Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
6204 MIDNIGHT PASS RD #205, SARASOTA, FL 34242
$775,000103 Days on yellowkey MLS ID: A4676979
REDUCED by $4,000 (0.5%) on 04/12/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1173 Built: 1979Monthly Fee: $1,243 Tax: $6,173 (2025)Community: Siesta Dunes BeachCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,173
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Welcome to your slice of paradise at Siesta Dunes Beach Community. This beautifully maintained 2-bedroom, 2-bath end-unit is located on the second floor and is offered turnkey furnished, making it ideal as a vacation getaway, investment property, or full-time residence. Being an end unit, the condo is filled with extra natural light and offers a charming peek-a-boo ocean view to remind you just how close you are to the beach. Enjoy peace of mind with recent upgrades, including a newer AC, newer roof, and brand-new impact windows (2025). The unit includes a covered parking space and the community provides private beach access and beach chairs, so you’re ready to enjoy the Siesta Key lifestyle from day one. With weekly rentals allowed, this property offers excellent rental potential in a highly desirable beachfront community. Whether you’re relaxing on the sand or generating income, this Siesta Dunes condo checks all the boxes for coastal living which will not disappoint.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Christine Green (941-914-2463)
4817 OCEAN BLVD, SARASOTA, FL 34242
$1,949,000163 Days on yellowkey MLS ID: A4671593
1 Days Off yellowkey (back on 4/12/2026)
REDUCED by $46,000 (2.3%) on 04/07/2026
Bed: 4 Bath: 3.0 Gar: 5 Liv Area Sq Ft: 2657 Built: 1982 Tax: $8,709 (2025)Community: Lake RittwoodSpa: YesSingle Family
Taxes:$8,709
Remarks: Under contract-accepting backup offers. Welcome to 4817 Ocean Blvd – Your Private Lakefront Escape in the Heart of Siesta Key Set on a tranquil spring-fed lake just moments from Siesta Beach and the Village, this flood resilient and meticulously maintained coastal residence offers year-round enjoyment or the perfect lock-and-leave retreat. Elevated and thoughtfully updated, it blends timeless coastal style with exceptional quality and peace of mind. Inside, an open layout showcases engineered oak hardwood floors, solid maple cabinetry, Santorini quartzite countertops, and Thermador appliances. The primary suite features serene lake views and a spa-inspired bath wrapped in Calacatta Oro tile. Outdoors, enjoy a heated saltwater pool, Hot Springs spa, and Tiki Hut with lighting, TV, and sound — perfect for entertaining. The maintenance-free backyard, astro turf lawn, and SWAT mosquito misting system ensure comfort and convenience year- round. A true standout, the air-conditioned 5-car garage with lifts, compressor, and 200mph- rated doors is a car enthusiast’s dream. With a 2019 roof, impact windows and doors, natural gas utilities, and smart home features, this home delivers effortless coastal luxury. Whether as a full-time residence or a seasonal escape, 4817 Ocean Blvd delivers a lifestyle that is uniquely Siesta Key — coastal elegance, lakefront tranquility, superior craftsmanship, and the freedom to simply lock, leave, and enjoy.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Gerard Healy (941-961-2240)
5436 S LOCKWOOD RIDGE RD, SARASOTA, FL 34231
$350,000Listed 04/22/2026 9:51AM MLS ID: TB8495570
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1484 Built: 1968 Tax: $1,903 (2025)Community: Sun HavenSingle Family
Taxes:$1,903
Elementary School: Gulf Gate Elementary
High School: Riverview High
Remarks: You found it! A home that blends comfort, functionality, and Florida-style outdoor living—all with the freedom of NO HOA! This beautifully maintained single-family residence invites you in with a charming curb appeal featuring coach lights, gutters, and a decorative tile entryway that sets the tone from the moment you arrive. Enjoy the convenience of keyless entry and a thoughtfully designed garage with a side door to the exterior, perfect for easy access and added flexibility. Inside you’ll find a spacious, light-filled layout where everyday living and entertaining come together effortlessly. The living room is anchored by a custom media center, creating the perfect space for relaxing nights or hosting guests. The kitchen is both practical and inviting, offering an eat-in area, a separate dining space, and a unique pass-through serving window to the patio—ideal for seamless indoor-outdoor entertaining. Slide open multiple glass doors and step out to your private backyard oasis overlooking a tranquil pond view. Whether you’re enjoying your morning coffee, hosting a barbecue on the extended concrete slab, or soaking up the Florida sunshine, this outdoor space is designed to impress. Inside you’ll also find spacious guest bedrooms, each offering comfort and versatility, along with multiple double-door closets throughout the home—providing an abundance of storage options. Ceiling fans enhance comfort year-round, while hurricane shutters add peace of mind during storm season. This home truly checks all the boxes: VALUE, space, and smart features—all in a serene setting with no HOA restrictions. Seller offering a home warranty with approved offer …or add some updates to your own preference!
