Mid Town Sarasota Homes with Pool Community Features

Mid Town Sarasota Homes with Pool Community Features

Welcome to Midtown Sarasota, where vibrant city life meets the serene beauty of Florida’s Gulf Coast. Nestled in the heart of Sarasota County, this charming neighborhood is a hidden gem that offers a perfect blend of urban convenience and suburban tranquility. With its lush landscapes, palm-lined streets, and proximity to stunning beaches, Midtown Sarasota is an ideal place for families, retirees, and everyone in between.

One of the standout features of this community is its inviting homes with pools. Imagine stepping into your backyard oasis, where you can unwind in your private pool after a long day or host unforgettable gatherings with friends and family. These homes are designed with outdoor living in mind, making the most of Florida's sunny climate. Whether you prefer a quaint bungalow or a spacious modern home, you’ll find a variety of options that cater to your lifestyle.

Midtown Sarasota is not just about beautiful homes; it’s also a community that thrives on connectivity and convenience. Residents enjoy easy access to local parks, shopping centers, and a plethora of dining options that showcase the rich culinary scene of the area. The vibrant arts culture, highlighted by the nearby Ringling Museum and the Sarasota Opera, provides endless opportunities for entertainment and enrichment.

With its warm climate, friendly atmosphere, and stunning properties featuring pools, Midtown Sarasota is more than just a place to live—it's a lifestyle. Come and discover the charm of this wonderful community, where your dream home awaits!

Newest Mid Town Sarasota Homes with Pool Community Features

3412 Oakwood Boulevard S, Sarasota
$189,500
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
WELCOME HOME... Just move in... Fully Furnished spacious 2 bedroom 2 bath doublewide home in Highly desirable Resident Owned OAKWOOD MANOR located in the Heart of Sarasota. Fully Remodeled Kitchen with abundant of cabinet space and Granite counter tops, Both bath have new solid wood vanities and and solid surface counter tops ($18,450), New central air system ($7700), and Roof just resealed($5,500), updated electric. This 1266 sqft offers both a generous Family room and living room and large dining area with cabinetry for storage. Oversized master suite with plenty of room for storage. Enclosed Florida room leads to inside Laundry and tool shed. Attached Carport, Oakwood Manor is an affordable getaway for winter snow birds or full time residents. Located within 90 acres with low HOA dues of $210 a month which covers cable tv, lawn maintenance and resort style amenities. Community activities include resort style heated pool, hot tub, bocce ball, shuffleboard courts, putt-putt golf, clubhouse, fitness center, open park area with Gazebo. Property backs up to legacy trail and New Pickle Ball courts. Conveniently located within the city limits of Sarasota with easy access to downtown, Siesta Key, St. Armands Circle, Shopping, Dining, access to I-75 and Sarasota-Bradenton Airport. Welcome to were the fun begins.

3412 Oakwood Boulevard S, Sarasota
3308 Over Cup Oak Terrace, Sarasota
$174,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
WELCOME TO YOUR FLORIDA LIFESTYLE AT OAKWOOD MANOR! AFFORDABLE SARASOTA PARADISE IN A RESIDENT-OWNED 55+ COMMUNITY Live where every day feels like a vacation! Welcome to Oakwood Manor, one of Sarasota’s sought-after resident-owned 55+ communities. Set across 90 beautifully landscaped acres within Sarasota city limits, Oakwood Manor offers an appealing blend of affordability, comfort, and resort-style living for just $210/month HOA, with no CDD or master association fees. This well-maintained 2-bedroom, 2-bath home offers 1,152 square feet of inviting living space and is being sold turnkey, excluding personal items. Just bring your suitcase and start enjoying the Florida sunshine! Pride of ownership shines throughout this inviting home. The bright, enclosed sunroom, surrounded by windows and filled with natural light, is the perfect spot for morning coffee, afternoon relaxation, or entertaining friends. The spacious kitchen offers abundant cabinetry, a pantry, and a convenient center island, along with a ceramic cooktop range, microwave, dishwasher, and refrigerator. The kitchen flows easily into the dining area, creating a comfortable setting for everyday living and entertaining. The secondary bedroom features direct access to the guest bathroom, offering added privacy and a layout that functions almost like a second primary suite. HOME FEATURES & IMPROVEMENTS 2 bedrooms, 2 bathrooms, and 1,152 square feet of living space Bright, enclosed sunroom filled with natural light Spacious kitchen with center island, pantry, and abundant cabinetry Ceramic cooktop range, microwave, dishwasher, and refrigerator A/C replaced in 2022 Carport roof replaced in 2025 to meet the latest building code, as reported PVC plumbing from the home to the street replaced in 2021 Roof replacement history includes 2017 and 2019 Large storage shed Washer and dryer included RESORT-STYLE AMENITIES & AN ACTIVE LIFESTYLE Enjoy a wonderful selection of community amenities, activities, and opportunities to connect with neighbors: Heated swimming pool and oversized hot tub Clubhouse with commercial kitchen and event stage Fitness center and library Bocce ball and shuffleboard courts Putt-putt golf Active social calendar and welcoming neighbors Love pickleball? The Legacy Trail and its pickleball courts are just a short bike ride away! AN IDEAL SARASOTA LOCATION Conveniently located just minutes from downtown Sarasota, beautiful Siesta Key Beach, the shopping and dining of St. Armands Circle, Sarasota-Bradenton International Airport, and nearby hospitals and medical facilities. Even better, this home is just steps from the clubhouse, putting community activities and amenities within easy reach. Whether you're searching for a seasonal Florida retreat or a year-round residence, this inviting home offers an opportunity to enjoy the Sarasota lifestyle without the price tag of a traditional resort community. COME DISCOVER THE VALUE, THE LIFESTYLE, AND THE FRIENDLY COMMUNITY THAT MAKE OAKWOOD MANOR A SARASOTA HIDDEN GEM!

