Winter Park Homes with Rain Gutters Exterior Features

Winter Park Homes with Rain Gutters Exterior Features

Winter Park, located in the state of Florida, is a charming city known for its picturesque beauty and rich history. Situated in Orange County, Winter Park offers a unique blend of natural landscapes, cultural attractions, and a thriving real estate market.

One notable feature of homes in Winter Park is the presence of rain gutters in their exteriors. These rain gutters play a crucial role in protecting the homes from water damage during heavy rainfall. They help to channel the water away from the roof and foundation, preventing potential leaks, flooding, and erosion.

The inclusion of rain gutters in Winter Park homes is a testament to the city's commitment to maintaining the integrity and longevity of its properties. It showcases the attention to detail and quality craftsmanship that homeowners and builders prioritize in this area.

Investing in a home with rain gutters in Winter Park is a wise choice, as it ensures the protection and preservation of your property. Whether you are a first-time homebuyer or looking to upgrade, these exterior features add value and peace of mind.

In addition to the practical benefits, Winter Park offers a variety of recreational activities, including parks, lakes, and cultural institutions. The city's vibrant downtown area is filled with boutique shops, art galleries, and fine dining establishments, making it an ideal place to live and explore.

With its beautiful homes featuring rain gutters and a thriving community, Winter Park is an excellent choice for those seeking a blend of natural beauty, historic charm, and modern conveniences.

Newest Winter Park Homes with Rain Gutters Exterior Features

1351 Mayfield Avenue, Winter Park
$3,050,000
5 Beds ⋅ 5 Baths ⋅ Temple Heights SubDv. ⋅ 32789 Zip Code
Under Construction. A commanding front façade, and a coveted brick-street setting near the Vias. Interiors defined by natural stone, architectural detail, and a thoughtful balance of grandeur and intimacy. This distinctive Winter Park residence brings together the elements that make a luxury home memorable and a location that is difficult to replicate. The arrival is dramatic featuring a soaring two-story foyer that opens to a spacious living room where wood beams and substantial stonework establish a rich material palette. A stone-wrapped fireplace anchors the room, complemented by a built-in entertainment center and a wet bar with a wine refrigerator and sink. Whether hosting a large gathering or enjoying an evening by the fire, the space feels equally suited to both. Taj Mahal countertops take center stage in the kitchen, paired with custom cabinetry, a paneled refrigerator, and a Thermador appliance package. A generous adjoining dirty kitchen provides a separate sink and additional prep-space. The downstairs primary suite offers privacy and direct access to the backyard through sliding doors. In the bath, marble finishes, dual vanities, and a freestanding soaking tub create an elegant retreat. An arched shower entrance introduces a distinctive architectural detail, with dual shower heads completing the experience. An expansive closet by Idelli brings the same attention to detail to the dressing space. A second downstairs suite accommodates guests or a private office, while a laundry room supports everyday convenience. Upstairs, three additional bedrooms and a spacious bonus room create a separate setting for family, guests, and recreation. The outdoor living space is equally as impressive. A full summer kitchen sets the stage for open-air dining, with a heated pool and spa providing the centerpiece for afternoons and evenings at home. Substantial green space adds another dimension to the backyard, offering room to gather beyond the pool. The surrounding neighborhood places this residence in exceptional company, with impressive estates lining the street. Phelps Park and the YMCA are within walking distance; the Winter Park Racquet Club, Park Avenue’s boutiques and restaurants, and downtown Winter Park are close by. Interlachen Country Club further enhances the appeal of this sought-after location. With its stunning architecture, richly appointed interiors, and exceptional outdoor living, this residence makes a lasting statement on one of Winter Park’s coveted brick streets.

