Mid Town Sarasota Homes with Private Mailbox Exterior Features

Mid Town Sarasota Homes with Private Mailbox Exterior Features

Welcome to Midtown Sarasota, a vibrant and charming neighborhood nestled in the heart of Sarasota, Florida. Known for its lush landscapes and friendly atmosphere, Midtown offers a unique blend of suburban tranquility and urban convenience. Residents enjoy easy access to the stunning Gulf Coast beaches, cultural attractions, and a variety of dining and shopping options that make Sarasota a sought-after destination.

Midtown Sarasota is characterized by its diverse architectural styles, showcasing homes that reflect both modern and traditional designs. One of the standout features of many homes in this area is the private mailbox, which adds a touch of elegance and personalization to your property. These charming exterior features not only enhance curb appeal but also provide a sense of community and pride among neighbors. Imagine stepping outside to retrieve your mail from a beautifully crafted mailbox, surrounded by the lush greenery and warm Florida sunshine.

The neighborhood is well-connected, with major roadways providing easy access to downtown Sarasota and nearby attractions such as the Ringling Museum of Art and the Marie Selby Botanical Gardens. Families will appreciate the proximity to quality schools and parks, making it an ideal place to raise children.

Whether you're looking for a cozy bungalow or a spacious family home, Midtown Sarasota offers a variety of options to suit your lifestyle. Embrace the warmth and charm of this delightful community, where your dream home awaits! Explore the possibilities in Midtown Sarasota, and experience the best of Florida living.

Newest Mid Town Sarasota Homes with Private Mailbox Exterior Features

$440,000
3 Beds ⋅ 2 Baths ⋅ Ringling Park SubDv. ⋅ 34237 Zip Code
Virtually Staged. Welcome to Ringling Park, where mid-century modern character, a spacious corner lot, and a location just minutes from Downtown Sarasota come together in a home filled with personality. A large banyan tree creates a memorable first impression, while a brick-paver courtyard entrance welcomes you into this 3-bedroom, 1 full and 1 half bath home. Inside, signature mid-century details include dark terrazzo flooring, transom windows, and an abundance of natural light. At the front of the home, the living room is centered around a distinctive fireplace, while the kitchen features white cabinetry, dark countertops, a subway tile backsplash, and generous storage. Beyond the kitchen, the spacious dining area offers a vaulted, beamed ceiling and French doors opening directly to the backyard, creating an easy connection between indoor and outdoor living. The fully updated main bathroom features large-format tile and a glass-enclosed walk-in shower. The primary bedroom offers a walk-in closet with built-in organization, direct backyard access, and a conveniently located half bath within the primary bedroom area. An interior laundry closet adds everyday functionality. Outside, the fenced backyard is surrounded by established tropical landscaping with brick-paver patios, deck areas, and plenty of room to relax, garden, or entertain. A substantial detached, air-conditioned flex space with LVP flooring and a mini-split was previously used as an art studio and offers versatility for storage, hobbies, creative pursuits, or a setup tailored to your needs. Weekly short-term rentals are permitted, adding another possibility for investors. With Downtown Sarasota, Payne Park, restaurants, shopping, arts, entertainment, and the city's vibrant Gulf Coast lifestyle all within easy reach, this Ringling Park home offers a distinctive blend of mid-century character, flexible spaces, and an exceptional Sarasota location. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

2488 Davis Boulevard, Sarasota
$425,000
4 Beds ⋅ 2 Baths ⋅ Lake Ridge SubDv. ⋅ 34237 Zip Code
Non-comforming income property. 4 Bedrooms 3 baths, outside kitchen Private fence a lot potential. Main house is 2 Bedrooms and 1 Bath , Mother in law is 1 bedroom 1 bath and small kitchen, it also has an studio The 3 units with separate entrances and plenty of space for parking.

