Location: Englewood, Englewood
Do Not Show Listings
4 CURACAO CIR #40, ENGLEWOOD, FL 34223
$315,00015 Days on yellowkey MLS ID: D6146958
REDUCED by $10,000 (3.1%) on 04/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1463 Built: 1974Monthly Fee: $475 Tax: $3,556 (2025)Community: Boca Royale / Englewood Golf Villas 06Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,556
Elementary School: Englewood Elementary
High School: Lemon Bay High
Tax Year: 2025
Middle School: L.A. Ainger Middle
Remarks: Welcome to Boca Royale Villas, where charm meets easy Florida living. Nestled within lush tropical surroundings, this delightful freestanding cottage offers a warm and inviting retreat. Inside, you’ll find two spacious bedrooms, each featuring walk-in closets and private ensuite bathrooms. Stylish laminate and tile flooring run throughout the home, some furniture may be negotiable. The expansive 23' x 16' Great Room and 13' x 10' Dining Room are filled with natural light, thanks to sliding glass doors that open to a covered, screened lanai—perfect for relaxing while enjoying the vibrant landscaping. The galley-style kitchen is both functional and updated, featuring new appliances including an oven, dishwasher, and refrigerator, along with tile floors and two closet pantries. A new roof installed in November 2022 adds peace of mind. Residents of the Golf Villas enjoy access to a community pool that’s both heated and chilled for year-round comfort. Exterior maintenance is taken care of, including lawn care, landscaping, painting, roof cleaning, and pest control. Basic cable is also included. Enjoy an active lifestyle with community social events, or take a quick 4.1-mile drive to the beach for sun and sand. Don’t miss this opportunity—schedule your showing today and discover your next home!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-473-8484)
Listing Agent: Karin Dubbs (941-416-4637)
1725 OVERBROOK RD, ENGLEWOOD, FL 34223
$980,00040 Days on yellowkey MLS ID: N6143364
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2887 Built: 2015 Tax: $7,702 (2025)Community: Englewood GardensSingle Family
Taxes:$7,702
Elementary School: None
High School: None
Middle School: None
Remarks: Private. Custom. Energy-Efficient. Low-Maintenance. Built with Strength. This one-of-a-kind residence blends solid concrete construction (including the roof) with open, light-filled living. Set on 1.3 acres just minutes from Manasota Beach, with the Intracoastal Waterway across the street, the property offers a rare mix of seclusion, durability, and coastal convenience. The 3-bedroom, 3-bath home spans 2,887 sq ft and showcases polished concrete floors, high ceilings, exposed ductwork, clean architectural lines, and oversized windows that frame the surrounding natural landscape. The open-concept kitchen features a 100+ year-old maple island, modern cabinetry, and stainless steel appliances, flowing seamlessly into expansive living and dining areas ideal for entertaining or everyday living. Sliding glass doors open to a wide outdoor patio, extending the living space into the serene setting. Thoughtfully designed native Florida landscaping complements the green roof and concrete design, supporting natural cooling, efficient drainage, and low-maintenance living. Designed with a resort-style pool in mind beyond the patio, the property presents a rare opportunity to craft a truly private outdoor retreat. Enjoy the convenience of a short bike or golf-cart ride over the bridge to Manasota Beach, with the option to join the Englewood Gardens Beach Club, offering private beach access, dedicated parking, and a calendar of social events. This exceptional home is a must-see to truly appreciate.
Listing is courtesy of: COLDWELL BANKER REALTY (941-493-1000)
Listing Agent: Jessica Warmack (248-535-5150)
1819 CHADWICK RD, ENGLEWOOD, FL 34223
$3,850,000162 Days on yellowkey MLS ID: A4671558
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3967 Built: 1999 Tax: $17,146 (2024)Community: Englewood GardensSpa: YesSingle Family
Taxes:$17,146
Tax Year: 2024
Remarks: A rare opportunity to own one of Lemon Bay’s most exceptional private waterfront estates. Set on more than an acre along the bay’s widest expanse, this fully reimagined coastal retreat delivers extraordinary privacy, breathtaking sunsets, and resort-style living in the heart of Englewood. Completed after an extensive two-year renovation, the elevated main residence blends timeless architecture with impeccable finishes and modern resilience. The 2-bedroom, 2.5-bath home features expansive water views, open-concept living spaces, and a stunning chef’s kitchen appointed with custom rift-sawn white oak cabinetry, Cambria surfaces, Wolf and Sub-Zero appliances, dual dishwashers, and a generous Galley workstation sink. A dramatic wall of sliding glass opens to an extraordinary outdoor setting with a saltwater pool and spa, covered summer kitchen, fire features, and multiple spaces designed for entertaining or quiet relaxation. The completely remodeled 3- bedroom, 2 bath private guest house creates an ideal compound for family, extended stays, or distinguished visitors, offering seasonal sunset views, 2 full kitchens and laundry and living areas with their own saltwater pool and infinity spa. Built for comfort and peace of mind, the estate includes hurricane-impact glass, new electric and plumbing, 13ft elevation, whole house generators for both main house and guest house, metal roofing and spray foam insulation, and premium construction enhancements - too many to mention here. This property is as storm proof as it is charming and elegant. Must be seen to be fully appreciated.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Bill Cantrell (941-586-8301)
