Location: Clearwater, 33755
Do Not Show Listings
1221 DREW ST #B3, CLEARWATER, FL 33755
$90,000199 Days on yellowkey MLS ID: TB8459988
REDUCED by $2,000 (2.2%) on 05/07/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 705 Built: 1966 Tax: $1,267 (2025)Community: Drew Ridge Apts Co-OpCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,267
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Turnkey, worry-free living in a desirable Clearwater 55+ community. This well-maintained Unit is currently rented for $1,300/month to a strong, reliable tenant, making it an excellent income opportunity or future personal residence. The condo has been tastefully updated and very well cared for, offering a clean, comfortable feel that stands out. No known issues, no deferred maintenance, and no special assessments—a truly low-stress ownership option. Ideally located close to shopping, dining, medical facilities, and major roadways, with everything you need just minutes away. Priced to sell and perfect for buyers seeking convenience, stability, and long-term value in a well-established 55+ community.
Listing is courtesy of: MCBRIDE KELLY & ASSOCIATES (813-254-0900)
Listing Agent: Brain Albores Hernandez (727-365-6263)
2075 N KEENE RD, CLEARWATER, FL 33755
$469,000150 Days on yellowkey MLS ID: TB8477685
REDUCED by $20,999 (4.3%) on 06/17/2026
Bed: 4 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1788 Built: 1964 Tax: $7,875 (2025)Community: Montclair Lake EstatesSpa: NoSingle Family
Taxes:$7,875
Elementary School: Dunedin Elementary-PN
High School: Dunedin High-PN
Middle School: Dunedin Highland Middle-PN
Remarks: SELLER MOTIVATED!!! Life is Better at Lake Montclair. Beautifully remodeled Florida Lakefront home featuring 4 bedrooms and 2 bathrooms, 1.5 car garage, huge pool with large enclosure and PVC fenced yard. Separate family and living rooms are perfect for entertaining and the formal dining room is a must see. Spacious bedrooms full of light with mirrored closet doors. Enjoy 2 sliding doors that open up to the oversized enclosed pool area that gives wonderful views of the Lake. This home is conveniently located just minutes from downtown Dunedin and is in Dunedin School zones. A portion of this mortgage is assumable
Listing is courtesy of: BUFFINGTON PROP MGMT INC (727-518-8700)
Listing Agent: Krista Kosier (727-798-0972)
1004 N BETTY LN, CLEARWATER, FL 33755
$409,900150 Days on yellowkey MLS ID: TB8477676
REDUCED by $10,100 (2.4%) on 05/29/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1550 Built: 1974 Tax: $7,098 (2025)Community: Fair Burn AddSingle Family
Taxes:$7,098
Elementary School: Sandy Lane Elementary-PN
High School: Clearwater High-PN
Remarks: Beautiful 4-bedroom, 3-bathroom single-family home located in desirable Clearwater, FL. This well-maintained home offers approximately 1,550 square feet of comfortable living space that has been completely remodeled. Open concept floorplan with large kitchen, Granite countertops, stainless steel appliances, new flooring and beautiful fireplace. This home is a MUST SEE, with 4 bedrooms and 3 baths can accommodate comfortably. Split floor plan with 2 master bedrooms, fully updated baths, free standing bathtub, dual sinks and walk in shower. Situated next to a golf course, the home provides a quiet, relaxing setting while still being close to shopping, dining, beaches, and major roadways. Spacious bedrooms, multiple bathrooms, and an open layout make it ideal for families or seasonal residents looking to enjoy Florida living. Schedule your appointment today.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Ervis Muso (727-688-8814)
1507 TALISKER DR, CLEARWATER, FL 33755
$274,999101 Days on yellowkey MLS ID: TB8494862
REDUCED by $5,801 (2.1%) on 05/14/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1416 Built: 2008Monthly Fee: $240 Tax: $5,184 (2025)Community: Highland GlenTownhouse
Taxes:$5,184
Remarks: CLEARWATER DIAMOND IN THE ROUGH! PRICE IMPROVEMENT!! MOTIVATED SELLER!! Solid Block Construction in Prime Clearwater Location! Welcome to 1507 Talisker Dr. This spacious 3-bedroom, 2.5-bath, 1-car garage townhouse is located in the desirable Highland Glen community. Built in 2008 with durable block construction, this home offers 1,416 sqft of living space and a functional layout ready for your personal touch. The roof was replaced in March of 2024, providing peace of mind for years to come. While it does need some cosmetic updates, the home features strong bones, solid structure, and great potential! Enjoy unbeatable convenience with close proximity to some of Pinellas County’s most desirable destinations. You are approximately 1.5 miles from Downtown Dunedin, Edgewater Dr, and the Intercoastal. 3 miles from US 19, major shopping and dining. 3 Miles from Downtown Clearwater, 5 miles from the world-famous Clearwater Beach, and 18 miles from Tampa International Airport. Whether you're heading to the beach, enjoying Dunedin’s vibrant dining scene, or commuting across the Tampa Bay area, this location puts you right in the middle of it all. With major systems already addressed and just cosmetic updates needed, this is your chance to own a well-built home in a high-demand area at a great value! Don't wait to schedule your showing today!
