Location: Sarasota , 34242
Do Not Show Listings
6790 SARASEA CIR #6790, SARASOTA, FL 34242
$675,000214 Days on yellowkey MLS ID: A4671923
REDUCED by $44,900 (6.2%) on 04/12/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1446 Built: 1981 Tax: $5,650 (2025)Community: Midnight SeaCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,650
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Just steps from Point of Rocks Beach! This 3BR/2.5BA townhouse with a garage at 6790 Sarasea Circle offers the best of coastal living in an exclusive 12-residence community. Enjoy direct access to Siesta Key’s world-famous beaches and village. The 1,446 sq. ft. interior features wood flooring, a cozy fireplace, and a screened lanai overlooking the pool. The bright kitchen includes white cabinetry, generous counter space, and a pass-through breakfast bar. Upstairs, 2 inviting bedrooms each feature private balconies, ample closets, and abundant natural light. Bathrooms are thoughtfully designed for comfort and convenience one on each floor, including en-suite and Jack-and-Jill layouts on the third floor. An oversized one-car garage provides direct access to a versatile lower-level bonus space, 3rd bedroom and laundry room. With up to 12 rentals allowed per year, this property offers excellent income potential in a prime island location close to dining, shopping, and downtown Sarasota.
Listing is courtesy of: GOOD LIFE REALTY LLC (941-342-9889)
Listing Agent: Raffilena Hamilton (941-685-2441)
4179 ROBERTS POINT CIR #LOT 17, SARASOTA, FL 34242
$3,400,000233 Days on yellowkey MLS ID: A4669772
Bed: 5 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 3200 Built: 2027 Tax: $5,916 (2024)Community: Roberts Point 2Spa: YesSingle Family
Taxes:$5,916
Tax Year: 2024
Remarks: Pre-Construction. To be built. Brought to you by Noah Thomas Builders, this newly constructed coastal residence inspired by classic West Indies architecture and situated in the exclusive Roberts Point neighborhood on Siesta Key. This thoughtfully designed home pairs timeless island style with modern coastal construction, offering refined living in a highly desirable island setting. Built to meet today’s highest coastal standards, the residence will feature solid concrete block construction, elevated foundation systems, hurricane-impact windows and doors, metal roofing, and other structural elements designed for durability and long-term peace of mind in a waterfront-adjacent environment. The interior layout emphasizes open, airy living spaces with high ceilings with abundant natural light that create an effortless connection to the outdoors. The kitchen is designed as both a functional workspace and gathering area, featuring premium appliances, custom cabinetry, and a generous island ideal for entertaining and everyday living. The primary suite serves as a private retreat with a spa-inspired bathroom, including a freestanding soaking tub, dual vanities, and a spacious walk-in shower. Additional bedrooms offer en-suite baths and refined finishes, while a flexible bonus space allows for a home office, fitness room, or lounge. Outdoor living is a focal point of the design, with covered entertaining areas, an outdoor kitchen, and a resort-style pool and spa—perfect for enjoying Siesta Key’s year-round sunshine and relaxed island atmosphere. Located on the quiet north end of Siesta Key, Roberts Point is known for its privacy, natural surroundings, and convenient proximity to Siesta Beach, Siesta Village, and downtown Sarasota. This new construction home presents a rare opportunity to experience elevated coastal living by Noah Thomas Builders in one of Sarasota’s most coveted island communities. All images, renderings, and descriptions are for illustrative purposes and represent the intended design and style by Noah Thomas Builders. Finishes, materials, and specifications are subject to change during construction. Pricing, availability, and final details may be modified prior to completion.
Listing is courtesy of: 1ST CLASS REAL ESTATE SUNCOAST (386-882-6644)
Listing Agent: Holly Wikfors, Llc (239-777-8075)
927 CONTENTO ST, SARASOTA, FL 34242
$2,300,00051 Days on yellowkey MLS ID: A4691441
0 Days Off yellowkey (back on 4/26/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3649 Built: 2024 Tax: $13,452 (2024)Community: Siesta IslesSpa: YesSingle Family
Taxes:$13,452
Remarks: Short Sale. Partially complete. Interior is mostly complete and needs final punch-out completed and painting.
