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1357 Benevolent Street, Maitland
$425,000
3 Beds ⋅ 3 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code
Mediterranean-Inspired Living in the Gated Community of Montalcino! Welcome to this beautifully maintained townhome in the sought-after gated community of Montalcino/Enclave, ideally located just off I-4 in Maitland. Fresh, neutral interior and exterior paint make this home truly move-in ready, while its pristine condition reflects the care of its original owner. Offering three bedrooms, two and a half baths, and a thoughtfully designed two-story floor plan, this low-maintenance home perfectly blends comfort, style, and convenience. HOA BONUS! Monthly dues include high-speed internet, WiFi, and expanded television/streaming services! The first floor features elegant tile flooring throughout the kitchen, dinette, and living areas, along with a convenient half bath near the entry. The open-concept design creates an inviting atmosphere for everyday living and entertaining, with generous storage, including a spacious under-stair storage area. The living room is also wired for surround sound. The well-appointed kitchen showcases 42-inch solid wood cabinetry, under-cabinet lighting, a newly installed tile backsplash, granite countertops, a closet pantry, and a breakfast bar overlooking the family room and dinette. Just off the living area, a covered, screened lanai provides the perfect spot to unwind and enjoy the outdoors. Upstairs, you'll appreciate stylish luxury vinyl plank flooring throughout—NO CARPET! The spacious primary suite features a private balcony, a large walk-in closet, and an ensuite bath with dual sinks and a separate shower. Two additional bedrooms, a full hall bath, and a conveniently located laundry closet complete the second floor. Additional features include an upgraded two-zone HVAC system (2021), five-inch baseboards, six-panel interior doors, decorative wrought-iron stair railings, a wired security system, an in-wall pest defense system, and a paver driveway. Residents of Montalcino enjoy wonderful resort-style amenities, including a sparkling community pool and cabana overlooking private Lake Charity. Conveniently located with easy access to I-4, Downtown Orlando, Winter Park, shopping, dining, area attractions, theme parks, and Florida's beautiful beaches, this home offers an exceptional opportunity to enjoy maintenance-friendly living in a desirable gated community. Come experience the comfort, convenience, and lifestyle that make Montalcino such a wonderful place to call home!

1357 Benevolent Street, Maitland

2365 Sierra Lane Unit 2365, Maitland
$339,500
2 Beds ⋅ 3 Baths ⋅ Sierra Condo Ph 1 SubDv. ⋅ 32751 Zip Code
Hidden Gem! This small community is quiet, independent, extremely well maintained and one of Maitland's most desirable communities. This unit is a spacious with two bedroom suites each with its own connected bathroom and an additional 1/2 bath four guest. Home is arranged with a separate dining room or office space, living room, kitchen and breakfast room. The kitchen is fully equipped with all appliances. There's also plenty of room with the breakfast nook which looks out onto the pool and tennis courts. A wood-burning fireplace creates a warm, welcoming atmosphere that links the living room, kitchen, and dining room. An additional Florida room adds a great peaceful reading room. All the of the main rooms have tall ceiling which provide open feel and lots of natural lite from the upper windows. Bedrooms are spilt plan, main bedroom is on ground floor with 10 ft ceiling. Great location.. this lot, offers a generous outdoor area where you can relax and take in the lush landscaping front and back The attached private one-car garage provides ample storage space, with easy access to the washer and dryer for added convenience. Home offers gas water heater and gas heater. Community offers amenities including the pool and tennis courts, enhancing your lifestyle. Sellers offer possible concessions for loan buy-down or closing costs. See today! Seller offering possible concessions for closing costs and/or interest rate buy downs,

2365 Sierra Lane Unit 2365, Maitland

2312 Sierra Lane Unit 2312, Maitland
$349,600
2 Beds ⋅ 3 Baths ⋅ Sierra Condo Ph 1 SubDv. ⋅ 32751 Zip Code
Hidden Gem! This small community is quiet, independent, extremely well maintained and one of Maitland's most desirable communities. This unit is a spacious with two bedroom suites each with its own connected bathroom and an additional 1/2 bath four guest. Home is arranged with a separate dining room or office space, living room, kitchen and breakfast room. The kitchen is fully equipped with all appliances including a gas stove. There's also plenty of room with the breakfast nook which looks out onto the wooded back area. A wood-burning fireplace creates a warm, welcoming atmosphere that links the living room, kitchen, and dining room. An additional Florida room adds a great peaceful reading room .All the of the main rooms have tall ceiling which provide open feel and lots of natural lite from the upper windows. Bedrooms are spilt plan, main bedroom is on ground floor with 10 ft ceiling. Great location.. this lot, offers a generous outdoor area where you can relax and take in the lush landscaping front and back The attached private one-car garage provides ample storage space, with easy access to the washer and dryer for added convenience. Home offers gas stove, gas water heater and gas heater. Community offers amenities including the pool and tennis courts, enhancing your lifestyle. Sellers offer possible concessions for loan buy-down or closing costs. See today! New plumbing re-piped 2018, new roof 2018 new windows 2023, new Ac 2024 Cable and WIF provided by HOA.

