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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

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

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

1140 Washington Avenue Unit 16C, Winter Park
$739,000
3 Beds ⋅ 3 Baths ⋅ Quarters At Winter Park Condo SubDv. ⋅ 32789 Zip Code
Renovated in 2022, this 3-bedroom, 2.5-bath home offers 2,069 square feet of bright, modern living space. The open main level connects the living area, dining space, and kitchen, which has stainless steel appliances and sleek contemporary cabinetry. A fireplace anchors the living room, and large windows bring in natural light throughout. Upstairs, the oversized primary suite gives you room to spread out, with two more bedrooms for guests, a home office, or flexible space. Step outside to a private courtyard with a outdoor kitchen, a quiet place for morning coffee or evening dinners . A 2-car garage with electric car charger and large driveway complete the package. Roof replacement Jan 2027. 5-minute walk to Rollins College and 10 minutes on foot to Park Avenue’s shops, restaurants, and Saturday farmers market. You can leave the car in the garage.

1140 Washington Avenue Unit 16C, Winter Park

700 Melrose Avenue Unit B23, Winter Park
$295,000
2 Beds ⋅ 2 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code
Enjoy beautiful pond and garden views from this tastefully updated two-bedroom, two-bath upstairs condominium in Winter Park Gardens. The kitchen features solid-surface countertops and wood cabinetry, while both bathrooms offer updated vanities and elegant finishes. Plantation shutters, laminate and tile flooring complement the inviting interior. A bright Florida room with floor-to-ceiling windows provides the perfect setting to relax and take in the breathtaking pond and garden views. The unit is also plumbed for convenient in-unit washer and dryer installation. Set on more than eight acres of lush, meticulously maintained grounds, Winter Park Gardens features landscaped gardens, a tranquil pond, and a community pool. Located next door to the Winter Park Tennis Center and within walking distance of Rollins College and Park Avenue, this beautifully maintained and managed community places you minutes from Winter Park’s finest restaurants, gardens, and parks.*Click on Virtual Tour for video overview of this exceptional community!

700 Melrose Avenue Unit B23, Winter Park

1118 Washington Avenue Unit 5C, Winter Park
$895,000
3 Beds ⋅ 3 Baths ⋅ Quarters At Winter Park Condo SubDv. ⋅ 32789 Zip Code
Welcome to 1118 Washington Ave, a spacious 3-bedroom, 2.5-bath townhome in one of Winter Park's most walkable and sought-after locations. 2,100 square feet of light-filled living space, plus a 300+ square foot glass atrium, puts the best of the city right outside your door. The showstopper is the one-of-a-kind glass atrium / covered patio. Sunlight pours in, and it's great for morning coffee, dinner with friends, or a quiet evening with a book. You won't find another like it! Inside, the open, airy layout flows easily from living areas to bedrooms. Updated flooring gives the home a clean, move-in-ready feel, and the A/C was replaced in 2024. A brand-new roof is being installed, so you can buy with confidence. The spacious two-car garage gives you plenty of room for vehicles, storage, and hobbies. The location is what makes this home special. Park Avenue's boutiques, cafés, and restaurants are just steps away, and Rollins College is nearby. Walk to the Winter Park Tennis Center, or spend afternoons at Seven Oaks Park and Mead Botanical Garden. A stroll down to the lake is part of your everyday routine. Few homes put so much of what makes Winter Park special within a few minutes' walk. Come see why this one is a rare find.

1118 Washington Avenue Unit 5C, Winter Park

1350 Lyndale Boulevard, Winter Park
$1,499,000
4 Beds ⋅ 4 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code
Photos coming soon. Experience timeless elegance and exceptional living in the heart of Winter Park! Nestled along a charming, quiet brick-lined street just moments from iconic Park Avenue, this beautifully designed custom residence offers the perfect combination of sophistication, comfort, and Florida indoor-outdoor living. Featuring 4 bedrooms, 3 full bathrooms, 2 half bathrooms, and 3,478 square feet of living space, this impressive home welcomes you with soaring 10-foot ceilings, rich Brazilian cherry hardwood floors, elegant architectural details, and an abundance of natural light. At the heart of the home, the gourmet kitchen is designed for both everyday living and effortless entertaining, featuring a spacious center island, natural wood cabinetry, premium cooking appliances, built-in refrigerator, and wine refrigerator. The kitchen flows seamlessly into the inviting family room, complete with a beautiful gas fireplace. The luxurious first-floor primary suite offers a peaceful retreat with generous walk-in closets, a spa-inspired bathroom, and French doors opening to the private screened pool and patio. Upstairs, additional bedrooms and a spacious bonus room provide flexibility for a home office, fitness studio, media room, or guest accommodations. Step outside to your own private oasis, where a sparkling pool, relaxing spa, mature landscaping, and inviting outdoor living spaces create an ideal setting for entertaining or unwinding year-round. Additional highlights include formal living and dining spaces, an attached two-car garage, abundant storage, and a desirable location with no HOA. Enjoy the best of the Winter Park lifestyle, with convenient access to Park Avenue's celebrated restaurants, boutique shopping, cafés, cultural attractions, parks, and nearby lakes. An exceptional opportunity to own a distinctive residence in one of Central Florida's most desirable communities. Schedule your private showing and discover everything this Winter Park home has!

