Townhomes Of San Simeon Homes with Gated Community Type

Welcome to the Townhomes of San Simeon, an idyllic gated community nestled in the heart of Fort Myers, Florida. This charming subdivision is designed for those who appreciate both privacy and a vibrant community lifestyle. With its picturesque landscapes and meticulously maintained grounds, San Simeon offers a serene escape while remaining conveniently close to the bustling attractions of Fort Myers.

The Townhomes of San Simeon feature beautifully crafted residences that blend modern elegance with comfort. Each townhome is thoughtfully designed with spacious floor plans, high ceilings, and contemporary finishes, providing a perfect backdrop for both relaxation and entertaining. Residents can enjoy the luxury of private outdoor spaces, ideal for soaking up the Florida sun or hosting gatherings with friends and family.

One of the standout features of this community is its gated entrance, ensuring a safe and secure environment for all residents. The sense of community here is palpable, with friendly neighbors and a welcoming atmosphere that makes it easy to feel at home. The amenities are plentiful, including a sparkling pool, fitness center, and walking trails, catering to an active lifestyle.

Located in Lee County, Fort Myers is known for its stunning beaches, vibrant cultural scene, and abundant recreational opportunities. Whether you’re exploring the nearby nature preserves, indulging in local dining, or enjoying the arts, everything you desire is just a stone's throw away.

Discover the charm and convenience of the Townhomes of San Simeon, where your dream home awaits in a community that truly feels like family.

Newest Townhomes Of San Simeon Homes with Gated Community Type

$220,900

2 Beds ⋅ 2.5 Baths ⋅ 2026029734 MLS ⋅ Townhomes Of San Simeon BLDG.

Fantastic two bedroom, two and a half bath townhouse with a two-car garage, located in the Townhomes of San Simeon gated community. Beautiful kitchen with a pantry, tall white cabinetry, tile countertops, recessed lighting, pass-through opening to the main living area, and eat-in kitchen breakfast nook or informal dining area. Bright, open main living and dining area with access out to the screened lanai. There is a half bath on the first living level with tile flooring, a pedestal sink and a toilet. There are spacious bedrooms and two full bathrooms upstairs, as well as an upstairs laundry closet. The main bedroom offers a coffered ceiling, a large closet and an en suite main bath with dual sinks, a corner garden tub, and a separate large shower. The guest bathroom offers a tub-shower combination. The screened-in lanai offers a lovely landscaped view. Other features include: fresh interior paint, brick paver driveway, roof, screened lanai and impact windows and doors. Nice two car attached garage with finished garage floor. Move-in ready! This lovely community features a resort-style swimming pool, hot tub, a clubhouse with a fitness center, community room, and a recreation area. This townhouse is centrally located close to I 75, Colonial, US 41, SR 82, shopping, dining, and entertainment.

4092 Cherrybrook LOOP, Fort Myers

$235,000

3 Beds ⋅ 2.5 Baths ⋅ 2026040222 MLS

LIVE THE FLORIDA LIFESTYLE AT SAN SIMEON! This inviting 3-bedroom, 2.5-bath townhome offers 1,566 square feet of living space, a 1-car attached garage, and a versatile loft area. Recent improvements include a NEW ROOF IN 2024 and EXTERIOR PAINT IN 2023. NOTE: some pictures have been AI generated with furniture. The open-concept living and dining areas provide a comfortable space for everyday living and entertaining, while the kitchen features stainless steel appliances, pantry storage, and a breakfast bar. Upstairs, the spacious primary suite and additional bedrooms offer comfortable living space, along with the convenience of an upstairs laundry area. Step outside to the OVERSIZED PRIVATE LANAI and landscaped area, creating an ideal spot for morning coffee, relaxing in the Florida sunshine, or enjoying an evening outdoors. San Simeon offers a COMMUNITY POOL, CLUBHOUSE, AND FITNESS CENTER, providing residents with opportunities to stay active and enjoy the outdoors close to home. Conveniently located in Fort Myers with easy access to SHOPPING, DINING, I-75, AND MAJOR ROADWAYS. Southwest Florida beaches, parks, nature preserves, and recreational destinations are also within a convenient drive. Whether you are looking for a full-time residence, seasonal getaway, or low-maintenance Florida home, 3908 CHERRYBROOK LOOP offers the opportunity to enjoy the sunshine, outdoor living, and relaxed lifestyle that make Southwest Florida so appealing.

