 Beds ⋅ 2 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
Welcome to this beautifully maintained 2-bedroom, 2-bath, single-story, solar-heated pool home that truly checks all the boxes! Nestled on a well-groomed, manicured lot in a quiet neighborhood surrounded by pride of ownership, this property offers the perfect blend of comfort, efficiency, and Florida lifestyle living. Step outside to your private screened-in in-ground pool, solar-heated when needed, featuring brand-new screening (2025), and a freshly painted pool deck (2025), all ideal for relaxing or entertaining year-round. The pool pump was replaced in 2022. Inside, the home continues to impress with thoughtful updates throughout. The kitchen has been refreshed with a new dishwasher and refrigerator (2025), while additional upgrades include newer attic insulation for improved energy efficiency (2020), an electric water heater replaced in 2023, and new ceiling fans installed in 2023 for added comfort. The fencing was partially replaced in 2023 and the yard provides privacy and space for pets or play. This home also features a long list of previous improvements including roof (2015), AC (2016), impact (hurricane) solar windows (2013), and paver driveway (2013). Paver driveway and front patio were just cleaned, re-sanded, and sealed in 2025. A convenient 8x10 shed with electricity offers additional storage or workspace. This is an extraordinary neighborhood with very very little traffic, almost no through traffic. Location is key, and this home delivers! It's just a short drive to beautiful beaches, shopping, dining, and the airport, making everyday living and weekend adventures a breeze. Don’t miss your opportunity to own this move-in ready Florida gem! Schedule your private tour today!

1365 Windsor Drive, Clearwater
$405,000
3 Beds ⋅ 2 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
Virtually Staged. This move-in ready 4-bedroom, 2-bathroom residence offers a thoughtfully designed open-concept layout with modern upgrades throughout, making it the perfect choice for buyers seeking a primary residence, vacation home, or investment property in the highly desirable Clearwater area. Step inside to discover stunning luxury vinyl plank flooring, abundant natural light, and ceiling fans throughout, creating a bright and inviting atmosphere. The fully remodeled kitchen serves as the heart of the home, featuring granite countertops, brand new stainless steel appliances, ample cabinetry, and modern finishes ideal for entertaining, family gatherings, and everyday living. The split bedroom floor plan offers privacy. Both bathrooms have been tastefully renovated with contemporary updates, porcelain tile and stylish fixtures. The enclosed Florida room has been transformed into a flexible home office and bonus space, perfect for remote work, a media room, playroom, fitness area, or guest retreat. This spacious Clearwater home also offers excellent indoor-outdoor living with an oversized fenced lot designed for both privacy and entertaining. Backyard pavers create the perfect outdoor oasis for grilling, relaxing, hosting gatherings, or enjoying the Florida lifestyle year-round. Conveniently located in the heart of Clearwater, this property is just minutes from world-famous Clearwater Beach, top-rated Gulf Coast beaches, parks, marinas, golf courses, shopping, restaurants, entertainment, and major commuter routes. With no detail overlooked, this updated Florida home combines modern convenience, versatile living spaces, and an unbeatable location near Tampa Bay amenities. Whether you're searching for a renovated Clearwater home, a spacious family property, a Florida retreat near the beach, or a turnkey single-family residence with a fenced yard and home office, this property checks all the boxes. Click the Virtual Tour link to view the 3D walkthrough. Discounted rate options and no lender fee future refinancing may be available for qualified buyers of this home.

