Mid Town Sarasota Homes with Deed Restrictions Community Features

Mid Town Sarasota Homes with Deed Restrictions Community Features

Welcome to Midtown Sarasota, a hidden gem nestled in the heart of Florida's picturesque Sarasota County. This vibrant community is a delightful blend of urban convenience and suburban tranquility, making it an ideal destination for families, retirees, and anyone looking to embrace the sunny Florida lifestyle.

Midtown Sarasota is renowned for its charming neighborhoods, where homes with deed restrictions ensure a cohesive aesthetic and enhance property values. These deed-restricted communities often feature beautifully landscaped lawns, well-maintained common areas, and a sense of pride among residents. Here, you’ll find a variety of architectural styles, from modern masterpieces to classic Florida ranch homes, each reflecting the unique character of the area.

Residents of Midtown Sarasota enjoy a wealth of amenities right at their fingertips. With proximity to top-rated schools, shopping centers, and local eateries, everything you need is just a short drive away. The community is also close to stunning beaches, lush parks, and cultural attractions, including art galleries and theaters, ensuring there’s always something to explore.

Moreover, Midtown Sarasota boasts a friendly atmosphere, where neighbors become friends and community events foster a strong sense of belonging. Whether you’re taking a leisurely stroll through the neighborhood or participating in local festivities, you’ll quickly discover the warmth and camaraderie that define this charming community.

In Midtown Sarasota, you’re not just purchasing a home; you’re investing in a lifestyle that celebrates both comfort and community. Come and experience the allure of this enchanting area, where your dream home awaits!

Newest Mid Town Sarasota Homes with Deed Restrictions Community Features

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
3208 Ramblewood Drive N, Sarasota
$185,000
3 Beds ⋅ 3 Baths ⋅ Ramblewood Acres SubDv. ⋅ 34237 Zip Code
Welcome to 3208 Ramblewood Drive in Ramblewood Acres, an inviting gated community in the heart of Sarasota. This beautifully updated 3-bedroom, 2½-bath condominium offers exceptional comfort and convenience, complete with a private carport, an adjacent laundry room, and plenty of storage throughout. Enjoy three charming porches—two upstairs and one downstairs—including one overlooking the peaceful creek with a peek-a-boo view of the tennis courts. Inside, the home features tasteful updates throughout. New flooring throughout the first floor, updated bathrooms, and fresh paint and molding, creating a bright and welcoming atmosphere. Have peace of mind with a NEW ROOF (2025), NEWER HVAC (2023), NEWER WATER HEATER (2023), NEW DISHWASHER (2024), NEW DRYER (2024) and much more. Step outside and take advantage of the community’s impressive amenities: three swimming pools (with one just a short walk away), tennis courts, a fitness center, billiard room, playground, and a community center. The multi-acre property also affords for those morning or afternoon peaceful walks. Perfectly located near Sarasota’s top dining, shopping, and cultural attractions—and just a few miles from the world-famous white sands of Siesta Key Beach—this residence combines privacy, comfort, and an exceptional lifestyle in one of the area’s most desirable locations. Be sure to tell all family and friends, “I live where you vacation.”

3208 Ramblewood Drive N, 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
500 N Jefferson Avenue Unit A1, Sarasota
$159,000
2 Beds ⋅ 1 Baths ⋅ Jefferson Club SubDv. ⋅ 34237 Zip Code
Charming Sarasota Condo | 2 Bedrooms | 1 Bathroom. Welcome to Jefferson Club in Sarasota, Florida! This inviting 2-bedroom, 1-bathroom condo offers a wonderful opportunity to enjoy the Sarasota lifestyle, whether you're searching for a place to call home, a seasonal retreat, or an investment opportunity. The open living area creates a comfortable space to relax and entertain, while the functional layout offers flexibility for everyday living. The kitchen features classic cabinetry and a warm, welcoming feel, flowing into the main living space. Major updates provide added peace of mind! The condo has been recently re-piped, features a new water heater, and has a newer AC system. The roof was also recently replaced. Just minutes to Downtown, you don't want to miss this unit! Conveniently located in Sarasota, you'll have the opportunity to enjoy the area's shopping, dining, entertainment, and beautiful Gulf Coast attractions.

500 N Jefferson Avenue Unit A1, 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
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
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 (New Washer 2024) 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. 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
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
642 N Jefferson Avenue Unit 13, Sarasota
$199,900
2 Beds ⋅ 2 Baths ⋅ Bermuda Park SubDv. ⋅ 34237 Zip Code
Virtually Staged. Welcome to 642 N Jefferson Ave, a 2-bedroom, 2-bath condo in Bermuda Park offering a spacious layout, vaulted ceilings, a private screened lanai, and no rear neighbors—all just minutes from Downtown Sarasota. Located in one of the newer buildings in the community, this condo features an open-concept living area with abundant natural light and two new PGT windows. The kitchen includes stainless steel appliances, ample cabinet space, and a breakfast bar that opens to the main living area. In-unit laundry, two reserved parking spaces, and additional guest parking add everyday convenience. The screened lanai overlooks peaceful greenspace with no buildings directly behind the unit, providing added privacy in a central Sarasota location. Enjoy quick access to Downtown Sarasota, shopping, dining, St. Armands Circle, Lido Beach, and Sarasota’s arts and entertainment. The free Breeze Trolley provides another convenient way to explore the area.

642 N Jefferson Avenue Unit 13, 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
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