Winter Park Homes For Sale & Real Estate - 342 homes

Remarks: One or more photo(s) has been virtually staged. Welcome to 1036 Aragon Avenue, a charming Winter Park bungalow perfectly positioned in one of Central Florida’s most sought-after locations. Nestled along picturesque cobblestone roads and surrounded by mature, tree-lined streets, this move-in ready home captures the character and warmth that make Winter Park real estate so desirable. Located just one mile from Park Avenue, SunRail, and Rollins College, and only half a mile from Hannibal Square, local parks, and the Winter Park Library, this property offers an unbeatable blend of convenience, walkability, and lifestyle. As you step inside, you are greeted by a modern open floor plan enhanced with luxury vinyl plank flooring that flows seamlessly throughout the home. The spacious living and dining areas create an inviting environment ideal for both everyday living and entertaining. The updated kitchen serves as the heart of the home, featuring stainless steel appliances, granite countertops, and timeless white shaker cabinetry. Its thoughtful layout allows for easy conversation and connection while preparing meals, making it as functional as it is stylish. The oversized great room provides flexibility for relaxing, hosting guests, or creating a dedicated workspace. Both bedrooms are generously sized, offering comfort and versatility. The owner’s bedroom is especially appealing, complete with a custom closet organizer and direct access to a private paver patio—an ideal setting to enjoy Florida’s year-round sunshine. The bathroom has been tastefully updated with granite countertops and a shower/tub combination accented by classic white subway tile, creating a clean and timeless aesthetic. Outdoors, the secluded backyard offers privacy and future potential, with room to expand or customize according to your vision. Whether you are searching for a primary residence, a downsizing opportunity, or an investment in the heart of Winter Park, this property presents a rare chance to own a beautifully updated home in a prime location. Experience the charm, convenience, and lifestyle that 1036 Aragon Avenue has to offer. Schedule your private showing today.

Listing is courtesy of: WATSON REALTY CORP (407-359-2300)

Listing Agent: Tim Veigle (407-399-0879)

Remarks: Under contract-accepting backup offers. Welcome to a rare gem in one of Winter Park’s most sought-after neighborhoods, Brookshire Heights—where trees line the street and the mailman still delivers right to your front door. Perfectly positioned with the scenic and wooded Cady Way Trail in your backyard, this custom-built 2022 residence offers over 2,100 square feet of thoughtfully designed single-story living, where refined style meets everyday ease. A desirable open-concept floor plan showcases three bedrooms and two bathrooms, enhanced by wood-look plank tile flooring, soaring ceilings and doorways, crown molding, and recessed lighting throughout. Expansive sliding glass doors with electric retractable blinds and transom windows flood the home with natural light, creating a seamless connection to the covered, screened lanai—perfect for effortless indoor-outdoor living and sophisticated entertaining. The beautifully appointed kitchen is both striking and functional, featuring crisp white shaker cabinetry complemented by a contrasting gray island with seating for four, all topped with sleek white quartz countertops. A dedicated wine and beverage bar with a built-in refrigerator adds an elevated touch, while stainless steel appliances and a spacious pantry ensure everyday convenience. Bathed in natural light, the dining area offers an inviting and elegant setting for both intimate gatherings and larger-scale entertaining, with expansive windows that bring the outdoors in. The primary suite serves as a serene retreat, complete with private lanai access for a tranquil indoor-outdoor connection. A generously sized custom closet provides ample storage, while the spa-inspired bathroom features a timeless clawfoot soaking tub, honeycomb tile flooring, an expansive walk-in shower, and a dual quartz vanity—creating a luxurious, resort-style experience. Two additional bedrooms offer flexibility for guests, family, or workspace, including one with stylish built-in shelving. A beautifully finished hall bath reflects the same elevated design and attention to detail found throughout the home. Designed with functionality in mind, the well-appointed laundry room features built-in cabinetry and a hanging bar, provides convenient access to both the primary suite and main living areas. A spacious 2.5 car garage allows plenty of room for storage, a golf cart or other toys. Ideally located, this residence offers convenient access to premier institutions including University of Central Florida, Rollins College, and Full Sail University. Enjoy nearby recreation at Winter Park Pines Golf Club and Cady Way Park, featuring a pool, playground, tennis and pickleball courts, and beach volleyball. Spend weekends boating from Dinky Dock Park onto the renowned Winter Park Chain of Lakes, or explore the charm of Park Avenue with its boutique shopping and fine dining. Everyday convenience is enhanced with close proximity to AdventHealth Winter Park and the Crosby Wellness Center, along with easy access to Orlando International Airport. Zoned for top-rated schools including Brookshire Elementary School, Glenridge Middle School, and Winter Park High School, this exceptional property seamlessly blends lifestyle, location, and lasting value. Roof - 2022, HVAC - 2022, Electrical - 2022, Plumbing - 2022, Water Heater - 2022

