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1016 Howell Branch Road, Winter Park
$1,650,000
4 Beds ⋅ 3 Baths ⋅ Maitland Shores SubDv. ⋅ 32789 Zip Code
Canal Front Oasis on the Winter Park Chain of Lakes! (Seller Financing Available for Qualified Buyers) Welcome to 1016 Howell Branch Road, where every day feels like a getaway. This beautifully reimagined 4-bedroom, 3-bath residence offers 3,142 square feet of inspired living space set amid lush, tropical landscaping — all within the best of Winter Park and Maitland. *The canal allows for full Lake Maitland and Winter Park Chain of Lakes access by powerboat. (Current owners have a 19' outboard they use to pull tubes, ski, wakeboard, quick trips to dog island and entertaining via scenic tours through the Winter Park Chain of Lakes.) Originally built in 1959 and completely renovated in 2022, this two-story retreat combines rustic charm with modern luxury. Step inside to discover an open floor plan anchored by a gas fireplace, open kitchen and dining room, warm custom woodwork, and thoughtful built-ins throughout. The renovation includes new electrical, plumbing, new kitchen and baths, engineered hardwood flooring throughout, amongst many more upgrades. The redesigned layout adds over 1,000 square feet, featuring a spacious first-floor laundry room and an all-new second story with a luxurious primary suite, a guest bedroom (currently used as an office), and a full bathroom. Outdoors, enjoy a new boathouse on a canal and an inviting outdoor living area — perfect for entertaining or unwinding along the peaceful canal that connects directly to Lake Maitland and the renowned Winter Park Chain of Lakes. The rear of the property backs up to a wooded conservation area that provides privacy and tranquility. The current owner received a variance for a future pool, and Orange County previously had no objections to pool installation (new owner would need to reapply). The property sits in one of Central Florida’s most sought-after school zones: Dommerich Elementary, Maitland Middle, and Winter Park High. Families here often bike or walk to school. Enjoy regular walks through scenic streets lined with mature cypress trees, palms, vibrant native vegetation and beautiful homes that line Lake Maitland. With no HOA, residents may optionally join the neighborhood association (approx. $120/year) for access to two lakefront parks and a private boat ramp. From the modern amenities and artful landscaping to the serene waterfront setting, this is truly a one-of-a-kind property that blends nature, comfort, and sophistication in the heart of Winter Park. *Canal boat tour video that showcases the trip from the canal to Lake Maitland is available via the virtual tour link in the listing.

1016 Howell Branch Road, Winter Park

5233 Lake Howell Road, Winter Park
$760,000
4 Beds ⋅ 3 Baths ⋅ Tanglewood Sec 3 Rep SubDv. ⋅ 32792 Zip Code
Welcome to 5233 Lake Howell Road, a thoughtfully updated residence offering modern finishes, extensive upgrades, and a private backyard retreat designed for both everyday living and effortless entertaining. Inside, white porcelain tile flooring and recessed lighting create a bright, cohesive atmosphere throughout the main living spaces. Expansive rear-facing windows frame serene views of the beautifully landscaped backyard. The fully renovated kitchen is both stylish and functional, featuring new cabinetry, under-cabinet lighting, a built-in oven, cooktop, microwave drawer, and new sink. The open-concept layout flows seamlessly into the Florida room, where abundant natural light enhances the inviting ambiance. The living area is anchored by a resurfaced wood-burning fireplace, adding warmth and timeless character. The primary suite serves as a peaceful retreat, complete with a renovated bathroom, custom closet system, and a conveniently located in-suite laundry area with custom frosted glass doors and a new stackable washer and dryer. Two additional guest bathrooms have also been renovated, and custom closet systems extend throughout the home, including guest bedrooms and hallway storage. The backyard is a true oasis, highlighted by a newly resurfaced 16x32 pool and multiple spaces for al fresco dining, lounging, or gathering around the fire pit. The new paver patio offers the perfect spot to unwind with a good book. The fully fenced yard features refreshed landscaping with artificial turf, landscape lighting, and a new irrigation system serving both the front and rear yards. A custom greenhouse/workshop with a misting system adds a unique and functional outdoor element, while thoughtful drainage enhancements, including a French drain along the rear of the home and patio drainage to the front sidewalk, provide added peace of mind. Major improvements include a new roof (2023), water heater (2023), HVAC system and ductwork (2023), and a full plumbing update (2023). Additional features include a mini-split system, drip irrigation, updated electrical and LED lighting throughout, Pella double-paned windows, remote shades throughout, Leafguard gutters, expanded circular driveway, and added attic insulation. The home is also equipped with Google cameras and a doorbell at both front and rear entrances, as well as pre-wiring for a pool heater. This move-in-ready home seamlessly blends modern comfort with thoughtful upgrades, all set in a desirable Winter Park location just minutes from the YMCA, Interlachen Country Club, Phelps Park, Park Avenue, and a variety of dining destinations.

