Winter Park Homes For Sale & Real Estate - 445 homes

Remarks: A fully renovated property is situated in the heart of Kenilworth Shores, Winter Park and nestled among tree-canopied streets. This home is a rare find, completely reimagined in 2005, adding square footage and function, creating a floor plan that is unique to this home. The layout includes four bedrooms with four full baths and one half bath; three are ensuites and stretch across 2,638 square feet with generous living spaces in this Florida ranch-style home. Gorgeous Brazilian cherry wood flooring in living spaces adds to the luxury of this home. The formal living room opens to the dining room and kitchen combined, adding back family space, which features vaulted ceilings and French doors to the back patio. There is a dedicated office or flex space to accommodate your family. The backyard includes a covered porch with an insulated roof and remote-controlled screens that overlook the saltwater pool, recently refinished and tiled, all ideal for entertaining. The pool also includes a water feature and solar heating for year-round use. Expansive patio surrounds with paver decking are the ideal setting to lounge and soak up the sun. Plenty of green space for play and property secured by a 6-foot vinyl fence with two gates and solar lantern lighting, adding to the beauty. A timeless kitchen awaits with solid cherry wood, clean-lined cabinetry with under-mount lighting, Silestone counters, stainless appliances and loads of counter space. Additional recessed task lighting makes cooking a breeze and a generous pantry space with solid wood cabinetry combined with laundry provides great storage. Imported Italian ceramic floors with neutral tones beautifully ground the kitchen and dining rooms. The primary suite is spacious and was expanded with renovation to allow for a spacious bath with a walk-in shower with a frameless glass enclosure, double sinks and tons of storage. Fresh carpet in all bedrooms was installed in 2023 and two of the additional bedrooms are en suites with an added study or flex room to each suite. This home has been meticulously updated and maintained and additional upgrades include a new roof (2022), electrical panels replaced (2005), exterior paint and trim (2022), an owned security system with all windows and doors, two touch panels and remote control with an app, an EcoBee Thermostat, programmable and remote control with an app, updated LED recessed lighting in select rooms, an indoor laundry room with pantry storage, large standup attic space, a full-yard zoned sprinkler system and fresh groundwater well, two water heaters, a 6 by 10-foot backyard storage shed and so much more. This home is zoned for some of the best Orange County schools: Brookshire Elementary, Glenridge Middle School and Winter Park High School, which offers a globally recognized International Baccalaureate program. Close to every convenience with two Publix grocers less than two miles away, Winter Park Pines Golf Course, a short drive to Park Avenue and Baldwin Park Town Center with world-class restaurants, shopping, parks and museums. Cady Way public park is a short walk and features a new community swimming pool, a home for youth sports, a children's playground and fantastic recreational and bike trails. This home provides all the Winter Park lifestyle that makes our city so special. Kenilworth Shores is an established community with much to offer.

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

Listing Agent: Alison Mosley (407-304-6458)

Remarks: Enjoy the best of living in this beautifully renovated well maintained 2-bedroom, 2-bath condominium located in the highly desirable gated Park West Condominiums. Perfectly positioned just steps from the renowned Park Avenue, this exceptional residence offers walking distance access to award-winning restaurants, charming boutiques, sidewalk cafés, and the popular weekly farmer’s market. This rare 3rd-floor corner unit which enhances privacy was completely remodeled in 2019 with quality upgrades throughout. The interior features are engineered wood flooring, updated tile, modern ceiling lighting, and a bright open-concept floor plan filled with natural light from expansive sliding glass doors leading to three private walk-out balconies. The redesigned kitchen in 2019 includes new cabinetry, countertops, a complete suite of kitchen appliances, including washer and dryer. Both bathrooms have also been tastefully renovated, creating a clean and contemporary feel throughout the home. Additional improvements include a brand-new HVAC system installed in July 2024, offering peace of mind and energy efficiency for years to come. Spacious bedrooms, generous storage, and seamless indoor-outdoor living make this condo ideal for both everyday living and entertaining. Park West residents enjoy beautifully maintained grounds along with community amenities including a sparkling swimming pool and tennis courts. The community is also conveniently located to Rollins College and Full Sail College. Whether you are searching for a full-time residence or seasonal retreat, this exceptional condo combines timeless Winter Park charm with modern updates and an unbeatable location.