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

Listing Agent: Amy Turner (407-803-3885)

Remarks: 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. Minutes from Park Avenue and Downtown Winter Park's incredible restaurants and fantastic shopping, Rollins College, UCF, AdventHealth Winter Park, Downtown Orlando, and more. At $460,000 in 32789, this one won't last.

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

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

Remarks: One or more photo(s) has been virtually staged. Step into refined lakeside living at the exclusive Lake Killarney Townhomes, where contemporary elegance meets everyday convenience. This ultra-private corner unit boasts one of the community’s most desirable floor plans—perfectly positioned in a peaceful enclave just steps from the vibrant heart of Winter Park Village and mere minutes from I4, offering seamless access to downtown Orlando and beyond. Designed for the modern lifestyle, this stunning residence features an open-concept layout with soaring ceilings, oversized windows, and luxury finishes throughout. The sleek chef’s kitchen anchors the space, showcasing dramatic gray cabinetry, a bold black center island, and a high-end Samsung appliance package, complete with a natural gas cooktop and built-in wall oven. Quartz countertops and a full-height backsplash give a seamless, refined look, while a spacious walk-in pantry adds everyday convenience. Upstairs, three generously sized bedrooms each pair with a spa inspired bathroom deliver elevated comfort. Each bath is thoughtfully designed with floating vanities, designer porcelain tile, and custom closet systems—bringing a boutique hotel aesthetic to your personal retreat. Enjoy quiet mornings or golden-hour gatherings on the expansive private terrace, framed by glass railings and pre-plumbed for a future summer or cocktail kitchen—perfect for effortless indoor-outdoor entertaining. Residents enjoy exclusive access to lakefront pavilion, and an array of watersport amenities including kayak, paddleboard, and canoe storage. With everything Winter Park has to offer just moments away, this location offers the perfect blend of serenity and connectivity.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Brandon Geers (941-928-5152)