5233 Lake Howell Road, Winter Park

151 Lewfield Circle Unit 4, Winter Park
$130,000
1 Beds ⋅ 1 Baths ⋅ Stratford A Winter Park Condo SubDv. ⋅ 32792 Zip Code
Enjoy Winter Park lifestyle in this great, first floor, 1 bedroom 1 bath condo. Built in 1973 with a well-planned 678 sq.ft. floor plan. Featuring Laminate flooring, this condo offers a functional and inviting home. The kitchen comes equipped with a range, refrigerator, dishwasher and microwave. The oversized bedroom comes with stackable washer an dryer and two closets. New bedroom window, new sliding glass door, new bathroom vanity. Updated wiring and electrical panel. Enjoy all your community amenities including a two pools, tennis courts, clubhouse and 24/7 fitness center. The HOA covers water, trash removal, Internet, common area pest control, grounds maintenance, and exterior maintenance while the pool is maintained for your enjoyment. A convenient on-site laundry room features two washers and two dryers free of charge, and the clubhouse is available for rental for gatherings or events. Situated in a prime Winter Park location, this condo is close to grocery stores, shopping centers, and major routes like the 408, Semoran Blvd and St. Rd. 50 for quick access across the area. This condo is just 20 minutes from UCF, 10 minutes from Full Sail, Rollins College, and the vibrant Park Avenue in Winter Park. Quick access to major highways (417 and I-4), everything you need is within reach. Welcome Home!

151 Lewfield Circle Unit 4, Winter Park

736 Warrenton Road, Winter Park
$310,000
2 Beds ⋅ 2 Baths ⋅ Winter Park Pines Patio Homes SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Renovated 2 bedroom, 2 bathroom villa in a prime Winter Park location, ready for its next owner. Walk into a spacious, light and bright foyer with fresh interior paint and sliding doors that lead out to the patio, bringing in tons of natural light. The seller has removed all popcorn ceilings (a huge upgrade), and the property features laminate flooring throughout most of the main living areas. The main living space has vaulted ceilings and an open layout with room for both living and dining, and sliding glass doors leading out to the patio. The kitchen has been updated with new stainless steel appliances and new countertops, and offers a closet pantry along with a bay window that brightens the space. The primary suite is set toward the back of the home with high ceilings, its own sliding doors to the patio, a walk-in closet, and a renovated bathroom with a large walk-in shower. The split floor plan places the second bedroom near the front by the foyer, with a renovated full bathroom just next to it—great for guests or a home office. The backyard offers a blank canvas to create your own oasis, with a covered patio, a large screened porch, and a fully fenced private yard—hard to find with a villa! Additional highlights include a one-car garage with washer/dryer hookup, new light fixtures, and fresh interior paint. Located in the Winter Park Pines just minutes from iconic Park Avenue shopping and dining and downtown Winter Park. Across from Full Sail and a short drive to UCF. Call today to schedule your private showing!

