Location: Sarasota
Do Not Show Listings
1006 DE LEO DR, SARASOTA, FL 34243
$325,0009 Days on yellowkey MLS ID: A4696192
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1345 Built: 1972 Tax: $2,416 (2025)Community: Whitfield Country Club Heights Un 5Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,416
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Charming and ideally located in Whitfield Estates, this 2-bedroom, 2-bath home offers the perfect blend of character, comfort, and convenience. Inside, you’ll find original wood floors that add warmth and timeless appeal, while major system updates provide peace of mind for years to come. The home features hurricane impact windows and doors, a newer HVAC system, a recently updated water heater, and fully paid-off solar panels that help keep electric costs remarkably low currently averaging less than $40 per month. With 1,345 square feet of living space, the layout is both functional and inviting, making it an excellent option for first-time homebuyers, seasonal residents, or investors seeking rental flexibility. Whitfield Estates allows short-term rentals, creating an opportunity for personal enjoyment and income potential. Location is everything, and this home delivers. Situated just minutes from IMG Academy, Abel Elementary School, Sarasota-Bradenton International Airport, downtown Sarasota, St. Armands Circle, and the area’s world-renowned Gulf Coast beaches, you’ll enjoy easy access to everything that makes Sarasota one of Florida’s most desirable destinations. Sara Bay Marina is also nearby, offering convenient dry dock storage and access to Sarasota’s waterfront lifestyle. Whitfield Estates also offers a voluntary neighborhood association for only $40/year, providing culinary access to the Sara Bay Country Club. Whether you’re searching for a primary residence, winter retreat, or investment property, this charming Whitfield Estates home is ready to welcome its next owner.
Listing is courtesy of: SARABAY REAL ESTATE INC (941-355-7696)
Listing Agent: Jessie Bonner (941-356-3182)
2945 UPPER TANGELO DR, SARASOTA, FL 34239
$660,00048 Days on yellowkey MLS ID: A4690742
2 Days Off yellowkey (back on 6/9/2026)
REDUCED by $35,000 (5.0%) on 05/20/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1439 Built: 1960 Tax: $6,132 (2025)Community: South GateSpa: NoSingle Family
Taxes:$6,132
Elementary School: Southside Elementary
High School: Sarasota High
Middle School: Brookside Middle
Remarks: A rare offering within Sarasota’s desirable South Gate community, this meticulously restored Atomic Ranch embodies the essence of authentic Mid-Century Modern design. Revered as one of the foundational architectural styles of the 20th century, this residence has been thoughtfully preserved and elevated by discerning owners who understood the importance of honoring its original integrity. Ideally positioned in the heart of Sarasota, the home offers effortless access to world-class beaches, premier shopping and dining, top-rated schools, Sarasota Memorial Hospital, and the vibrant downtown district. The residence unfolds with a seamless, open-concept design, featuring three spacious bedrooms and two bathrooms, an inviting eat-in kitchen area, and expansive living areas designed for both comfort and entertaining. Walls of vintage sliding glass doors dissolve the boundary between indoors and out, opening to a generous pool terrace. Both covered and open-air, this creates a true indoor-outdoor lifestyle synonymous with classic Florida modernism. Authentic details remain beautifully intact, including original terrazzo flooring throughout, vintage architectural elements, and curated mid-century finishes that speak to the home’s heritage. An oversized garage, along with substantial fenced exterior space, provides flexibility for additional parking, including room for a boat or recreational vehicles. The home has been featured on Sarasota’s renowned “MOD Tour,” celebrated for its originality and preservation. As noted during the tour, the residence showcases vintage sliding glass walls, vibrant period kitchens and baths, and a fluid connection to the pool area. Carefully selected furnishings that reflect the era enhance the spirit of 1960s design. This is a truly special opportunity to own a piece of architectural history. Thoughtfully restored, exceptionally located, and ready to be experienced.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Kelly Gettel (941-315-2525)
7716 GENEVA LN, SARASOTA, FL 34243
$445,000365 Days on yellowkey MLS ID: A4655951
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1454 Built: 1991Monthly Fee: $188 Tax: $2,176 (2024)Community: Treetops At North FortySpa: NoSingle Family
Taxes:$2,176
Elementary School: Kinnan Elementary
High School: Southeast High
Tax Year: 2024
Middle School: Braden River Middle
Remarks: Step through the front door and into a light-filled, open great-room layout where vaulted ceilings, walls of windows, and dual sets of French doors blur the line between indoor and outdoor living. This updated 2-bedroom, 2-bath home with a flex den/office is tailor-made for both relaxed daily living and unforgettable gatherings. Stylish, Ready-to-Entertain Interior Kitchen redone in 2014: stainless-steel appliances, granite counters, breakfast bar, pantry, and a sunny nook with slider to the garden. Tile floors throughout—zero carpet for allergy-friendly, easy maintenance. Split-plan privacy: the airy primary suite enjoys pool access, dual sinks, and frameless tile shower, while the guest wing shares an upgraded bath with the den nearby. Outdoor Oasis Slide open the French doors and savor the Florida lifestyle on the screened, covered lanai overlooking a sparkling saltwater pool. Host cookouts, sip morning coffee amid the side garden, or toast another brilliant Gulf-coast sunset. Peace-of-Mind Updates & Storage Roof 2015 • Water heater 2020 Oversized 2-car garage with built-in storage shelves for toys and tools alike. Resort-Style Amenities & Prime Location Residents of Tree Tops at North Forty enjoy a community pool and tennis court, all moments from world-class golf, dining, shopping, and downtown Sarasota’s arts scene. This is the move-in-ready, low-maintenance pool home you’ve been waiting for—schedule your private tour today!