3308 Over Cup Oak Terrace, Sarasota
3309 Oakwood Boulevard S, Sarasota
$169,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
Welcome to Your Florida Lifestyle at Oakwood Manor! Affordable Sarasota Living in a Resident-Owned 55+ Community Your slice of Sarasota paradise is waiting! Discover the perfect blend of affordability, comfort, and resort-style living at Oakwood Manor, one of Sarasota’s cherished resident-owned 55+ communities. Set across 90 beautifully landscaped acres within Sarasota city limits, this welcoming community offers an active lifestyle and a wonderful place to call home. Enjoy all this for just $210 a month in HOA fees, with no CDD or master association fees! Move-In Ready and Full of Charm This well-maintained 1977 home features 2 bedrooms, 2 bathrooms, and 1,056 square feet of inviting living space. Offered turnkey, excluding personal items, this home is ready for you to move in, unpack, and start enjoying the Florida sunshine! From the moment you arrive, you’ll appreciate the care and pride of ownership throughout. The bright, enclosed sunroom, surrounded by windows and filled with natural light, is the perfect place to sip your morning coffee, curl up with a good book, or entertain friends. Inside, the spacious kitchen offers abundant cabinetry and flows seamlessly into the dining area, creating a comfortable setting for everyday living and entertaining. Generous closet space throughout the home provides valuable storage, while the convenient indoor laundry area adds to the home’s functionality. Home Features & Recent Upgrades 2-bedroom, 2-bathroom floor plan Bright, window-filled enclosed sunroom Spacious kitchen with abundant cabinetry Cooktop, wall oven, dishwasher, and refrigerator included Roof replaced in 2023 A/C replaced in 2022 Laminate flooring throughout Updated outdoor electrical service in 2025 PVC plumbing from the home to the street replaced in 2023 Indoor laundry area with washer and dryer Carport roof reinforced to meet the latest code requirements Resort-Style Amenities and an Active Lifestyle At Oakwood Manor, there’s always something to enjoy! Whether you love staying active, socializing with neighbors, or simply relaxing in the Florida sunshine, this community offers something for everyone. Heated swimming pool and oversized hot tub Clubhouse with commercial kitchen and event stage Fitness center Community library Bocce ball and shuffleboard courts Putt-putt golf Active social calendar and welcoming neighbors Love pickleball? You’re just a short bike ride from the Legacy Trail and its new pickleball courts, making it easy to enjoy outdoor recreation and stay active. An Incredible Sarasota Location Enjoy the best of Sarasota living with beaches, shopping, dining, entertainment, and everyday conveniences just minutes away. Downtown Sarasota World-famous Siesta Key Beach St. Armands Circle’s shopping and dining Sarasota-Bradenton International Airport Nearby hospitals and medical facilities Even better, this home is ideally located just steps from the clubhouse, putting community activities, social events, and amenities conveniently close to home. Your Florida Dream Starts Here! Whether you’re searching for a seasonal retreat, a sunny retirement getaway, or a comfortable year-round residence, this home offers an inviting opportunity to enjoy the Sarasota lifestyle without the price tag of many resort-style communities. Please note: Community restrictions prohibit pets, motorcycles, and RVs.

