Winter Park Homes with Street Lights Community Features

Winter Park Homes with Street Lights Community Features

Welcome to Winter Park, Florida – a picturesque city that perfectly blends small-town charm with vibrant urban living. Known for its stunning lakes, lush parks, and historic architecture, Winter Park offers a serene escape just minutes away from the hustle and bustle of Orlando. With a rich cultural scene, residents enjoy an array of art galleries, museums, and theaters, making it a haven for creatives and art enthusiasts alike. The city is also home to the renowned Rollins College, adding an academic vibrancy to the community.

One of the standout features of Winter Park is its commitment to creating a welcoming and safe environment for families and individuals. The Homes with Street Lights community exemplifies this ethos beautifully. Imagine strolling through tree-lined streets illuminated by charming street lights, creating a warm and inviting atmosphere for evening walks or bike rides. This community fosters a sense of belonging, where neighbors become friends and children can play safely outdoors.

In addition to the aesthetic appeal, the Homes with Street Lights community is designed with convenience in mind. Residents have easy access to nearby parks, shopping, and dining options, ensuring that everything you need is just a stone's throw away. Whether you’re enjoying a lazy Sunday brunch at a local café or exploring the scenic beauty of the nearby lakes, Winter Park offers a lifestyle that is both enriching and enjoyable.

Discover the magic of Winter Park and experience the delightful charm of the Homes with Street Lights community – where every day feels like a vacation in your own backyard.

Newest Winter Park Homes with Street Lights Community Features

2 Beds ⋅ 2 Baths ⋅ Cedarwood Village SubDv. ⋅ 32792 Zip Code

Virtually Staged. LIVE THE WINTER PARK LIFESTYLE! STYLE, SPACE & LOCATION—THIS ONE HAS IT ALL! Welcome to Cedarwood Village, where easy living meets one of Winter Park’s most desirable locations, just minutes from the charm, dining, shopping, and entertainment of Downtown Winter Park and Park Avenue. This beautifully maintained 2-bedroom, 2-bath residence with an enclosed bonus room offers a spacious, light-filled floor plan designed for both comfortable everyday living and entertaining. Vaulted ceilings enhance the open living and dining areas, while the generously sized kitchen features newer appliances, abundant cabinet and counter space, plus room for a cozy breakfast table. Retreat to the oversized primary suite, complete with two large closets and sliding glass doors opening to the bonus room. The renovated primary bath adds a touch of luxury with an updated vanity and impressive custom walk-in shower. The guest bedroom offers its own sliding glass doors leading to the front patio, creating a bright and inviting space for family or overnight guests. The updated guest bath adds convenience with a washer and dryer neatly tucked away in the closet. One of the home's best features is the enclosed bonus room, offering valuable additional living space that's perfect for a home office, den, reading retreat, hobby room, or simply a relaxing place to unwind. Enjoy the Florida lifestyle without leaving the neighborhood! Cedarwood Village offers a sparkling community pool, two tennis courts, and clubhouse for residents to enjoy. And then there’s the LOCATION! Shopping, restaurants, medical facilities, and everyday conveniences are all close by, with easy access to major roadways and the boutiques, sidewalk cafés, restaurants, parks, and unmistakable charm of Park Avenue and Downtown Winter Park just minutes away. More than a home—it’s a Winter Park lifestyle. Come see why Cedarwood Village is such a special place to call home!