Remarks: Step into this stunning West-Indies inspired luxury home crafted by Nautilus Homes, where tropical charm meets timeless elegance. An architectural masterpiece in the heart of City of Winter Park. This five-bedroom seven-bath home that includes a private in-law suite offers plenty of exquisite interior features. The home welcomes you with a beautifully designed 16 ft wide circular driveway wrapped in upgraded pavers, offering both elegance and functionality. A very rare 4-car garage in Winter Park with two in the rear and two in the front of the home. Starting with entering through massive 10 ft. double iron doors flowing into the foyer with 11ft high ceiling beginning with the flex/office room and formal dining to your left and right. Followed by entering the gallery that leads to the great room. The Chef’s Kitchen, a culinary dream featuring an oversized center island, quartz countertops throughout, custom 42"+15" wood cabinetry, a custom walk-in pantry, and top-of-the-line Thermador professional series. That Includes a 48' refrigerator, 48" gas cooktop, custom hood, dishwasher, built-in microwave, double convection ovens and built in coffee station. On your way to the formal dining, you pass by the show-stopping, Tempered glass wine room. Its crystal-clear glass enclosure offers a striking view of your curated collection, while the built-in wine chiller ensures each bottle is perfectly preserved. This elegant transition creates a seamless blend of function and sophistication, setting the tone for unforgettable dining experiences just steps away. The primary suite offers tranquility peace of mind, and the primary bath has a spa-like oasis with a spacious shower stand-alone tub. Followed by a custom closet thoughtfully design with plenty of room and storage. The guest retreat area has a huge bedroom, access to a full bath including private access to the Lania and pool. Tucked away with its own private entrance attached to the rear garage, the in-law suite above the garage offers the perfect blend of comfort and independence. This thoughtfully designed space includes a full bath, a cozy living area, and a convenient space with a kitchenette—ideal for extended stays or multi-generational living. Make your way to the second floor that has 11ft ceilings as well. As you reach the top the space opens into a massive game room with a wet bar, perfect for entertainment retreat with a balcony. All second-floor bedrooms have a thoughtfully design with a full bath for privacy. As you make your way back downstairs to outside, step through the oversized sliding glass doors and into your private outdoor oasis. Effortlessly extending your living space into the open air. Just beyond, the sparkling gas heated/saltwater pool and spa framed by lush landscaping and designed for both relaxation and recreation. Also, the fully equipped summer kitchen features gas grille, beverage refrigerator and ample counter space—perfect for alfresco dining and effortless entertaining. This seamless indoor-outdoor flow creates the ultimate setting for enjoying the Florida lifestyle in style and comfort. This masterpiece is equipped with a full irrigation system around the home, exterior lighting, exterior cameras for security. Smart home system ready for lighting, music and security controlled by Control 4 system for your convenience. Interlachen Golf community less than 5 min, Phelps Park walking distance, Park Ave 10 min and restaurant and retail minutes away.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Prentice Williams (321-438-8955)

Remarks: This stunning new contemporary residence, a five-bedroom, five-and-a-half bath home by the renowned Rex-Tibbs Development, a custom builder for over 40 years, continues to set the standard for luxury living. Perfectly situated on a premium, quiet, charming brick street, the home blends clean architectural lines with timeless finishes and thoughtful design details. An elegant foyer immediately introduces the home’s refined aesthetic, offering a direct line of sight to the gorgeous herringbone white oak floors in the great room and the sparkling pool just beyond the full glass doors. Anchored by a sleek linear gas fireplace with custom built-ins and floating shelves, the great room provides an inviting yet sophisticated gathering space. The open-concept chef’s kitchen is a showpiece in both form and function. Outfitted with Wolf and Sub-Zero appliances, it boasts an eight-burner range with one-and-a-half ovens, an oversized Sub-Zero French door refrigerator with a freezer drawer, a built-in microwave drawer, and a walk-in pantry featuring a wine and beverage tower. Marble counters in all baths continue the home’s commitment to refined finishes. The main level primary suite is a serene retreat with a spa-inspired bath featuring a large glass-enclosed shower, separate soaking tub framed by dramatic four-by-ten-foot porcelain slabs, a custom walk-in closet, and a private water closet. A flexible fifth bedroom with an ensuite bath offers the perfect option for an office or den. A striking glass-railed staircase leads to the second level, where a spacious lounge area opens to a private covered patio. Three additional ensuite bedrooms, each with custom closet systems, complete the upstairs living quarters. Designed for indoor-outdoor living, the expansive covered lanai includes a summer kitchen with a grill, hood vent, refrigerator, sink, and a dedicated half bath. Overlooking lush landscaping with tropical Clusia hedges and Foxtail palms, the brand-new pool is finished with designer tile that lends a stylish, resort-quality flair. Additional highlights include a spacious storage closet under the staircase, oversized two-car garage, 500-gallon propane tank for easy generator connection, stone paver driveway and durable metal roof. Wonderfully located in a picturesque neighborhood, the property is just minutes from the boutiques and dining of Park Avenue, top-rated public and private schools and offers convenient access to downtown Orlando, the attractions, as well as area airports. A rare opportunity to own a newly constructed home of such quality and craftsmanship in one of Winter Park’s most sought-after neighborhoods.