17 N CAYMAN ISLES BLVD, ENGLEWOOD, FL 34223
$725,00043 Days on yellowkey MLS ID: N6143349
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2557 Built: 2002Monthly Fee: $414 Tax: $6,305 (2025)Community: Boca RoyaleSpa: YesSingle Family
Taxes:$6,305
Remarks: One or more photo(s) has been virtually staged. Tucked within the sought after community of Boca Royale Golf and Country Club, this thoughtfully designed residence offers a refined blend of comfort, privacy, and Florida lifestyle living. Surrounded by mature landscaping and overlooking a peaceful pond, the setting creates a sense of calm the moment you arrive. Built by Thompson and offering over 2,500 square feet of living space, this three bedroom, two bathroom home features a well designed split floor plan that balances open gathering spaces with quiet retreats. Large windows and hurricane rated sliders invite natural light inside while framing tranquil water and garden views. At the center of the home, the updated kitchen combines both function and style. Soft close cabinetry, granite countertops, and a gas cooktop create an inviting space for everyday cooking or hosting friends and family. The layout flows easily into the main living and dining areas, allowing conversation and connection to continue throughout the home. Outdoor living is equally appealing. Step outside to the pool and spa area where you can unwind while enjoying the pond view and lush surroundings. A private garden courtyard offers an additional outdoor retreat perfect for morning coffee, quiet reading, or container gardening. The primary suite provides a peaceful place to recharge, while the split bedroom layout allows guests or additional household members to enjoy their own private space. A whole house generator offers added peace of mind. Located within Boca Royale, residents enjoy a gated community known for its beautifully maintained grounds and golf course lifestyle. Nearby beaches, marinas, dining, and shopping in Englewood and Venice add to the appeal of this exceptional location. This home offers the space, setting, and features that make everyday living feel both comfortable and elevated. Reach out to schedule your showing today!
Listing is courtesy of: PARADISE EXCLUSIVE INC (941-698-0303)
Listing Agent: Stephanie Ham (941-661-1462)
1089 BAYSHORE DR, ENGLEWOOD, FL 34223
$2,300,000130 Days on yellowkey MLS ID: N6141853
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3214 Built: 1979 Tax: $13,245 (2024)Community: Englewood GardensSpa: NoSingle Family
Taxes:$13,245
Remarks: Waterfront Legacy Estate on 1.57 Acres with Dock, Bay Views & Income Potential An extraordinary waterfront sanctuary spanning 1.57 acres with more than 200 feet of pristine Bay frontage, this exceptional estate commands breathtaking views across Lemon Bay and offers a rare blend of privacy, elegance, lifestyle and long-term opportunity. Arrive through a gated entrance and sweeping circular drive to discover a secluded coastal retreat framed by mature, thoughtfully curated landscaping. Fully furnished and impeccably presented, the residence is designed for effortless waterfront living — whether hosting family gatherings, welcoming guests arriving by boat, or enjoying quiet mornings watching the water awaken from your private balcony. Inside, soaring 23-foot floor-to-ceiling windows create a dramatic sense of scale while perfectly capturing the shimmering Bay beyond. The open-concept great room flows seamlessly into the gourmet kitchen and refined dining space, ideal for entertaining on any scale. The chef’s kitchen is a showpiece, featuring brand-new premium appliances including double wall ovens, a warming drawer, wine cooler, French-style refrigerator, granite-adorned center island and bespoke finishes throughout. Four beautifully appointed bedrooms and three luxurious bathrooms include a serene primary suite with its own private water-view balcony — a peaceful haven overlooking the Bay. Outdoor living is equally compelling. Expansive decks spill toward the resort-style pool, newly upgraded equipment and sun-soaked entertaining zones creating a seamless indoor-outdoor experience. A brand-new metal roof provides both architectural finish and long-term peace of mind. At the water’s edge, a newly constructed private dock offers direct Bay access — perfect for cruising Lemon Bay, kayaking at sunrise, or welcoming friends arriving by boat for sunset drinks beside the pool. The lower level features walk-out access to the pool terrace along with a convenient laundry and pool bath, making entertaining and waterfront living completely effortless. A Rare Opportunity for Future Growth & Income Beyond its immediate lifestyle appeal, the expansive acreage presents outstanding potential for long-term wealth creation. The generous grounds invite consideration for a guest residence, subdivision or luxury retreat accommodation — opening the door to Airbnb income streams or multigenerational living in a premier waterfront setting (subject to local approvals). Optional membership to the Englewood Gardens Beach Club further elevates the offering, granting access to a private beachfront clubhouse, gazebo with gas grills, Bayfront kayak launch, storage facilities and complimentary beach parking. From sun-drenched afternoons by the pool to evening cruises across the Bay, every detail of this property has been designed to inspire tranquility, prosperity and lasting memories. This is more than a home. It is a waterfront legacy — a place where lifestyle, luxury and long-term vision converge.