3100 Lake Ridge Drive, Sarasota
$675,000
3 Beds ⋅ 2 Baths ⋅ Paver Park Estates SubDv. ⋅ 34237 Zip Code
Turn-key pool home and proven income property, minutes from downtown Sarasota. Completely remodeled down to the studs and currently operating as a Successful Short-Term Rental, this 3-bedroom, 2-bath home with a den comes fully furnished and ready for you to move in, keep it running as a short-term rental, or both. This isn't a cosmetic flip — the systems are new. The home was fully replumbed from the street in (water and sewer), completely rewired with a new electrical panel, switches, and outlets, and fitted with a new AC unit and ductwork, a new water heater, and a new flat roof. New exterior doors and sliding glass door, and updated windows in the primary bedroom. Inside, the kitchen was totally renovated with new cabinetry, an induction range, and new appliances. Both bathrooms were gut-renovated to the studs. New bamboo hardwood flooring runs throughout, finished with all-new lighting fixtures and ceiling fans. The flexible den works as a home office, fourth sleeping space, or media room — a plus for rental bookings. Inside laundry room. Out back is the feature that sets this home apart in the neighborhood: a large in-ground heated pool, fully resurfaced with a new multicolor LED light, new variable-speed pump, and all-new paver deck, on a fully fenced lot with a storage shed. A covered carport and long driveway park three cars off the street. Located inside Sarasota city limits — where short-term rentals are permitted — with no HOA, no deed restrictions, and not in a FEMA flood zone. Steps from the Legacy Trail, and a short drive to downtown, Siesta Key, Southside Village, Sarasota Memorial, and Ed Smith Stadium. Zoned for Alta Vista Elementary and Sarasota High. Furnishings, bookings, and rental history convey — buy a business that's already running, or a home where the hard work is already done.

2667 Cheryle Lane, Sarasota
$640,000
6 Beds ⋅ 6 Baths ⋅ 0000 - Not Part Of A Subdivision SubDv. ⋅ 34237 Zip Code
Rare Find Sarasota duplex opportunity with a private swimming pool and exceptional flexibility for investors, multigenerational living, or an owner-occupant looking to generate rental income! Tucked away on a quiet cul-de-sac, 1213/1215 Benedict Ct offers two spacious units with a total of 6 bedrooms and 6 full bathrooms. Each unit features 3 bedrooms and 3 full baths, with every bedroom having access to its own full bathroom—an ideal layout for privacy, guests, extended family, or rental use. The property also offers mother-in-law suite functionality with a kitchenette for additional flexibility. One unit has been beautifully renovated, including an extensively renovated kitchen in approximately 2020, and is being offered fully furnished for a potential turnkey rental opportunity. Seller represents roof was replaced in approximately 2020; buyer to verify permitting, age, and condition. Enjoy the Florida lifestyle with a private swimming pool and patio area perfect for relaxing and entertaining. Additional highlights include two separate addresses and a versatile duplex configuration. Conveniently located near Downtown Sarasota with easy access to shopping, dining, entertainment, and Sarasota's world-famous Gulf Coast beaches. The property offers excellent potential for traditional, furnished, or short-term vacation rental use, subject to applicable City of Sarasota requirements. Live in one side and rent the other, accommodate extended family, or add a versatile Sarasota income property to your portfolio. Buyer and buyer's agent to verify room configuration, permitting, rental requirements, measurements, and all information deemed important to buyer.

1213 Benedict Court, Sarasota
$369,900
3 Beds ⋅ 1 Baths ⋅ Lockwood Gardens SubDv. ⋅ 34237 Zip Code
Sarasota Pool Home with NO HOA and Major Recent Updates! A screened pool, a spacious fenced backyard, no HOA, and several major recent improvements make this three-bedroom Sarasota home an especially appealing find. Inside, the home features a comfortable living area with crown molding, tile and laminate wood flooring, and a bright kitchen with quartz counters, white cabinetry, stainless steel appliances, recessed lighting, generous counter space, and a large island/breakfast bar. The screened swimming pool offers plenty of surrounding deck space for relaxing, dining, and entertaining. Beyond the pool enclosure, the expansive fenced backyard provides even more room for pets, gardening, recreation, or creating your own outdoor retreat. Several important improvements have already been completed, including a new A/C system in 2025, water main and backflow system in 2026, and roof in 2019. The refrigerator and dryer were also replaced in 2026. An attached one-car garage provides additional storage and everyday convenience. Conveniently located near Downtown Sarasota, the home offers easy access to shopping, dining, entertainment, parks, and the area’s many cultural attractions. Whether you are purchasing your first home, downsizing, or simply looking for a Sarasota pool home without HOA restrictions, this property offers comfort, convenience, and plenty of room to enjoy the Florida lifestyle.