Listing is courtesy of: THE SHOP REAL ESTATE CO. (727-593-7777)
Listing Agent: Jessica Martin (901-240-9790)
500 N OSCEOLA AVE #406, CLEARWATER, FL 33755
$524,000128 Days on yellowkey MLS ID: TB8479503
REDUCED by $25,000 (4.6%) on 06/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1450 Built: 1974Monthly Fee: $1,280 Tax: $7,849 (2025)Community: Harbor Bluffs Waterfront CondoCondo
Taxes:$7,849
Remarks: Rare 2 Bedroom 2 Bath Open Waterfront View at Harbor Bluffs Waterfront in downtown Clearwater. The balcony overlooks St. Joseph's Sound Intercoastal Waterway from the entire length of this spacious 4th floor unit from every room with floor to ceiling windows in both bedrooms and living room. Enjoy waterfront breezes while entertaining or watching wildlife, boaters and gorgeous sunsets. Harbor Bluffs is a gated waterfront condo building with 2 elevators, an interior courtyard, fitness center, pool, dock and clubhouse, all overlooking the Intercoastal. One designated storage room on the 1st floor also conveys as well as one covered parking space. There is also guest parking. Kitchen is well equipped with an electric Kenmore Elite range that offers 2 ovens for baking, as well as a convection setting. Privacy is at a premium with a split bedroom floor plan and 2 separate entrances to the unit. Primary bedroom boasts dual closets and an ensuite bathroom with a walk-in shower. This property is located near vibrant downtown, home to Ruth Eckerd’s Capital Theater and Coachman’s Park Sound Venue, both with worldwide top performers. Listen to entertainers perform from the Sound Venue FROM THE COMFORT AND PRICACY OF YOUR BALCONY! Downtown has many popular delectable restaurants, as well as fabulous shopping, the Clearwater library, several banks, Clearwater Court House, Clearwater downtown Marina, Seminole boat ramp and Clearwater Playhouse. All within a short walking distance from Harbor Bluffs Condominium. Famous Clearwater beach is just over the Clearwater Memorial Causeway, as well as the Clearwater Aquarium, home to Winter and also the popular Island Way Grill Restaurant. Enjoy walks on the beach, sunsets, entertainment and other famous restaurants on Clearwater beach. Only a short drive to Dunedin, Tarpon Springs, Tampa and St. Petersburgh. Experience a tranquil lifestyle at Harbor Bluff with excitement around every corner. New electrical panel 2023, HVAC 2023. LG Thin Q front loading washer and dryer convey with purchase.
Listing is courtesy of: FLORIDA PREMIERE REALTY (727-437-0261)
Listing Agent: Anna Stamas (727-492-0019)
200 N BETTY LN #1C, CLEARWATER, FL 33755
$99,900121 Days on yellowkey MLS ID: A4686445
REDUCED by $25,100 (20.1%) on 06/16/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 875 Built: 1955Monthly Fee: $497 Tax: $1,347 (2025)Community: Betty Drew Apts Co-OpCondo
Taxes:$1,347
Remarks: **MAJOR PRICE IMPROVEMENT - JUNE 2026** Welcome to Unit 1-C at 200 N Betty Lane! This 55+ cooperative community offers an inviting opportunity to enjoy relaxed, low-maintenance living in the heart of Clearwater. This charming unit comes completely TURNKEY FURNISHED and features a comfortable and efficient layout that makes the most of its space. The bright interior creates a warm and welcoming atmosphere, while the functional floor plan provides comfort and flexibility. Whether you're looking for a full-time residence, an investment property, or a seasonal retreat, this condo offers a wonderful place to call home! This 1-bedroom, 1-bath unit features low maintenance TERRAZO flooring, stainless steel appliances, and the convenience of GROUND FLOOR living - Just steps away from your assigned COVERED parking space, assigned private storage area, and the ground level laundry room! The location is another standout feature. Walk to the beautiful Clearwater Country Club or take a short 10-minute drive to the world-famous Clearwater Beach, celebrated for its powder-soft sand, beautiful Gulf waters, and spectacular sunset views. Whether you enjoy morning beach walks, waterfront dining, or simply soaking up the Florida sunshine, the coast is always within easy reach. Nearby Coachman Park has recently been beautifully redeveloped and serves as a gathering place for concerts, festivals, and waterfront recreation throughout the year. Residents can also explore local attractions such as the Clearwater Marine Aquarium, a beloved destination known for marine life rescue and education. Everyday conveniences are close at hand as well, with shopping, grocery stores, medical services, and dining options located just minutes from the community. The central Pinellas County location also allows easy travel throughout the Tampa Bay area, with convenient access to both St. Petersburg and Tampa for additional cultural attractions, sporting events, and airport access. Unit 1-C at 200 N Betty Lane offers the perfect blend of comfort, community, and location—making it an excellent opportunity to enjoy the relaxed lifestyle that makes Clearwater such a sought-after place to live.
