Location: Sarasota
Do Not Show Listings
4444 DEER TRAIL BLVD, SARASOTA, FL 34238
$528,00068 Days on yellowkey MLS ID: A4693356
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1911 Built: 1992Monthly Fee: $205 Tax: $5,564 (2025)Community: Deer CreekVilla
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,564
Elementary School: Gulf Gate Elementary
High School: Riverview High
Tax Year: 2025
Middle School: Sarasota Middle
Remarks: Set in the sought-after Villas of Deer Creek on Palmer Ranch, this beautifully renovated home offers an open layout with 3 bedrooms and 2 baths. The great room showcases vaulted ceilings with tongue-and-groove detail and opens to a stunning chef’s kitchen featuring painted wood cabinetry, granite countertops, a decorative backsplash, GE Profile stainless-steel appliances, and a custom pantry with a floating island. The light-filled Florida room includes three sets of sliders leading to an ultra-private, tropical backyard oasis reminiscent of Selby Gardens. Polished white porcelain tile flooring and plantation shutters run throughout. Spacious primary suite with outfitted walk-in closet and French door to the lanai, while the spa-like primary bath features a frameless glass-tile shower, soaking tub, dual vanity, and an entire wall of cabinets. Two additional bedrooms are separated from the primary suite and share an updated bath with a walk-in shower and vanity; the front bedroom also works well as an office or den. Separate laundry room and 2-car garage. ROOF 2021, HVAC 2017, HTWTR 2024, INTERIOR PAINTED 2026. Deer Creek is a gated community with 24 hr. guard security. The HOA maintains the grounds and offers a heated community pool and social activities. Close to everything in Sarasota, including Shopping, all within 1 mile. Costco, Target, Sprouts, Starbucks, Kohls, the soon to be re-developed Sarasota Square Mall with Whole Foods as the anchor and a new Trader Joe's opening soon. The famous Legacy Trail is just a short distance away. A special home in the Villas of Deer Creek.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Betsy Campbell (203-554-8349)
9532 FOREST HILLS CIRCLE, SARASOTA, FL 34238
$555,00048 Days on yellowkey MLS ID: A4695500
REDUCED by $14,000 (2.5%) on 07/09/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1741 Built: 1998Monthly Fee: $326 Tax: $5,266 (2025)Community: Stoneybrook Golf & Country ClubVilla
Taxes:$5,266
Elementary School: None
High School: None
Middle School: None
Remarks: *One or more photos have been virtually staged* Experience luxurious living at its finest in this stunning, renovated villa located in the coveted Stoneybrook Golf & Country Club. Boasting stunning views of both the picturesque pond and the newly redesigned golf course, your dream home awaits! This spacious 2-bedroom, 2-bathroom villa offers over 1,700 sq ft of beautifully designed, open-concept living. The home’s recent updates include a brand-new AC system, installed in 2024 and still under warranty, as well as a new water heater and roof, both replaced in 2021. The renovated kitchen, completed in 2023, shines with new top-of-the-line appliances, quartz countertops and custom cabinetry. The primary bedroom includes a spacious, remodeled walk-in closet, designed for ample clothing and storage, and a large ensuite bathroom, with a new double vanity sink with a quartz countertop. The second bedroom hosts plenty of space and its accompanying bathroom has a new vanity sink with a quartz countertop. The office/flex room provides versatile space for work, hobbies or can become an additional bedroom when even more friends and family come to visit. New luxury vinyl flooring, installed in 2023, runs throughout the home and the 2-car garage that adds convenience and storage. Relax or entertain on your private lanai, perfectly positioned to enjoy the scenic nature that surrounds you. This villa is sold fully furnished with beautiful, modern furniture, making it truly move-in ready. With the ease of the roof, landscaping and exterior maintenance managed by the HOA, you can spend your days lounging at the community pool, biking or walking around the expansive community, meeting friends at the beautifully renovated main clubhouse for lunch, dinner or drinks or enjoying a round of golf. Located in the heart of Palmer Ranch, you are minutes from vibrant Downtown Sarasota, beautiful Siesta Key Beach and tons of shopping, restaurants, bars, museums and entertainment. This home offers an impeccable combination of comfort, style, and a premier lifestyle you won’t want to miss!
