Location: Sarasota
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5531 HAMPSTEAD HEATH #44, SARASOTA, FL 34235
$295,000126 Days on yellowkey MLS ID: A4676168
0 Days Off yellowkey (back on 4/22/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1464 Built: 1988 Tax: $2,366 (2025)Community: Hampstead HeathVilla
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,366
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Under contract-accepting backup offers. Coastal Sophistication Meets Maintenance-Free Living in The Meadows! Discover the pinnacle of Florida living in this beautifully maintained, bright end-unit villa located in the highly sought-after Meadows community. Designed for comfort and seamless indoor-outdoor living, this two-bedroom, two-bathroom home features soaring vaulted ceilings, plantation shutters, and a modern eat-in kitchen with granite countertops and upgraded appliances. The primary suite is a true sanctuary with a vaulted ceiling, walk-in closet, and a luxurious en-suite featuring a walk-in shower with a built-in bench. Enjoy tranquil mornings on the lattice-enclosed patio, or entertain on the spacious rear lanai overlooking a sprawling, peaceful backyard. Have the best of both worlds with a fully enclosed, air-conditioned lanai that easily transitions to a screened space for fresh-air living. Peace of mind comes standard with a brand new 2024 HURRICANE-RATED ROOF, freshly painted exterior, and new courtyard lattice (March 2026). Located just steps from the recently resurfaced Hampstead Heath pool, this villa offers easy access to 14 miles of trails, a fitness center, and championship golf in a 1,600-acre park-like setting. Conveniently located near UTC Mall, downtown, and beaches—select furnishings are available to make this move-in-ready retreat yours immediately!
Listing is courtesy of: ALBERT WOOSTER & COMPANY (941-350-1220)
Listing Agent: Kathleen Niedospial (941-780-2884)
2425 ASPINWALL ST #2425, SARASOTA, FL 34237
$149,900100 Days on yellowkey MLS ID: A4679117
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1024 Built: 1971Monthly Fee: $692 Tax: $2,293 (2025)Community: The Village Sec 2Spa: NoVilla
Taxes:$2,293
Elementary School: Tuttle Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Welcome to The Village. A quaint enclave of just 18 villas surrounded by mature landscaping, yet just minutes from downtown Sarasota. This 2-bedroom, 2-bath villa offers an excellent opportunity for an investor, first-time homebuyer, or winter retreat. The open great room design features tile flooring throughout, creating a bright and inviting living space. Both bedrooms include walk-in closets and en-suite bathrooms, providing comfort and privacy. The updated kitchen boasts quartz countertops and a separate island for additional workspace—perfect for cooking and entertaining. Step outside to the covered patio, where you can enjoy garden views with a partial pond backdrop. Additional highlights include a new roof in 2025 and one assigned parking space. Ideally located just minutes from Downtown Sarasota/Main Street, St. Armand's Circle, and Lido Key, you’ll have easy access to world-class dining, shopping, cultural attractions, and beautiful beaches. Whether you’re looking for a full-time residence, vacation getaway, or rental property, this delightful home offers the perfect blend of location, lifestyle, and value.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Tina Von Kessel (941-266-2848)
7754 WANING MOON WAY, SARASOTA, FL 34241
$399,999192 Days on yellowkey MLS ID: A4669060
1 Days Off yellowkey (back on 4/23/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1533 Built: 2026Monthly Fee: $448Community: Esplanade At Skye RanchVilla
Taxes:$0
Elementary School: Lakeview Elementary
High School: Riverview High
Tax Year: 2024
Middle School: Sarasota Middle
Remarks: What's Special: Close to Amenities | Close to Trails | Pond View. New Construction – Ready Now! Built by America’s Most Trusted Homebuilder. Welcome to the Ibis at 7754 Waning Moon Way in Esplanade at Skye Ranch. Step inside, you'll find 2 bedrooms, 2 bathrooms, a study, and a spacious 2-car garage. The open gathering room flows seamlessly into a beautiful kitchen, creating a bright and welcoming heart of the home. Your primary suite is a peaceful retreat, featuring a large walk-in closet, dual sink vanity, expansive shower, and a private water closet. Additional Highlights Include: 8' interior doors, extended lanai, tray ceilings package, extended patio cage with screened roof, whole house impact windows, and pre-plumbed for laundry room sink. Photos are for representative purposes only. MLS#A4669060 Live your dream vacation every day at Esplanade at Skye Ranch! Esplanade offers a vibrant, resort-style lifestyle with endless opportunities to energize your body, mind, and spirit. From the moment you arrive, you’ll experience a world of fun and relaxation, with access to the Hub, Rendezvous Park, and Turner Park and soon, The Venue! Get ready for exciting amenities like a Bahama Bar and Grill, resort-style pool, state-of-the-art fitness center, bocce ball courts, bark park, and more. With community parks, sports fields, and a pet park, Esplanade is your personal playground. Stay active, stay relaxed, and embrace a lifestyle filled with adventure, every single day!