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

Listing Agent: Kevin Mcclanahan (407-491-8509)

Remarks: JUST LISTED! Located in the highly sought-after Winter Park Lake Sue area, this exceptional contemporary residence offers a rare opportunity to enjoy luxury living among some of the most architecturally significant and beautifully designed homes in Central Florida. Positioned within one of the region's most desirable neighborhoods, the property combines modern design, exceptional functionality, and an outstanding lifestyle location. From its prominent presence to its thoughtfully executed interior spaces, the home offers a seamless blend of modern esthetics and comfort. The open-concept floor plan is designed for both everyday living and entertaining, with expansive living areas that transition effortlessly into the covered outdoor living space, summer kitchen, resort-style pool, and heated spa. A highly desirable layout places both the luxurious primary suite and an additional bedroom/flex room on the main level, providing exceptional flexibility for guests, a home office, fitness space, or multi-purpose living. Upstairs, additional bedrooms and a large bonus room create ample space for family and entertaining. The private first-floor primary suite serves as a true retreat, featuring direct access to the outdoor living areas and a beautifully appointed spa-inspired bath. Throughout the home, quality finishes, extensive wood flooring, designer lighting, custom window treatments, and carefully curated details create an elevated living experience. The kitchen serves as the centerpiece of the home, featuring premium appliances, generous workspace, and a large entertaining island that connects seamlessly to the main gathering spaces. Perhaps most compelling is the location. Zoned for highly regarded Audubon Park K-8 and Winter Park High School, the home enjoys convenient access to Park Avenue, Rollins College, East End Market, Winter Park Village, Downtown Winter Park, and Downtown Orlando. Residents enjoy the unique advantage of being positioned between the charm and sophistication of Winter Park and the energy of Orlando's most vibrant dining, cultural, and lifestyle destinations. Opportunities to secure a fantastic residence at this price point in the Winter Park Lake Sue area are increasingly rare. This is a unique opportunity to enjoy a wonderful lifestyle and home in one of Central Florida's most desirable neighborhoods.

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

Listing Agent: Robert Kurzreiter Pa (407-476-4156)

Remarks: Situated on arguably the finest brick street in Winter Park, beneath a canopy of live oaks, this fully renovated 4-bedroom, 4-bath home delivers the rarest combination: the soul of an established neighborhood, unique charm and character, and the bones of new construction. Gutted to the studs and rebuilt with intention, every major system is new — electrical, Carrier ACs, roof, ductwork, drywall, Pella windows +++. With elevated finishes, like designer tile and quartz countertops as well as floors and beautifully reimagined kitchen and baths. A second-floor addition adds a sprawling 21 x 24 foot private primary suite and home office, one of the many reasons this an ideal setup for MULTIGENERATIONAL families and those who work from home. A welcoming fireplace, lush mature landscaping, butler's pantry, numerous built ins, custom tile work, and an address minutes from Park Avenue make this one of Winter Park's most compelling offerings. Come imagine the possibilities.

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

Listing Agent: Olivia Maxwell (407-222-4440)

Remarks: Welcome to 2052 Leanne Ct, a home that exudes warmth and elegance. The living room is graced with a cozy fireplace, perfect for those chilly evenings. The kitchen is a chef's dream, boasting all stainless steel appliances for a sleek, modern look. The primary bedroom is a haven of comfort with double closets for ample storage. The primary bathroom is a sanctuary with double sinks, providing ample space for your morning routine. The fenced-in backyard provides a private outdoor space for relaxation and entertainment. The home has been recently updated with fresh interior and exterior paint, giving it a clean, refreshed look. New flooring throughout the home adds a touch of sophistication and durability. The new appliances ensure efficiency and convenience. Included 100-Day Home Warranty with buyer activation

Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)

Listing Agent: Karen Albright (480-462-5392)

Remarks: Under contract-accepting backup offers. Rare opportunity in the heart of 32789 — priced under $500K, this 3-bedroom, 2-bathroom Winter Park home delivers the location, lot, and bones that buyers in this zip code rarely find at this price point. Zoned for Dommerich Elementary and Winter Park High School and situated on a generous 0.23-acre lot, this is the one worth moving quickly on. Upon entry, a sun-drenched living room leads to a formal dining room, which connects to a secondary living area perfect for entertaining. The open kitchen features granite countertops, stainless steel appliances, and a casual eat-in area, while refinished terrazzo floors run throughout the home adding character and easy-care durability that's quintessentially Florida. 2021 roof and HVAC mean the big-ticket items are already done. Step outside to a large screened-in patio overlooking a spacious backyard with plenty of room to add a pool or expand. One or more photo(s) was virtually staged. Minutes from Park Avenue and Downtown Winter Park's incredible restaurants and fantastic shopping, Rollins College, UCF, AdventHealth Winter Park, Downtown Orlando, and more.

Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)

Listing Agent: Caroline Fiore (407-538-2381)

Remarks: *Ask about a lender provided credit up to $12,500 on this home!*1927 Eland Avenue is a rare single family home for sale in Winter Park FL 32789, located on a quiet dead end street with no rear neighbors. This Winter Park home features a main residence plus a detached in law suite ADU built in 2022, offering exceptional flexibility for multi generational living, guest accommodations, or rental income potential. The main home offers three bedrooms and two bathrooms with real wood floors, Spanish Colonial architectural details, abundant natural light, and a functional open living layout. The primary bedroom and bathroom offer the opportunity to be expanded, allowing a future owner to customize and enhance the suite to their needs. Interior features include a wood beamed dining room, fireplace, and a built in bar with mini fridge, making this home ideal for entertaining and everyday living. Major updates include a 2015 roof, 2018 windows, and a 2022 HVAC system, providing added peace of mind for buyers seeking an updated home in Winter Park Florida. The detached in law suite cottage includes two bedrooms and one bathroom, along with a modern eat in kitchen featuring white cabinetry, butcher block countertops, and contemporary finishes. The guest house also offers its own laundry area and skylights that enhance the bright, open feel. A private brick paver patio creates a separate outdoor living space exclusively for the ADU. This ADU has the ability to be separately metered from the main house and can have its own independent address if desired. The main home’s outdoor living area includes an outdoor kitchen, brick paver patio, and a private backyard designed for relaxing and gatherings. Conveniently located near Lee Road, State Road 17-92, and Interstate 4, this property provides easy access to Winter Park, Maitland, College Park, and downtown Orlando. Buyers searching for a Winter Park home near Park Avenue, Rollins College, Winter Park Village, Trader Joe’s, SunRail, and the Winter Park Farmers Market will appreciate the central location and walkable lifestyle. This is a rare opportunity to own a versatile single family home with an in law suite ADU in one of the most desirable neighborhoods in Winter Park FL.

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

Listing Agent: Ryan Leitter (321-684-9699)

Remarks: Rare corner unit opportunity — this 3-bedroom, 2-bath home sits on the upper level of the highly sought-after Hidden Oaks community in Winter Park, tucked in one of the neighborhood's quieter, more private sections away from street traffic and parking lot noise. Unlike most units in the complex, this home benefits from windows on three sides, flooding every room with natural light throughout the day — a feature you simply won't find in the standard interior units. The second-floor position adds both privacy and tranquility, with no footsteps overhead and elevated views of the surrounding mature tree canopy that Hidden Oaks is known for. The functional floor plan makes the most of every square foot, with a spacious living area that feels open and airy thanks to that exceptional three-sided window exposure. The kitchen has been thoughtfully updated with a brand-new range, and the refrigerator, dishwasher, and washer/dryer were all replaced approximately three years ago — move-in ready from day one. Perfectly positioned for convenience without sacrificing peace and quiet: minutes from Full Sail University, UCF, downtown Winter Park, and downtown Orlando, with quick access to the 408 and 417. One assigned parking space is included, with two additional permits available through the association.

Listing is courtesy of: SHORES REAL ESTATE (407-353-0106)

Listing Agent: Abby Yelken (407-496-9822)

Remarks: Welcome to 2889 Rouen Avenue, Fresh exterior paint and move-in-ready 3-bedroom, 2-bath residence offering approximately 1,140 square feet of comfortable living space. This home features a bright and functional layout, well-sized bedrooms, and a large fenced yard with plenty of room to enjoy the outdoors. Brand New water heater. Brand new Roof is underway. Conveniently located near Rollins College, Park Avenue, Full Sail University, shopping, dining, and I-4, and zoned for Dommerich, this property offers an outstanding opportunity in a sought-after location. see private remarks and showing time for direct seller’s contact.