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Jeff Simpson (941-504-5552)
2632 SUNNYSIDE ST, SARASOTA, FL 34239
$395,00052 Days on yellowkey MLS ID: A4690325
3 Days Off yellowkey (back on 6/8/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1578 Built: 1957Monthly Fee: $17 Tax: $4,699 (2025)Community: South GateSingle Family
Taxes:$4,699
Remarks: Under contract-accepting backup offers. Charming mid-century modern 3 bedroom, 2 bathroom home with an oversized 2-car garage, located in the established, deed-restricted South Gate neighborhood of Sarasota. Offering classic Florida style, the home features original terrazzo flooring throughout the home with the exception of ceramic tile in the kitchen and a functional layout with a spacious primary bedroom that includes an en-suite bathroom and walk-in closet. The living room features a built-in bookshelf, and an enclosed sunroom offers flexible space for a home office or additional family area. The home retains original features and offers ample storage throughout, plus a bonus workshop suitable for hobbies or projects. Recent updates include AC replacement (2023) a new garage door (2023), and brand-new toilets. Home is connected to county sewer and comes with Hurricane shutters. The optional South Gate Community Association offers access to a community pool and community center, including the architecturally significant Victor Lundy-designed property with events and weekly classes. Located in the highly sought-after Southside Elementary school district and near Southside Village, Sarasota Memorial Hospital, and just minutes to Siesta Key Beach, with convenient access to shopping, dining, and everyday amenities.
Listing Agent: Rachel Harvey (941-726-9300)
830 HAMMOCKWOOD CT, SARASOTA, FL 34232
$500,00044 Days on yellowkey MLS ID: A4691916
REDUCED by $50,000 (9.1%) on 05/16/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2131 Built: 1986Monthly Fee: $65 Tax: $6,286 (2025)Community: Woodland ParkSingle Family
Taxes:$6,286
Elementary School: Fruitville Elementary
Middle School: McIntosh Middle
Remarks: Under contract-accepting backup offers. -Rare one-story, cul-de-sac lot backing directly to a private nature preserve — one of Woodland Park’s most secluded settings. -Upon entering you will find vaulted ceilings, rich Brazilian cherrywood floors, and walls of windows that frame preserve views from nearly every room. -A wood-burning fireplace and custom staircase anchor the main living area, while skylights flood the space with natural light throughout the day. -The outdoor living is equally impressive — a private covered and screened pool deck creates a year-round retreat that’s as suited for quiet mornings as it is for entertaining. -Recent updates include a BRAND-NEW ROOF and a replacement AC system installed in 2024, so the big-ticket items are already handled. -Low HOA fees of just $65/month. -Woodland Park — oak-canopied streets, nature preserve access, and Old Florida character that’s increasingly rare to find.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Barry Brodsky (941-313-4590)
4913 ALMANZA AVE, SARASOTA, FL 34235
$419,90024 Days on yellowkey MLS ID: A4694051
0 Days Off yellowkey (back on 6/8/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1640 Built: 1980 Tax: $3,822 (2025)Community: De Soto LakesSingle Family
Taxes:$3,822