1350 Lyndale Boulevard, Winter Park

700 Melrose Avenue Unit A22, Winter Park
$310,000
2 Beds ⋅ 2 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code
Discover the charm of Winter Park Gardens, a sought-after 55+ community nestled among more than 8 acres of lush landscaping, majestic live oak trees, winding walking paths, and tranquil pond views. This inviting 2-bedroom, 2-bathroom condo offers approximately 1,074 square feet of comfortable living space. One of its most special features is the enclosed, air-conditioned Florida room, where dramatic floor-to-ceiling windows frame beautiful pond and garden views, creating the perfect setting to enjoy your morning coffee, unwind with a good book, or simply take in the peaceful surroundings. Thoughtfully updated by the current owner within the past year, improvements include a new tankless water heater, new toilets, upgraded electrical panel, new primary bedroom window, new primary bathroom vanity, and new closet doors throughout the hallway and bedrooms. The kitchen features updated appliances, including a newer refrigerator, and washer/dryer hookups add everyday convenience. One assigned parking space is also included. Enjoy the community swimming pool and beautifully maintained grounds. Conveniently located within in a few short minutes of downtown Winter Park, Park Avenue, Rollins College, and Mead Botanical Garden, this residence offers the perfect blend of comfortable living, natural beauty, and the sought-after Winter Park lifestyle. Experience the convenience, peaceful surroundings, and unique appeal that make Winter Park Gardens such a special place to call home!

700 Melrose Avenue Unit A22, Winter Park

4940 Tangerine Avenue Unit 4940, Winter Park
$249,000
3 Beds ⋅ 2 Baths ⋅ Wrenwood Condo SubDv. ⋅ 32792 Zip Code
Spacious living, valuable updates, and easy condo ownership come together at 4940 Tangerine Avenue in Winter Park’s established Wrenwood community! This generously sized three-bedroom condominium offers room to spread out, with flexible space for guests, a home office, or everyday living. Major improvements include a replaced air-conditioning and heating system, water heater, and electrical panel, adding comfort and value where it matters most. The community has also recently completed roof replacements on all buildings, all building where completely repainted and the driveway and parking throughout the condo complex have been completed—another standout benefit for your next home. Enjoy a refreshing swim in the community pool, gather with neighbors at the clubhouse, and spend more time enjoying life with the convenience of low-maintenance condominium living and affordable association fees. Conveniently located near shopping, dining, and major roadways, Wrenwood offers easy access to Winter Park’s many attractions and Park Ave. Whether you’re looking for a primary residence or a Florida getaway, this spacious three-bedroom condo deserves a place at the top of your list!

4940 Tangerine Avenue Unit 4940, 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

1500 Harris Circle, Winter Park
$1,175,000
3 Beds ⋅ 3 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code
English cottage–inspired architecture, enchanting gardens and a setting directly across from Lake Sylvan introduce this exquisitely renovated Winter Park residence. Set among distinguished residences and substantial lakefront estates, the home occupies a corner lot along a charming brick street and offers three bedrooms, three full bathrooms and approximately 2,096 square feet of living space. Extensive improvements in recent years bring together exceptional finishes, thoughtful craftsmanship and substantial updates behind the walls. With interior design by New York City–based Paulette Pascarella, traditional architectural details find fresh expression through sophisticated materials and beautifully considered modern appointments. Expansive windows welcome natural light, while polished marble flooring in warm ivory tones extends throughout much of both levels. The kitchen features solid wood cabinetry, quartz countertops and a full-height backsplash, complemented by a Bertazzoni refrigerator, Bosch 800 Series gas range and Miele dishwasher. A separate study and sitting room has wood flooring and custom built-ins. With a full bathroom immediately adjacent, this versatile space presents potential for conversion into a fourth bedroom with an en-suite bath. Carefully selected details include Visual Comfort and Currey lighting, Buster + Punch and Baldwin hardware, and custom window treatments incorporating designer textiles and motorized shades from The Shade Store. Nine Marvin Ultimate windows with wood interiors, a VELUX skylight and a mahogany Craftsman front door further distinguish the renovation. A custom stair railing by Boris Petkoff Iron Works and millwork by Dunning Custom Carpentry add distinctive craftsmanship. All three bedrooms are upstairs, where the primary suite features soaring ceilings, treetop outlooks and an extensively fitted California Closets walk-in dressing room with custom cabinetry and soft-close dovetail drawers. Its beautifully appointed bathroom features Perrin + Rowe Georgian Era vanity and shower fixtures, reflecting the caliber of fittings selected throughout the home. Two additional bedrooms, one with an en-suite bathroom, provide flexibility for guests or a home office. Upstairs views of Lake Sylvan connect the interiors to their picturesque surroundings. Substantial improvements include whole-house repiping, electrical upgrades, a Rinnai tankless water heater and a whole-house water treatment system. The roof was replaced in August 2023. Outside, cottage gardens frame a welcoming entrance, while an intimate brick patio nestled within the garden and a quiet garden corner offer peaceful places for morning coffee or an afternoon outdoors. A private parking pad adds convenience. Beyond the garden, oak-shaded brick streets invite leisurely walks past beautiful homes and scenic views of Lakes Sylvan and Osceola. A small lakeside green space lies just down Harris Circle, with Crosby Wellness Center, AdventHealth and Park Avenue’s dining, boutiques and cultural attractions conveniently nearby. An inviting choice for a primary residence or Winter Park retreat.