2312 Sierra Lane Unit 2312, Maitland

2050 Thunderbird Trail, Maitland
$749,000
4 Beds ⋅ 3 Baths ⋅ Highland Park Estates SubDv. ⋅ 32751 Zip Code
Timeless Florida Charm in the Heart of Dommerich this classic ranch is ideally situated in Maitland's highly sought-after neighborhood. Combining the character of an established home with thoughtful updates and room to make it your own, this property offers an exceptional opportunity in a location that continues to be in high demand. The renovated kitchen provides a fresh, inviting space for everyday living, while improvements including a roof (2018), windows (2019), A/C (2020), and water heater (2020) add to the home's appeal. A spacious addition with vaulted ceilings and a fourth bedroom featuring a private ensuite bath creates a desirable split-bedroom floor plan, offering flexibility and privacy for family and guests. Situated on a generous 9,600-square-foot lot, the property offers plenty of room to bring your vision to life. Whether that includes a resort-style pool and cabana, an expanded primary suite, or a beautifully designed outdoor entertaining area, there is exciting potential to create a home tailored to your lifestyle. Zoned for Dommerich Elementary, Maitland Middle, and Winter Park High School, this home is ideally positioned to enjoy the lifestyle that makes Maitland so desirable. Spend your Sunday mornings exploring the Maitland Farmers' Market and enjoy the charm, local shops, dining, and sense of community that define this established neighborhood. With its timeless Florida appeal, generous lot, and possibilities for the future, this is a wonderful opportunity to put down roots in Dommerich and make it your own.

2050 Thunderbird Trail, Maitland

1010 Winderley Place Unit 100, Maitland
$349,000
2 Beds ⋅ 3 Baths ⋅ Villas Lake Destiny SubDv. ⋅ 32751 Zip Code
Discover the best of Maitland living in this light and bright end-unit townhome in the gated, lakefront community of Lake Destiny. Offering 2 bedrooms, 2.5 bathrooms, and 1,640 square feet, this inviting home features vaulted ceilings, a versatile loft perfect for a home office, media room, or additional living space, and plenty of valuable upgrades. The updated kitchen showcases crisp white cabinetry and contemporary quartz countertops as well as a dining area for special gatherings. Low-maintenance ceramic tile and laminate flooring flow throughout the first floor, drawing you into the two-story living room. This space is enhanced with transom windows, adding even more natural light creating an airy feel. Upstairs, the loft and two spacious bedrooms offer comfortable retreats, with brand-new carpet adding a fresh touch. The primary features a walk-in closet and plenty of storage in the ensuite bathroom. You also have a beautiful water view further adding to the tranquilty of the space. For added convenience, there’s an interior laundry room and a one-car garage. Step outside and take in the serene water feature view from your private patio or walk over to the community pool for a relaxing afternoon soaking up the sunshine. When you’re heading off to work or play, I-4 and 414 are just minutes away and one of Orlando’s most popular fitness facilities, Genesis Health Club, is just 1.5 miles away. Costco, Target, Home Depot, along with a variety of shopping and dining options are a short 10 minute drive and Winter Park and downtown Orlando are less than 20 minutes from the home as well. Recent improvements include new upstairs carpeting, a Kinetico whole-home water softener and filtration system with reverse osmosis filtration at the kitchen sink, a roof replaced in 2023, a 2020 water heater, and an AC system updated in 2018/2019. **The home is available to be sold unfurnished or fully furnished for a complete turnkey experience!**