3338 Bailey Street, Sarasota
$149,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
OAKWOOD MANOR — WHERE FUN AND FRIENDSHIPS BEGIN! FRESH, UPDATED, AND READY TO ENJOY! NEW KITCHEN**NEW BATHS** NEW FLOORING** NEW LOOK! ** Welcome to Oakwood Manor, Sarasota’s only resident-owned 55+ community within the Sarasota city limits—where affordability meets an active, social lifestyle. This 2-bedroom, 1.5-bath home offers 749 sq. ft. of living space and sits on a desirable oversized lot (50 x 80.5), giving you extra room and exciting potential. A spacious covered and screened Florida room welcomes you at the front of the home—perfect for morning coffee, entertaining guests, or simply enjoying the Florida lifestyle year-round. Major Updates Already Done: ** A/C replaced in 2020 ** Roof replaced in 2023, new flooring through out 2026, new Kitchen, new baths and half bath and newly painted interior. Oakwood Manor spans 90 beautifully maintained acres and is known for its low maintenance fees and friendly, welcoming atmosphere. Community Amenities Include: ** Clubhouse with fitness room, dance floor & library ** Heated pool & hot tub ** Putt-putt golf, bocce ball, shuffleboard & cornhole ** Ping-pong & pool table ** Shaded seating areas & picnic park with grill ** Full calendar of social events and activities Love pickleball? Courts are just a short bike ride away along the Legacy Trail, located right next to the community. You’re also just minutes from downtown Sarasota, Gulf beaches, shopping, dining, and major hospitals—everything you need, right at your fingertips. Note: no pets, motorcycles or trucks community

3415 Spanish Oak Terrace, Sarasota
$515,000
4 Beds ⋅ 2 Baths ⋅ Bellevue Terrace SubDv. ⋅ 34237 Zip Code
Virtually Staged. Luxury, Location & Income Potential in the Heart of Sarasota Fully Renovated | X Flood Zone | No HOA | Public Water & Sewer | Turnkey Airbnb Income Introducing a rare opportunity in one of Sarasota’s most sought-after neighborhoods. This fully remodeled two-story, offering exceptional flexibility and income-generating potential, just minutes from Siesta Key Beach, Sarasota Memorial Hospital, and the University Town Center Mall. Located on a quiet street within an X flood zone (eliminating flood insurance requirements), with no HOA and public utilities, this property provides peace of mind and long-term value. Whether you're seeking a primary residence, a vacation retreat, or a proven short-term rental, this turnkey home is move-in ready and currently generating consistent rental income. Four spacious bedrooms and two fully updated bathrooms, an open, bright layout with large windows and elegant finishes, rich hardwood flooring, crown molding, stylish accents throughout, a gourmet kitchen with stainless steel appliances, sleek countertops, and ample cabinetry, Seamless flow between the kitchen, dining, and living areas—perfect for entertaining. Natural light and thoughtful design create an inviting ambiance, ideal for both everyday living and hosting guests. The expansive private backyard provides a serene space to relax, entertain, or add future amenities such as a pool or inlawsuite/tiny home etc. n. Fenced for privacy, it extends the living space outdoors. Prime Location - Enjoy close proximity to: Siesta Key Beach—world-renowned for its baby-powder-like sand - Sarasota Memorial Hospital - University Town Center Mall - Vibrant downtown Sarasota - I-75 access, top-rated schools, and waterfront dining. Live minutes from beaches, cultural attractions, shopping, and recreation—all within a tranquil, established neighborhood and all major systems updated, it stands out as a rare find in today’s market. Whether for personal use, as a seasonal residence, or to achieve rental success, this Sarasota home is poised to exceed expectations.

