Winter Park Homes with Street Lights Community Features

Winter Park Homes with Street Lights Community Features

Welcome to Winter Park, Florida—a charming city that perfectly blends the warmth of Southern hospitality with the sophistication of upscale living. Nestled just north of Orlando, Winter Park is renowned for its picturesque landscapes, vibrant arts scene, and a rich history dating back to the late 1800s. Stroll along the tree-lined streets, where you’ll find an array of boutique shops, delightful eateries, and cultural gems like the Charles Hosmer Morse Museum of American Art, home to an impressive collection of Tiffany glass.

One of Winter Park’s standout features is its commitment to creating a welcoming and safe environment for families and residents alike. The community of Homes with Street Lights exemplifies this ideal. Here, you’ll find beautifully designed homes that are not only aesthetically pleasing but also offer the comfort of well-lit streets, ensuring peace of mind for evening strolls and outdoor gatherings. The presence of street lights enhances the neighborhood’s charm, making it a perfect place for families to flourish and children to play freely.

With a close-knit community feel, residents enjoy a variety of amenities, including parks, recreational facilities, and community events that foster connection and camaraderie. Whether you're sipping coffee at a local café or enjoying a leisurely afternoon at the scenic Central Park, Winter Park embodies a lifestyle of relaxation and elegance.

Discover the enchantment of Winter Park and explore the Homes with Street Lights community—where your dream home awaits in a city that feels like a warm embrace. Your next chapter begins here!

Newest Winter Park Homes with Street Lights Community Features

$424,900
3 Beds ⋅ 3 Baths ⋅ Enclave At Hawks Crest SubDv. ⋅ 32792 Zip Code
Hawk's Crest is a care free resort style master planned community in Winter Park, Florida. With it's Modern style architecture, this 3 bedroom, 2 1/2 bathroom townhome is meticulously maintained with an HOA that covers more than most. While driving through the community you will pass the community pool and recreation area which is conveniently nestled at the end of Bantam Way. The curb appeal of the paver driveway and home design will make you feel you are home. Inside you will be greeted by a foyer before entering the home itself. On the main floor you will find a half bathroom/ guest bathroom, tile flooring throughout, excellent natural light, living room, dinette, and the statement kitchen sure to please. The kitchen boast granite counter tops, shaker style cabinets, a extra large kitchen island with a breakfast bar, ample size walk-in pantry, refrigerator 2026, all other appliances 2021, new and upgraded kitchen hardware, newer faucet, and newer large single basin sink. Upstairs you will find all the bedrooms, inside laundry room and both full bathrooms, The primary suite is an ample 20 x 15 with trey ceiling, en-suite bathroom, and walk in closet with a custom closet organizer. The en-suite bathroom is highlighted by a dual vanity sink, granite countertops, shaker style cabinets, and shower stall. Both additional bedrooms are an impressive 15 x 12 with walk in closets. The inside laundry room has upgraded cabinets. Out back you will find a quiet covered rear patio with space for seating, a grill, and more. Other highlights to mention include the tesla electric charger in the garage and freshly added cabinets and granite countertops in the drop zone just off the inside garage entrance. Community common areas include a resort style pool with covered social gathering area and a community playground. The HOA covers the cable, internet, community pool, exterior building maintenance, common area maintenance and more. Hawk's Crest is just minutes to Park Avenue Winter Park, 417, UCF, shopping, restaurants and much more. Just a short walk to the out-parcel building in the front of the community you will find local favorites like Foxtail coffee, Kelly's Ice cream, and the Park Maitland School. Don't miss this opportunity. These townhomes go quickly.

1521 Bantam Way, Winter Park
$425,000
3 Beds ⋅ 3 Baths ⋅ Enclave At Hawks Crest SubDv. ⋅ 32792 Zip Code
Welcome to the Enclave at Hawks Crest, where this modern 3-bedroom, 2.5-bath townhome gives you 1,755 square feet of space without a long list of things to maintain. A paver driveway, two-car garage, and clean exterior make a great first impression, and inside, high ceilings and plenty of natural light keep the main level feeling open and bright. The kitchen sits right in the middle of it all with a large island, stainless steel appliances, and a walk-in pantry, opening naturally to the dining and living areas. Out back, sliding doors lead to a covered, screened patio overlooking greenspace, giving you a little breathing room without a backyard to take care of. Upstairs, the primary suite is spacious with a tray ceiling, large walk-in closet, and ensuite bath with dual sinks and a tiled shower. Two additional bedrooms sit at the opposite end of the hall, along with a second full bath and, thankfully, the laundry room is upstairs too. This home has been meticulously maintained by its original owner since 2021. The HOA handles the exterior and landscaping, and the gated community includes a resort-style pool, playground, and dog park. Zoned for A-rated Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High, and you're just minutes from Park Avenue, with Kelly's Ice Cream and Foxtail Coffee a short walk from your front door. Low maintenance, high convenience, and Winter Park right outside your door. Call today for your private showing!