Listing is courtesy of: PREFERRED PROPERTIES OF VENICE INC (941-485-9602)
Listing Agent: Justyna Obiedzinski (862-686-1172)
1155 FOREST DR, ENGLEWOOD, FL 34223
$625,00023 Days on yellowkey MLS ID: D6146875
REDUCED by $24,000 (3.7%) on 04/23/2026
Bed: 4 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 1915 Built: 1974 Tax: $4,489 (2025)Community: Englewood Gardens Unit 4Spa: NoSingle Family
Taxes:$4,489
Remarks: This is not your typical Englewood remodel. 1155 Forest Dr is a four-bedroom, two-bathroom residence that has been completely reimagined with a modern contemporary design you simply won't find anywhere else in the area. From the moment you step inside, the dramatic skylights command your attention — natural light floods the living spaces and plays off the beautiful new vinyl flooring that flows seamlessly throughout the home. Floor-to-ceiling windows line the main living areas, dissolving the boundary between interior and exterior while framing the lush tropical surroundings. The kitchen has been fully redesigned with sleek cabinetry, a flush-mount range hood, and designer finishes complemented by a custom wood slat feature wall. Both bathrooms have been taken down to the studs and rebuilt with modern fixtures and clean, sophisticated lines. Every detail feels considered and intentional. The outdoor living is where this property truly separates itself. A fully enclosed courtyard and pool connect directly to a private cabana house — all under one continuous screen enclosure. The cabana features a thatched ceiling with exposed beam trusses, string lighting, a ceiling fan, and a mounted TV — an exceptional space for hosting or simply unwinding in total privacy. Adding to the property's versatility is a brand new detached garage, just completed by the current owner. Whether it's a workshop, additional storage, or a place for toys and projects, it's a rare addition that most homes in this area simply don't offer. The lot itself is .62 acres — an oversized, deeply private parcel with mature oaks, palms, and tropical vegetation creating an enveloping canopy that gives the entire property an effortless, resort-like feel. Impact-resistant windows (2021), a newer AC system (2019), a durable metal roof (2006), and relined plumbing round out the practical upgrades. Located minutes from historic Dearborn Street, Englewood Beach, golf courses, pickleball courts, and multiple boat ramps with direct access to open water. This is a one-of-a-kind property — schedule your private showing today.
Listing is courtesy of: LASBURY-TRACY REALTY INC. (941-474-5585)
Listing Agent: Austin Tracy (941-387-4259)
1175 LITTLE CT, ENGLEWOOD, FL 34223
$500,0008 Days on yellowkey MLS ID: D6147064
1 Days Off yellowkey (back on 4/24/2026)
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 720 Built: 1958 Tax: $3,665 (2025)Community: Englewood ShoresSingle Family
Taxes:$3,665
Remarks: Under contract-accepting backup offers. Your Island Escape on Manasota Key Awaits, Where Deeded Beach Access Makes Sunset Views Over the Gulf Part of Everyday Living. This furnished and beautifully remodeled two bedroom, one bathroom cottage with impact windows offers an inviting blend of comfort and charm, ideal as a seasonal retreat, an income producing investment, or a private getaway, all set within a relaxed, easygoing setting where tiki bars, sunshine, and warm salty breezes are part of daily life. The paver driveway, seagrape hedge, xeriscaped shell lawn, and screened lanai with sky blue exterior accents on the siding and shutters immediately set the tone and put you in a vacation state of mind. Step inside to find wood look tile flooring throughout for easy maintenance, paired with thoughtful decorative touches including shiplap walls, white shaker style soft close kitchen cabinetry, marble countertops and backsplash, and upgraded lighting and hardware that bring a polished, updated feel. Both bedrooms feature reach-in closets, while the bathroom offers a tiled shower with a frameless glass accent wall. After a day on the sand, the fully enclosed outdoor shower provides the perfect place to rinse away the salt and unwind before relaxing on the screened-in patio that is west facing so you can watch the sun go down with your favorite cocktail. Extensive 2025 updates include the roof, HVAC, appliances, flooring, cabinetry, and more, creating a like-new living experience. Located at 1175 Little Court in the Englewood Shores section of Manasota Key, the property includes deeded beach access points, with the south end location placing you near Stump Pass Beach State Park. The area is known for its quiet shoreline, natural surroundings, and relaxed atmosphere, with convenient access to boating, fishing, and waterfront dining, along with the ease of a quick golf cart ride to several local restaurants and bars offering live entertainment. Manasota Key itself has long been appreciated for its Old Florida character, where unspoiled stretches of beach, abundant wildlife, and a slower pace of life have been preserved over time, creating a setting that continues to feel authentic, laid back, and connected to the natural beauty of the Gulf Coast.