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

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

Remarks: Private, gated lakefront living on Bear Gully Lake one of Winter Park’s most desirable spring-fed ski lakes. Set on an expansive 137-acre body of water, this custom residence offers a rare combination of privacy, scale, and true Florida waterfront lifestyle. A circular driveway behind a private gate welcomes you to a thoughtfully renovated home designed to capture sweeping lake views. Bear Gully Lake is spring-fed and open to water vehicles, making it ideal for boating, water skiing, wakeboarding, tubing, fishing, and year-round enjoyment. The lakefront experience is exceptional, featuring a fully equipped dock with power, covered boat lift, and sun deck, perfectly positioned for enjoying stunning sunsets. Outdoor living is a highlight of the property. The expansive lanai and pool area overlook the lake and are ideal for entertaining, complete with a renovated summer kitchen featuring a grill, sink, mini refrigerator, and granite countertops. The oversized backyard provides ample space for gatherings, recreation, and pets. Inside, the home opens to a dramatic great room with vaulted ceilings, a striking stacked-stone feature wall with custom built-ins, and large sliding glass doors that fully retract to create seamless indoor-outdoor living. The space was reimagined during extensive renovations to maximize natural light and lake views. The chef’s kitchen, redesigned by award-winning designer Sandra Agurto of CCI, features all-wood cabinetry, quartz countertops, contemporary backsplash, oversized island with beverage and wine refrigerators, induction cooktop, convection ovens, and a separate full refrigerator and freezer, with abundant custom storage throughout. The primary suite is privately located in its own wing and offers serene lake views, high ceilings, and a spa-style en-suite bath renovated in 2022 with soaking tub, walk-in shower, expansive custom vanity, upgraded lighting, and private water closet with bidet. A large walk-in closet with custom built-ins completes the suite. All bedrooms feature their own bathrooms and walk-in closets, providing exceptional privacy and flexibility, with three full en-suite bedrooms ideal for guests or multigenerational living. Additional flexible spaces include a gym or bonus room suitable for formal living, dining, or a game room. Recent upgrades include a new roof (2018), new hot water heater (2024), fully fenced yard, Russound sound system, updated security system, new pool deck pavers, and a rebuilt dock with Trex decking and updated boat lift components. The home is part of a lake association with no mandatory dues, providing community updates and seasonal events such as the holiday boat parade. Conveniently located near SR-417, UCF, downtown Winter Park, and Trinity Prep, this is a rare opportunity to own a true spring-fed lakefront home on one of Winter Park’s most coveted lakes.

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

Listing Agent: Keigan Lewis (305-393-8683)

Remarks: This custom home is nestled in an up-and-coming neighborhood in Winter Park. This stunning home redefines modern living. Designed with an open floor plan, it seamlessly blends spaces to create a harmonious flow, perfect for both entertaining and everyday life. The abundance of windows bathes the interiors in natural light, creating a bright and airy ambiance. The office/study is set apart for quiet pursuits. The chef’s kitchen opens naturally to the great room and boasts a large island, top-of-the-line Thermador appliances, complemented by the sleek quartz countertops that offer both style and functionality. Conveniently equipped with two sets of washers and dryers, this home ensures efficiency and ease for the busiest of households. Retreat to the master suite, where luxury meets serenity. A massive walk-in closet provides ample storage, while the spa-like master bath invites relaxation with its elegant design and premium features. The indoor outdoor flow is easy with the huge set of glass sliders leading to the covered porch equipped with drop down screens. Enjoy the summer kitchen and sparkling pool while entertaining family and friends. This home is a true gem that combines thoughtful details with sophisticated style.

