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Thoughtfully restored and filled with character, this Southside bungalow pairs timeless charm with extensive modern updates, including impact windows, on a generous 75-by-143-foot lot. A private walled courtyard with brick pavers and tropical landscaping creates a welcoming entrance, while refinished oak floors, Venetian plaster walls and crown molding bring warmth and distinction to the bright, open interior. The living areas feature walls of windows, allowing abundant natural light and beautiful views of the lush outdoor foliage. The kitchen underwent a complete renovation down to the studs and features white shaker cabinetry, high-end appliances, designer hardware and fixtures, and new oak flooring. A renovated bathroom, fresh interior and exterior paint, updated trim and lighting, new gutters, HVAC and water heater add to the home’s move-in-ready appeal. Additional improvements include linen shades, an owned security system with cameras, and new landscaping. The spacious lot offers ample room for a future pool and opportunities to expand the outdoor living space. Within walking distance of downtown Sarasota and Southside Village’s shops and restaurants, this beautifully maintained residence offers an appealing alternative to condominium living, with the privacy and flexibility of a single-family home. Enjoy charm, convenience and room to grow in one of Sarasota’s most sought-after locations.

2 Beds ⋅ 2 Baths ⋅ Hudson Bayou SubDv. ⋅ 34239 Zip Code

Thoughtfully restored and filled with character, this Southside bungalow pairs timeless charm with extensive modern updates, including impact windows, on a generous 75-by-143-foot lot. A private walled courtyard with brick pavers and tropical landscaping creates a welcoming entrance, while refinished oak floors, Venetian plaster walls and crown molding bring warmth and distinction to the bright, open interior. The living areas feature walls of windows, allowing abundant natural light and beautiful views of the lush outdoor foliage. The kitchen underwent a complete renovation down to the studs and features white shaker cabinetry, high-end appliances, designer hardware and fixtures, and new oak flooring. A renovated bathroom, fresh interior and exterior paint, updated trim and lighting, new gutters, HVAC and water heater add to the home’s move-in-ready appeal. Additional improvements include linen shades, an owned security system with cameras, and new landscaping. The spacious lot offers ample room for a future pool and opportunities to expand the outdoor living space. Within walking distance of downtown Sarasota and Southside Village’s shops and restaurants, this beautifully maintained residence offers an appealing alternative to condominium living, with the privacy and flexibility of a single-family home. Enjoy charm, convenience and room to grow in one of Sarasota’s most sought-after locations.

1747 Waldemere Street, Sarasota

$1,395,000

FULLY FURNISHED SHORT TERM RENTAL PROPERTY. Experience the best of "West of Trail" living in this impeccably maintained, renovated pool home situated on an OVERSIZED LOT. The interior features include refinished HARDWOOD FLOORS, double-paned windows, and an UPDATED KITCHEN equipped with custom cabinetry, granite countertops, and stainless-steel appliances. The inviting main living area is highlighted by a tray ceiling, gas fireplace and French doors leading to a private outdoor area and SALTWATER POOL, perfect for the Florida lifestyle. The fully FENCED professionally landscaped yard includes a PUTTING GREEN. Significant improvements offer peace of mind and long-term value, including a new standing seam METAL ROOF (2025), NEWER A/C system (2022)/mini-split (2024), and completely REPLUMBED with PVC. The air-conditioned TWO-CAR GARAGE features new epoxy flooring and is currently utilized as a versatile game room. Ideally located in the sought-after Southside Elementary district, this residence provides quick access to Southside Village, downtown Sarasota, and the renowned beaches of Siesta and Lido Key. This property has a great rental history with $85,000 in 2026 plus future bookings in 2027 so the new owner will have positive cash flow immediately. Inquire for more details.

3 Beds ⋅ 2 Baths ⋅ Hudson Bayou SubDv. ⋅ 34236 Zip Code

FULLY FURNISHED SHORT TERM RENTAL PROPERTY. Experience the best of "West of Trail" living in this impeccably maintained, renovated pool home situated on an OVERSIZED LOT. The interior features include refinished HARDWOOD FLOORS, double-paned windows, and an UPDATED KITCHEN equipped with custom cabinetry, granite countertops, and stainless-steel appliances. The inviting main living area is highlighted by a tray ceiling, gas fireplace and French doors leading to a private outdoor area and SALTWATER POOL, perfect for the Florida lifestyle. The fully FENCED professionally landscaped yard includes a PUTTING GREEN. Significant improvements offer peace of mind and long-term value, including a new standing seam METAL ROOF (2025), NEWER A/C system (2022)/mini-split (2024), and completely REPLUMBED with PVC. The air-conditioned TWO-CAR GARAGE features new epoxy flooring and is currently utilized as a versatile game room. Ideally located in the sought-after Southside Elementary district, this residence provides quick access to Southside Village, downtown Sarasota, and the renowned beaches of Siesta and Lido Key. This property has a great rental history with $85,000 in 2026 plus future bookings in 2027 so the new owner will have positive cash flow immediately. Inquire for more details.

