Mid Town Sarasota Homes with Pool Amenities

Mid Town Sarasota Homes with Pool Amenities

Welcome to Midtown Sarasota, a vibrant gem nestled in the heart of Florida's picturesque Sarasota County. Known for its charming neighborhoods and lush landscapes, Midtown Sarasota offers a unique blend of urban convenience and serene suburban living. With its prime location, residents enjoy easy access to the stunning Gulf Coast beaches, world-class dining, and a rich tapestry of cultural attractions, including art galleries, theaters, and the renowned Ringling Museum.

One of the standout features of homes in Midtown Sarasota is the abundance of properties boasting pool amenities. Imagine stepping into your own private oasis, where you can unwind after a long day or host lively gatherings with friends and family. These homes with pool amenities are designed for both relaxation and entertainment, providing the perfect backdrop for enjoying the balmy Florida weather. Picture yourself lounging poolside, sipping a refreshing drink, or enjoying a weekend barbecue in your backyard paradise.

Midtown Sarasota is more than just a place to live; it’s a community that embraces a laid-back lifestyle while offering a myriad of activities for all ages. Whether you're strolling through the local parks, exploring the farmers' market, or indulging in the eclectic dining scene, there’s always something new to discover.

If you’re looking for a home that combines comfort, style, and the luxury of a private pool, Midtown Sarasota is the perfect destination. Embrace the Florida lifestyle and make your dream home a reality in this enchanting city!

Newest Mid Town Sarasota Homes with Pool Amenities

1201 Tallywood Drive Unit 7001, Sarasota
$205,000
2 Beds ⋅ 2 Baths ⋅ Tallywood Condos SubDv. ⋅ 34237 Zip Code
Sarasota FL Villa – Your Florida Lifestyle for Just $205,000! Enjoy the best of Florida living in this inviting 2-bedroom, 2-bath villa in a 55+ community in Sarasota! Priced well, this is a wonderful opportunity to enjoy a relaxed lifestyle in a location close to everything that makes Sarasota special. Whether you're looking for a full-time residence, a seasonal Florida getaway, or a place to enjoy your retirement years, this villa offers an opportunity to make the Sunshine State your home without breaking the bank. Enjoy Sarasota's beautiful beaches, shopping, dining, golf, entertainment, and year-round sunshine, all within reach. Don't miss this opportunity to own your piece of Sarasota at an attractive price! If you've been waiting for the right time to make your move to Florida, this could be the one.

1201 Tallywood Drive Unit 7001, Sarasota
3218 Sumac Terrace, Sarasota
$164,800
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
Located in the ONLY Resident Owned Resort Style Park in the City limits of Sarasota!! This is a lovely 2 bed 2 bath turnkey furnished home offers 1,180sf of living space with the enclosed Florida room - all under the main AC. The updated floors ( and sub floors) have eye pleasing laminate and tile. 2024 windows (excluding baths) throughout and several structural updates show this home has been loved and cared for by a multi generational family for many years. THE SPACE: The KITCHEN provides ample cooking and storage cabinets, including a pantry. Appliances include a flat stove, range hood, dishwasher, fridge and microwave. The split plantation shutters in the LIVING room and dining room really dress up the space. Relax and watch your favorite shows on the large flat screen TV. The DINING room has a family size table with comfortable seating and the built in server/buffet hosting loads of invaluable storage and a long counter top that can serve as a food buffet style space when hosting friends and family. The PRIMARY BEDROOM is spacious with 3 closets and built in drawers! The en suite shower bath gives privacy from the main guest bath. The GUEST BEDROOM has 2 twin beds ( so plenty of room for a larger bed if desired ) a built in dresser and 2 closets. The outdoor storage (SHED) houses a washer dryer, the water heater, storage space and an overhead shelf. The FLORIDA ROOM can be enjoyed year round - refurbished in 2024 and faces North (no afternoon sun beating in the windows). With AC from the main home - this is a great multi use area where one can enjoy reading, a card/game area, office or den - in 2024 the Roof, windows, walls, flooring, entry door and sliding door were all updated. UPDATES/AGES: Main ROOF Over TPO 2019 with warranty, 2024 FLORIDA ROOM was rebuilt with new TPO Roof Over with warranty / Windows / Walls / Flooring / Exterior Door / Sliding glass door to living room. 2024 CARPORT was partially replaced and structurally updated to most recent hurricane codes, WINDOWS replaced 2024 (excluding baths), HVAC was replaced 2022 with warranty and serviced 10/2026, SKIRTING replaced 2024, 40 gal Rheem WATER HEATER was relocated to the shed. SEWER line replaced to the pea trap. Home was tented in 2018. **Please check with each vendor regarding their transfer requirements and continued warranty programs for buyer.** COMMUNITY FEATURES: The gated 90 acre community boasts a low maintenance fee with its vast amenities, starting with the spacious Clubhouse outfitted with a full commercial cook kitchen, event stage, audio/visual, dance floor, state of the art fitness room, activities hall, library with books/movies/puzzles and a pool table. Outside recreation includes an extra large heated pool with a handicap ramp, a spacious kidney shaped hot tub, ample umbrella tables and lounge chairs and updated shower rooms. Oak trees shade the beautiful park area, picnic tables and a community grill. Additional amenities to enjoy are the community putt putt course, bocce ball, ping pong and corn hole. Oakwood Manor is a vibrant community with numerous social events and activities. It is conveniently located adjacent to Legacy Trail and 12 newer pickle ball courts. Just a short drive to our crystal sand beaches, downtown area, the marina, fishing pier, local golf courses, shopping, variety of restaurants, the museum, SRQ airport, SMH and Doctors hospitals. Please note that Oakwood is a 55+, no pet, no motorcycle Park.