3052 Alta Vista St, Sarasota
$3,275,000
5 Beds ⋅ 5 Baths ⋅ La Linda Terrace SubDv. ⋅ 34237 Zip Code
Under Construction. A striking expression of modern luxury, this custom-built residence by Segatto Property Solutions Inc. is an exceptional new offering in Sarasota's highly sought-after Arlington Park. Scheduled for completion in 2026, this architecturally refined estate blends sophisticated design, uncompromising craftsmanship, and enduring quality in one of the city's most desirable locations. Designed for elevated living, the five-bedroom, four-and-a-half-bath residence with a private office welcomes you with dramatic 22-foot ceilings, expansive walls of glass, and an abundance of natural light that accentuates its clean architectural lines and curated designer finishes. The open-concept great room is anchored by a sleek contemporary LED fireplace and flows effortlessly into the dining area and gourmet kitchen, creating an elegant setting for both intimate gatherings and grand entertaining. The chef's kitchen is thoughtfully appointed with luxury SKS appliances, custom cabinetry, premium finishes, and an expansive island designed to be the heart of the home. Wide-plank luxury vinyl flooring, designer lighting with dimmable controls, and meticulous attention to detail elevate every space, creating a refined yet welcoming atmosphere. Built entirely of concrete block from foundation to roofline, this residence is engineered for lasting strength and peace of mind. Hurricane-impact windows and sliding glass doors, combined with a standing-seam metal roof, provide exceptional durability, energy efficiency, and resilience without compromising architectural beauty. The thoughtfully designed floor plan offers five spacious bedrooms, including luxurious private retreats, four-and-a-half beautifully appointed baths, and a dedicated office ideal for today's lifestyle. Every room has been carefully planned to maximize comfort, functionality, and privacy. Outdoor living is equally spectacular. Expansive covered lanais overlook the heated saltwater pool, creating a seamless extension of the home's living space. A fully equipped outdoor kitchen and bar invite effortless entertaining, while the maintenance-free turf backyard features a private putting green, generous fire pit gathering area, and beautifully designed spaces to relax and enjoy Sarasota's year-round sunshine. Completing the residence is an oversized three-car garage, LG Smart washer and dryer, premium designer fixtures, and thoughtfully integrated smart-home technology that enhances everyday living with modern convenience. Perfectly positioned in Arlington Park, residents enjoy immediate access to Sarasota Memorial Hospital, Southside Village, and downtown Sarasota's celebrated collection of fine dining, boutiques, galleries, and performing arts venues. Arlington Park's recreational amenities, the pristine beaches of Siesta Key, and Sarasota's picturesque waterfront are all just minutes away. Offering exceptional craftsmanship, luxurious amenities, and an unrivaled location, this is a rare opportunity to own a custom-built residence that embodies the very best of contemporary Sarasota living. Renderings are conceptual only and subject to change without notice during construction.

2122 Waldemere Street, Sarasota
$384,900
3 Beds ⋅ 2 Baths ⋅ Avon Heights SubDv. ⋅ 34237 Zip Code
Welcome to this 3-bedroom, 2-bathroom residence featuring a 2-car attached garage, an open floor plan and 9-foot ceilings that create a bright, spacious feel throughout. Step outside to enjoy the screened lanai overlooking the fully fenced backyard—perfect for relaxing or entertaining. Major updates provide peace of mind, including a new roof (2021), new A/C (2020), impact glass windows & sliding glass doors (2023), HVHZ impact front door (2021) new garage door (2022), fresh exterior paint 2025, a tankless natural gas water heater (2024), induction range (2024), dishwasher (2026) and washer & gas dryer (2024). Originally built in 1995 and ideally located within the City of Sarasota, this home offers exceptional convenience just minutes from downtown Sarasota, Sarasota Memorial Hospital, the YMCA, Arlington Park, and the Legacy Bike Trail. Best of all, there are no HOA or CDD fees, giving you added flexibility and lower ownership costs. This move-in-ready home combines quality updates, a prime location, and everyday comfort—don't miss this outstanding opportunity!