2349 Shadowland Loop, Winter Park
$130,000
1 Beds ⋅ 1 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code
It doesn't get much better than this: Living in a Lakefront and Winter Park community, that is convenient to I-4 providing easy access to points north and south, downtown Winter Park, shopping, fine dining, and the price can't be beat. The HOA dues includes water, trash pickup, a full package from Spectrum including internet. Lakeside Manor is situated on the north side of Lake Killarney, a 239 acre lake that is perfect for sailing, motor boating and skiing. The lush courtyard, lakeside pool, clubhouse and gazebo, updated dock and private boat ramp make this a serene place to enjoy the best of Central Florida in a noisy world. This one bedroom condo is in original condition, with 3 year old A/C unit, and is ready for your personal touches to make it your own.

2500 Lee Road Unit 143, Winter Park
$365,000
3 Beds ⋅ 3 Baths ⋅ Cranes Creek SubDv. ⋅ 32792 Zip Code
Beautiful, move in ready townhouse located in the highly desirable area of Winter Park. This well-maintained home provides confort, convenience and a versatile layout perfect for modern living. Featuring a spacious 2 car garage and a flexible 4th room on the first floor, ideal for a home an office, guest bedroom or additional living space. Enjoy being just minutes from shopping, dining and everyday essentials, all while living in a quiet and attractive community. This home is the perfect blend of style, functionality and location. Ready for its next owner.

7506 Cranes Creek Court Unit 30, Winter Park
$269,000
2 Beds ⋅ 2 Baths ⋅ Lazy Oaks Condo SubDv. ⋅ 32792 Zip Code
Welcome to 5108 Lazy Oaks Drive, a 2-bedroom, 2-bathroom condo in a desirable Winter Park location. This light-filled home has approximately 1,008 square feet of comfortable living space with a functional floor plan, abundant windows, skylight and sliding glass doors that bring in plenty of natural light. The spacious living room features a beautiful brick fireplace and sliding glass door access to the screened-in back patio. The patio can also be accessed directly from the primary bedroom, creating a wonderful private outdoor space to enjoy your morning coffee, relax, or entertain. The primary suite features an en-suite bathroom with a walk-in shower, spacious two-sink vanity, and plenty of closet space. The guest bedroom is conveniently located just two steps from the second full bathroom, providing an ideal setup for family, guests, or a home office. The well-maintained original kitchen includes an electric range and oven, refrigerator, dishwasher, and two-basin stainless steel sink. Well-maintained tile flooring runs throughout the home, offering durability and easy maintenance. The spacious one-car garage has more than just parking, with a washer and dryer and plenty of additional storage space. The HOA fee is $277 per month and includes lawn maintenance and responsibility for the entire exterior of the condo, including the roof, providing added convenience and peace of mind for the homeowner. With its fresh interior, abundant natural light, brick fireplace, screened-in patio, private primary suite, attached garage, and low-maintenance lifestyle, 5108 Lazy Oaks Drive is a wonderful opportunity to own a comfortable home in Winter Park.