1362 Stratford Drive, Clearwater
$326,000
3 Beds ⋅ 2 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
Picture yourself sipping your morning coffee on a sun-drenched corner lot in one of Clearwater's most charming neighborhoods — where the pace slows down, the neighbors wave, and your next chapter begins with a blank canvas just waiting for your personal touch.This spacious three-bedroom, two-bathroom home offers 1,527 square feet of living space and sits on an oversized corner lot that immediately sets it apart from the rest of the block. With a two-car garage and solid structural bones, this property is a rare find for buyers who want to create something truly special. Whether you are an ambitious renovator, a savvy investor, or a homeowner with a vision board full of dream interiors, this home is practically begging for your imagination.The generous floor plan provides a fantastic foundation to work with. Three well-proportioned bedrooms, including a primary bedroom with plenty of room to design a personal retreat, give you flexibility for family living, a home office, or a guest suite. Two full bathrooms round out the layout, offering convenience and functionality that just need your finishing touches to shine.But let us talk about that lot — because it truly steals the show. Corner lots in this area do not come around every day, and the extra square footage opens up a world of possibilities. Think expanded outdoor entertaining areas, lush tropical landscaping, or simply the luxury of breathing room that most properties in this price range simply cannot offer. The two-car garage adds valuable storage and workspace, making it easy to tackle weekend projects or keep your vehicles out of the Florida sun.Location is where this property really flexes its muscle. Situated in a well-established Clearwater community, you are just minutes from everyday conveniences that make life effortless. Publix Super Market at LaBelle Plaza is right around the corner for your grocery runs, while Eagle Lake Park offers sprawling green space perfect for morning jogs, picnics, or just a place to burn off some energy. You'll appreciate the proximity public transit access along Seminole Boulevard keeps you connected to the broader Tampa Bay area without breaking a sweat.And then there is the crown jewel of living in this part of Clearwater — stunning Sand Key Beach is a short drive away. Imagine wrapping up a renovation project on a Saturday afternoon and rewarding yourself with a sunset stroll along the Gulf of Mexico. That is not a vacation fantasy; that is just a regular weekend when you call this neighborhood home.Properties with this combination of renovation potential, generous lot size, and unbeatable location don't become available that often. The bones are solid, the possibilities are endless, and the lifestyle waiting just outside the front door is pure coastal Florida magic.Schedule your private showing today and start turning this diamond in the rough into the home you have always envisioned. Your Clearwater story starts right here.

1354 Buckingham Dr, Clearwater
$370,000
3 Beds ⋅ 2 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
One or more photo(s) has been virtually staged. Welcome to 1350 Cambridge Drive in Clearwater — a well-situated residence offering a spacious 3 bedroom, 2 bath floor plan with a 2-car garage and thoughtful layout designed for comfortable everyday living. Inside, you’ll find light-filled living areas and a functional flow that allows for both gathering and privacy. Located in an established neighborhood, this home offers a strong foundation with meaningful updates already completed, including a kitchen featuring quartz countertops, stainless steel appliances, and a large island that provides additional prep and casual dining space, along with bathrooms that have been updated over the years — leaving room for further personalization and enhancement to suit your style. The screened porch extends the living space outdoors, creating a comfortable setting for morning coffee or evening relaxation. The fenced backyard provides room to design your ideal outdoor retreat — whether that includes expanded entertaining space, a garden, or future enhancements tailored to your vision. An inside utility room with additional storage adds convenience and practicality, and the laundry area offers direct access to the garage, making daily tasks efficient and organized. The 2-car garage provides ample space for parking, storage, or workspace needs. Positioned in central Clearwater, this location offers convenient access to shopping, dining, medical facilities, and everyday services. Clearwater Beach and the Gulf coastline are approximately 6–7 miles west, offering access to white sand beaches, waterfront parks, and recreational activities. Downtown Clearwater is just a few miles away, and major roadways provide connectivity to St. Petersburg and Tampa for commuters. Nearby parks and recreational facilities offer walking trails, playgrounds, and outdoor activities, while Pinellas County schools and additional educational options are located within a short distance. With solid bones, a desirable lot, and an established setting, this property offers both immediate livability and long-term potential for enhancement. Buyers and agents to verify all information pertinent to their purchase decision. Information provided is deemed reliable but not guaranteed.

1350 Cambridge Drive, Clearwater
$505,000
3 Beds ⋅ 2 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
Fully operational and profitable short-term rental now available! This home is fully furnished and equipped with all you need to keep this successful business running, or make it your home. Either way, it has a lot to offer. The home boasts 3 bedrooms, 2 bathrooms, a 1 car garage, over ¼ acre lot, a large heated pool with gentle flow spa, large deck for relaxing and entertaining, updated kitchen and bathrooms, vinyl plank flooring throughout, newer windows and doors (2021), newer AC (2020), new water heater (2025), new dishwasher (2025), new large capacity pool heater and pool pump (2025), and newer roof (2019). Inside you’ll find updated spaces, warmth and lots of natural light, 2 living spaces, ample storage, and a layout that allows for entertaining and comfort. The oversized backyard is the perfect oasis. Here you can unwind and enjoy the outdoors in peace and privacy. From the pool, you also have direct access to a bathroom. This location is close to beaches and many options for dining and shopping. Just 15 minutes to Clearwater Beach, 12 minutes to Belleair Beach, 5 minutes to Eagle Lake Park, 25 minutes to Tampa International Airport, and more! The home’s Clearwater mailing address improves its marketability. As excellent hosts, the owners have made sure that the home is short-term rental compliant with smoke detectors, exit lights, pool safety features, fire extinguishers, safety signs, etc. They have received many 5-star reviews from happy customers. You can take it over and keep the happy customers coming!