Listing is courtesy of: NETWORK REAL ESTATE GROUP (941-803-0344)
Listing Agent: Shawn Peacher (703-405-2615)
1735 UNION ST, CLEARWATER, FL 33755
$420,000123 Days on yellowkey MLS ID: TB8477663
0 Days Off yellowkey (back on 6/14/2026)
REDUCED by $15,000 (3.4%) on 06/01/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2252 Built: 1974 Tax: $2,112 (2025)Community: Windsor Park 3Rd AddSingle Family
Taxes:$2,112
Remarks: Under contract-accepting backup offers. Virtually Staged. Significant Price Improvement! Welcome to a home where generous space meets endless possibilities. This 3-bedroom, 2-bath home with over 2,250 square feet and multiple living areas designed for comfortable Florida living. A private gated courtyard entry welcomes you and leads to the main front doors, creating an inviting first impression. Inside, the kitchen and dining area flow into an open-concept layout, while the great room offers a tremendous living space that can easily accommodate both a large living area and, if desired, a formal dining room. The Florida room is the perfect place to relax with a book or enjoy peaceful views year-round. Just beyond the Florida room is a large bonus room that provides fantastic flex space—ideal for a home office, hobby room, fitness area, or additional entertaining space. Bring your imagination and make it your own. A newer spa is included in the sale of the home. Centrally located on the Clearwater/Dunedin city line and close to the beautiful Gulf beaches. Just minutes from the charming downtown Dunedin district, where a walkable Main Street offers unique shops, outside markets, restaurants, breweries, and boutiques.
Listing is courtesy of: BILTMORE GROUP INC (727-559-2008)
Listing Agent: Donna Kelly (727-742-8482)
1860 N FORT HARRISON AVE #402, CLEARWATER, FL 33755
$975,000366 Days on yellowkey MLS ID: TB8405599
0 Days Off yellowkey (back on 6/15/2026)
REDUCED by $24,000 (2.4%) on 05/26/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2512 Built: 2005 Tax: $4,308 (2024)Community: Villa Del Mar Of Clearwater CondoCondo
Taxes:$4,308
Tax Year: 2024
Remarks: Under contract-accepting backup offers. 3 BEDROOMS ~ 2.5 BATHS ~ very rare LARGE 2 CAR GARAGE plus a BOAT SLIP! Welcome to Villa del Mar, where elegance meets coastal serenity in one of Clearwater’s most refined waterfront enclaves. Perched gracefully on the top floor of an intimate 24-residence building, with over 2,500 sq ft, this home is the epitome of waterfront living. A private, deeded boat slip conveys with the residence, offering effortless access to the open water for sunset cruises and weekend adventures. From your private elevator foyer, enter through the custom stained-glass doors into a residence where every inch has been curated with elevated taste and craftsmanship. Rich travertine flooring seamlessly connects expansive living and dining spaces to a grand waterfront terrace perfect for both vibrant entertaining and tranquil reflection. Designed with the connoisseur in mind, this home features a gourmet kitchen with a raised ceiling and fan, oversized granite countertops, built-in cabinetry, and top-of-the-line appliances. Custom China cabinet and pantry roll-out drawers offer both luxury and practicality. The living room, wrapped in glass, features remote-controlled blinds that frame the breathtaking vistas beyond. The primary suite is a retreat unto itself, offering a spacious layout, raised ceilings with a fan, custom cabinetry, and a spa-style bath complete with a built-in glass tile shower and roll-out drawers throughout. Two additional bedrooms include elegant touches—one with a built-in oak desk and pull-down bed. Luxury continues throughout with remote-controlled see-through hurricane screens on the balcony engineered to withstand Category 5 storms. Plus inside remote-controlled blinds. This condo also offers a 2-Car Garage with upgraded emergency power control, ideal for storm readiness. All this, just moments from the vibrant culture of Downtown Dunedin, Clearwater Sound, the beaches of Honeymoon Island, and a lifestyle that blends upscale tranquility with easy coastal access. This is more than a home, it’s a celebration of waterfront luxury, artistry, and timeless design. Condo reserves are fully funded, and all reports are readily available for buyer confidence. This perfect condo is just waiting for you.