Listing is courtesy of: REALTY EXECUTIVES GALLERY (941-376-8769)
Listing Agent: Troy Jenkins (941-376-8769)
6146 MIDNIGHT PASS RD #12S, SARASOTA, FL 34242
$1,500,000132 Days on yellowkey MLS ID: A4680754
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1204 Built: 1967 Tax: $11,612 (2025)Community: Island HouseCondo
Taxes:$11,612
Remarks: Best beachfront value on Siesta Key!!! This second-floor condo features two bedrooms and two bathrooms, including a primary ensuite with a king-size bed and a guest bedroom. The interior offers a spacious living area, a formal dining space, and a fully equipped kitchen with granite countertops. Residents and guests can enjoy spectacular views of the Gulf of Mexico and sunsets from the private lanai. The property has recently benefited from refreshed landscaping and updated outdoor furniture. On-site amenities include a year-round heated pool, private beach access with cabanas and lounge chairs provided. A beachfront courtyard with shuffleboard, cornhole, gas grills and shaded seating are ideal for relaxation while watching sunsets. The recreation room offers air hockey, ping pong and more. Located in Island House, well known to be the top rental income producer, this unit is not only a beautiful 2nd home or vacation destination but also a highly valuable, appreciating assest/investment property. While the 2024 and 2025 seasons were impacted by hurricanes resulting in an average rental income of $80,000 a year over the last several years, these units are capable of well over $100,000. With exceptional water views and professional on-site management, this property represents a marriage of functionality, income and beauty.
Listing is courtesy of: BECKMANN REAL ESTATE (941-346-3500)
Listing Agent: Josh Beckmann (941-321-3500)
191 VISTA HERMOSA CIR, SARASOTA, FL 34242
$570,000131 Days on yellowkey MLS ID: A4680721
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 993 Built: 1971Monthly Fee: $1,104 Tax: $4,566 (2025)Community: Vista HermosaVilla
Taxes:$4,566
Remarks: One or more photos have been virtually staged. Welcome to your maintenance free, dream beach retreat on Siesta Key! This charming and meticulously remodeled 2-bedroom, 2-bath villa offers the perfect blend of luxury and convenience, just a short stroll from the pristine sands of Crescent Beach. Enjoy cooking in a stunning kitchen featuring brand new quartz countertops, stainless steel appliances, and stylish light fixtures. Experience comfort year-round with newly installed HVAC and energy-efficient tankless water heater. Luxury vinyl panel floors flows seamlessly throughout, offering both durability and aesthetic appeal. Relax in the attached, screened-in lanai, complete with No-See-Um screen, aluminum framing and a new Hunter, wet-rated ceiling fan, perfect for warm island evenings. Both bathrooms have been beautifully remodeled providing a fresh, contemporary feel. Located just a few steps from the Clubhouse, heated pool, outside grilling areas and laundry facility. Walking distance to shops, restaurants and entertainment. Enjoy the easy, island lifestyle with access to the free trolley service to Siesta Key Village for even more shopping and dining experiences. Ideal for a second home, rental investment, or full-time residence. Don't miss this great opportunity to own a piece of paradise! Schedule your showing today and embrace the Siesta Key lifestyle!
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Denise Barbato (941-400-8773)
157 VISTA HERMOSA CIR, SARASOTA, FL 34242
$569,000141 Days on yellowkey MLS ID: A4677280
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1036 Built: 1971Monthly Fee: $1,041 Tax: $3,568 (2025)Community: Vista HermosaVilla
Taxes:$3,568
Remarks: Completely renovated in 2025, this 2 bedroom/2 bath, maintenance free villa is walking distance to the powdery sands of beautiful Crescent beach on Siesta Key. Great opportunity for a second home, vacation rental or full-time residence. 2-week minimum, 26 times a year rental policy. All kitchen upgrades include new cabinets, quartz countertop, sink and all new stainless steel appliances including, microwave, refrigerator, stovetop and dishwasher. Convenient all new washer and dryer in unit! New tile flooring throughout. Amenities include a renovated clubhouse with full kitchen, heated swimming pool and outdoor grilling areas. This well-managed island retreat is located just a short distance to restaurants, shopping, entertainment and water sports. Enjoy the stress free, beach lifestyle of Siesta Key!