1339 Buckingham Drive, Clearwater
$449,000
3 Beds ⋅ 2 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
FLOOD ZONE X — NO FLOOD INSURANCE REQUIRED | CONCRETE BLOCK HOME | FULLY REMODELED | NEW ROOF (2025) | NEW ELECTRICAL PANEL AND ALL NEW WIRING (2026) | NEW PRIVACY FENCE | NO HOA | NO CDD | Welcome to this move-in ready, fully renovated home in the heart of Clearwater, perfectly suited for first-time homebuyers or buyers seeking a primary residence in a well-established neighborhood. This beautifully updated 3-bedroom, 2-bathroom home offers true peace of mind with major system upgrades, including a NEW ROOF (2025) and NEW ELECTRICAL PANEL AND ALL NEW WIRING (2026). Inside, enjoy a bright and functional layout featuring a modern kitchen with stylish cabinetry, stainless steel appliances, fully remodeled bathrooms, new flooring throughout, and modern lighting fixtures thoughtfully installed in every space — designed for comfort, functionality, and everyday living. The home is located in FLOOD ZONE X, meaning no mandatory flood insurance required, and offers the freedom of NO HOA and NO CDD fees. Step outside to a screened-in porch and a spacious, fully fenced backyard, ideal for families, pets, entertaining, or simply relaxing. LOCATION IS A KEY ADVANTAGE. The home is conveniently situated near Ponce de Leon Elementary School and other schools within the Pinellas County School District, while being just minutes from parks, shopping, dining, and daily conveniences. Enjoy quick access to Downtown Clearwater, major roadways, and a short drive to Florida’s world-renowned Gulf Coast beaches, including Clearwater Beach and Honeymoon Island. Vacant | Easy to Show | Show Anytime Schedule your private showing today and take advantage of this exceptional opportunity.

1324 Chesterfield Drive, Clearwater
$374,900
4 Beds ⋅ 2 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
Four bed, two bath, one car garage, large fenced backyard, great neighborhood. New kitchen appliances.

1325 Windsor Drive, Clearwater
$370,000
3 Beds ⋅ 2 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
**Welcome to Your New Clearwater Retreat**Nestled in the desirable Chesterfield Heights neighborhood, this 3-bedroom, 2-bath ranch-style home is perfectly situated on a private corner lot in the heart of Clearwater. Built with block construction, this home offers timeless durability and great potential—making it an ideal opportunity to add your personal touch and create a true retreat. Inside, you’ll find a spacious floor plan designed for both relaxation and entertaining. The home features classic terrazzo floors that can be beautifully restored, or you can easily update with your flooring of choice. Plantation shutters add charm throughout most of the home. The kitchen combines vintage character with modern updates, including original wood cabinetry, newer granite countertops, a stainless steel undermount sink, tile backsplash, and a convenient closet pantry. The roof, replaced in 2017, and the HVAC system, updated in 2016, are both in excellent condition. New electric panel (09/2025). Impact storm windows provide peace of mind and energy efficiency, while the oversized two-car side-entry garage offers additional convenience with washer and dryer hookups. The Florida room adds approximately 220 square feet of versatile living space, not included in the heated square footage, and can serve as an office, playroom, or hobby area. The family room is centered around a cozy wood-burning fireplace, perfect for cooler evenings. The fenced backyard offers a large shed for extra storage or a workshop, along with plenty of room for outdoor living. On cooler Florida nights, it’s the perfect setting to relax by a fire and enjoy the privacy of your yard. Families will love the convenience of being just a short walk to Ponce De Leon Elementary and minutes from Eagle Lake Park, Highland Rec Complex, Largo Central Park, and other local favorites. Plus, Clearwater Beach is only 15 minutes away, with golf courses, shopping, and dining all within easy reach.