Listing is courtesy of: COASTAL PROPERTIES GROUP INTERNATIONAL (727-493-1555)
Listing Agent: Kelly Castellano (727-458-6267)
1880 N WASHINGTON AVE, CLEARWATER, FL 33755
$989,000296 Days on yellowkey MLS ID: TB8430292
REDUCED by $10,000 (1.0%) on 05/19/2026
Bed: 4 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2335 Built: 1926 Tax: $8,715 (2024)Community: Sunset RidgeSpa: YesSingle Family
Taxes:$8,715
Remarks: Experience the best of coastal living with this versatile, income-generating property, nestled within a serene tropical landscape. Ideal for investors, multi-generational living, or those seeking a live/work retreat, this rare gem features multiple residences, lush outdoor spaces, and direct access to the Pinellas Trail. Steps from the Dunedin border! The grounds feel like your own private resort, surrounded by mature shade oaks, swaying palms, and even your own mango tree. Brick walkways wind through cozy nooks and open gathering areas, perfect for enjoying Florida’s outdoor lifestyle. Designed with Spanish-inspired architecture, the main residence greets you with a circular brick driveway, clay tile roof accents, and a welcoming porch with Spanish tile flooring. Step inside through wood-framed French doors to a charming living room featuring hardwood floors and a classic fireplace. The adjacent dining room is flooded with natural light from a picture window overlooking a lush garden, while the fully renovated kitchen is both stylish and functional, boasting granite countertops, white shaker-style soft-close cabinetry, hammered copper dishwasher (2024), Induction range (2025) and a "smart" refrigerator (2025). A laundry/storage room includes a stacked washer/dryer, utility sink, and shelving. A leaded glass door leads you to the rear patio and garden, where a private hot tub awaits. The primary bedroom offers newer luxury vinyl flooring and a private sunroom perfect for a home office, yoga space, or quiet reading nook with direct yard access. The second bedroom connects to an updated bath with basket-weave stone tile flooring and a modern walk-in shower. Accessible from both inside the home and via a wide outdoor staircase, this bright and spacious second-floor suite is perfect as a primary ensuite, guest quarters, or rental unit. Features include an oversized private deck, kitchenette with butcher block counters, soft-close cabinetry, and stainless sink, Murphy Bed for flexible living and a full bath with tiled tub/shower combo. Across from the main house, a charming standalone cottage offers a bright, open living area with large sliding windows, tile countertops, ample kitchen storage, and space for dining/game area. There is also a private bedroom with walk-in closet and a full bath and private rear patio… perfect for guests, short-term rentals, or extended family stays. Features & Upgrades include high-efficiency mini-split HVAC systems in all residences, newer sewer lines and main water supply lines to both main house and cottage, a gas water heater (2019), Tesla charging station, and one-car garage with newer garage door. NO HOA. FLOOD ZONE X. This unmatched location is situated directly on the Pinellas Trail, enjoy 47 miles of scenic biking and walking from your backyard. Ride north to Downtown Dunedin’s shops, microbreweries, and farmers markets, or head south to historic Clearwater and world-famous Clearwater Beach. Just a block away, launch your kayak to explore uninhabited coastal islands or drop your boat in at the Seminole Boat Ramp. You're also minutes from award-winning beaches, premier golf courses, top-rated hospitals, airports, restaurants, retail, and live music venues. This is more than a home — it’s a lifestyle. Whether you're looking for a profitable investment, a multi-unit family property, or a peaceful tropical retreat, this Clearwater oasis has it all.