Listing is courtesy of: TAYLOR MORRISON RLTY OF FLA (866-495-6006)
Listing Agent: Michelle Campbell (866-495-6006)
5156 MAHOGANY RUN AVE, SARASOTA, FL 34241
$345,000197 Days on yellowkey MLS ID: A4668369
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1572 Built: 1998Monthly Fee: $348 Tax: $3,550 (2024)Community: Club Homes 3Villa
Taxes:$3,550
Remarks: Welcome to Heritage Oaks Golf & Country Club, Sarasota's premiere gated, golfing neighborhood! Located in the heart of Sarasota, this community is located close to everything in the city - wonderful shopping, eclectic dining, cultural performing arts, and the country's best beaches! This wonderful Buttonwood model Club Home features 2 bedrooms, 2 bathrooms, a den/study, an attached 2 car garage, and is being sold Turn-Key Furnished. With over 1,500 square feet of living space, this thoughtfully laid-out home provides ample space and privacy for owners and their guests. The open floor plan is ideal for entertaining as the kitchen provides direct sight-lines to the living room, dining room, and outdoor space. The spacious den/study features lovely pocket doors making the space ideal as a home office, sitting room, or even a third bedroom. The slider doors bring in a ton of natural light making the home feel bright and cheerful. Common areas and the den feature wonderful ceramic tile flooring and the guest bedroom features beautiful luxury vinyl plank flooring. As a precaution, the owners have re-plumbed/re-piped this property and replaced the A/C system (2023). Simply pack up your clothes and move right in! Enjoy the views of water and the 12th tee box and fairway from your private screened lanai. You can even spend evenings watching the abundance of wildlife that thrive in this Certified Audubon Neighborhood. Heritage Oaks is known for its pristine 18-hole golf course, har-tru tennis courts, fitness center, 24-hour security, an impressive, recently renovated clubhouse with a lovely restaurant and the sensational 19th Hole Lounge, 5 swimming pools, and a calendar of events packed with activities. This property is ideal as a primary residence or seasonal retreat. Come take a look at this wonderful property!
Listing is courtesy of: ROSEBAY INTERNATIONAL REALTY, INC (941-366-7673)
Listing Agent: Doug Figgins (941-725-1060)
4737 CHANDLERS FORDE #14, SARASOTA, FL 34235
$450,00040 Days on yellowkey MLS ID: A4686909
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2050 Built: 1981 Tax: $5,094 (2025)Community: The MeadowsSpa: NoVilla
Taxes:$5,094
Elementary School: Gocio Elementary
Remarks: Welcome to Chandlers Forde in The Meadows—a neighborhood surrounded by mature trees and the peaceful feel of an enchanted forest. This beautifully renovated villa-style condo with 2 car garage offers ultimate privacy with a wooded view and a glimpse of the golf course beyond. This 2-bedroom, 2.5-bath home with a den (which can easily be converted into a third bedroom) has been tastefully updated from top to bottom. The home has a cozy yet elegant feel, with soaring ceilings and a grand double-sided stone fireplace that serves as the centerpiece of both the living and dining rooms. The living room is extra spacious, with tranquil views of the trees—an ideal space for hosting or simply relaxing by the fire. The kitchen was completely UPDATED in 2023–2024, featuring leathered granite countertops, custom cabinetry, premium appliances including Bosch, and an oversized chef’s prep sink. A custom coffee counter and the addition of a dry bar with wine fridge between the dining room and living room make the space perfect for entertaining. Just off the living room and primary suite is a Florida room—perfect for al fresco dining, morning coffee, or relaxing after a long day. With electric already in place, it’s ready for your new hot tub. The main-floor primary bedroom is expansive and elegant, featuring a walk-in closet crafted by CLOSETS BY DESIGN for maximum organization. The ensuite bath feels like a private spa, offering quartz countertops, a walk-in shower with custom glass door, and serene finishes throughout. The main floor also includes a RENOVATED half bath (2024) and a laundry area with washer and dryer hookups for convenience. Upstairs is illuminated by an elegant mid-century modern chandelier and large hurricane-impact windows that invite in an abundance of natural light. The open den/office space w/ built-in closet can easily serve as a third bedroom. A guest bedroom with vaulted ceilings overlooks the trees, an updated guest bath with quartz countertops, a tub-shower combination, and extra closet space rounds out the second floor. Beyond the beauty, this home offers peace of mind. All windows and exterior sliders are HURRICANE-IMPACT RATED The cast iron waste pipes have been replaced with PVC, electrical hookups have been added for the included generator, AND EV CHARGER. Additional upgrades include, reverse osmosis system at the kitchen sink and refrigerator, whole-house water softener, two new AC