Listing is courtesy of: KEY TO FLORIDA REALTY (239-776-9260)
Listing Agent: Rhonda Ryals (813-368-6759)
3363 CROSS CREEK DR #3363, SARASOTA, FL 34231
$279,00083 Days on yellowkey MLS ID: A4680117
REDUCED by $10,000 (3.5%) on 04/22/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1027 Built: 1984Monthly Fee: $632 Tax: $2,727 (2025)Community: Crooked Creek Sec 7Condo
Taxes:$2,727
Elementary School: Wilkinson Elementary
Remarks: Welcome to Crooked Creek, a hidden gem in Sarasota with its own private gated access to the Red Bug Slough Preserve. This beautifully maintained 2-bedroom, 2-bath 2nd floor residence was completely updated in 2021 and offers serene views of Crooked Creek, a charming wooden bridge, and lush park-like surroundings. The open and airy floor plan features hardwood floors and tile throughout, plantation shutters, a skylight at entry, and modern finishes. The updated kitchen includes white cabinetry, solid surface countertops with a large peninsula, tile backsplash, smart stainless steel appliances ( fridge and dishwasher 2025, oven and microwave 2021), a spacious pantry, and a garden window. Additional updates are water heater 2018, and reverse osmosis for kitchen sink 2025. The primary suite enjoys peaceful water, a walk-in closet, linen closet and sliding doors to a covered screened lanai. The updated bath has a washer/ dryer (2021)in separate laundry closet, as well as tile floors, a modern vanity, and tile shower . The guest bedroom offers flexible use with a built-in workstation and queen-size Murphy bed. Additional features include two screened covered lanais, reverse osmosis water system for kitchen sink, covered carport, and ample guest parking. Crooked Creek is a 78-unit community offering a heated resurfaced pool, updated poolside kitchen, gazebo with seating, gas and charcoal grills, tennis/pickleball court, community storage with individual lockers, newer roofs (2021), new carports, and recently painted buildings. HOA fees have been reduced by $69 per month from 2025, reflecting strong reserves and excellent financial management. Conveniently located minutes from Siesta Key Beach, Gulf Gate, downtown Sarasota, shopping, and dining. A true nature lover’s paradise.
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Phyllis Coviello (941-408-3265)
3165 REGATTA CIR, SARASOTA, FL 34231
$485,00054 Days on yellowkey MLS ID: A4683961
REDUCED by $14,000 (2.8%) on 04/19/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1193 Built: 1964Monthly Fee: $6 Tax: $3,638 (2025)Community: Gulf GateSingle Family
Taxes:$3,638
Remarks: Completely remodeled with all work permitted and completed to the highest standards, this move-in ready Gulf Gate home lives large and showcases exceptional quality, thoughtful design, and true craftsmanship. Live where others vacation — perfectly positioned just 2.4 miles from the nearest Siesta Key beach access, placing world-renowned white sand beaches and breathtaking Gulf sunsets just minutes from your doorstep! The designer-curated kitchen features solid wood white shaker cabinetry, premium quartz countertops, a custom tile backsplash, and new stainless-steel appliances. Just off the kitchen, a spacious dining area is anchored by a beautifully crafted custom solid wood banquette with an integrated bookcase, bench seating, and built-in storage — a rare and functional design feature. Both full bathrooms have been beautifully renovated with new vanities, updated countertops, and custom tiled showers. Additional interior upgrades include new luxury vinyl plank flooring, fresh interior and exterior paint, new doors and trim, and updated lighting & fixtures. Indoor laundry adds everyday convenience. Major system improvements provide peace of mind, including new PVC underground sewer drain lines, new water lines, a new water heater, updated electrical panel, HVAC (2020), and a *BRAND NEW ROOF* (2026)! All windows are equipped with hurricane shutters. Designed for seamless indoor/outdoor living, multiple sliding glass doors open to a spacious screened and covered back porch featuring upgraded Trex decking — the perfect space for morning coffee or relaxed evenings under the twinkle lights. The backyard is truly special, highlighted by a custom PAVER FIRE PIT with built-in bench seating. Enjoy fresh landscaping, a new front paver walkway, and a large fenced backyard. Covered carport parking includes an outdoor storage closet, plus an additional shell parking space which provides plenty of parking. Centrally located on a quiet circle in prime Gulf Gate, this home offers easy access to world-famous Siesta Key Beach and is within walking or biking distance to an array of local restaurants and shopping in Gulf Gate. Publix, Trader Joe’s and Costco are all just minutes away, and Gulf Gate Elementary School is right around the corner. Solid short-term rental history available upon request. Turnkey furnishing option is also available which could make for an easy second home and/or Airbnb. Bright, cheerful, and beautifully finished — this home is truly move-in ready! Buyer’s agent to verify all MLS information including room sizes, utilities and HOA if applicable.