Listing Agent: Carla Stiver, Pa (941-270-1460)
1981 BAYSHORE DR, ENGLEWOOD, FL 34223
$1,195,0002 Days on yellowkey MLS ID: D6147155
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2566 Built: 1993 Tax: $7,373 (2025)Community: Englewood GardensSpa: YesSingle Family
Taxes:$7,373
Remarks: ***SELLER FINANCING AVAILABLE*** DECRA METAL TILE ROOF • SOLAR PANELS • IMPACT WINDOWS AND DOORS • HEATED SALTWATER POOL & SPA • EV CHARGING STATION Come discover this unique and secluded Florida Estate providing solid peace of mind during storm season. This exceptionally private and energy efficient two-story home is situated in the midst of lush native landscaping on a massive 1.12 acre gated property around the corner from Manasota Beach. The home sustained no damage during recent storms thanks to major structural improvements throughout. The property is fully enclosed with an 8-foot reinforced concrete wall and gated access at both the front and rear creating a secure, private setting with no HOA restrictions. As you enter through the gate into the expansive paver courtyard, the setting creates a true sense of separation from the outside. An 18’x45’ PebbleTec gas heated pool and spa is centered in the back yard just steps away from the screened lanai. Other outdoor features include a 75’ x 50’ deck, a 50’ pergola with partial operable roof, secure space for RV and boat parking, and an incredible entertaining area. A fully remodeled main-level primary suite features dual vanities, a walk-in shower, and custom closet. The kitchen features granite countertops and gas appliances, including a Wolf range. Interior finishes include a mix of Acacia wood, tile, and carpet, along with plantation shutters throughout. Additional features include a two-story family room with a gas fireplace, formal dining area, and a dedicated office/den with a built-in bookcase. The second floor includes three additional bedrooms and a full bath off of the loft area. A pocket door provides added privacy for two of the bedrooms and bathroom. The attached two-car garage includes an Electric Vehicle Charging Station for convenience and efficiency. A roomy detached garage allows for additional storage and a workspace, plus room for vehicles or toys. The property also includes a new irrigation system, underground 275 gallon propane tank, and outdoor kitchen propane hook-up. Optional access to the Manasota Beach Club is included, and the public boat ramp and beach are just around the corner. Come experience this rare gem in the heart of Old Florida!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Grier Crosby (757-714-1577)
43 WINDSOR DR, ENGLEWOOD, FL 34223
$469,00011 Days on yellowkey MLS ID: O6399230
INCREASED by $20,000 (4.5%) on 04/23/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1704 Built: 1973Monthly Fee: $8 Tax: $2,809 (2025)Community: Englewood Isles SubSingle Family
Taxes:$2,809
Remarks: Welcome to this beautiful pool home completly renovated and located in the desirable community of Englewood.Isles Access to a 27 ft. Boat dock in the marina a few blocks away. This charming residence at 43 Windsor Dr has a spacious layout with ample natural light throughout. The kitchen boasts brand new modern appliances and generous cabinet space. The island is large and hides 6 cupboards underneath. People love the kitchen layout. It's appropriate for cooking enthusiasts with an induction stove/oven. Enjoy the serene lanai with a perfect sized pool appropriate for outdoor relaxation. Primary suite has a six foot soaking tub plus a separate shower. Guest bathroom has a 4 ft x 4 ft rain box shower. The two guest bedrooms are large and bright. Conveniently situated near local amenities and stunning beaches, this property provides a wonderful opportunity for comfortable living. Selling furnished.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
115 WINSON AVE, ENGLEWOOD, FL 34223
$415,00024 Days on yellowkey MLS ID: C7523714
0 Days Off yellowkey (back on 4/23/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1040 Built: 1957 Tax: $3,404 (2025)Community: Englewood ParkSingle Family
Taxes:$3,404
Remarks: Under contract-accepting backup offers. Welcome to 115 Winson Avenue—where coastal charm meets next-level construction and income-producing potential in the heart of Englewood. Just steps from Historic Dearborn Street with its vibrant dining, shops, and year-round events, this 3-bedroom, 2-bath home offers partial bay views and a lifestyle that’s hard to match. Completely transformed in 2023, this is not just an update—it’s a structural upgrade, featuring reinforced concrete construction, raised interior floors for added flood protection, hurricane-impact windows and doors, a metal roof, and energy-efficient closed-cell spray foam insulation—delivering both peace of mind and major insurance advantages. Inside, the home showcases a beautifully updated, move-in-ready interior with a stunning chef’s kitchen highlighted by two-tone cabinetry, stainless steel appliances, farmhouse sink, open shelving, and custom finishes, complemented by wood-look tile flooring throughout. Both bathrooms have been thoughtfully renovated with stylish, high-end details, while the home also includes a dedicated interior laundry area, custom pantry, and built-in closet systems for optimal functionality. Step outside to enjoy a covered rear porch with pavers, a pergola with ambient lighting, hammock-ready relaxation spaces, and a detached metal-roof carport that offers covered parking and extra storage, with ample space to keep your boat right at home. Just minutes away, Indian Mound Park and Lemon Bay provide easy water access, kayaking, and stunning sunsets, while nearby parks and nature trails add to the appeal. Whether you're looking for a primary home, vacation retreat, or income-producing Airbnb, this property is ready to go.