1500 Harris Circle, 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

7463 Canford Court Unit 15, Winter Park
$270,000
3 Beds ⋅ 3 Baths ⋅ Whisperwood Condo SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully updated corner home in the Whisperwood community of Winter Park! Featuring 3 bedrooms and 2.5 bathrooms, this property offers an open-concept layout designed for comfortable living and entertaining. The fully remodeled kitchen adds a modern touch. The flooring on the second-floor and the staircase has also been updated. The spacious primary bedroom features a private bathroom and its own balcony, creating a relaxing retreat. Enjoy the enclosed patio, perfect for unwinding or entertaining guests. A convenient half bathroom on the first floor is ideal for visitors, and the in-home washer and dryer add everyday convenience. Situated at the end of the street, this corner home offers a desirable location within the community. Conveniently located near shopping, dining, UCF, Full Sail University, and major roadways, including SR 417 and SR 408. Don’t miss the opportunity to make this inviting Winter Park home your own!

7463 Canford Court Unit 15, Winter Park

1940 Magnolia Avenue, Winter Park
$1,190,000
4 Beds ⋅ 4 Baths ⋅ Temple Terrace Annex SubDv. ⋅ 32792 Zip Code
New roof fall 2026! Exceptional custom-built estate offering unparalleled security, efficiency and peace of mind on two expansive lots in the heart of Winter Park. This split-plan three-bedroom and 2.5-bath home has over 4,880 total square feet in the main home and 1,944 total square feet in the detached in-law/office unit under roof. Constructed with solid poured concrete block and 1-inch insulation, this remarkable residence was designed to withstand the test of time while delivering modern luxury and comfort. A rare feature, the home includes two reinforced safe rooms built with rebar-reinforced solid poured concrete walls and 12-inch concrete ceilings, along with a built-in, concrete-bolted safe. Additional security enhancements include a full alarm system and security spotlights. Designed for everyday living and entertaining, the property is equipped with a full-house 22-kilowatt generator, a buried 500-gallon propane tank, propane gas range and outdoor grill, two tankless water heaters, whole-house water softening and filtration systems, EV charging capability and energy-efficient construction resulting in remarkably low utility costs. The well-appointed kitchen features a solid wood cabinetry, quartz countertops, a kitchen, butler pantry, coffee bar and laundry room, Verona gas range, Frigidaire Professional French-door refrigerator, KitchenAid dishwasher, convenient under-counter outlets and the kitchen island has lighted shelves. Additional highlights include plantation shutters throughout, wine cellar, climate-controlled storage attic, granite in baths, custom garage cabinetry, epoxy-finished garage floors, hurricane-impact windows in the office/apartment, Pet Turf in the entire backyard with no maintenance necessary and a striking 35-foot flagpole. Combining superior craftsmanship, advanced infrastructure and thoughtful upgrades rarely found in today's market, this extraordinary property presents a unique opportunity to own a one-of-a-kind residence. Total heated square footage includes heated/cooled space to use as garage, workshop, and/or utility room in the detached structure.

1940 Magnolia Avenue, Winter Park

603 Carnation Drive, Winter Park
$399,900
4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub SubDv. ⋅ 32792 Zip Code
Private in-ground pool on a 9,000+ sq ft lot in Winter Park, with no HOA. This 4 bed, 2 bath home has 1,427 sq ft of updated living space and an open floor plan with hardwood and vinyl floors throughout. The kitchen was remodeled in 2021 and comes with all appliances, including the refrigerator, range, dishwasher, and microwave. The big-ticket items are already done: roof replaced in 2022, A/C in 2019, plumbing updated in 2021, and a new main electrical panel in 2026. The first-floor primary suite has a walk-in closet, and the other three bedrooms give you room for guests, a home office, or a gym. Outside you get a covered carport, a private entrance, and a large backyard built around the pool. Just minutes from Winter Park dining and shopping, with Lakemont Elementary nearby. Schedule your private showing today.

603 Carnation Drive, Winter Park

1825 Whitehall Drive, Winter Park
$3,195,000
4 Beds ⋅ 6 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code
1825 Whitehall Drive announces itself in stone. Twin gables of whitewashed stone, a stately brick entry, and striking black-framed windows define its European-inspired architecture in Winter Park’s coveted Kenilworth Shores. Brand-new and awaiting its first owner, this expansive custom residence offers over 4,300 square feet of timeless character and bespoke craftsmanship. Inside, natural light moves across wide-plank engineered white oak floors. Grand entertaining spaces meet intimate rooms. Architectural symmetry defines the great room, where a soaring fluted terrazzo fireplace is framed by custom cabinetry and brass picture lights. Expansive glass opens to the lanai, while a sitting room features a custom bar with brass mesh cabinetry, illuminated shelving, glazed tile, and wine refrigeration. The kitchen is a masterpiece, and you'll know it the moment you walk in. A Taj Mahal quartzite island commands the room, framed by floor-to-ceiling bespoke cabinetry, illuminated reeded glass, and a sculptural fluted hood. Sweeping waterfall edges meet a custom fluted wood base. A 48-inch Viking gas range, double ovens, and separate refrigerator and freezer columns complete the kitchen. Beyond, a windowed butler’s pantry offers quartzite countertops, illuminated shelving, and beverage refrigeration. Opening to the pool, the dining room invites memorable dinners that linger long after the last guest should have left. And then there's the first-floor primary suite—where luxury becomes personal. Vaulted ceilings with stained oak beams bring warmth and architectural character, while the bathroom is a destination in itself. Brass-inlaid marble floors, lilac-veined stone, a quartzite double vanity, and makeup station introduce a spectacular wet room with four rainfall showerheads, two handheld showers, and a sculptural fluted soaking tub. An oversized, fully customized walk-in closet features built-in cabinetry and elegant glass-front displays. Just off the foyer, the library is a room you'll fall in love with. Color-drenched walls, a stained oak-plank ceiling, custom built-ins, and brass-lit shelving create an intimate retreat, enclosed in glass with doors to a secluded side patio. The mudroom, plum-cabinetry laundry, and plaster-inspired powder bath complete the level. Upstairs, a light-filled loft opens to an uncovered terrace with checkerboard stone flooring, made for sunset conversations beneath the stars. Three bedrooms each feature an en-suite bath and custom closet. A jewel-box powder bath and vaulted bonus room, ideal for a cinema or game lounge, complete the level. Outside, a covered lanai with stained tongue-and-groove ceiling features a summer kitchen in whitewashed brick, fluted cabinetry, and leathered granite. French-pattern Talya leathered stone frames the PebbleTec pool, tanning ledge, inset spa, and calming waterfall—a setting made for sunlit afternoons, entertaining, and memorable evenings. Custom-built by Structure Redevelopment, LLC, this residence reflects a passion for distinctive architecture, superior craftsmanship, and uncompromising detail. Among Kenilworth Shores' distinguished residences and lakefront estates, it places you moments from Park Avenue’s restaurants, boutiques, and cafés, Rollins College, and the Chain of Lakes. Schedule your private showing today.