Elementary School: Emma E. Booker Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Ideally located near shopping, dining, the new Mote Marine Aquarium at UTC and the Sarasota-Bradenton International Airport, this move-in ready home offers the perfect blend of comfort, convenience, and freedom. Just minutes from Nathan Benderson Park with miles of walking and biking trails, kayaking, rowing, and year-round community events. Enjoy true Florida living with NO CDD fees, NO HOA fees, NO deed restrictions, and NO flood insurance required — not located in a flood zone. Bring all your Florida toys with plenty of room for your RV, boat, jet-skis, and more! This spacious 3-bedroom, 2-bath split floor plan features both living & family rooms, an updated kitchen & bathrooms and a private primary suite with walk-in closet and en-suite bath. Recent major updates include a NEW roof and NEW AC in 2026, NEW hot water heater 2020, plus repiping completed in 2020 for added peace of mind. Step outside to the lanai overlooking a large fenced backyard — perfect for entertaining or pets. Complete with a 2-car garage and centrally located near Sarasota’s best amenities, this property is ideal for full-time residents, seasonal owners, or investors alike.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Mike Bridges (941-316-6530)
2839 OLYMPIC ST, SARASOTA, FL 34231
$426,000131 Days on yellowkey MLS ID: A4680914
REDUCED by $13,900 (3.2%) on 06/08/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1271 Built: 1955 Tax: $2,877 (2025)Community: Sarasota Venice Co 09 37 18Single Family
Taxes:$2,877
Remarks: Beautiful!! Completely rehabbed with nice finishes throughout,New Ac and much more , this move-in-ready home offers modern updates, quality craftsmanship, and a bright, welcoming interior. Ideally located near top Sarasota schools, shopping, and dining, and just minutes from Siesta Key Beach, this property delivers both comfort and convenience in one of Sarasota’s most desirable areas. The neighborhood features new construction homes selling at significantly higher prices, making this an exceptional value. Enjoy a spacious, fully fenced patio—including the front yard—for absolute privacy, with plenty of room for an RV, multiple vehicles, or a boat. Schedule your showing today and explore the possibilities for yourself.
Listing is courtesy of: GENESIS JC REALTY LLC (941-281-8829)
Listing Agent: Juan Reyes (941-281-8829)
3543 65TH AVENUE CIR E, SARASOTA, FL 34243
$323,00024 Days on yellowkey MLS ID: A4694314
REDUCED by $6,000 (1.8%) on 06/08/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1211 Built: 1988Monthly Fee: $29 Tax: $2,737 (2025)Community: Centre Lake SubSpa: NoSingle Family
Taxes:$2,737
Remarks: Welcome to this charming 3 bedroom home featuring an open floor plan and inviting indoor-outdoor living spaces. Once you walk in, you'll appreciate the seamless flow between the living room, dining room, and kitchen, while the vaulted ceiling creates a bright and airy feel throughout the main living area. Enjoy Florida living from both the screened lanai and adorable screened front porch - perfect for relaxing with morning coffee or unwinding in the evenings. Additional features include a newer roof, washer, dryer, stove, and dishwasher. With an HOA of only $350/year, you'll enjoy affordability along with convenience and charm. Ideally located just 6 miles from both downtown Bradenton and Sarasota, 8 miles from Lido Beach and St. Armands Circle, and only 5 miles from all of the shopping and dining at UTC—this home offers an amazingly convenient location while still feeling like a peaceful retreat. Full of character, this home is ready for its next owner to add their personal touches. **This property qualifies for a Lender Credit of 1% Discount Point that can be used towards closing costs or buying down the rate if using preferred lender. Inquire for more details** Schedule your showing today!