units (2018) with duct cleaning in 2024, and GE front-loader washer and dryer (2023) and the ROOF was replaced in 2022. In Chandlers Forde, residents enjoy two private pools, while The Meadows offers a lifestyle unlike any other in Sarasota with 14 miles of walking and biking trails winding through over 1,650 acres of mature landscaping, ponds, and natural preserves. For a small fee there is access to a state-of-the-art fitness center, JR Olympic pool, golf, tennis, and 10 pickleball courts. The community also includes a dog park and an active social calendar hosted by the community center. Ideally located between downtown Sarasota and University Town Center, The Meadows places you 5 minutes from UTC, Benderson Park, the new Mote Marine campus, fine dining, and shopping, 15 Minutes to Sarasota’s downtown cultural offerings—including the symphony, opera, ballet, and locally owned restaurants and 20 minutes to St Armands circle and award winning beaches. This stunning home combines luxury, comfort, and nature—truly a place to call home.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Laura Way (941-321-6449)
2316 BLUE MAHOE LN, SARASOTA, FL 34240
$488,9908 Days on yellowkey MLS ID: A4691035
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1530 Built: 2026Monthly Fee: $245 Tax: $848 (2025)Community: Windward At Lakewood Ranch Phase 2Spa: NoVilla
Taxes:$848
Elementary School: Tatum Ridge Elementary
Middle School: McIntosh Middle
Remarks: The Tidewater 2B twin villa by Neal Communities offers two bedrooms, two baths, and a spacious open layout designed for comfortable living. The main living area seamlessly connects the great room, dining space, and kitchen with an island, creating an inviting setting for gathering and entertaining. A private den adds flexibility for a home office, hobby room, or additional living space. The covered lanai provides a comfortable outdoor area for relaxing or enjoying fresh air. Inside, tile and wood flooring enhance the home’s stylish appeal, complemented by a neutral color palette that creates a timeless and cohesive design throughout. The owner’s suite features dual closets and a well-appointed bath with double vanities, a walk-in shower, and private water closet. A secondary bedroom with a walk-in closet and nearby full bath provides comfort and convenience for guests or family members.
Listing is courtesy of: NEAL COMMUNITIES REALTY, INC. (941-328-1111)
Listing Agent: John Neal (941-313-8575)
3806 ROXANE BLVD #161, SARASOTA, FL 34235
$244,000136 Days on yellowkey MLS ID: A4675238
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1195 Built: 1964Monthly Fee: $472 Tax: $1,333 (2024)Community: Strathmore Villa Sec 09Villa
Taxes:$1,333
Remarks: Welcome to a most charming 2 bedroom, 2 bathroom home in Strathmore Villas. This home is located in a 55+ community and has countless beautiful updates making it completely move in ready for you! This cozy community is located close to endless dining options and luxury shopping at University Town Center Mall, endless recreation options at Nathan Benderson Park, golf at the newly reopened and completely refurbished Bobby Jones Golf Course just across the street. Minutes to world-class Gulf of Mexico powder sand beaches and the cultural destination of downtown Sarasota. Community center for parties and meetings, gorgeous heated community pool to meet neighbors and enjoy a happy hour libation in the sun.This villa is free-standing on a private cul-de-sac and has great curb appeal and inviting outdoor gardening and seating areas. Greeted by an oversized carport with a covered outdoor seating area, you enter through a welcoming alcove offering a private entrance. A soothing coastal palate creates a peaceful living space with wood-textured ceramic tile floating throughout for a cohesive foundation. The beautifully renovated kitchen offers white cabinetry, granite counters, and gorgeous sea blue glass subway tile backsplash. Stainless appliances including convection oven and ample counter space to please the home chef. A natural wood ceiling inset detail rounds out the seaside vibe. The kitchen also offers a breakfast bar and an eat-in area for cozy morning coffee or an additional work-from-home office space. The living room is bright and open with loads of natural light. The split bedrooms offer privacy for guests and the primary bedroom has an updated en-suite bathroom with a step-in shower, new vanity with granite top, new lighting and a walk-in closet. The full guest bathroom is also completely updated with new shower/tub combo, vanity, lighting, and fixtures. This home provides peace of mind with new hurricane impact windows throughout. Interior freshly painted, kitchen has new electrical and plumbing to bring it to current code. The full size washer and dryer were replaced in 2022 and are located in the laundry room with storage area across from the front door behind the carport along with the hot water heater. Maintenance-free Florida lifestyle at its best!