1931 High Point Circle, Sarasota

$975,000

Virtually Staged. Welcome to Cleary Cottage, a charming 1935 bungalow nestled in the highly sought-after Hudson Bayou neighborhood, West of Trail in the heart of Sarasota. Blending timeless character with thoughtful modern updates, this beautifully maintained 3-bedroom, 2-bath residence offers an inviting retreat just minutes from downtown Sarasota, Southside Village, Sarasota Memorial Hospital, Selby Gardens, the bayfront, and the area's renowned beaches. From the moment you arrive, the lush tropical landscaping, circular driveway, and welcoming screened front porch set the tone for this distinctive home. Inside, original hardwood floors, plaster walls, crown molding, and a classic brick fireplace celebrate the home's historic charm, while an updated kitchen featuring white cabinetry, stone-look countertops, stainless steel appliances, and tasteful finishes provides modern convenience. The comfortable floor plan offers inviting living and dining spaces, three bedrooms, and two updated bathrooms, including a primary bath with a beautifully tiled walk-in shower. A metal roof installed in 2018, an updated HVAC system, and hurricane protection improvements add to the home's appeal. Step outside to discover a private tropical oasis with mature landscaping, a backyard deck, and inviting outdoor spaces ideal for relaxing, entertaining, or enjoying Sarasota's year-round sunshine. The spacious screened front porch, complete with a charming porch swing, offers yet another place to unwind and enjoy the neighborhood. Located in FEMA Flood Zone X, this property offers the added advantage of being outside the designated high-risk flood area. Its location and zoning also create an attractive short-term rental opportunity, offering flexibility for buyers considering seasonal use, part-time occupancy, or income-producing potential. Whether you're searching for a full-time residence, seasonal escape, or a Sarasota property with flexible rental potential, Cleary Cottage delivers a special combination of character, comfort, and location. Experience the charm of Old Florida living with the conveniences of Sarasota's vibrant downtown, shopping, dining, cultural attractions, and world-famous Gulf Coast beaches close by. Schedule your private showing and discover what makes Cleary Cottage so special!

3 Beds ⋅ 2 Baths ⋅ Hudson Bayou SubDv. ⋅ 34236 Zip Code

Virtually Staged. Welcome to Cleary Cottage, a charming 1935 bungalow nestled in the highly sought-after Hudson Bayou neighborhood, West of Trail in the heart of Sarasota. Blending timeless character with thoughtful modern updates, this beautifully maintained 3-bedroom, 2-bath residence offers an inviting retreat just minutes from downtown Sarasota, Southside Village, Sarasota Memorial Hospital, Selby Gardens, the bayfront, and the area's renowned beaches. From the moment you arrive, the lush tropical landscaping, circular driveway, and welcoming screened front porch set the tone for this distinctive home. Inside, original hardwood floors, plaster walls, crown molding, and a classic brick fireplace celebrate the home's historic charm, while an updated kitchen featuring white cabinetry, stone-look countertops, stainless steel appliances, and tasteful finishes provides modern convenience. The comfortable floor plan offers inviting living and dining spaces, three bedrooms, and two updated bathrooms, including a primary bath with a beautifully tiled walk-in shower. A metal roof installed in 2018, an updated HVAC system, and hurricane protection improvements add to the home's appeal. Step outside to discover a private tropical oasis with mature landscaping, a backyard deck, and inviting outdoor spaces ideal for relaxing, entertaining, or enjoying Sarasota's year-round sunshine. The spacious screened front porch, complete with a charming porch swing, offers yet another place to unwind and enjoy the neighborhood. Located in FEMA Flood Zone X, this property offers the added advantage of being outside the designated high-risk flood area. Its location and zoning also create an attractive short-term rental opportunity, offering flexibility for buyers considering seasonal use, part-time occupancy, or income-producing potential. Whether you're searching for a full-time residence, seasonal escape, or a Sarasota property with flexible rental potential, Cleary Cottage delivers a special combination of character, comfort, and location. Experience the charm of Old Florida living with the conveniences of Sarasota's vibrant downtown, shopping, dining, cultural attractions, and world-famous Gulf Coast beaches close by. Schedule your private showing and discover what makes Cleary Cottage so special!

1777 Alta Vista Street, Sarasota

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