Listing Agent: Kristy Gentile (941-720-6699)
7800 CENTAURUS WAY, SARASOTA, FL 34241
$743,10988 Days on yellowkey MLS ID: A4686768
REDUCED by $50,000 (6.3%) on 06/08/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2999 Built: 2026Monthly Fee: $251Community: Cassia At Skye RanchSingle Family
Taxes:$0
High School: Riverview High
Remarks: Under Construction. What's Special: Cul-de-Sac Lot | Corner Lot | Pond View | Dedicated Study. New Construction - July Completion! Built by America's Most Trusted Home Builder. Welcome to the Montauk at 7800 Centaurus Way in Cassia at Skye Ranch! This thoughtfully designed two-story home offers flexible, functional living with four bedrooms, three-and-a-half baths and a spacious open layout. The kitchen, dining area and great room come together beautifully and extend onto the covered lanai for easy indoor–outdoor living. A private first-floor primary suite features a spa-inspired bath and a generous walk-in closet, while a bright study and convenient laundry room sit just off the foyer. Upstairs, a cheerful game room, three secondary bedrooms and two bathrooms create plenty of room for everyday moments and fun gatherings. All of this is set within the welcoming Cassia community, where friendly streets and thoughtful amenities enhance daily living. Skye Ranch sits in a prime Sarasota location at Clark and Lorraine Roads, offering a vibrant setting with access to the Skye Ranch K-8 school. The community preserves natural beauty with grand oaks, palms, wetlands, lakes, and native wildlife. Miles of trails connect you to nature, parks, and exceptional on-site amenities. Additional Highlights Include: gourmet kitchen, tray ceiling package, game room, interior 8' doors, pocket sliding glass door in gathering room, pre-plumb for laundry tub, study, apron front kitchen sink, extra flush mount lighting throughout, three kitchen pendant lights, upgraded quartz countertops, upgraded luxury vinyl flooring throughout first floor, and upgraded cabinets throughout with 42" cabinets in the kitchen. Photos are or representative purposes only. MLS#A4686768
Listing is courtesy of: TAYLOR MORRISON RLTY OF FLA (866-495-6006)
Listing Agent: Michelle Campbell (866-495-6006)
10839 ECLIPSE ST, SARASOTA, FL 34241
$678,429104 Days on yellowkey MLS ID: A4684534
REDUCED by $21,000 (3.0%) on 06/08/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2395 Built: 2026Monthly Fee: $251Community: Cassia At Skye RanchSingle Family
Remarks: Under Construction. What's Special: Close to Amenities | Dedicated Study | Corner Lot | Conservation View. New Construction - August Completion! Built by America's Most Trusted Home Builder. Welcome to the Longboat at 10839 Eclipse Street in Cassia at Skye Ranch! This thoughtfully designed new home blends comfort with elevated style thanks to whole house impact windows, upgraded flooring, and upgraded cabinets throughout. At the heart of the home, the open-concept great room connects seamlessly to the dining area and the gourmet kitchen, complete with an apron-front sink, quartz countertops, a center island, and walk-in pantry. From the great room, step out to the covered lanai for easy indoor-outdoor living. Two secondary bedrooms, a full bathroom, and the laundry room sit just off the kitchen, while another secondary bedroom suite with a private bath and a dedicated study is located off the foyer. The primary suite is tucked away and offers a spa-inspired bathroom and a large walk-in closet with direct access to the laundry room. Skye Ranch sits in a prime Sarasota location at Clark and Lorraine Roads, offering a vibrant setting with access to the Skye Ranch K-8 school. The community preserves natural beauty with grand oaks, palms, wetlands, lakes, and native wildlife. Miles of trails connect you to nature, parks, and exceptional on-site amenities. Additional Highlights Include: Gourmet kitchen, study in place of flex, door at primary closet to laundry, 8' interior doors, tray ceilings package, impact windows, and pool and spa prewire. MLS#A4684534
7875 INTERSTELLAR AVE, SARASOTA, FL 34241
$649,81160 Days on yellowkey MLS ID: A4690233
REDUCED by $41,000 (5.9%) on 06/08/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2582 Built: 2026Monthly Fee: $251Community: Cassia At Skye RanchSpa: NoSingle Family