1351 Mayfield Avenue, Winter Park
2507 Lafayette Avenue, Winter Park
$1,850,000
4 Beds ⋅ 6 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code
A striking modern façade introduces this exceptional new residence by SoulTech Homes, where bold architectural expression meets beautifully considered interiors. Distinguished by extensive custom millwork, sophisticated paneling, and integrated LED lighting, the home delivers a level of detail and finish rarely found at this price point. An intelligently designed floor plan balances dramatic gathering spaces creating a home equally suited to memorable entertaining and effortless everyday living. At the heart of the residence, a spectacular double-height living room makes an unforgettable impression. A soaring paneled feature wall, accented by ambient LED lighting and a custom entertainment center, brings depth, texture, and architectural presence to the space. The kitchen pairs White Paradise quartz countertops with custom cabinetry and a full suite of Thermador appliances. Designed to be as functional as it is beautiful, this culinary centerpiece is complemented by a wine bar featuring a wine refrigerator and display shelving illuminated with integrated LED lighting. A spacious walk-in pantry and mudroom area adds exceptional everyday convenience. A downstairs guest suite offers comfortable accommodations, while a dedicated office provides a refined setting for working from home. Upstairs, the primary suite becomes a private sanctuary. An expansive dressing room complements the retreat, while the luxurious bath invites relaxation with a freestanding soaking tub, dual vanities, and a generous walk-in shower. Two additional upstairs bedrooms each enjoy it's own bathroom, and a conveniently positioned laundry room completes the upper level. The backyard is designed for entertaining. Approx. 900 SF of outdoor living space flows straight from the main living area, anchored by a 201 SF covered patio for shaded dining and gatherings in any weather. Around it, a 702 SF pool deck frames a heated 12' x 24' pool, with plenty of room for loungers, a dining table, and guests spilling out from the house. A full summer kitchen turns the backyard into a true outdoor room, so hosting a dinner party or a weekend pool day feels like a natural extension of the home. A metal roof, and enhanced landscaping complete the property’s polished presentation. The location adds another compelling dimension. Set within an evolving neighborhood experiencing an exciting wave of new construction, the home places you close to Park Avenue’s celebrated shops and restaurants, within walking distance of the Winter Park Racquet Club, and near the Maitland Art Center and Phelps Park. From its commanding first impression to its thoughtfully appointed private spaces, this residence offers a distinctive expression of modern luxury, bringing together architectural drama, exceptional craftsmanship, and the ease of Winter Park living.

2507 Lafayette Avenue, Winter Park
3148 Nicholson Drive, Winter Park
$449,000
3 Beds ⋅ 2 Baths ⋅ Wrenwood Unit 3 4th Add SubDv. ⋅ 32792 Zip Code
Virtually Staged. Welcome to this beautifully maintained and extensively updated split-plan home with NO HOA in desirable Winter Park! Featuring 3 bedrooms and 2 bathrooms, this home sits on a beautifully manicured lot with a fantastic floor plan designed for both comfortable everyday living and entertaining. The home boasts a completely remodeled kitchen in (2026), featuring updated finishes and a fresh, modern feel, along with new flooring (2026), bathroom upgrades (2026), and new appliances (2024). Additional improvements include a new roof (2021), new water heater (2025), and Solar Tubes a compact, energy-efficient system that channels natural daylight from your roof that bring in extra natural light, creating a bright and welcoming atmosphere. The popcorn ceilings have been removed and replaced with an updated drop-down ceiling finish, adding to the home's refreshed look. Fresh exterior paint (2024) provides even more curb appeal! Separate formal living and dining rooms offer wonderful spaces for entertaining, while the spacious kitchen with breakfast bar opens to the family room, making it the perfect gathering spot for family and friends. The generous owner's suite features a double closet and private en-suite bath. Two additional spacious bedrooms offer flexibility for family, guests, a home office, or a playroom. Step outside and enjoy your own fully fenced backyard oasis! Entertain on the oversized covered lanai with ceiling fan, or enjoy the beautiful mature trees and fruit trees throughout the property. A NEW storage shed added in 2025 provides even more room for tools, hobbies, and outdoor equipment. Additional features include an irrigation system, whole-house water softening system, double-pane windows, and storm shutters for added peace of mind during Florida's storm season. Conveniently located just 10 minutes from downtown Winter Park, with easy access to I-4 and 417, this home offers the perfect combination of comfort, convenience, and thoughtful updates. Zoned for highly rated Seminole County schools, this is a wonderful opportunity to own a move-in-ready home with so many major improvements already completed!