1825 Whitehall Drive, Winter Park

2887 Temple Trail, Winter Park
$695,000
2 Beds ⋅ 3 Baths ⋅ Temple Trail Village SubDv. ⋅ 32789 Zip Code
Some homes stand out because of their finishes. Others because of their location. Rarely do you find one that brings both together so beautifully. Nestled alongside an 81-acre nature preserve, this reimagined two-story, fee-simple, end-unit townhouse offers contemporary living surrounded by nature. With approximately 1,800 square feet, 2 bedrooms, 2.5 bathrooms, and no HOA, this exceptional property feels more like a personal retreat than a traditional townhome. Designed with a modern, contemporary point of view, the home features bamboo hardwood floors and 14-foot vaulted ceilings that give the main living space an open, light-filled atmosphere, while a sleek gas fireplace brings warmth and character to the room. The kitchen includes an eat-in breakfast nook. Granite countertops, custom soft-close cabinetry, high-end stainless steel appliances, gas cooking, and a wine refrigerator combine style with everyday functionality. Additional built-ins provide attractive storage while maintaining the home's clean, cohesive aesthetic. A spacious interior laundry and utility room with an additional refrigerator provides added storage. Upstairs, the primary suite takes full advantage of the home's exceptional setting, offering peaceful views across the surrounding greenery. The primary bath features dual sinks, vanity, stone countertops, and a spacious walk-in shower with three shower heads, including a rain shower. A spacious walk-in closet completes the suite. A second bedroom and full bath provide comfortable accommodations for guests or the flexibility to create a home office or personal retreat. Parking is also a standout feature, with a one-car garage plus two designated parking spaces. Outside is where the personality of this property really comes to life. The oversized upper and lower decks create an exceptional outdoor living experience. The upper deck features a gas grill for cooking and entertaining, along with spectacular views of rocket launches from Cape Canaveral. An area provides space for relaxing, while an outdoor shower, potting station, plenty of exterior storage, and a private backyard with access to Howell Branch Creek for kayaking add to the property's distinctive appeal. Lush tropical landscaping creates a garden-like setting with citrus trees, including lemon, avocado, papaya, and a unique cocktail tree, complemented by fragrant jasmine and colorful seasonal blooms. An outdoor fire pit adds warmth and ambiance on cooler evenings. Whether you're having coffee before the day begins, sharing dinner with friends, or just enjoying the quiet after sunset, the natural surroundings make these spaces feel remarkably removed from city life. Key updates include a new tile roof replacement, HVAC installation, and water heater in 2018. Located in Winter Park's 32789 ZIP code, the home is near the Winter Park Racquet Club, Winter Park Chain of Lakes, iconic Park Avenue, fine dining, upscale boutiques, Rollins College, and highly regarded schools, including Dommerich Elementary and Winter Park High School. SunRail is also nearby, with Maitland just minutes away. Modern interiors, exceptional outdoor space with spectacular views, and the convenience of Winter Park, all in one place. For the buyer who has been waiting for something genuinely special, this may be the one.

2887 Temple Trail, Winter Park

220 Killarney Bay Court Unit 6-2, Winter Park
$335,000
2 Beds ⋅ 2 Baths ⋅ Killarney Bay Condo SubDv. ⋅ 32789 Zip Code
LAKE KILLARNEY • WINTER PARK • CONDO DUES JUST $455 MONTHLY! • Enjoy exceptional value in Killarney Bay, a private lakefront community offering an oasis in the city! This second-floor, 2-bedroom, 2-bath corner condo features 1,140 square feet of comfortable, low-maintenance living with a BRAND-NEW HVAC SYSTEM INSTALLED IN MAY 2026 and a recently upgraded full-size washer and dryer. Community roof replacement is underway, with completion scheduled for November 2026, and this unit’s roof special assessment has already been PAID IN FULL by the sellers! Inside, an open floor plan, high ceilings and abundant natural light create a welcoming atmosphere. A corner electric fireplace anchors the living and dining area, while wood-look laminate flooring flows throughout the main living spaces. The kitchen offers upgraded cabinetry with decorative glass-front accents, generous counter space, a breakfast bar and a separate pantry. The primary suite includes a spacious walk-in closet and private bath with a glass-enclosed shower, decorative tilework and a furniture-style vanity. The second bedroom opens to its own covered, screened balcony—an inviting spot to unwind outdoors. A second bathroom features a tub with a glass enclosure, and the separate laundry room provides cabinetry, shelving and additional storage. Community amenities include a swimming pool, lakefront dock, fishing, a waterfront deck overlooking Lake Killarney, paddleboard and kayak storage, and assigned covered parking. Situated along a no-outlet road with limited traffic, this peaceful retreat is just minutes from Winter Park Village, Trader Joe’s and an array of restaurants, shops and entertainment. An appealing choice for a primary residence or seasonal getaway!