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Terry Hayes (941-302-3100)
3924 ASHWOOD LN #59, SARASOTA, FL 34232
$188,00026 Days on yellowkey MLS ID: N6143712
REDUCED by $11,000 (5.5%) on 04/22/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1332 Built: 1973Monthly Fee: $685 Tax: $1,781 (2025)Community: Glen Oaks Ridge Villas 1Villa
Taxes:$1,781
Remarks: Now offered at a newly improved price, this 2-bedroom, 2-bath villa presents an outstanding opportunity in a highly desirable 55+ community, combining value, location, and low-maintenance living. This light and bright home features an open living and dining area plus a versatile den ideal for a home office, hobby room, or additional guest space. The enclosed Florida room provides year-round enjoyment and added living space, perfect for relaxing or entertaining. A private laundry room with utility sink and extra storage adds convenience. Recent updates provide peace of mind and enhance overall appeal. The spacious primary suite includes a walk-in closet and an en-suite bathroom with an accessible shower. The guest bedroom is well-suited for visitors while maintaining flexibility for everyday use. Residents enjoy resort-style amenities including a heated pool, fitness center, clubhouse, shuffleboard, library, and an active social calendar. This welcoming community offers a true Florida lifestyle with strong neighbor connections. Located just minutes from downtown Sarasota, Siesta Key Beach, shopping, dining, hospitals, and arts and culture. Bobby Jones Golf Club is just blocks away, featuring a recently renovated course and modern facilities. Ideal as a full-time residence, seasonal home, or investment opportunity, this villa delivers exceptional value at its new price point in one of Sarasota’s most convenient locations.
Listing is courtesy of: HOMESMART (407-476-0461)
Listing Agent: Scott Swonger (941-600-3534)
5474 RIVERBLUFF CIR #V35, SARASOTA, FL 34231
$219,900189 Days on yellowkey MLS ID: A4669393
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1120 Built: 1971 Tax: $2,363 (2024)Community: Strathmore Riverside IVilla
Taxes:$2,363
Elementary School: Phillippi Shores Elementary
Middle School: Brookside Middle
Remarks: Welcome to Strathmore Riverside Villas, a vibrant 55+ community perfectly situated in the heart of Sarasota. This spacious two-bedroom, two-bath villa offers the ideal blend of comfort, convenience, and endless potential. Light, bright, and airy, the home features an open-concept layout with generous room sizes and an inviting flow throughout. The enclosed lanai, complete with both windows and screens, provides a wonderful year-round living space; perfect for morning coffee, relaxing afternoons, or entertaining friends. The villa also includes a one-car carport and a separate storage and laundry area, offering privacy, security, and plenty of extra space. With just a touch of personalization, this residence can truly shine. The community itself is beautifully maintained and lushly landscaped, creating a serene and welcoming atmosphere surrounded by green space. Strathmore Riverside Villas is known for its active lifestyle and warm sense of community. Residents enjoy a wealth of amenities, including a heated geothermal pool overlooking the marina, clubhouse, fitness center, library, meeting rooms, sauna, and billiards. There’s always something happening here; social events, card games, bingo nights, potlucks, concerts, dancing, and more. Boat docks are available on a first-come, first-served basis for just $1,344 per year, and the community is pet-friendly. The location couldn’t be better; just minutes from shopping, hospitals, and the world-famous Siesta Key Beach, as well as the rich cultural attractions of downtown Sarasota, including opera, ballet, symphony, and live theatre. Whether you’re looking for a full-time residence or a seasonal getaway, this villa lives like a single-family home and offers the perfect opportunity to enjoy Florida’s relaxed coastal lifestyle. Don’t wait; schedule your private tour today and discover the charm of Strathmore Riverside Villas.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Rachelle Golden (941-538-8998)
5103 GREENCROFT RD, SARASOTA, FL 34235
$295,000595 Days on yellowkey MLS ID: N6134516
0 Days Off yellowkey (back on 3/20/2026)
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
Tax Year: 2023
Remarks: Under contract-accepting backup offers. PRICE IMPROVEMENT! 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. This spacious 2 bedroom, 2 bath home offers multiple living areas, including a living room, open-concept kitchen/family/dining area, and a lanai with tranquil greenbelt views. Ideally positioned within the community, this home boasts a generous front yard and privacy with no direct-facing neighbors across the street. 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.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY (941-207-5055)
Listing Agent: Janet Linaburg (941-225-5289)
5345 PAMELA WOOD WAY, SARASOTA, FL 34233
$219,000458 Days on yellowkey MLS ID: A4637875
REDUCED by $20,000 (8.4%) on 04/21/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1379 Built: 1989Monthly Fee: $580 Tax: $2,839 (2024)Community: 7774-Crestwood VillasVilla