2477 Tahoe Circle Unit 2477, Winter Park

2 Beds ⋅ 3 Baths ⋅ Temple Trail Village SubDv. ⋅ 32789 Zip Code

A rare opportunity in Winter Park’s coveted 32789! This stunning fee-simple townhome offers the feel of a private retreat with the architectural pedigree of Fugelberg Koch (FK Architecture), the freedom of NO HOA FEES, and an extraordinary setting overlooking the 80-acre Howell Creek Preserve. Tucked away in a highly desirable Winter Park location, this 2-story end-unit lives much larger than its 1,701 square feet and delivers a lifestyle that is truly hard to replicate. The heart of this home may just be its incredible outdoor living space. Step through the living area and onto the expansive deck, where a covered canopy creates a year-round outdoor room overlooking the lush Howell Creek Preserve. With a firepit, market lighting, and treetop views stretching across the native Florida landscape, this is the kind of space that begs you to linger—morning coffee surrounded by nature, afternoon cocktails with friends, or evenings gathered around the fire under the lights. The elevated vantage point places you virtually eye-level with the cypress canopy, creating a dreamy sense of privacy and connection to nature that is rarely found in townhome living. And perhaps best of all, this is a view that cannot be renovated into another home. Inside, soaring 14-foot ceilings and dramatic picture windows fill the living room with an abundance of natural light while framing beautiful views of the preserve. The open, airy design makes the home feel exceptionally spacious and brings the outdoors in. The stunning kitchen features gorgeous Spanish tile flooring, solid wood cabinetry, granite countertops, and a new backsplash. The dining room adds character with built-in cabinetry and French doors, while the spacious indoor laundry room provides exceptional everyday convenience. Upstairs, two generously sized bedrooms and two full bathrooms provide a comfortable private retreat. A convenient powder room is located downstairs for guests. The coveted end-unit location also offers additional outdoor space along the side of the home, beautifully enhanced with brick hardscaping and room for relaxing, grilling, entertaining, or overflow parking. Parking is another standout feature, with a one-car garage plus two designated parking spaces—a rare convenience in this setting. And then there is the location. Situated in the prestigious 32789 zip code, this home puts you within walking distance of the Winter Park Racquet Club, the Winter Park Chain of Lakes, and surrounded by some of Central Florida’s most sought-after real estate. Enjoy the best of Winter Park while coming home to your own private perch above the trees. Fee-simple ownership. No HOA fees. Exceptional architecture. Preserve views. Incredible outdoor living. Coveted Winter Park location. This is far more than a townhome—it is a lifestyle.

2881 Temple Trail, Winter Park

5 Beds ⋅ 6 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code

Under Construction. Designed to capture the timeless character of Olde Winter Park while delivering an extraordinary level of modern luxury, this is a truly one-of-a-kind residence by Vimaro Homes. Set within the highly sought-after Park Grove neighborhood and designed by renowned architect Gary Hancock, the home makes an unforgettable first impression with a stately front façade, manicured grounds, dual porte cochere’s, and a motor court leading to a two-car garage. Every element has been thoughtfully considered to create a residence that feels as though it has always belonged in Winter Park. Inside, exceptional craftsmanship takes center stage. A marble mosaic entry introduces interiors defined by chevron-pattern hardwood flooring, refined millwork, natural stone, and carefully curated finishes. The floor plan is equally impressive, balancing grand entertaining spaces with an effortless sense of livability. The main level features a dedicated library/home office, formal dining room, and expansive gathering room overlooking the private courtyard. At the heart of the home, the chef’s kitchen pairs Calacatta marble countertops with a full suite of Thermador appliances, a statement ILVE range, and an oversized butler’s pantry offering exceptional prep and storage space. The first-floor primary suite is a private retreat with direct access to the courtyard and an incredible spa-inspired bath finished in marble. Dual vanities, Perrin & Rowe fixtures, a freestanding soaking tub, walk-in shower, and an expansive dressing room elevate the suite to another level. Upstairs, four generously proportioned bedrooms each feature an ensuite bath and walk-in closet, surrounding a spacious central loft ideal for an additional living or entertaining space. Continuing to the third level, a fully finished attic space provides an unexpected bonus room perfectly suited for a private gym or a game room. The outdoor living experience is just as remarkable. At the center of the home is a spectacular courtyard-style pool, creating a private resort atmosphere framed by the residence and lush landscaping. An expansive covered cabana provides multiple areas for dining and lounging, complemented by a fireplace and full summer kitchen for year-round entertaining. Beyond the courtyard, ample yard space adds another layer of usability rarely found with such an intimate outdoor design. This home also offers the rare opportunity to enjoy one of Winter Park’s most desirable residential settings while remaining within walking distance of the boutiques, acclaimed restaurants, cafés, and vibrant atmosphere of Park Avenue. Hannibal Square and Winter Park Village are also just moments away, placing some of the city’s best dining, shopping, and entertainment within effortless reach. Timeless in its architecture and uncompromising in its execution, this home is destined to become one of Winter Park’s most distinguished residences. Renderings are artistic interpretations. Features and finishes may vary from final construction.