3908 Cherrybrook LOOP, Fort Myers

$255,000

3 Beds ⋅ 2.5 Baths ⋅ 2026039733 MLS ⋅ Townhomes Of San Simeon BLDG.

LOCATION, LOCATION, LOCATION! Position yourself near one of the area’s most exciting developments! Welcome to 4000 CHERRYBROOK LOOP, ideally located just a short distance from the NEW LEE HEALTH HOSPITAL CAMPUS, SLATED FOR COMPLETION IN EARLY 2028! With a major healthcare campus coming nearby, this townhome offers an exciting opportunity for INVESTORS, HEALTHCARE PROFESSIONALS, SEASONAL RESIDENTS, OR FULL-TIME BUYERS looking for convenience, amenities, and low-maintenance Southwest Florida living. Located within the beautifully maintained GATED COMMUNITY OF SAN SIMEON, this partially furnished 3-BEDROOM, 3-BATH TOWNHOME has so much to offer. Recent improvements include a NEWER A/C, NEWER FLOORING, FRESH INTERIOR PAINT, NEWER WATER HEATER, AND NEWER STOVE/OVEN. The spacious kitchen features GRANITE COUNTERTOPS AND AMPLE CABINETRY, providing plenty of room for everyday living and entertaining. Another major bonus—HURRICANE-IMPACT WINDOWS AND DOORS offer added protection and peace of mind. Step outside to your COZY SCREENED PATIO, perfect for enjoying your morning coffee or relaxing after a day in the Florida sunshine. Additional features include a GENERATOR HOOKUP and a garage offering extra storage space. Enjoy resort-style community amenities including a CLUBHOUSE, INVITING POOL AND SPA, FITNESS CENTER, AND PLAYGROUND, all surrounded by the lush landscaping and beautifully maintained grounds of San Simeon. INTERNET/WIFI is included! And when it comes to convenience, THIS LOCATION IS HARD TO BEAT! Enjoy easy access to RSW INTERNATIONAL AIRPORT, FORT MYERS-AREA BEACHES, SHOPPING, DINING, ENTERTAINMENT, AND THE NEW LEE HEALTH HOSPITAL CAMPUS. Whether you're looking for a PRIMARY RESIDENCE, FLORIDA GETAWAY, OR INVESTMENT PROPERTY, this townhome delivers a terrific combination of LOCATION, VALUE, AMENITIES, AND FUTURE POTENTIAL. Don't miss your opportunity to own in this ideally situated Southwest Florida community! SOME PHOTOS VIRTUALLY STAGED.

4000 Cherrybrook LOOP, Fort Myers

$250,000

3 Beds ⋅ 2.5 Baths ⋅ 226032128 MLS

Refreshed three-bedroom townhome featuring a spacious family/living room and a flexible area ideal for formal dining or a home office. The eat-in kitchen offers a breakfast bar and a complete stainless steel appliance package. The home includes 2.5 bathrooms, with a convenient half bath on the main level. Upstairs, the laundry area provides additional storage. Other highlights include an attached two-car garage and a screened patio. Conveniently located near the new hospital, the community offers numerous amenities, including a swimming pool and community room.

3846 Cherrybrook LOOP, Fort Myers

$245,000

3 Beds ⋅ 2.5 Baths ⋅ 2026036600 MLS

Sunny Southwest Florida is calling for you! This 3 bed 2 1/2 bath townhome is perfect for those who what a spacious living space, oversized corner lot and the security of a gated community located in the heart of town. Location is key with this community as it is less than 5 mins to I75 highway, 15 mins to thriving downtown river district entertainment, 25 mins to multiple beaches, and 3 mins to restaurants, grocery, large retailers shopping and hardware stores. Some nearby retailers include Super Walmart, Publix, Lowes, Top Golf, Whole Foods and much much more. The first floor includes the main living room area, eat in kitchen, 1/2 bath, attached garage and large screen lanai. The second floor includes 3 bedrooms with a master bath including shower only, large vanity top and linen closet master bedroom, guest bath, 2 additional guest bedooms, computer homework station loft area, laundry space huge walk in closet and HVAC equipment. The key interior features include granite counter tops, large 46" cabinets, ample pantry space, tile floors on the first floor, large windows double sliding glass doors, large screened lanai and attached single car garage. The bedrooms are larger than the standard and all have larger closets. This is a smaller community and very friendly safe and inexpensive compared to many other. The community offers a clubhouse with a large heated pool, hot tub, playground, fitness room and community room all along a large central lake with beautiful fountain. See attached floorplan from builder DR Horton along with features and construction data provided by builder. Schedule your private showing today!

