Winter Park Homes For Sale & Real Estate - 358 homes

Remarks: Prime location meets exceptional value in the highly sought-after Winter Park area! This first-floor condo offers unbeatable convenience and strong investment potential in one of Central Florida’s most desirable communities. Ideally positioned just steps from the community pool and on-site laundry facilities, it provides easy, everyday access to key amenities. Whether you’re a first-time homebuyer ready to enter the market or an investor looking for a property with solid rental appeal in a high-demand location, this condo delivers both lifestyle and long-term opportunity. Don’t miss your chance to secure a well-located property at an attractive price point.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Leticia Morales (407-515-0318)

Remarks: Welcome to a one-of-a-kind opportunity inside the Winter Park city limits, where timeless character, meaningful updates, and an exceptional lifestyle and location come together in a perfect blend! Set on a beautifully landscaped 0.27-acre lot along Winter Park’s iconic tree lined, brick paved streets, this custom 5-bedroom, 4.5-bathroom residence with an office, a gym and attached in-law suite offers 3,851 square feet of living space, remarkable flexibility, and the kind of charm that simply cannot be replicated. Buyers will also appreciate the peace of mind that comes with major recent updates, including a metal roof installed in 2017, two HVAC units replaced in 2026, a third HVAC unit replaced in 2022, and two water heaters installed in 2025. The pool was resurfaced in 2025, the exterior and interior of the home was painted in 2025, & the house has also been completely re-plumbed! From the moment you arrive, the home makes a lasting impression with its large brick front porch, circular driveway, mature landscaping, detached oversized 2 car garage, and classic architectural presence. Large windows and thoughtfully designed living spaces fill the home with natural light, while hardwood floors, custom built-ins, plantation shutters, fireplaces, and refined traditional details create a warm and inviting feel throughout. This is the perfect blend of classic Winter Park charm and functional modern updates. The floor plan offers both elegance and versatility. In addition to five bedrooms, the home features an office space that can also serve as a formal living room, library, or flex space depending on your needs. The spacious family room is anchored by one of the home’s two wood burning fireplaces and opens beautifully to the outdoor living area, creating an easy flow for both everyday living and entertaining. The kitchen offers granite countertops, custom cabinetry, abundant counter space, a large island, and lots of natural light. It is open, functional, and well positioned at the heart of the home, allowing the next owner to enjoy it as is or make it their own. The primary suite is generously sized, featuring its own fireplace, an oversized bathroom with large walk-in shower, extensive vanity space, and a huge custom closet. One of the most special features of this home is the attached in-law suite, with its own separate entrance while still remaining accessible from the main home. Complete with a living room, bedroom, full bathroom, and kitchenette, this apartment style space offers exceptional flexibility for multigenerational living, live in family, guests, or even potential income producing use. Outside, the screened pool and spa area is a true highlight. Beautifully integrated into the architecture of the home, this private outdoor setting offers a covered lanai, lush tropical landscaping, and a peaceful courtyard style feel that makes it easy to relax, entertain, and enjoy Florida living year-round. The large paver driveway and detached garage create an impressive amount of parking and enhance the home’s unique layout and curb appeal. All of this is located less than 1.5 miles from Rollins College, Park Avenue, downtown Winter Park, public access to the Winter Park Chain of Lakes, and all the dining, shopping, boating, and everyday convenience that make this area so desirable. This is more than just a home. It is a rare chance to enjoy the Winter Park lifestyle in a custom home full of character, flexibility, and lasting value.