1729 Kenilworth Drive, Clearwater
$410,000
3 Beds ⋅ 2 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
Hurricane season? No problem here. This storm-secure, high-and-dry 2-bedroom, 2-bathroom home with a versatile bonus room sits in a no flood zone (flood insurance not required) and a non-evacuation zone, with a spotless record of never being touched by past storms. The bonus room makes a perfect home office, guest space, or 3rd bedroom (what its being used for currently.) Tucked in a peaceful neighborhood away from traffic, yet just 3 miles from Clearwater Beach, 2 miles from Largo Park, and minutes to East Bay Golf Course, it delivers the perfect balance of calm and convenience. Recently refreshed with brand-new exterior paint (Aug 2025) and a brand-new AC (Aug 2025), this home is truly move-in ready. Paid-off solar panels keep energy bills low, while 2024 accordion hurricane shutters, a steel front hurricane-impact door, and 2024 hurricane-impact sliding glass doors give you year-round protection. Inside, solid plaster walls and upgraded cherry wood veneer baseboards bring timeless character. The spacious family room centers around a wood-burning fireplace with a freshly designed stone accent wall — a warm and welcoming focal point. The upgraded kitchen wows with granite countertops, a granite waterfall backsplash, decorative cabinet knobs, and stainless steel appliances (refrigerator, microwave, and dishwasher all 2024; stove 2018). LED lighting brightens every space, laminate floors flow through the main living areas, and porcelain tile adds style and durability elsewhere. Both bathrooms are updated, including a refreshed main bath, and the LG washer and dryer are included. Out back, Florida living takes center stage. A sparkling kidney-shaped pool (6 ft deep at the deep end) is enclosed by a 2023 newly screened pool cage with privacy panels. The large patio offers space for lounging, dining, and hosting — and since this is Florida, outdoor entertaining is a year-round affair. There’s a grassy side yard with doggie door access from the screened porch, a brand-new shed, and double-gate access on both sides of the fence for convenience. Extra perks include a whole-house generator hookup, manual irrigation system, blown attic insulation, and a beautifully decorative epoxy driveway that boosts curb appeal. Beyond the top highlights, you’re also 2 miles to downtown Clearwater, 2 miles to Eagle Lake Park, and 3 miles to Clearwater Country Club. Zoned for top-rated Ponce de Leon Elementary (A-rated) and Largo High School, this home blends comfort, upgrades, and a true Florida lifestyle in one perfect package.

1379 Ponce De Leon Boulevard, Clearwater
$403,000
3 Beds ⋅ 2 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
PRICED TO SELL. Don't miss this solid, block built, Rutenburg home. In its time it was a registered Live Better Electrically "The Gold Medallion Home". You can still find that medal at the front door. For the record, this home has had a new electric panel and wiring installed. The entire home has a beautiful refurbished terrazzo floor with pretty shades. The green shade was carried into the kitchen granite counters and looks beautiful. The kitchen is a highlight of this home as it is both modern looking and extremely functional with many drawers (some extra ones are hidden) and shelving for pantry storage and kitchen utensils. The cabinet under the sink opens with a motor...tap on the bottom with your foot and voila! it opens! All the appliances are GE and extremely well maintained. Don't miss the "retro" main bathroom. Each bedroom has a fan and the HVAC system installed (2020) is controlled by a new Honeywell thermometer (being installed week of Apr 14-18) New garage door (2021) New Power riser installed (2024) Home was painted in Aoril 2025. DON"T MISS THIS - HOME HAS OVER 1/4 ACRE LOT WITH DOUBLE GATES TO THE BACK to store a boat, travel trailer, car. Plenty room to build a pool or another garage or addition, Yard is completely fenced. Extra Long Driveway for parking cars Come check this out. Home is move-in condition. Price reflects bathrooms can be updated to next buyer's tastes and color schemes. Seller makes no guarantee of room measurements to be exact and are to be verified by buyers.

1345 Cambridge Drive, Clearwater
$455,500
3 Beds ⋅ 2 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
Charming 3-Bedroom Home in a Quiet Neighborhood! Welcome to this beautifully maintained single-story home offering the perfect blend of comfort and convenience. Nestled in a peaceful neighborhood in Clearwater with mature trees and a spacious front yard, this property features 3 bedrooms, 2 bathrooms plus an attached 2 car garage. This home features numerous upgrades and is move-in ready. It is great for first time home buyers as well as an excellent opportunity for Short-Term rental or Airbnb investment. Also, Seller is providing a 1 year home warranty. Step inside to find a bright and inviting living space, complemented by natural light and a cozy atmosphere. The eat-in kitchen is well-appointed with ample cabinet space, stunning granite countertops, complemented by a natural stone backsplash for a stylish, modern touch. This kitchen is perfect for meal prepping and entertaining. The primary bedroom is large in size and has an attached ensuite. The second and third bedrooms are also spacious and well-sized. Enjoy the large fenced backyard, ideal for outdoor gatherings, gardening, or simply relaxing in the fresh Florida sun. The private outdoor space is complete with a remote-controlled retractable shade for comfort. There is also a matching shed that offers a convenient storage solutions for tools and equipment. Some additional upgrades: new roof (10/24), thermostat (5/21), A/C (5/22), electrical panel (8/21), fencing (4/21), garage door (2/24), dryer (10/24), water heater (11/21) and a water conditioner (12/21). All appliances were recently updated for convenience and efficiency. With its prime location near Eagle Lake Park, Highland Recreation Complex, Indian Rocks Beach, world-famous Clearwater Beach, and Downtown Clearwater, residents can effortlessly enjoy the area's natural beauty, abundant recreational opportunities, and vibrant cultural scene. Surrounded by parks, shopping, dining, and top-rated schools, this home is ideal for just about any lifestyle! Don't miss the chance to make this charming house your new home! Schedule a showing today!