Listing is courtesy of: CARMEL PROPERTIES (941-416-6300)
Listing Agent: Jonah Wright (941-932-1661)
1552 STICKNEY POINT RD #403, SARASOTA, FL 34231
$695,000468 Days on yellowkey MLS ID: A4634781
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1270 Built: 1982Monthly Fee: $1,007 Tax: $4,591 (2024)Community: The BoatyardSpa: NoCondo
Taxes:$4,591
Tax Year: 2024
Remarks: The Boatyard is a New England styled gated community of twenty one units located on the Intracoastal Waterway just across the south bridge from Siesta Key and its number one rated beach. Nearby are numerous opportunities for the shopping, dining, sports, and cultural activies that Sarasota is famous for. This furnished two bedroom, two bath unit features water views from most rooms, a bright open concept living/dining room with a tray ceiling and wood burning fireplace, an enclosed balcony overlooking a canal, updated kitchen and bathrooms, an oversized one car garage, and a ground level bonus room off the canal. In addition, the community amenities include a sundeck on the intracoastal waterway, a boardwalk along the canal, and a heated swimming pool. This is the Florida lifestyle you've been looking for.
Listing is courtesy of: ALAN J STEVENS (941-925-1818)
Listing Agent: Murphy Stevens (941-925-1818)
225 HOURGLASS WAY #202, SARASOTA, FL 34242
$510,00013 Days on yellowkey MLS ID: A4689015
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1271 Built: 1969Monthly Fee: $1,566 Tax: $5,016 (2025)Community: Whispering SandsCondo
Taxes:$5,016
Remarks: Discover elevated, light-filled coastal living in this beautifully updated 2nd floor residence in the premiere Gulf front property of Whispering Sands! Offered completely TURNKEY FURNISHED. The wonderful OPEN CONCEPT layout flows seamlessly from the kitchen, living and dining spaces into your own private, 34’ south facing lanai—perfect for enjoying sunny mornings, gentle breezes, and relaxed indoor-outdoor living year round. As a bonus, this is a highly desirable end unit, with a wonderful extra window in the living space that invites in abundant natural light, enhancing the open, airy feel throughout. Designed for both style and function, the beautifully REMODELED, kitchen features sleek stone countertops, soothing neutral tile backsplash, an 8’ breakfast bar with seating for 4, stainless Frigidaire and Samsung appliances, soft close cabinetry, and wonderful overhead recessed lighting. Both bathrooms have been tastefully updated with stone counters, while the primary suite offers a private ensuite bath and a walk-in closet for comfortable everyday living. Equally spacious, the guest bedroom is large enough to accommodate two queen beds. Nestled on the westernmost point of Siesta Key, Whispering Sands is a highly desirable 55+ Gulf front community offering resort style living – all ideally just moments away from the colorful boutiques, dining options, and charm of world famous Siesta Key Village. The complex offers 800’ of PRIVATE quartz sand beach on the sparkling Gulf, 2 heated pools, new beachside grills and Tiki Hut, shuffleboard, and canoe/kayak storage, The main clubhouse – just steps from this unit - is currently undergoing complete remodeling and upon completion will include fitness rooms, a full catering kitchen, large screen TV, and an elegant, comfortable space for social events or private entertaining. Effortless island living starts here. Don’t miss this opportunity to own this move-in ready, coastal escape in an exceptional island setting!