1010 Winderley Place Unit 100, Maitland

856 Park Lake Circle Unit 51, Maitland
$228,000
2 Beds ⋅ 2 Baths ⋅ Park Lake Twnhs SubDv. ⋅ 32751 Zip Code
FIRST 6 MONTHS OF HOA PAYMENTS COVERED BY SELLER! The Park Lake Townhome Community is Maitland's hidden treasure! Offering for sale this extremely well-maintained townhome with 2 levels of comfortable living, a one-car garage, a generously sized laundry room under air, along with a lovely private screened back patio. As you step inside, look over your shoulder at the community pool that is literally steps from your front door! Once inside you will immediately fall in love with the wood-look easy care tile throughout the first floor. The large living room has the cutest window seat, streaming in tons of natural sunlight, with room for many different seating configurations. A convenient half bath to your left leads you into the kitchen and dining areas of the home. The large open concept kitchen features new appliances and shiny granite countertops with plenty of counterspace for the chef in the family. Off the dining area you'll find a set of sliding glass doors leading out to a private screened-in patio, perfect for morning coffees, grilling or entertaining friends and family. The patio also provides access to the attached one-car garage with garage door opener. This garage leads into the oversized indoor laundry room complete with a washer and dryer and a large storage area. As we head up the stairs, you'll notice the brand-new carpet in a lovely neutral color running on the stair treads and into the first bedroom for comfort and style. The 2nd bedroom features the wood-look flooring for added convenience. Both bedrooms share a well-appointed en-suite bathroom with a newly reglazed tub and shower. Freshly painted inside makes this home truly turn-key, either as a residence or as an investment. Residents of the Park Lake Townhome Community not only enjoy the sparkling community pool, but your HOA also covers trash collection, exterior maintenance (including the roof!) and lawn care! BONUS, there is a dock on the lake accessible by the community (think about walks to the lake in the mornings to watch the sunrise with your coffee or in the evenings to watch the sunset with your glass of wine!). Low Maintenance Living at its Best! And have I mentioned this AMAZING LOCATION? This lovely townhome community is less than 1 mile from N Park Avenue and less than 1/2 mile to 17/92 (Orlando Avenue)! The convenience to Maitland City Center, Rollins College, shops, restaurants, and the ease of commuting to work is 2nd to none. Make an appt to see this home, it is a gem! Note, some photos have been virtually staged for furniture placement.

856 Park Lake Circle Unit 51, Maitland

895 Park Lake Circle Unit 75, Maitland
$174,900
2 Beds ⋅ 2 Baths ⋅ Park Lake Twnhs SubDv. ⋅ 32751 Zip Code
Look at that NEW Price! You decide to move in Now and upgrade as you go, benefitting from this below market price point, or Fix it up as little or as much as you want and keep the added Equity. 2 Bedroom, 1.5 Bath Townhouse with Living and Dining Rooms, Single Car Garage, Inside Laundry Room, and Oversized Fenced Patio. Located between 17-92 & I-4 with short commute to Winter Park, Downtown Orlando, or Maitland Center. Community Features include Swimming Pool less than 50 yards from Unit as well as Dock on Lake in Community. All Appliances in Unit. All Electrical Panels replaced July 2026, Alumicons to satisfy insurance for aluminum wiring added July 2026, Air Conditioning Replaced in 2016, Hot Water Heater in 2018, Garage Door in 2021. Sold As Is, Priced based on current condition.

895 Park Lake Circle Unit 75, Maitland

812 Park Lake Circle Unit 7, Maitland
$299,000
3 Beds ⋅ 3 Baths ⋅ Park Lake Twnhs SubDv. ⋅ 32751 Zip Code
Virtually Staged. Back to market due to lack of financing! Welcome to this beautifully updated two-story townhouse in the heart of Maitland, offering a well arranged floor plan, stylish finishes, and exceptional functionality. Featuring three bedrooms and two and a half bathrooms, the thoughtfully designed layout separates the living room from the kitchen and dining area, creating distinct yet connected spaces that feel open, organized, and highly functional. Walk into the fully renovated kitchen, showcasing elegant Calacatta quartz countertops, updated cabinetry, stainless steel appliances, and modern finishes that make it the centerpiece of the home. Waterproof luxury vinyl plank (LVP) flooring extends throughout the entire residence, complemented by updated lighting and fixtures that give the home a fresh, contemporary feel. Upstairs, the spacious primary suite offers a generous walk-in closet and private access to a screened balcony—the perfect place to enjoy your morning coffee or unwind in the evening. Step outside to your private courtyard, an inviting outdoor retreat perfect for relaxing or entertaining. Residents also enjoy access to a sparkling community pool, perfect for cooling off during Florida's warm summer months. Ideally situated with quick access to I-4 and Orange Avenue, this home places you just minutes from Downtown Orlando, top-rated hospitals, shopping, dining, and entertainment. Nearby attractions such as the Orlando Science Center and Orlando Museum of Art provide endless opportunities for culture and recreation, while schools and everyday conveniences are all within easy reach. With tasteful updates throughout, modern finishes, and an unbeatable Maitland location, this move-in-ready townhouse offers the perfect combination of style, comfort, and convenience. Schedule your private showing today!