Listing is courtesy of: CREEGAN GROUP (407-622-1111)

Listing Agent: Chris Creegan (407-622-1111)

Remarks: Under Construction. Introducing the newest showpiece from LUIH Luxury Homes, perfectly positioned in the heart of Winter Park. Set on an oversized homesite along a quiet, tree-lined street, this residence immediately captivates with its expansive front lawn and timeless architectural presence. Inside, the home unfolds with a thoughtfully designed and highly functional floor plan that balances refined living with effortless entertaining. The spacious family room serves as the heart of the home, anchored by a sleek electric fireplace and framed by open sightlines into the kitchen and main living spaces, creating a warm yet sophisticated gathering environment. At the center of it all is a chefs kitchen designed to impress, featuring striking Calacatta quartz countertops, a full suite of Thermador appliances, custom cabinetry, an oversized center island, and an expansive walk-in pantry. Just beyond, the dining area is intentionally set apart to create a more intimate atmosphere, enhanced by a beautifully appointed wet bar with a wine refrigerator and floating shelving illuminated by elegant LED underlighting. The first-floor primary suite offers a true private retreat, with sliding glass doors opening directly to the pool and outdoor living areas. The spa-inspired bathroom is finished in exquisite marble tile and features a freestanding soaking tub, an oversized walk-in shower, dual vanities, and a generous custom walk-in closet designed for seamless organization. A rare and highly desirable feature for Winter Park living, the main level also includes a private guest suite along with a dedicated office, providing flexibility for hosting guests or working from home in comfort and style. Upstairs, a spacious loft-style living area creates the perfect setting for a media room, lounge, or secondary gathering space. Three additional bedrooms offer generous accommodations, each thoughtfully designed to provide comfort and privacy. Outdoor living is equally impressive. A large covered lanai with a fully equipped summer kitchen sets the stage for year-round entertaining and elegant alfresco dining. The backyard feels both expansive and secluded, highlighted by a resort-style pool and spa and complemented by ample green space for relaxation and recreation. Ideally located just minutes from the iconic shops, restaurants, and cafes of Park Avenue, the home offers the perfect balance of tranquility and connectivity. Residents are also moments from Cady Way Park and Winter Park High School, placing some of the area's best amenities right at your doorstep.

Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)

Listing Agent: Christopher Christensen (407-312-8003)

Remarks: Under contract-accepting backup offers. Welcome home to this immaculately maintained 3-bedroom, 3-bathroom brick home in Winter Park, ideally located in one of Central Florida’s most sought-after areas and offering the freedom of no HOA. Thoughtfully cared for and upgraded, this home blends timeless construction with modern comfort and exceptional functionality, making it perfect for everyday living and entertaining. The heart of the home is the stunning kitchen, featuring quartz countertops, an oversized farmhouse sink, stainless steel appliances, stylish cabinetry, and updated lighting, creating a bright and inviting space for cooking and gathering. Wood-look flooring flows through the main living areas, leading to a warm and welcoming living room highlighted by a charming painted brick fireplace. The spacious layout offers comfortable bedrooms and well-appointed bathrooms, providing flexibility for families, guests, or work-from-home needs. A large laundry room with a utility tub sink adds everyday convenience and functionality. Step outside to your private backyard retreat with a screened patio and sparkling pool, ideal for enjoying Florida living year-round. A storage shed in the backyard provides convenient space for tools, lawn equipment, and outdoor gear. The oversized two-car garage is a rare and valuable feature and includes a full bathroom with shower, making it perfect for a workshop, hobby area, home gym, or pool access. The garage refrigerator, workbench, and shelving convey, creating a move-in-ready space for projects and storage. Additional peace of mind comes with a roof replaced in 2021, adding long-term value and helping reduce insurance concerns. Located close to parks, shopping, dining, and everything Winter Park is known for, this home offers the perfect blend of style, flexibility, and lifestyle. This is a rare opportunity to own an immaculately maintained brick 3/3 home in Winter Park with no HOA, modern updates, and features that truly set it apart.