Listing Agent: Harriet Stopher (404-316-8944)
1200 E PEPPERTREE LN #307, SARASOTA, FL 34242
$669,00054 Days on yellowkey MLS ID: A4683608
REDUCED by $30,000 (4.3%) on 04/20/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1466 Built: 1973 Tax: $7,547 (2025)Community: Peppertree Bay IiCondo
Taxes:$7,547
Remarks: Set within Peppertree Bay on Siesta Key, 1200 E Peppertree Lane #307 offers a well-proportioned, turnkey, move-in ready two-bedroom, two-bath residence encompassing 1,466 square feet. The interior presents a bright, open layout anchored by a spacious great room, where crown molding, tile flooring throughout, and an expansive wall of impact glass windows create an airy, light-filled living environment. The adjoining dining area flows seamlessly into the kitchen, reinforcing the home’s functional, connected design. The kitchen features a tray ceiling with inner crown molding, recessed lighting, abundant wood cabinetry, granite countertops, a tile backsplash, and a full suite of stainless-steel newer Whirlpool appliances. A breakfast bar provides additional prep and serving space, supporting both everyday living and casual entertaining. The primary bedroom is generously scaled and benefits from strong natural light, crown molding, a walk-in closet, and direct access to the enclosed sunroom. The primary bath includes a granite-topped vanity, glass-enclosed walk-in shower, linen storage, and updated fixtures. A well-sized guest bedroom with an oversized window alcove and a nearby full bath maintains privacy and flexibility for visitors. An enclosed sunroom lined with windows extends the living space, offering versatility as a lounge, office, or secondary sitting area. A stacked washer and dryer are conveniently positioned within a dedicated closet. Newer HVAC system (2024) and Water heater (2025). Peppertree Bay is a Gulf-to-Bay community providing private deeded beach access, a fishing pier, two resort-style heated pools, clubhouses, a fitness center, saunas, tennis and pickleball courts, covered under building assigned parking with this unit that provides a bicycle rack and unit storage, and multiple outdoor gathering areas. This building has newer elevators along with stairwell access, with the building roof being replaced in 2020. The location places residents directly on Siesta Key, home to Siesta Beach, consistently ranked the #1 beach in the United States by TripAdvisor, further underscoring the appeal of both the setting and lifestyle offered by this residence.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Sharon Chiodi (941-809-0380)
3515 LA PALOMA AVE, SARASOTA, FL 34242
$1,800,00014 Days on yellowkey MLS ID: A4689037
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2233 Built: 1985 Tax: $15,834 (2025)Community: Siesta Rev OfSpa: YesSingle Family
Taxes:$15,834
Remarks: Elevated Coastal Living Meets TURNKEY Income on Siesta Key Welcome to 3515 La Paloma Ave, a fully reimagined coastal retreat located within the city limits on the north end of Siesta Key, offering luxury living with strong short-term rental potential. Perfectly positioned just minutes from multiple beach accesses and just steps from Beach Access #1 on Shell Rd. along Big Pass this property delivers effortless access to the sand and water, while also offering convenient access on and off the island to the Sarasota mainland. Situated in a prime North Siesta Key location with a strong weekly rental history, this home presents a rare opportunity to blend lifestyle and income in one of the most desirable coastal markets in the country. This high-elevation property provides added peace of mind with no history of flood damage or water intrusion, while still being close to everything that makes Siesta Key so sought after, including Siesta Key Village and the world-famous Siesta Key Beach. The main residence features 4 bedrooms, 3 bathrooms, and just under 2,300 square feet of living space, fully renovated with high-end finishes and a light, modern coastal design. Throughout the home, you’ll find Miami-inspired designer tile work that adds a unique, boutique feel rarely seen in the area. Step outside into your private courtyard-style backyard oasis, where indoor-outdoor living takes center stage. Enjoy a screened pool and spa, a custom waterfall feature flowing into the pool, and a fully equipped outdoor kitchen with a nearby outdoor shower all just steps from the main living areas. What truly sets this property apart is the private guest residence a 2-bedroom, 1-bath suite with its own entrance and a stylish dry bar. Currently producing strong income, this space is ideal for short-term rentals, guests, or multigenerational living. Whether you’re in the main home or guest residence, the layout creates seamless access to your backyard retreat, offering privacy, flexibility, and a true resort-style experience. Live the Siesta Key lifestyle while generating income all from a high-and-dry, designer-finished coastal compound in one of the most sought-after locations on the island.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Derek Edwards (941-929-3183)
1934 DATURA ST, SARASOTA, FL 34239
$1,600,00079 Days on yellowkey MLS ID: A4680304
REDUCED by $25,000 (1.5%) on 04/22/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3091 Built: 2002 Tax: $9,130 (2025)Community: Desota ParkSingle Family
Taxes:$9,130
Elementary School: Southside Elementary