5108 Lazy Oaks Drive Unit 5108, Winter Park
$575,000
2 Beds ⋅ 3 Baths ⋅ Townhomes/Harper Place SubDv. ⋅ 32789 Zip Code
Virtually Staged. WINTER PARK, WITHIN REACH. A rare opportunity to step into one of Central Florida’s most coveted lifestyles. Bright, airy, remarkably spacious, this immaculate 2-bedroom townhome lives far larger than its approximately 1,600 sq.ft.suggests. Greet the day with a sunny disposition as morning light fills the oversized, east-facing primary bedroom. Step onto the private lanai with a latte, stretch into a little yoga, admire a garden of your own making. With plenty of room for herbs, vegetables & flowers—a quiet little corner of Winter Park to make entirely your own. Inside, real wood floors set a warm, welcoming tone throughout a surprisingly generous collection of living spaces. Formal living & dining rooms transition into an open kitchen w/island seating, breakfast area & family room, all with views toward the lanai & garden beyond. An immaculate townhome that lives large * Upstairs, a sense of space continues w/2 large primary suites. One features a a steeping tub, the other a shower, creating flexibility for guests, roommates, multigenerational living, or substantial home office beautifully accommodating overnight guests. Carpet is immaculate, but if your vision calls for something else, a $5,000 flooring credit is offered to make the space your own * Then step outside your front door. discover why Winter Park remains one of Central Florida’s most coveted communities. Michelin-acclaimed dining & AdventHealth’s primary medical campus within walking distance. Parks & green spaces surround you, while nearby Loch Haven Cultural Park puts the Orlando Museum of Art, Orlando Science Center and an extraordinary collection of theatrical & cultural venues practically in your backyard * Minutes away, celebrated Park Avenue & historic Hannibal Square invite you to linger over lunch at a sidewalk café, browse boutiques & galleries, meet friends for dinner, or simply wander beneath the canopy of one of Central Florida’s most beautiful communities. Saturday mornings are for the farmers market. Spring brings the nationally renowned Winter Park Sidewalk Art Festival. Central Park is an extension of the community’s backyard, while lakes, museums, theaters, restaurants & tree-lined streets create an unmistakable sense of place making Winter Park one of Florida’s most enduringly desirable addresses. When you’re ready to venture farther, leave the car behind. Rail connections put Downtown Orlando & Central Florida within easy reach, Brightline opens the door to West Palm Beach, Boca Raton, Fort Lauderdale & Miami.Amtrak connects Winter Park to destinations along the East Coast. Then come home. Fire up the grill, pull up a stool at the kitchen island, or settle into the family room for the game. With open views to the lanai & garden, you can keep an eye on the score—and watch the grill master sweat it out outside without missing a play. Dinner moves easily from kitchen to table to lanai. Stay outside for a glass of wine, enjoy the garden as evening settles in, then retreat upstairs to one of 2 wonderfully oversized primary suites. Even the practical details exceed expectations: a true two-car garage with a 220V outlet ready for EV charging, a substantial built-in storage system designed to handle everything you want to keep neatly tucked away. This isn’t simply an immaculate home. It’s an attainable doorway into the Winter Park lifestyle—a home that lives large, in a location that lets you live even larger. Click on the Virtual Tour to get the full picture

1259 Indiana Avenue, Winter Park
$1,350,000
6 Beds ⋅ 6 Baths ⋅ Lakeside Estates SubDv. ⋅ 32792 Zip Code
Virtually Staged. Welcome to your dream home in the highly sought-after Lakeside Estates neighborhood in Winter Park! This elegant 6-bedroom, 5-bathroom, 2 laundry rooms residence offers a perfect blend of modern comfort and timeless sophistication for the whole family. From the moment you enter, you will be captivated by the open concept design, high ceilings, an abundance of natural light. The gourmet kitchen features new quartz countertops, stainless steel appliances, and a spacious island that opens to the family and kitchen nook rooms for entertaining. New paint throughout. New garage coating on the floor. There are 2 primary suites, one on each level, that offers a peaceful retreat with a spa-inspired bath and walk in closets. After a long day, step outside to your private oasis complete with a covered lanai and fully screened-in sparkling pool and spa for hosting gatherings. With its beautifully design and prime location, this home is situated in a gated community, with easy access to top rated schools, boutique shopping, restaurants, and all the charm of Winter Park. Ready to call home!!

1445 Via Sangro Place, Winter Park
$1,449,000
3 Beds ⋅ 3 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code
A wonderful opportunity to build your dream home on one of Winter Park’s most idyllic streets. Situated on a quaint, one-way brick street with a charming park at its center, this exceptional 12,581-square-foot deep lot offers a rare combination of space, character, and location. Currently featuring a 3-bedroom, 2.5-baths, plus office home with 2,080 square feet, the property offers the flexibility to live in or rent the existing home while you finalize your plans and prepare to build. Ideally located within the highly sought-after “A” school district of Audubon K-8 and Winter Park High School, this property places you just minutes from downtown Orlando, Orlando Health, AdventHealth, and the Dr. Phillips Center for the Performing Arts. Enjoy easy access to the vibrant restaurants and shops along Corrine Drive, as well as the boutiques, dining, and charm of Park Avenue. A rare opportunity to create your ideal Winter Park residence in an extraordinary setting surrounded by convenience, character, and everything this coveted area has to offer.

150 E Reading Way, Winter Park
$660,000
3 Beds ⋅ 1 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code
An opportunity to build new in an established Winter Park neighborhood. The existing home remains on the property and is offered for its land value only, allowing a buyer to design from the ground up on a street where redevelopment is already underway. Within a half mile, seven custom single-family homes are in their final phase of construction, most starting near $1.5 million. Border Drive itself is a mix of longtime homes and newer builds, shaded by mature trees and free of through traffic. Once the site is prepared, the parcel supports a custom plan with room to work in a pool, covered lanai and summer kitchen. Bring your own builder, or ask for an introduction to builders already working in the area. Park Avenue shops and restaurants, Rollins College, the Farmers Market and the chain of lakes are all a short drive away. Property sold as is. The buyer is to verify setbacks, utilities, impact fees, demolition requirements and permitted building dimensions with the City of Winter Park.