Taxes:$2,839
Remarks: This 1,379 sq ft Villa (duplex ) is move-in ready, offers 2 bedrooms, 2 full bathrooms, a 1 car garage and driveway for additional parking. Crestwood Villas community is situated in Center Gate area of Sarasota, making it a prime location with substantial potential as a primary residence, vacation/seasonal resort or as an addition to your investment/rental portfolio. Create your next dream project here. Upon entering you are drawn to the expansive open concept floor plan, high vaulted ceilings, and flowing floor plan, you'll see the potential the property offers. The living/dining combo attaches to the family room and then goes to the back of the property with sliders that continue out to the covered patio and screened lanai. The kitchen is considered a "galley" design with plenty of cabinets, counter space and storage on both sides. The washer/dryer, utility closet, pantry and access to the garage are convenient to the kitchen entryway. The primary bedroom easily accommodates a king-sized bed. Notable location & convenience here. The community pool is perfect to entertain groups, enjoy gatherings with family, friends and enjoy community events. Crestwood Villas is located within close proximity to Sarasota & Manatee County's most desirable cultural events, flourishing economic growth/development and the booming vacation destination of travelers, yet tucked away from the crowds. Convenient to major transportation (I75, University Pkwy, Rt 41), nationally rated golf courses, fishing, boating, UTC Mall, Tesla, IMG Academy, Downtown Sarasota, SRQ/TPA, Medical Centers for Specialized and Senior Care, top rated schools, parks and recreation. Brand new HVAC system and carpet installed in 2025!
Listing is courtesy of: SVN COMMERCIAL ADVISORY GROUP (941-387-1200)
Listing Agent: Larry Starr (941-914-6869)
7128 W COUNTRY CLUB DR N, SARASOTA, FL 34243
$299,90055 Days on yellowkey MLS ID: A4685172
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1832 Built: 1973 Tax: $3,212 (2025)Community: Palm-Aire At Desoto Lakes Country ClubVilla
Taxes:$3,212
Elementary School: Kinnan Elementary
High School: Braden River High
Middle School: Braden River Middle
Remarks: Fully Furnished Palm Aire Home with Sunroom, Golf Course Views & Oversized Garage ! Welcome to a beautifully maintained residence in the highly desirable Palm Aire golf community, where comfort, space and a relaxed Florida lifestyle come together. This spacious three-bedroom, two-bath home offers over 1,800 square feet of living space and is being offered fully furnished, making it a truly move-in ready opportunity for seasonal or year-round living. From the moment you arrive, the inviting paver entry walkway and private courtyard create a warm first impression. Inside, the home features a bright and open layout with generous living and dining areas, neutral tile flooring throughout much of the home, and large sliding glass doors that allow natural light to fill the space. One of the standout features of this property is the expansive air-conditioned sunroom, created from the original lanai. Lined with walls of windows overlooking the spacious backyard, this versatile space is perfect for entertaining, relaxing with a book, hosting guests, or enjoying morning coffee while taking in the peaceful surroundings. The kitchen is clean, functional and well maintained, featuring updated appliances and plenty of cabinet storage. Both bathrooms have been beautifully updated in recent years with modern tile work, new vanities and walk-in showers, providing a fresh and comfortable feel. The home offers a flexible three-bedroom layout including a unique suite configuration that provides additional privacy and space for visiting family, guests or a home office setup. For those who appreciate storage and functionality, the oversized two-car garage is a rare bonus and includes additional space for a golf cart. A dedicated laundry and utility room adds even more convenience. Located directly across the street from the golf course, the home enjoys scenic views and the peaceful ambiance that Palm Aire is known for. Residents love the mature landscaping, wide open green spaces and optional membership opportunities at Palm Aire Country Club. Adding even more appeal is the maintenance-free lifestyle this community offers. Residents enjoy access to two community pools, a clubhouse, shuffleboard courts and beautifully maintained grounds, allowing you to spend more time enjoying Florida living and less time worrying about upkeep. The location is truly exceptional. Situated between downtown Bradenton and downtown Sarasota, this home offers convenient access to both vibrant city centers. Lockwood Commons shopping and dining are just minutes away, along with the growing 44th Avenue corridor that connects quickly to Lakewood Ranch, University Town Center, Sarasota-Bradenton International Airport and the stunning Gulf Coast beaches. Whether you are looking for a seasonal retreat, a comfortable full-time residence or a home where guests can easily visit and stay, this property offers the perfect combination of space, location and lifestyle. Schedule your private showing today!
