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$1,120,000
4 Beds ⋅ 3 Baths ⋅ Tanglewood Sec 3 Rep SubDv. ⋅ 32792 Zip Code
Experience the best of Winter Park living in this stunning new custom-built pool home situated on a generous .29-acre lot just 1.9 miles from Park Avenue. Designed with a modern aesthetic and built to the highest standards, this 4-bedroom, 3-bath residence is a true showcase of craftsmanship and luxury. Step inside to discover a stunning vaulted great room where the kitchen, living, and dining areas flow seamlessly together, all bathed in natural light from custom windows and expansive 16-foot sliding glass doors. An impressive open staircase leads to a soaring second floor, where you’ll find hardwood flooring, three spacious bedrooms, and a versatile game room or flex space. At the heart of the home is a chef-inspired kitchen featuring SMEG Italian appliances, custom cabinetry, and a breathtaking Taj Mahal quartzite waterfall island. The primary suite offers a peaceful retreat with a spacious 19x13 bedroom, a luxurious bath featuring a walk-in shower, soaking tub, and a custom dual-sink vanity. Throughout the home, you’ll find Pella windows, designer lighting, and thoughtful custom finishes. Step outside to your fully fenced backyard oasis complete with a large sparkling pool, perfect for relaxing or entertaining. This is a rare opportunity to own a distinctive, move-in-ready home in one of Central Florida’s most sought-after neighborhoods.

5236 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
$440,000
5 Beds ⋅ 2 Baths ⋅ Tanglewood Sec 3 Rep SubDv. ⋅ 32792 Zip Code
Spacious 5-Bedroom Pool Home in Winter Park – Over 2,200 Sq Ft, Prime Location Near Interlachen Country Club Welcome to 5073 Lake Howell Road, a rare opportunity to own a 5-bedroom, 3-bath pool home with over 2,200 square feet of living space, set on a generous lot in the heart of Winter Park. Surrounded by million-dollar new construction homes and located just minutes from Interlachen Country Club, this property offers both immediate comfort and long-term investment potential in one of Central Florida’s most desirable areas. This single-story residence features a flexible layout designed to meet a variety of needs. Inside you’ll find multiple living and dining areas, a spacious kitchen with solid cabinetry and ample storage, and generously sized bedrooms perfect for family, guests, or home office space. With a roof replaced in 2021, one of the largest expenses of homeownership has already been taken care of, providing peace of mind as you move in or plan future updates. The home’s versatile floor plan offers endless potential. Whether you’re looking to renovate and modernize, add luxury finishes, or design a fully customized Winter Park dream home, this property delivers the space and structure to bring your vision to life. Step outside and enjoy Florida living at its best. The screened-in pool and covered patio provide the perfect space for entertaining, relaxing, or soaking up the year-round sunshine. The fenced backyard adds privacy and flexibility for pets, gardening, or outdoor recreation. Location is everything, and this home delivers. You’ll be just a short drive to Winter Park’s Park Avenue with its boutique shops, fine dining, and cultural attractions, while also being close to the Winter Park YMCA, top-rated schools, and major roadways. Centrally positioned, you’ll have convenient access to Maitland, Casselberry, and Altamonte Springs, making this property a perfect hub for work, play, and everyday living. With its combination of size, pool, newer roof, and prime setting in a gentrifying neighborhood, 5073 Lake Howell Road is ideal for investors, renovators, or homeowners seeking a long-term opportunity with instant upside. Don’t miss this rare chance to secure one of Winter Park’s most versatile and well-located homes. Schedule your private showing today and see the full potential of this property firsthand.