2354 Tami Sola Street, Sarasota
$155,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
You WILL LOVE Where You Live! Charming, cozy, and move-in ready in the highly desirable 55+ gated community of Oakwood Manor, the ONLY resident-owned park within Sarasota city limits—meaning NO LOT RENT! MAJOR IMPROVEMENTS provide peace of mind for years to come. Previous updates include vinyl siding, replacement windows, and the main sewer line (2018). Recent renovations include NEW LEVELING AND SUPPORT PIERS (10/2025), all NEW SUBFLOORING THROUGHOUT the home, including the Florida room (10/2025), fresh INTERIOR PAINT, LUXURY VINYL PLANK FLOORING THROUGHOUT the main living areas, and all NEW CARPET IN BOTH BEDROOMS (11/2025), a COMPLETE NEW TPO ROOFOVER (WITH A 20 YEAR TRANSFERABLE WARRANTY) AND NEW CARPORT with ADDITIONAL TIE-DOWNS RATED UP TO 150 MPH (2/2026), NEW HVAC system, ELECTRICAL PANEL NEW and METER BASE (3/2026), a NEW REAR CONCRETE PATIO (4/2026), and a NEWLY CONSTRUCTED FRAMED VINYL-SIDED SHED (6/2026).This delightful FULLY FURNISHED 2-bedroom, 2-bath bungalow-style home is proof that great things come in the perfect-sized package. Thoughtfully updated with quality improvements throughout, this home offers a desirable split-bedroom floor plan, abundant natural light, exceptional storage, and an inviting open-concept design. The added space of the living room push-out creates the perfect area for additional living or dining space, enhancing both comfort and functionality. The beautifully updated kitchen is designed for both functionality and style, featuring a built-in cooktop, built-in oven, overhead microwave, new refrigerator, garbage disposal, and ample cabinetry—making the most of every inch of space. The spacious front guest bedroom is highlighted by a large bay window that fills the room with natural light and is complimented by an en-suite bathroom and indoor laundry with stackable washer and dryer. A fully enclosed Florida room with newer windows and sliding glass doors provides approximately 120 square feet of additional living or entertaining space and features a convenient pass-through entrance to the front bedroom and guest bath, creating flexibility for guests, hobbies, or a relaxing sitting area. Oakwood Manor is a beautifully maintained, gated 90-acre community offering an exceptional Florida lifestyle with a low $210/month maintenance fee, which includes lawn care, cable TV, access to the heated pool and spa, clubhouse amenities, and more. Residents enjoy a spacious clubhouse with a fitness room, library, billiards, commercial kitchen, event hall, stage, dance floor, and an active social calendar filled with year-round activities, clubs, shuffleboard, putt-putt, and community events. Ideally located adjacent to the Legacy Trail and Sarasota's city-managed pickleball courts. Oakwood Manor is located nearby downtown Sarasota and the sandy shores of Lido Beach is an easy drive, with convenient access to shopping, dining, Tamiami Trail, and I-75. Please note that Oakwood Manor is an age-restricted community and does not permit pets or motorcycles.

