Location: Maitland
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1393 BENEVOLENT ST, MAITLAND, FL 32751
$379,000Listed 04/16/2026 12:02AM MLS ID: O6399560
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1674 Built: 2005Monthly Fee: $520 Tax: $3,322 (2025)Community: Enclave/Maitland A-FTownhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,322
Elementary School: Lake Sybelia Elem
High School: Edgewater High
Tax Year: 2025
Middle School: Maitland Middle
Remarks: This beautiful Maitland Florida town home feels like living in a gated resort! 3 bedrooms, 2 1/2 baths, plus garage and loaded with upgrades including hardwood floors on both levels, crown molding, tall wood cabinets, stone counters and so much more. Welcoming entry foyer with half bath, kitchen with island sink, large breakfast bar, stainless appliances, granite counters and custom backsplash. Inviting living room and dining area offer plenty of space for entertaining, french door opens to private covered porch which overlooks the rear yard. Upstairs the ensuite primary bedroom has a walk-in closet, great covered balcony area and a dual sink bathroom with glass enclosed shower. Additional 2 bedrooms in the front of the upstairs share a hall bath and laundry closet with washer and dryer included. Montacino is a gated European feeling award winning community with amazing pool area, lake frontage and a convenient location to shopping and i4. This townhouse has a quiet location within the community offering privacy in the back area. All exterior maintenance is included (roof and paint too)! HOA dues include new fiber with internet and channel package and all Montacino amenities.
Listing is courtesy of: RENCHER REALTY GROUP (321-325-2040)
Listing Agent: Daniel Rencher (407-279-1946)
1321 BENEVOLENT ST, MAITLAND, FL 32751
$384,00065 Days on yellowkey MLS ID: O6377413
REDUCED by $1,000 (0.3%) on 04/02/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1751 Built: 2006Monthly Fee: $520 Tax: $2,204 (2024)Community: Enclave/Maitland A-FTownhouse
Taxes:$2,204
Tax Year: 2024
Remarks: Seller is willing to contribute towards buyer's rate buydown with acceptable offer. RECLAIM YOUR TIME: Stop sacrificing your sleep and evenings to the I-4 commute. Located in the gated community of Montacino, this 3-bedroom, 2.5-bath (one owner) townhome sits at a convenient midpoint between Downtown Orlando and Sanford—approximately 15 minutes to each—offering everyday convenience for work and play. Snowbirds will appreciate the lock-and-leave ease and proximity to Orlando’s world-class amusement parks and beaches. MECHANICAL PEACE OF MIND: Meaningful updates include a new HVAC system (January 2025) and an appliance suite featuring a whisper-quiet Bosch dishwasher (2023) plus a new refrigerator and microwave (2026). This unit is truly move-in ready. DESIGNER INTERIORS: Engineered hardwood flooring flows through the living and dining areas, up the stairwell, and upper hallway. Fresh interior paint and updated designer lighting throughout create a bright, airy, and modern feel. THOUGHTFUL FLOORPLAN: The main level offers open-concept living with seamless flow from the kitchen to living and dining areas, plus a shaded, treed green space just off the rear porch. Upstairs, the generously sized primary suite provides room for a desk, reading nook, or even exercise equipment—a true retreat with flexible space to suit your lifestyle. Two additional bedrooms and a convenient second-floor laundry add to the home’s smart design. EXCEPTIONAL HOA VALUE: The community’s five-year bulk service contract includes high-speed internet, WiFi equipment, and an expanded television and streaming package, simplifying monthly bills and reducing out-of-pocket utility costs. COMMUNITY: Enjoy maintenance-free living with access to a resort-style pool, scenic walks along Lake Charity, and gated entry. Convenient to Winter Park, Downtown Orlando, and the North Orlando business corridor. A well-priced opportunity for a unit of this caliber in Montacino. LESS TIME COMMUTING, MORE TIME LIVING - MAKE CONTACT TODAY TO EXPERIENCE THIS HOME IN PERSON.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Shirley Jones (407-719-9180)
1161 CHARMING ST, MAITLAND, FL 32751
$599,00014 Days on yellowkey MLS ID: O6395711
REDUCED by $26,000 (4.2%) on 04/08/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2477 Built: 2006Monthly Fee: $520 Tax: $4,384 (2025)Community: Enclave/Maitland A-FTownhouse
Taxes:$4,384
Remarks: Sunrises over Lake Charity, two primary suites, and a kitchen made for serious cooking — this Montacino townhouse isn’t like anything else on the market. With 4 bedrooms, 3.5 baths, and new luxury vinyl flooring throughout, it’s effortlessly modern and move-in ready. The first-floor primary suite offers single-level living with a spa-inspired bathroom with two vanities, a tub and shower and generous closet space. The second-floor primary provides a private retreat for guests or family — a rare and highly sought-after layout. The brand new LG induction oven with air fryer and Café double dishwasher make cooking and cleaning a breeze, and the private back patio is perfect for morning coffee, entertaining or evening relaxation. An extra-large two-car garage adds plenty of storage for bikes, tools, or hobbies. Nestled in a gated community with a pool, this home blends comfort, security, and lifestyle convenience. With minutes to I-4, Winter Park, Downtown Orlando, and all of Maitland’s best dining and shopping are within easy reach. A rare floor plan, thoughtful updates, and flexible living spaces — this Montacino gem truly stands apart.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Allie George (407-457-4815)
1106 CHARMING ST, MAITLAND, FL 32751
$495,00020 Days on yellowkey MLS ID: TB8489671
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1870 Built: 2006Monthly Fee: $520 Tax: $6,232 (2025)Community: Enclave/Maitland A-FSpa: NoTownhouse
Taxes:$6,232
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to this beautiful Mediterranean-style townhome in the exclusive, gated community of Montacino in Maitland, Florida. Updated 3 bedroom, 2.5 bath home overlooking Lake Charity. Expansive views of the lake are seen from the front porch, two bedrooms and the dining room. Separate dining room with tons of natural light. Open concept kitchen with updated cabinets and stainless steel appliances. The large family room is open to the kitchen for ease of entertaining. Situated between the garage and your back door is an open air, private courtyard. Enjoy a two and a half car garage with full attic for additional storage. The second floor includes three bedrooms, finished laundry with closets that have been professionally customized. Secondary bedroom boasts a Murphy bed for guests with build-in storage. You will enjoy resort style living with the sparkling community pool and tranquil walks along the shores of Lake Charity. Extra guest parking is located just outside the garage. Internet/TV package and lawn care included. Located just 1/4 mile from I-4 and the Maitland Boulevard exchange with easy access to Winter Park, downtown Orlando and Altamonte Springs. Close by is Trelago Market where the new Trader Joes is being built. A must see property.
Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)
Listing Agent: Stephen Hachey (813-642-6030)
1732 RIDGEWOOD AVE #S, MAITLAND, FL 32751
$749,00072 Days on yellowkey MLS ID: O6378854
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2407 Built: 2016Monthly Fee: $425 Tax: $6,155 (2024)Community: Ridgewood Villas CondoTownhouse
Taxes:$6,155
Elementary School: Dommerich Elem
High School: Winter Park High
Remarks: This custom two-story townhome delivers what most properties in this category simply don’t; space, light, and a layout that actually makes sense. Open, airy, and thoughtfully designed, every detail feels intentional. Perfectly positioned between Maitland and Winter Park, you’re just minutes from Park Avenue, Winter Park Village, and some of the best dining and shopping in Central Florida. Step inside and you immediately notice how expansive it feels. Soaring ceilings and abundant natural light make the home live far larger than a typical townhome. The first floor flows seamlessly, creating a true open-concept environment ideal for entertaining or everyday living. The oversized island anchors the space, perfect for hosting friends, casual dinners, or setting up a productive work-from-home station. Upstairs is where this home truly stands apart. Three full bedrooms, each with its own ensuite bath, a rare and highly desirable feature. The primary suite offers a private retreat with a spacious layout, generous walk-in closet, dual vanities, and a large walk-in shower that feels straight out of a luxury spa. The secondary suites provide comfort and privacy rarely found in townhome living. Step outside and enjoy a private side yard, a perfect extension of your living space. Whether you’re grilling on the weekend, setting up a small outdoor lounge, or simply enjoying the Florida sunshine, this added outdoor area gives you the flexibility most townhomes don’t offer. A private side-entry two-car garage adds both security and convenience while preserving the home’s clean curb appeal. If you’ve been searching for something near Winter Park that offers style, functionality, and location without compromise, this one checks every box.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Brandon Geers (941-928-5152)
1010 WINDERLEY PL #127, MAITLAND, FL 32751
$339,00016 Days on yellowkey MLS ID: O6395028
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1563 Built: 1997Monthly Fee: $375 Tax: $4,625 (2025)Community: Villas Lake DestinyTownhouse
Taxes:$4,625
Middle School: Lockhart Middle
Remarks: Welcome to Villas of Lake Destiny, a gated lakefront community tucked quietly in the heart of Maitland, offering a rare blend of privacy, natural beauty, and unmatched convenience. Residents enjoy a serene, low-traffic setting surrounded by mature landscaping, water features, and direct access to Lake Destiny, including a private community boat ramp, lakefront pool, and tennis courts. Located just minutes from I-4, the Maitland Exchange (414), Maitland Center, RDV Sportsplex, shopping, dining, and major employers, this community delivers an ideal balance of lifestyle and accessibility. This beautifully updated townhome features a private 1-car garage with gated courtyard-style entry, creating both security and a welcoming first impression. Inside, soaring ceilings and a transom window over the sliding glass doors fill the home with natural light, leading to a private screened patio that extends your living space outdoors. The main level showcases all tile flooring, a spacious open-concept living and dining area, and a well-appointed kitchen designed for both function and style. Features include upgraded white shaker cabinets with crown accents, subway tile backsplash, an extra-large stainless steel basin sink, glass cooktop with microwave hood, french door refrigerator, and pendant lighting over the breakfast bar. Upstairs and down, the layout offers flexibility and privacy with three generously sized bedrooms, each with ceiling fans and ample closet space. The oversized primary suite is a true retreat with two closets, including a walk-in, and a large ensuite bath featuring dual vanities, a walk-in shower, and a full wall vanity mirror. Additional highlights include brand new carpet, a 30-year tile roof replaced in 2023, HVAC system installed in 2020, modern brushed nickel fixtures throughout, and a versatile 9x9 bonus room with indoor laundry and washer/dryer included. Whether you are looking for low-maintenance living, proximity to everything Central Florida has to offer, or a quiet lakefront community to call home, this property delivers on all fronts.
Listing is courtesy of: DON HARKINS REALTY LLC (321-377-0341)
Listing Agent: Donald Harkins, Iii (321-377-0341)
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