3800 Clearbrook LN, Fort Myers

$249,900

3 Beds ⋅ 2.5 Baths ⋅ 226024253 MLS

Welcome to the the gated Townhomes of San Simeon community. This well-kept 3-bedroom, 3-bath townhome offers a practical two-story layout with a 1-car garage, granite countertops, stainless steel appliances, and comfortable living space designed for everyday convenience. Major updates include an A/C replaced in 2021 and accordion shutters for added storm protection and peace of mind. San Simeon offers a great Fort Myers location with resort-style amenities including a community pool, spa, clubhouse, fitness room, community room, and play area. Enjoy low-maintenance living close to shopping, dining, entertainment, parks, and Southwest Florida beaches. A clean, move-in-ready opportunity in a gated community with strong amenities and excellent convenience.

3916 Cherrybrook LOOP, Fort Myers

$219,000

3 Beds ⋅ 2.5 Baths ⋅ 2026027737 MLS ⋅ Townhomes Of San Simeon BLDG.

BEST-PRICED TOWNHOME IN SAN SIMEON! If value, location, and low-maintenance living are at the top of your list, this beautifully maintained 3-bedroom, 2.5-bath townhome deserves a closer look. Located in the gated San Simeon community, this home offers 1,313 square feet of living space, an attached garage, three spacious bedrooms, and an HOA that takes care of many of the exterior expenses—all in a convenient Southwest Florida location. The main level features a comfortable, functional layout with plenty of space for everyday living and entertaining, along with a convenient half bath. Upstairs, you'll find three generously sized bedrooms and two full bathrooms, including a spacious primary suite. Fresh paint on the second floor gives the home a clean, refreshed feel. The kitchen features granite countertops, wood cabinetry, stainless steel appliances, and a pantry. The refrigerator and microwave were replaced in 2025, and the laundry area includes a 2025 washer and dryer plus a large utility closet for additional storage. A major benefit of this home is the low-maintenance lifestyle. HOA dues include internet service and extensive exterior maintenance, including lawn care, landscaping, tree trimming, exterior painting, and roof replacement. Even better, the roof was replaced in 2024, providing valuable peace of mind for years to come. The home is offered partially furnished, making it easy to move in and start enjoying the Florida lifestyle. The seller is also open to providing a flooring allowance, giving the new owner an opportunity to make the space their own. San Simeon is a gated, pet-friendly community conveniently located near Gulf Coast beaches, shopping, dining, Florida Gulf Coast University, and Southwest Florida International Airport. Whether you're looking for a full-time home, seasonal retreat, or investment property, this is an opportunity to own in a desirable location while keeping maintenance and ownership expenses in check. With its competitive price, recent major improvements, included exterior maintenance, and convenient Fort Myers location, this is one of the standout values currently available in San Simeon. Be sure to view the 3D virtual tour!

3818 Clearbrook LN, Fort Myers

$235,000

3 Beds ⋅ 2.5 Baths ⋅ 226019178 MLS

One or more photo(s) has been virtually staged, AI generated or rendered. One or more photo(s) has been virtually staged, AI generated or rendered. SENSATIONAL SAN SIMEON!! Move-In-Ready, 3 bedroom + media loft, 2 1/2 bath, 1-car garage, spacious 2013 BUILT Townhome in the NEWEST SECTION OF THE COMMUNITY WITH LOWER FEES AND HIGHLY DESIRABLE FLOOR PLAN!! Features include NEW ROOF IN 2024, NEWER AC, open floor plan, lots of natural light, large kitchen with granite countertops and stainless steel appliances and tile floors throughout the ground level along with a convenient 1/2 bath. Upstairs you will find a large primary bedroom with en-suite and walk-in-closet, large guest bedrooms, bonus media loft with space for a desk and laundry. In need of some fresh air? Enjoy a large covered and screened lanai with brick paver decking and swing-door access to the backyard, tropical landscape, large driveway and so much more!! As for the neighborhood, it is wonderfully kept, beautiful and inviting with a great feel! Resort style amenities are just a short distance from the front door featuring a lakefront huge sparkling pool with tons of deck seating and lounges, large spa, fully equipped fitness center, tot lot playground and clubhouse! This gated community is set in a prime location close to the area's best parks, shopping, dining, entertainment and just a short drive to white sand, turquoise water beaches!! Call for your private showing today!