3218 Sumac Terrace, Sarasota
3329 Overcup Oak Terrace, Sarasota
$165,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Manor SubDv. ⋅ 34237 Zip Code
Enjoy the Sarasota lifestyle in this completely updated, fully furnished home in Oakwood Manor, a gated 55+ community with a low HOA fee of just $210 per month! Move-in ready, this inviting home features an open floor plan, newer windows and sliding glass door, and plenty of storage. Whether you’re seeking a seasonal getaway or a full-time Florida residence, you’ll feel right at home. Oakwood Manor offers an impressive array of amenities, starting with a spacious clubhouse featuring a full commercial kitchen, event stage, audio/visual equipment, dance floor, fitness room, activities hall, and a library stocked with books, movies, and puzzles, plus a pool table. Outside, enjoy the extra-large heated pool with an accessible ramp, a spacious kidney-shaped hot tub, umbrella tables, lounge chairs, and updated shower rooms. Beautiful oak trees shade the park and picnic area, complete with tables and a community grill. Stay active with miniature golf, bocce ball, ping-pong, and cornhole—or take advantage of the adjacent Legacy Trail and 12 newer pickleball courts. Conveniently located just a short drive from Sarasota’s white-sand beaches, downtown, the marina, fishing pier, local golf courses, shopping, restaurants, museums, SRQ Airport, Sarasota Memorial Hospital, and Doctors Hospital. Unpack, settle in, and start enjoying your Florida lifestyle! Please note: Oakwood is a 55+ community. Pets and motorcycles are not permitted.

3329 Overcup Oak Terrace, Sarasota
1209 Tallywood Drive Unit 7005, Sarasota
$249,000
2 Beds ⋅ 2 Baths ⋅ Tallywood SubDv. ⋅ 34237 Zip Code
Virtually Staged. Welcome to your beautifully renovated villa in Tallywood, a sought-after 55+ community! Move right in and enjoy the fresh, updated feel throughout this approximately 1,100-square-foot home. The brand-new kitchen features new appliances, including a microwave, and countertops creating a welcoming space for everyday meals and entertaining. Both bathrooms have been completely renovated with a clean, modern design, including new vanities while new carpeting in both bedrooms adds warmth and comfort. A brand-new washer and dryer add to the home's move-in-ready appeal. The enclosed lanai offers additional space to relax and unwind, while a covered carport and storage provide everyday convenience. Enjoy the Tallywood lifestyle with community amenities including a sparkling swimming pool, clubhouse, fitness center, and shuffleboard court. Ideally located just minutes from downtown Sarasota, the shopping and dining destinations at UTC, and the beautiful Gulf Coast beaches, this villa offers the perfect blend of comfort, convenience, and Florida living. Whether you're looking for a year-round residence or a seasonal retreat, this beautifully updated villa is ready to welcome you home!

1209 Tallywood Drive Unit 7005, Sarasota
500 N Jefferson Avenue Unit C3, Sarasota
$149,900
1 Beds ⋅ 1 Baths ⋅ Jefferson Club SubDv. ⋅ 34237 Zip Code
Discover your slice of Sarasota paradise in this charming villa at Jefferson Club! Ideally located just minutes from vibrant downtown Sarasota, beautiful Lido Beach, shopping, dining, and entertainment. Enjoy peace of mind with a **NEW ROOF and NEW AC (2025)!** This inviting retreat features thoughtful updates, including butcher block countertops, stainless steel appliances, soft-close cabinetry, and a newer front-loading washer and dryer. Enjoy your morning coffee or evening cocktails on your spacious, private gated patio, perfect for relaxing or entertaining. Whether you're looking for a full-time residence, seasonal getaway, or investment opportunity, this villa offers the perfect blend of comfort, convenience, and Florida living. Don't miss your chance to make it yours!

500 N Jefferson Avenue Unit C3, Sarasota
936 La Costa Circle Unit 10, Sarasota
$217,900
1 Beds ⋅ 1 Baths ⋅ Park View SubDv. ⋅ 34237 Zip Code
Step inside this luxuriously updated, move-in-ready condo in Park View, one of Sarasota’s best-kept secrets! Tucked away in a gated community just minutes from vibrant downtown Sarasota and the beautiful Gulf Coast beaches, Park View offers a peaceful retreat in an unbeatable location. This hidden gem is centered around a beautifully maintained park, creating a serene setting with lush green space right outside your door. Residents enjoy two community pools, a clubhouse, and a fitness center, while monthly fees conveniently include water, sewer, trash, and cable. From the moment you enter this stunning residence, you'll feel a sense of warmth, comfort, and sophistication. Thoughtfully redesigned with earthy modern finishes, stylish architectural details and luxurious upgrades, this exceptional home seamlessly blends timeless style with contemporary comfort, creating a space that feels as inviting as it is impressive. Enjoy added peace of mind with updated hurricane-impact windows. Best of all, this spectacular condo is being offered fully furnished, making your transition effortless. Simply bring your suitcase and start enjoying the Sarasota lifestyle! Whether you're searching for a full-time residence, a seasonal escape, or your own slice of Florida paradise, this extraordinary condo checks every box. A rare opportunity to own a retreat in one of Sarasota's most charming hidden communities. Come experience it for yourself—you won't want to leave!

936 La Costa Circle Unit 10, 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. Plus this home is on a corner lot with tons of space rarely available in Oakwood Manor. 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
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
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
3415 Spanish Oak Terrace, 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
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