Listing is courtesy of: CORCORAN DWELLINGS REALTY (941-200-4663)
Listing Agent: Elisa Santamaria (941-928-8903)
7913 PINEGLEN CT #34, SARASOTA, FL 34238
$279,90050 Days on yellowkey MLS ID: A4695983
REDUCED by $5,000 (1.8%) on 06/20/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1466 Built: 1985Monthly Fee: $647 Tax: $1,718 (2025)Community: Pine Tree VillageSpa: NoVilla
Taxes:$1,718
Remarks: Discover this spacious and meticulously maintained 2 Bedroom, 2 Bathroom VILLA offering 1468 SQ FEET Of comfortable living space, complete with GARAGE. Located in the highly sought after PINE TREE COMMUNITY, You will be less than 5 miles from The world famous SW FL Gulf coast Beaches. Centrally located with easy access to Downtown Sarasota, St Armands Dining and shopping district and the long list of attractions that sarasota is famous for! Step inside and enjoy soaring ceilings, an open, and welcoming, immaculate VILLA. Enjoy the screened in lanai perfect to enjoy the FL sunshine! The estimated HOA of 600.00 includes: A HEATED POOL TENNIS COURTS LAWN CARE GARBAGE REMOVAL EXTERIOR MAINTENANCE Whether you are seeking winter getaway or, even better, A year round, full time residences, this very well could be the one with regards to comfort, convenience and LOOCATION! WELCOME TO ENDLESS SUMMER!
Listing is courtesy of: PREMIER PROPERTIES OF SRQ LLC (941-526-3113)
Listing Agent: Michael Panichelli (941-777-3450)
5368 KELLY DR #17, SARASOTA, FL 34233
$309,90056 Days on yellowkey MLS ID: A4695569
REDUCED by $15,000 (4.6%) on 07/13/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1944 Built: 1993 Tax: $2,864 (2025)Community: Crestwood Village Of Sara 2Villa
Taxes:$2,864
Remarks: Discover the perfect blend of comfort, convenience, and Sarasota lifestyle at 5368 Kelly Drive. This well-maintained home features a brand-new roof with a fully paid assessment and a freshly painted interior, providing peace of mind and a bright, move-in-ready atmosphere. The community clubhouse, swimming pool, and tennis/pickleball court add great entertainment opportunities. Enjoy being just minutes from the world-famous Siesta Key Beach, renowned for its powdery sand, crystal-clear Gulf waters, and spectacular sunsets. Whether you're looking for a full-time residence, seasonal retreat, or investment opportunity, the location places you close to shopping, dining, entertainment, and outdoor recreation. Inside, the freshly painted interior creates a clean and inviting setting ready for your personal touches. Outside, the new roof adds significant value and long-term durability, making this home an outstanding opportunity in today's market. The 3 bedrooms allows for flexibility for a work from home situation or hosting family and friends. Experience the best of Sarasota living with easy access to downtown Sarasota, parks, restaurants, and everyday conveniences.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Sean Hickey (941-587-4244)
5204 MAHOGANY RUN AVE, SARASOTA, FL 34241
$429,500143 Days on yellowkey MLS ID: A4684551
REDUCED by $20,000 (4.4%) on 04/21/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1585 Built: 1998Monthly Fee: $348 Tax: $4,072 (2025)Community: Heritage Oaks Golf & Country ClubVilla
Taxes:$4,072
Elementary School: Lakeview Elementary
Remarks: Experience the ultimate maintenance-free lifestyle in this stunning, turnkey Arlington Club home, perfectly positioned as an end unit with beautiful water and golf course views. This residence sits within the community, beautifully surrounded by the certified Audubon Cooperative Sanctuary of Heritage Oaks Golf & County Club. Here, you will live along 500 acres of breathtaking preserves and vibrant wildlife, offering a peaceful lifestyle immersed in nature. The home itself is defined by architectural charm, featuring a versatile third bedroom/den anchored by a bright skylight and elegant diagonal birch flooring. The updated kitchen boast of stainless steel appliances, granite countertops, and a charming breakfast nook, while expansive mirrors in the dining areas enhance the bright, open atmosphere. Both the owner's suite and guest bath have been completely renovated with modern fixtures, custom cabinetry, and granite countertops, including a luxurious walk-in shower in the master suite. Peace of mind comes standard with a fully re-piped and re-plumbed unit. Bask in natural light and iconic Florida sunsets thanks to the home's southern and western exposures. Outdoor living is a dream with a spacious rear lanai overlooking the 12th fairway and a second, south-facing lanai ideal for cooler days. As part of this golf community, residents enjoy an 18 hole championship course, five heated pools, a fitness center, and four lighted Har-Tru tennis courts. Whether you're grabbing a drink at the 19th Hole Bar & Grill or relaxing at the newly renovated clubhouse, this home offers the perfect upscale lifestyle and the great outdoors.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Laura Flood (941-725-2500)