1348 Chesterfield Drive, Clearwater
$329,000
2 Beds ⋅ 1 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
One or more photo(s) has been virtually staged. This home is very convenient to Tampa International Airport (TPA) and St. Petersburg Clearwater Airport (PIE). NON EVACUATION, NON FLOOD ZONE, NO HOA FEES. Chesterfield Heights is a charming neighborhood with a home town feel. Ideal location just a few miles from the beautiful sandy beaches of the Gulf and is convenient to shopping, great restaurants, and parks. This open-floor plan block home is perfect for entertaining. The kitchen has granite countertops, breakfast bar & stainless steel appliances. Imagine relaxing on the lovely screen porch overlooking your private, fully fenced backyard w/fire pit, ideal for gatherings & Florida evenings! Roof 2014, newer AC, newer windows, upgraded electrical service, new hurricane sliding door $12,050, and new exterior paint. HOME IS SPARKLING CLEAN AND MOVE IN READY. IT WILL NOT DISAPPOINT SO SCHEDULE YOUR SHOWING TODAY!

1311 Chesterfield Drive, Clearwater
$405,000
4 Beds ⋅ 2 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
Welcome to 1340 Windsor Drive, where charm meets modern upgrades at an unbeatable value! This meticulously maintained 4-bedroom, 2-bath home boasts a fresh coat of paint, a brand-new electric panel, and a new flat roof, offering peace of mind and move-in readiness. From the moment you arrive, you'll appreciate the expansive yard adorned with mature, picturesque trees, providing a serene setting. The spacious driveway ensures ample parking for family and guests. Inside, the large living room welcomes you with warmth and versatility, leading to three bedrooms and a full bath on one side of the home. The heart of the house is the beautifully updated kitchen, featuring pristine bright cabinetry, brand-new granite countertops, and a cozy eating area. Beyond the kitchen, discover the private primary suite complete with an ensuite bathroom—a true retreat within your home. Step outside to the screened lanai, perfect for enjoying tranquil evenings or entertaining friends and family. The expansive fenced backyard offers endless possibilities—plenty of space for a pool, a lush garden, or your dream outdoor oasis. Additional features include a utility area located in the garage and an unbeatable location. Just a short stroll to Ponce De Leon Elementary and minutes from shopping, dining, and entertainment options, this home is perfectly situated. Plus, you’re only a 15-minute drive to the beach and close to Largo Park, a hub for recreational activities. Don’t miss your chance to own this incredible home and start making memories today! Buyers and agents are encouraged to verify all pertinent details for their purchase decision. Room sizes are approximate, and while all information is believed to be accurate, it is not guaranteed. Your dream home awaits – seize the moment!

1340 Windsor Drive, Clearwater
$530,000
3 Beds ⋅ 3 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
**REMODELED 3 BEDROOM, 3 BATHROOM, BONUS ROOM, FULLY FENCED, SALTWATER POOL HOME!** Welcome to 1348 Buckingham Drive a beautifully renovated 3-bedroom, 3-bathroom, 2-car garage, saltwater pool home ideally located 6 miles from stunning Clearwater beaches! Step into a seamless blend of style and functionality in this updated open-concept floorplan that connects the living room, dining room, and kitchen into a vast and inviting space. Designed for both everyday living and entertainment, this layout creates an airy, bright environment with a perfect flow from room to room. Cozy up in the warm and inviting living room, accented with a wood burning fireplace and large windows, allowing natural lighting throughout the day, making it the perfect place to gather. The kitchen combines style and functionality with its crisp white cabinets, sleek black appliances, stylish granite countertops, and an oversized breakfast bar, providing ample seating for all. The generous owner's suite features an en suite bathroom, while the additional two bedrooms are ideally situated near the second bathroom, making it perfect for family members or guests. Step through the sliding glass doors into the spacious Bonus Room, the perfect space for a home office, play area, or cozy retreat, offering endless possibilities to suit your lifestyle. Enjoy Florida living at its best relaxing in the serene and expansive saltwater pool nestled in a fully fenced yard that offers both privacy and peace of mind. This refreshing oasis is complemented by the convenience of a nearby pool bathroom, allowing effortless access for all. The backyard shed provides abundant storage space, perfect for keeping tools, gardening supplies, and seasonal items organized and easily accessible. Additional updates include: Roof 2017, HVAC 2020, HVAC duct work replaced 2021, Garage Door 2017, Electrical Panel 2010, Vinyl Fence 2017, Pebble Tech pool finish 2021. Within walking distance to Ponce De Leon Elementary School and a 15-minute drive to Clearwater Beach! Conveniently located near grocery stores, restaurants, entertainment, and shopping. This home is ready for new owners to take advantage of all it has to offer, be sure to call and schedule a tour today!