3309 Oakwood Boulevard S, Sarasota
2744 Hidden Lake Boulevard Unit C, Sarasota
$135,000
2 Beds ⋅ 1 Baths ⋅ Hidden Lake Village SubDv. ⋅ 34237 Zip Code
Welcome to an exceptional Sarasota opportunity at 2744 Hidden Lake Blvd #C! Beautifully remodeled and thoughtfully updated, this impeccably maintained residence blends modern style, comfort, and effortless Florida living. From the moment you step inside, you’ll appreciate the care and attention to detail that went into creating a home that feels fresh, inviting, and truly move-in ready. Ideally situated in one of Sarasota’s desirable areas, this home places you just minutes from the excitement of downtown Sarasota, with its renowned restaurants, boutique shopping, arts, culture, and vibrant entertainment. And when it’s time to unwind, the world famous sands of Siesta Key and Sarasota’s beautiful Gulf Coast beaches are only a short drive away. Meticulously cared for and tastefully designed, this residence offers the perfect combination of location, lifestyle, and value. Whether you’re searching for a primary residence, a Florida getaway, or an investment opportunity, this is your chance to enjoy everything Sarasota has to offer at an incredible price. Opportunities like this don’t come along every day. Come experience the charm, updates, and unbeatable location for yourself, this one is sure to impress!

2744 Hidden Lake Boulevard Unit C, Sarasota
727 N Jefferson Avenue Unit 727, Sarasota
$234,900
2 Beds ⋅ 2 Baths ⋅ Jefferson Pines SubDv. ⋅ 34237 Zip Code
Priced to Sell. Welcome to your newly renovated two bedroom two bath villa/condo in the community of Jefferson Pines. Close proximity to downtown Sarasota to experience all the restaurants, shopping and waterfront the city has. This unit has been completely remodeled from top to bottom to include vinyl flooring and 6 inch baseboard throughout, recessed lighting throughout, new air conditioning unit in 2024, new hot water heater in 2024, new bathrooms, vanities, showers, and tub, as well as a completely remodeled kitchen with solid wood cabinets, and all new stainless appliances and of course fresh paint throughout the unit. Also, a completely new lanai enclosure as well as new concrete slab. The community itself has matured landscaping, a community pool and is a very quiet, peaceful neighborhood. The unit also includes two numbered/assigned parking spots directly in front of the unit for your convenience. If you’re looking for all the conveniences of Sarasota and a move-in ready Villa come take a look. Motivated Seller, Let's talk today!

727 N Jefferson Avenue Unit 727, Sarasota
3390 Ramblewood Court, Sarasota
$159,900
2 Beds ⋅ 3 Baths ⋅ Ramblewood Acres SubDv. ⋅ 34237 Zip Code
Virtually Staged. END-UNIT TOWNHOME WITH PRIVATE OUTDOOR SPACE IN GATED RAMBLEWOOD ACRES! Welcome to 3390 Ramblewood Court, offering 1,343 square feet of comfortable living space in a convenient Sarasota location. The main level features a spacious living and dining area, kitchen, convenient half bath, and a screened lanai for additional outdoor living. Upstairs, the bedrooms offer privacy and generous space, complemented by private outdoor areas including a spacious deck—perfect for relaxing and enjoying the Florida weather. Covered parking is another welcome benefit. Ramblewood Acres offers an impressive collection of amenities, including three swimming pools, tennis courts, a playground, and a spacious clubhouse with a fitness center, billiards room, library, and gathering spaces for social events. The gated community is conveniently located just minutes from Downtown Sarasota, shopping and dining, the Baltimore Orioles spring training stadium, Sarasota-Bradenton International Airport, UTC, and Sarasota’s world-renowned Gulf beaches. A wonderful opportunity to enjoy the Sarasota lifestyle with plenty of space, outdoor living, and community amenities close to everything.

3390 Ramblewood Court, Sarasota
1236 Tallywood Drive Unit 7029, Sarasota
$149,900
2 Beds ⋅ 2 Baths ⋅ Tallywood Condos SubDv. ⋅ 34237 Zip Code
TALLYWOOD 55+ COMMUNITY – VILLA-STYLE HOME! Welcome to this 2-bedroom, 2-bath villa-style home located in the Tallywood community in beautiful Sarasota, Florida. Offering a comfortable layout and the opportunity to make it your own, this property is ready for its next owner to bring their vision and personal touches. Enjoy the convenience of villa-style living in an established 55+ community, with a location close to shopping, restaurants, and everyday conveniences. Whether you’re looking for a seasonal retreat, full-time residence, or renovation opportunity, this property offers plenty of possibilities. Property is being sold as-is. Buyer to conduct their own due diligence regarding the property’s condition, community amenities, fees, and any applicable restrictions.