Listing is courtesy of: KW SUNCOAST (941-792-2000)
Listing Agent: Ronald Pepka (941-877-1488)
5099 FLAG ST, SARASOTA, FL 34232
$499,00087 Days on yellowkey MLS ID: A4680473
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1647 Built: 2017Monthly Fee: $345 Tax: $5,291 (2025)Community: Enclave At Forest LakesVilla
Taxes:$5,291
Elementary School: Wilkinson Elementary
High School: Sarasota High
Remarks: A beautiful, rare corner-unit, single-story residence in the gated Enclave at Forest Lakes, ideally located in the heart of Sarasota. This meticulously maintained home offers privacy, natural light, and an open layout designed for effortless living, all just minutes from Siesta Key Beach, downtown Sarasota, major highways, shopping, dining, and everyday conveniences. Featuring 2 bedrooms, a dedicated office/den with double French doors, and 2 bathrooms, the home showcases over $60,000 in builder upgrades. Interior highlights include 9-foot ceilings, 8-foot paneled doors, rich hardwood flooring throughout, and stylish tile in both bathrooms. The chef’s kitchen is a standout with light cabinetry, pull-out storage features, quartz countertops, a large island with a breakfast bar, stainless steel appliances, and a marble backsplash. The primary suite serves as a private retreat with a tray ceiling and a spa-like bath offering a walk-in shower, dual sinks, quartz counters, and ample storage. The great room opens to a full-width covered and screened lanai with remote-controlled fans and ceiling speakers, creating an ideal indoor-outdoor living space. Residents enjoy maintenance-free living with access to a heated resort-style pool, pavilion, dog park, and nearby Legacy Trail access. This corner-unit home combines luxury, privacy, and a central Sarasota location that puts beaches, culture, recreation, and shopping all within easy reach.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-556-2150)
Listing Agent: Ellen Wilson (704-651-6322)
7755 PINE TRACE DR #7755, SARASOTA, FL 34243
$379,90010 Days on yellowkey MLS ID: A4690016
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1605 Built: 1988 Tax: $4,683 (2025)Community: Pine TraceVilla
Taxes:$4,683
Remarks: Fully Furnished | Turnkey Living in Palm Aire's Pine Trace. Welcome to 7755 Pine Trace Drive a beautifully maintained, fully furnished 3-bedroom, 2-bathroom residence offering 1,605 square feet of effortless Florida living in one of Sarasota's most desirable communities. Step inside to an open-concept living area that's move-in ready and thoughtfully appointed for both everyday comfort and easy entertaining. The modern kitchen features contemporary appliances and generous counter space ideal for anyone who loves to cook and gather. Three well-sized bedrooms provide private retreats for family or guests, and the attached 2-car garage delivers both secure parking and valuable storage. Extensively Updated in 2024: New A/C, refrigerator, stove, microwave, garbage disposal, garage door, washer, dryer, lighting, ceiling fans, blinds, and a brand-new steam room in the pool area. Roof replaced in 2021. This home has been meticulously cared for buy with confidence. The Pine Trace Community offers a tranquil, beautifully landscaped setting with a friendly neighborhood feel. Nearby Palm Aire Country Club is a private, member-owned equity club featuring golf, tennis, padel, pickleball, visual arts programming, food and wine events, gardening groups, and active social card clubs. Four equity membership options are available. Location is everything. Minutes from University Town Center with 100+ specialty stores and 20+ restaurants. Easy access to downtown Sarasota's acclaimed dining scene, Sarasota Opera House, and world-class cultural destinations including The Ringling Museum. Beach days are just a short drive to Lido Key's white sand shores, St. Armands Circle shopping and dining, or legendary Siesta Beach consistently ranked among the best beaches in the country. Comfort, convenience, and the best of the Sarasota lifestyle all waiting for you at Pine Trace.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Brandy Loebker (941-404-4737)
5370 MYRTLE WOOD #56, SARASOTA, FL 34235
$209,900146 Days on yellowkey MLS ID: A4674030
REDUCED by $15,000 (6.7%) on 04/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1080 Built: 1981 Tax: $2,969 (2024)Community: SomersetVilla
Taxes:$2,969
Elementary School: Emma E. Booker Elementary