4183 ROBERTS POINT CIR #LOT 18, SARASOTA, FL 34242
$3,400,000234 Days on yellowkey MLS ID: A4669711
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3200 Built: 2027 Tax: $11,511 (2024)Community: Roberts Point 2Spa: YesSingle Family
Taxes:$11,511
Remarks: Pre-Construction. To be built. Joint-Venture opportunity partnering with investors up and down Florida's coast. Brought to you by Noah Thomas Builders — where modern luxury meets timeless coastal elegance. A masterclass in luxury homebuilding, this Noah Thomas Builders contemporary coastal home offers an exceptional blend of modern aesthetics and is built to FEMA's latest standards. Step inside this 3240 sqft home offering four bedrooms, four bathrooms, an open-concept floor plan with high ceilings and premium finishes throughout. It features all hurricane-rated windows and doors and is constructed to be as hurricane and flood-proof as possible-giving you peace of mind while living steps from the water. The kitchen boasts quartz countertops, top-tier appliances, and a spacious island perfect for entertaining. Retreat to the luxurious master suite with spa-inspired bath and expansive walk-in closets. Endless sunshine, gentle breezes, and your own private pool and spa — relax, unwind, and entertain in your personal outdoor oasis. Additional highlights include a private elevator, gas generator and wine room. The rooftop deck, however, defines this residence. This elevated sanctuary invites you to experience Siesta Key from a completely new perspective. Your private escape above it all — a space built for sunsets, sea breezes, and unforgettable gatherings. Situated on the quiet north end of Siesta Key, Roberts Point is prized for its natural beauty, privacy, and proximity to Siesta Beach, Siesta Village, and downtown Sarasota. All images, renderings, and descriptions illustrate the intended design and style by Noah Thomas Builders. Finishes, materials, and specifications may change during the build process. Pricing, availability, and final details subject to adjustment prior to completion.
7324 POINT OF ROCKS RD, SARASOTA, FL 34242
$16,000,000442 Days on yellowkey MLS ID: A4643281
Bed: 5 Bath: 5.0 Gar: 4 Liv Area Sq Ft: 5524 Built: 2025 Tax: $32,550 (2024)Community: White Beach Fruit Co PropSpa: YesSingle Family
Taxes:$32,550
Elementary School: None
High School: None
Middle School: None
Remarks: Newly completed Gulf-front coastal contemporary home on prestigious Siesta Key by Murray Homes. This 5BR/5BA/1HB residence offers approx. 5,500 sq. ft. of living space plus 2,600 sq. ft. of recreational non-conforming space. Features include a gourmet kitchen with large island, walk-in pantry, wine refrigerator, and built-in coffee system, opening to a spacious great room with fireplace. Smart home technology, high-end lighting, and whole-house generator. Outdoor living includes Gulf-front pool and spa with beach shelf, expansive deck, summer kitchen, fireplace, and lounge areas. Upstairs lounge with vaulted wood ceilings and beverage refrigerator, plus 4 en-suite bedrooms, many with Gulf views. Primary suite with soaking tub, oversized shower, and dual vanities. Private beach on a secluded street with panoramic Gulf views. 4-car garage plus golf cart/kayak garage
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Karen Chandler (941-544-4919)
5345 SIESTA CT, SARASOTA, FL 34242
$1,160,00097 Days on yellowkey MLS ID: A4685607
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2272 Built: 1977Monthly Fee: $45 Tax: $5,278 (2025)Community: Siesta Cove SubSingle Family
Taxes:$5,278
Remarks: Welcome to Siesta Cove on Siesta Key, just minutes from world famous Siesta Key Beach. This bright, well maintained home offers comfortable island living in one of the area’s most desirable neighborhoods. The layout provides excellent flexibility with both a living room and a separate family room, giving you plenty of space to relax or entertain guests. Oversized windows throughout the home bring in natural light and offer beautiful views of the mature tropical landscaping, creating an inviting atmosphere. Built in cabinetry and shelving add character to the living room, while the two skylights in the family room bring in beautiful natural light throughout the day. The kitchen offers granite countertops, a large island with seating, and generous cabinet storage. The cabinets are real maple with soft close drawers and doors, crown molding, and lighted glass display cabinets. Additional conveniences include under cabinet lighting and pull out drawers, making storage easy and accessible. The primary suite serves as a comfortable private retreat. It features