857 Brock Street, Winter Park

Winter Park SubDv. ⋅ 32789 Zip Code

Rare Winter Park redevelopment opportunity on a nearly half-acre corner parcel just minutes from Park Avenue. Zoned R-3 (Medium-Density Residential), this parcel offers outstanding residential redevelopment potential, including up to seven residential units. Ideally situated between Park Avenue and Winter Park Village, the property enjoys convenient access to renowned dining, shopping, Rollins College, cultural attractions, AdventHealth Winter Park, and major transportation corridors. Three existing residences occupy the site and contribute no value to the offering. Opportunities of this size and zoning in such close proximity to Park Avenue are exceptionally uncommon.

540 N Pennsylvania Avenue, Winter Park

4 Beds ⋅ 5 Baths ⋅ Osceola Or Lakeview Deed SubDv. ⋅ 32789 Zip Code

Charming and Sophisticated, this single-story home combines the old with the new in such a seamless manner, you will walk through the etched glass front door and immediately have the desire to sit down with a glass of wine, listen the player piano, and you will never want to leave. Welcome to this Completely Renovated Custom Home in the highly coveted area of Winter Park, just a few blocks from Phelps Park, the YMCA, and a beautiful walk to the Park Avenue shops and restaurants. Walking up the paver drive, over the travertine front patio and stepping into this gorgeous home, you are greeted with the formal living room featuring a player piano, a beautiful marble wood burning fireplace, and hardwood floors that flow throughout the home. Turning to your right you will find 3 large bedrooms, 2 full bathrooms and 1 half bath. You will note one of these secondary bedrooms presents as an en-suite with a full bathroom. The other 2 bedrooms share a full bathroom, along with an auxiliary half bath. Moving forward through the living room you step into the stunning oversized dining room, complete with a wall-bar custom made in Italy along with a wine dispensing machine (picture the Wine Room) which conveys with the sale. From the dining room we step down into a chef's kitchen like no other. Stunning 42"white wood cabinets, quartz countertops, white subway tile backsplash, a 6-burner natural GAS RANGE, double oven, and the largest center island with a microwave and beverage cooler on either end. This magnificent kitchen opens up to a large family room with French doors, surround sound speakers and large sunlit windows. Walking through the family room you will find the primary suite tucked away in the back of the house for the ultimate private sanctuary. Along with the generously sized bedroom with French doors giving access to the backyard and pool, you will be in absolute awe of the incredible primary bathroom, featuring his and hers sinks, a standalone tub, and a double-sided walk-in shower with 2 showerheads and storage benches. The on-demand hot water heater servicing this bathroom means you will never run out of hot water! Oversized His and Hers closets are the proverbial icing on the cake to this primary retreat ("Hers" is the size of a bedroom!). Stepping outside to the cozy covered patio, you will be drawn to the heated, saltwater pool built new in 2023, along with a summer kitchen, electric fireplace, and outdoor TV entertainment, also featuring the cutest pool half bath (no more dripping wet indoor bathroom trips!). Complementing the pool area is a fully fenced backyard for the 2-legged and/or 4-legged kiddos, large privacy hedges, and NO REAR NEIGHBORS. This home comes complete with a whole house Sonos system and speakers playing music throughout the house, even on the back patio, along with a whole house security system including 2 cameras and a Ring doorbell through Vivint. The 2-car garage easily fits both of your vehicles and has amble overhead storage along with attic access. Freshly painted exterior in 2026! Roof is 2018, AC's are 2018, hot water heater is 2026, and an updated irrigation system supported by a private well. Zoned for the BEST SCHOOLS, you can walk to Lakemont Elementary! Middle school is Maitland Middle, and of course, Winter Park High School. Only one lucky family will be able to call this turn-key custom Winter Park home theirs. Make an appt today so that lucky family is yours!

