Homes For Sale in Winter Park 32789 - 234 homes

Remarks: Pre-Construction. To be built. This is your final opportunity to build a custom home in one of Winter Park’s most sought-after pockets. Set on a 6,748 sq ft lot, this brand-new 4-bedroom, 3.5-bath residence offers 2,662 sq ft of thoughtfully designed living space, blending clean modern architecture with the comfort and functionality today’s buyers expect. Crisp lines, open-concept living, and intentional design create a home that feels both elevated and livable. What makes this opportunity truly unique: this is the last remaining homesite within a curated collection of three custom builds—each thoughtfully designed with its own architectural identity, yet unified in creating a refined, cohesive streetscape. The other two homes are already underway, making this your only chance to secure a position in this limited offering. Located just 6 minutes from Park Avenue, you’re moments from Winter Park’s best—boutique shopping, award-winning dining, and everyday conveniences—while also being close to top-rated hospitals and major thoroughfares. Offered as a custom build, this home allows you to tailor finishes, selections, and details to match your vision. Pricing reflects the base build, with upgrade options available to create a fully personalized end product. With new construction opportunities in 32789 at this price point becoming increasingly scarce, offerings like this are few and far between—especially with the ability to fully customize your home from the ground up.

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

Listing Agent: Vinny Lay (407-756-4255)

Remarks: JUST COMPLETED....WINTER PARK / LAKE SUE DISTRICT — A TRUE STANDOUT IN TODAY’S LUXURY NEW CONSTRUCTION MARKET Proudly presented by RARE Builders, a name synonymous with design-forward custom homes that continue to help set and raise the standard in Orlando and Winter Park, this newly completed residence represents a rare opportunity to secure a fully realized custom home in one of the area’s most sought-after neighborhoods. Positioned just steps from Lake Chelton and Lake Sue, and located within a highly desirable Winter Park school district, the setting delivers an exceptional lifestyle in one of Central Florida’s most dynamic and tightly held areas. While new construction inventory exists in today’s market, this home stands apart offering a fresh, cutting-edge architectural vision brought to life through exceptional planning, material selection, and execution. Prominently sited on an elevated homesite with a striking front elevation, the home offers 4,500 square feet of living space, including nearly 3,000 square feet on the ground level alone... a rare and highly functional configuration. The layout is both expansive and intentional, featuring multiple large living spaces, a private ground-floor primary suite, and a well-appointed guest suite/study/flex space. Upstairs, each bedroom is thoughtfully designed with either an en-suite bath or direct access to a full bath, delivering both comfort and privacy throughout. The defining feature of this home...and one rarely seen in the market... is the massive Renlita Floataway door system, which opens an entire wall of the home to seamlessly connect the interior Florida room with the resort-style outdoor living environment. This creates a true four-season entertaining space, transforming the way the home lives and offering a level of indoor-outdoor integration that is both dramatic and highly functional. The outdoor setting is designed as a private resort, complete with a pool, spa, fire and water features, pergola, and summer kitchen... all curated to complement the home’s architectural vision. Inside, the level of finish and design is exceptional. From breathtaking Venetian plaster walls to a dramatic two-story foyer, the home is defined by a refined and highly curated selection of materials, fixtures, and hardware. Every element has been intentionally sourced and executed, resulting in a level of craftsmanship and aesthetic cohesion that is rarely achieved and immediately recognized by discerning buyers. A well-appointed kitchen with walk-in butler’s pantry and thoughtfully designed secondary spaces further enhance both function and livability. Integrated Control4 home automation, audio, and security systems complete the offering. Located just minutes from Downtown Orlando, Winter Park, Park Avenue, Winter Park Village, AdventHealth, and Orlando Health, this home delivers a rare combination of location, design, and execution at the highest level. This is not simply new construction, it is a distinct, design-driven custom residence offering a level of detail, presence, and livability that is truly rare in the current Winter Park market.