a large walk in closet with built in organization and an en-suite bathroom with dual vanities, granite countertops, and a spacious tiled shower. After spending the day at Siesta Key Beach, you can rinse off at the outdoor shower before heading inside. Two outdoor living areas allow you to enjoy Florida’s coastal climate: a front entrance lanai and a private lanai off the family room, both ideal for morning coffee or relaxing in the evening. The side load two car garage enhances the home’s curb appeal and provides additional storage space. Several major systems have already been updated. The roof was replaced in 2020, including two skylights. The home also features PVC sewer lines, the air conditioning system was replaced in 2022, and the water heater was replaced in 2023. Best of all, the property experienced no damage during the recent storms, providing additional peace of mind for buyers. This is a wonderful opportunity to enjoy the relaxed lifestyle of Siesta Key, just minutes from the beach, dining, and everything the island has to offer.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Fred Sassen (404-408-5956)
6713 MIDNIGHT PASS RD #4, SARASOTA, FL 34242
$330,000400 Days on yellowkey MLS ID: A4651929
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 598 Built: 1974 Tax: $4,050 (2024)Community: Casa SiestaCondo
Taxes:$4,050
Remarks: BACK ON THE MARKET, FINANCING FELL THROUGH. Looking for your piece of paradise? This fully furnished one-bedroom, one-bath unit is near Siesta Key's stunning beaches. Just bring your clothes and toothbrush. Ideal for snowbirds, investors, or those seeking island life. Conveniently located near the Village of Siesta Key's amenities. Brand new A/C May 2026.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Toni Lyon (941-928-8735)
4646 GLEASON AVE, SARASOTA, FL 34242
$1,350,000159 Days on yellowkey MLS ID: A4677470
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2927 Built: 1957 Tax: $7,816 (2025)Community: Ocean Beach RepSingle Family
Taxes:$7,816
Remarks: Experience the epitome of luxury with this stunning home that defines coastal elegance. Nestled on a quiet island street, this Florida Coastal masterpiece is set on a large 12,805 square foot lot with 75 ft of private lakefront overlooking the serene waters of Lake Norma, on our famed Siesta Key. Renovated with meticulous attention to detail, this newly updated home features an expansive, light-filled open floor plan with continuous quartzite countertops throughout. It includes two primary suites, one of which flows into its own private kitchenette overlooking the tranquil waterfront. Two lanais and a custom built hot tub and pool complete with a waterfall and color-changing lighting system ensure seamless indoor-outdoor living. Quality and craftsmanship are paramount, and every detail has been thoughtfully considered to ensure superior structural integrity, including the hurricane impact windows and elevated AC condensers. A new roof was installed in 2024, along with new mechanicals, electrical, plumbing, pool surfacing, appliances, and more. This gorgeous island paradise has been fully renovated to both preserve and highlight its architectural elegance. A prime location, this property is ideally situated minutes to the world-famous powdery sands of Siesta Key Beach, less than a mile from charming Siesta Key Village, and near the prestigious Out-of-Door Academy. A quick 5-minute drive over the North Bridge takes you to Sarasota proper and a mere 10 minutes more to the heart of dazzling downtown Sarasota and St. Armands Circle, where you can enjoy a wide selection of fine dining, shopping, and world-class cultural arts and nightlife, making it the ideal home for those seeking the ultimate Florida lifestyle. Schedule your private showing today.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Victor Maravi Passara (941-284-3356)
6234 MIDNIGHT PASS RD #307, SARASOTA, FL 34242
$1,100,00046 Days on yellowkey MLS ID: A4692040
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1105 Built: 1979 Tax: $9,703 (2025)Community: Siesta Dunes BeachCondo
Taxes:$9,703
Remarks: Siesta Key offer this Two Bedroom, Two Bath home with Full Views of the Gulf of Mexico. Turnkey furnished. Carport and storage closet. Screened lanai. Weekly rental can give you extra income. Both bedrooms have walk-in closets. Impact windows. You can enjoy the beach chairs and lounges on the famous "White Sand Beach", Gulf front circular pool that is the centerpiece of the community. On-site management. This centrally located community is near shopping and restaurants. It is a short trolley ride to Siesta Key Village.