Remarks: New Improved Price!! This stunning end-unit villa offers the perfect blend of modern comfort and convenient location in The Meadows just outside of Sarasota's desirable University Town Center area. With two bedrooms and two bathrooms spread across 1,080 square feet, this well-appointed home features freshly installed white shaker kitchen cabinets paired with elegant stone countertops that'll make your morning coffee routine feel like a luxury experience. Natural light floods the space through thoughtfully positioned windows, while vaulted ceilings create an airy, spacious atmosphere that makes entertaining a breeze. Updated modern ceiling fans and light fixtures add contemporary flair throughout, and the partially furnished setup means you can move in and start living the good life immediately. Step outside to the rear screened-in lanai – perfect for enjoying your morning coffee or unwinding after a long day in true Florida fashion. The community heated pool is just a short walk away, while the convenient carport includes extra storage space ideal for bikes and outdoor gear. The end-unit positioning provides added privacy and natural light, making this feel more like a house than a typical villa. Location-wise, you've hit the jackpot. The nearby University Town Center Mall corridor offers abundant shopping and dining, while Nathan Benderson Park, the Mote Science Education Aquarium, and PopStroke provide endless entertainment. Downtown Sarasota and pristine area beaches are just a comfortable twenty-minute drive away. This property presents an excellent opportunity for both primary residence and rental income potential, given its prime location and move-in ready condition.
Listing is courtesy of: STERLING REALTY (941-379-5810)
Listing Agent: Shaun Cumston (941-737-3539)
5354 MYRTLE WOOD #50, SARASOTA, FL 34235
$247,000107 Days on yellowkey MLS ID: A4677059
REDUCED by $8,900 (3.5%) on 04/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1064 Built: 1981Monthly Fee: $592 Tax: $2,906 (2024)Community: SomersetSpa: NoVilla
Taxes:$2,906
Remarks: NEW PRICE- Welcome to a move-in-ready villa offering effortless Florida living in one of the most sought-after enclaves within The Meadows—where tree-lined streets, mature landscaping, and an active outdoor lifestyle define the experience. Perfectly positioned on a quiet street just moments from community pools and miles of scenic trails, this residence delivers both privacy and immediate access to everything that makes The Meadows so desirable. Inside, vaulted ceilings and an open, light-filled layout create an inviting sense of space, while recent updates—including fresh interior paint and new flooring—provide a clean, modern feel with minimal effort required. The great room seamlessly opens through a full wall of sliding glass doors to a screened lanai surrounded by lush greenery—an ideal setting for morning coffee or a relaxed evening. The kitchen offers a functional and stylish workspace with stone countertops, stainless steel appliances, ample storage, and its own access to a private front lanai. The split-bedroom floor plan enhances comfort and flexibility, with a private primary suite tucked at the rear of the home featuring dual closets and a walk-in shower. A second bedroom with an ensuite bath at the front provides an ideal space for guests or a home office. A dedicated laundry area adds to the home’s practical design. Living in The Meadows means enjoying a 1,650-acre park-like community with over 14 miles of trails, 85 lakes, and optional memberships to golf, tennis, pickleball, a junior Olympic pool, and a fitness center. Just minutes from Nathan Benderson Park, the vibrant shopping and dining at University Town Center, downtown Sarasota, and the renowned beaches of Siesta Key and Lido Key, this villa offers the ideal balance of convenience, lifestyle, and value—whether as a full-time residence or seasonal retreat. Make an appointment to see this villa today.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Andy Scherer (315-264-0944)
4120 MARSEILLES AVE #3268, SARASOTA, FL 34233
$250,000188 Days on yellowkey MLS ID: A4669250
REDUCED by $5,000 (2.0%) on 04/21/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1404 Built: 1993 Tax: $2,226 (2024)Community: Casa Del Sol Sec ViVilla
Taxes:$2,226
Elementary School: Ashton Elementary
Remarks: Brand new interior photos with professional staging are now available, giving you the perfect opportunity to envision life in this inviting space. Welcome to Casa Del Sol, a gated and beautifully maintained community in the heart of Sarasota, where comfort and convenience come together effortlessly. This spacious 2-bedroom, 2-bathroom villa with a den and 2-car garage offers an open, airy layout with vaulted ceilings and tile flooring throughout. Natural light fills the main living areas, creating a bright and welcoming atmosphere from the moment you step inside. The living and dining spaces flow seamlessly into a sunny Florida room, an ideal spot to unwind while enjoying peaceful landscaped views. The kitchen is well-equipped with stainless steel appliances, ample cabinet storage, and generous counter space, making it both functional and