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913 Moss Lane, Winter Park
$950,000
3 Beds ⋅ 2 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code
913 Moss Lane is in the Vias of Winter Park, on a tree-lined street in Maitland Shores. Neighborhood access to the Winter Park chain of lakes is a block away. Winter Park Racquet Club is a short walk. Park Avenue is a short drive. The home is zoned for Dommerich Elementary, Maitland Middle, and Winter Park High. The house is a 1953 split-level with 3 bedrooms, 2 baths, about 1,887 square feet, and a two-car garage. The main floor has the living room, dining area, kitchen, and Florida room. The bedrooms are upstairs. The 2023 renovation added new flooring, interior and exterior paint, a kitchen with white cabinetry, stone counters, and stainless appliances, and an updated bath with a walk-in glass shower. The backyard is fenced and has a patio. There is no homeowners association. This is a renovated three-bedroom in the Vias. See it for the street, the schools, and the lakes.

913 Moss Lane, Winter Park

2383 Sun Valley Circle Unit 2383, Winter Park
$234,900
2 Beds ⋅ 2 Baths ⋅ Cedarwood Village SubDv. ⋅ 32792 Zip Code
Don't miss your opportunity on this super clean 2 bed 2 bath Winter Park condo! Updated kitchen with White shaker cabinets, granite counters complete with all the appliances including washer and dryer. Formal dining room and family room with vaulted ceilings, skylights, along with a wet bar and cabinetry complimented by a centerpiece wood burning fireplace. Master bedroom features hardwood flooring along with updated vanity with granite counters along with a separate tub and shower. Secondary bedroom has laminate flooring along with updated vanity and granite countertops. Ceramic tile throughout the rest of the home as there is no carpet. French doors leading out to the oversized screen enclosed covered patio overlooking lush landscaping with no direct rear neighbor.  2 assigned parking spaces directly in front of the unit.There is also a small courtyard just outside the kitchen. Community features a recently remodeled pool, clubhouse and tennis courts. Winter Park location benefits include easy access to Full Sail University, UCF, Valencia College, Park Avenue filled with famous restaurants and boutique shopping.

2383 Sun Valley Circle Unit 2383, Winter Park

2410 Sherbrooke Road, Winter Park
$769,000
4 Beds ⋅ 3 Baths ⋅ Sherbrooke SubDv. ⋅ 32792 Zip Code
Welcome to 2410 Sherbrooke Rd in Winter Park! This spacious single-story home offers 2,141 sq ft of living space with 4 bedrooms, 2.5 bathrooms, and an attached two-car garage, all in a convenient location within walking distance of Winter Park High School. 10 minutes to Full Sail University, Rollins College, or Downtown Winter Park. Step inside to find generous living and family spaces filled with natural light, beautiful hardwood flooring, and a flexible layout designed for both everyday living and entertaining. The upgraded kitchen features granite countertops, abundant wood cabinetry, stainless steel appliances, recessed lighting, a center island, and a breakfast bar overlooking the family room. The spacious primary suite features new vinyl flooring and an updated en-suite bathroom with dual vanities and a large walk-in shower. Three additional bedrooms provide plenty of flexibility for guests, home office space, or other needs. An additional full bathroom, half bath, and dedicated laundry room complete the interior. French doors lead to the screened patio, offering a comfortable space for outdoor dining and relaxing. Beyond the patio is an exceptionally large backyard surrounded by mature trees and landscaping, with plenty of room for gardening, recreation, entertaining, or creating your own outdoor retreat. Major improvements include a ROOF REPLACED IN 2022 and A/C REPLACED IN 2022, giving the next owner added peace of mind. With its upgraded kitchen and bathrooms, spacious floor plan, beautiful flooring, huge backyard, screened patio, two-car garage, and recently replaced major systems, this Winter Park home offers an outstanding combination of space, comfort, and location. Schedule your private showing today and discover everything this home has to offer!

2410 Sherbrooke Road, Winter Park

825 Palmer Avenue, Winter Park
$5,195,900
5 Beds ⋅ 7 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code
Pre-Construction. To be built. A rare convergence of timeless French Country architecture, brand-new custom construction, and coveted access to the Winter Park Chain of Lakes. Thoughtfully designed and being built by FG Schaub Custom Homes, this exceptional property offers the character of a timeless estate with the amenities and craftsmanship expected in a luxury new construction home. The residence will feature five bedrooms, a dedicated office, five full bathrooms, and two half bathrooms, with beautifully appointed living spaces designed for both refined entertaining and comfortable everyday living. The striking exterior showcases classic French Country influences, stone accents, decorative brick detailing, crisp stucco, expansive windows, and multiple gabled rooflines, creating an elegant and welcoming architectural presence. Outdoor living is equally impressive, with a private pool and spa, covered outdoor living area with roll away screens, and a full summer kitchen creating a resort-style retreat. A brand-new private boathouse, included with the property, is positioned directly on the canal and provides access to the Winter Park Chain of Lakes, offering the opportunity to enjoy boating, water sports, fishing, and so much more. Final plans, specifications and finishes are subject to change.