5014 BARRINGTON CIR #2102, SARASOTA, FL 34234
$218,000184 Days on yellowkey MLS ID: TB8468599
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1078 Built: 1982Monthly Fee: $599 Tax: $579 (2024)Community: Barrington WoodsVilla
Taxes:$579
Tax Year: 2024
Remarks: Virtually Staged. Welcome to 5014 Barring Circle, Sarasota, a beautifully renovated 2-bedroom, 2-bath condominium that blends modern comfort with resort-style living. This move in ready home has been fully updated from top to bottom. Featuring a brand new kitchen with sleek white cabinetry, quartz countertops, stainless steel appliances and modern black fixtures that give the space a clean but contemporary feel. The open layout flows effortlessly into the living and dining areas enhanced by new flooring throughout and abundant natural light. Both bathrooms have been completely remodeled showcasing modern vanities, upgraded fixtures, illuminated mirrors and a stunning walk-in shower with designer tile creating a spa like experience at home. The spacious primary suite offers comfort and privacy while the second bedroom is perfect for guests, a home office or additional living flexibility. Outdoor storage closet for extra storage. Step outside to enjoy the peaceful community setting and take advantage of the condo community’s amenities, including a sparkling swimming pool and a fully equipped fitness center ideal for an active and relaxed Florida lifestyle, Lawn maintenance is included. Perfectly positioned just 3 minutes from Sarasota-Bradenton International Airport offering seamless travel without sacrificing peace and privacy, minutes from the pristine sands of Lido Beach and near shopping, dining and more! This condo is perfect as a primary residence, seasonal retreat or investment opportunity.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: William Garcia, Jr. (646-235-6634)
8605 RAIN SONG RD, SARASOTA, FL 34238
$479,900186 Days on yellowkey MLS ID: A4678947
REDUCED by $20,000 (4.0%) on 05/30/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1625 Built: 2019Monthly Fee: $521 Tax: $2,283 (2025)Community: Sunrise PreserveVilla
Taxes:$2,283
Elementary School: Ashton Elementary
Remarks: First time on the market! This newer-built, resilient home was constructed in 2019 to the latest hurricane codes and no flood insurance is required. Featuring a highly sought-after 2BR+Office/2BA floor plan with a 2-car garage, this residence is one of only 10 Maritime models built by Mattamy Homes, making it a rare opportunity. A welcoming front porch with retractable screen door provides wonderful airflow and leads to a gorgeous impact-glass front door. Inside, the open-concept layout is ideal for both everyday living and entertaining. The beautifully appointed kitchen showcases wood cabinetry, glass tile backsplash, quartz countertops, stainless steel appliances, and dimmable pendant lighting. The adjacent dining area comfortably accommodates a variety of table sizes and flows seamlessly into the spacious great room—perfect for gatherings. The primary suite offers a tray ceiling and a luxurious en-suite bath featuring an oversized frameless glass shower with bench seating, dual vanities, and a large walk-in closet. The guest suite is privately tucked away with an adjoining bath, providing excellent separation and privacy. The study includes a built-in desk and French doors, making it ideal for a home office or den. Additional highlights include tile flooring throughout the main living areas and study, 2 carpeted bedrooms, a laundry room with extra storage, and a finished garage with epoxy floors, utility sink, and an additional refrigerator. Crown molding and framed windows/sliders add an elegant, refined finish. Enjoy Florida living from the covered front porch or relax on the covered, rear screened lanai with pavers and privacy screen overlooking peaceful water and park-like views. Situated at the end of a cul-de-sac, this home benefits from minimal drive-by traffic. For added peace of mind, there are Accordion Shutters for all windows and sliders making preparing for hurricane a simple task that only takes minutes. The monthly HOA fee covers roof repair and replacement, exterior painting, exterior insurance, grounds maintenance, irrigation, and access to all community amenities and events. Sunrise Preserve at Palmer Ranch is a gated community offering resort-style amenities including a pool, tennis, pickleball and bocce ball courts, grilling areas, fire pit, clubhouse, and fully equipped fitness center. A robust calendar of social events makes it easy to meet neighbors and stay active. Ideally located in the Palmer Ranch area —convenient to shopping, dining, I-75, and world-class beaches.