220 Killarney Bay Court Unit 6-2, Winter Park

617 N Interlachen Avenue, Winter Park
$4,695,000
11 Beds ⋅ 8 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code
Designed by renowned architect James Gamble Rogers II, 617 N Interlachen Ave presents a rare opportunity to own and thoughtfully reimagine a distinctive Spanish Revival estate in the heart of Winter Park. Built in 1929, renovated in 1981, and featuring extensive roof updates completed in 2020 and 2021, this character-filled property reflects the timeless architectural appeal that makes Winter Park so special. Situated on approximately half an acre, the estate includes a main residence plus three accessory buildings encompassing approximately 6,354 square feet combined, providing an exceptional amount of space and flexibility to create a property tailored to your lifestyle and vision. From the moment you arrive, the classic Spanish Revival influence and established setting offer a sense of history and individuality rarely found in newer construction. The multiple buildings create exciting possibilities for guest accommodations, private home offices, studios, hobby spaces, entertaining areas, or other uses permitted by applicable zoning and regulations. The residence offers an opportunity to preserve its distinctive architectural character while updating and personalizing the interiors and amenities for today's lifestyle. For buyers who appreciate homes with a story, architectural distinction, and the potential to make a property uniquely their own, this estate stands apart from the typical Winter Park offering. Even more compelling is the location. The property is within walking distance of Winter Park's famous Park Avenue, renowned for its restaurants, boutiques, cafes, galleries, cultural attractions, and unmistakable charm. Enjoy the rare opportunity to leave the car at home and stroll to one of Central Florida's most celebrated dining, shopping, and entertainment destinations. Rollins College is also nearby, while convenient access to downtown Orlando combines the charm and sophistication of Winter Park with easy connectivity to the greater Orlando area. The property is not individually listed on the Winter Park Register of Historic Places and is not located within a locally designated historic district, an important consideration for buyers exploring future renovation and personalization plans. Buyers should independently verify applicable zoning, permitting, building, and preservation requirements for any intended improvements or uses. With its James Gamble Rogers II design, 1929 origins, Spanish Revival character, approximately half-acre setting, substantial combined square footage, three accessory buildings, and an outstanding location within walking distance of famous Park Avenue, 617 N Interlachen Ave is far more than a conventional home purchase. It is an opportunity to take a distinctive piece of Winter Park architecture and shape its next chapter. Bring your vision and discover the possibilities where history, architecture, location, and potential come together in a truly one-of-a-kind Winter Park estate.

617 N Interlachen Avenue, Winter Park

1600 Legion Drive, Winter Park
$3,495,000
5 Beds ⋅ 6 Baths ⋅ Green Oaks Rep SubDv. ⋅ 32789 Zip Code
Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Keith D. Field. Conceived as the opposite of a production home, it was crafted with a builder’s eye for structural integrity, thoughtful flow, and a seamless connection between indoors and out. Set on a generous 91-foot wide lot, this custom residence offers 5 bedrooms and a floor plan that feels both substantial and inviting. A wide front veranda sets a timeless tone from the moment you arrive. Dark-framed windows and doors create a striking contrast, while manicured hedges and brick-paved drives enhance the classic curb appeal and highlight the home’s architectural details. Step inside and you immediately sense that this is more than just a beautiful house—it’s a home with a story. At its heart is the reclaimed pine flooring, sourced from a Florida bridge. Rich with character, worn in all the right ways, these floors bring a warmth and authenticity you simply cannot replicate with something new. A long, gracious foyer introduces the main living spaces. To your left, a handsome study/office with a brick fireplace offers an intimate retreat for working. To your right, a formal dining room with garden views comfortably accommodates twelve. A discreet swing door leads to a well-appointed wet bar and large walk-in pantry, which then opens into the expansive kitchen. The kitchen is the true hub of the home, anchored by coffered ceilings, an oversized island, a full suite of high-end appliances, abundant cabinetry, and extensive counter space. A light-filled dinette offers the perfect spot for casual meals. At the center of the home, an oversized great room draws everyone together with its tall brick fireplace, built-in display/bookshelves, and high ceilings that add volume without sacrificing warmth. Two bedrooms are thoughtfully located on the main level, including the primary suite, privately positioned in one of the quietest corners of the home. Filled with soft natural light, accentuating the detailed millwork that runs from floor to ceiling. The primary bath is a retreat in itself, featuring slate flooring, double vanity, claw-foot soaking tub, water closet, walk-in shower with rain head, and a massive custom walk-in closet. The second main-level bedroom functions beautifully as a guest suite or flexible space, with an en-suite bath that also serves as a pool bath, a built-in Murphy bed with integrated cabinetry. A back facing staircase leads to two additional en-suite bedrooms on the second level. At the top of the landing, a large built-in workstation creates an ideal homework or creative zone, and both bedrooms enjoy access to a full-length front balcony. At the back of the home, a separate staircase leads to the fifth bedroom—a wonderfully private suite with dormer windows, angled ceilings with beams, and its own en-suite bath. In addition to a walk-in closet, cleverly designed built-in storage along the walls ensures a place for everything. Off the great room, a covered lanai with tongue-and-groove wood ceiling and brick built-in grilling station creates a comfortable space for year-round relaxation. A 45-foot lap pool is anchored by a striking cabana with fireplace, evoking a resort-inspired setting for long afternoons, evening gatherings, and memorable celebrations. This is a rare opportunity to own a thoughtfully crafted estate where history, craftsmanship, and everyday comfort come together in perfect balance.