1348 Buckingham Drive, Clearwater
$540,000
3 Beds ⋅ 2 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
For statistics purposes only.

1339 Buckingham Drive, Clearwater
$490,000
3 Beds ⋅ 2 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
Check out this beautiful 3 Bedroom 2 bathroom POOL home in amazing Clearwater Florida! The home was recently completely renovated with a NEW KITCHEN, Bathroom, Floors, and paint! The Roof was replaced in 2024, Impact Windows in 2021, HVAC & DUCTS 2024, and New Water Heater 2024! The Backyard was completely redone with new St. Augustine sod, irrigation, the pool has been refinished and has new equipment! Don’t miss out on this completely move in ready home!

1319 Windsor Drive, Clearwater
$300,000
2 Beds ⋅ 1 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
Welcome to your perfect starter home or cozy retreat! Nestled in a peaceful and highly desirable neighborhood, this delightful 2-bedroom, 1-bathroom property offers a blend of modern updates and comfortable living. With 1,100 square feet of thoughtfully designed space, this home is ideal for small families, couples, or individuals seeking a serene and convenient lifestyle. The inviting living area features ample natural light, creating a warm and welcoming atmosphere, perfect for relaxing or entertaining. Enjoy cooking in your modern kitchen, equipped with brand new appliances installed in 2023, sleek countertops, and plenty of cabinet space. Two generously sized bedrooms provide a peaceful retreat with ample closet space and beautiful views, while the updated bathroom is designed for comfort and convenience. This home boasts a newer roof replaced in 2020, a new hot water heater installed in 2023, and newer energy-efficient windows, ensuring peace of mind and low maintenance. The private backyard offers a tranquil setting for outdoor dining, gardening, or relaxation, and the attached one-car garage provides secure parking and additional storage. Situated near the Highland Recreation Center and just one block from Ponce De Leon Elementary School, this home is perfect for families. Enjoy the convenience of nearby shopping, hospitals, and a short drive to the stunning Clearwater Beach. Easy access to Tampa Airport makes commuting and travel a breeze. Don't miss the opportunity to make this charming home yours. Schedule a private tour today and experience the perfect blend of comfort and convenience. This gem won’t be on the market for long!