Listing is courtesy of: RE/MAX PALM REALTY (941-743-5525)
Listing Agent: Taylor Brady (239-896-6433)
275 S MANGO ST, ENGLEWOOD, FL 34223
$200,000291 Days on yellowkey MLS ID: D6142989
0 Days Off yellowkey (back on 8/3/2025)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2002 Built: 1959 Tax: $2,080 (2024)Community: Palm Grove In EnglewoodSingle Family
Taxes:$2,080
Remarks: Under contract-accepting backup offers. Investor Special – Downtown Dearborn Opportunity! Endless potential awaits with this rare investment opportunity located just steps from the heart of charming Downtown Dearborn Street. Situated on three lots, this 3-bedroom, 2-bathroom home with an office, offers the perfect canvas for a full renovation or a brand-new build. The existing structure features a cozy fireplace and mature tropical landscaping—including a beautiful, fruiting mango tree—that provides natural privacy and Old Florida charm. Whether you're looking to restore the current home or start fresh, the spacious lot gives you the flexibility to bring your vision to life. The home has hurricane damage and is in need of major repair/cleanup. Unbeatable location—just minutes to local beaches, shopping, dining, and entertainment. Walk or bike to everything Englewood has to give! Don’t miss this chance to invest in one of the most desirable areas in town.
Listing Agent: Brittany Essig (941-626-0632)
928 STEWART ST, ENGLEWOOD, FL 34223
$500,0009 Days on yellowkey MLS ID: N6143942
0 Days Off yellowkey (back on 4/22/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1480 Built: 1970 Tax: $4,152 (2025)Community: Englewood Homeacres Lemon BaySpa: YesSingle Family
Taxes:$4,152
Remarks: Under contract-accepting backup offers. What a slice of Paradise! Completely renovated home with a boat slip across the street, a bike ride to Dearborn St. and a few miles to Manasota Beach or Englewood Beach! Perfect Primary home, vacation home or Airbnb! $23,651.80 booked right now for the next year! (bookings can be cancelled if you want to occupy) 3 Bedrooms 2 baths, 1 car garage, beautiful refreshing pool with a Heater/Chiller, a saltwater hot tub and an Authentic Tiki Hut. You also get a huge privacy fenced backyard with a "she shed" Park your boats, RV's, whatever you wish. The home features Plantation Shutters, all newer appliance's, gorgeous open kitchen with custom cabinets and stone counters and backsplash, all impact windows, newer metal roof and comes turnkey furnished. There is plenty of room with a living room, a back Florida room, inside Utility room a pool bath and a screened lanai. The 3rd bedroom features barndoors for either a bedroom, extended living room or an office. What more can you ask for? Come take a look!
Listing is courtesy of: SETTLES REAL ESTATE LLC (941-685-3600)
Listing Agent: Buck Settles (941-685-3600)
373 ARDENWOOD DR, ENGLEWOOD, FL 34223
$769,00093 Days on yellowkey MLS ID: D6145732
1 Days Off yellowkey (back on 4/22/2026)
REDUCED by $21,000 (2.7%) on 04/07/2026
Bed: 3 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2384 Built: 2002Monthly Fee: $10 Tax: $4,691 (2025)Community: Englewood Isles SubSpa: NoSingle Family
Taxes:$4,691
Remarks: MAJOR PRICE IMPROVEMENT - Embrace the art of coastal living in Englewood Isles. This coveted waterfront community offers more than a place to live — it delivers a lifestyle defined by boating, sun-kissed beaches, natural beauty, and a relaxed yet refined neighborhood atmosphere, all just moments from excellent dining and everyday conveniences. With scenic canals, mature tropical surroundings, and a welcoming sense of community, it’s easy to understand why so many choose to call this enclave home. Perfectly positioned along one of Englewood Isles’ picturesque canals, this residence captures the essence of Florida living. Here, mornings begin with calm water views and evenings unfold to the gentle rhythm of coastal life. Whether you’re setting out for a day on the boat or simply watching dolphins and manatees drift past, the connection to the water is ever-present and undeniably special. Inside, light-filled interiors and an easy, flowing layout invite both comfort and connection. Expansive sliding glass doors dissolve the boundary between indoors and out, creating an effortless transition to the waterfront — ideal for quiet mornings with coffee, intimate sunset gatherings, or hosting friends and family. A private dock and boat lift elevate the experience, allowing spontaneous adventures on the water to become part of your everyday routine. Beyond your doorstep, the best of the Gulf Coast awaits. Manasota Key and Englewood Beach are just minutes away, along with the charm of Historic Dearborn Street, world-class fishing, kayaking, golf, and an array of inviting dining options. Despite its proximity to everything you need, Englewood Isles remains a serene retreat — peaceful, established, and beautifully unhurried. Whether you envision this as your full-time residence, a winter escape, or a refined waterfront investment, this home offers a rare opportunity to live where every day feels intentional, effortless, and inspired by the water. Discover why Englewood Isles is truly one of Englewood’s best-kept coastal secrets.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-473-7750)
Listing Agent: Jim Litton, Pa (941-822-9648)
233 N NEW YORK AVE, ENGLEWOOD, FL 34223
$195,000330 Days on yellowkey MLS ID: C7510471
2 Days Off yellowkey (back on 4/21/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 400 Built: 1951 Tax: $2,351 (2024)Community: Lasbury Pineacres EnglewoodSpa: NoSingle Family
Taxes:$2,351