812 Park Lake Circle Unit 7, Maitland

916 Park Lake Circle Unit 34, Maitland
$235,000
3 Beds ⋅ 3 Baths ⋅ Park Lake Twnhs SubDv. ⋅ 32751 Zip Code
**Listing price is seller's bottom line, he won't accept anything lower than asking** Gorgeous 3-bedroom, 3-bath, two-story townhome available now! This move-in-ready home features an updated kitchen with all appliances included, a convenient mudroom with washer and dryer hookups, fresh interior paint, and luxury vinyl plank (LVP) flooring throughout. Each spacious bedroom offers its own private bathroom and walk-in closet, providing comfort and privacy for everyone. It offers a 1-car garage and private courtyard, with plenty of guest parking. Enjoy maintenance-free living with the HOA handling exterior maintenance and lawn care. Conveniently located near I-4, shopping, dining, and everyday amenities, this property is ideal as a primary residence, investment property, or family home. Schedule your private showing today!

916 Park Lake Circle Unit 34, Maitland

814 Park Lake Circle Unit 8, Maitland
$211,000
2 Beds ⋅ 2 Baths ⋅ Park Lake Twnhs SubDv. ⋅ 32751 Zip Code
A beautiful affordable condo in Maitland. 2 bedrooms and 1 ½ baths with a 1 car garage. The kitchen has been updated with white cabinets and new counter tops. The appliances have been updated. There is a large dining room and separate living room. The utility room is on the 1st floor with an updated barn door for access. The 1st floor has wood flooring while the second floor has carpeting. The second floor has two bedrooms with an updated bathroom. The shower has been remodeled to allow easy access. This home has a large patio with artificial grass flooring. The one car garage is an added bonus. The property has had the window replaced, a new water heater (2026) and the electrical panel upgraded within the past couple of years. The A/C system was replaced in 2022. This wonderful unit is at a great price and will not last long.

814 Park Lake Circle Unit 8, Maitland

1994 Kenaston Road Unit 1994, Maitland
$389,000
3 Beds ⋅ 4 Baths ⋅ Ultra Vista Condo SubDv. ⋅ 32751 Zip Code
Located in the desirable city of Maitland, just three miles from Winter Park’s renowned Park Avenue, this extensively updated 3-bedroom, 3.5-bath townhouse offers modern living in a prime Central Florida location. Tucked within a quiet residential setting and zoned for highly rated Seminole County schools, the home provides easy access to dining, shopping, and entertainment while maintaining a sense of privacy and comfort. The thoughtfully designed layout offers flexibility and convenience across two levels. The main floor features a spacious primary bedroom complete with a walk-in closet and private bathroom. Also on the first level is a welcoming living area with vaulted ceilings, creating an open and airy feel, along with a dining space that looks out through French doors. The kitchen is well-appointed with stainless steel appliances, stone countertops, and ample workspace, making it ideal for everyday living and entertaining. A screened rear porch extends the living space outdoors, perfect for relaxing or enjoying Florida evenings. Upstairs, you’ll find a second primary bedroom with an attached bathroom, offering a private retreat for guests or multi-generational living. A third bedroom, also with its own bathroom, is located just off a landing that overlooks the living area below, adding architectural interest and an open-concept feel. Significant updates completed in 2024 enhance both comfort and long-term value, including a new roof, upgraded air conditioning system with a 10-year manufacturer warranty, fully updated plumbing, and modern electrical improvements with new breaker boxes, switches, and receptacles. Interior finishes include wood flooring on the main level, luxury vinyl plank flooring upstairs, tile in wet areas, energy-efficient Low-E double-pane windows, recessed LED lighting throughout, and updated fixtures in the kitchen and closets. The exterior was freshly painted in 2025, adding to the home’s curb appeal and move-in-ready condition. With its low-maintenance design, versatile floor plan, and unbeatable location near Winter Park’s Park Avenue and the scenic Chain of Lakes, this home presents

1994 Kenaston Road Unit 1994, Maitland

1033 Hamlet Drive, Maitland
$340,000
3 Beds ⋅ 2 Baths ⋅ Hamlet At Maitland SubDv. ⋅ 32751 Zip Code
This charming 3-bedroom, 2-bathroom single-family home with the best of Florida living. Located in the north of Orlando (Maitland - Winter Park area). 1.3 miles to the Center of Winter Park Shopping Plaza (Office Depot, UPS, Ross, Marshalls, Home Goods, Five Below, LA Fitness, Petco and Michaels, Whole Foods Markets, and Banking). Access to major highways, minutes to downtown, and Orlando's world-renowned theme parks. This 1,146 square foot home features an open-concept floor plan. Primary suite includes a walk-in closet and a private suite bathroom, plus two additional bedrooms that provide flexibility for guests, family or a home office. 1 car garage with a large driveway that accommodates 2 more cars. The property's best feature is solar panels owned outright! With an average monthly bill of $35.00!!! Don't miss your chance to make it yours - schedule a private showing today!

1033 Hamlet Drive, Maitland

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