ready for everyday living or entertaining. While the home is move-in ready, it also presents a great opportunity to add your own style with modern updates over time. The primary suite feels like a private retreat, featuring a bay window that brings in soft natural light, a walk-in closet, and an ensuite bathroom with dual sinks. A thoughtfully positioned second bedroom and full bath provide comfort and privacy for guests. The versatile den adds flexibility for a home office, reading room, or hobby space. Residents of Casa Del Sol enjoy a true lifestyle community with a resort-style clubhouse, fitness center, heated pool, tennis and pickleball courts, shuffleboard, and scenic walking paths along the lakes. Located just minutes from I-75, UTC shopping and dining, downtown Sarasota, and Siesta Key Beach, this home places you close to everything that makes the area so desirable. This is a wonderful opportunity to enjoy easy, low-maintenance living in one of Sarasota’s most convenient and welcoming communities.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Toni Zarghami (941-248-2147)
4238 CARRIAGE DR #46, SARASOTA, FL 34241
$319,00013 Days on yellowkey MLS ID: A4689666
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2000 Built: 1978 Tax: $3,559 (2025)Community: Knolls The, Bent TreeVilla
Taxes:$3,559
Remarks: One or more photo(s) has been virtually staged. Charming 3-bedroom, 2-bath free-standing villa with a 2-car garage in the highly desirable Knolls of Bent Tree. This home offers a split-bedroom floor plan, a large eat-in kitchen, formal dining room, and a sunken living room that adds character and charm. The inviting Florida room is the perfect place to relax and enjoy your morning coffee. The Knolls of Bent Tree features just 52 individual free-standing homes on a private road, with no age restrictions. This villa is move-in ready and offers great potential for your personal updates and touches. Ideally located just 2 miles east of I-75, you’ll have quick and easy access to shopping, dining, golf, and all that Sarasota has to offer. Easy to show.
Listing Agent: Lisa Bouck, Pa (941-374-0165)
4239 CARRIAGE DR #36, SARASOTA, FL 34241
$394,000269 Days on yellowkey MLS ID: A4660607
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1382 Built: 1978 Tax: $1,323 (2024)Community: Knolls The,Bent TreeVilla
Taxes:$1,323
Remarks: "Buy the Location, We'll Include the Villa!" Tucked away on a private cul-de-sac in the sought-after Knolls of Bent Tree, this beautifully updated and impeccably maintained 2-bedroom, 2-bath villa offers the best of peaceful Florida living. Enjoy serene views of an expansive greenbelt and gentle stream from your enclosed, air-conditioned lanai—your own private sanctuary frequented by cranes, deer, and other friendly wildlife. Inside, you’ll find a formal living and dining room, an updated eat-in kitchen, and two spacious bedrooms, including a primary suite with ensuite bath and skylight. The villa also features an attached 2-car garage and sits within a quiet, well-kept community of just 52 freestanding villas and townhomes. This is one property you truly must see to appreciate. Superb setting, thoughtful updates, and move-in ready comfort—all in one rare find. Home has PGT Impact Windows, house water lines repipe (2019), ceiling insulation upgraded to R36, new A/C (2025), new water heater (2025), exterior painted (2025), roof (2013) And MORE GREAT NEWS, the association has just reduced the quarterly fee by $150.00
5521 CHANTECLAIRE #21, SARASOTA, FL 34235
$339,50060 Days on yellowkey MLS ID: A4684320
REDUCED by $5,000 (1.5%) on 04/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1838 Built: 1985 Tax: $3,913 (2025)Community: ChanteclaireVilla
Taxes:$3,913
Remarks: WELCOME HOME TO AN AMAZING OPPORTUNITY to live in this wonderful 3 BEDROOM, 2 BATH Bright and Spacious Villa nestled in the well- established Villas of Chanteclaire Community located The Meadows Golf and Country Club. This villa offers the new buyer exciting opportunities to creatively update the current floor---a wonderful opportunity to your personal taste or simply just enjoy the decor 'as is'. Enjoy discovering the best use the tiled sunroom, lined with windows overlooking the garden area! The Villas' Roof is less than two years old. NO CCD Fee. Enjoy many miles of trail to walk, hike or bike. Fun for all to choose from. Located a short drive to University Town Center and the commercial surrounding areas designed for shopping, entertainment, and recreational pastimes of your choosing. So much fun close by. Year-round entertainment indoors and outside for local residents and for visitors alike. Oh, and do experience the NEW World Class Mote Marine Seaquarium.
Listing Agent: Jackie Woods (941-356-4093)
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