3148 Nicholson Drive, Winter Park
531 Worthington Drive, Winter Park
$1,100,000
3 Beds ⋅ 3 Baths ⋅ Kenilworth Shores SubDv. ⋅ 32789 Zip Code
Virtually Staged. OUTSTANDING OPPORTUNITY!! Delightful 2,626 sq ft home, perfectly positioned on a charming corner lot in the vibrant 32789 neighborhood! With its array of newly constructed homes nearby, this well-cared-for property stands as a fantastic blank canvas, just waiting for your creative touch. The updated kitchen boasts modern cabinets, chic countertops, and stainless steel appliances, complete with a cozy breakfast nook to enjoy your morning coffee. Entertain in style in the formal dining room or gather around the fireplace in the living room. The original primary suite, alongside a guest bedroom and bathroom, features exquisite parquet floors and beautiful crown molding that add a touch of elegance. Imagine hosting friends in the spacious family room, adorned with beamed ceilings, or retreating to the incredible second-story master suite, where an impressive 18x12 bathroom, huge walk-in closet, and private 31x9 balcony await, all overlooking a charming, landscaped backyard. Step outside to enjoy the roomy L-shaped covered porch and take advantage of the two separate garages (24x23 & 22x14) plus a gated side yard perfect for storage (NO HOA!)—completing this exceptional offering! This home is zoned for the highly regarded Brookshire Elementary, Glenridge Middle, and Winter Park High, plus the delightful shops and dining along Winter Park’s Park Avenue are just a short drive away. Don’t miss your opportunity to make this enchanting home yours! WELCOME HOME!

531 Worthington Drive, Winter Park
2885 Roxbury Road, Winter Park
$450,000
3 Beds ⋅ 2 Baths ⋅ Fairbanks Shores 2nd Add SubDv. ⋅ 32789 Zip Code
Original hardwood floors, an updated kitchen, and a versatile bonus room highlight this three-bedroom, two-bath home with 1,511 heated square feet at 2885 Roxbury Road, Winter Park, FL 32789. A fenced backyard, outdoor deck, and practical system improvements complement the home’s original character. The kitchen features quartz countertops, stainless steel appliances, an island, and pantry cabinetry. Hardwood flooring extends throughout the main living spaces and bedrooms, with tile in the kitchen, bathrooms, and bonus room. Use the bonus room for additional seating, hobbies, or a home office while maintaining all three bedrooms. Cedar-lined closets in the primary bedroom and an additional bedroom provide a distinctive detail. Improvements include a roof installed in 2019, air conditioning replaced in 2020, an electrical panel replaced in 2021, and double-pane windows in the bedrooms. Additional updates include exterior paint, replacement front, back, and kitchen doors, and front and rear gutters. The backyard deck extends the living space outdoors, with room for dining, relaxing, or container gardening. A fenced yard and an private storage shed provide additional functionality. A carport, irrigation system, and available fiber-optic internet round out the features. The septic system was pumped in 2026. This Winter Park home combines hardwood floors, an updated kitchen, flexible bonus space, and outdoor living in one inviting property.

2885 Roxbury Road, Winter Park
1934 Taylor Avenue, Winter Park
$499,000
4 Beds ⋅ 2 Baths ⋅ Eastgate Sub SubDv. ⋅ 32792 Zip Code
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.**Welcome to 1934 Taylor Avenue, a charming mid-century modern home offering 4 bedrooms and 1.5 bathrooms in Winter Park's established Eastgate neighborhood. Full of character and personality, this single-story home blends timeless design with comfortable everyday living. Hardwood floors throughout the main living areas add warmth and character, while the 1.5 bathrooms feature classic, colorful details that add a fun and distinctive charm. The kitchen makes its own statement with a pop of color on the cabinets and playful vinyl flooring. The open floor plan seamlessly connects the living and dining areas, creating an inviting space for relaxing and entertaining. The split-bedroom layout provides added privacy and flexibility for family members and guests. French doors lead to the backyard, creating a lovely connection between indoor and outdoor living. A welcoming front porch offers a cozy spot to enjoy your morning coffee. The private backyard provides plenty of space for outdoor activities and relaxation, with a spacious deck perfect for gatherings and an open patio offering additional room for outdoor seating. Conveniently located near Aloma Avenue, this home offers easy access to shopping, dining, parks, and everyday essentials. Nearby destinations include the Winter Park YMCA, Rollins College, and Downtown Winter Park's popular Park Avenue, known for its boutique shops, restaurants, and entertainment. With its mid-century modern character, colorful details, versatile outdoor spaces, and convenient location, 1934 Taylor Avenue offers a unique opportunity to enjoy Winter Park living.