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

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

Remarks: Welcome to this well-maintained three-bedroom, two-bathroom home offering 1,574 square feet of thoughtfully designed living space in the established and highly desirable Howell Estates neighborhood of Winter Park. From the moment you enter, an abundance of natural light, ceiling fans throughout, and a functional layout create an open and inviting atmosphere. The flexible floor plan includes a dedicated family room/den in addition to a formal dining area, providing versatile space for entertaining, working from home, or everyday living. Blinds throughout, generous closet space, and sliding glass doors leading to the backyard add both comfort and practicality. The kitchen blends classic style with everyday convenience, featuring blond-toned wood cabinetry, a closet pantry, and newer stainless steel appliances including a refrigerator, dishwasher, and microwave(2024). The layout connects seamlessly to the surrounding living spaces, making it ideal for both daily use and hosting. The primary suite serves as a private retreat, complete with a ceiling fan and an ensuite bathroom featuring a single vanity, a tiled walk-in shower with glass sliding doors, and a newly updated toilet. The two additional bedrooms are well-sized and versatile, perfect for family, guests, or a home office, and share a hall bathroom with a single vanity, tiled tub/shower combination, and a new toilet. Outdoor living is enhanced by a spacious and open 0.24-acre fully fenced lot, offering plenty of room for relaxation, entertaining, or future additions. The exterior has been freshly painted and features brand-new landscaping completed in 2026, creating excellent curb appeal. A two-car garage with a new garage door provides additional convenience and storage. Significant updates offer peace of mind, including a roof installed in 2020, electrical updates completed in 2020, HVAC system installed in 2017, and a water heater replaced in 2023. Ideally located, this home is just 7 minutes from Red Bug Lake Park, close to top-rated schools, and within close proximity to restaurants, grocery stores, and retail shopping—offering the perfect blend of comfort, convenience, and location. Roof – 2020 | HVAC – 2017 | Electrical – 2020 | Water Heater – 2023

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

Listing Agent: Amy Turner (407-803-3885)

Remarks: One or more photo(s) has been virtually staged. This luxurious Modern Style home epitomizes maintenance-free living, featuring a premium solar system you own outright, paying for your electricity. (Ask to see the bill.) Imagine relaxing on your private, expanded lanai, soaking in the breathtaking sunsets. Your spacious 4-bedroom, 3.5-bathroom home offers premium views of nature, and is just steps away from the community resort clubhouse. With gated access, Hawks Crest Residence enjoy an abundance of amenities, including a resort pool and fitness center, sidewalks and playgrounds throughout. And for those seeking adventure, enjoy dock access to Lake Howell, complete with a canoe/kayak launch. Daily, residents can relax and unwind while the management association takes care of all landscaping around the home, ensuring that residents can enjoy true maintenance-free living. The state-of-the-art off-grid solar system is equipped with battery backup with a 30-year warranty transferable to new owners. And this home is pre-wired for electric vehicles with room to expand. Excess power produced is sold back to the power company through the “Net Metering” program. Additionally, upgrades include heavy-duty commercial luxurious vinyl wide-plank flooring, two power monitoring systems, a whole-house water softener & filter system, along with 8-foot doors all designed for comfort, convenience and a peaceful home where you can relax. Nestled in this spacious home, you’ll find 20-foot-high ceilings and breathtaking views of the illuminated fountain from various rooms, creating a serene and relaxing atmosphere you’ll enjoy, even from the kitchen sink. And with a smart-winch lift, your chandelier maintenance is a breeze. (Rated up to 200lbs) Uniquely designed, this home was built to withstand extreme weather conditions, featuring concrete/granite tile roof, along with a steel reinforced, concrete-filled block walls and slab, all anchoring to the foundation that uniquely ties everything together, ensuring the utmost strength and safety for your family. Owners have meticulously maintained this home and comes with floor plans, a complete set of blueprints, along with photos of the home during the building process, and even includes documents for all equipment and appliances. The premium solar system comes with a 30-year warranty, including scheduled updates like the new power panel, installing April 2026. And yes, the warranty is transferable to new owners. This home features a split floor plan, with a primary bedroom on the first floor and a second primary bedroom upstairs. Spanning 2,589 square feet, the home also includes an additional 540 square feet of screened-in lanai (18x30), providing a private outdoor space to enjoy sunsets while overlooking the resort water features and landscaping. Schedule a showing for your buyers today!

Listing is courtesy of: BHHS FLORIDA REALTY (352-729-7325)

Listing Agent: Rod Chevalier (352-729-1818)

Remarks: 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: Under contract-accepting backup offers. Come see this charming pool home on a desirable corner lot near Lake Killarney in Winter Park. This beautifully maintained mid-century residence features 3 bedrooms and 2 baths with warm wood floors and timeless character throughout. The private, fully fenced backyard is turfed for low maintenance and perfect for relaxing and entertaining. Major updates provide peace of mind, including new windows (2019) a renovated primary bedroom and bath (2019), new septic drainfield (2023), tankless water heater (2019), new refrigerator (2024) and in ground pool converted to saltwater in 2023. A rare opportunity to own a classic Winter Park home in beautiful condition with modern improvements and exceptional outdoor living. Walk to Hunger Street Tacos, Lombardi’s Seafood and Creative Jane Art Studio while being conveniently located near 1-4, College Park and Winter Park. Come see this gem!