Remarks: Under Construction. What's Special: Multi-Gen Suite | Corner Lot | Close to Park | Close to Trails. New Construction - August Completion! Built by America's Most Trusted Home Builder. Welcome to the Anastasia at 7875 Interstellar Avenue in Cassia at Skye Ranch! This new home offers a thoughtfully crafted layout that feels bright, comfortable, along with whole house impact windows for added peace of mind. From the front porch, the angled foyer leads you past a dedicated study on one side and the two-car garage entry on the other before opening into the heart of the home. The gourmet kitchen stands out with quartz countertops, an apron front sink, pendant lighting, generous counter space, and a spacious pantry, all overlooking the dining area and great room. Pocket sliding doors open to a covered lanai, extending your living space outdoors for relaxed everyday moments. Tucked just off the dining area are the laundry room and powder room, while the main level primary suite offers backyard views, a walk-in closet, and a comfortable en-suite bath. Upstairs, two secondary bedrooms share a full bathroom, a private secondary bedroom suite features its own en-suite bath and two walk-in closets, and a spacious game room and loft give you flexible space to gather, unwind, or play. Skye Ranch sits in a prime Sarasota location at Clark and Lorraine Roads, offering a vibrant setting with access to the Skye Ranch K-8 school. The community preserves natural beauty with grand oaks, palms, wetlands, lakes, and native wildlife. Miles of trails connect you to nature, parks, and exceptional on-site amenities. Additional Highlights Include: Gourmet kitchen, alternate study location, pocket sliding door at great room, upstairs secondary suite, game room, tray ceiling pkg, 8' interior doors, pocket door at primary bed to bath, upgraded cabinets and flooring, and impact windows. Photos are for representative purposes only. MLS#A4690233
7549 WESTMORELAND DR, SARASOTA, FL 34243
$549,000102 Days on yellowkey MLS ID: A4684919
REDUCED by $20,000 (3.5%) on 06/08/2026
Bed: 2 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 1410 Built: 1956Monthly Fee: $3 Tax: $2,912 (2024)Community: Whitfield Estates Unit 1Single Family
Taxes:$2,912
Remarks: West of the Trail in Whitfield Estates, this mid-century gem captures the charm and character that define classic Florida architecture. From the original terrazzo floors to the preserved kitchen design, the home reflects the clean lines and simplicity that make mid-century residences so desirable. The spacious great room with fireplace serves as the heart of the home, offering natural light and comfortable gathering space while maintaining its authentic architectural appeal. Situated on a rare double lot, the property offers exceptional flexibility and long-term potential. Expand the footprint, design a custom pool, add a detached garage, or simply enjoy the privacy and space that are increasingly rare west of the Trail. Located on sought-after Westmoreland Drive, just across from multi-million-dollar bayfront estates, this property blends historic charm with premier positioning. Residents of Whitfield Estates have the unique opportunity to enjoy dining at nearby Sara Bay Country Club. For an optional annual HOA fee of just $35, owners may obtain a culinary membership granting full access to the clubhouse for dining and social events (golf privileges not included; membership subject to club approval). Minutes to Sarasota Bay, IMG Academy, SRQ Airport, and downtown Sarasota — this is authenticity, land, and lifestyle in one of the area’s most established West of the Trail neighborhoods.
Listing Agent: Lisa Kartz (941-587-3602)
300 GARDEN LN, SARASOTA, FL 34242
$2,790,000282 Days on yellowkey MLS ID: A4662830
REDUCED by $209,000 (7.0%) on 05/21/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3256 Built: 1975Monthly Fee: $10 Tax: $12,545 (2024)Community: Siesta Rev OfSpa: NoSingle Family
Taxes:$12,545
Elementary School: Phillippi Shores Elementary
Remarks: A Rare Opportunity on North Siesta Key with exceptional weekly income, prime location 350 Feet of Waterfront! Discover this unique multi-family income producing single-story property on Bay Island, offering both beauty and potential. High and dry, the home remained unaffected by recent storms, with 4–5 feet of elevation to spare. Set on a tranquil, tropical lot, this historic location on Garden Lane—once home to the Siesta Key Fish Market—with easy fast access to the bay and Big Pass it is truly a boater’s and fisherman’s paradise. Just a few steps to Shell Beach and its breathtaking sunsets, minutes from the world famous Siesta Beach, Siesta Village with restaurants, shopping, nightlife, quick access to downtown, and St. Armands Circle. You have it all! The property features a classic Florida ranch-style 4-bedroom, 2-bathroom home with a pool, large deck, and lush backyard designed for entertaining, plus a detached 2-bedroom, 2-bathroom guest house. Whether you choose to renovate, rebuild, or divide the lot (buyers to verify with the City), the possibilities are endless with this property!