1314 Stratford Drive, Clearwater
$473,500
3 Beds ⋅ 2 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
This gorgeous remodeled three bedrooms, two bathrooms, two car garage, heated pool home in Largo Florida is now on the market! It is currently being rented through a short term rental program and it has been producing a substantial monthly income especially starting from March of this year. Everything that needed to be remodeled or replaced has already been done in this house throughout the recent years. It is located at approximately 15 minutes driving distance from Clearwater Beach, at about 30 minutes from our Tampa International airport and and it is close to multiple nearby large grocery stores. It is also conveniently located in between Downtown Clearwater and Downtown Largo, not far from downtown Dunedin and from Downtown Safety Harbor and from Downtown St Pete. This strategic location will continue to attract many guests if you choose to continue to keep it a short term rental. In the end the Clearwater, Tampa St Pete area is one of the best tourist site in the USA. The current owner has spent a lot of money in upgrades in 2023: a new permitted 200 Amps electrical panel, a new pool heater with a new pool pump and filter, two new fire proof doors between the house and the garage, new interior doors hardware throughout, new smart lock on the front door with camera and doorbell, new exhaust fans, new dishwasher, new reverse osmosis filter and new kitchen faucet. The entire inside of the house has been fully repainted. All of these upgrades costed approximately $18,000. New exterior furniture and a new barbeque have just been added for $850. The house is sold fully furnished (beds, couch, tables, chairs, mattresses, linens, kitchenware, pots and pans, etc.) making it ready to move in or to continue with the short term rental program. The owners have spent about $14,000 in new furniture only. The monthly average gross income with Airbnb and VRBO from March through June this year has been $5,400. The house has been inspected, permitted to and legally registered for short term rental with the City of Largo and the Fire Department as well. This house is fully booked through August 9, except 4 days in July. As you can see it has been upgraded just this last year, but it has also been constantly well cared by the previous owners that have owned it since 1999, so it is definitely not a cheap flip, but it is the result of two meticulous owners amazing care and upkeep. The previous owner had upgraded all the windows with hurricane proof double pane windows, I.e. there are windows replacement permits from 2008, 2011, 2014 in public records, and with custom built storm panels, the terrazzo floors throughout half of the house have been refinished, newer bamboo kitchen cabinets, quartz countertops in the kitchen, laminate floors, a lot of natural light, covered screened-in patio/lanai with fan, a new A/C was installed in 2021, a 40 gallons water heater installed in 2016 and the roof was redone in 2015. Because of the newer windows and insulation, the house is very energy efficient. The current owners will honor the current bookings until at least August and ideally this house will be sold fully furnished to investors that want to keep up with the short term rental program, but home owners looking for their forever home would also love to move in as well! This home has been loved by the current and past owners for years, it is not a flip, but everything has been done for the occupants to love it, not just for looks!

1713 S Betty Lane, Clearwater
$525,000
3 Beds ⋅ 2 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
Welcome home to this beautiful and spacious 3 bedroom 2 bath Clearwater POOL home! GREAT OUTDOOR LIVING SPACES with a beautiful back yard overlooking a REFINISHED POOL with NEW POOL EQUIPMENT and NEW ST AUGUSTINE GRASS all around the house. The yard also come equipped with a NEW IRRIGATION SYSTEM. This home has been TOTALLY RENOVATED by the owner and includes upgrades perfectly fit for anyone looking for a truly turnkey home. The totally remodeled kitchen features solid wood cabinets, quartz countertops, stainless steel appliances, custom backsplash, and a designer faucet. The bathrooms feature the same level of upgrades including custom vanity, quartz countertops, designer tile, and new hardware. Other upgrades include NEW ROOF (2024), NEW IMPACT WINDOWS (2021), NEW HVAC & DUCT WORK (2024), NEW WATER HEATER (2024), new flooring throughout, new paint, new LED light fixtures, and MORE!! All of these amenities and upgrades are complimented by the unique curb appeal of the home which sits on a quiet street! This home has many desirable features and is a must see. Please call us or use ShowingTime to set up a showing today!

1319 Windsor Drive, Clearwater
$250,000
2 Beds ⋅ 1 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
*** CASH ONLY***ENCLOSED PORCH IS NOT INCLUDED IN THE SQUARE FOOTAGE*** This 2 Bedroom, 1 Bathroom, 1 Car garage home has endless possibilities from a fix and flip with great profit potential, to a fix and rent either long term OR LEGAL SHORT TERM VACATION RENTALS ALLOWED IN THAT AREA, or personalize it and make it your own so you can move in and live the Florida dream! (2010 ROOF) (HVAC AROUND 30 YEARS) (CURRENT SELLERS HAVE NEVER LIVED IN THE PROPERTY) This property sits high and dry in flood zone X where there is NO FLOOD INSURANCE REQUIRED. The oversized lot (over 10,000 sq ft) is on a very quiet street in the desired Chesterfield Heights neighborhood which is just 4 miles from World Famous Beaches. There is terrazzo flooring throughout the entire home underneath the carpet that is just waiting to be polished to its original beauty. Don't miss out on your chance to purchase this property that presents so many opportunities and possibilities. Schedule your tour today!