1934 Taylor Avenue, Winter Park
1400 Pelican Bay Trail, Winter Park
$968,000
5 Beds ⋅ 4 Baths ⋅ Pelican Bay SubDv. ⋅ 32792 Zip Code
Awesome 5 bedroom 3.5 bathroom custom built home on gorgeous 1.2 acre WATERFRONT cul-de-sac lot in lovely Pelican Bay of Winter Park. A True Gem on the Lake on a private dead-end street! Step through the front door and into a welcoming foyer with beautiful wood floors and oversized living and family rooms featuring dual wood-burning fireplaces. 4 BRAND NEW CUSTOM BAY WINDOWS (NOV 2026) installed in living room. The gourmet kitchen features classic oak cabinetry and upgraded granite counters, as well as BRAND NEW STAINLESS STEEL SIDE BY SIDE REFRIGERATOR (NOV 2026). Kitchen bay windows overlook massive screened rear porch, screened pool oasis, and breathtaking backyard waterfront views of Lake Florence. Main bedroom is downstairs and features large ensuite bathroom with dual sinks, garden tub, and walk in shower. Additional 4 bedrooms and 2 full bathrooms as well as bonus room are located upstairs and enjoy wonderful lakefront views. BRAND NEW ROOF INSTALLED NOV 2021. This oversized lot contains a variety of wonderful fruit trees and edible plants located around the property including avocado, purple yam, lychee, chinese chives, jujube, apple cactus, persimmon, mango, and dragon eye. The lake frontage speaks for itself, but as you can imagine the sunsets are truly superb. The Winter Park location is one of the best, close to shopping, schools, major roads, international airport, and amazing restaurants. Bring your buyers so they can make this beautiful custom home their own.

1400 Pelican Bay Trail, Winter Park
647 Randy Lane, Winter Park
$1,699,999
4 Beds ⋅ 4 Baths ⋅ Timberlane SubDv. ⋅ 32789 Zip Code
WINTER PARK LUXURY LIVING! Welcome to 647 Randy Lane, where timeless elegance meets modern sophistication in one of Winter Park's most desirable locations! Offered for the first time in over a decade, this beautifully maintained residence is situated on an expansive 0.36-acre corner lot, surrounded by lush, mature landscaping and designed for exceptional Florida living. Step inside to discover a spacious, open-concept, floor plan that effortlessly blends comfort, style, and functionality. At the heart of the home is a stunning chef's kitchen featuring gorgeous quartz countertops, premium Wolf double ovens, and a built-in Sub-Zero refrigerator—perfect for everyday living and entertaining alike. Your private backyard oasis awaits! Enjoy an oversized swimming pool, expansive patio, and generous green space, all surrounded by tropical landscaping that creates a peaceful, resort-style atmosphere. Thoughtful outdoor lighting sets the stage for evening entertaining, while the seamless indoor-outdoor flow makes this home ideal for enjoying Florida's beautiful weather year-round. Impressive upgrades and features include a NEW ROOF (2024), SOLAR PANELS (2022), resurfaced pool and updated pool tile (2021), tankless gas water heater, well irrigation system, and an oversized indoor laundry room. LOCATION, LOCATION, LOCATION! Just minutes from Winter Park's iconic Park Avenue, you'll enjoy convenient access to exceptional dining, boutique shopping, beautiful parks, and cultural attractions. The property is also zoned for sought-after schools, including Audubon K-8 and Winter Park High School. Buyers should verify current school assignments. Luxury, privacy, and an unbeatable Winter Park lifestyle—all in one exceptional property! Don't miss this rare opportunity to make 647 Randy Lane your next home.