1236 Tallywood Drive Unit 7029, Sarasota
2121 Wood Street Unit 113, Sarasota
$244,900
2 Beds ⋅ 2 Baths ⋅ Citywalk SubDv. ⋅ 34237 Zip Code
Completely renovated and truly move-in ready, this ground-floor 2-bedroom, 2-bath condo in gated Citywalk puts you steps from Publix, Payne Park, the Legacy trail and everything downtown Sarasota has to offer. The work here is done. The kitchen was completely renovated less than three years ago with quartz countertops, new cabinetry, new appliances, and a reverse-osmosis drinking water system. Every appliance is under three years old, including a stackable washer and dryer added within the past year. The HVAC and ROOF are both about two years old, the electrical and plumbing have been updated, and the interior was freshly painted just four months ago. There is NO CARPET anywhere in this unit. This condo also has new hurricane impact windows and sliders for peace of mind. A light-filled living area opens through sliding glass doors to a private screened lanai with a garden view. The generous ensuite bedroom features a sliding barn door and a private bath, with a second bedroom and full bath for guests. Single-story living with no stairs, assigned parking, and solid block construction. The monthly fee covers water, exterior maintenance, grounds, fitness center and the community pool. No flood insurance required. The location is the rest of the story: walk to Payne Park for tennis, trails, and the playground, hop on the Legacy Trail, and reach Main Street's restaurants and theatre district in minutes. Downtown Sarasota and the world-renowned Gulf beaches are just a short drive away.

2121 Wood Street Unit 113, Sarasota
2400 Ezzell Court, Sarasota
$729,000
3 Beds ⋅ 3 Baths ⋅ Payne Park Sub SubDv. ⋅ 34237 Zip Code
Location, floorplan and quality of life: Payne Park Village is between the Legacy Trail, a 29-acre park with a playground, walking trail and tennis club--and two blocks from Main Street in downtown Sarasota. This townhouse community is only a few years old; original owner. This corner unit provides plenty of natural light--and large rooms with high ceilings. Each floor of this 3-bedroom townhouse has an ensuite bedroom. This split floor plan is ideal for privacy or for couples working from home. The gourmet kitchen is equipped with modern stainless steel appliances, granite countertops, and tall 'soft close' cabinets and drawers. There is a charming front courtyard for entertaining or relaxing outside. Residents can enjoy outdoor living spaces, including a heated lap-pool, hot tub, lawn and dog park. The property includes a two-car garage, providing secure and convenient parking options. There is also guest parking nearby. Payne Park Village is a sought-after neighborhood known for its proximity to downtown Sarasota, offering easy access to cultural venues, events, dining, shopping, and entertainment options.

2400 Ezzell Court, Sarasota
3191 Glen Elyn Boulevard Unit 4, Sarasota
$289,000
2 Beds ⋅ 2 Baths ⋅ Glen Elyn SubDv. ⋅ 34237 Zip Code
This spacious 2-bedroom, 2-bath villa with an ATTACHED TWO-CAR GARAGE on corner lot, offers an exceptional opportunity for easy, maintenance-free Sarasota living. Located in Glen Elyn, an intimate and well-maintained community of just 24 attached villas, this move-in-ready home can be sold Furnished. The remodeled Kitchen features granite countertops, a beautiful marble backsplash, under-cabinet lighting, pull-out cabinet shelving, pantry closet and reverse-osmosis/water filtration system. Both bathrooms have been remodeled with granite countertops, marble flooring and pull-out cabinet shelving. Both bathrooms are equipped with washlet/bidet toilets featuring HEATED SEATS. The inviting living area features recessed lighting and sliding glass doors that open to the lanai, creating a wonderful extension of the living space for morning coffee, entertaining friends or simply relaxing and enjoying the Florida lifestyle. Additional upgrades include a 2022 A/C system, WiFi-enabled thermostat with remote control and automatic cell phone alerts, Hurricane Shutters, abundant storage and a utility sink conveniently located in the two-car garage near the washer and dryer. Glen Elyn offers the carefree lifestyle Florida buyers are looking for. Relax at the COMMUNITY POOL overlooking the peaceful waterway and enjoy the breeze without the maintenance of a private pool. Even better, the monthly fee covers nearly everything except electricity and phone, adding to the ease and convenience of ownership. LOCATION, LOCATION, LOCATION! Approximately ONE MILE FROM ED SMITH STADIUM, spring training home of the Baltimore Orioles, and convenient to Downtown Sarasota, UTC, shopping, dining, entertainment, cultural attractions and Sarasota's renowned Gulf Coast beaches. Updated and priced to sell, this villa offers a hard-to-find combination of space, a two-car garage, extensive upgrades, full hurricane protection and a maintenance-free Sarasota lifestyle. Great year round or Seasonal home and no leasing here – 100% owners. Schedule your showing and make it yours!