Listing Agent: Marlene Marshall (941-539-8850)
1215 S PORTOFINO DR #107, SARASOTA, FL 34242
$425,00045 Days on yellowkey MLS ID: A4692252
0 Days Off yellowkey (back on 5/3/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 929 Built: 1968 Tax: $3,442 (2025)Community: Siesta Harbor ISpa: YesCondo
Taxes:$3,442
Remarks: Under contract-accepting backup offers. WATERFRONT SIESTA HARBOR!DIRECT VIEWS OF THE CANAL, walk right out to the canal from your Lanai! BEACH ACCESS ACROSS THE STREET! Turn-Key Furnished with a Canal View! Move in ready, enclosed lanai with all furniture and furnishings included! Highly Sought after remodeled Unit on the Canal in the Dolphin Building! Close to the Resort-style Heated Swimming Pool and Spa on the wide part of the canal. This Charming condo is adorned with large windows, bathing the dwelling in warm, natural light. Combining dining and living space, this turn-key furnished condo is Spacious, light and airy with a Gorgeous updated kitchen with granite countertops! Just move right in or rent until you retire! It's ready for your enjoyment! Active 55+ community, close to the pool, clubhouse, beach access, SCAT, the trolley right outside your door! Beautifully done, tile through out, great coastal feel! TURNKEY FURNISHED! This is a great community lots of activities, fitness room, saunas, outdoor spa, heated pool, on site free laundry, pier on the main intracoastal waterway to relax and fish each day, plus boat slips as available, for a reasonable fee through the Association. The location is wonderful, easy on and off the key, walk to shops, restaurants, mini-donuts! Elevate your living experience in this ready-to-move-in, fully furnished home, and enjoy all the benefits and convenience it offers. Don't miss this chance to reside in one of the best locations in Sarasota; your new home awaits!
Listing is courtesy of: JUDITH GUZZI & ASSOCIATES LLC (914-490-9032)
Listing Agent: Judith Guzzi (914-490-9032)
6005 MIDNIGHT PASS RD #N4, SARASOTA, FL 34242
$799,999155 Days on yellowkey MLS ID: A4677763
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1400 Built: 1966 Tax: $7,741 (2025)Community: Provincial GardensVilla
Taxes:$7,741
Remarks: Perfect Snowbird Getaway! Mid Siesta Key, highly sought after, free-standing villa with it’s own private courtyard front, side and rear. Maintenance Free condo lifestyle that feels like a single family home. Situated in Provincial Gardens on a lushly landscaped and tree canopied street of only 26 units offering old Florida charm. This updated, Turnkey Furnished 2 bedroom + Den, 2 bath offers 1400sf. Spacious owner’s suite features a private patio; wall of closets; and ensuite bath. The updated kitchen offers abundance of cabinets and counterspace & newer appliances. The open floor plan offers tile floors throughout; abundance of sliding glass doors opening to your surrounding private courtyard; Florida room; updated baths; Full Size washer/dryer utility closet; new hot water heater 2023; New roof 2023; & Storage Shed 10x6. The crown jewel of this community is the enormous Bay front park with spacious paver patio where owners and their guests enjoy exquisite sunrises and picturesque sunsets while watching the dolphins, manatees, birds and boaters play in the intracoastal waterway. In addition, there is a new seawall, day dock with canoe/kayak launch, and plenty of room to try your luck at fishing. In addition, owners enjoy deeded beach access; beach chair usage; and jr. Olympic heated pool across the street at the Aloha Kai Community. It is also comforting to note that this community sustained no water damage from any recent hurricanes. This Beach to Bay Retreat is ready as a rental or personal winter getaway for you, your family and friends. This mid-key location is an easy Breeze Bus or Froggy Hop ride to Siesta Key Village; Tennis Courts; Public Beach; Grocery; and abundance of restaurants. Don't delay; these units are rarely available and sell fast.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Linda Starcher, Pa (941-780-2396)
5302 LAS ROSAS, SARASOTA, FL 34242
$725,000321 Days on yellowkey MLS ID: A4659614
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1184 Built: 1962Monthly Fee: $4 Tax: $3,190 (2024)Community: Sarasota BeachSingle Family
Taxes:$3,190
Remarks: Welcome to Palm Island, the Heart of Siesta Key!! Palm Island is an Island on an Island, located a short walk to World Famous Sugery Sands of Siesta Key Beach (Beach Access 10) and Siesta Village. With only one small humpback bridge on & off, this beachy neighborhood is a quiet oasis that is close the beach, restaurants and nightlife that makes this area so desirable. Great opportunity to build your dream home or use the current home as an investment or just enjoy the Island lifestyle. Current home has 2 bedrooms, 2 baths and a 2-car garage. Terrazzo floors throughout. The fenced back yard is a Tropical Paradise for taking in the soothing Gulf Breeze.