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Holly Parry (941-809-8050)
2231 WOOD ST, SARASOTA, FL 34237
$1,999,000260 Days on yellowkey MLS ID: A4666469
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2731 Built: 2024 Tax: $4,662 (2023)Community: Poms Park 3Spa: YesSingle Family
Taxes:$4,662
Elementary School: Alta Vista Elementary
Tax Year: 2023
Remarks: This exquisite new-construction modern residence by Milano Homes, situated on an expansive double lot in the heart of Sarasota, blends elegance, convenience, and investment opportunity. Located within Sarasota city limits, this property qualifies for weekly rentals in one of the area’s most in-demand markets—a highly desirable option that allows for a strong six figure range income annually. This single-story home offers the ultimate in comfort with no stairs to navigate, featuring four spacious bedrooms, three-and-a-half designer bathrooms, and a two-car garage. The outdoor living space is a private sanctuary, complete with a sparkling pool and spa, outdoor shower, and a large fenced yard ideal for both relaxation and entertaining. As with all Milano Homes, the interiors showcase exceptional craftsmanship and imported Italian finishes. From the state-of-the-art kitchen—equipped with Subzero refrigeration, a Wolf induction cooktop, and Wolf oven—to the custom Italian cabinetry, fixtures, and flooring, every detail exudes sophistication. The open-concept living area flows seamlessly into the outdoor retreat, creating the perfect setting for gatherings and indoor-outdoor living. Perfectly positioned, this property offers easy access to the newly extended Legacy Trail, making it a haven for bikers, runners, and nature lovers. Downtown Sarasota’s vibrant arts, dining, and marina scene is just minutes away, while Siesta Key’s award-winning beaches and St. Armands Circle’s luxury shopping and dining are only a five-minute drive. Whether you’re seeking a full-time residence, seasonal retreat, or an income-producing short-term rental, this home offers an unmatched opportunity to enjoy and invest in the Sarasota lifestyle. Work hand-in-hand with the dedicated Milano Homes professionals to personalize this custom residence, creating a one-of-a-kind dream home tailored just for you.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Rinat Sikdar (941-993-9292)
4323 PINE MEADOW TER, SARASOTA, FL 34233
$515,00034 Days on yellowkey MLS ID: A4692509
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1494 Built: 1978Monthly Fee: $25 Tax: $5,227 (2025)Community: Pine MeadowSpa: NoSingle Family
Taxes:$5,227
Elementary School: Ashton Elementary
Middle School: Sarasota Middle
Remarks: Under contract-accepting backup offers. You found it! A newly renovated pool home directly bordering the Legacy Trail and just a short drive to Siesta Key Beach! This home is in the highly sought-after community of Pine Meadow. Positioned on an oversized, private corner lot with an extended driveway, this property also offers direct and private access to the Legacy Trail through a custom door built into the fully fenced backyard. Extensive and thoughtful interior updates include a renovated kitchen with granite countertops, matching stainless steel appliances, and luxury tile flooring that flows seamlessly throughout the home. The split-bedroom floor plan complements the master bedroom, which offers an abundance of natural light and quaint charm. Accented by a modern farmhouse sliding door, this room features a large walk-in closet and an updated en-suite bathroom with a walk-in shower and floor-to-ceiling tile. Both additional bedrooms also feature large walk-in closets. The home was FULLY RENOVATED in 2019, receiving a new roof, fully updated electrical system, new hot water heater, custom 10x16 storage shed, new garage epoxy flooring, and a new garage door. The pool was also resurfaced and upgraded with a new pool cage and pump equipment. Embrace the private, tranquil backyard setting complemented by a variety of mature trees and lush landscaping. Enjoy the pool and lanai from the shaded, covered section, or soak up the warm Florida sun while relaxing poolside. This home is in a highly desirable Sarasota location, just 5.5 miles from Siesta Key Beach. It is assigned to all A-rated schools, offers direct access to the Legacy Trail, and provides quick access to I-75 and Sarasota Memorial Hospital.
Listing Agent: Allen Smith, Iv (407-460-1564)
3656 OAK GROVE DR, SARASOTA, FL 34243
$849,90049 Days on yellowkey MLS ID: A4691432
REDUCED by $25,000 (2.9%) on 05/26/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4054 Built: 1981 Tax: $5,343 (2025)Community: Oak Grove ParkSpa: NoSingle Family
Taxes:$5,343
Remarks: Under contract-accepting backup offers. Welcome to this non mandatory hoa neighborhood, beautiful 4 bedroom 3 full bath pool home featuring a 1 bedroom 1 bath mother in law suite with private access making it a total of 5 bedrooms 4 full baths. The mother in law suite has established itself as a successful vacation rental presenting an outstanding investment opportunity. Enjoy a Sarasota address while paying Manatee County taxes all while being conveniently located to everything this area has to offer. Situated on over an acre of land, this versatile property is perfect for those who need room to live, work and play... Bring your rv's, trailers, work vehicles or car collection... There is ample parking and no deed restrictions to limit your lifestyle. Even horses are welcome - with space to build a barn or custom collector garage. This home has a butler's pantry with stylish barn doors that add charm and functionality. Step outside to a private oasis - a large peanut shaped saltwater pool (8' deep) screened lanai (rescreened in 2025). The main house with generous room sizes has living area, kitchen, dining room and family room, master bedroom and 2nd bedroom on 1st level while upstairs there are 2 bedrooms with dual closets and a jack and jill bathroom to share. New metal roof (2019) 3 zone a/c system, 2 water heaters, 2 sets of stainless stell appliances, well irrigation system, hurricane shutters and VOLUNTARY HOA!! This is a unique opportunity to own a flexible, income producing property with space to expand in a prime Sarasota location.