825 Palmer Avenue, Winter Park

1773 Walnut Avenue, Winter Park
$2,725,000
5 Beds ⋅ 5 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code
Under Construction. Set within Winter Park’s highly sought-after Tree Streets, this exceptional new home delivers a sophisticated blend of architectural presence, refined interiors, and effortless indoor-outdoor living. A striking façade creates an unforgettable first impression, while a marble mosaic entry introduces the artistry and attention to detail found throughout the home. The main living space is designed to feel both impressive and inviting, centered around a dramatic electric fireplace wrapped in fluted stone. Expansive sliding glass doors fill the room with natural light and create a seamless connection to the outdoor entertaining areas. Open to the living room, the chef’s kitchen is a true statement, pairing richly veined Calacatta Gioia countertops with custom cabinetry, a built-in refrigerator, and a full suite of Thermador appliances. A generous walk-in pantry provides abundant storage and preparation space while maintaining the kitchen’s clean, elevated aesthetic.The first-floor primary suite offers a private retreat with vaulted ceilings and direct access to the backyard. Its spa-inspired bathroom is a sanctuary of beautifully selected marble tile and a serene, sophisticated color palette. A freestanding soaking tub, oversized walk-in shower, dual vanities, and thoughtfully curated finishes create an atmosphere reminiscent of a luxury resort. Also located on the main level is a versatile secondary bedroom that could serve beautifully as a private home office or guest suite, along with a well-appointed powder bath and a combined laundry and mudroom designed for everyday convenience. Upstairs, three additional guest suites provide comfort and privacy, while a spacious loft offers flexibility as a second living room, media space, or playroom. A second laundry room adds another layer of functionality to the thoughtfully planned layout. Outside, the home continues to impress with a covered lanai and full summer kitchen, creating the perfect setting for year-round entertaining. A marble pool deck surrounds the sparkling pool and spa, while the spacious backyard offers room to relax, gather, and enjoy the Central Florida lifestyle in complete comfort. The location is what really sets this home apart. New construction opportunities are becoming increasingly rare within the up-and-coming Tree Streets, making this residence an especially compelling offering. Just a short walk from the Winter Park YMCA, Phelps Park, and Interlachen Country Club, the home places recreation and everyday conveniences close at hand. Hop on your golf cart and arrive to Park Avenue's boutiques, cafes, and restaurants within minutes. A home of this caliber in such a coveted location is a rare find and it won’t remain available for long.

1773 Walnut Avenue, Winter Park

2622 Lake Howell Lane, Winter Park
$3,750,000
4 Beds ⋅ 3 Baths ⋅ Acreage & Unrec SubDv. ⋅ 32792 Zip Code
Welcome to an extraordinary private lakefront retreat in Winter Park, where expansive grounds, exceptional amenities, and breathtaking Lake Howell views come together in one special property. Set behind a private gated entrance on approximately 4.3 total acres, with roughly half of the property consisting of dry land and the balance extending into Lake Howell, this remarkable estate offers a rare combination of privacy, space, and direct lake access, yet remains just minutes from the charm of Park Avenue, Interlachen Country Club, shopping, dining, and everything Winter Park has to offer. Lake Howell provides a spectacular backdrop for everyday living and entertaining, with opportunities for boating, fishing, water sports, sunset cruises, and unforgettable days on the water. The property features its own private boat ramp, boathouse, and boat dock, making lake life exceptionally convenient. The grounds are designed for both grand entertaining and relaxed family living. A massive detached barn offers an incredible flexible space for private events, parties, gatherings, game nights, or simply creating your own ultimate entertainment venue. Fully air conditioned and featuring high ceilings, the barn provides room for additional vehicles, RVs, boats, recreational equipment, and more. It also includes a private gym and bathroom, making it a versatile addition to the property. For RV enthusiasts, the property features a full 50 amp RV hookup with water and sewer hookups. The property is Agriculture zoned and allows horses. A separate four-car detached garage with workshop provides substantial storage and workspace. A generator adds convenience and peace of mind. The expansive fenced grounds offer plenty of room for family, pets, recreation, and outdoor activities, including a large playset and a firepit with comfortable seating—the perfect setting for cool evenings, roasting marshmallows, sharing stories, and making memories together. The recently updated pool area is designed to feel like your own private resort. Enjoy the covered lanai, outdoor kitchen, pool, and stunning lake views, along with a gas fireplace that creates an inviting atmosphere for evening entertaining. The outdoor kitchen is a chef’s dream, making it easy to host everything from casual family gatherings to unforgettable waterfront celebrations. Inside, the home was thoughtfully renovated in 2016 and offers just over 3,377 square feet under air, with approximately 7,758 total square feet. Beautiful wood flooring, tile, and carpeted bedrooms create a comfortable blend of style and functionality. The Florida room provides the perfect place to relax, take in the lake views, and enjoy the natural beauty surrounding the home. The upgraded kitchen features stainless steel appliances and a Thermador range, while the spacious executive office provides an ideal work-from-home environment or private study. The residence offers four bedrooms and three bathrooms, providing generous accommodations for family and guests. With multiple indoor and outdoor gathering spaces, extraordinary storage, recreational amenities, and direct access to Lake Howell, this property is much more than a home—it is a private lifestyle estate. Whether you're looking for a peaceful waterfront sanctuary, a place to entertain on a grand scale, a family compound, or simply a rare piece of Winter Park property with exceptional lake access, this property delivers an unparalleled opportunity.

2622 Lake Howell Lane, Winter Park

698 N New York Avenue, Winter Park
$5,995,000
5 Beds ⋅ 6 Baths ⋅ Greens/Pk SubDv. ⋅ 32789 Zip Code
Brand new 2026 custom residence in the heart of downtown Winter Park, just completed and showcasing elevated finishes thoughtfully curated by FG Schaub Construction & SOCO Interiors. Positioned across from the seventh green of the Winter Park 9 Golf Course, this exceptional five-bedroom, five-and-one-half-bath home includes a dedicated office, plus upstairs lounge in offering an extraordinary combination of sophisticated design, exceptional craftsmanship, and an unparalleled location. A striking front entry, framed by steel & glass doors open to a dramatic two-story foyer, where a floating glass-railed staircase sets the tone for the home’s contemporary aesthetic. The front-corner office features expansive windows overlooking the Winter Park 9 Golf Course. The overall living design is an open-concept floor plan that creates effortless connectivity between the living, dining areas and kitchen. Designed for the discerning chef, the kitchen features Wolf and Sub-Zero appliances, including a six-burner gas range, integrated refrigeration, wine storage, a generous waterfall island with seating, and a spacious walk-in pantry. The adjacent living areas are anchored by a custom wet bar with ice maker and two wine towers, an linear electric fireplace, and a wall of disappearing glass sliders that seamlessly connect the interior to a fully enclosed 600+ square-foot, air-conditioned lanai outfitted with a complete summer kitchen. The expansive indoor/outdoor lanai provides an exceptional setting for year-round entertaining that opens up via three additional sets of glass panel doors or automatic screens to the pool and outdoor oasis. The 633sf lanai has its own dedicated HVAC system however, is NOT included in the home’s primary heated & cooled living area square footage of 5,096sf. Privately positioned on the first floor, the luxurious primary suite features a wall of glass with direct access to the outdoor living area and an outdoor shower. The spa-inspired primary bath includes a freestanding soaking tub, glass-enclosed shower, generous size custom walk-in closet, and private sauna. Transition upstairs by either elegant staircase or elevator a spacious lounge area/loft and three additional bedroom suites, each offering a walk-in closet and ensuite bath. A versatile flex room with dedicated bath and a walk-in closet can easily serve as a fifth bedroom. A full hall bath and second-level laundry room (note: there is also a first-level laundry rm) provide additional convenience. Outside, a heated saltwater pool and spa, three pool side fire bowl features, outdoor private shower, and meticulously landscaped grounds create a sanctuary to relax and unwind... An exceptional opportunity to experience refined urban living in one of Winter Park’s most coveted settings, with the tranquility of a golf course backdrop to being in the downtown Park Avenue corridor. Stroll to renowned boutiques, award-winning restaurants, sidewalk cafés, Central Park, the Saturday Farmers Market, art museums, The Alfond Inn, and the many cherished events and traditions that make downtown Winter Park living so special!