Listing is courtesy of: PHOENIX REALTY ADVISORS LLC (407-692-5939)

Listing Agent: Joseph Giardino (407-692-5939)

Remarks: Under contract-accepting backup offers. Nestled in the heart of downtown Winter Park, this beautifully maintained 1920s traditional residence captures the essence of Old Florida charm while offering the comfort of modern amenities. From the moment you arrive, the wraparound porch and circular drive create a welcoming first impression, setting the tone for the timeless character found throughout. Step inside to a gracious foyer accented by a cozy fireplace, leading into the spacious formal living room with its own gas fireplace and the elegant formal dining room. Gorgeous heart-of-pine floors run throughout the first floor, adding warmth and authenticity. The kitchen has been thoughtfully updated with top-of-the-line Thermador and Sub-Zero appliances, including a 72-bottle Sub-Zero wine tower and refrigerated drawers, making it as functional as it is beautiful. Open to the family room, complete with rich woodwork and a third gas fireplace, this space is ideal for gathering and entertaining. The primary suite is conveniently located on the first floor and features an updated ensuite bath. Upstairs, three additional bedrooms and two renovated baths provide comfortable accommodations for family and guests. A charming “sleeping room,” now used as a light-filled office, overlooks picturesque New England Avenue. Adding to the property’s appeal is a detached two-story guest house offering a full bedroom, full bath, sitting area, and kitchen—perfect for extended stays or as a private retreat. Outdoor living is equally inviting, with a back porch for grilling, a separate patio for lounging and mature landscaping that enhances the home’s curb appeal. Architectural details available for adding an oversize two-car garage, if desired. Perfectly positioned on the same block as The Alfond Inn and just two short blocks from the renowned Park Avenue district, this home offers not just refined living, but a downtown walkable lifestyle that is truly unmatched. Park Avenue is the cultural heart of Winter Park—a tree-lined promenade alive with award-winning restaurants, boutique shopping, art galleries and historic landmarks. Residents enjoy a vibrant calendar of events, from the Winter Park Farmers’ Market and seasonal art festivals to beloved holiday parades and outdoor movies under the stars. Here, every day is an invitation to experience the best of Central Florida living—whether it’s sipping coffee at a charming café, strolling to or after dinner surrounded by beautiful ambience, or embracing the timeless traditions that make Winter Park so treasured.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Mick Night (407-629-4446)

Remarks: Rare opportunity to own an established daycare operating from two structures on the same parcel, offered together with the real estate. The business currently provides immediate income for a hands-on owner or family-run operation. One structure is currently utilized for daycare operations, while the second structure is a single-family home that offers excellent potential for future daycare expansion (subject to licensing and approvals)—a unique value-add opportunity for growing operators. The property is already configured for childcare use with existing operations in place, making this an ideal turn-key opportunity for families looking to step into business ownership or operators seeking to expand their footprint. Sale includes real estate. Business goodwill, licensing, and operations may be included or negotiated separately. Convenient location with strong demand for childcare services. Please do not disturb staff or business operations. Showings by appointment only.

Listing is courtesy of: RE/MAX INNOVATION (407-281-1053)

Listing Agent: Ronald Trotter (321-331-1585)

Remarks: Taylor Morrison, Anastasia Model, 4 bdrm 3.5 baths on premium lot overlooking pond in the Meadows at Hawk's Crest. Large, spacious open floor plan with 20'+ ceilings, plantation shutters and builtins. Gourmet kitchen with pantry opens to dining area overlooking the great room. Master suite downstairs, laundry room, and half bath. Upstairs 3 bedrooms and 2 baths including an additional primary suite and loft area. Exterior features paver drive, tile roof., screen patio overlooking pond with fountain Community features: Fitness Center, pool, playground, dock, beautiful clubhouse. Short drive to Park Maitland School, Kelly's and Foxtail at community entrance; close to Shopping and Restaurants, and a short drive to Park Avenue and easy access to major roads to airport, attractions and UCF.

Listing is courtesy of: BECK REALTY LLC (407-256-6369)

Listing Agent: Joann Beck (407-256-6369)

Remarks: One or more photo(s) has been virtually staged. **This property qualifies for a closing cost credit up to $3,300 through the Seller’s preferred lender.** Welcome to this updated 2-bedroom, 2-bath first-floor condo in the heart of Winter Park. Tucked away at the back right corner of the building, this bright unit features hardwood floors throughout and an open living room with sliding glass doors leading to the community green space that is a tropical oasis. The adjacent dining area includes a stackable washer/dryer and flows into a modern kitchen with floor-to-ceiling cabinetry, granite countertops, and stainless steel appliances. Both spacious bedrooms sit near the entry, with the primary suite offering a walk-in closet and a sleek ensuite bath with a glass-front shower and floating vanity—mirrored in the newly updated guest bath as well. Enjoy low-maintenance living with access to resort-style community amenities including two pools, tennis courts, and a gym—all in a prime location! Schedule your private showing today!