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

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

Remarks: Opportunities like this don’t come around often, this is currently the only duplex available within walking distance of Park Avenue and just minutes from Rollins College, placing it directly in one of the most consistent, high-demand rental pockets in Winter Park. With two 3-bedroom, 2-bathroom units (6 bedrooms total), this property is ideally positioned for strong, stable income. Live in one unit and offset your mortgage, or lease both units to capitalize on long-term rental demand in a location where inventory remains extremely limited. Each unit is designed for durability and appeal, featuring open-concept layouts, stone countertops, stainless steel appliances, custom cabinetry, and wood and tile flooring throughout, finishes that attract quality tenants while keeping maintenance straightforward. Private, fenced patios extend the living space outdoors, while in-unit laundry and ample parking add everyday convenience that renters actively prioritize. The location is the true driver, just steps from the Winter Park Golf Course and a short walk to Park Avenue’s dining, shopping, and lifestyle. This level of walkability continues to support strong tenant demand and long-term appreciation, particularly in the rapidly growing West End of Winter Park. As an added benefit, the property includes a membership to the Winter Park Country Club, further enhancing its appeal for both owners and tenants. For buyers looking to secure a property that offers immediate usability, consistent rental demand, and long-term upside in one of Central Florida’s most sought-after markets, this is a rare opportunity to check all three boxes in a single acquisition.

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

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

Remarks: Under contract-accepting backup offers. Experience lakeside living in Winter Park, FL with this custom LAKEFRONT PROPERTY on the shores of Lake Killarney, a 234 acre PRIVATE LAKE. There are a limited number of lakefront properties within the City, especially on skiable lakes, so this home presents a unique opportunity. Boasting an EXPANSIVE DOCK, one that’s grander than current building standards allow (but is grandfathered in), this backyard provides an ideal place to launch your water adventures, soak up scenic sunsets, and travel by lake to Hillstone for a meal. The CUSTOM POOL is waiting to be enjoyed! It features a custom waterfall, grotto, built-in seating/table and adjacent koi pond, all with a lake view. Recent updates to the home include: shingled roof (2018), DOUBLE PANE WINDOWS (2015), and HVAC (2016). Travertine and tile floors cover the entire home, there is no carpet. The back family room has multiple French doors and offers an expansive view of the lake. Fireplaces are featured in both the office and living room. The convenience of 632 Country Club is unmatched. It is approximately .6 miles from grocery shopping like Whole Foods and Publix or the Winter Park Village - a vast outdoor mall featuring a 20-screen Regal Cinema, Ruth's Chris Steakhouse and Bar Italia, to name a few. For everyday errands like HomeGoods, or workouts at LA Fitness, there is an even closer shopping plaza. An Interstate 4 (I-4) onramp is approximately 2 miles away. Winter Park is bursting with Old Florida charm and was named #38 historic world destinations in 2008 by National Geographic Magazine. At its heart is Park Avenue, famed for its cobblestoned and tree-lined streets with over 140 boutiques, museums, a train station, and world-class dining. 632 Country Club is approximately 1.5 miles from luxurious Park Avenue and 5 miles from downtown Orlando.

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

Listing Agent: Kristin Duncan (407-274-5911)

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: Charming Winter Park Opportunity in Desirable Dubsdread Heights! NEW ROOF NEW A/c new kitchen ,bath, floor Welcome to 811 Overspin Drive, a cozy and character-filled 2-bedroom, 1-bath single-family home nestled in the heart of Winter Park. This property offers approximately 700+ square feet of living space on a generously sized lot, providing endless potential for homeowners, investors, or those looking to build their dream home in a prime location. Situated in the sought-after Dubsdread Heights neighborhood, this home is just minutes from downtown Winter Park, College Park, and Orlando’s vibrant dining, shopping, and entertainment districts. The property’s spacious lot offers room for expansion, renovation, or new construction, making it a rare opportunity in one of Central Florida’s most desirable zip codes. Whether you’re a first-time buyer, an investor seeking value-add potential, or someone looking to customize a home in a premium location, this property delivers both charm and opportunity. With strong surrounding home values and continued growth in the area, 811 Overspin Drive is an excellent chance to invest in the future of Winter Park living. Don’t miss your opportunity to own in one of Central Florida’s most sought-after communities!

Listing is courtesy of: RICK SINGH REAL ESTATE (407-383-3231)

Listing Agent: Rick Singh (407-383-3231)

Remarks: SELLER MOTIVATED!! Potential of an extra one percent for closing costs, just ask your agent!! A FULLY MODERNIZED 5-bedroom, 3-bathroom home offering Modern style, flexibility, and comfort and its own ATTACHED 2bed/1 Bath IN-LAW SUITE!!! Step inside to an open and airy layout featuring Luxury vinyl plank flooring, fresh neutral paint, and large windows that fill the home with natural light. The upgraded kitchen is a true showstopper — boasting shaker cabinets, quartz countertops, subway tile backsplash, and stainless steel appliances with stylish hardware accents. Located just a 10 minute walk to Lake Killarney and a 3 minute walk to Killarney Elementary School! What is even more fantastic is the distance to I-4 is literally just 2 minutes away for fast and convenient travel to and from downtown Orlando and just 10 minutes from Park Avenue Winter Park!! So many restaurants, parks, local shops and family activities, Especially during the holidays!! Come see this home with potential income and your own private 3/2 as well. This home includes a versatile 2-bedroom, 1-bath in-law suite with its own private entrance, perfect for extended family, guests, or rental potential. Enjoy extra living space in the spacious Florida room, ideal for entertaining, relaxing, or creating the perfect indoor-outdoor flow. With its thoughtful upgrades and multi-generational layout, this home blends functionality with timeless design — truly move-in ready and waiting for you to make it your own!