698 N New York Avenue, Winter Park

436 N Wymore Road, Winter Park
$1,350,000
Killarney Circle SubDv. ⋅ 32789 Zip Code
Prime Winter Park commercial office building with visibility of monument signage from 1-4 East bound traffic and Ideally situated on Wymore Road. This 2018 built one story office building offers Low-maintenance ownership, with approximately 3021 total square feet, creating a professional office environment with flexible layout options for investors or owner-users. The property features 10 parking spaces includes one handicap with public street parking option located in 32789. Both suites have separate entrances, with access door in between, both with reception areas, open air built-in workspaces. Each suite has its own kitchen and bathroom facilities. Building has 6 total private offices, ( 4 & 2) providing convenience for both administrative and operational functions. Well-constructed, high ceilings, attractive flooring, 2 conference rooms with high-end lighting fixtures, window treatments. Both suites are leased, generating $9,678.60 per month with the tenants' paying utilities, alarm, housekeeping, building taxes, and insurance. One of the tenants' leases (1736 Sq foot suite) expires September 1, 2029 (rental income increases every year) The other suite (1285 sq ft) lease is owner occupied and available for rent immediately or owners are willing to stay up for up to seven months based on new owners' situation. This property offers an excellent opportunity for an owner-occupant of one suite while obtaining rental income. The property manager is the listing RE Agent/seller who will provide a smooth transition upon closing. This property is a prime opportunity for businesses seeking a high-quality, move-in-ready or flex space in one of the area's most accessible commercial corridors.

436 N Wymore Road, Winter Park

200 S Interlachen Avenue Unit 350, Winter Park
$2,350,000
3 Beds ⋅ 4 Baths ⋅ Versailles Winter Park Condo SubDv. ⋅ 32789 Zip Code
Welcome to The Versailles of Winter Park, an extraordinary opportunity to own one of only seven exclusive private residences in one of Winter Park's most coveted luxury communities, nestled just steps from the world-renowned Park Avenue and adjacent to the prestigious Alfond Inn & Spa. This magnificent third-floor residence offers 3,110 square feet of impeccably designed one-level living, oak hardwood floors throughout, elegant crown molding, and an abundance of natural light pouring through French doors set the tone for refined sophistication. Entertain effortlessly in the grand living area with a sprawling balcony adorned with Chicago brick and stone railing. Kitchen includes wood cabinet, granite, Monogram refrigerator, convection oven and microwave. The versatile split-bedroom floor plan ensures ultimate privacy, with the lavish primary suite accessed through double doors, walk-in closet, private balcony access, and an opulent spa bath featuring dual vanities, a soaking tub, walk-in shower. A designated office with wall-to-wall built-ins, a formal dining room accommodating up to twelve guests, a private two-car garage, and meticulously maintained landscaping. The Versailles of Winter Park is the ultimate expression of luxury living offering an unparalleled lifestyle just moments from the finest dining, boutique shopping, art festivals, and cultural events that makes Winter Park one of Florida's most desirable destinations.

200 S Interlachen Avenue Unit 350, Winter Park

2275 Island Run, Winter Park
$279,999
3 Beds ⋅ 2 Baths ⋅ Windward Square Sec 3 SubDv. ⋅ 32792 Zip Code
Great opportunity in the established Windward Square community of Winter Park! This END-UNIT home offers 3 bedrooms, 2 full bathrooms and approximately 1,467 square feet of living space, with added privacy and plenty of potential. ROOF REPLACED IN 2017! 10K seller contribution for the floor. The home is ready for some TLC and personal updates, giving the next owner the opportunity to renovate and make it their own. The spacious living and dining areas gives a functional layout, while the large screened porch provides additional space to relax, entertain, and enjoy Florida living. Being located at the end provides additional privacy and a more open feel compared with interior units. The community offers amenities including a swimming pool and tennis courts. Conveniently located near shopping, dining and major roadways, with easy access to Winter Park, Orlando and surrounding areas. Whether you’re looking for a primary residence or an investment opportunity, this property offers great potential and an excellent opportunity to add value through your own improvements. Bring your vision and make this home your own!

2275 Island Run, Winter Park

508 Brechin Drive, Winter Park
$599,000
3 Beds ⋅ 2 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32792 Zip Code
Renovated and move-in ready, this updated Winter Park home offers a fresh, modern interior without the hassle of renovations. The brand-new kitchen features new cabinetry, quartz countertops and all new appliances, while both bathrooms have been fully renovated with new finishes and fixtures. New luxury vinyl plank flooring runs throughout the home, complemented by fresh interior paint. The roof was replaced in April 2022, providing added peace of mind for today's buyer. With 3 bedrooms, 2 bathrooms and approximately 1,785 square feet of living space, this home offers a comfortable and functional floor plan in an established Winter Park location. The spacious yard offers plenty of room for outdoor enjoyment and the opportunity to create your own ideal landscaping. Enjoy easy access to Cady Way Park and the Cady Way Trail, perfect for walking, biking and recreation. Just minutes from the restaurants, shopping and charm of Park Avenue, as well as the popular Baldwin Park area. Conveniently located near AdventHealth Winter Park and numerous dining, shopping and recreational options. Agent owned property.