890 N Phelps Avenue, Winter Park

4 Beds ⋅ 5 Baths ⋅ Villa View Park SubDv. ⋅ 32789 Zip Code

Custom-built Santa Barbara-style estate set on one of Winter Park's most coveted brick-paved streets, just moments from Park Avenue's boutiques, galleries and celebrated restaurants, Winter Park Golf Course, Winter Park Racquet Club, historic Rollins College and vibrant Winter Park Village. Built in 2010, this four-bedroom, 4.5-bath residence spans 3,661 square feet across two floors, with cathedral ceilings, a cozy fireplace and colonial windows and French doors, which frame the resort-style pool retreat. A gracious main-floor primary suite offers dual vanities and a large walk-in closet. The double-island chef's kitchen features a gas range and premium Thermador appliances, anchoring an open-plan living, dining and kitchen design, modeled for everyday ease and effortless entertaining. A flexible bonus space is ideal for a home office, formal dining or gym. Upstairs, three additional spacious bedrooms each offer their own en-suite bath and walk-in closet. The home wraps around a covered courtyard leading to the heated saltwater pool and spa, creating a private outdoor enclave. Parking is a breeze with an oversized two-car garage, additional golf cart parking, plus utility pad. Ample storage and workspace complete the rear of the property, which is also wired for a future whole-home generator. A rare offering in the heart of Winter Park, where timeless design meets an unmatched lifestyle.

645 Pansy Avenue, Winter Park

3 Beds ⋅ 3 Baths ⋅ Villas Of Aragon Condo SubDv. ⋅ 32789 Zip Code

Excellent Winter Park location! This 3 bedroom 2.5 bath quad-condo LIVES LIKE A PRIVATE 2-STORY HOME, with attached oversized 2 car garage, private patio and back fenced area. (The unit is attached to another only by a common garage wall.) Priced below market value to be sold AS-IS for the seller's convenience and TLC needed. ** One Year AHS Home Warranty included.** Nestled between Denning Dr and Orlando Ave, this home is an easy walk to the vibrant charm of Park Avenue, and close to the Winter Park Library, SunRail, and Rollins College. Publix and restaurants are just down the street! The first floor is tiled, with foyer entry, and comfortable family/dining/kitchen living area complete with fireplace. Sliding doors lead to a private patio. Upstairs, the large primary suite is a nice retreat with high ceilings, double walk in closets, double vanity and ample sized shower. Two more bedrooms and another bath complete the 2nd floor. High end washer and dryer are included in the attached garage, and a full wall workshop is in the garage too. Call to see it today!

1061 Aragon Avenue Unit 1061, Winter Park

Parklando 03 SubDv. ⋅ 32789 Zip Code

Fully remodeled! One of the most competitively priced homes featuring over 3,300 SF, in the 32789 zip code, and in the K-8 Audubon Park School District. The K-8 Audubon Park School District is a small pocket, and ranked one of the best district's in the state. Fully remodeled luxury pool homes in the highly sought-after Audubon K-8 and Winter Park school district with over 3,300 square feet of exceptional living space, capped with a brand-new, architecturally stunning tile barrel roof that blends timeless Mediterranean elegance with lasting durability. 2614 Parkland Drive, a fully reimagined luxury residence in the heart of Winter Park. This is your chance to own a showpiece property with over 3,300 SF zoned for the coveted Audubon Park K-8 and Winter Park High School districts. Completely remodeled in late 2022, this home radiates warmth and sophistication. Solid light oak floors, custom railings, and an open-concept flow make entertaining effortless. The chef’s kitchen is a centerpiece; quartz counters, full-height designer tile, and abundant storage bring form and function together. Out back, discover your private resort. A heatable custom pool & spa finished in ultra-rare Caribbean blue tile sets the tone; elevated with two natural-gas fire pits, dramatic waterfalls, porcelain privacy walls, and a built-in grill. Every evening feels like a five-star escape.The first-floor master suite offers direct access to the outdoor oasis, while upstairs features three oversized bedrooms, a loft, and a private patio for sunset views. Brand-new tile roof, dual tankless water heaters, central vacuum, and all-natural gas appliances ensure low-maintenance, worry-free living. This is more than a home it’s a statement. A chance to live where luxury, location, and lifestyle converge.