Listing is courtesy of: AFFORDABLE REAL ESTATE (941-751-3000)
Listing Agent: Susan Harrison-Phipps (941-685-8349)
4867 HUNTLEIGH DR, SARASOTA, FL 34233
$499,000100 Days on yellowkey MLS ID: A4685110
REDUCED by $26,000 (5.0%) on 06/02/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1937 Built: 1980Monthly Fee: $29 Tax: $3,040 (2025)Community: Beneva PinesSpa: NoSingle Family
Taxes:$3,040
Elementary School: Wilkinson Elementary
Remarks: Under contract-accepting backup offers. In the desired community of Beneva Pines in the heart of Sarasota, just five miles to the south bridge to the quartz sugar sand beaches of Siesta Key and Capt Curt's Restaurant and Tiki Bar! This smartly designed split plan home features an open plan, vaulted ceilings, and beautiful screened pool and lanai. The kitchen is the heart of this home and is surrounded by multiple gathering and dining areas. Impact sliders open off the Florida room to the pool. Most windows have been updated to impact rated as well. All four bedrooms are generous size and feature walk-in closets. The primary bedroom features an en-suite bath and two walk-in closets. Freshly painted inside, this home is ready for you to make it your own. Roof in 2022.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Holly Switow (941-735-3186)
4442 HOLLYBROOK WAY, SARASOTA, FL 34233
$663,00027 Days on yellowkey MLS ID: A4694025
REDUCED by $22,000 (3.2%) on 06/08/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2310 Built: 1994Monthly Fee: $80 Tax: $4,542 (2025)Community: GreenfieldSpa: NoSingle Family
Taxes:$4,542
Remarks: Beautifully updated and move-in ready 4-bedroom, 2-bath home in the highly desirable community of Greenfield, centrally located within top-rated school districts including Ashton Elementary School, Sarasota Middle School, and Sarasota High School. Greenfield offers low HOA fees and a peaceful setting with plenty of convenient shopping and dining amenities nearby and within short proximity to the white sand beaches of Sarasota. This meticulously maintained home is tucked along a quiet section of the neighborhood on an oversized quarter-acre lot. From the moment you arrive, you’ll appreciate the freshly painted exterior accented by timeless brick details and inviting curb appeal. Inside, the easy-living split floor plan offers 2,310 square feet under air with generous living spaces designed for both comfort and entertaining. This home is loaded with quality upgrades and recent improvements, including impact windows and sliders throughout (2025), luxury vinyl plank flooring, newer HVAC (2022), a fully updated kitchen (2022), recessed LED lighting, new ceiling fans (2026), and an impact-rated garage door (2020). The stunning gourmet kitchen features quartz countertops, stylish white shaker soft-close all-wood cabinetry with rollout drawers, stainless steel appliances, a large single-basin stainless sink, pantry storage, and both countertop seating and a dining area overlooking the pool. Just off the kitchen, the cozy living room centers around a charming wood-burning brick fireplace, creating the perfect gathering space for family and friends. The three guest bedrooms share a bathroom with convenient pool access, while the spacious primary suite offers privacy and comfort. Step outside to the generously sized screened lanai, an ideal outdoor retreat with ample shaded space for dining, relaxing, and grilling. The sparkling pool was resurfaced with a pebble finish in 2022 and features a newer Pentair pool pump, plus an outdoor shower for added convenience.The beautifully landscaped backyard is truly special, showcasing native Florida plants and flowering gardens designed for low-maintenance living. Enjoy Sunshine Mimosa ground cover, Mulberry trees, Elderberry, and a magnificent mature oak tree that provides natural shade and character. Additional exterior features include full irrigation and a new side fence installed in 2026. Every detail of this home reflects thoughtful design, exceptional upkeep, and high-quality craftsmanship, creating a stylish and worry-free property ready to be enjoyed for years to come.