Listing is courtesy of: ANDREWS & ASSOCIATES REALTY (941-921-5999)
Listing Agent: Stacey Andrews (941-504-1649)
1900 BENJAMIN FRANKLIN DR #V12, SARASOTA, FL 34236
$499,500257 Days on yellowkey MLS ID: A4671208
REDUCED by $50,400 (9.2%) on 07/17/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1242 Built: 1967Monthly Fee: $1,217 Tax: $7,227 (2024)Community: Lido HarbourVilla
Taxes:$7,227
Elementary School: Southside Elementary
High School: Sarasota High
Middle School: Booker Middle
Remarks: One or more photo(s) has been virtually staged. Villa 12 at First Lido is one of Lido Key's true hidden gems — a rare ground-level beachfront villa that delivers the privacy of a single-family home with the ease of maintenance free living. No elevator, no stairs — just step outside and the beach is right there. A private attached carport at your door and in-unit washer and dryer make everyday life effortless — amenities rarely found at this price point on Lido Key. Inside, this bright 2-bedroom, 2-bath villa features a fully updated open floor plan, porcelain tile throughout, brand new appliances and clean contemporary finishes. An enclosed Florida room adds versatile bonus space — den, office, or guest overflow, whatever you need it to be. A gulf-front heated pool with stunning views and direct private beach access complete the picture. Minutes from South Lido Park, St. Armands Circle and downtown Sarasota. Ground level. Beach access. Private carport. In-unit laundry. Lido Key address. This is the one.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Anthony Rechul (248-930-6638)
4481 ASCOT CIR N, SARASOTA, FL 34235
$285,000341 Days on yellowkey MLS ID: A4662740
REDUCED by $13,000 (4.4%) on 05/27/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1376 Built: 1994Monthly Fee: $894 Tax: $3,753 (2025)Community: Longwood VillasVilla
Taxes:$3,753
Elementary School: Emma E. Booker Elementary
High School: Booker High
Remarks: $3000 BUYER CREDIT OFFERED BY SELLER! Welcome to Tivoli Village—an exclusive, private community of just 100 residences nestled among mature trees and lush landscaping. This beautifully maintained 2-bedroom, 2-bath villa with a den/office and 2-car garage offers the perfect blend of tranquility and convenience. Step inside this home peacefully knowing the major concerns have been upgraded a NEWER ROOF, A/C 2023, WATER HEATER 2023, EXTERIOR PAINT IN 2023 AND NEW BACKFLOW METER IN 2026. Seller is offering a $3000 CREDIT for HOA fees! Ideally located near UTC shopping and dining, I-75, Nathan Benderson Park, Sarasota-Bradenton International Airport (SRQ), and just a short drive to downtown Sarasota and Gulf Coast beaches. Step inside to an open-concept floor plan featuring soaring cathedral ceilings, abundant natural light, and seamless flow between the kitchen, dining, and living areas—perfect for both everyday living and entertaining. The updated kitchen showcases newer stainless steel appliances, ample cabinetry with slide-out shelving, a breakfast nook, and an extended breakfast bar overlooking the main living space. Sliding glass doors lead to an enclosed lanai, with additional paver patio space extending into a private, tropical outdoor retreat complete with native Florida landscaping and a custom tiled table and seating area. The spacious primary suite is privately situated at the rear of the home and features an updated en-suite bath with dual vanities, granite countertops, and a walk-in shower with built-in bench. A split-bedroom layout ensures privacy for guests, with a secondary bedroom and full bath located at the front of the villa. The versatile den/office includes a skylight and closet, making it ideal for a home office or potential third bedroom. Tivoli Village residents enjoy a scenic setting with four spring-fed lakes, fishing opportunities, majestic oak trees, and a tranquil nature trail. The HOA provides exceptional value, covering major expenses such as property insurance, exterior maintenance (including power washing and painting), roof replacement and repairs, as well as lawn care and irrigation—delivering low-maintenance, worry-free living. Don’t miss this opportunity to own a move-in-ready villa in one of Sarasota’s most charming and conveniently located communities!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Diane Goodwin (941-706-6620)