1416 Border Drive, Winter Park
$359,000
3 Beds ⋅ 3 Baths ⋅ Aloma Trails SubDv. ⋅ 32792 Zip Code
Virtually Staged! Amazing Townhome! GATED Community of Aloma Trails Townhomes in a great Winter Park location, 3 bedroom, 2.5 bathroom with features of spacious living and comfortability. This stunning Townhome has Ceramic Tile flooring throughout the first floor leads to a kitchen with all the upgrades including SS appliances. 42” Cabinets, upgraded granite countertops and backsplash, and an island with plenty of seating along with a carpet in the second floor and all bedrooms. The master suite is outfitted with large Walk-In closet, glass-enclosed shower with dual sinks, and oversized cabinets. The two additional bedrooms share a second full bath and there is a half bath on the main floor convenient for guests. Separated interior laundry closet provides convenience and comfort. A nice big Car Garage and driveway, which will easily suit for multiple vehicles as necessary. This community comes with hassle-free lawn care, and well-maintained common areas and a BEAUTIFUL location. The fitness enthusiast will enjoy the Crunch Fitness facility just across the community and, the CADY WAY trail and the CROSS SEMINOLE trail- all just steps away from your front door. Walmart, Costco and Publix are almost 3 min driving distance. Close to Park Ave in Winter Park, SR 417, UCF, Fulsail University, and just 40 minutes to the Beach! Add in top notch Seminole County Schools. You don't need to look any further for your Dream Home! Schedule your viewing today! Note: Some of the pictures are showing the virtual staging of the unit and the furnitures/decorative items are not included to the listing.

7605 Aloma Pines Court, Winter Park
$519,900
3 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 1 SubDv. ⋅ 32792 Zip Code
Updated Winter Park home with 2,047 sq ft of heated/cooled living space, a huge backyard, and NO HOA. This is an owner-updated home—not a flip—with quality improvements completed over the past several years and professionally completed permitted work. Major improvements include a 2021 roof, 2021 whole-house repipe, 2021 exterior stucco and paint, 2020 HVAC, 2023 kitchen remodel, 2023 permitted 400 sq ft heated/cooled sunroom addition, 2024 permitted 20’ x 10’ storage building, and 2025 hurricane-impact windows. The expanded kitchen features granite countertops and backsplash, newer appliances, and a massive storage expansion. The bright 400 sq ft sunroom features wall-to-wall windows, a four-panel sliding glass door, and permanent AC and heat. A separate 200 sq ft tiled screened room provides additional outdoor living space. The property also offers a large backyard with plenty of room to enjoy, entertain, or expand. Located in a desirable Winter Park area with great schools and convenient access to shopping, dining, parks, and major roads. Extensive owner-quality improvements, major systems already updated, permitted additions, and no HOA. Buyer to independently verify all measurements, square footage, permits, schools, and other property information.

1660 Gladiolas Drive, Winter Park
$745,000
4 Beds ⋅ 4 Baths ⋅ Meadows At Hawks Crest SubDv. ⋅ 32792 Zip Code
Virtually Staged. Gated Community | Dual Primary Suites | Main-Level Living | Located in Winter Park’s gated Hawks Crest community, this two-story home pairs a spacious open floor plan with a private backyard setting and a layout that offers exceptional versatility. The main level includes the primary suite, dedicated study, laundry room, kitchen, and principal living areas, making day-to-day living possible without the need for stairs. The gourmet kitchen features quartz countertops and 42-inch cabinetry, while 8-foot interior doors add height and proportion throughout. Large sliding glass doors open to an oversized screened and covered patio with eastern exposure, morning sun, and no rear neighbors. Built in 2020, the home also offers the advantages of newer construction, complemented by a tile roof. Upstairs, the 4-bedroom, 3.5-bath floor plan includes three bedrooms, one serving as a second primary suite, along with a large bonus room and separate loft. Hawks Crest is set along Lake Howell and offers a clubhouse, fitness center, community pool, splash pad, parks, walking trails, grilling and picnic areas, and a pier with lake access. Park Avenue, shopping, dining, recreation, and major roadways are all within convenient reach.

1287 Verdant Glade Place, Winter Park
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