Listing is courtesy of: ANNE ROGERS REALTY GROUP INC (407-649-4141)

Listing Agent: Arden Magee (407-276-1698)

Remarks: One or more photo(s) has been virtually staged. 4.99% INTEREST RATE OFFERED FOR QUALIFIED BUYERS! This low-maintenance Winter Park condo just became even more affordable ... and it truly checks all the boxes! Enjoy single-story living with no neighbors above or below, corner-unit privacy, a screened patio overlooking the spacious courtyard, updated kitchen and baths, and major mechanical updates already taken care of. Add in a community pool, sidewalks, pet stations, and an unbeatable Winter Park location - and this 2-bedroom, 2-bath condo offers the ideal combination of comfort, convenience, privacy, and value. Inside, you’ll find a functional split-bedroom floor plan, spacious living and dining areas, indoor laundry, and a screened patio that adds valuable outdoor living space. The one-story layout offers easy everyday living, while the corner-unit location provides added privacy and a more desirable setting within the community. The flexible floor plan works well for everyday living, guests, roommates, or even a home office setup. Located in a community with a pool and situated near shopping, dining, major roadways, and daily conveniences, this property offers easy access to University of Central Florida, Full Sail University, SR-417, FL-436, Downtown Winter Park, and Downtown Orlando. Whether you are searching for a primary residence, a first home, or a low-maintenance property in a central location, this home checks all the boxes. The special financing rate equates to a savings of approximately $213 per month for qualified buyers! Now more than ever, if you’ve been searching for an affordable, easy-maintenance, Move-in Ready property in Winter Park ... this is your sign! Seller offering an incredible savings to help you on your path to homeownership. Terms and conditions apply. Call for details.

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

Listing Agent: Allison Day (407-617-2881)

Remarks: Under contract-accepting backup offers. Set on over half an acre in Winter Park’s coveted Orwin Manor, this 1935 French Provincial estate offers a rare blend of architectural character, modern system updates, and extraordinary future potential. The property offers the unique opportunity to own an estate in a beautifully historic Winter Park neighborhood. Whether thoughtfully renovated, expanded, or reimagined, this property stands as a truly special opportunity in one of Winter Park’s most desirable neighborhoods. A charming brick path leads to a welcoming covered front porch and into a light-filled living room featuring original cypress beams with iron strapping, vaulted ceilings, and a dramatic fireplace crowned by the home’s original bronze chandelier. Glass doors open to a delightful sunroom and a central hallway with abundant storage, and a convenient half bath. The private primary suite is tucked away and offers a peaceful retreat with vaulted ceilings, ceiling fan, wood floors, a wall of closets, and a newly renovated 2023 bath featuring an oversized deep soaking tub and marble vanity. A second ensuite bedroom includes a designer bath with a large glass shower, rain head, and wand. An oversized third bedroom—currently used as a family room—features a vaulted tongue-and-groove ceiling with beams, a walk-in closet, and glass sliders opening to the brick patio and expansive grounds. The dining room and breakfast area flow seamlessly to outdoor living spaces, creating an effortless indoor-outdoor connection. The renovated kitchen includes a farmhouse sink, gas cooking, butcher block countertops, and access to a private walled rose garden and extensive parking options. A newly covered kitchen entrance with custom terrazzo flooring with inset marble pattern leads to a laundry room and versatile studio or workshop with built-ins. Throughout the home, an abundance of windows frames peaceful green views and fills the space with natural light. Outdoors, enjoy raised garden beds, multiple brick patios with fountains, ceiling fans, and partial coverings—perfect for entertaining or quiet reflection. Separate outbuilding is dry, plumbed and wired with a workshop, a large storage space ideal for future ADU and 2-car carport. With major system improvements already completed and an oversized lot offering flexibility for renovation, expansion, new construction, or potential lot division (buyer to verify), this is a legacy property with limitless possibilities. Major system improvements include a 2021 roof & tankless water heater, full re-plumb in 2023, replacement of all major under-home trusses, three updated electrical panels, two HVAC systems (2014 & 2019), providing modern efficiency while preserving the home’s original character. See MLS#O6374414.