8621 RAIN SONG RD, SARASOTA, FL 34238
$499,0002 Days on yellowkey MLS ID: A4701048
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1677 Built: 2019Monthly Fee: $521 Tax: $5,564 (2025)Community: Sunrise PreserveSpa: NoVilla
Remarks: Virtually Staged. Welcome to an exceptional opportunity to enjoy maintenance-free living in a sought-after gated community offering resort-style amenities and a serene waterfront setting. This well-appointed 2-bedroom, 2-bathroom villa also features a versatile office/den, perfect for working from home, a hobby room, or accommodating additional guests. Designed with comfort and functionality in mind, the open floor plan includes a spacious living room, a dedicated dining area, and a well-equipped kitchen with plenty of cabinet and counter space, making everyday living and entertaining effortless. The split-bedroom layout provides privacy for both homeowners and guests, while the spacious primary suite offers a relaxing retreat with an en-suite bathroom. A second full bathroom serves the guest bedroom and office area. Step outside to the screened lanai, where you'll enjoy peaceful mornings and tranquil evenings overlooking a beautiful pond. The picturesque water view creates a private and relaxing backdrop, making the lanai the perfect place to unwind with a cup of coffee or entertain friends and family. Residents enjoy an active, resort-inspired lifestyle with outstanding HOA amenities, including a clubhouse, fitness center, resort-style pool, spa, and tennis courts. The gated entrance provides added privacy and peace of mind, while the prime Sarasota location places you just minutes from world-class beaches, championship golf courses, shopping, dining, medical facilities, and the area's vibrant arts and cultural attractions. Whether you're looking for a full-time residence, seasonal getaway, or investment property, this charming home offers the perfect blend of comfort, convenience, and Florida living. Don't miss the opportunity to make this beautiful water view home your own.
Listing is courtesy of: HOMESMART (407-476-0461)
Listing Agent: Max Pshichenko (720-278-9849)
3412 TALLYWOOD CIR #7018, SARASOTA, FL 34237
$284,50038 Days on yellowkey MLS ID: A4697416
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1668 Built: 1983 Tax: $1,351 (2025)Community: Tallywood Ph 1 & 2Spa: NoVilla
Taxes:$1,351
Remarks: Welcome to Tallywood, one of Sarasota's desirable 55+ villa communities! Nestled beneath a canopy of mature trees, Tallywood extends a peaceful setting just minutes from downtown Sarasota, UTC, Lido Key, St. Armand's Circle, the Baltimore Orioles Spring Training stadium, the renovated Bobby Jones Golf Club, and the expansive 96-acre Sarasota County park featuring walking trails, recreational amenities, and ongoing enhancements. This spacious villa features the largest floor plan in Tallywood, offering nearly 1,700 square feet of living space plus a dedicated carport and private storage room. The thoughtfully designed layout includes a first-floor primary suite, a guest bedroom and full guest bath, soaring cathedral ceilings in the living and dining areas, a generously sized kitchen, and an upstairs loft that can serve as a third bedroom, home office, hobby room, or additional guest space. Abundant storage is found throughout the home. Recent improvements include hurricane-impact-rated windows and sliding glass doors throughout, a water heater approximately three years old, and most kitchen appliances replaced within the last three to six years. For additional peace of mind, a transferable home warranty is included and extends through the end of 2026. Relax in the private screened lanai, enjoy the convenience of your covered carport and storage room, and take advantage of ample guest parking nearby. Residents of Tallywood enjoy an outstanding selection of amenities, including an Olympic-size swimming pool, clubhouse, fitness center, library, community kitchen, shuffleboard courts, and an active social calendar. Offering exceptional value at $284,500, this beautifully maintained villa combines generous living space, quality updates, and an outstanding Sarasota location. Schedule your private showing today!