Listing Agent: Dan Miller (941-376-7442)
1050 W PEPPERTREE LN #116B, SARASOTA, FL 34242
$669,000103 Days on yellowkey MLS ID: A4684958
0 Days Off yellowkey (back on 5/2/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1083 Built: 1974 Tax: $5,344 (2025)Community: Peppertree Bay IvSpa: NoCondo
Taxes:$5,344
Remarks: Turnkey coastal living on Siesta Key. Beautifully renovated first-floor Gulf-side garden condominium in the highly sought-after Peppertree Bay Gulf-to-Bay community. This exceptional two-bedroom, two-bath residence has been thoughtfully updated throughout and is offered fully turnkey furnished, creating an effortless opportunity to arrive and immediately enjoy the island lifestyle. The bright end-unit layout features a rare windowed kitchen that fills the living space with natural light, a feature seldom found in comparable garden units. The residence has been extensively improved with brand-new hurricane-impact windows, new flooring throughout, and numerous major system upgrades, including a recently replaced HVAC system, hot water heater, and dishwasher, providing peace of mind and reducing future maintenance expenses for the next owner. In addition, there is expanded square footage, enhancing the overall functionality of the home. The enclosed lanai area overlooks a tranquil lagoon and fountain, offering a peaceful setting for morning coffee or evening relaxation. Additional conveniences include a private in-unit washer and dryer, a dedicated exterior storage room, and assigned parking just steps from the entrance. Peppertree Bay is one of Siesta Key’s most desirable waterfront communities, uniquely positioned Gulf-to-Bay and offering a full suite of resort-style amenities that support a true full-service coastal lifestyle. Residents enjoy private beach access with chairs, two heated swimming pools, tennis courts, pickleball courts, a fitness center, fishing pier, newly updated clubhouse, gas grills, and on-site management with rental services. Ideally located just minutes from Siesta Key Village’s restaurants, shopping, and the world-renowned quartz sand beaches, this beautifully updated residence offers a rare combination of turnkey convenience, meaningful capital improvements, expanded living space, and premier coastal location. While the current owners have chosen not to rent the property, Peppertree Bay’s on-site rental management and strong seasonal demand provide an excellent opportunity for owners who wish to generate rental income.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Renee Nadiv (941-299-4242)
5855 MIDNIGHT PASS RD #227, SARASOTA, FL 34242
$499,000151 Days on yellowkey MLS ID: TB8463933
1 Days Off yellowkey (back on 5/2/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1056 Built: 1976 Tax: $4,947 (2025)Community: Harbor Towers Y & RCondo
Taxes:$4,947
Remarks: Under contract-accepting backup offers. Have you been searching for your own slice of tropical paradise on Siesta Key? Look no further than this pet-friendly, 2-bedroom, 2-bathroom residence in the perfectly located Harbor Towers Yacht & Racquet Club. This updated home feels fresh and inviting with new luxury vinyl wood-plank style flooring and brand-new hurricane impact-resistant windows for total peace of mind. Harbor Towers is a well-established community situated right in the heart of "The Key," just across the way from the world-famous Siesta Key Beach and a short distance from vibrant shopping and dining. Life here feels like a permanent vacation with access to a resort-style swimming pool, an oversized hot tub, three Har-Tru tennis courts, a fitness center, and a social room with a catering kitchen. Boaters will especially love the on-site marina, where boat slips are available on a first-come, first-served basis for a nominal monthly hook-up fee. Whether you are looking for a primary residence, a seasonal getaway, or a smart investment with a documented rental history, this hidden gem is ready for you. Come and see what makes this such a special place to live!