Listing is courtesy of: EXP REALTY LLC (407-846-0940)

Listing Agent: Laura Mcadams (954-268-5421)

Remarks: SELLER MOTIVATED!! Potential of an extra one percent for closing costs, just ask your agent!! Come view this NEXTGEN Home FULLY MODERNIZED 5-bedroom, 3-bathroom home offering flexibility, and comfort that Includes an Attached 2 Bed/1 Bath IN- LAW SUITE!! Step inside to an open and airy layout featuring Luxury plank flooring, fresh neutral paint, and large windows that fill the home with natural light. The upgraded kitchen is a true showstopper — boasting shaker cabinets, quartz countertops, subway tile backsplash, and stainless steel appliances with stylish hardware accents. Located just a 10 minute walk to Lake Killarney and a 3 minute walk to Killarney Elementary School! What is even more fantastic is the distance to I-4 is literally just 2 minutes away for fast and convenient travel to and from downtown Orlando and just 10 minutes from Park Avenue Winter Park!! So many restaurants, parks, local shops and family activities, Especially during the holidays!! Come see this home with potential income and your own private 3/2 as well. This home includes a versatile 2-bedroom, 1-bath in-law suite with its own private entrance, perfect for extended family, guests, or rental potential. Enjoy extra living space in the spacious Florida room, ideal for entertaining, relaxing, or creating the perfect indoor-outdoor flow. With its thoughtful upgrades and multi-generational layout, this home blends functionality with timeless design — truly move-in ready and waiting for you to make it your own!

Listing is courtesy of: EXP REALTY LLC (407-846-0940)

Listing Agent: Laura Mcadams (954-268-5421)

Remarks: Pre-Construction. To be built. Discover a rare opportunity to build a fully custom residence in the highly sought-after Killarney Shores neighborhood of Winter Park—one of the last areas where new construction at this level remains attainable below $1.3M. Exclusively curated by The Hope Group, this offering pairs premier design with a seamless build experience alongside Deep Roots Construction, MJS Designers, and Collins & Co. From concept to completion, every detail is thoughtfully orchestrated, allowing the future owner to tailor finishes, layout, and architectural style to match their vision. Ideally positioned just minutes from Park Avenue’s renowned dining, boutique shopping, and vibrant lifestyle, the property also offers convenient access to I-4, College Park, and Downtown Orlando—delivering both prestige and connectivity. The proposed residence spans approximately 2,500 square feet and is designed with intentional flow, abundant natural light, and refined modern finishes. The layout allows for elevated indoor-outdoor living, with the option to incorporate a private pool and outdoor entertaining space. Located within close proximity to major medical centers, including AdventHealth Winter Park (approximately 2.5 miles), AdventHealth Orlando (approximately 4 miles), and Orlando Health Orlando Regional Medical Center (approximately 5 miles), this location offers both lifestyle and practical convenience for medical professionals and those seeking proximity to top-tier healthcare. Opportunities like this are increasingly limited in Winter Park—secure your homesite and begin designing a one-of-a-kind residence in one of Central Florida’s most desirable zip codes.

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

Listing Agent: Vinny Lay (407-756-4255)