Listing is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)
Listing Agent: Linda Caruso (727-410-7501)
628 CLEVELAND ST #904, CLEARWATER, FL 33755
$499,95093 Days on yellowkey MLS ID: TB8498334
REDUCED by $25,050 (4.8%) on 06/03/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1636 Built: 2008 Tax: $7,667 (2025)Community: Station Square CondoCondo
Taxes:$7,667
Elementary School: Belleair Elementary-PN
Middle School: Oak Grove Middle-PN
Remarks: Welcome to 628 Cleveland Street, Unit 904 an impeccably maintained residence perched high above the heart of Downtown Clearwater. From the moment you step inside, you’ll immediately feel the exceptional care and pride of ownership that make this home truly stand apart. Light-filled and inviting, the open layout offers an effortless flow for both relaxing and entertaining, while expansive windows frame beautiful natural light along with a subtle glimpse of the water in the distance. Fresh, refined, and move-in ready, this residence offers the perfect canvas for a buyer seeking a downtown lifestyle. Every space has been thoughtfully maintained, creating a sense of comfort, cleanliness, and understated elegance throughout. Rarely do you find a home this immaculate and ready for immediate enjoyment. Adding to its appeal are TWO assigned indoor garage parking spaces an incredible convenience and rarity for downtown living. Located in the center of exciting Downtown Clearwater, residents are surrounded by a city experiencing remarkable transformation and growth. Enjoy being moments from waterfront parks, the revitalized Cleveland Street District, concerts and events at The Sound at Coachman Park, boutique dining, cafés, entertainment, and the beautiful Clearwater waterfront. With easy access to Clearwater Beach, marinas, the Pinellas Trail, and vibrant community events year-round, this location offers the perfect blend of energy, walkability, and coastal lifestyle. Whether you are searching for a full-time residence, seasonal retreat, or lock-and-leave lifestyle, Unit 904 offers elevated downtown living in one of Clearwater’s most exciting and evolving locations.
Listing is courtesy of: PREMIER SOTHEBY'S INTL REALTY (727-595-1604)
Listing Agent: Janet Moore (813-892-0998)
1020 SUNSET POINT RD #111, CLEARWATER, FL 33755
$1,225,00061 Days on yellowkey MLS ID: TB8509493
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1409 Built: 2023Monthly Fee: $1,405 Tax: $14,820 (2025)Community: Serena By The Sea CondoCondo
Taxes:$14,820
Remarks: An exceptional opportunity in one of Clearwater’s most sought-after luxury waterfront communities, this beautifully designed 2-bedroom, 2-bath residence at Serena by the Sea is competitively priced below comparable units, offering incredible value for buyers seeking luxury, location, and lifestyle. Experience luxury waterfront living with breathtaking water views in a home designed with a spacious open floor plan filled with natural light, seamlessly blending indoor and outdoor living. The gorgeous chef-inspired kitchen features a stunning 10-foot waterfall Quartz island, premium Gaggenau gas stove, built-in oven, paneled refrigerator, and custom-designed Italian cabinetry, creating the perfect space for entertaining family and friends. Floor-to-ceiling windows showcase beautiful bay views, creating a peaceful coastal backdrop throughout the main living areas. The thoughtfully designed split-bedroom layout offers both comfort and privacy, while high-end finishes, hardwood flooring in the bedrooms, abundant closet space, and modern luxury design add to the home’s upscale appeal. Enjoy the private terrace stretching from the primary bedroom to the second bedroom, offering the perfect place to relax and take in the coastal surroundings. The condominium is elevated approximately 10 feet above ground level and also includes an assigned covered corner parking space along with a temperature-controlled storage unit. Residents enjoy exceptional resort-style amenities including 24/7 concierge service, a heated waterfront saltwater pool overlooking Clearwater Bay, private cabanas, an outdoor grilling area with TVs and seating, elegant fire pit lounges, a luxurious wellness spa with sauna and cold plunge, a state-of-the-art fitness center, stylish clubhouse and social spaces, and secure gated access for peace of mind. Serena by the Sea is a gated boutique luxury condominium community ideally located just minutes from Clearwater Beach and the shops and restaurants of Dunedin, with convenient access to St. Petersburg, Tampa, and Tampa International Airport. Enjoy being just a short distance from the Pinellas Trail, perfect for biking, walking, and enjoying the Florida lifestyle.