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

Listing Agent: Lisa Gould (407-721-7612)

Remarks: One or more photo(s) has been virtually staged. Set on a prized corner lot in Winter Parks sought after Orwin Manor Neighborhood, 1651 Westchester Ave is a timeless classic with Cape Cod inspired architecture that has been meticulously reimagined with today’s luxury finishes while preserving its original charm. Refinished Original Pine hardwood flooring and a beautifully updated fireplace welcome you into the main living space, while the showpiece kitchen delivers true chef-level design with new Custom European Cabinetry, Quartz Countertops with a Waterfall Island, Porcelain Tile floors, premium lighting, under counter Kitchen Aid Ice Maker and a top-tier appliance suite including Wolf Gas Range-top, Wolf Built-in Oven & Microwave and Bosch Refrigerator and Dishwasher. The primary suite is a serene retreat with a newly redesigned spa style bath with frameless walk-in shower, soaking tub, new double sink vanity and lighting—plus a walk-in closet with California Closet built-in’s and a versatile bonus room ideal for a sitting area, nursery, or dedicated laundry space. Outdoors, enjoy resort-style living under the expansive 26’ x 24’ covered Lanai featuring vaulted tongue-and-groove ceilings, tile flooring, a striking stone gas fireplace with RealFyre burners, stainless mantle, perfect for effortless entertaining. There is even enough room to customize the outdoor space with your own Pool Oasis. Recent improvements include a re-roof 2020, HVAC System, Double-Pane windows, 4-panel slider & front door, fresh interior/exterior paint, new custom shades, privacy bamboo landscaping, privacy fencing and an extended paver driveway. The attached Garage offers dedicated storage space and a bonus room with mini-split system which could offer space for home gym or office. Just minutes from Park Avenue’s acclaimed dining and shopping, top Winter Park amenities, Advent Health Medical Campus and quick access to key corridors for an easy downtown Orlando commute, this is 32789 living at its most refined—classic architecture, modern systems, and elevated indoor-outdoor lifestyle in one of Winter Park’s most sought-after neighborhoods.

Listing is courtesy of: SERHANT (786-296-8626)

Listing Agent: Shawn Layton (321-514-8055)

Remarks: Under contract-accepting backup offers. Steeped in history and masterfully reimagined, this 1926 Winter Park estate blends architectural provenance with modern refinement. Thoughtfully restored by E2 Homes, the residence honors its past while offering contemporary sophistication. Unlike many historic properties, it is free from preservation restrictions, allowing for seamless enhancements. On the shores of Lake Virginia along the desirable Winter Park Chain of Lakes, this 3,181-square-foot estate features four bedrooms, three full baths and two half baths, with three bedrooms in the main house plus a detached one-bedroom guest cottage. The second-floor primary suite is a private retreat with a Juliet balcony, dual closets and an elegantly appointed bath with an expansive dual-sink vanity, a separate water closet, and a washroom with a shower-tub combination. A Jack and Jill bath, adorned with Maharam wallpaper, serves the additional upstairs bedrooms. The Poliform Twelve kitchen showcases European craftsmanship with Gaggenau and Sub-Zero appliances, sleek Italian cabinetry and natural basalt countertops. The formal dining room, framed by arched windows and French doors, opens to a vine-covered courtyard, while the sunroom offers uninterrupted lake views. A fireplace in the living room, flanked by custom built-ins, adds warmth to the home’s contemporary aesthetic. Beyond its striking interiors, the estate is an architectural rarity, featuring original woodwork by Gene Leedy, a key figure in the Sarasota School of Architecture. The home is crowned with sought-after Ludowici-Celadon Imperial roof tiles. Poliform built-ins extend throughout, including a dedicated upstairs office/library. An integration of art and architecture, the property features site-specific installations by acclaimed artist Matt Olson. His No Separation project finds a compelling continuation here. The entryway, designed by Olson’s firm OOIEE and inspired by Sol LeWitt, makes a striking first impression. Designed for seamless indoor-outdoor living, the estate’s exterior spaces are as refined as its interiors. A covered deck overlooks a heated saltwater pool. A wood-clad pergola shelters the lanai. The boathouse includes a partial bath, creating a waterfront sanctuary. A Sonos-integrated sound system extends from the main house to the patio, guesthouse and boathouse, ensuring a seamless sensory experience. The detached guesthouse is a private retreat with a full bedroom, bath, kitchenette and Poliform built-ins. Floor-to-ceiling windows frame manicured grounds and lake views, while a private covered porch provides a tranquil space for relaxation. Every detail has been meticulously curated, from designer lighting to motorized roller shades and a wood-burning fireplace anchoring the living room. A private wine library enhances the home’s sophisticated appeal. Meticulously maintained by E2 Concierge services, the residence undergoes routine wellness checks and meticulous upkeep. A distinctive home of this caliber is rarely available, a residence where history, architecture and art converge in harmony. This is a once-in-a-lifetime opportunity to own one of Winter Park’s architecturally and artistically significant properties.