Listing is courtesy of: VUE REALTY, LLC (941-269-8400)
Listing Agent: Scotty Ledford (941-400-7360)
1505 LAKESIDE WAY #153, SARASOTA, FL 34232
$164,900111 Days on yellowkey MLS ID: A4689160
0 Days Off yellowkey (back on 7/25/2026)
REDUCED by $5,000 (2.9%) on 07/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1372 Built: 1976 Tax: $916 (2025)Community: Glen Oaks Ridge Villas 2Villa
Taxes:$916
Remarks: Under contract-accepting backup offers. New reduction! Large villa at very reasonable price. Offering a full living room, den and a real dining room. You'll have space for all your possessions & options for living & decorating to suit your lifestyle. The villa offers nice laminate, updated in a light color for easy care. The Florida Room is all windows and lets the Sunshine through all year. The AC in only 8 years old & the washer is newer as well. And, then there's location. Right across Circus Blvd is Bobby Jones recreational facility. Golf & walking trails with the Sarasota Lawn Bowling group included on the grounds. The GOR association offers many & a variety of activities. Should you have an interest, fun things to do. Short rides to Downtown Sarasota and to UTC Mall, Mote & restaurants for every taste. More local is a Publix & a Bealls Department store, about a mile just down the road. Beautifully priced & ready to ready to go.. Buy now while prices are at lower pace.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-556-2150)
Listing Agent: Patricia Emmett (941-685-0343)
6475 POSITANO CT, SARASOTA, FL 34243
$425,00033 Days on yellowkey MLS ID: A4697861
1 Days Off yellowkey (back on 7/25/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1495 Built: 2016Monthly Fee: $359 Tax: $4,996 (2025)Community: Villa AmalfiSpa: YesVilla
Taxes:$4,996
Elementary School: Kinnan Elementary
High School: Braden River High
Middle School: Braden River Middle
Remarks: Under contract-accepting backup offers. Beautiful 2 bedroom, 2 bath villa with office/den/flex room and 2 car garage. The Great room flowing into the kitchen is the focus of this popular floorplan, tile thoughout the living areas and crown molding throughout, white kitchen with 42" upper cabinets with crown molding, center island with Quartz countertops, grey marbled subway tile backsplash, great room features tray ceiling with crown, additional can lights, extended lanai with pavers that runs the width of the house with high-end 7 person/58 jet hot tub, custom light fixtures/fans throughout. Awesome gated community features heated pool/spa, outdoor kitchen and TV, NO CDD, low HOA fees cover roofs, paver driveways and all exterior yard maintenance. Amazing location, close to Sarasota, St Armand's, Lido & Longboat Keys, UTC Mall and lots of shopping/dining. Call today for an appointment to view!
Listing is courtesy of: KELLER WILLIAMS ON THE WATER (941-729-7400)
Listing Agent: Jen Bowman (941-840-0117)
2242 CIRCLEWOOD DR #24, SARASOTA, FL 34231
$225,00045 Days on yellowkey MLS ID: TB8517647
1 Days Off yellowkey (back on 6/18/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1176 Built: 1974Monthly Fee: $695 Tax: $1,028 (2025)Community: Woodside Village EastVilla
Taxes:$1,028
Middle School: Brookside Middle
Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to 2242 Circle Wood Drive, a beautifully maintained 2-bedroom, 2-bath villa offering the perfect blend of comfort, convenience, and maintenance-free living in one of Sarasota’s most desirable locations. Inside, you'll find spacious living areas filled with natural light, an inviting floor plan, and a beautiful sunroom/den that provides the perfect space for a home office, reading room, or additional living area. Covered parking adds everyday convenience, while the lush tropical landscaping creates a peaceful setting you'll love coming home to. The community amenities elevate the lifestyle even further with a heated pool, tennis and pickleball courts, and beautifully maintained grounds. Location is everything, and this villa delivers. You're just minutes from Siesta Key Beach, St. Armands Circle, Downtown Sarasota, world-class dining, shopping, entertainment, and golf. Whether you're looking for a full-time residence, seasonal retreat, or low-maintenance Florida getaway, this villa offers the Sarasota lifestyle you've been dreaming of.
Listing is courtesy of: ELEVE REAL ESTATE LLC (813-562-5002)
Listing Agent: Danielle Davis (813-526-5002)
5626 MONTE ROSSO RD, SARASOTA, FL 34243
$269,00013 Days on yellowkey MLS ID: A4699571
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1141 Built: 1992Monthly Fee: $332 Tax: $1,518 (2025)Community: Riviera Club Village At Longwood Run Ph 02Villa
Taxes:$1,518
Remarks: Virtually Staged. **Maintenance-Free Luxury Living in Riviera Club.** Welcome to this beautifully maintained 2-bedroom, 2-bath attached single-family home, where an open, light-filled floor plan, soaring vaulted ceilings, and tranquil POND VIEWS create an inviting retreat. The home also features valuable updates including FRESH INTERIOR PAINT throughout (2026), a newer roof (2020), exterior painting (2021), and water heater (2024), offering added peace of mind for years to come. Designed for effortless Florida living, the spacious brick-paver COURTYARD offers the perfect setting for entertaining or relaxing outdoors, while glass doors from the living room open to a PRIVATE PATIO overlooking the water. The split-bedroom layout provides comfort and privacy, complemented by a spacious primary suite featuring an en suite bath and walk-in closet, along with indoor laundry, generous storage, and a spacious TWO-CAR GARAGE. Enjoy the ease of maintenance-free living with HOA-covered exterior maintenance, roof maintenance, and lawn care. Just steps away, Longwood Park offers pickleball and tennis courts, a gymnasium, playgrounds, walking paths, and more. Perfectly positioned near premier shopping and dining by the University Town Center Mall (UTC), plenty of pristine golf clubs such as Palm Aire Country Club, Sarasota-Bradenton International Airport, downtown Sarasota, St. Armands Circle, and the world-renowned beaches of Siesta Key and Lido Key, this move-in-ready home offers the ideal blend of luxury, convenience, and the coveted Florida lifestyle. Schedule your private showing today before it’s gone!