Remarks: Under contract-accepting backup offers. REDUCED!!! SUPER CUTE COTTAGE MADE EVEN CUTER WITH ITS BRAND NEW METAL ROOF!! Charming Florida cottage just steps from Historic Dearborn Street and a short bike ride to Englewood Beach! This efficient, move-in-ready home is the perfect coastal getaway, seasonal retreat, or income-producing property. Located in the highly sought-after Historical Dearborn Street District, you’ll enjoy being within walking distance of popular local attractions including farmers markets, car shows, boutique shopping, restaurants, and live entertainment. Offered turnkey furnished, this small but mighty home is ready for immediate occupancy or use as an annual rental or vacation rental (VRBO/Airbnb). The spacious fenced backyard is ideal for relaxing in the Florida sunshine—perfect for a garden, grilling, or entertaining. Outdoor enthusiasts will appreciate being just minutes from Indian Mound Park, which features a public boat ramp for easy access to Lemon Bay. Additional highlights include no HOA fees, no CDD fees, and a location in a preferred flood zone, meaning flood insurance is not required by a lender. Don’t miss this rare opportunity to own a slice of paradise in one of Englewood’s most desirable and walkable neighborhoods!
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Traci Creighton (941-451-9419)
157 ENGLEWOOD ISLES PKWY, ENGLEWOOD, FL 34223
$629,00061 Days on yellowkey MLS ID: D6146260
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2152 Built: 1991Monthly Fee: $11 Tax: $3,964 (2025)Community: Englewood Isles SubSpa: YesSingle Family
Taxes:$3,964
Remarks: Welcome to this stunning turnkey furnished waterfront pool home located in the desirable Englewood Isles. This 3-bedroom, 2-bathroom residence offers a perfect blend of comfort and luxury with quick access to Lemon Bay and the Gulf, making it a boater's paradise. Step outside to the large lanai, where you'll find a sparkling pool with a spa, perfect for relaxing while enjoying breathtaking water views. The home features a composite dock, ideal for docking your boat, and a convenient outdoor shower. Inside, the split bedroom floor plan provides privacy and convenience, while the spacious master suite boasts dual closets and sliders leading directly to the lanai. The master bath includes a walk-in tile shower and dual sinks. The open kitchen is a chef’s dream, with a breakfast nook, closet pantry, and plenty of counter space for meal prep. The light-filled living areas feature pocket sliders that seamlessly connect the indoors to the outdoor living space. The third bedroom is generously sized, with its own set of sliders to the pool area, making it an ideal Florida room or guest retreat. Additional features include an inside laundry room, a screened front entry, and hurricane shutters for peace of mind. The 2022 roof ensures years of worry-free living. This home is just minutes from pristine beaches, fantastic restaurants, world-class fishing, golfing, and shopping. Don’t miss the opportunity to own this exceptional waterfront property!
Listing Agent: Becky Cole (941-525-8311)
1828 WHISPERING PINES CIR, ENGLEWOOD, FL 34223
$549,900393 Days on yellowkey MLS ID: D6139707
0 Days Off yellowkey (back on 4/20/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2695 Built: 1999Monthly Fee: $25 Tax: $5,878 (2025)Community: Englewood PinesSingle Family
Taxes:$5,878
Remarks: Under contract-accepting backup offers. TIRED OF THE SAME 'FLORIDA' LOOK? Want a home with character? Take a look at this CUSTOM BUILT ONE OWNER HOME in prestigious Whispering Pines subdivision, conveniently located in North Englewood, with easy access to Manasota Beach, Venice or Englewood! From the front porch (picture having your morning coffee out here, sitting in your rocking chair) you'll enter into the Great room featuring both a wood and gas fireplace, Brazilian Rosewood hardwood flooring, vaulted ceiling with tubular skylight and pocket sliding glass doors on to the lanai. The separate dining room also has hardwood flooring and a genuine TIN CEILING. An office/den/library is just off the main entry and has bamboo flooring, ceiling fan, and walk in closet - THIS COULD BE A 4TH BEDROOM! The kitchen has oak cabinetry and solid surface countertops, closet pantry and breakfast bar. Appliances include: Whirlpool dishwasher, Maytag cooktop plus built in oven, and GE French door refrigerator. The adjoining dinette area has tiled flooring and French doors opening onto the lanai. The primary bedroom has a 2' bumpout for extra floor space, tray ceilling and ceiling fan, hardwood flooring, two walk in closets and another set of French doors. The primary bathroom has a Roman walk in shower, linen closet and vanity w/cultured marble top. The other two guest bedrooms are on the opposite side of the house - the rear guest bedroom has wood laminate flooring, ceiling fan and wall closet. The Front guest bedroom also has wood laminate flooring, wall closet, ceiling fan and a your very own SAUNA! Guest bath features a combo jetted tub/shower, linen closet and tiled flooring. Nicely sized inside laundry has lots of extra cabinetry for storage and a built in utility tub. Take the circular stairs up to the 2nd floor to find all kinds of extra space - picture a media room, playroom, mancave, or whatever! Half bath is handily located here also, as is a wet bar! There's a "sweetheart" balcony off this area, for a great view! Two car garage w/divided stalls has automatic garage door openers, and built in shelving and workbench. Tankless water heater provides hot water instantly! In the rear, you'll find the lanai and caged atrium... this would be a wonderful place for a hot tub, or maybe an outside kitchen? There's a bridge over the meandering creek. offering plenty of natural foliage for all of the wildlife. Home is in an "X" flood zone, so your lender will not require you to have flood insurance. Access to the rear of the property is through a deeded easement off of Keyway Road. Roof is original and is a 50 year shingle. Dual AC systems. (compressors have been updated) If you are seeking a large unique home with some land and privacy, take a look at this one!