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

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

Remarks: Charming 3-bedroom, 2-bath home in the heart of desirable Winter Park. Bright and inviting layout with comfortable living spaces and plenty of natural light. Enjoy a private backyard perfect for relaxing or enteraining. Conveniently located near shopping and dinning.

Listing is courtesy of: INT'L PROFESSIONAL REALTY INC (407-699-7718)

Listing Agent: Lorena Ortega (407-256-3631)

Remarks: This property located in a peaceful community IN WINTER PARK. and easy access to FL I-4 , short drive distance to Rollins College, UCF, Valencia college, Hospitals, shopping center, restaurants and Orlando Theme Park. This unit located on the second floor, it has 3 bedrooms 2, bathrooms, open floor plan. The community amenities include a large pool with lounge chairs, playground and gazebo. This property can be leased. You must see for any possibilities come and check for yourself. Registered owner is brother of the realtor. SELLER MIGHT HOLD FIRST MORTGAGE WITH A GOOD DOWN PAYMENT.

Listing is courtesy of: PRIMESTATE REALTY, INC. (407-850-9494)

Listing Agent: Hoover Yap (407-342-9395)

Remarks: Welcome to this lovely open-concept 2 bedroom, 1 bathroom condo, perfectly situated in a fantastic area close to plenty of shopping, dining, and everyday conveniences. Ideal for first-time buyers, downsizing, or investors looking for a solid opportunity! This property highlights an open-concept bright interior with great natural light living and dining area. Two spacious bedrooms with 1 bathroom. Durable vinyl flooring with cozy carpeted bedrooms with a spacious walk in in closet in the primary bedroom. You will get a private balcony — perfect for morning coffee or evening relaxation and the convenience of your our laundry with washer and dryer hookups included. This condo is perfectly located in a desirable area of Winter Park close to tons of and amenities. Currently being rented for $1550/month

Listing is courtesy of: LOKATION (954-545-5583)

Listing Agent: Brandy Ray (949-449-5652)

Remarks: Beautifully updated 4-bedroom, 2-bath home in a premium Winter Park location with NO HOA and a spacious backyard. This home is currently in the final phase of renovation and has already undergone major upgrades, including remodeled bathrooms, updated kitchen, new flooring, upgraded electrical, and a newer roof. The interior has been thoughtfully modernized, offering a bright open layout ideal for comfortable living and entertaining. Seller is offering $20,000 toward remaining exterior improvements and future A/C replacement if desired; current A/C is functioning. An excellent opportunity for a buyer looking for a substantially renovated home with room to finalize a few exterior touches. Conveniently located near shopping, dining, schools, and major roadways. SELLER MOTIVATED!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Arlenys Oviedo (786-803-4342)