Listing is courtesy of: REDFIN CORPORATION (617-458-2883)
Listing Agent: Steven Weiss (845-242-5473)
925 BEACH RD #310, SARASOTA, FL 34242
$599,000288 Days on yellowkey MLS ID: TB8422646
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 753 Built: 1972Monthly Fee: $908 Tax: $5,378 (2024)Community: La SiestaCondo
Taxes:$5,378
Remarks: Siesta Key 2BR/1BA condo updated in 2021 with sweeping Gulf views from a private balcony. Bright, open living area flows to the outdoors. Prime island location close to dining and shops. A standout coastal retreat or investment. Come enjoy the Siesta Key lifestyle!
Listing is courtesy of: BRICK STREET REALTY (727-512-6615)
Listing Agent: Colin Mooney (727-512-6615)
618 AVENIDA DE MAYO, SARASOTA, FL 34242
$1,200,00046 Days on yellowkey MLS ID: A4692001
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 2961 Built: 1948 Tax: $8,283 (2025)Community: Sarasota BeachSingle Family
Taxes:$8,283
Remarks: This Charming Old 1948 Bungalow located just 3 Blocks behind Siesta Key Village and 4 Blocks to Siesta Key Beach!! It is quite the Interesting Property! It was converted into a Triplex many moons ago. It can easily be converted back to a single family residence. Currently, there are 2 Beds and 2 Baths downstairs and 2 Beds 1 Bath upstairs. There are 3 Kitchens, 3 Liv Areas 2 down, 1 up and there is a Bonus Rm down as well as a Screened in Patio on the front West side of the Home, an Open Patio on the East Side and a Closed in Upstairs. And, there's more... At the Rear of the Property is a Cottage, perfect for a Mother In Law Suite or Rental. It is a 1/1 with a full Kitchen and Liv Area. The grounds are Etherical, as there are private little Sitting Areas for each sector and in the center of the Backyard there is a Wash House for Laundry as well as an attached Storage Shed for Gardening. There are additional Outside Storage Units for each of the apartments, again, really a cool old school house with so much to offer. Make it back into a single family or keep it the way it is and rent the house and utilize the cottage for a personal vacay spot! Questions, call me!!
Listing is courtesy of: BLAKELEY & ASSOCIATES REALTY (941-567-3100)
Listing Agent: Lisa Blakeley (941-809-1647)
6512 MIDNIGHT PASS RD #303, SARASOTA, FL 34242
$2,190,000400 Days on yellowkey MLS ID: A4652317
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1763 Built: 2006 Tax: $19,644 (2024)Community: Crescent Siesta KeyCondo
Taxes:$19,644
Remarks: Welcome to luxurious, maintenance-free beachfront living at prestigious Crescent Siesta Key Condominiums. This 1,800-square-foot turnkey-furnished unit offers three bedrooms, two full baths, a laundry room and two large balconies, one with beach views, and the other overlooking the second-level Crescent pool/courtyard. The inviting open floor plan includes a large dining room. The kitchen is open to the dining room and living room. Poggenpohl (luxury German-made) cabinets, stainless appliances, large breakfast bar and spacious pantry/storage cabinets line the hallway. It is near south Siesta Key Bridge with shopping, entertainment and dining across the street. The Crescent is a boutique complex of only 26 units and offers direct beach access, a gulf-view pool with whirlpool hot tub, as well as a single-lane lap pool, a gourmet poolside summer kitchen and a beautifully landscaped garden terrace with poolside seating. It includes well-appointed common areas, elevators to all floors, a clubhouse, a fitness room, reserved two-car covered parking, a car charging station, on-site manager and 24-hour video surveillance with common areas secured by keypad access. It is a pet-friendly community for owners only. Investors alert! The unit is on the vacation rental program with Beachside Management, and it attracts lots of bookings. This is must-see.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Ziad Sleit (941-928-5493)
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