Listing Agent: Kathy Damewood (941-321-7355)
19 N CAYMAN ISLES BLVD, ENGLEWOOD, FL 34223
$925,00025 Days on yellowkey MLS ID: A4687622
1 Days Off yellowkey (back on 4/15/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3065 Built: 1998Monthly Fee: $423 Tax: $6,871 (2025)Community: Boca RoyaleSingle Family
Taxes:$6,871
High School: Wellen Park High
Remarks: Under contract-accepting backup offers. Located in the gated Boca Royale Golf & Country Club, this lakefront residence offers water views from both the front and rear—perfect for enjoying Florida sunsets. Privately positioned on an oversized homesite designed for indoor-outdoor living, the home features mature palms and tropical landscaping, a screened lanai with an elegant paver deck, saltwater pool, and fully equipped outdoor kitchen with gas grill and dual refrigerators, creating a private, resort-inspired retreat. As evening falls, curated landscape lighting illuminates the property and architectural details, casting a warm glow and enhancing the home’s captivating nighttime ambiance. Inside, sophistication and comfort blend effortlessly. Glass French doors open to a light-filled interior featuring soaring ceilings, crown molding, plantation shutters, and expansive tile flooring throughout the main living areas. The kitchen is open to the oversized family room, perfect for entertaining is appointed with stainless steel appliances, double ovens, a French-door refrigerator, cooktop, 42-inch custom cabinetry, granite countertops, and a spacious center island with abundant storage. A raised breakfast bar opens seamlessly to the main living area with a custom entertainment center and direct lanai access, ideal for relaxed yet elegant living. The private primary suite is a true retreat, offering direct access to the lanai, plantation shutters, custom wood accent wall, dual walk-in closets, and a spa-inspired bath with a soaking garden tub, walk-in shower, dual vanities, and a private water closet. Guest accommodations on the opposite side of home, including 2 large bedrooms with hall bath and in the back of the home off the lanai is a versatile room with custom built-ins that offers a flexible space for a 4th bedroom, executive office, or private guest suite. Additional highlights include NEW PAVERS in front driveway and side walkway, an oversized laundry room with extensive storage and utility space, plantation shutters throughout, a chic half bath for guests, and an oversized 2.5 CAR GARAGE with dedicated golf cart storage. Storm Smart Wi-Fi-enabled hurricane screens at the lanai and front entry, along with a GENERAC WHOLE HOME GENERATOR, provide added comfort and peace of mind. Ideally located just a short golf cart ride from the desired Boca Royale Golf & Country Club, residents enjoy access to an exclusive members-only lifestyle featuring a championship Gordy Lewis-designed golf course, tennis and pickleball courts, fitness and wellness amenities, fine dining, and a vibrant social calendar. Also, future plans of direct access to Wellen Park through the new Boca East section. This is more than a home—it is a statement of privacy, luxury, and elevated Florida living.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Brandi Furlan (941-894-9888)
14 STONE MOUNTAIN BLVD, ENGLEWOOD, FL 34223
$399,90040 Days on yellowkey MLS ID: N6143412
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1698 Built: 1974Monthly Fee: $10 Tax: $2,747 (2025)Community: Englewood Isles SubSpa: NoSingle Family
Taxes:$2,747
Remarks: This is a great price for this 3 bedroom pool home in the popular boating community of Englewood Isles. This home has been meticulously maintained and is being sold TURNKEY FURNISHED. In this great home you'll find BRAND NEW IMPACE WINDOWS AND DOORS and the tile roof is only 10 years old, so insurance will be no problem here AND it's not in a flood hazard zone! All the appliances are less than 5 years old and you'll enjoy many hours of relaxation and entertaining on the huge lanai with HEATED pool and recently remolded pool with new pool surface, all new pavers and a NEW POOL CAGE. You'll also enjoy a separate uncovered patio great for grilling. The floorplan is very versatile with the ability to have a formal dining room or a front dining room and a back family room. It also features a split floorplan with 2 guest bedrooms on the opposite side of the home from the primary bedroom. The EAT IN KITCHEN features newer appliances, shiplap ceiling and a handy closet pantry plus a slider to the lanai. The guest bedrooms are both generous in size and the primary bedroom features an ensuite bath and big walk in closet. Englewood Isles is a great waterfront community with a private marina on Forked Creek. Docks are usually available to purchase or rent to only Englewood Isles residents. There are no bridges to the Intracoastal from the marina and it's a pretty boat ride down Forked Creek. Put all this together with an X500 flood zone, fully furnished and you have a winner!