Listing is courtesy of: LUXURY & BEACH REALTY INC (727-800-5906)
Listing Agent: Betty Rohe (301-366-3208)
411 PLEASANT ST, CLEARWATER, FL 33755
$875,00038 Days on yellowkey MLS ID: W7886599
0 Days Off yellowkey (back on 6/12/2026)
Bed: 25 Bath: 0.0 Liv Area Sq Ft: 3134 Built: 1951 Tax: $5,213 (2025)Community: North Shore ParkApartment
Taxes:$5,213
Remarks: Under contract-accepting backup offers. Looking for a great rental complex with 5 units and solid rental income which could increase substantially depending on what the new owner prefers in rental options??? Welcome to 409 and 411 Pleasant Street (sold together), this exceptional investor’s rental gem is a rare opportunity to own a high-performing quadplex literally steps from the ocean. The property features five separate apartments, including three 1-bedroom/1-bath units, one 2-bedroom/1-bath unit, and one efficiency apartment, offering a diverse rental mix ideal for maximizing occupancy and income potential. Tenants and guests can enjoy a relaxing community pool, while the property’s prime location places it only 5-10 minutes from world-famous Clearwater Beach and close to major shopping, dining, entertainment, and popular tourist attractions. With a current annual rental income from long term tenants of approximately $72,000, this income-producing property presents an outstanding opportunity for investors seeking strong cash flow in one of Florida’s most desirable coastal markets.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (727-845-4321)
Listing Agent: Michael Constantine (727-415-0922)
$875,00057 Days on yellowkey MLS ID: W7885997
Bed: 5 Bath: 5.0 Liv Area Sq Ft: 3134 Built: 1951 Tax: $5,213 (2025)Community: North Shore ParkCondo
Remarks: Under contract-accepting backup offers. Looking for a great rental complex with 5 units and solid rental income??? Welcome to 409 and 411 Pleasant Street (sold together), this exceptional investor’s rental gem is a rare opportunity to own a high-performing quadplex literally steps from the ocean. The property features five separate apartments, including three 1-bedroom/1-bath units, one 2-bedroom/1-bath unit, and one efficiency apartment, offering a diverse rental mix ideal for maximizing occupancy and income potential. Tenants and guests can enjoy a relaxing community pool, while the property’s prime location places it only 5-10 minutes from world-famous Clearwater Beach and close to major shopping, dining, entertainment, and popular tourist attractions. With a current annual rental income from long term tenants of approximately $72,000, this income-producing property presents an outstanding opportunity for investors seeking strong cash flow in one of Florida’s most desirable coastal markets.
1221 DREW ST #D9, CLEARWATER, FL 33755
$89,00037 Days on yellowkey MLS ID: TB8515579
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 675 Built: 1967Monthly Fee: $439 Tax: $82 (2025)Community: Drew Ridge Apts Co-OpSpa: NoCondo
Taxes:$82
Remarks: Enjoy easy Florida living in this charming 2nd-floor condo located within a quiet 55+ Clearwater community. Situated outside of a flood zone, this residence offers peace of mind and a convenient location close to beaches, healthcare, shopping, and transportation. Inside, you'll find a bright interior featuring updated flooring, neutral finishes, and a newer air conditioning system. The spacious primary bedroom offers excellent closet space, including a large walk-in closet and updated impact-rated windows. Whether you're looking for a year-round residence or a seasonal escape, this move-in-ready condo presents an excellent opportunity to enjoy comfort, convenience, and value in a desirable Clearwater location.
Listing is courtesy of: CAPSTONE REALTY & ASSOCIATES (727-301-7855)
Listing Agent: Julianne Williams (213-718-4316)
1169 DREW ST, CLEARWATER, FL 33755
$340,00037 Days on yellowkey MLS ID: O6416051
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1119 Built: 1954 Tax: $3,632 (2025)Community: BassadenaSingle Family
Taxes:$3,632
Remarks: Perfect opportunity for both **homeowners and investors**! This well-maintained **2-bedroom, 1-bath home** provides spacious living areas, abundant natural light, and tile flooring throughout. The home is **not furnished** and has been extensively upgraded within the last year, including **brand-new impact windows and doors**, a **new certified electrical panel**, **new water heater**, and **new attic insulation**. The roof has approximately **10 years of remaining useful life**, providing added peace of mind. Ideally located just minutes from **Clearwater Beach**, one of Florida's most renowned beaches, and close to a local golf course, this property gives the perfect blend of convenience and lifestyle. Enjoy being only 5 minutes from downtown, with easy access to restaurants, shopping, entertainment, and major roadways. With numerous new developments and improvement projects taking place throughout the area, the neighborhood continues to experience growth and revitalization, making this an attractive opportunity for those seeking a primary residence, summer home, or investment property with strong future potential. Buyer to verify all information and measurements independently. Shared driveway with the adjacent multifamily unit . Parking is behind the property. Don't miss out on one of the only NO HOA deals in the area . Seller is a Real Estate agent. Only serious buyer
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
625 N KEENE RD #B, CLEARWATER, FL 33755
$165,00037 Days on yellowkey MLS ID: TB8518063
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 922 Built: 1976 Tax: $2,330 (2025)Community: St Andrews Cove CondoCondo
Taxes:$2,330