2614 Parkland Drive, Winter Park

3 Beds ⋅ 3 Baths ⋅ Grayson Square SubDv. ⋅ 32792 Zip Code

Step into this beautifully designed townhome featuring an open-concept kitchen, dining, and living area—perfect for everyday living and entertaining. The modern kitchen boasts stainless steel appliances, gray cabinetry, and quartz countertops. Upstairs, the spacious primary suite offers a walk-in closet and a private in-suite bath with dual quartz vanities, while two additional bedrooms, a full bath, and a convenient laundry closet complete the second floor. Relax on the covered lanai and enjoy the privacy of this home's cul-de-sac location. The HOA includes landscaping, exterior maintenance and repairs, high-speed internet, and access to the gated community, providing low-maintenance living. With no CDD, this home is an excellent option for both homeowners and investors. Ideally located in highly desirable Winter Park, Grayson Square is just minutes from SR-436, SR-434, and SR-417, with Publix, Starbucks, shopping, dining, and top-rated Seminole County schools nearby. Park Avenue is only a short drive away, making this home the perfect combination of convenience, comfort, and value.

2033 Canny Cove, Winter Park

3 Beds ⋅ 3 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just minutes from Park Avenue, Winter Park Village, Rollins College and downtown Orlando, you'll enjoy the perfect balance of lake life, tranquility and accessible convenience. Experience award-winning dining, boutique shopping, entertainment, cultural attractions and everyday conveniences just moments from your future home. Priced to encourage redevelopment, this property is adjacent to 230 Killarney Drive, creating a rare opportunity to purchase one or both parcels. Together, they form an extraordinary double-lot assemblage with expansive views of Lake Killarney and endless possibilities to design a landmark residence. Whether purchased individually or together, opportunities to own on Lake Killarney are exceptionally limited. Build the custom home you've envisioned while enjoying one of Winter Park's most coveted locations from this desirable homesite with private lake access and the ability to build your own dock.

240 Killarney Drive, Winter Park

4 Beds ⋅ 1 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just minutes from Park Avenue, Winter Park Village, Rollins College and downtown Orlando, you'll enjoy the perfect balance of lake life, tranquility and accessible convenience. Experience award-winning dining, boutique shopping, entertainment, cultural attractions and everyday conveniences just moments from your future home. Priced to encourage redevelopment, this property is adjacent to 240 Killarney Drive, creating a rare opportunity to purchase one or both parcels. Together, they form an extraordinary double-lot assemblage with expansive views of Lake Killarney and endless possibilities to design a landmark residence. Whether purchased individually or together, opportunities to own on Lake Killarney are exceptionally limited. Build the custom home you've envisioned while enjoying one of Winter Park's most coveted locations from this desirable corner homesite with private lake access and the ability to build your own dock.

230 Killarney Drive, Winter Park

4 Beds ⋅ 3 Baths ⋅ Lakeside Estates SubDv. ⋅ 32792 Zip Code

Experience refined Florida living in this exceptional single-story residence, ideally situated on a quiet cul-de-sac within an intimate gated community in one of Winter Park's most desirable locations. Impeccably maintained, this elegant home offers over 3,000 square feet of thoughtfully designed living space with 4 bedrooms, 3 full baths, a private office, and a desirable three-way split floor plan that provides both privacy and flexibility. Designed for comfortable everyday living and effortless entertaining, the home features formal living and dining rooms, a spacious family room, and a bright breakfast area. The stunning gourmet kitchen is the heart of the home, showcasing timeless white cabinetry, quartz countertops, abundant prep space, a convenient butler's pantry, and an open flow to the main living areas. The generous primary suite offers a spacious walk-in closet and a luxurious retreat, while quality finishes and meticulous attention to detail are evident throughout. Enjoy year-round outdoor living on the private screened lanai, perfect for relaxing or entertaining. Additional highlights include a three-car garage, a durable tile roof, and a fully paid solar energy system, keeping the average monthly electric bill under $100. Combining elegance, energy efficiency, and an outstanding location, this move-in-ready home offers the perfect balance of luxury, comfort, and convenience.

1492 Via Sangro Pl, Winter Park

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