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: Thomas Nickley, Jr (407-629-4420)

Remarks: Welcome to 188 Lewfield Cir — a beautifully designed 1-bedroom, 1-bath condo located in the highly desirable The Stratford at Winter Park Condominium community. This unit features an open floor plan that creates a bright, spacious feel, perfect for comfortable everyday living or entertaining guests. The layout maximizes functionality while maintaining a modern, low-maintenance lifestyle. Residents of The Stratford enjoy resort-style amenities including two outdoor swimming pools, a clubhouse, a fully equipped fitness center, and beautifully maintained grounds; offering both relaxation and convenience right outside your door. Located in the heart of Winter Park, you’re just minutes from premier shopping, top-rated restaurants, entertainment, and major roadways. Whether you're looking for a primary residence, seasonal retreat, or investment opportunity, this location places you in one of Central Florida’s most sought-after areas. Comfort. Convenience. Winter Park lifestyle. 188 Lewfield Cir is ready to welcome you home.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Johnny Aybar, Llc (407-808-9569)

Remarks: PRICE IMPROVEMENT! Welcome home to this updated 1-bedroom 1-bathroom GROUND FLOOR condo, ideally positioned toward the desirable rear of the sought-after Lakeside Manor community. The move-in-ready residence features a spacious, open floor plan enhanced by ceramic tile throughout, elegant crown molding and a thoughtfully updated kitchen complete with modern countertops, soft-close cabinetry, and newer stainless-steel appliances. Additional value-added improvements include newer windows and updated plumbing (re-piped and newer water heater) offering peace of mind to the next owner. Lakeside Manor is a highly desirable lakefront community offering private access to Lake Killarney a 239-acre spring fed lake. Residents enjoy premium amenities including a private boat ramp, community dock, access to boat slips (subject to availability, a monthly fee applies). The community also features a swimming pool, guest parking, extra parking (subject to availability, additional fee applies), community laundry facilities (nominal usage fee), storage cabinets, outdoor grill and picnic tables. Condo fees conveniently include monthly internet and water service. Ideally located just minutes from Winter Park and Park Avenue’s renowned shopping and dining, with quick access to I-4 and Downtown Orlando, this property offers the perfect combination of comfort, convenience, and lifestyle.

Listing is courtesy of: PINEAPPLE PLACE REALTY, LLC (407-497-8563)

Listing Agent: Andrea Aylett-Hosch (407-497-8563)

Remarks: Under contract-accepting backup offers. Welcome to 246 Palmer Avenue! Build your dream home or live in this charming home As-Is. Situated on a 14,252 sq.ft (0.33) corner lot on a beautiful brick street in the heart of Winter Park, this charming cottage offers timeless character, thoughtful updates, and a highly desirable location just minutes from Park Avenue, Rollins College, and the Winter Park Chain of Lakes. This well-maintained home features a layout with warm and inviting living spaces and abundant natural light. The original front door faces Palmer Avenue, while a later addition created the day-to-day entrance along Old England Avenue. Two separate living areas provide versatility for both relaxing and entertaining, and both the family room and the original living room, currently used as an office, feature wood-burning fireplaces. Just off the family room, a screened porch overlooks the lap pool and backyard, creating an easy connection between indoor and outdoor living. The dining room is lined with built-in bookcases, one of several thoughtful details found throughout the home. The kitchen enjoys views of the backyard and opens to a breakfast area with built-in cabinetry and French doors leading outside. A walk-in pantry adds practical storage. Off the original living room, an enclosed sunroom with original tile and additional built-ins offers a cozy space for reading, working, or unwinding. The primary bedroom opens to the backyard through French doors and includes built-in drawers in addition to closet storage. Its bath features a pedestal sink and clawfoot tub. A second bedroom is located across the home with access to a bathroom off the hallway, providing comfort and privacy for guests or family. Recent updates include a 2014 roof, gas water heater (2022), HVAC systems (2022 and 2023), and updated plumbing and electrical panels. A sprinkler system adds convenience for maintaining the grounds. This is a rare opportunity to build your dream home or enjoy this charming property as-is, ideally located just a couple of blocks from Park Avenue.