Remarks: Discover exceptional value and convenience in this beautifully remodeled ground-floor condominium. Featuring 3 bedrooms and 1 bathroom, this move-in-ready home offers stylish upgrades throughout, including real stone flooring, a completely renovated kitchen, an updated bathroom vanity, fresh interior paint, and more. The screened lanai provides a peaceful setting with scenic golf course views while also offering additional storage space. Ideally located just minutes from stunning Gulf beaches, shopping destinations, restaurants, entertainment venues, and major airports, this home places everything you need within easy reach. With a low monthly HOA fee of only $545, residents enjoy a worry-free lifestyle that includes cable TV, water, sewer, trash service, and access to a community pool. Whether you're searching for a primary residence, seasonal retreat, or investment opportunity, this affordable and well-appointed condo is a fantastic find. *Owner Financing Available with a 3 year balloon*
Listing is courtesy of: INSPIRED REALTY, LLC (727-503-7865)
Listing Agent: Nicholas Shoemaker (727-910-6073)
864 N OSCEOLA AVE, CLEARWATER, FL 33755
$1,875,000216 Days on yellowkey MLS ID: TB8456435
REDUCED by $75,000 (3.8%) on 06/11/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3323 Built: 2024Monthly Fee: $1,200 Tax: $8,400 (2023)Community: Marina Bay Master CondoTownhouse
Taxes:$8,400
Tax Year: 2023
Remarks: Experience elevated waterfront living in this exceptional new construction townhome offering stunning sunset views and direct access to a private marina. Thoughtfully designed with both style and function in mind, the residence features a striking white-oak floating staircase and a private elevator providing seamless access to every level. Soaring tray ceilings with accent lighting, luxury vinyl plank flooring, and an open-concept layout create a bright, modern feel, complemented by expansive balconies that showcase beautiful water views. The chef-inspired kitchen is ideal for entertaining and everyday living with a five-burner gas cooktop, built-in oven and microwave, a large pantry, solid wood shaker cabinetry with pull-out shelving, expansive quartz countertops with a breakfast bar, and a wine refrigerator. The primary suite is a private retreat with its own balcony, dual walk-in closets, and a spa-style ensuite featuring double vanities and a spacious walk-in shower with frameless glass. Water views can be enjoyed from nearly every vantage point, and the rooftop level truly sets this townhome apart, featuring a bonus room and second kitchen, folding glass doors that open to a patio with an Ipe wood deck, and a built-in gas grill with cabinetry, perfect for entertaining or relaxing while enjoying the sunsets. Additional highlights include a two-car garage and a large storage room, all conveniently located just minutes from downtown Dunedin, approximately one mile from the Dunedin Causeway, and about a 20-minute drive to Clearwater Beach, with Tampa and St. Petersburg both roughly 35 minutes away.
Listing is courtesy of: SUNSTAR REAL ESTATE LLC (727-596-8200)
Listing Agent: Taylor Holevas (727-330-4727)
1500 MAPLE ST, CLEARWATER, FL 33755
$1,399,000299 Days on yellowkey MLS ID: TB8429998
Bed: 6 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3850 Built: 1925 Tax: $3,823 (2024)Community: GlenwoodSpa: YesSingle Family
Taxes:$3,823
Elementary School: Skycrest Elementary-PN
Remarks: Live in Resort-Style Luxury While Earning Passive Income! Welcome to paradise in the heart of Clearwater — just 10 minutes from the world-renowned Clearwater Beach, within walking distance to Clearwater Country Club, and in an A-RATED school district. This beautifully updated and income-generating MULTIFAMILY QUADPLEX resort combines timeless elegance with modern upgrades, offering a truly unique blend of residential comfort and business potential. Whether you're looking to live in style while offsetting your mortgage or expand your portfolio with proven 5-star short and long term rental success, this property delivers. Zoned for FIVE UNITS, with the potential of earning over $200,000 in annual rental income, this high-performing asset comes fully furnished and turnkey — ready for immediate occupancy for multigenerational living or continued rental use. Set on a spacious 1/3 acre CORNER LOT, the centerpiece is a 1925 Mediterranean masterpiece bursting with original charm and character. Inside you’ll find terracotta tile floors, original red oak hardwood floors and red oak accents through out, soaring ceilings, 10" baseboards, rope twist door and window molding, a cozy fireplace, natural gas burning appliances, AND an ATTACHED MOTHER IN LAW SUITE WITH A PRIVATE ENTRANCE! The chef-inspired kitchen features a gas range, granite countertops, stainless steel appliances, and ample cabinet space. The primary home features an attached mother in law suite that can either be utilized with main home access or can remain separate to create two units. The other two apartments are located in the detached building adjacent to the pool. Each of the four units on this property boasts private entrances and has been thoughtfully remodeled with modern touches and inviting décor — perfect for vacationers or long-term tenants alike. Step outside to your private oasis: a resort-style pool with a brand new gas heater surrounded by a pavered entertaining deck complete with an outdoor kitchen and bar, brand new $12,000 hot tub, pool table, and a variety of games — ideal for hosting guests or relaxing in style. Additional features include a woodworking shed and storage shed for hobbyists or added storage, a 40-foot parking space for an RV or camper with electrical hookups and water, and fully landscaped grounds offering privacy and charm. This multifunctional property is a rare gem in one of Clearwater’s most desirable locations, nestled within the historic Glenwood neighborhood. Whether you want a luxe home with unmatched character, an income stream, or both — this quadplex is the ultimate lifestyle and investment package.