647 Randy Lane, Winter Park
1441 Grove Terrace, Winter Park
$5,950,000
5 Beds ⋅ 6 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code
Under Construction. Exceptional waterfront living meets European-inspired design in this new Vimaro Homes residence on Lake Sylvan. Positioned on an oversized Winter Park lot with 130 feet of water frontage, the home pairs timeless architecture, richly detailed interiors, and expansive outdoor living. Led by a husband-and-wife team originally from Europe, Vimaro Homes brings together her expertise in interior design and his in construction. Their hands-on approach brings a personal commitment to every selection and detail, prioritizing lasting quality, thoughtful design, and craftsmanship over the cost-driven formulas common in investment-built spec homes. A striking façade and tile roof establish an elegant arrival, complemented by a dual-entry driveway featuring a diamond-patterned composition of turf and concrete. An underground three-car garage preserves the architectural approach, while an elevator connects all three levels. Inside, a marble mosaic entry introduces intricate trim work and classic reeded crown molding, establishing the home’s enduring character. The spacious living room features a marble-wrapped fireplace, custom built-ins with LED up-lighting, and expansive sliding doors framing views of the pool and lake. The kitchen pairs marble countertops and custom inset cabinetry with Perrin & Rowe fixtures and Thermador appliances, including a paneled refrigerator. A substantial scullery with a prep kitchen and pantry supports entertaining, while the nearby dining room overlooks the water. The downstairs primary suite offers a private retreat with its own fireplace and an expansive, custom-fitted walk-in closet with a center island. The primary bath features Casablanca marble tile, dual vanities, Perrin & Rowe fixtures, and a spacious walk-in shower. Upstairs, four additional bedrooms each offer an ensuite bath and walk-in closet, alongside a bonus room, laundry room, and terrace. Throughout the home, natural stone, finely crafted cabinetry, and classic architectural details reflect the team’s European influences. Outdoors, a generous lanai with retractable screens and a full summer kitchen extends the living spaces toward Lake Sylvan. A three-tiered deck brings together a pool, spa, and sweeping water views, while expansive green space and a dock complete the waterfront setting. Set on a brick street moments from Park Avenue’s restaurants, boutiques, and cafés, this residence combines Winter Park’s distinctive character with an exceptional lakefront setting. Shaped by the personal vision and craftsmanship of Vimaro Homes, it offers a refined expression of waterfront living.

1441 Grove Terrace, Winter Park
1441 Palm Avenue, Winter Park
$2,449,000
5 Beds ⋅ 5 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code
Under Construction. In the heart of Winter Park’s coveted Tree Streets, this stunning residence brings together impeccable finishes, a striking architectural presence, and a location that puts so much of daily life within easy reach. Opportunities to find new construction in this established neighborhood are becoming harder to come by, making this home an especially exciting offering. The front façade makes a memorable first impression, with beautiful curb appeal that carries naturally into the interiors. In the spacious living room, a stone-wrapped fireplace anchors the space, complemented by a built-in entertainment center and display shelving with soft LED underlighting. The kitchen is a standout. Calacatta quartz countertops and an intricate mosaic backsplash set an elegant tone, while a full suite of Thermador appliances, including a paneled refrigerator, brings substance to the beautiful design. A spacious pantry keeps everything tucked away, and a wine bar with a dedicated wine refrigerator makes hosting feel effortless. The primary suite offers a lovely sense of retreat. This spacious bedroom is complemented by a beautifully finished bath with marble mosaic tile, a freestanding tub, and a generous walk-in shower with a rain showerhead. An oversized closet adds the kind of everyday luxury that is just as valuable as the finishes themselves. A rare first-floor guest bedroom gives visitors a comfortable place of their own or offers a space for a dedicated office. Upstairs, three additional bedrooms, each with a walk-in closet, surround a loft that offers room for a second living area, movie nights, or a quiet place to unwind. The outdoor living is equally impressive, with a spacious covered lanai and full summer kitchen overlooking the pool and spa, a beautiful setting for dinners or a quiet afternoon at home. Surrounding green space gives the backyard a sense of openness and room to enjoy the Florida sunshine. With Phelps Park and the YMCA moments away, and Park Avenue’s restaurants and boutiques just a golf cart ride from home, the location is every bit as appealing as the residence itself. Beautifully finished and thoughtfully arranged, this is a chance to enjoy the ease of a brand-new home in a neighborhood whose charm has long been established.