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Dean Hinterstoisser (941-726-0314)
5103 GREENCROFT RD, SARASOTA, FL 34235
$295,000683 Days on yellowkey MLS ID: N6134516
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1487 Built: 1979Monthly Fee: $567 Tax: $3,642 (2023)Community: Vivienda At The MeadowsVilla
Taxes:$3,642
Elementary School: Gocio Elementary
Tax Year: 2023
Remarks: Resort-Style Living Maintenance-Free includes Tile Roof. One of Sarasota’s most desirable communities. This spacious 2 bedroom, 2 bath, car garage home offers multiple living areas, including a living room, open-concept kitchen/family/dining area, and tranquil greenbelt view from the lanai. Ideally positioned not direct-facing neighbors, this home boasts a generous front yard and privacy. Enjoy true ease of living—landscaping and TILE roof maintenance are covered by the HOA, with reserves in place for future care. Recent upgrades include HVAC (2021), Water Heater (2023), Washing Machine (2024), Refrigerator (2022), as well as a new kitchen faucet, range hood fan, and light (2024). The Meadows Country Club offers membership access to 54 holes of golf, 17 Har-Tru tennis courts, pickleball, a junior Olympic-size pool, fitness center, two restaurants, and over 200 annual events. Explore 14 miles of scenic walking, biking, and nature trails, all just minutes from downtown Sarasota, UTC Mall, and I75. Come home to comfort, community, and the carefree lifestyle you’ve been looking for. Resort-Style Living in The Meadows Golf & Country Club Welcome to The Vivienda, a maintenance-free enclave within The Meadows, one of Sarasota’s most desirable communities.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY (941-207-5055)
Listing Agent: Janet Linaburg (941-225-5289)
5526 CHANTECLAIRE #31, SARASOTA, FL 34235
$449,90081 Days on yellowkey MLS ID: A4689277
REDUCED by $10,100 (2.2%) on 06/08/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1838 Built: 1985Monthly Fee: $617 Tax: $2,477 (2025)Community: ChanteclaireVilla
Taxes:$2,477
Remarks: Virtually Staged. Welcome to this beautifully reimagined villa in the highly sought-after Meadows community, where timeless design meets modern sophistication. This fully renovated residence offers 2 bedrooms with a flexible third space that can serve as a private den, office, or easily function as a third bedroom tailored to fit your lifestyle. Every detail has been thoughtfully curated, showcasing a light, bright interior with an elegant, airy aesthetic. As reflected in the virtual staging, the open-concept design is complemented by clean lines, upscale finishes, and a seamless flow between living spaces perfect for both relaxed everyday living and effortless entertaining. Natural light fills the home, enhancing the soft, neutral palette and creating a warm yet refined ambiance throughout. Ideally located in The Meadows, known for its lush landscapes, walking trails, and proximity to dining, shopping, and Sarasota’s finest amenities, this residence offers the perfect balance of tranquility and convenience. Unlock exceptional living in one of Sarasota’s most desirable communities.