508 Brechin Drive, Winter Park

1922 Hammerlin Avenue, Winter Park
$1,095,000
3 Beds ⋅ 3 Baths ⋅ Edgewood Sub SubDv. ⋅ 32789 Zip Code
WELCOME TO CONTEMPORARY LUXURY IN THE HEART OF WINTER PARK! This stunning two-story pool residence has been beautifully remodeled from top to bottom and offers high end design, high-end finishes and an exceptional lifestyle location near East End Market, Baldwin Park, Audubon Park and all of Winter Parks charm. Behind the private gated courtyard and modern fencing, discover a thoughtfully designed home featuring custom built-ins, designer finishes, porcelain tile, custom wood-plank stairs and a dramatic modern glass railing. The beautifully appointed kitchen is designed for both entertaining and everyday living and features premium Wolf gas cooking appliances with range hood, Sub-Zero refrigerator, stainless steel wine refrigerator, microwave, stainless farmhouse sink, pantry and stylish pendant lighting. The open living areas provide a wonderful setting for gathering and entertaining. The downstairs primary suite offers convenience, privacy and direct access to the spectacular outdoor pool living area. The luxurious en-suite bath features dual vanities, custom cabinetry and mirrors, high-end designer fixtures, beautiful tile work and a spacious glass-enclosed shower. Upstairs, you will find generously sized bedrooms, custom closet spaces and a beautifully finished bonus room offers exceptional flexibility for a home office, fitness room, exercise space, storage or additional flex space. Additional features include a dedicated first floor laundry room and powder room, upstairs linen closet, designer lighting through out and a two-car garage. Step outside to your own private retreat! The covered lanai flows seamlessly to the beautiful custom pool and outdoor entertaining area featuring a gas fire pit. Mature bamboo landscaping, a fenced yard and contemporary entrance fencing create a private and inviting setting. LOCATION, LOCATION, LOCATION! Enjoy the highly desirable Winter Park lifestyle with convenient access to East End Market, local coffee shops, exceptional restaurants, specialty shopping, markets and community events. Nearby destinations include Leu Gardens, Baldwin Park, Park Avenue and Downtown Winter Park. Zoned for Audubon Park School (K-8) and Winter Park High School; buyers should verify school assignments and enrollment eligibility. This exceptional move-in-ready home combines contemporary luxury, resort-style outdoor living and one of Central Florida’s most desirable lifestyle locations!

1922 Hammerlin Avenue, Winter Park

500 N Pennsylvania Avenue Unit G, Winter Park
$349,500
2 Beds ⋅ 1 Baths ⋅ Village Condos SubDv. ⋅ 32789 Zip Code
Virtually Staged. LOCATION, LOCATION, LOCATION in Winter Park!!! **Rare opportunity to own in the highly desired Downtown of Winter Park for under $350,000!** Enjoy the highly desired downtown Winter Park lifestyle with Park Avenue’s boutiques, restaurants, cafés, arts and culture, Rollins College, the Winter Park Train station, Casa Feliz, seasonal festivals and community events all just a short walk from your front door. This charming 2-bedroom, 1-bath condo offers an inviting open-concept living and dining area, along with a kitchen featuring granite countertops and convenient counter seating. Condo is highlighted with beautiful plantation shutters. Located within a charming, intimate condominium community, it offers a wonderful combination of comfort, location and low-maintenance living, all within an area known for its highly regarded Winter Park-area schools. Whether you’re searching for a primary residence, a second home, a great option for downsizing, or an investment property, this is your opportunity to own a piece of one of Central Florida’s most desirable cities. Imagine strolling to dinner on Park Avenue, meeting friends for coffee, walking to Rollins College, enjoying the beauty and history of Casa Feliz, browsing the shops, attending an art festival or catching the train — all without worrying about finding a parking space. Simply walk out your front door and enjoy the incredible lifestyle that makes Winter Park such a special place to call home. **Opportunities to own downtown Winter Park real estate at this price point are rare. Don’t miss your chance — schedule your private showing today before this one is sold. A location and lifestyle like this won’t last long!**

500 N Pennsylvania Avenue Unit G, Winter Park

3020 Nicholson Drive, Winter Park
$470,000
4 Beds ⋅ 2 Baths ⋅ Wrenwood Unit 3 3rd Add SubDv. ⋅ 32792 Zip Code
UPDATED 4-BEDROOM POOL HOME IN WINTER PARK WITH NO HOA! Welcome to 3020 Nicholson Drive, a beautifully updated 4-bedroom, 2-bath home with a private pool, 2-car garage, and NO HOA, tucked into the established Wrenwood neighborhood of Winter Park. From the thoughtfully updated interior to the backyard designed for Florida living, this home offers the space, flexibility, and location you've been looking for. Step inside to a bright and inviting interior featuring new LVP flooring throughout, a split-bedroom floor plan, and multiple living and dining spaces that provide plenty of room to spread out, gather, and entertain. The kitchen features abundant cabinetry and counter space, stone countertops, a built-in oven and cooktop, and a window overlooking the backyard. Custom epoxy flooring in the kitchen and entry adds durability and a unique finishing touch. The primary suite is one of the home's standout spaces, featuring a beautifully remodeled bathroom with a double vanity and an oversized glass-enclosed shower, along with a custom-built closet with shelving and organization designed to maximize storage and functionality. But the backyard may be where you'll want to spend most of your time. Step outside to a private in-ground pool, covered screened patio, fenced backyard, and an expanded pool deck with additional pavers, creating multiple spaces to lounge, entertain, dine outdoors, or simply enjoy the Florida sunshine. There's even green space beyond the pool, giving the backyard a more open feel than you might expect from a pool home. The home also offers important improvements already completed for you, including a roof replaced in 2019, re-pipe completed in 2013, and HVAC system replaced in 2018/2019. A professionally installed security system and security cameras add another layer of functionality. The location ties it all together. Situated in Winter Park's Wrenwood neighborhood, 3020 Nicholson Drive puts you within easy reach of some of Central Florida's favorite destinations, including Park Avenue, Winter Park Village, and Baldwin Park, with shopping, dining, entertainment, and everyday conveniences nearby. Convenient access to SR 436 and the 408 also makes it easy to reach Downtown Orlando and destinations throughout Central Florida.