Listing is courtesy of: MEDWAY REALTY (941-375-2456)
Listing Agent: Katy Dilmore (941-270-0627)
4 WINDSOR DR, ENGLEWOOD, FL 34223
$599,000477 Days on yellowkey MLS ID: N6135900
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1782 Built: 1972Monthly Fee: $10 Tax: $6,020 (2024)Community: Englewood Isles SubSingle Family
Taxes:$6,020
Remarks: REDUCED!!!Come see this true Unicorn of Florida Gulf Access homes--this one is NOT in a flood zone and does NOT require flood insurance!! You Found It!!!Imagine--all that waterfront beauty; just 30 minutes and no fixed bridges to the glorious Gulf--and NO flood insurance required. How sweet is that? For maximum ease the seller may consider selling this beautifully furnished home turnkey. There are custom window and patio door treatments, upgraded Berber carpet in bedrooms and Florida room; plus wireless remote controlled multifunction ceiling fans and lights. Spend a leisurely morning in your lovely Florida room overlooking the water where manatees and dolphins play. Some of the best fishing is right in your back yard. The interior was completely remodeled in 2018, and is open, light and bright. Thoughtful perks include a central vacuum with a set of hoses for the garage and a separate set for the house to make your life easier. The den could be used as a third bedroom, and the split plan allows maximum peace and privacy. The updated kitchen features stainless and stone, and the spacious waterfront Florida room is marvelous for entertaining. There is even a protected private marina just for residents. Fancy a picnic at the beach? North Beach is just 9 little minutes from home! Prefer waterfront dining? The area's best is minutes from your house. Dearborn Street with shops, dining, galleries, hot rods and the Best Farmer's Market in the county is less than 10 minutes away. Englewood Isles has been Englewood's best address for over half a century, with peaceful tree lined streets and generous lots. Why settle for an anonymous beige box on a postage stamp lot? Your new home in Englewood Isles awaits!
Listing is courtesy of: WHITE SANDS REALTY GROUP FL (941-923-5835)
Listing Agent: Amy Hibberd (941-228-6900)
6 PINE RIDGE WAY, ENGLEWOOD, FL 34223
$425,00022 Days on yellowkey MLS ID: N6143740
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1916 Built: 1973Monthly Fee: $10 Tax: $3,821 (2025)Community: Englewood Isles SubSpa: NoSingle Family
Taxes:$3,821
Remarks: Welcome to the desirable boating community of Englewood Isles. Open the door to find a bright open living room with a triple pocket slider to the lanai and pool area. The SPLIT FLOORPLAN insures privacy for you when having guests. Both of the guest bedrooms are generous in size and the guest bath features updated vanity and tile enclosed tub/shower combination. The Primary bedroom on the opposite side of the home is also large and features ensuite bathroom with updated double sink vanity, updated tile enclosed walk in shower and a tray ceiling with crown molding. There's also a door to the garage making it handy for you messy lawn person to clean up without going through the house. The dining area in the front of the house has large windows and updated lighting fixture. The living room also has an updated ceiling fan and is light and bright. The handy INSIDE LAUNDRY room has a storage cabinet and also has a door to the 2 car garage that has an impact rated garage door. The EAT-IN kitchen has been updated with quartz countertops, soft close doors and drawers, tray ceiling with crown moldings and a slider to the pool area. Beyond the kitchen you'll find a cozy family room with lots of windows making it light and cheery. The decorative chair rail and crown molding adds to the charm of this room. This home has all impact windows with the exception of the bathroom and 2 slider doors. It has also been re-piped overhead. Outside you'll find a nice covered patio with ceiling fan and a separate uncovered patio for catching some sun rays or great for BBQ's. Relax and cool off in your kidney shaped pool with screen enclosure and mature landscaping. All this and situated in desirable Englewood Isles less than 3 miles to Manasota beach and features a private marina on Forked Creek with no bridges to the Intracoastal waterway. Docks are individually owned and have water & electric. Dock owners and renters must be residents of Englewood Isles.
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