1600 Legion Drive, Winter Park

1681 Woodland Avenue, Winter Park
$2,629,000
5 Beds ⋅ 5 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code
Under Construction. A striking interpretation of Modern Tudor design brings a fresh architectural presence to one of Winter Park’s charming brick streets. Newly built, this stunning residence pairs a distinctive façade with interiors that feel both richly detailed and effortlessly livable. From the marble mosaic foyer to the private poolside retreat, each space offers its own expression of luxury, creating a home with character, warmth, and a beautiful sense of arrival. Beyond the entry, the spacious living area unfolds beneath shiplap ceiling details that lend texture and architectural depth. A statement wall with an electric fireplace anchors the room, establishing an inviting setting for quiet evenings and lively gatherings alike. The kitchen takes center stage with Taj Mahal countertops and a full suite of Thermador appliances. A built-in paneled refrigerator preserves the cabinetry’s seamless appearance, while a spacious walk-in pantry provides ample storage beyond the main kitchen. Positioned downstairs, the primary suite offers a peaceful retreat with a spacious closet and a beautifully composed spa bath featuring dual vanities, a freestanding soaking tub, and a separate shower with a rain showerhead and marble mosaic tile. A second downstairs guest suite adds exceptional versatility, a rare feature for the area, providing comfortable accommodations for visitors or a space for a private office. Providing comfortable accommodations for visitors or an inspiring space for a private office. Upstairs, three additional bedrooms, each with a walk-in closet, offer room for family and guests. A spacious loft introduces another place to gather, unwind, or create a dedicated media or recreation space, while the upstairs laundry room brings convenience to daily routine. Outdoors, a covered lanai with a summer kitchen sets the scene for alfresco dining and entertaining space. Lush landscaping surrounds the pool and spa, creating a beautiful backdrop for entertaining or simply enjoying the Florida lifestyle. Energy efficient doors and windows complete the home’s thoughtful collection of features. The location places neighborhood favorites within easy reach, with Phelps Park and the YMCA just a walk away and Park Avenue’s shops, restaurants, and cafés a short golf cart ride from home. Distinctive in its architecture and generous in its design, this residence offers a compelling opportunity to enjoy brand-new construction amid the established charm of Winter Park.

1681 Woodland Avenue, Winter Park

1011 Mckean Circle, Winter Park
$6,000,000
5 Beds ⋅ 7 Baths ⋅ Palmer Park SubDv. ⋅ 32789 Zip Code
Pre-Construction. To be built. (NOTE: Photos show features and finishes representative of the construction budget and selection allowances. All tile, colors, stone, cabinets, vanities, lighting, appliances, wallpaper to be CUSTOM SELECTED by Buyer. Also, layout of the rooms in in the photos may differ from the home to be built here.) The home is located on McKean Circle, one of the most sought-after, quiet, NO TRAFFIC streets in Winter Park… Very close walk to Park Avenue restaurants and shopping and Winter Park Golf Course. Presented by an established, award winning luxury home builder, this bespoke home will include premium features, appliances, fixtures and finishes as follows: ELEVATOR, NATURAL GAS WHOLE HOUSE GENERATOR, WOLF/SUB ZERO appliances and wine cooler tower, built-in coffee maker, LUTRON RA3 SMART LIGHTING AND WIRING FOR BLINDS AND DRAPES, AUDIO/VIDEO, SMART HOME and SECURITY UPGRADES, WALLPAPER, special carpentry and architectural details, CEILING DETAILS with LED recessed/cove LIGHTING. FIRST FLOOR PRIMARY SUITE WITH WASHER/DRYER and two-person shower, additional GUEST SUITE FIRST FLOOR, OFFICE FIRST FLOOR, 12' FIRST FLOOR CEILINGS with 10’ DOORS. UPSTAIRS THERE EN SUITES plus large LOFT with wet bar and laundry room. Store-front window and door system with SMART GLASS (on demand opaque or clear), large 18’x10’ full-view garage door, circular driveway, heated swimmable pool with spa, plenty of pool deck space, and exquisite landscaping. A 6’ masonry-stucco wall with gates will encompasses the property. Outdoor living includes a large rear covered lanai with retractable screens and a large summer kitchen, pool-bath and outdoor shower. Enjoy two fireplaces: a linear fireplace (choose natural gas or electric) in living room and optional natural gas fireplace on the pool deck. Great fortune comes to those who TAKE IMMEDIATE ACTION when opportunity presents itself. Call now to schedule your meeting with the Builder to get started on your new home today!