3020 Nicholson Drive, Winter Park

1850 Bryan Avenue, Winter Park
$699,000
3 Beds ⋅ 2 Baths ⋅ Lakeview Terrace SubDv. ⋅ 32789 Zip Code
Tucked beneath mature oak trees, 1850 Bryan Avenue is a well-maintained home offering comfortable single-story living in Winter Park. Natural light and warm wood floors flow through the inviting living and dining spaces, while a flexible bonus room is well suited for a home office, den or creative space. The kitchen features wood cabinetry and ample counter space. The spacious primary suite offers a private retreat. Additional features include an indoor laundry room and an attached two-car garage. Outside, the fenced yard provides a peaceful setting for gardening, entertaining or relaxing beneath the trees. With shopping, dining, parks and other Winter Park amenities nearby, this home brings together character, comfort and a desirable location.

1850 Bryan Avenue, Winter Park

702 Via Bella, Winter Park
$4,090,000
4 Beds ⋅ 6 Baths ⋅ Palmer Ave Lakeside Prop SubDv. ⋅ 32789 Zip Code
Completed in 2025 by Floridian Custom Homes, this distinguished English cottage-inspired residence brings refined character, thoughtful design, and exceptional craftsmanship to one of Winter Park’s coveted residential corridors. Encompassing 3,720 square feet, the four-bedroom, five-and-one-half-bath home blends sophisticated interiors with contemporary systems and inviting spaces designed for both everyday living and entertaining. "OPTION TO PURCHASE HOME TURN-KEY": Owner has just finished a ~ $500,000 complete furnishings install thru Brianna Michelle Interior Design! A solid mahogany front door opens to interiors defined by Botticino limestone flooring with a distinctive textured finish, bespoke millwork, and generous gathering spaces. Coffered ceilings and recessed WAC lighting add architectural dimension, while insulated casement windows fill the home with natural light. The expansive central living area flows seamlessly into the dining space and beautifully appointed kitchen, featuring custom cabinetry by Grit & Grain, leathered Taj Mahal quartzite countertops, and a remarkable collection of professional-grade appliances, including a 43-inch La Cornue gas range with McGurken hood, Thermador refrigerator and freezer columns, and Bosch dishwasher. A generously sized walk-in pantry continues the custom cabinetry and quartzite finishes while incorporating dual refrigeration drawers and a dedicated ice maker. The adjacent mudroom is outfitted with substantial hardwood built-ins, providing exceptional organization and storage. The first-floor primary suite occupies a private wing and showcases wide-plank European white oak flooring by Forrest Accents, a customized walk-in closet, and an elegant spa-inspired bath. Natural stone countertops, Rohl polished nickel fixtures, marble flooring and shower surfaces, and a frameless glass enclosure create a polished yet inviting retreat. Throughout the home, solid-core doors are complemented by Emtek hardware. Positioned near the front entry, the library offers a sophisticated setting for work or quiet reflection, with matching oak flooring and custom casement windows. A solid wood staircase ascends to a second living area with an adjoining lounge or flex space. Three additional bedroom suites provide private accommodations, each with en-suite baths featuring porcelain flooring, frameless glass showers, brushed quartz and dolomite vanities, designer lighting, and integrated closet systems. Modern infrastructure includes CAT-5/6 wiring, Sonos-integrated speakers, Lutron RA-3 smart lighting controls, and pre-wiring for home security with digital camera ports strategically located at key entry points. Multiple access points from the primary suite and kitchen wing extend to a beautifully enclosed outdoor environment framed by mature landscaping designed by Signature Landscape. A Roman-inspired cabana with soaring ceilings and exposed beams serves as the centerpiece for outdoor entertaining. The fully tiled saltwater pool, representing a $50,000 upgrade, features therapy jets, LED-lit bubblers, a dual-skimmer system, Jandy heat-pump automation, and a Paramount self-cleaning system. Minutes to vibrant shopping, restaurants, sidewalk cafes of Park Avenue, and all that downtown Winter Park has to offer.

702 Via Bella, Winter Park

751 Pansy Avenue, Winter Park
$1,875,000
3 Beds ⋅ 4 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code
Set along one of Winter Park’s charming brick streets just steps from Park Avenue, this beautifully maintained home pairs refined design with an exceptional location. Impressive curb appeal sets the tone, while thoughtfully curated interiors create a home that feels both elevated and inviting. Inside, the main living space centers around a custom entertainment wall with built-in shelving and an electric fireplace. The adjoining kitchen is equally impressive, featuring quartz countertops, a statement La Cornue range, paneled refrigerator, and a cleverly hidden walk-in pantry. A sun-filled breakfast nook provides a casual dining space, while sliding glass doors create a seamless connection to the outdoor living areas. For larger gatherings, the spacious formal dining room offers an elegant setting for entertaining, and a well-designed mudroom and laundry combination adds everyday functionality. The primary suite is a private retreat with generous proportions and a beautifully appointed spa-inspired bath. A custom trough-style sink, separate makeup vanity, oversized walk-in shower, freestanding soaking tub, and expansive walk-in closet create a space that feels luxurious yet highly functional. Two additional bedrooms are both ensuite, offering privacy and comfort for family and guests. Outdoors, the home truly impresses. A lush wall of mature bamboo surrounds the backyard, creating an unexpected sense of privacy just moments from the heart of Winter Park. The resort-style pool features a sun shelf and built-in seating, while a pergola provides the perfect setting for al fresco dining and relaxed evenings outdoors. For the car enthusiast there is a car lift in the garage allowing for storage of up to 3 vehicles. The location is difficult to match, just steps from the shops, restaurants, and energy of Park Avenue and minutes from Hannibal Square, Winter Park Village, Park Maitland School, and the Enzian Theater. Beautifully maintained, thoughtfully designed, and positioned in one of Winter Park’s most desirable locations, this is a rare opportunity to enjoy an exceptional lifestyle in the heart of it all.