Listing is courtesy of: LUXEKEY REAL ESTATE LLC (941-404-3173)
Listing Agent: Robin Eekhof (941-504-1941)
4668 OAK HILL LN #40, SARASOTA, FL 34232
$280,000151 Days on yellowkey MLS ID: A4683176
REDUCED by $10,000 (3.4%) on 05/06/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1024 Built: 1985Monthly Fee: $559 Tax: $3,287 (2025)Community: Village Oaks Sec ASpa: NoVilla
Taxes:$3,287
Remarks: Your Private Sarasota Sanctuary Awaits! Discover true Florida living in this beautiful end unit villa situated on a quiet street. This 2 BR/2BA gem located in the Village Oaks Community is a breath of fresh air. Enjoy morning coffee on your screened front porch or sunsets drinks on the large rear lanai. Inside, the home features vaulted ceilings in living/dining areas and luxury vinyl plank flooring flowing throughout the main living space and bedrooms. The split-bedroom floor plan ensures maximum privacy for owners and visitors alike. The bright kitchen features stainless appliances and an eat-in nook filled with natural light. Best of all, the community pool and tennis court are just steps away from your front door! Perfectly located near UTC shopping and beautiful beaches nearby - this is the Florida lifestyle you've been searching for!
365 OAK HILL WAY #32, SARASOTA, FL 34232
$269,900192 Days on yellowkey MLS ID: A4677958
REDUCED by $10,100 (3.6%) on 07/12/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1174 Built: 1985Monthly Fee: $559 Tax: $570 (2025)Community: Village Oaks Sec BSpa: NoVilla
Taxes:$570
Remarks: Virtually Staged. Nestled in the quiet, pet friendly community of Village Oaks features this Immaculate updated 2-bedroom, 2 bathroom Condo/Villa that offers a move-in-ready retreat. This fully updated unit features a new hot water heater installed in January 2026 and boasts a freshly repainted interior throughout. The modernized kitchen offers a pass-through to the dining area. Updated Master Bath with dual sinks, and walk in shower. Enjoy the look of luxury vinyl that flows seamlessly through every room. The open-concept living room boasts of high ceilings, while an enclosed Florida room (lanai) provides a private space to enjoy the lush surroundings. The villa features a convenient in unit laundry area with a washer and dryer tucked into a dedicated laundry closet.Enjoy the convenience of a private one car garage with remote access, plus two dedicated exterior parking spots right outside your villa. Community pool overlooking lake along with tennis/pickleball court for outdoor activities. Ideally situated between I-75 and downtown Sarasota, offering quick access to the University Town Center Mall (UTC), local dining and world-class beaches.
4136 BOWLING GREEN CIR #23, SARASOTA, FL 34233
$334,90044 Days on yellowkey MLS ID: A4696926
REDUCED by $5,000 (1.5%) on 07/13/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1601 Built: 1980Monthly Fee: $463 Tax: $2,499 (2025)Community: Center Gate Village 5Villa
Taxes:$2,499
Remarks: PRICE REDUCTION!!! Discover the perfect blend of comfort, privacy, and convenience in this beautifully updated lakefront villa located in the highly sought-after Center Gate Village, a desirable 55+ community. A maintenance-free Sarasota lakefront community. This move-in ready, spacious 2-bedroom, 2-bathroom, 2-car garage villa features serene lake views from its private setting. Recent improvements in this updated home provide peace of mind and modern appeal, including updated kitchen appliances, A/C with heat pump, water heater, luxury flooring, LED track lighting, ceiling fans, bathroom fixtures and vanities, custom real wood cabinetry, and matching granite countertops in both the kitchen and bathrooms. Designed with comfort in mind, this home offers cathedral ceilings, generously sized rooms, and an inviting open floor plan that creates a bright and airy atmosphere. The spacious screened lanai is the perfect place to relax, enjoy your morning coffee, or watch the abundant wildlife on the picturesque lake. The thoughtful layout provides both privacy and functionality, making it ideal for everyday living as well as entertaining family and friends. Guests will feel right at home in this welcoming residence. Residents of Center Gate Village enjoy access to a heated community pool and a large lakeside observation deck, providing the perfect setting to socialize, relax, and enjoy Florida's year-round sunshine. Ideally located in the heart of Sarasota, this villa is just minutes from shopping, dining, medical facilities, houses of worship, Sarasota-Bradenton International Airport, world-class beaches, and spring training facilities for Major League Baseball teams. Nearby attractions include Nathan Benderson Park, renowned for world-class rowing events, and University Town Center (UTC), one of the area's premier shopping and entertainment destinations. Enjoy easy access to Tampa's professional sports venues, approximately one hour away, while Orlando's theme parks, including Disney, and the beautiful beaches and attractions of Naples are within a convenient 90-minute drive. Whether you're seeking a seasonal retreat or a year-round Florida residence, this move-in-ready lakefront villa offers the lifestyle you've been searching for.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-360-7777)
Listing Agent: Steve Zeris (941-518-6450)
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