Remarks: A striking residence on one of Sarasota's treasured streets West of Trail, crowned with a NEW BARREL STYLE METAL ROOF, showcasing a raised front porch and grand double-door entry, all enveloped by a lush, resort-style tropical garden. This expansive home just freshly painted and professionally staged, offers four generously sized bedrooms, one boasting it's own large patio in the treetops. With over 3,000 square feet of thoughtfully designed living space, the home blends timeless elegance with comfort, creating an inviting setting for upscale entertaining and everyday living. Be welcomed by a grand two-story vaulted living and dining space, highlighted by an elegant curved staircase and open catwalk above. The spacious chef’s kitchen features a center island and breakfast bar, flowing seamlessly into the family room and through expansive sliding glass doors to a screened patio that evokes the feel of a private tropical paradise. The primary suite is conveniently on the main level, offering soaring ceilings and direct access to the patio. It includes a custom walk-in closet and a spa-inspired bath with dual vanities, a garden tub and a separate shower. Recent updates include NEW CARPETING IN ALL BEDROOMS, NEWER DUAL ZONED AIR CONDINTIONG SYSTEMS for optimal comfort, a NEW HOT WATER TANK and a COMPLETE WHOLE HOUSE RE-PLUMB, offering peace of mind and modern efficiency. ROOM FOR A POOL. Just steps away from Morton's Market, Veronica's, and other neighborhood favorites. Located in the highly regarded Southside Elementary School district, the home offers the very best of the West of Trail lifestyle, walkable to restaurants, boutiques shops, Sarasota Memorial Hospital, with easy access to downtown Sarasota and our world-famous beaches.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-907-9541)
Listing Agent: Christine Mazur (941-374-4015)
6281 MIDNIGHT PASS RD #6281, SARASOTA, FL 34242
$1,195,000264 Days on yellowkey MLS ID: A4654454
0 Days Off yellowkey (back on 4/22/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1770 Built: 1981 Tax: $12,490 (2024)Community: Excelsior Beach To Bay 4Condo
Taxes:$12,490
Remarks: Under contract-accepting backup offers. Investment opportunity with strong rental potential—this Siesta Key waterfront villa offers two-week minimum rentals, private deeded beach access, and an oversized private 2-car garage, an exceptionally rare combination. Located in Excelsior Beach to Bay, this updated 2-bedroom, 2-bath residence is set directly on the Intracoastal Waterway and elevated above its garage, capturing panoramic bay views from nearly every room. The fully furnished, light-filled home features an open floor plan, floor-to-ceiling hurricane-impact glass doors, tile flooring throughout, a remodeled kitchen with white cabinetry and stainless appliances, and a dry bar for easy entertaining. The primary suite enjoys sweeping water views. Recent updates include a new HVAC system and water heater (2024). Store your kayak right under the building for easy access to launching your boat. This community offers convenient access to the south bridge, placing Sarasota's dining, shopping, cultural venues, and medical services just minutes away. This Villa offers the best of coastal living. This pet-friendly, resort-style community offers pools, tennis and pickleball courts, a fitness center, fishing pier, and private deeded access to Siesta Key Beach. Ideally located near the South Bridge with quick access to Sarasota dining, shopping, and culture—making it equally well suited as a luxury vacation rental, seasonal income property, or personal waterfront retreat.
Listing Agent: Jackie De Manio Eberley (201-233-1959)
3541 WILKINSON WOODS DR #40, SARASOTA, FL 34231
$289,900155 Days on yellowkey MLS ID: A4672490
REDUCED by $5,000 (1.7%) on 04/20/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1548 Built: 1980 Tax: $3,658 (2025)Community: Wilkinson WoodsVilla
Taxes:$3,658
Remarks: One or more photo(s) has been virtually staged. Skip the renovation stress and discover an UNBEATABLE VALUE in this updated 2-bedroom, 2-bath attached villa, offering IMPACT WINDOWS, New A/C (2026) and NEWER APPLIANCES. Bathed in natural light, this home features elegant QUARTZ COUNTERTOPS throughout, designer LED-illuminated mirrors, and sleek, durable laminate flooring. Beyond the stylish interior lies a charming paver patio—a relaxing retreat for morning coffee or sunset breezes. Located in an enclave that feels like a hidden secret in South Sarasota, you are minutes from Siesta Key’s white sands, casual and world-class dining, entertainment...but miles from the stress of a fixer-upper. Experience just how effortless Florida living can be by taking this stylish, move-in-ready villa off your screen and scheduling your in-person tour today!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Elisa Gersman (941-735-0595)
5800 TIDEWOOD AVE, SARASOTA, FL 34231
$3,149,000216 Days on yellowkey MLS ID: A4664806
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 5167 Built: 2000 Tax: $25,244 (2024)Community: Baywood Colony Westport Sec 2Spa: YesSingle Family
Taxes:$25,244