751 Pansy Avenue, Winter Park

222 Lewfield Circle, Winter Park
$189,900
2 Beds ⋅ 2 Baths ⋅ Stratford A Winter Park Condo SubDv. ⋅ 32792 Zip Code
One or more photos was virtually staged. This 2 Bedroom, 2 Bath, 953 SF Winter Park condo in the amazing Stratford community offers a comfortable, functional floor plan complemented by fresh interior paint, updated flooring, and a 2026 HVAC system. The spacious living area features a ceiling fan and sliding glass doors that bring in natural light and open to a covered balcony, creating an easy extension of the indoor living space. The adjacent dining area provides flexibility for everyday meals or additional living space. The kitchen features wood cabinetry, generous counter space, tile flooring, and stainless steel refrigerator, while an in-unit laundry closet adds everyday convenience. Bedrooms feature updated flooring, neutral finishes, ceiling fans, and ample natural light. A large walk-in closet with extensive shelving and storage helps keep everything organized, while the bathroom includes a tiled walk-in shower and vanity storage. Freshly touched up throughout and offering a practical layout with comfortable living spaces, this Winter Park condo is ready for its next chapter.

222 Lewfield Circle, Winter Park

276 Detmar Drive, Winter Park
$3,600,000
4 Beds ⋅ 5 Baths ⋅ Detmar Terrace Winter Park SubDv. ⋅ 32789 Zip Code
Tucked away in the heart of Winter Park, this custom-built residence seamlessly blends modern luxury with the comfort of everyday living. Thoughtfully designed with exceptional attention to detail, the home offers clean, contemporary interiors balanced by beautiful architectural elements, and abundant natural light. The main level offers two bedrooms and three full bathrooms, including a primary suite with a versatile bonus room behind French doors—perfect for a private office, gym, or additional bedroom. The ensuite features two walk-in closets, a double sink vanity, a large rainfall shower, and a soaking tub. The open-concept floorplan features a beautifully appointed kitchen with high-end appliances and custom cabinetry, flowing seamlessly with the dining area and the spacious living room, where a gas fireplace creates a welcoming gathering space. Architectural light wood ceiling beams, plantation shutters, and expansive glass sliders frame beautiful views of the outdoor living area. Upstairs, two additional bedrooms each feature private ensuite baths and balconies, complemented by a kitchenette and additional living space. This flexible layout is ideal for multigenerational living, guests, live-in staff, or simply creating a private retreat within the home. Designed for effortless indoor-outdoor living, the entire downstairs opens to a private backyard oasis featuring a sparkling saltwater pool, lush bamboo backdrop, summer kitchen, gas fireplace, and outdoor shower. The covered lanai is equipped with automatic screens, creating an inviting and comfortable space to enjoy the outdoors year-round. Beyond its sophisticated design, the home offers exceptional functionality, including an oversized two-car garage pre-wired for EV charging, whole-home surround sound, hurricane-impact windows, a whole-house Generac generator, indoor built-in sprinkler system, dual laundry rooms, and enhanced insulation for exceptional peace and quiet. The entire first floor is completely wheelchair accessible. Tastefully furnished and offered with all furnishings, this exceptional residence presents a rare combination of refined design, thoughtful functionality, and classic Winter Park charm. Ideally located just one mile from Park Avenue and minutes from Winter Park’s renowned restaurants, shops, hospitals, schools, and scenic Lake Osceola, this is a home designed for both elevated living and everyday comfort.

276 Detmar Drive, Winter Park

7605 Aloma Pines Court, Winter Park
$349,000
3 Beds ⋅ 3 Baths ⋅ Aloma Trails SubDv. ⋅ 32792 Zip Code
Virtually Staged! Amazing Townhome! GATED Community of Aloma Trails Townhomes in a great Winter Park location, 3 bedroom, 2.5 bathroom with features of spacious living and comfortability. This stunning Townhome has Ceramic Tile flooring throughout the first floor leads to a kitchen with all the upgrades including SS appliances. 42” Cabinets, upgraded granite countertops and backsplash, and an island with plenty of seating along with a carpet in the second floor and all bedrooms. The master suite is outfitted with large Walk-In closet, glass-enclosed shower with dual sinks, and oversized cabinets. The two additional bedrooms share a second full bath and there is a half bath on the main floor convenient for guests. Separated interior laundry closet provides convenience and comfort. A nice big Car Garage and driveway, which will easily suit for multiple vehicles as necessary. This community comes with hassle-free lawn care, and well-maintained common areas and a BEAUTIFUL location. The fitness enthusiast will enjoy the Crunch Fitness facility just across the community and, the CADY WAY trail and the CROSS SEMINOLE trail- all just steps away from your front door. Walmart, Costco and Publix are almost 3 min driving distance. Close to Park Ave in Winter Park, SR 417, UCF, Fulsail University, and just 40 minutes to the Beach! Add in top notch Seminole County Schools. You don't need to look any further for your Dream Home! Schedule your viewing today! Note: Some of the pictures are showing the virtual staging of the unit and the furnitures/decorative items are not included to the listing.

7605 Aloma Pines Court, Winter Park

900 Carver Street, Winter Park
$659,000
3 Beds ⋅ 3 Baths ⋅ Magnolia Gardens Sub SubDv. ⋅ 32789 Zip Code
Completely Renovated | Move-In Ready | Single-Story Living. A comprehensive renovation brings modern finishes and functionality to this Winter Park home, with a redesigned kitchen that opens to the main living area. The kitchen features 42-inch shaker cabinetry, Calacatta quartz countertops, stainless steel appliances, a center island, and pantry storage. Luxury vinyl flooring extends through the main living areas, complemented by recessed LED lighting and updated fixtures. A complete interior renovation and landscaping updates were completed in 2026, complementing major improvements from 2019, including a new roof, HVAC system, and double-pane windows. The three-bedroom, three-bathroom layout includes two spacious en-suite bedrooms, with all bathrooms completely remodeled. Additional features include an interior laundry closet and a fully fenced backyard. Outside, paver walkways, manicured lawns, and refreshed landscaping complement the home's updated exterior. Located in Magnolia Gardens with no HOA, the property offers convenient access to Park Avenue's restaurants, boutiques, and farmers market, as well as Lake Lily, Maitland City Centre, and I-4.