5073 Lake Howell Road, Winter Park
$415,000
4 Beds ⋅ 2 Baths ⋅ Tanglewood Sec 3 Rep SubDv. ⋅ 32792 Zip Code
BACK ON THE MARKET AND PRICED BELOW MARKET IN DESIRABLE TANGLEWOOD WINTER PARK COMMUNITY WITH NO HOA! ALLOWS SHORT TERM RENTALS (STR). LOW TAX DISTRICT. This is probably the closet you can get to Winter Park (Park Ave) without having to pay the Winter Park taxes or conform to their restrictions! This property has been extremely well maintained and would be an amazing home for a new family. ROOF IS 2023! All systems have been updated or serviced. Property features include 4 BEDROOMS, 2 BATHROOMS, 1,725 TOTAL SQFT, ATTACHED IN-LAW SUITE WITH ITS' OWN ENTRY, HUGE BACK YARD WITH LOT SITTING ON APPROX. 10,000 SQFT, TILE THROUGHOUT, STAINLESS APPLIANCES INCLUDED, FENCED, AND MORE. Seller is willing to give $5,000 credit towards the buyer's closing costs or buying down their interest rate (inquire about conditions). *More than one of the photos has been virtually staged.

1816 Ivy Lane, Winter Park
$350,000
3 Beds ⋅ 2 Baths ⋅ Tanglewood Sec 3 Rep SubDv. ⋅ 32792 Zip Code
Welcome to this quaint 3 bedroom, 2 bath property in the heart of Winter Park. Bring your imagination and design for a home you'll love, because this block home is the perfect blank slate. The large, open living/dining combination is perfect for entertaining or multi-functional living spaces. Additionally, an oversized, screened back porch provides indoor-outdoor living opportunity to enjoy the large, serene backyard. This lot backs up to the Interlachen Country Club, which is landscaped for privacy so the new owners will enjoy their space without any rear neighbors. Each of the two secondary bedrooms are outfitted with custom built-ins, perfect for office space(s), but could also be transformed into functional bedrooms. There is original terrazzo in the home as well as recently updated (2021) luxury vinyl flooring in the kitchen and living spaces. New owners will appreciate additional updates such as a 2022 roof and 2023 HVAC. The kitchen was renovated with quartz countertops and new cabinetry in 2021. This home is zoned for Seminole County Public Schools, which is consistently rated as the top school district in all of Florida. Only 1 mile from the nearest Publix, 0.5 miles from the Winter Park YMCA, and 30 minutes from Orlando International Airport, this home is conveniently located to the best of Orange and Seminole County's shopping and dining.

5128 Lake Howell Road, Winter Park
$349,000
3 Beds ⋅ 2 Baths ⋅ Tanglewood Sec 3 Rep SubDv. ⋅ 32792 Zip Code
Charming single-family home offering exceptional value in today’s market! This inviting property features a functional kitchen with an oversized pantry and durable luxury vinyl plank flooring throughout for easy maintenance and modern appeal. French doors open to a very large fenced backyard, creating the perfect space for entertaining, pets, or play. Enjoy peaceful wooded views with a golf course behind the home — providing privacy with no rear neighbors and no future development directly behind you. The home offers 1.5 baths, including a convenient en-suite half bath in the primary bedroom. Major updates include a 2020 HVAC and 2021 roof for added peace of mind. Located just minutes from downtown Winter Park and situated in a highly regarded school district, this home presents a wonderful opportunity for buyers looking to get into the Winter Park area at an accessible price point.

5202 Lake Howell Road, Winter Park
$250,000
3 Beds ⋅ 2 Baths ⋅ Tanglewood Sec 3 Rep SubDv. ⋅ 32792 Zip Code
Located in the heart of Winter Park, this property is a prime candidate for redevelopment. Sitting on a ~9,259 sq ft lot, this is an ideal opportunity for builders or investors looking to capitalize on land value in a highly desirable area. The existing structure is a 3 bed, 1.5 bath home, but the true value here is in the lot and location. The seller has already cleared out the interior, making it easy to assess and move forward with your plans.

1823 Maywood Road, Winter Park
$158,775
3 Beds ⋅ 2 Baths ⋅ Tanglewood Sec 3 Rep SubDv. ⋅ 32792 Zip Code
This home is located in desirable Winter Park. Has loads of potential. Great location. House is solid and needs some work, but this offering is priced right and ready to go. Sold As-Is.

1823 Maywood Road, Winter Park