736 Warrenton Road, Winter Park

1680 Palmer Avenue, Winter Park
$795,000
3 Beds ⋅ 2 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code
This 1-story home on a corner lot offers easy living in one of Winter Park’s most convenient locations! Enter through a covered front porch and inviting foyer with slate tile floors to discover a desirable split-bedroom floorplan. Off to the right, the spacious primary wing (later addition) serves as a true retreat, with vaulted ceilings, hand-carved wood floors, a cozy window seat wrapped in a bay window, and French doors that lead to the private outdoor living spaces. The large primary bath has dual vanities, a soaking tub, huge walk-in shower, and a custom walk-in closet....This primary retreat is a HUGE surprise! On the opposite side of the front entrance, the home’s original, refinished hardwood floors stretch throughout the living room, kitchen, and large secondary bedrooms. The kitchen features stainless steel appliances, a wine refrigerator, and a dinette area with a precious greenhouse window, perfect for growing fresh herbs and potted plants. The kitchen/dinette area open up to the window-lined living room, with plantation shutters. French doors off the adjacent dining room lead to a newly PVC-fenced rear courtyard with brick pavers and a soothing fountain. The left side of the property includes a screened patio with terracotta tile and a vaulted, wood-plank ceiling, while the right side offers a fully-fenced space for pets, gardening, or play. Enjoy an impeccably landscaped yard with Zoysia grass and a private well for irrigation, plus an enormous 2-car garage that was thoughtfully added on, with a large, sunny laundry area with a double utility sink, and plenty of room for storage or a workbench area. Block construction and updated double-pane windows & doors make the home remarkably quiet inside, and the circular front drive and expanded driveway makes life on Palmer a breeze! Just across the street, Phelps Park provides a playground, tennis, pickleball courts, and additional parking for your larger gatherings. Located just a block from the YMCA, minutes from Publix, Sprouts, Walgreens, and numerous restaurants, and less than 2 miles from Park Avenue, this home is where convenience meets comfort.

1680 Palmer Avenue, Winter Park

535 N Interlachen Avenue Unit 203, Winter Park
$550,000
2 Beds ⋅ 2 Baths ⋅ Andalucia Apts SubDv. ⋅ 32789 Zip Code
Experience effortless luxury living just blocks from iconic Park Avenue in this stunning, fully renovated condo located in the heart of downtown Winter Park. Perfectly designed for a lock-and-leave lifestyle, this beautifully upgraded residence blends timeless elegance with modern convenience. Step into a beautifully designed foyer entry that opens to bright, open living spaces with treetop views from the screened lanai. Every inch of this home has been thoughtfully updated—featuring crown molding, designer light fixtures, removal of popcorn ceilings, updated wiring, and plantation shutters throughout. Major systems are also newer, with an HVAC system and water heater (2020) for peace of mind. Gourmet kitchen is appointed with quartz countertops, white shaker cabinets, stainless steel appliances, dramatic backsplash and under cabinet lighting. Custom built-ins in dining area for additional storage. Large Owner’s Suite offers two custom closets with built-in organizers and spa like bath with walk in shower. Spacious secondary bedroom. Renovated guest bath with modern finishes. Andalucia is a boutique community with just 20 owner-occupied units—no rentals, no pets—ensuring a peaceful, neighborly environment. Additional highlights of this condo include a private storage closet, one covered parking space + guest parking, elevator, well landscaped courtyard and patio, community laundry room, cable and internet. Walk to Park Avenue’s shops, restaurants, museums, and the Winter Park Golf Course, Morse Museum of Art, Central Park, Farmer’s Market and SunRail station. Enjoy vibrant culture and charming streets just steps from your door. This move-in ready condo offers the best of upscale Winter Park living—schedule your private tour today!

535 N Interlachen Avenue Unit 203, Winter Park

887 Georgia Avenue, Winter Park
$4,500,000
6 Beds ⋅ 6 Baths ⋅ Dyer Susan Resub SubDv. ⋅ 32789 Zip Code
Offered for the first time in over 50 years, this distinguished Winter Park estate is a true traditional gem, nestled on a picturesque brick street and situated on a full 1-acre lot. Exuding timeless charm with a subtle New England ambiance, this residence represents the best of historic Winter Park living—all within walking distance to Park Avenue. This stately 6-bedroom, 5.5-bathroom home offers 5,759 square feet of thoughtfully designed living space, plus an additional 1,859-square-foot unfinished basement that spans the entire length of the home, offering endless possibilities for expansion or customization. Upon entry, you'll be welcomed by coffered ceilings in the spacious formal living room, rich dark oak floors, and one of the home’s three gas fireplaces. This elegant yet inviting room overlooks the lush gardens, making it an ideal setting for both entertaining and quiet relaxation. Adjacent to the living room is a cozy, beautifully appointed den featuring another gas fireplace and natural jute flooring—undoubtedly one of the most beloved spaces in the home. The kitchen is filled with natural light and includes a large casual dining area, a charming butler’s pantry, and direct access to both the laundry room—complete with a full-size refrigerator and half-bath—and the oversized 2-car garage. The formal dining room showcases lattice-framed bay windows with views of the back garden and pool area, creating a warm and elegant space perfect for holiday dinners and family gatherings. The home features two primary bedroom suites on the main level, including one expansive L-shaped suite with its own gas fireplace and views of the pool, gardens, and outdoor terrace. The primary bathroom includes a dressing area and marble finishes throughout. Upstairs, the south wing includes two generous bedrooms with a shared full bathroom, while the north wing—located above the kitchen—offers two additional bedrooms and a charming full bath. The expansive backyard is a private sanctuary, framed by majestic oak trees, bamboo, and thoughtfully designed gardens, with several inviting sitting areas for outdoor relaxation. An extra-large swimming pool completes the setting—perfect for warm Florida days or evening gatherings under the stars.