3402 Shingle Oak Terrace, Sarasota
$145,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
OAKWOOD MANOR — WHERE FUN AND FRIENDSHIP HAPPEN TURNKEY, WELL MAINTAINED AND READY TO ENJOY-SARASOTA LIVING MADE EASY!!! Don’t miss this beautifully maintained 2-bedroom, 2-bath turnkey home offering 1,056 sq. ft. of comfortable living space in Oakwood Manor, a highly desirable resident-owned 55+ community located in the heart of Sarasota. Whether you’re searching for the perfect winter getaway or a full-time Florida residence, this move-in-ready home offers comfort, convenience, and exceptional value—all with an affordable $210/month HOA fee. Set within 90 beautifully maintained acres, Oakwood Manor is known for its friendly atmosphere, active lifestyle, and resort-style amenities. Residents enjoy a welcoming clubhouse with commercial kitchen and stage, fitness center, library, heated pool, hot tub, bocce ball, shuffleboard, and putt-putt golf. Pickleball lovers will appreciate being just a short bike ride from the Legacy Trail and its brand-new pickleball courts. (Please note: no pets, motorcycles, or RVs permitted.) Inside the home, pride of ownership is evident throughout. The bright and cheerful living room is filled with natural light from surrounding windows, creating a warm and inviting space to relax and unwind. The spacious kitchen offers abundant cabinetry and opens nicely to the dining area, making it ideal for both everyday living and entertaining. The home is being sold turnkey, so you can simply bring your suitcase and start enjoying the Florida lifestyle from day one. Both bathrooms have been tastefully updated, and the interior color palette perfectly complements the relaxed coastal feel of the home. This property has been lovingly maintained and truly needs nothing—just move right in and enjoy. Recent updates include: New flooring (2016) Fresh interior paint Roof coating (2025) New carport (2025) New blinds throughout New front awnings One of the standout features of this home is the private backyard with no neighbors behind, offering a peaceful setting to enjoy the outdoors. You’ll also love being just steps from the clubhouse, making it easy to take advantage of all the social events and community activities Oakwood Manor offers. Location is everything, and Oakwood Manor delivers. Conveniently located close to downtown Sarasota, Siesta Key Beach, St. Armand's Circle, shopping, dining, Sarasota-Bradenton International Airport, and local hospitals, this community combines an unbeatable Sarasota location with low-maintenance living and outstanding value. Homes in Oakwood Manor that are this clean, turnkey, and well-located don’t come along often—schedule your showing today and come see why so many love calling this community home.

3383 Oakwood Boulevard N, Sarasota
$289,000
3 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
OAKWOOD MANOR — WHERE FUN & FRIENDSHIP HAPPENS BIGGER, BETTER,AND READY TO ENJOY!!! Own your piece of paradise in Oakwood Manor, Sarasota's highly desirable resident-owned 55+ community located within the city limits. Spanning 90 beautifully landscaped acres, this vibrant community offers an exceptional resort-style lifestyle with remarkably low HOA fees of just $210 a month and no CDD or master association fees. Residents enjoy an impressive array of amenities including a welcoming clubhouse with commercial kitchen and event stage, fitness center, library, heated pool, oversized hot tub, bocce ball, shuffleboard, putt-putt golf, cornhole, and ping pong. Pickleball enthusiasts will appreciate the brand-new courts located just a short bike ride away along the Legacy Trail. With an active social calendar filled with events and activities, Oakwood Manor truly lives up to its reputation—where fun and friendship happen. A Rare Find — Impeccably Maintained & Truly Move-In Ready If you've been waiting for that special home, your search ends here. Built in 2005, this beautifully maintained 3-bedroom, 2-bath residence offers 1,545 square feet of thoughtfully designed living space and is being sold turnkey. Situated within easy walking distance of the community pool and amenities, this home is genuinely move-in ready—just bring your clothes and toothbrush. From the moment you step inside, you'll appreciate the spacious open floor plan, soaring ceilings, and abundant natural light streaming through numerous windows. The gourmet kitchen is designed to impress, featuring beautiful cabinetry, generous counter space, and an inviting layout that's perfect for everyday living and entertaining. The spacious primary suite includes a walk-in closet and an en-suite bath with a double vanity and walk-in shower. A standout feature rarely found in modular homes is the drywall construction throughout the walls and ceilings in most rooms, providing the look and feel of a traditional site-built home. Recent Updates Include: • New Roof (2025) • A/C replaced (2023) • All kitchen appliances replaced (2023) • Nice Large she for plenty of storage • Inside Laundry room with Utility laundry tub • Covered Carport with plenty of space for 2 cars • Tile flooring throughout all wet areas and the laundry room • Beautiful Bahama shutters on most windows Location, Location, Location Conveniently located just minutes from downtown Sarasota, Siesta Key Beach, St. Armand's Circle, SRQ Airport, shopping, dining, and two major hospitals, this home offers the perfect combination of comfort, convenience, and Florida lifestyle. Whether you're searching for a year-round residence or the perfect seasonal retreat, this exceptional home is an opportunity you won't want to miss.

3324 Overcup Oak Terrace, Sarasota
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