1011 Mckean Circle, Winter Park

1355 Hibiscus Avenue, Winter Park
$2,100,000
5 Beds ⋅ 6 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code
Virtually Staged. Situated along one of Winter Park's charming, tree-lined brick streets, this beautifully maintained traditional residence offers over 4,100 square feet of thoughtfully designed living space, with 5 bedrooms, 5 full bathrooms, and 1 half bath. Timeless architectural details and modern comforts create a welcoming home designed for both everyday living and entertaining. A welcoming front porch leads into elegant interiors featuring a private office with custom built-ins and a glass pocket door, along with a formal dining room accented by a tray ceiling and ambient lighting. The living room showcases exposed ceiling beams, crown molding, built-in shelving, and a gas fireplace, while French doors open to the screened lanai, creating a seamless connection to the outdoors. The kitchen features expansive countertops, abundant cabinetry, a center island with prep sink, walk-in pantry, and breakfast nook with access to the outdoor living area. A butler's pantry with wine refrigerator adds convenience for entertaining. The main-level primary suite offers a relaxing retreat with dual vanities, a soaking tub, and multiple closets. A second ensuite bedroom on the first floor, complete with a beverage refrigerator and coffee station, provides additional privacy and comfort for guests. A dedicated laundry room completes the main level. Upstairs, a built-in desk and cabinets line the hallway for study or work space. Generous loft with custom cabinetry, accent lighting, and beverage refrigerator creates a versatile second living area. Three additional bedrooms provide comfortable accommodations, including two connected by a Jack-and-Jill bathroom and a third with access to a nearby full bath. The second laundry room adds flexibility and convenience. Outdoors, enjoy a private backyard retreat featuring a screened lanai, swimming pool, outdoor kitchen, mature landscaping, and a full pool bathroom. Recent improvements include interior paint, a new second-floor Daikin AC system with UV lights, updated Hayward pool equipment, including the pump, DE filter, heater, chlorination system, whole-house Brita water filtration, epoxy garage flooring, new carpeting, refinished wood floors, polished countertops, and fiber-optic connectivity. Additional updates include a new roof (2023), commercial-grade water heater (2022), exterior paint (2024), and new appliances: fridge, dishwasher, washer and dryer. Conveniently located near the Vias and Winter Park Racquet Club, and just minutes from Park Avenue's renowned shopping and dining, the YMCA, medical facilities, and nearby public and private schools, this home offers the charm of Winter Park living with convenient access to recreation, dining, and everyday essentials.

1355 Hibiscus Avenue, Winter Park

1411 Devon Road, Winter Park
$950,000
2 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster SubDv. ⋅ 32789 Zip Code
Experience the charm of Winter Park living in this beautifully renovated Orwin Manor residence, where more than $41,000 in luxurious upgrades complement timeless character, sophisticated interiors and exceptional outdoor living in one of the area’s most desirable settings. Nestled along a tree-lined street and surrounded by mature landscaping, this 1,947-square-foot home offers two bedrooms, two baths and a versatile floor plan that can be easily converted back to its original three-bedroom configuration, providing flexibility for a home office, guest room or additional bedroom. Inside, rich hardwood flooring, crown molding, plantation shutters and a wood-burning fireplace lend warmth and character to the home, while French doors and abundant windows invite natural light throughout. The kitchen serves as an elegant centerpiece with custom cabinetry, Carrara marble countertops, a gas range and oven, stainless steel appliances, a breakfast bar and generous workspace. A tankless water heater adds modern efficiency and convenience. Multiple living and dining areas create an effortless flow for entertaining, while the expansive primary suite offers a private retreat with ample space for a sitting area. Beyond the interiors, the backyard creates a private resort-style setting rarely found so close to the heart of Winter Park. Fresh landscaping surrounds a saltwater pool, putting green, and expansive paver patio. A covered outdoor living and dining area provides an inviting backdrop for year-round entertaining. Mature trees, manicured hedges and multiple seating areas enhance the sense of privacy, creating a serene escape equally suited for quiet mornings, afternoons by the pool and evenings with guests. A paver driveway and charming covered entry complement the home’s classic architecture, while a Tesla charger adds the convenience of at-home EV charging. Ideally positioned in Orwin Manor, the residence is just minutes from I-4 access and AdventHealth, with convenient proximity to Park Avenue’s renowned boutiques, dining and cafés, as well as College Park and Downtown Orlando. Zoned for Killarney Elementary School, College Park Middle School and Edgewater High School, this distinctive residence presents an exceptional opportunity to enjoy the best of the Winter Park lifestyle.

1411 Devon Road, Winter Park

700 Melrose Avenue Unit M23, Winter Park
$289,000
2 Beds ⋅ 2 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code
Virtually Staged. Winter Park living, with a view you’ll actually want to come home to! This spacious 2-bedroom, 2-bath condo at Winter Park Gardens is clean and puts you in the middle of it all while giving you a peaceful place to escape. Set on the second floor with elevator access, the home overlooks the community pool and lush mature gardens, giving the living spaces a beautiful green backdrop. Step inside, to your open living area, flooded with natural light. The Florida room adds an extra spot to relax with a good book, work from home, or enjoy your morning coffee, with updated windows bringing in plenty of natural light while helping to keep cooling costs low. Fresh interior paint gives the home a clean, updated feel and an easy canvas for your own style. Just outside your door, Winter Park Gardens offers beautifully landscaped grounds, a community pool, pond, and lighted walking paths. Then there's the location. Walk or bike ride to Park Avenue's restaurants, shopping, and boutiques, the Winter Park Tennis Center, Rollins College, and Mead Botanical Garden. This is a great opportunity to enjoy the lock and go Winter Park lifestyle without giving up space, convenience, or a little peace and quiet. Call to schedule your showing today!