887 Georgia Avenue, Winter Park

525 Lakeview Avenue, Winter Park
$1,390,000
4 Beds ⋅ 5 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code
Under Construction. Renderings available soon. Brand-new custom construction on coveted Lakeview Avenue marries classic Winter Park charm with crisp, contemporary living. Behind its inviting façade you’ll find an airy two-story layout featuring four bedrooms and 4 ½ baths, including a full en-suite guest retreat on the main level. Three additional bedrooms share the upper floor with a bright loft that easily flexes as a playroom, office, or second lounge.The heart of the home is a chef-ready kitchen outfitted for serious cooking—double wall ovens, a dedicated cooktop, and generous countertop space—anchored by a spacious walk-in pantry and a convenient mudroom drop zone to keep daily life organized. Just beyond, a soaring great room centers on a built-in fireplace, while wide sliders open to a covered rear porch perfect for year-round alfresco dining. Upstairs, every bedroom enjoys direct or semi-private bath access, giving the residence the feel of four private suites, and a dedicated laundry room means no hauling baskets downstairs. Practical perks abound: an oversized two-car garage for gear and golf carts, impact-rated construction engineered to the latest Florida wind code, and full pre-wire rough-ins ready for your preferred appliance and lighting packages. All this sits minutes from Park Avenue’s dining and boutique shopping, Rollins College, and Winter Park’s famous chain of lakes. Schedule your private tour and discover the fresh, low-maintenance lifestyle waiting for you in one of Central Florida’s most sought-after neighborhoods. Final design and features subject to change.

525 Lakeview Avenue, Winter Park

737 N Capen Avenue, Winter Park
$800,000
3 Beds ⋅ 2 Baths ⋅ Capens Add SubDv. ⋅ 32789 Zip Code
Welcome to this stunning Mid-century style 3 bedroom, 2 bath, 1930 sq ft home with a 2 car garage, where sleek modern design meets functionality. Step into the open-concept living space and be captivated by the abundance of natural light streaming through the large windows, creating a warm and inviting atmosphere. The centerpiece of this home is the gourmet kitchen, featuring top-of-the-line appliances that are sure to impress any culinary enthusiast. The Samsung Fridge and new natural gas range are equipped with cutting-edge technology, including the ability to air fry, dehydrate, and even bread proof. The kitchen also boasts stylish two-tone cabinets with a 42" upper configuration. Prepare meals with ease using the convenient split oven, perfect for hosting and baking multiple dishes simultaneously. The oversized island, measuring an impressive 8'x4', offers a spacious area for meal preparation, dining, or casual gatherings. Wood beams on the ceiling in the open area add a touch of rustic charm to the modern aesthetic. The mature landscaping surrounding the property provides a serene and private outdoor oasis, perfect for relaxing. Enjoy the convenience of having the laundry facilities conveniently located inside the home. Additionally, the remote blinds in the public areas allow for easy light control and privacy adjustments at the touch of a button. Arlo security system included. This home is located in beautiful Winter Park, near Park Ave, with restaurants, shopping, Rollins College, and events close by. Also enjoy Winter Park's convenient transportation via the Sunrail to downtown or Amtrack throughout FL. Call today for a private tour! Room Feature: Linen Closet In Bath (Primary Bedroom).

737 N Capen Avenue, Winter Park

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