900 Carver Street, Winter Park

623 Grenadine Court Unit 623, Winter Park
$194,900
2 Beds ⋅ 2 Baths ⋅ Winter Park Villas Condo SubDv. ⋅ 32792 Zip Code
PRICE ADJUSTMENT! Welcome to this Desirable Winter Park Villas Condo FIRST FLOOR 2 BEDROOM, 2 FULL BATH, 1037 square feet, featuring NEW AIR CONDITIONING SYSTEM and BRAND NEW CARPET freshly installed! EXCELLENT LOCATION walking or bike riding distance to FULL SAIL UNIVERSITY and easy access to UCF! Ideally located in rear of community with ample open parking. Your spacious Kitchen features ample counter space and abundant cabinetry, kitchen sink window with view of front door entry and parking area. Kitchen has a closet pantry and there is an opening to Dining Room with Bar Seating area. Dining Room has views to backyard and a Wet Bar with unique Sink Closet feature. Family Room has a fireplace and views of outside greenery. In hallway off entry is your Washer/Dryer closet and they are both included in the sale. The Primary Bedroom is large with walk in closet, full bathroom with tub shower combo and two vanities. The Secondary Bedroom features back yard views and built in closet and easy access to hallway full second bath. Outside you'll love the covered patio and lawn area for lounging or gardening outside. Off the patio is a storage closet for the Water Heater. Winter Park Villas amenities include community pool, fitness center and tennis courts. Seller is offering a One Year Assurant Home Warranty covering all the appliances included. Located in Winter Park School District and easy access to Orlando International Airport! Call for to see it today, priced under $200,000 location can't be beat! Property may be under audio/visual surveillance.

623 Grenadine Court Unit 623, Winter Park

720 Pansy Avenue, Winter Park
$1,295,000
3 Beds ⋅ 4 Baths ⋅ Villa View Park SubDv. ⋅ 32789 Zip Code
Welcome to 720 Pansy Ave, a distinctive three-story Winter Park home thoughtfully designed for both everyday living and flexible use. Fully remodeled in 2017, the residence offers a clean, contemporary interior with LVP and tile flooring, recessed lighting, crisp finishes, and an open flow through the main living spaces. The first floor includes a spacious living room, dining area, and a separate office/study/den, providing plenty of room to work, gather, and unwind. At the heart of the home, the modern kitchen features sleek white cabinetry, stainless steel appliances, generous storage, and a wide pass-through that keeps the kitchen connected to the dining and living areas. The first-floor primary suite offers the convenience of main-level living, complete with a walk-in closet and a beautifully finished primary bath featuring a steam shower. Large windows bring natural light into the home, while the neutral finishes create an easy backdrop for a variety of styles. Upstairs, two additional bedrooms are joined by flexible spaces that add to the home’s functionality, including a dedicated storage room on the second floor. Continue to the third level to find an expansive bonus space that can easily serve as a media room, game room, creative studio, home gym, or additional lounge. Practical features include a durable metal roof and a whole-house generator designed to keep the home powered during storms and unexpected outages, providing added comfort and peace of mind. Outside, the private backyard extends the living space with decking, a hot tub, landscaped green space, mature trees, and a gazebo for relaxing or entertaining. The location completes the package, placing you in the heart of the Winter Park lifestyle with convenient access to Park Avenue, known for its boutiques, restaurants, cultural attractions, and community events, as well as nearby Rollins College. Enjoy the character and charm of an established Winter Park neighborhood while remaining close to the shopping, dining, arts, and everyday conveniences that make this area such a desirable place to call home.

720 Pansy Avenue, Winter Park

2857 Clever Lane, Winter Park
$394,500
3 Beds ⋅ 3 Baths ⋅ Grayson Square SubDv. ⋅ 32792 Zip Code
Talk about VALUE! Almost brand new and move in ready CORNER townhome in Winter Park! This beautiful 3 bedroom 2.5 bathroom home with just under 1,800 sq. ft. offers a large 2 car garage, light and bright living spaces, clean and modern designer features, and comes equipped with a full kitchen appliance package and washer/dryer. The first floor offers expansive living spaces with enough room for a dining area and family room. All of which flow seamlessly into the open kitchen. With white cabinets and Quartz counter tops, the kitchen is a show stopper! The entire first level is adorned with tile and offers a half bathroom and access to the covered back porch. Just up the stairs, you will find all of your bedrooms and full bathrooms. The primary bedroom and en suite bathroom are ample in size and also offer a large walk in closet. Both secondary bedrooms are down the hall and share a large full bathroom. The small gated community of townhomes offers a community pool and serene pond. HOA includes cable! Make sure to put this on your must see list!

2857 Clever Lane, Winter Park

1278 S Pennsylvania Avenue Unit 13, Winter Park
$799,000
3 Beds ⋅ 3 Baths ⋅ Casa Jardin Condo SubDv. ⋅ 32789 Zip Code
In the heart of Winter Park’s coveted Virginia Heights neighborhood, just moments from the boutiques, dining, and charm of Park Avenue and the green spaces of Seven Oaks Park, this exceptional Mediterranean-inspired end-unit condominium offers an unparalleled blend of elegance, comfort and accessible convenience. Encompassing nearly 2,000 square feet, the residence features three bedrooms, two-and-a-half baths and a thoughtfully designed floor plan that lives like a private home. Bathed in natural light, the interiors are framed by expansive window walls and floor-to-ceiling glass doors that create a bright, airy ambiance throughout. Architectural details including graceful arched passageways, column-lined hallways, and a custom wrought-iron spiral staircase add timeless character and sophistication. Beautifully updated and meticulously maintained, every room reflects a sense of warmth and refinement. The spacious primary retreat is a sanctuary, featuring soaring cathedral ceilings, dual walk-in closets and a spa-inspired bath designed for relaxation. Two additional bedrooms offer versatility for guests, family or a home office. The open-concept living and dining areas are enhanced by travertine and luxury vinyl plank flooring, coffered ceilings, designer lighting, and a beautifully appointed chef’s kitchen complete with solid wood cabinetry, granite countertops, a center island and generous walk-in pantry. French doors open to a freshly painted screened courtyard, creating a private outdoor escape ideal for entertaining or quiet evenings at home. Above, the freshly painted rooftop terrace provides a spectacular setting for alfresco dining, sunset gatherings or simply enjoying Florida’s year-round sunshine. Additional features include a powder bath, plantation shutters, ceiling fans throughout, an oversized two-car garage, and a third-floor walk-in attic offering abundant storage and exciting future expansion possibilities. Residents of Casa Jardin enjoy a beautifully refreshed community, recently enhanced with a new roof, exterior paint and professional landscaping. Ownership also includes exclusive access to Lake Virginia and renowned Winter Park Chain of Lakes through College Point, featuring a private lakefront gathering area along with kayak and paddleboard storage. Ideally near Azalea Lane Recreation Center, the Winter Park Tennis Center, Orange Avenue’s popular restaurants and shops, and top-rated schools, this remarkable residence offers a rare opportunity to enjoy one of Central Florida’s desirable lifestyles.