Listing is courtesy of: HELLOSOLD LLC (954-778-5300)

Listing Agent: Dan Farber (954-778-5300)

Remarks: Welcome home to this charming and fully remodeled 2-bedroom, 1-bathroom gem nestled in the heart of Winter Park AND College Park. Located just minutes away from Downtown Orlando, Disney, Universal and Advent Health, this sought-after location offers convenience and comfort. This home boasts not only a prime location but also a cozy ambiance that will make you feel right at home. With its hardwood floors adding warmth and character, and the spacious fenced-in backyard providing privacy and room for outdoor activities, this property is ideal for those seeking the perks of Winter Park and College Park living as well as the fun outgoing, Orlando attractions.

Listing is courtesy of: FLORIDA HOME TEAM REALTY LLC (407-774-8100)

Listing Agent: Stacia Stephenson (407-415-5700)

Remarks: One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Waterfall Cove, where urban convenience meets tranquil living. This charming 2-bedroom, 1-bathroom condo offers a cozy retreat with all the perks of modern living. Located in the heart of Orlando, this condo is perfect for those looking for a blend of city life and natural beauty. As you step into the condo, you're greeted by a bright and spacious living area, perfect for relaxing or entertaining guests. The kitchen features modern new (2025) appliances and ample storage space, making cooking a breeze. The bedrooms are spacious and plenty of natural light, creating a peaceful ambiance. One of the highlights of living at Waterfall Cove is the stunning waterfall feature that gives the community its name. This serene setting is perfect for unwinding after a long day or enjoying a peaceful morning coffee. The community also features a pool and fitness center, providing residents with plenty of opportunities to stay active and healthy. Waterfall Cove is ideally located near Interstate 4, making it easy to commute to major job centers in Orlando. It's also just a short drive away from downtown Orlando and Winter Park, where you can explore a variety of dining, shopping, and entertainment options. Additionally, the condo is close to Rollins College, making it a great option for convenient housing. For those who enjoy the outdoors, Waterfall Cove is close to several parks and nature reserves, where you can hike, bike, or simply enjoy the beauty of the Florida landscape. And if you're a coffee lover, you'll appreciate the proximity to Starbucks, where you can grab your favorite drink on the go. In conclusion, Waterfall Cove offers the perfect blend of comfort, convenience, and natural beauty. With its modern amenities, convenient location, and affordable pricing, it's no wonder why living in this area is so desirable. Don't miss out on the opportunity to make Waterfall Cove your new home! THIS PROPERTY MAY QUALIFY FOR UP TO 40,000.00 IN DOWN PAYMENT ASSISTANCE.

Listing is courtesy of: RE/MAX SELECT GROUP (954-905-2772)

Listing Agent: Jason Price (954-905-2772)

Remarks: Fully reimagined and COMPLETELY RENOVATED AND DESIGNED BY HGTV DESIGNER, this stunning 4-br, 3-ba home in desirable Winter Park Pines sits proudly on a spacious corner lot and offers Modern Luxury with thoughtful, HIGH END UPGRADES throughout. The interior showcases all-new cabinetry and countertops, highlighted by a dramatic waterfall kitchen island, brand-new appliances including a built-in microwave tucked into a custom pantry cabinet. Every detail has been carefully considered, from new luxury vinyl flooring and interior doors to upgraded closet shelving, sleek bathroom mirrors, and stylish shower enclosures. Sound insulation enhancements in key areas—including the primary suite, bathrooms, and kitchen walls—provide added comfort and privacy, while smart ceiling fans, dimmable lighting, USB charging outlets, and pre-wiring for under-cabinet lighting and wall-mounted TVs bring modern convenience to everyday living. Beyond the interior, the home continues to impress with major system upgrades and durable exterior improvements designed for long-term peace of mind. Enjoy a BRAND NEW ROOF with transferable warranty, updated soffit and fascia, rot-proof siding and porch columns, and new fiberglass exterior doors with built-in blinds. The property also features a new irrigation system, vinyl fencing, and an expansive 3+ car driveway. Behind the walls, everything has been upgraded—including full electrical rewiring with a new 200-amp service, all-new plumbing from underground lines to fixtures, and a high-efficiency HVAC system with new ductwork and insulation for maximum energy savings, making this home truly MOVE-IN READY with no detail overlooked.

Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)

Listing Agent: Kelly Butterfield (407-463-1289)

Remarks: New Construction – Carefully Curated by SGC Conctruction. Discover Modern Luxury in Winter Park's Latest Neighborhood, Winter Park Grove! Step into a world of refined living with this breathtaking new construction pool home, located in the vibrant heart of Winter Park. Just moments away from the eclectic energy of Park Avenue, this modern masterpiece seamlessly blends sophistication, style, and convenience — all within walking or biking distance of premier restaurants, cafés, boutique shops, and entertainment venues. Designed for both daily comfort and elevated entertaining, the open-concept floor plan boasts thoughtful design and high-end finishes throughout. Luxury details abound, including engineered wood floors featuring an elegant herringbone pattern in the foyer, smooth finish Level 4 drywall, and a cozy electric fireplace that enhances the spacious great room, accentuated by LED mood lighting in the coffered ceiling. The expansive gourmet kitchen is a chef’s delight, equipped with ceiling-height cabinets for ample storage and premium Thermador appliances, including a 36” gas cooktop, wall oven, built-in microwave, French door refrigerator, and a wine fridge — all complemented by sleek cabinetry and contemporary details. A beautiful dry bar adjacent to the kitchen provides extra space for coffee, wine, or entertaining guests. Offering four generous bedroom suites, this home includes a luxurious primary suite on the main level, along with a versatile second suite on the first floor, ideal for use as an office or guest retreat. Upstairs, two additional suites are connected by a flexible bonus room — perfect for a home office, gym, second living area, or even a fifth bedroom. Step outside to your private outdoor oasis, featuring a covered lanai with automatic roll-down screens, a fully-equipped summer kitchen (complete with grill, sink, and refrigerator drawers), and a sparkling pool adorned with travertine decking — perfect for year-round Florida entertaining. The elegant exterior showcases outdoor lighting and lush landscaping, along with a gas generator to ensure your home is always prepared for storm season.Don’t miss your opportunity to own this exquisitely crafted home in one of Orlando’s most sought-after neighborhoods. Schedule your private showing today and experience the pinnacle of luxury living in Winter Park! There are special builder incentives available right now- Call for details!!

Listing is courtesy of: RE/MAX EXCLUSIVE COLLECTION (407-447-2829)

Listing Agent: Kim Griffin (407-314-5033)

Remarks: Under contract-accepting backup offers. Located within the gated community of Hawk’s Crest, one of Winter Park’s most desirable neighborhoods, this beautifully maintained two-story home is set on an oversized lot with tranquil pond views and a layout designed to live effortlessly. Light-filled, open, and thoughtfully upgraded, the home offers a balance of comfort, style, and everyday functionality. A pavered driveway and walkway create an inviting arrival, leading into a bright interior with soaring ceilings and abundant natural light. The main living space flows seamlessly, anchored by a chef’s kitchen featuring quartz countertops, stainless steel appliances, solid wood cabinetry, and a generous island with breakfast bar—perfect for casual meals, entertaining, or gathering at the end of the day. The kitchen opens naturally to the dining and family rooms, creating a connected space that feels both open and welcoming. Sliding doors lead to a covered lanai overlooking the pond, extending the living space outdoors and providing a peaceful backdrop for morning coffee or evening relaxation. Inside, upgraded luxury vinyl flooring and custom roller shades add warmth and a polished finish throughout the main living areas. The first-floor primary suite offers a private retreat with serene water views, a spacious walk-in closet, and a spa-inspired bath with dual vanities and a walk-in shower. A dedicated office on the main level adds flexibility and can easily function as a fifth bedroom if needed. Upstairs, a generous loft provides additional living space—ideal for a media room, play area, or secondary lounge—while three well-sized bedrooms offer comfort and versatility for guests, hobbies, or working from home. Energy-efficient features, ample storage, and thoughtful design make the home as practical as it is inviting. Residents of Hawk’s Crest enjoy resort-style amenities including a community pool, fitness center, clubhouse, playgrounds, and scenic walking paths, along with HOA-included lawn care for low-maintenance living. Ideally situated near shopping, dining, outdoor recreation, and major roadways, this home offers both convenience and a sense of retreat within Winter Park. Come experience the lifestyle and setting that make this home truly special—schedule your private showing today.

Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)

Listing Agent: Beth Hobart (407-227-8192)

Remarks: Pre-Construction. To be built. Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with intention, The Enclave offers a rare opportunity to enjoy a private, residential setting while remaining connected to the area’s finest dining, shopping, and cultural amenities just minutes away in downtown Winter Park.. With a limited collection of custom homes, this community delivers an elevated lifestyle defined by architecture, walkability, and enduring charm. This custom single-family home is thoughtfully designed with exceptional craftsmanship and upscale finishes throughout. Each residence features high-performance, low-E double-pane windows, 8-foot solid core interior doors, and tankless gas water heaters for modern efficiency and comfort. Homes are appointed with premium Wolf and Sub-Zero appliances, designer-selected finishes, and a curated palette of colors and materials. These homes have it all; summer kitchens well equipped with fridge and grill and a sparkling pool. Spacious layouts, refined detailing, and quality construction create an elevated yet livable environment, all set within a beautifully landscaped and private setting. There is still time for the Buyer to personalize design selections and explore certain home plan modifications. Upgrade options are also available, including the opportunity to add a detached cabana and/or guest house, subject to builder pricing, lot compatibility, and community guidelines. Please inquire for additional details and available customization options.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Matthew Burks (407-257-5347)

Remarks: Welcome to your dream home in the highly sought-after community of Winter Park Pines! This beautifully maintained 4-bedroom, 3-bathroom residence offers 2,312 square feet of comfortable and stylish living space ideally designed for modern and multigenerational lifestyles. The recently remodeled primary suite is a true retreat, featuring new carpeting and tile flooring, dual granite vanities, an oversized walk-in shower with modern, upgraded fixtures, a new water closet, and thoughtful contemporary finishes throughout. Inside, you’ll find timeless architectural charm which includes a formal dining room, three spacious living areas, louvered window shutters, and elegant hardwood flooring. One of the living spaces is highlighted by a stunning brick fireplace overlooking the beautiful private pool area and fully fenced backyard — creating the perfect setting for entertaining, family gatherings, or simply unwinding in your own backyard oasis. In addition, this spectacular residence also boasts tasteful landscaping touches for exceptional curb appeal, a large two-car garage with electric opener, a newer shingle roof replaced in late 2023, and fresh interior paint throughout the home. Ideally located near Winter Park Pines Golf Club, Cady Way Trail, Ward Park, Showalter Field, tennis and pickleball courts, top-rated schools, and the many shopping and dining destinations of Park Avenue and historic downtown Winter Park. Don’t miss this rare opportunity to own a true Winter Park gem — schedule your private showing today!

Listing is courtesy of: DAHLIA REALTY GROUP (689-777-4111)

Listing Agent: Chuck Tolfa (407-782-3518)

Remarks: Under contract-accepting backup offers. ***UPDATED & REFRESHED!! All new ceiling fans, light fixtures, smoke detectors, gutters and screens, foliage, window blinds and paint.*** Discover the perfect blend of value, location, and versatility in Winter Park's best-kept secret - the Eastbrook neighborhood. This 3-bedroom, 2-bathroom home is ideal for homebuyers looking to make new memories or savvy investors seeking a turn-key property with proven rental income. MOVE-IN READY: From the moment you step inside this roomy, open floor plan, it's ready to enjoy. The heart of the home - kitchen, dining and living room - is tastefully renewed and has plenty of space. The ample primary bedroom has a full ensuite bathroom and large windows. Two additional roomy bedrooms share a full guest bathroom. The separate laundry room is spacious and perfect for a hideaway office. Outdoor enthusiasts will love the massive, fully fenced backyard, including firepit for chilly Florida nights and "grass-covered" patio. This private oasis is ready for pets, play, or future expansions. Bonus features include carport and multicar driveway with lots of elevated storage, and an additional cross-fenced and gated side yard. RECENT FUNCTIONAL IMPROVEMENTS: New water heater, thoroughly serviced AC unit, exterior paint, and recently inspected roof and electrical panels. SELLERS ARE MOTIVATED with a price well below area comparables. Investor Advantage: This property has served as a high-performing, low-maintenance rental for seven years. Location: Quiet, safe, and walkable Eastbrook, with shopping less than a mile away. Condition: Well-maintained with modern updates. Don't miss your chance to own a piece of Winter Park at an unbeatable price.