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Wendy Williams Crumit (321-356-8590)

Remarks: In the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean estate is a private oasis. With over 11,000 square feet of living area and a beautifully landscaped lakefront lot, this residence offers an exceptional blend of elegance, charm and privacy rarely found in Winter Park. The home features seven spacious bedrooms and nine full and two half baths. Entertain in the all-glass conservatory, dedicated theater room with motorized seating and a fully equipped game room. Modern conveniences throughout including gas-powered generators, an elevator and dumbwaiter. Two above-garage apartments provide ideal accommodations for guests and family. Outdoors, enjoy an expansive covered lanai, infinity edge pool and spa, boat dock with jet ski lift, and a summer kitchen complete with wood-burning fireplace, gas grill, refrigerator and icemaker, all overlooking the beautifully landscaped yard and lake. With its private gated entrance, this home is a one-of-a-kind opportunity to enjoy all the amenities Winter Park and Windsong have to offer.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Hal George (407-832-8751)

Remarks: Under contract-accepting backup offers. Step into your own private retreat in the sought-after Winter Woods community! This beautifully maintained 3-bedroom, 2-bath pool home offers 1,745 square feet of inviting living space designed for both comfort and effortless entertaining. From the moment you arrive, you’ll be greeted by lush, mature landscaping that creates a sense of privacy and charm. Inside, the home features a bright, open layout filled with natural light and a warm, welcoming feel throughout. The beautifully updated kitchen is a true standout, featuring brand-new quartz countertops, modern finishes, and ample space for cooking, gathering, and creating lasting memories. Out back is where this home truly shines—enjoy your screened-in pool and spacious patio, perfect for relaxing weekends, hosting friends, or soaking up Florida’s year-round sunshine without the bugs. A 2-car garage adds convenience and storage, while the location is hard to beat—just minutes from the boutiques, dining, and vibrant atmosphere of Park Avenue and all that Winter Park has to offer. Homes like this don’t come around often—schedule your showing today and experience it for yourself! ROOF: 2023 AC: 2012 HWH: 2017 Electrical: Updated 2022

Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)

Listing Agent: Joseph Sipp (407-820-7016)

Remarks: Welcome home to this fully renovated 2-bedroom, 1.5-bath residence! This home features a brand-new kitchen, new flooring throughout, and beautifully updated bathrooms. Nestled in a quiet neighborhood, it offers a large backyard—perfect for outdoor entertaining or future expansion. Ideal for a first-time homebuyer or anyone seeking stress-free living. Best of all, NO HOA! Conveniently located near major highways, great schools, shopping, and dining in the highly desirable Winter Park area. Don’t wait—make this home yours today!

Listing is courtesy of: THE FIRM RE (407-227-3345)

Listing Agent: Nimrah Ashraf (786-356-6611)

Remarks: This charming 2-bedroom, 1.5-bath condo offers a desirable townhome-style layout with spacious living areas and thoughtful storage throughout. The community features deluxe vinyl fencing installed by the HOA, along with a clubhouse and a community pool, providing great amenities for residents to enjoy. Inside, you’ll find the convenience of an in-unit washer and dryer combo, ample storage under the stairs, and a large carport with an attached storage shed. The spacious primary bedroom opens directly to a generous private balcony—perfect for relaxing or unwinding after a long day. Ideally located just 15 minutes or less from UCF, Rollins College, Valencia East, and Full Sail University, and only 20 minutes from Orlando International Airport. Whether you’re a first-time homebuyer, student, investor, or looking to make your move into Winter Park, this home delivers affordability, convenience, and excellent potential.

Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)

Listing Agent: Javier Albelo Rivera (407-655-7101)

Remarks: PRICE ADJUSTMENT! Welcome to this beautifully maintained 3-bedroom, 2-bath home for sale in Winter Park located in the highly sought-after Garden Grove community. Situated on a generously sized lot, this property offers the perfect blend of comfort, functionality, and outdoor living, with plenty of room to add a pool and create your own private backyard retreat. Inside, you’ll love the spacious split-bedroom floor plan designed for both privacy and everyday convenience. Ceramic tile flooring throughout adds style and easy maintenance, while the open family and dining room combination creates a warm and inviting space for relaxing or entertaining. A charming wood-burning fireplace adds character and comfort, making this home feel cozy and welcoming. The updated kitchen is a standout feature, opening seamlessly to the dining area and offering granite countertops, new cabinetry, and a convenient breakfast bar that is perfect for casual dining or hosting guests. Sliding glass doors lead directly to the expansive fenced backyard, making indoor-outdoor living easy and enjoyable. The oversized backyard is one of this home’s biggest attractions. Whether you envision weekend barbecues, a play area for pets, lush gardening, or extra space for your RV, boat, or recreational vehicles, this property offers flexibility that is hard to find in Winter Park. With room for a pool, the possibilities are endless. Major improvements include a roof replaced in 2019, giving buyers added peace of mind. Conveniently located near shopping, dining, parks, and major roadways, this Winter Park home offers space, value, and versatility in one of the area’s most established and desirable neighborhoods. If you are searching for a home with a large fenced yard, updated kitchen, split floor plan, and room for all your toys, this Garden Grove gem is a must-see.

Listing is courtesy of: WATSON REALTY CORP (407-323-3200)

Listing Agent: Carla Robles (407-462-2347)

Remarks: 2 bedroom, 2 bathroom condo located in the desirable and well maintained Waterfall Cove community in Winter Park. Unit is long-term tenant occupied, offering immediate rental income for an investor buyer. Interior is in original condition and presents an excellent opportunity for updates and value enhancement. Enjoy a highly walkable location close to Whole Foods, LA Fitness, Winter Park Village, shopping, dining, and more. Community amenities include a pool, dog park, and mature landscaping. Convenient access to I-4 and major employment centers. Please do not disturb tenant. Call or text for showing instructions

Listing is courtesy of: MTRE GROUPE LLC (786-282-9992)

Listing Agent: Mauricio Toro (786-282-9992)

Remarks: One or more photo(s) has been virtually staged. Incredible Value!!! Major price reduction! Private Lakefront Living! Move-in Ready! Wake up to water views, quiet mornings and the kind of lifestyle that rarely becomes available in the Winter Park/Howell Branch area. Set along the shores of a private ski lake- Lake Florence, this single-level lakefront residence offers a serene retreat within an intimate gated enclave of just 28 homes. A setting that feels private and peaceful that is increasingly hard to find. Designed for both everyday comfort and effortless entertaining, the thoughtfully planned 4-bedroom, 3.5-bath layout includes a dedicated office, formal dining room and a desirable three-way split floor plan that provides flexibility and privacy for today’s lifestyle. At the heart of the home, the gourmet kitchen blends beauty and function with quartz countertops, a substantial center island, natural gas cooktop, 42" solid wood cabinetry, walk-in pantry, and a generous butler’s pantry—perfect for hosting or simply enjoying the flow of daily living. Rich wood flooring carries throughout the home connecting the kitchen seamlessly to the light-filled family room and casual dinette area. The primary suite is a true lakefront sanctuary featuring peaceful water views, two walk-in closets and a spa-inspired bath with dual sinks and an oversized shower with dual shower heads. Many upgrades are to be found through out this home such as an extra oversized storage closet, crown molding, custom mud room off of the laundry room, high ceilings, tray accents and abundant natural light to enhance the home’s relaxed, refined feel. Outdoors, the property transforms into a private lakefront escape. Enjoy sweeping water views, a sparkling pool and spa, custom rock waterfall, screened-in lanai and a fully fenced yard framed by tall privacy hedges and mature trees—ideal for quiet evenings or weekend gatherings. Direct lake frontage and access to a nearby community dock complete the lifestyle experience. A three-car garage with a separate AC wall unit offers added versatility—perfect for a workshop, home gym, or additional storage. Thoughtfully positioned, this home represents a rare opportunity to own a lakefront retreat that delivers serenity, lifestyle and value—all within close proximity to shopping, dining and top-rated schools in a prime location!