1278 S Pennsylvania Avenue Unit 13, Winter Park

1287 Verdant Glade Place, Winter Park
$735,000
4 Beds ⋅ 4 Baths ⋅ Meadows At Hawks Crest SubDv. ⋅ 32792 Zip Code
Virtually Staged. Gated Community | Dual Primary Suites | Main-Level Living | Located in Winter Park’s gated Hawks Crest community, this two-story home pairs a spacious open floor plan with a private backyard setting and a layout that offers exceptional versatility. The main level includes the primary suite, dedicated study, laundry room, kitchen, and principal living areas, making day-to-day living possible without the need for stairs. The gourmet kitchen features quartz countertops and 42-inch cabinetry, while 8-foot interior doors add height and proportion throughout. Large sliding glass doors open to an oversized screened and covered patio with eastern exposure, morning sun, and no rear neighbors. Built in 2020, the home also offers the advantages of newer construction, complemented by a tile roof. Upstairs, the 4-bedroom, 3.5-bath floor plan includes three bedrooms, one serving as a second primary suite, along with a large bonus room and separate loft. Hawks Crest is set along Lake Howell and offers a clubhouse, fitness center, community pool, splash pad, parks, walking trails, grilling and picnic areas, and a pier with lake access. Park Avenue, shopping, dining, recreation, and major roadways are all within convenient reach.

1287 Verdant Glade Place, Winter Park

648 Worthington Drive, Winter Park
$2,700,000
5 Beds ⋅ 5 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code
Under Construction. Located in the Kenilworth Shores neighborhood, this stunning new residence brings an elevated level of new construction to an increasingly desirable pocket of Winter Park. A sophisticated modern farmhouse façade creates an impressive first impression, framed by a sweeping double-entry curved driveway that gives the home a commanding yet welcoming presence. Inside, the open-concept design is both polished and remarkably livable. A dedicated home office sits just off the entry, while the expansive main living space is anchored by a statement entertainment wall with an electric fireplace. Pocketing sliders disappear to create a seamless connection to the covered lanai and backyard, extending the home’s entertaining spaces outdoors. At the center of it all, the chef’s kitchen features Taj Mahal countertops, an oversized island, custom cabinetry, and a complete suite of Stainless steel appliances. A generous dining area and large walk-in pantry add to the home’s effortless functionality. One of the floor plan’s greatest advantages is the inclusion of two bedrooms on the main level, a rarity in Winter Park. The primary suite is particularly impressive, offering a true sense of retreat with a spa-inspired bath featuring dual vanities, a freestanding soaking tub, an oversized walk-in shower, and an expansive custom closet with a center island. The additional downstairs bedroom provides flexibility for guests or multigenerational living. Upstairs, three additional generously sized bedrooms are served by two full baths and a dedicated laundry room, along with an air-conditioned bonus room that easily functions as a sixth bedroom, theater, game room, or fitness studio. In all, the home offers five bedrooms, four and a half baths, a private office, and a climate-controlled bonus space, giving families room to spread out without compromise. The backyard was designed to feel like a private resort. A covered lanai and dedicated cabana with a full summer kitchen overlook the large pool and spa, while generous lawn space provides something increasingly difficult to find in newer Winter Park construction. Located minutes from Park Avenue's shops, cafes, and restaurants and close to Advent Health Winter Park, Cady Way Park, and the YMCA, this home offers an exceptional location. For those seeking new construction without compromising on space, location, or lifestyle, this is a Winter Park home that checks the boxes that matter.

648 Worthington Drive, Winter Park

7384 Grand Avenue, Winter Park
$385,000
3 Beds ⋅ 2 Baths ⋅ Oakcrest-516 SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully updated 3-bedroom, 2-bathroom home nestled in a quiet and desirable Winter Park neighborhood. From the moment you arrive, you’ll appreciate the lush new front landscaping and inviting curb appeal. Inside, the open-concept floor plan creates a spacious and welcoming atmosphere, complemented by soaring vaulted ceilings and beautiful brand-new tile flooring throughout the home. The thoughtfully designed split floor plan provides excellent privacy, with the primary suite separated from the additional bedrooms. The spacious living areas flow seamlessly into the kitchen and dining spaces, creating an ideal layout for both everyday living and entertaining. Fresh, modern finishes throughout make this home truly move-in ready. Step outside to your brand-new backyard pavers, creating a beautiful outdoor space perfect for relaxing, entertaining, or enjoying Florida’s year-round sunshine. With a 2-car garage, stunning updates, beautiful landscaping, and a peaceful neighborhood setting, this Winter Park home offers the perfect combination of comfort, style, and location.

7384 Grand Avenue, Winter Park

1250 S Denning Dr Unit Unit 233, Winter Park
$242,500
2 Beds ⋅ 2 Baths ⋅ Mead Garden Condominium SubDv. ⋅ 32789 Zip Code
Located just minutes from Winter Park's famed Park Avenue, this charming 2 bed, 2 bathroom corner condominium features a light and bright open floor plan, updated finishes, views of Mead Gardens, and one of Central Florida's most sought after locations! As you enter the front door, you are immediately welcomed by views of Mead Botanical Gardens, Khaki oak wood-look luxury vinyl floors, an open living/dining room combo, a private balcony with garden views and kitchen with freshly painted cabinets and stainless steel appliances. Off of the family room, 2 spacious bedrooms including a master suite with a renovated bathroom, and a second bedroom with private access. Everyday is a vacation when you can start your day off with a coffee on the private balcony, cool off on a warm summer's day in the pool and end it with a walk through the 48 acre natural enclave just next door as the sun sets. Zoned for A rated schools including Audobon Park and Winter Park High school and located just minutes from world class shopping, dining and entertainment in historic downtown Winter Park, Downtown Orlando, and College Park. Schedule your showing Today!

1250 S Denning Dr Unit Unit 233, Winter Park

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