Remarks: Welcome to ‘The Retreat at Tidewood’, a boater’s paradise nestled in one of Sarasota’s most desirable and secluded waterfront communities. Imagine living just minutes from downtown, fine dining, and shopping, all without the hassle of an HOA. This home offers the perfect blend of convenience and tranquility for those who love life on the water. Elevated 12 feet, this residence ensures peace of mind protection from flooding. Step inside to discover an updated gourmet kitchen with custom cabinetry and premium finishes, a spacious living and dining room, and a luxurious master suite with Venetian Plastering and his-and-hers closets. Every room on the ground floor opens directly to the pool, creating a seamless indoor-outdoor flow to over 2,500 sq. ft. of screened outdoor living — perfect for entertaining or relaxing in total privacy. For the avid boater, the property features a concrete seawall for easy canoe or kayak launching, making it effortless to explore the serene Intercoastal Waterway. Additionally, a boat yard just a short distance away accommodates larger watercraft and offers concierge services, ensuring your boating adventures are always within reach. Upstairs, a private “in-law suite” is accessible by elevator or stairs and includes three flexible rooms, full bath with tub/shower combo, kitchenette, a large walk-in closet, room to add an additional bathroom, and a screened porch overlooking the tranquil waterway, Siesta Key, and timeless sunsets. Surrounded by protected mangroves, the views are as peaceful as they are timeless. Designed for multi-generational living or hosting guests with ease, this home blends thoughtful functionality with waterfront luxury. Its location combines seclusion and convenience — tucked away in a peaceful community, yet close to everything Sarasota has to offer. The adjacent lot could also be purchased for additional acreage, offering even more space and potential. The ‘Retreat at Tidewood’ offers a once-in-a-lifetime opportunity to own a piece of paradise. This unique experience awaits you with the perfect blend of comfort, privacy, coastal beauty, and a lifestyle tailored for those who cherish the water.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Nancy Grenier (941-364-4000)
2244 SUNNYSIDE PL, SARASOTA, FL 34239
$549,00053 Days on yellowkey MLS ID: A4684357
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1116 Built: 1958 Tax: $5,227 (2025)Community: Sunnyside ParkSingle Family
Taxes:$5,227
Remarks: Location! Location! Location! Only 5.5 miles approx. to the world-famous Siesta Key Beach with its fine quartz sand from the Appalachian Mountains. Sunnyside Park is a sought-after subdivision, situated between Arlington Park & South Gate in the desirable Southside School District. This solid block house features fenced in back yard with room for a pool, playground or for any outdoor enjoyment. This is a 3-bedroom 2 bath house, plenty of windows, bright and airy. Terrazzo floor throughout. Laundry room and a screened lanai. Single car garage Unfurnished, move-in ready. Roof 2014. AC 2018. New appliances and granite counter tops in 2010. See attachment for Improvements & Updates. There is double driveway and a single car garage. Just minutes from Sarasota Memorial Hospital, the Hillview district with its restaurants and shops, including the Mortons Gourmet Market. Easy and quick access to downtown Sarasota with all its dining, shopping, theatres arts and culture it has to offer. If you do not want the hassle of monthly condo dues and restrictions, then make this house your home.
Listing is courtesy of: ASHTON LAKES REALTY INC (941-924-4832)
Listing Agent: Philip Abraham (941-441-6958)
1621 MEMORY LN, SARASOTA, FL 34231
$3,980,000106 Days on yellowkey MLS ID: A4677041
Bed: 5 Bath: 7.0 Gar: 2 Liv Area Sq Ft: 4626 Built: 2027 Tax: $16,466 (2025)Community: Not Part Of A SubdivisionSpa: YesSingle Family
Taxes:$16,466
Remarks: Pre-Construction. To be built. 1621 Memory Lane presents a rare opportunity to build a custom bayfront estate on Little Sarasota Bay in the Bayview Acres neighborhood, one of Sarasota’s most strategically positioned mainland waterfront communities. Situated on a quiet no-through street south of Stickney Point Road and west of Tamiami Trail, this expansive .47-acre parcel offers approximately 100 feet of direct frontage on the bay and the scale to design a significant coastal residence with generous outdoor living areas, pool, and the ability to construct a private pier, subject to permitting. The property is offered as a vacant lot for $1,480,000 or as a to-be-built custom residence by The Vision Group priced at $3,980,000, providing flexibility for buyers to bring their own builder or move forward with a fully designed plan. The setting delivers privacy and calm while remaining just minutes from the south bridge to Siesta Key and equally convenient to downtown Sarasota’s dining, arts, and cultural amenities. Continued investment along the U.S. 41 and Siesta Drive corridor, including Benderson’s planned retail and mixed-use development, further strengthens the long-term appeal of this location. The property is especially well suited for buyers transitioning off the barrier islands who want mainland accessibility without sacrificing water views, as well as inland residents ready to elevate to a true bayfront setting without HOA constraints. With limited remaining buildable bayfront parcels of this size and frontage—and new construction next door on a comparable lot estimated at $6 million in value—the economics present a compelling opportunity to build at a meaningful discount to neighboring new construction.