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Ellen Bessette (407-496-0076)

Remarks: Welcome to 870 Carver Street, a versatile three-bedroom, three-bath residence offering privacy, thoughtful design, and two distinct living experiences in the heart of Winter Park. With 1,875 square feet under air, the property includes a 1,209-square-foot, two-bedroom, two-bath main home and a 666-square-foot, one-bedroom, one-bath garage apartment, ideal for multigenerational living, rental income or private home office use. Designed by award-winning architect David Crabtree of Hive Workshop and constructed by Barefoot Brothers Construction, the home showcases vaulted ceilings with exposed rafters, warm wood finishes and industrial-inspired black metal ductwork. The primary suite includes a floating wall closet system, in-suite laundry and a spa-style bath with dual-sink floating vanity and glass-enclosed walk-in shower. The second bedroom features custom built-ins and a full bath with a tub-shower combination. A chef’s kitchen anchors the open living area with solid wood cabinetry, under-cabinet lighting and a substantial island with seating for four. Black aluminum-framed windows flood the interiors with natural light, enhancing the home’s open-plan design. The garage apartment is accessed via a private entrance and dedicated driveway that fronts Carver Street. The home’s distinct dual-street orientation enhances separation of space, particularly for rental or guest use. Inside, the apartment mirrors the main home’s design language with vaulted ceilings, tile flooring, a full kitchen, en-suite bath, private laundry, and white oak stairs leading to a cohesive living and dining area. The garage offers oversized dimensions and extra depth for storage, and is accessed via a sliding steel-framed wood-clad gate along Railroad Avenue. A second driveway and swing gate on Carver Street are thoughtfully positioned to serve the apartment independently, offering private access for separate use. The fully fenced yard includes a rear garden courtyard, covered entries and an expansive front porch with warm wood architectural detailing. Ideally within short distance to Park Avenue, Winter Park Village, Whole Foods Market, the Winter Park Golf Course, and SunRail and Amtrak stations, this is a rare opportunity to own a design-forward residence with dual-street presence in a transforming urban enclave.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Drew Henner (407-406-0662)

Remarks: AGENTS - PLEASE VIEW REALTOR REMARKS IN THE MLS…*** Great value-add opportunity in Winter Park with strong rental potential near local colleges. TWO LEVELS, SPACIOUS 1,085 square feet Condo, 2-BEDROOM, 2 FULL-BATHROOM one located on the second floor and the other full bath on main level, unit building has a convenient location near the front of the community. Unit features a functional layout with the main living areas on the first floor and BOTH BEDROOMS UPSTAIRS. The open living and dining area provides ample space for everyday living and entertaining, and a guest bath is conveniently located on the main floor and a balcony where you also find your separate laundry room. The primary suite also features a PRIVATE BALCONY, perfect for enjoying a quiet outdoor retreat. The property offers a great opportunity for cosmetic updates, allowing a new owner to add personal touches and build additional value. The community is currently undergoing renovations, which will further enhance the appeal of the property. Unit needs some TLC but has great potential. Located in WINTER PARK, this condo is just minutes from FULL SAIL University and ROLLINS COLLEGE, making it an excellent option for investors, student housing, or a primary residence. With strong rental potential and convenient access to shopping, dining, and major roadways, this property presents a compelling opportunity in a highly desirable area.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)

Listing Agent: Nellie Peralta (321-299-5544)