3191 Glen Elyn Boulevard Unit 4, Sarasota
3189 Glen Elyn Boulevard Unit 3, Sarasota
$199,999
2 Beds ⋅ 2 Baths ⋅ Glen Elyn SubDv. ⋅ 34237 Zip Code
Virtually Staged. Welcome to Glen Elyn, a unique and intimate community of just 24 villas, conveniently located less than 3 miles from vibrant Downtown Sarasota! This charming 2-bedroom, 2-bath villa with an attached 1-car garage offers 1,030 square feet of thoughtfully designed living space—comfortable, efficient and easy to maintain whether you’re looking for a full-time residence or the perfect Florida winter retreat. A welcoming foyer leads into the dining area and spacious living room, creating an easy, natural flow for everyday living and entertaining. Sliding glass doors open to the enclosed lanai, extending your living space and providing a comfortable spot for morning coffee, reading or relaxing. The kitchen offers ample cabinet storage along with a recessed ceiling featuring excellent lighting and additional under-cabinet lighting to brighten your workspace. The spacious owner’s suite features a large walk-in closet, separate makeup/vanity area and private bath with a commode and tub/shower combination with glass doors. The generously sized front guest bedroom is conveniently located near the second full bath, featuring a shower with sliding glass doors and multiple shower heads. Enjoy additional peace of mind with roofs replaced in May 2024, BRAND NEW HVAC-SEPT 2026! and a recently replaced ELECTRICAL PANEL. Glen Elyns' $584 monthly association fee includes basic cable, water, sewer and trash, along with maintenance of the private road and roofs. Residents also enjoy a community swimming pool and a modest community gathering room used for association meetings, complete with a small resident sharing library—a simple and welcoming touch that reflects the close-knit nature of this community. Blacktopped drives, ample guest parking and simple yet pristine landscaping add to the appeal of this tucked-away community. Glen Elyn is also 100% owner occupied with NO RENTALS permitted, helping maintain the residential character and pride of ownership found throughout the neighborhood. And the location is hard to beat! You’re less than 3 miles from Downtown Sarasota, with its restaurants, shopping, arts and entertainment, while still enjoying the quiet setting of a small residential community. Whether you’re looking for a full-time Sarasota home, an easy lock-and-leave winter retreat, or a mainland getaway from one of the barrier islands, Glen Elyn offers comfortable Florida living in a special community of only 24 residences.

3189 Glen Elyn Boulevard Unit 3, Sarasota
1554 Tallywood Drive Unit 7127, Sarasota
$229,900
3 Beds ⋅ 2 Baths ⋅ Tallywood Condos SubDv. ⋅ 34237 Zip Code
Excellent VALUE with all the upgrades in this unit. UPDATED kitchen with Shaker, soft-close cabinets, quartz countertop, stainless appliances. Updated bathroom vanities and showers. High-impact windows. Screened-in Lanai. Private backyard. Carport with a storage area. Exterior and interior painting 2026. Roof and exterior maintained by the Association. If you have pets, 1 dog and 2 indoor cats allowed. Meet your neighbors at the Community Pool and Clubhouse. This 55+ Sarasota community embraces 46 acres with Spanish Moss-covered trees in a park-like setting. LOCATED a short distance to downtown Sarasota, University Town Center (UTC), great restaurants and shopping, sandy Lido Beach and Siesta Beach, various theatres, SRQ Airport and other Sarasota cultural and sports amenities. Schedule your showing today to buy now at a GREAT PRICE, and you, too, can experience a low-maintenance Florida LIFESTYLE! NOW is a great time to BUY, and this unit is a great buy!

1554 Tallywood Drive Unit 7127, Sarasota
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