Listing Agent: Daniel Treiman (917-657-7495)
1701 SOUTHWOOD ST #1701, SARASOTA, FL 34231
$260,000161 Days on yellowkey MLS ID: A4671475
REDUCED by $5,000 (1.9%) on 03/31/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1164 Built: 1981Monthly Fee: $1,273 Tax: $3,371 (2024)Community: Baywood ColonySpa: NoCondo
Taxes:$3,371
Remarks: RECENT PRICE ADJUSTMENT - MOTIVATED SELLERS! Rare Opportunity in Prestigious West of the Trail - Welcome to an exceptional corner residence just steps from the Intracoastal Waterway, nestled within the highly desirable Baywood Colony Southwood community. This beautifully updated 2-bedroom, 2-bath end unit is filled with natural light, enhanced by an abundance of windows complemented with elegant plantation shutters throughout. The front screened lanai has been fully enclosed with sliding glass panels and additional plantation shutters, creating a stylish and versatile space ideal for year-round enjoyment. Inside, the home presents like a model, featuring a stunning open-concept kitchen with granite countertops, a generous breakfast bar, stainless steel appliances, and premium soft-close wood cabinetry accented by under-cabinet lighting. A washer and dryer are conveniently located inside the residence, and elegant tile flooring extends throughout. Major improvements provide peace of mind, including a new A/C system (2018), a roof replacement by the HOA (2019), and a recently re-plumbed building. This ground-floor unit offers the added convenience of a covered parking space directly behind the residence, along with a secondary private entry from the carport. Residents enjoy an exceptional Florida lifestyle with access to a heated saltwater pool, tennis and pickleball courts just steps away, and tranquil walks to the Baywood Colony fountain—perfect for taking in spectacular bayfront sunsets. With only 32 residences, the community offers a rare sense of privacy and boutique-style living. The location is unbeatable: just 2.2 miles from beach access with an easy bike ride, and within walking distance to Phillippi Estate Park—a picturesque 60-acre waterfront preserve offering kayaking, fishing, scenic trails, a playground, a weekly Wednesday farmers market, and a variety of community events including art fairs and concerts. This pet-friendly, maintenance-free community includes basic cable, exterior and grounds maintenance, roof and window coverage, and pest control—all included in the low monthly fee of $1,273. Best of all, the community is not age-restricted. Experience the perfect blend of comfort, convenience, and coastal elegance in this truly special Sarasota residence.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Jo James, Llc (941-928-3175)
558 VENICE LN, SARASOTA, FL 34242
$4,649,90012 Days on yellowkey MLS ID: A4689132
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4132 Built: 2025Monthly Fee: $33 Tax: $4,509 (2025)Community: Siestas Bayside Waterside EastSpa: YesSingle Family
Taxes:$4,509
Remarks: Newly completed and move-in ready, this Coastal Contemporary waterfront residence on Siesta Key by award-winning Heritage Builders offers 4,132 sq ft with 5 bedrooms, 4.5 baths, a private study, loft, and elevator—perfectly blending luxury, functionality, and coastal living. The main level features white oak wood floors, soaring beamed ceilings, and a bright open-concept layout designed for both everyday living and entertaining. The gourmet kitchen and expansive great room flow seamlessly through 10’ impact-resistant sliding glass doors to the outdoor living area, showcasing tranquil views of the pool and Grand Canal. A dedicated private office, a luxurious primary suite with a spa-inspired bath, and an additional ensuite guest bedroom complete the first floor. Upstairs, a spacious loft provides an ideal secondary gathering space. The VIP suite features a private balcony overlooking the water, while the fifth bedroom offers flexibility as a media room, fitness studio, or guest retreat. A custom wet bar enhances the upper level, creating the perfect setting for entertaining. Set along the scenic canals of Siesta Key, this property offers exceptional boating opportunities with easy access to open water—ideal for enjoying the best of Florida’s waterfront lifestyle right from your backyard. The outdoor living space is designed as a private retreat, complete with a sparkling pool, spa, and peaceful water views. Quick out to the expensive Intracoastal waterways for boaters. Florida living at its finest — sunset views, alfresco dining, and cozy evenings by the outdoor fireplace. A beautiful patio and grill setup that feels like a dream come true. Located just minutes from Siesta Key Beach, this home provides quick access to world-renowned beaches, dining, and the vibrant coastal lifestyle that makes Siesta Key one of the most desirable destinations in Florida. Exceptional opportunity to own a brand-new waterfront home with boating access in one of Sarasota’s premier locations.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Andrew Haddad (941-313-1218)
5740 MIDNIGHT PASS RD #403, SARASOTA, FL 34242
$1,950,0005 Days on yellowkey MLS ID: A4686166
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1449 Built: 1986 Tax: $12,418 (2025)Community: Gulf & Bay Club Ph 6Spa: YesCondo
Taxes:$12,418