3806 Clearbrook LN, Fort Myers

$252,000

3 Beds ⋅ 2.5 Baths ⋅ 2026009168 MLS

Welcome to this beautifully refreshed 3-bedroom, 2.5-bath townhome in the gated community of San Simeon! This move-in ready residence showcases major 2024 updates including a new tile roof, new A/C system, new water heater, and fresh exterior paint—offering peace of mind from day one. Inside, enjoy tile flooring throughout the main level, freshly painted kitchen cabinetry paired with stainless steel appliances, and durable laminate flooring upstairs. The spacious owner’s suite features a walk-in closet and tranquil water views. Unwind on your screened lanai overlooking the pond, fountain, and clubhouse—your own private retreat. Additional highlights include Ring door security, keypad entry, and built-in garage storage. Residents enjoy internet service and resort-style amenities including a pool and hot tub, updated playground, fitness center, and clubhouse. Ideally located near I-75, Southwest Florida International Airport (RSW), shopping, dining, and the new Lee Health Fort Myers Hospital under construction just across the street. Located in a non-flood zone for added confidence. Schedule your showing today and experience the best of Florida living!

3935 Cherrybrook LOOP, Fort Myers

$349,000

3 Beds ⋅ 2.5 Baths ⋅ 2026000261 MLS

Beautiful, Newly renovated, 3-bedroom 2.5 bath 2 CAR townhouse! Lives like a single-family home, while offering an incredible location & great amenities, including clubhouse, large pool and spa area, exercise room and children's play area. Over 1876 sq ft under air & 2511 total sq ft! This home is in an excellent, gated community very close to great shopping, dining, schools, TopGolf, BJ's, Publix and more! The home is nestled into a private cul-de-sac, away from community traffic. Kitchen features newly updated everything!....wood cabinets, stainless appliances, exotic granite and subway backsplash. The entire home has new luxury vinyl flooring (no carpets). The screened lanai backs up to a preserve. The upstairs has split floor plan, with 3 bedrooms. HUGE primary bedroom has a custom, roomy walk-in closet. Beautiful primary bath with oversize Jacuzzi tub & shower with waterfall spray fixture. San Simeon's management team manages exterior pest control, irrigation & trash removal.

4048 Cherrybrook LOOP, Fort Myers

$295,000

2 Beds ⋅ 2.5 Baths ⋅ 225076219 MLS

It is time to take advantage of this recent PRICE IMPROVEMENT! Welcome to the beautiful Townhomes of San Simeon! This excellent ground-floor entry, two-story property is ready for you to move right in! This home features 2 beds and 2.5 baths, with a fantastic view of the community lake and clubhouse. Enjoy your afternoon cocktail or morning coffee while taking in breathtaking views and sunsets from the west-facing, extended screened lanai. Interior features of this excellent property include a Kitchen with smart-looking white cabinetry updated in 2020, 42-inch upper cabinets, an eat-in kitchen, stainless steel appliances, light tile floors, crown molding, and modern granite counters and backsplash. Additional features include tile floor throughout the first floor, LVT flooring throughout the second floor, plantation shutters on all windows, and the rear sliding door. Recent structural/mechanical updates include new community roofs (2024), a newer HVAC system (2021), and an updated water heater (2022). This home also features impact-resistant windows and a sliding rear door, a second-floor laundry, and an attached two-car garage. Townhomes of San Simeon amenities include a beautiful clubhouse, community pool and spa, and fitness center. This charming gated community is a short drive from area beaches, grocery stores, fabulous dining, and a multitude of amenities and shopping options. Located within 5 minutes of the new Lee Health Campus (presently under construction), as well as a 10-minute drive to the Lee Health Sports Complex, JetBlue Park, and lovely downtown Ft Myers. Welcome to the beautiful Townhomes of San Simeon!

3951 Cherrybrook LOOP, Fort Myers

Start Your Search

The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.