Listing Agent: Heather Gehan (941-893-0213)
5301 SADDLE OAK TRL, SARASOTA, FL 34241
$1,999,000121 Days on yellowkey MLS ID: A4680226
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3978 Built: 2003Monthly Fee: $114 Tax: $10,477 (2025)Community: Saddle Oak EstatesSingle Family
Taxes:$10,477
Elementary School: Lakeview Elementary
Remarks: Under contract-accepting backup offers. Set on 6.34 private acres within the gated equestrian community of Saddle Oak Estates, this fully renovated estate has been reimagined for modern luxury living while preserving the rare sense of space and tranquility that defines the neighborhood. A long, impressive paver driveway introduces the nearly 4,000-square-foot residence, where estate privacy meets refined design just minutes from Sarasota’s everyday conveniences. Inside, wood-look tile flows seamlessly throughout the entire home, anchoring an open-concept layout designed for effortless indoor-outdoor living. The living room makes a striking first impression with a custom stone accent wall, fireplace, and built-ins that create a warm focal point for gathering. At the heart of the home, the chef’s kitchen is both elegant and functional, featuring a beautiful cabinetry with lighted upper cabinets, large island, gas range, stainless farmhouse sink, dine-in area, and a butler’s pantry that adds exceptional storage and prep space. A sunlit oversized dining room with custom cabinetry and high tray ceilings was designed for large family celebrations and entertaining. Walls of glass open directly to the pool terrace, blurring the line between inside and out. This impressive space is equally suited to function as a great room or media lounge, with the formal dining room positioned at the front of the home — currently styled as an inviting sitting area. A half bath is conveniently positioned here, and the second primary suite is located on this wing, creating the ideal setup for a private guest retreat or multigenerational living. The home offers two spacious primary suites, each with updated spa-inspired baths that feel like personal retreats. One suite includes a flexible den — perfect as a home office, gym, nursery or even a 5th bedroom. Two additional bedrooms and a full bath provide comfortable accommodations for family or guests. Thoughtful storage is built into every corner, including a cabinet-lined hallway leading to the oversized laundry room complete with granite counters, cabinetry, and utility sink. Plantation shutters, crown molding, and designer lighting elevate the interiors, adding warmth and sophistication throughout. Step outside to a true backyard oasis. The expansive paver patio surrounds a sparkling pool and flows into a large covered area with a wood-accent ceiling designed for lounging and outdoor dining. A pergola grilling area invites relaxed evenings entertaining under the stars, while a fenced dog run offers space for pets to roam. With flexible living spaces that adapt to your needs, expansive acreage, and the serenity of Saddle Oak Estates, this property delivers the rare combination of estate privacy and modern luxury, just minutes from Sarasota’s dining, shopping, and beaches.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Toma Milbank Pllc (941-720-5174)
6961 SCRUB JAY DR, SARASOTA, FL 34241
$1,075,000150 Days on yellowkey MLS ID: A4677370
REDUCED by $25,000 (2.3%) on 05/28/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4177 Built: 2006Monthly Fee: $142 Tax: $9,513 (2024)Community: Red Hawk ReserveSpa: YesSingle Family
Taxes:$9,513
Middle School: Riverview Middle
Remarks: Welcome to 6961 Scrub Jay Drive, a beautifully maintained Sarasota pool home where the major updates have already been completed, allowing you to move in and immediately enjoy the Florida lifestyle. Freshly painted inside and out, this home offers a bright, clean feel from the moment you arrive. The kitchen is equipped with brand-new appliances, while a new hot water heater and new pool pump provide added peace of mind for years to come. Step outside to your private backyard retreat featuring a sparkling pool surrounded by attractive pavers, creating the perfect setting for entertaining, relaxing, or enjoying sunny Florida afternoons. A convenient pool bath adds functionality and makes hosting family and friends effortless, while the spacious pool deck provides plenty of room to create the outdoor kitchen of your dreams. Whether you envision a simple grilling station or a fully equipped outdoor entertaining space, the layout offers the flexibility to bring your vision to life. Adding even more value, the homeowner is willing to offer a concession toward updates, giving buyers the opportunity to personalize the home to their tastes while enjoying the confidence that many of the major mechanical and maintenance items have already been addressed. With the costly improvements already completed, 6961 Scrub Jay Drive offers the ideal blend of comfort, convenience, and outdoor living in one of Sarasota's most desirable locations. Simply unpack, settle in, and start enjoying everything this exceptional home has to offer.
Listing is courtesy of: EXP REALTY LLC (800-486-1794)
Listing Agent: Matthew Hickey (941-539-6773)
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