Remarks: A rare and exceptional offering within Building F at Gulf & Bay Club on Siesta Key, Unit 403 presents a truly one-of-a-kind coastal retreat. Completely taken down to the studs and reimagined in 2023, this residence showcases a meticulous, high-end renovation where no detail was overlooked. From the moment you enter, you’re welcomed by a light-filled, open-concept design with sweeping direct Gulf views that immediately set the tone. The chef’s kitchen is the centerpiece of the home, anchored by a stunning 12-foot oversized island with seating for six. Featuring eco-friendly PaperStone countertops and backsplash, a full suite of premium Thermador appliances, and seamless custom finishes, the space is as functional as it is striking—all complemented by breathtaking water views as you cook and entertain. Offered turnkey furnished, the interiors are thoughtfully curated with pieces from Arhaus, Restoration Hardware, and other luxury brands, creating a cohesive and sophisticated aesthetic. The open layout flows effortlessly from kitchen to dining to living, enhanced by custom built-ins that provide both style and smart storage, including a paneled wine refrigerator. Wake up to the Gulf from your private primary suite, a serene retreat designed for both comfort and elegance. This space features a dedicated vanity area, custom walk-in closet, and a beautifully appointed en-suite bath, offering a spa-like experience within your own home. Additional highlights include engineered hardwood flooring throughout, hurricane-impact windows and sliders, solid-core doors, and extensive custom storage solutions—all contributing to the home’s elevated design and livability. This two-bedroom, two-bath residence is set within the highly sought-after Gulf & Bay Club, where residents enjoy an unmatched, resort-style lifestyle across 32 acres of lush, manicured grounds. Indulge in 800 feet of private, powdery white sand beach, three heated pools, tennis and pickleball courts, a state-of-the-art fitness center with yoga studio and saunas, and multiple clubhouses featuring lounges, billiards, and social spaces. Additional amenities include barbecue and picnic areas, freshwater lakes, and EV charging stations. Ideally located just moments from the dining, shopping, and vibrant energy of Siesta Key Village—including the iconic Sunday Drum Circle—this residence offers the perfect blend of privacy, luxury, and convenience. Unit 403 is more than a home—it’s a rare opportunity to experience the very best of Gulf-front living on Siesta Key.
Listing Agent: Drew Jacobsen (941-253-6309)
3174 REGATTA CIR, SARASOTA, FL 34231
$438,900Listed 04/22/2026 5:36AM MLS ID: A4689148
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1279 Built: 1963Monthly Fee: $6 Tax: $4,089 (2025)Community: Gulf GateSpa: NoSingle Family
Taxes:$4,089
Remarks: Bright and light, charming, nicely updated two bedroom, two bath home sold TURNKEY furnished in the lovely Gulf Gate community on a quiet circle street! Don’t miss this tropical oasis with a beautiful backyard and screened in patio ready for new owners – just bring your toothbrush! This community has an optional HOA and no CDD fees! This one car garage home includes the following updates: new exterior paint 2026, new interior paint in 2021, new wind rated sliding doors in 2021, new screened in patio 2021, new range and refrigerator in 2021, new garage exterior door in 2024, garage painted in 2023, new gas grill in 2026, new updated lighting in 2021, and new HVAC installed in 2018. Close to shopping, restaurants, and only 3.9 miles to the famous #1 Beach in the USA - Siesta Key! Enjoy as your personal home or as a great investment opportunity. Don't miss this home, make your appointment to see today!
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Alice Lewis (941-402-5564)
4660 OCEAN BLVD #Q1, SARASOTA, FL 34242
$525,000244 Days on yellowkey MLS ID: A4659204
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1200 Built: 1971 Tax: $7,101 (2024)Community: Sea VillageCondo
Taxes:$7,101
Remarks: PRICED TO SELL! New hurricane-impact sliders have been ordered and will be installed prior to closing. Experience million-dollar, direct Gulf views from this ground floor condominium in the sought after community of Sea Village on Siesta Key. Enjoy sunsets every evening from your private lanai, just steps from the shoreline and minutes from one of the world’s top beaches. This 2-bedroom, 2-bath residence has been thoughtfully updated with a fully remodeled kitchen, tile flooring throughout, and plantation shutters. Hurricane-impact windows provide peace of mind and lasting value. Additional features and upgrades include a 2021 water heater, 2022 HVAC, 2023 electrical panel, in-unit washer and dryer, designated parking, storage shed, and bike storage. Sea Village offers residents a true coastal lifestyle with a heated waterfront pool, tropical grounds, and easy access to dining, shopping, and Siesta Key’s vibrant village. Covered parking and generous guest parking make entertaining convenient. Perfect as a primary residence or seasonal retreat, this home blends unmatched views with modern upgrades in one of Sarasota’s most desirable island communities.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Halie Monde (941-735-4707)
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