Listing is courtesy of: COMPASS FLORIDA LLC (305-851-2820)
Listing Agent: Katie Patterson (727-771-5660)
1446 ADMIRAL WOODSON LN, CLEARWATER, FL 33755
$519,00044 Days on yellowkey MLS ID: TB8515872
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 2097 Built: 1958 Tax: $5,194 (2025)Community: Palm TerraceSingle Family
Taxes:$5,194
Elementary School: Kings Highway Elementary-PN
Remarks: Virtually Staged. Welcome to this beautifully renovated 4-bedroom, 2.5-bathroom single-family residence offering 2,097 square feet of modern living space in a quiet, established Clearwater neighborhood with wide streets and a welcoming residential feel. This home features a stunning open-concept layout with a designer kitchen showcasing modern European-style cabinetry, quartz countertops, and a counter-to-ceiling porcelain tile backsplash. Present is a seamless flow into the dining and living areas for effortless entertaining. Modern concrete design ceramic tile flooring runs throughout the entire home, complemented by clean, vibrant interior colors that enhance the bright, contemporary design. The bathrooms have also been tastefully updated with stylish modern finishes The roof was replaced in 2023. The home includes updated windows, adding comfort and efficiency, along with rain gutters installed throughout for added protection. A spacious family/entertainment room with a wet bar creates the perfect setting for gatherings and relaxation. Situated on an expansive 8,303 sq. ft. lot, the property offers ample outdoor space with room to add a pool, while still providing areas for entertaining and outdoor enjoyment. Ideally located just 10 minutes from Clearwater Beach and 10 minutes from Downtown Dunedin, this home offers the perfect balance of modern luxury, comfort, and convenience in one of the most desirable areas of Pinellas County.
Listing Agent: Igli Qirici (727-776-4951)
110 N JUPITER AVE, CLEARWATER, FL 33755
$349,00040 Days on yellowkey MLS ID: O6414604
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1117 Built: 1953 Tax: $3,985 (2025)Community: Sky Crest Unit 1Single Family
Taxes:$3,985
Remarks: Welcome to your charming coastal retreat nestled in the lush foliage of the desirable Sky Crest neighborhood. This beautifully maintained two-bedroom, two-bath home offers the perfect balance of peaceful residential living and convenient access to everything the Clearwater area encompasses. Located just six miles from the beach, you can enjoy relaxing days along the Gulf Coast while still being tucked away from the busy tourist areas, creating a quiet and inviting atmosphere to call home. This home has been thoughtfully updated with significant capital improvements, including a new roof (2025), new insulation (2023), a replaced HVAC system (2023), and a new hot water heater (2024). Additional enhancements include select replacement windows and a beautifully updated kitchen with upgraded cabinetry and granite countertops. As you step inside, you are welcomed by a bright and comfortable layout designed for both everyday living and entertaining. The spacious living room is thoughtfully positioned just off the kitchen, creating a natural flow throughout the home while still maintaining distinct gathering spaces. The kitchen features granite surface countertops, stainless steel appliances, and ample cabinetry, making it both functional and stylish for cooking and hosting guests. Tile flooring runs throughout the home, offering durability, easy maintenance, and a clean coastal feel. The dining area provides generous space for family dinners, holiday gatherings, or casual entertaining with friends. Both bedrooms are comfortably sized, and the two full bathrooms provide convenience and flexibility for homeowners and guests alike. One of the standout features of this property is the screened-in back porch, the perfect place to unwind with your morning coffee or enjoy the evening breeze while taking in the fresh coastal air. Step outside to discover a spacious backyard with endless possibilities. Whether you envision creating a beautiful garden, adding outdoor entertainment space, setting up a workshop area, or simply enjoying the extra room for storage and hobbies, this oversized lot provides the flexibility to make it your own. Conveniently located near shopping, dining, parks, and community amenities, this home combines comfort, location, and opportunity in one inviting package. Whether you are searching for a primary residence, seasonal getaway, or investment opportunity near the beach, this property is full of potential and charm. Do not miss your opportunity to own this quaint beach-area gem in the heart of Sky Crest. Schedule your private showing today and experience the relaxed Florida lifestyle this home brings to the table.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Walter Taylor, Iii (904-716-0670)
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