700 Melrose Avenue Unit M23, Winter Park

918 Enclave Place, Winter Park
$2,125,000
5 Beds ⋅ 5 Baths ⋅ The Enclave Winter Park SubDv. ⋅ 32792 Zip Code
Pre-Construction. To be built. Buyer incentive - limited time - $50,000 cash credit at closing or $70,000 credit towards upgrades. The Hawthorn, an exceptional new custom residence by FG Schaub Custom Homes, located at 918 Enclave Place within The Enclave, a premier boutique community in the heart of Winter Park. Offering 5 bedrooms, 4.5 bathrooms, and 3,713 square feet of thoughtfully designed living space, this two-story home blends timeless architectural appeal, refined finishes, and a highly functional layout designed for modern living. The thoughtfully designed floor plan offers the convenience of a spacious first floor primary suite with a well-appointed bath and generous walk-in wardrobe, along with an additional first-floor guest suite with an en-suite bath. The open-concept kitchen, dining, and gathering areas create a natural flow for everyday living and entertaining, while the second floor provides three additional bedrooms, two full bathrooms, and a versatile gathering loft ideal for a media room, playroom, or additional living space. Designed to embrace Florida's indoor-outdoor lifestyle, the home features a covered lanai overlooking a private swimming pool and fully fenced backyard. The summer kitchen, complete with grill and refrigerator, creates an inviting setting for outdoor dining and entertaining. Throughout the home, elevated specifications and thoughtful details include high-performance, low-E double-pane windows, 8-foot solid-core interior doors, a tankless gas water heater, premium Wolf and Sub-Zero appliances, and designer-selected finishes with a curated palette of colors and materials. Every detail reflects the craftsmanship and quality synonymous with FG Schaub Custom Homes. The Enclave is an intimate collection of just 23 thoughtfully designed residences nestled beneath mature oak canopies. Ideally situated near Phelps Park, the YMCA, and multiple dining and shopping options, residents enjoy a charming residential setting with convenient access to downtown Winter Park's celebrated restaurants, boutiques, and cultural attractions. As a new home to be built, buyers have the opportunity to personalize select design finishes and explore certain floor plan modifications. Additional upgrade opportunities may include a detached cabana and/or guest house, subject to builder pricing, lot compatibility, and community guidelines. Experience the opportunity to create your dream home in one of Winter Park's most desirable locations, where architectural character, exceptional craftsmanship, and a connected lifestyle come together.

918 Enclave Place, Winter Park

100 S Interlachen Avenue Unit 401, Winter Park
$825,000
3 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code
Opportunity knocks at The Cloisters! This rarely available fourth-floor corner residence offers an exceptional opportunity to create a truly personalized home, with windows on four sides filling the interiors with abundant natural light and capturing desirable eastern exposures, perfect for viewing the sunrise and rocket launches. Also, enjoy tree top and lake views. Held by the same family since 1979, this residence offers more than 1,600 square feet of living space, this 3 bedroom - 2 bath unit is ready for its next chapter. While the interiors await updating, the generous floor plan provides a wonderful blank canvas with endless possibilities to reimagine the space and make it your own. Additional features include in-unit washer and dryer hookups, an assigned parking and storage closet and the unique privacy afforded by its corner location. Nestled along the shores of beautiful Lake Osceola, The Cloisters offers an exceptional lifestyle with an array of desirable amenities, including a sparkling swimming pool, boat slips, a private dock, two fitness rooms, a clubhouse, internet and cable, an on-site manager, and an outdoor grilling area. Ideally situated in the heart of Winter Park, this sought-after community is just a short stroll from The Alfond Inn, SunRail, and the charm of Park Avenue, where you can enjoy an inviting collection of sidewalk cafés, fine dining, boutique shopping, and the picturesque beauty of Central Park. Experience the best of Winter Park living in this exceptional lakefront community. Bring your designer, your vision, and your personal style to transform this special Cloisters residence into something extraordinary. Call today for your private viewing of this wonderful unit.

100 S Interlachen Avenue Unit 401, Winter Park

2823 Parkland Circle, Winter Park
$3,250,000
5 Beds ⋅ 6 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code
JUST COMPLETED NEW CONTRUCTION in the heart of Winter Park. Tucked away on a quiet cut-de-sac in an established neighborhood surrounded by beautiful newer residences, this nearly 4,500 square-foot home pairs thoughtful design with exceptional indoor-outdoor living. An impressive entry foyer sets the tone for a residence filled with designer details and and a floor plan featuring five en-suite bedrooms, six full baths, and the convenience of two laundry rooms to serve each floor. At the heart of the home, the chef's kitchen is appointed with Thermador appliances and designed for every day living and entertaining. Expansive living spaces are anchored by an indoor fireplace, and flow seamlessly to the covered lanai, where a second fireplace, fully equipped outdoor kitchen and private pool create an exceptional setting for year-round Florida living. Outdoor lush tropical landscaping and striking gas lanterns give the home a distinctive sense of arrival and timeless curb appeal. An oversized garage provides generous space for vehicles and storage, while integrated smart-home features including cameras, alarm, smart switches, and speakers with Sonos, bring modern convenience throughout. Zoned for sought-after Audubon Park School and Winter Park High School.

2823 Parkland Circle, Winter Park

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