1347 Buckingham Drive, Clearwater
$487,000
4 Beds ⋅ 2 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
TAKING BACK-UP OFFERS! This delightful 4-bedroom, 2-bathroom pool home is perfectly situated just 6 miles from the beautiful beaches. It boasts a prime location near Largo, Eagle Lake Park, Highland Recreation Complex, St. Petersburg, Clearwater Beach, and Downtown Clearwater, offering easy access to a variety of attractions and amenities. Upon entering, you'll immediately notice the small touches that enhance the home’s warm and inviting atmosphere. The kitchen has been thoughtfully updated and creates a space that is both functional and stylish. Similarly, the master bathroom has been updated. The spacious Florida room is a highlight, providing picturesque view of the backyard. This room opens up to the inviting in-ground pool, making it an ideal spot for unwinding after a long day or hosting gatherings with friends and family. The exterior of the property is equally impressive, featuring a large front driveway and a welcoming porch. The fenced backyard offers ample space for various outdoor activities, whether it's, playing, or simply basking in the Florida sunshine with loved ones and pets. Additionally, the home’s new roof, installed in 2019, ensures durability and reduces the need for immediate maintenance, providing peace of mind for years to come. Are you ready to live the Florida dream? Book a showing today!

1354 Chesterfield Drive, Clearwater
$395,000
3 Beds ⋅ 2 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
Just Remodeled 3 bedroom, 2 bath, 1 car garage on a huge lot less than 15 mn from World-Renowned Clearwater Beach! Roof 2016, Facia 2023, New Ac, Double Pane Windows and New Glass Sliders leading to a huge fully fenced in backyard. Freshly painted inside and out. New kitchen cabinets, New Granite countertops, Under-mount sink, New Stainless Steel Appliances with breakfast counter. Both bathrooms have been remodeled with one of them being in the primary bedroom.

1325 Chesterfield Drive, Clearwater
$465,000
3 Beds ⋅ 2 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
Welcome home! This enchanting 3-bedroom, 2-bath residence beckons those seeking a move-in ready haven. Located in a peaceful Clearwater neighborhood, this home exudes loads of curb appeal and boasts an open, bright interior that seamlessly combines the charm of a tropical oasis with a touch of the Caribbean. Perfect for both entertaining and relaxing, this residence showcases quality craftsmanship throughout. The beautiful pool and private backyard oasis create an inviting atmosphere, while the kitchen, equipped with stainless steel appliances, opens to the dining room, offering ample storage. The primary bedroom, with sliders leading to the pool area, features plentiful closet space and a charming renovated ensuite with a walk-in shower. Additional bedrooms are bathed in natural light and share a generously-sized bath with a tub-shower combo. Extras include roof solar fans for the attic, fresh paint inside and out, firepit and grilling area and newly resurfaced pool with pavers. Ideally situated, this home is only a 10-minute drive from sparkling beaches and conveniently close to shopping, restaurants, and two airports. Discover the essence of Florida living in this well-appointed dwelling.

1361 Windsor Drive, Clearwater
$510,000
4 Beds ⋅ 2 Baths ⋅ Chesterfield Heights SubDv. ⋅ 33756 Zip Code
Welcome to this meticulously renovated 4-bedroom, 2-bathroom pool home that seamlessly blends warmth with contemporary aesthetics and modern amenities. As you step inside, you'll find an inviting space with extensive upgrades and attention to detail. The property boasts a brand new roof installed in 2016 and new flat roof in 2021 ensuring durability and longevity. The kitchen is a chef's delight, featuring white maple cabinets, full-overlay doors, and 3/4" dovetail full extension soft-close drawers. Granite countertops and stainless steel appliances add a touch of luxury to this functional space. Both bathrooms have been tastefully renovated, contributing to the overall modern and elegant feel of the home. The family room, adorned with new sliding glass doors, seamlessly connects to the inviting pool and the fully fenced rear garden, complete with a convenient shed. Notable upgrades include new ceramic tiles in the area in 2016, providing both style and practicality. All-new Armortech windows were installed in 2017, enhancing energy efficiency and aesthetics. A new electric panel with generator input was added in 2018, ensuring the home is well-prepared for any situation. Step outside to the pool area, and you'll find new pool deck pavers installed in 2019, creating a stylish and functional outdoor space. This meticulously maintained home also benefits from a new pool cartridge, ensuring the pool stays in pristine condition, with the replacement made in 2023. A new white vinyl fence, added in 2018, ensures privacy and enhances the overall aesthetics of the property. The exterior of the house received a fresh coat of paint in 2019, adding to the home's curb appeal. The air conditioner was updated in 2020, now featuring a UVC light for improved air quality, and a whole house filter was added in 2021 for added comfort. Conveniently located within walking distance to shopping, 2 minutes to Eagle Lake Park, and a short 12-minute drive to the beach, this residence offers a perfect blend of comfort, style, and functionality. Schedule a viewing today to experience all that this upgraded and thoughtfully maintained home has to offer.

1341 Buckingham Drive, Clearwater
Start Your Search

Chesterfield Heights Real Estate & Homes