Listing is courtesy of: SAVVY AVENUE, LLC (888-490-1268)

Listing Agent: Moe Mossa (888-490-1268)

Remarks: A distinctive offering where design, location and performative upgrades come together seamlessly. One of the original modern homes in Winter Park, this iconic residence has been thoughtfully reimagined through a designer-led renovation that emphasizes clean lines, natural light, easy maintenance and high durability. The result is a bright, refined space that balances architectural character with modern comfort. A flexible two-level layout offers main living areas on the first floor, complemented by an upper-level studio or retreat space with optional deck access, ideal for today’s lifestyle. Extensively improved with over $260,000 in recent upgrades, the home was enhanced with durability and efficiency in mind. Major improvements include a commercial-grade TPO roofing system with advanced drainage and a 20-year warranty completed in 2024, as well as hurricane-impact aluminum sliders all around with large missile-rated glass and enduring waterproofing. Additional features such as a white reflective roof, whole-house surge protection, updated electrical components, and a new code-compliant deck railing further elevate the home’s long-term value and performance. The outdoor spaces have been equally curated, with mid-century-inspired landscaping designed for beauty and ease of maintenance. Palms, agave and drought-tolerant plantings create a clean, modern aesthetic, while redesigned yard spaces enhance openness and usability. A professionally landscaped east yard, low-maintenance turf on the west side, a five-zone irrigation system, and private well irrigation contribute to a thoughtfully executed exterior environment. An expanded driveway provides ample parking, and outdoor lighting enhances ambiance and function. Just moments from desirable Park Avenue, this architecturally significant modern residence is ideally in one of Winter Park’s sought-after neighborhoods, near Lake Virginia, Rollins College and Winter Park Tennis Center. Set on a quiet, tree-lined corner lot with no through traffic, the home enjoys an elevated position on a natural rise, offering peace of mind with no history of flooding, along with ideal north-facing orientation and beautiful natural light throughout the day.

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

Listing Agent: Audra Wilks (407-252-8582)

Remarks: Welcome to this thoughtfully updated Winter Park home ideally on a spacious corner lot with a two-car garage offering excellent storage and everyday convenience. This home offers a flexible layout featuring two bedrooms plus an office that can function as a third bedroom, ideal for working from home or accommodating guests. Hardwood floors run throughout, adding warmth and character. Major system updates have been completed, including a 2024 metal roof and 2025 HVAC system, providing peace of mind for the next owner. Additional exterior improvements include new soffits and gutters, fresh exterior paint in 2025, a whole-home surge protector, and updated breezeway or office door and windows installed in 2024. Inside, you will find a well-equipped kitchen with Samsung appliances, including a range, microwave, dishwasher and a 2023 refrigerator, along with a 2020 Samsung washer and dryer. Comfort and efficiency have also been enhanced with replaced air ducts in 2016, an Ecobee smart thermostat and updated ceiling fans. Smart home features include a Logitech Circle View wired doorbell, smart blinds and updated smoke detectors, providing modern convenience throughout the home. The property sits toward the rear of the lot, creating a private, fenced yard space ideal for pets, outdoor enjoyment or entertaining. An irrigation system is also in place to help maintain the landscaping. In the desirable Winter Park area and zoned for highly regarded Winter Park schools, this home offers a combination of location, updates and flexibility. With major systems addressed, this home presents a move-in-ready opportunity and being sold as is.

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

Listing Agent: Audra Wilks (407-252-8582)

Remarks: Discover comfort and convenience in this charming, spacious 2-bedroom, 2-bath residence nestled in the heart of Winter Park! Step inside to an inviting living room with a vaulted ceiling. The fully equipped open-floor kitchen, featuring ample roomy cabinets, is perfect for everyday living and entertaining. The thoughtfully designed split floor plan enhances functionality and privacy. Elegant, durable flooring throughout the home ensures easy maintenance. Enjoy the walk-in shower and bathtub with upgraded plumbing and tile. A convenient coffee nook sits just off the kitchen. The spacious patio is ideal for entertaining guests and enjoying outdoor time. Community amenities include a swimming pool and tennis courts, supporting a low-maintenance, active lifestyle.

Listing is courtesy of: SAND DOLLAR REALTY GROUP INC (407-389-7318)

Listing Agent: Robert Arnold, Jr (407-389-7318)