1441 Palm Avenue, Winter Park
2718 Eastern Parkway, Winter Park
$2,450,000
4 Beds ⋅ 5 Baths ⋅ Parklando SubDv. ⋅ 32789 Zip Code
Exceptional craftsmanship, bespoke finishes, and impeccably appointed interiors define 2718 Eastern Parkway, a newly constructed residence by Barefoot Brothers Construction in Winter Park. Offering 3,308 square feet of thoughtfully designed living space, this four-bedroom home with four full baths and one half bath seamlessly blends timeless architecture with modern luxury. A gated front courtyard creates a gracious arrival experience, setting the tone for the exceptional attention to detail found throughout. Inside, detailed ceilings, and wainscotting, rich engineered hardwood flooring, custom millwork, and artisanal built-ins create a sophisticated yet welcoming atmosphere. Influenced by British Colonial design, the interiors showcase layered textures, refined architectural details, and carefully curated finishes that elevate everyday living. The expansive great room flows effortlessly into the dining area and chef's kitchen, providing an elegant setting for both intimate gatherings and grand entertaining. Designed as the heart of the home, the kitchen features striking quartzite countertops, custom tailored cabinetry, a walnut island, and luxurious appliances. A separate walk-in pantry and refined scullery provide discreet preparation and storage spaces, while a dedicated mudroom enhances functionality without compromising style. Privately situated on the main level, the primary suite serves as an opulent retreat, complete with an artfully crafted walk-in wardrobe and a spa-inspired bath featuring dual vanities, a freestanding soaking tub, an oversized walk-in shower, a private water closet, and linen storage. Upstairs, a second primary suite offers equally impressive accommodations with its own walk-in closet and well-appointed en-suite bath. Two additional bedrooms, each featuring private en-suite baths, provide exceptional comfort and flexibility for family and guests. The home's outdoor living experience is equally compelling. A covered lanai overlooks a private resort-style pool, while the summer kitchen with built-in grilling station creates the perfect backdrop for year-round alfresco dining and entertaining. Additional highlights include a two-car garage, natural gas service, two tankless water heaters, and abundant storage solutions throughout. Located in the heart of Winter Park, the home enjoys convenient access to the area's most coveted destinations, including Park Avenue's renowned boutiques, fine dining, sidewalk cafés, Central Park, museums, galleries, the farmers market, and Winter Park Village. Defined by bespoke craftsmanship, luxurious millwork, and thoughtfully curated design, the well appointed 2718 Eastern Parkway home presents a rare opportunity to experience elevated living in one of Central Florida's most desirable communities.

2718 Eastern Parkway, Winter Park
1825 Chilean Lane, Winter Park
$450,000
5 Beds ⋅ 3 Baths ⋅ Eastbrook Sub Unit 05 SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully renovated pool home featuring a rare and versatile double primary suite layout! Completely renovated in 2024, this 5-bedroom, 3-bathroom home offers 1,636 square feet of stylish, thoughtfully designed living space with modern finishes throughout. Light gray wood-look plank tile flooring and recessed lighting create a bright, cohesive feel. The contemporary kitchen showcases gray shaker-style cabinetry, sleek black granite countertops, a marble-look tile backsplash with black mosaic accents, stainless steel appliances, and a breakfast bar with seating for four. The first primary suite is privately positioned away from the additional bedrooms and features an ensuite bathroom with a marble-look tiled shower, decorative mosaic accents, multiple shower heads including a rain shower, a frameless glass enclosure, and a gray vanity topped with black granite. The second primary suite provides added flexibility for multigenerational living, extended guests, or a private retreat. Step outside to enjoy your own backyard oasis, complete with an in-ground pool, screened lanai, and fully fenced, spacious backyard with plenty of green space for relaxing, entertaining, and outdoor activities. Ideally located approximately 10 minutes from the restaurants and boutiques of Park Avenue, with convenient access to UCF, Full Sail University, Rollins College, major transportation routes, shopping, and dining. Orlando International Airport is approximately 25 minutes away. With its modern renovations, dual primary suites, and inviting outdoor living space, this home offers a unique combination of comfort, flexibility, and convenience! ROOF - 2024 HVAC - 2025 PLUMBING - 2026 ELECTRICAL - 2024

1825 Chilean Lane, Winter Park
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