Remarks: Under contract-accepting backup offers. Under Construction. In the heart of Winter Parks highly coveted Tree Streets, where quiet tree-lined roads and timeless charm define the neighborhood, this stunning new construction by LUIH Homes offers a refined blend of modern architecture. The home immediately captivates with its bold contemporary façade and thoughtfully designed floor plan. Inside, elegant living spaces unfold intentionally, beginning with a sophisticated dining room accented by a custom wine bar and wine cooler. The main living room serves as a dramatic focal point of the home, featuring a stunning statement accent wall anchored by a sleek electric fireplace. At the heart of the residence, the chef's kitchen is designed to impress. Outfitted with Calacatta quartz countertops, custom cabinetry, a hidden walk-in pantry, and a full suite of Thermador appliances, the space delivers both performance and beauty. The first-floor primary suite is a true private retreat, thoughtfully positioned for comfort and tranquility. Generous in scale, it features a spa-inspired bathroom with a freestanding soaking tub, dual vanities, an expansive walk-in shower, and a large custom walk-in closet designed for both style and functionality. Also located on the first floor is an additional guest bedroom, providing flexibility for visitors, multi-generational living, or a private office. Upstairs, a spacious loft offers an additional living area perfect for relaxing or gathering, while a cleverly designed hidden homework room adds a unique and practical touch ideal for work or study. Three additional bedrooms complete the upper level, each offering generous proportions and beautifully finished spaces. Outdoors, the home transitions into a private backyard retreat designed for year-round Florida living. A covered lanai with a fully equipped summer kitchen, complete with grill and sink, sets the stage for effortless outdoor entertaining. The expansive backyard features a resort-style pool and spa, surrounded by ample space for lounging, dining, and enjoying the serene setting. The location further elevates this exceptional residence. Nestled within Winter Park's beloved Tree Streets, the home offers the rare combination of quiet neighborhood charm with incredible convenience, just a short walk to Phelps Park, The YMCA, and only minutes from the boutiques, dining, and vibrant lifestyle of Park Avenue. Don't miss this rare opportunity to own a home that truly has it all.

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

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

Remarks: Under contract-accepting backup offers. Investor Special – Fixer Upper Opportunity in Winter Park / College Park Area. Rare opportunity to acquire a true fixer-upper in the desirable Winter Park area of College Park. This 2 bedroom, 1 bathroom property needs a full renovation and is being sold as a shell—perfect for investors or builders looking for their next project. Situated on an oversized lot at the end of a quiet dead-end street, the location offers both privacy and strong potential. Conveniently located near I-4, Park Avenue, restaurants, shopping, and popular area attractions. With its prime location and generous lot size, this property presents an excellent opportunity to renovate, rebuild, or reimagine. Ideal for investors seeking value-add potential in a highly sought-after area.

Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)

Listing Agent: Mike Rance (407-629-6330)

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. Charming Mid-Century Winter Park bungalow with tremendous potential * Not ready to build a new home but would like to have that option someday? This property provides the unique opportunity of being move-in ready and not overvalued for the neighborhood * The majority of the homes on this quiet tree lined street are brand new or recently built. There is value in being one of the only remaining homesites to be rebuilt * Ready to either owner-occupy or lease ($2,095 per month lease just completed) while you take the appropriate amount of time to create your custom plans. Step inside to find beautiful, exposed hardwood floors with timeless warmth and elegance, while the updated kitchen and baths ensure the home is move-in ready for your convenience. The large, fenced backyard offers plenty of room for outdoor living, providing the perfect spot to relax or entertain * The carport features a laundry/storage area, adding even more functionality to the property * House has a durable metal roof, further enhancing its appeal and longevity. For those looking to create a custom masterpiece, the existing structure offers the option for redevelopment, allowing you to build a home that perfectly suits your vision * Owner painted the exterior, replaced the microwave and hot water heater last year * Located just off N Park Avenue and a short distance from Winter Park's main attractions, you'll enjoy proximity to Downtown Winter Park, Winter Park Farmers Market, Whole Foods, Winter Park Village, and Rollins College. Shopping, dining, and entertainment are all just moments away, making this an unbeatable location * Don’t miss the chance to make this rare find your own! Currently zoned for Lakemont Elementary, Maitland Middle and Winter Park High School *

Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)

Listing Agent: David Gallup (407-629-6330)

Remarks: Under contract-accepting backup offers. Multiple Offers! Highest and Best due by 12:00pm on Tuesday 3/10! This impeccable townhome is located in sought after Winter Park. A lovely walkway brings you the front door, where you enter into the foyer of the home. The living room boasts loads of natural light from newer large picture windows, vaulted ceilings, newer porcelain floors and a French door which leads to the deck and backyard. The dining room is just beyond the living room where the peaceful views continue. The renovated kitchen features stainless-steel appliances, soft-close drawers and cabinets with pull-out shelving, Quartz counters and a quaint eat-in area. The staircase, with a large landing area, leads you into a generous size loft with a skylight that provides ample space for an office, workout space, or library. Just beyond the loft is the large primary suite complete with dual walk-in closets with closet systems and plenty of storage space, a private balcony overlooking the front of the home and an ensuite bathroom with a dual sink vanity, jetted garden tub and separate shower. A secondary bedroom space is located on the 1st floor along with a guest bathroom that offers a granite counter vanity and separate shower. The backyard is very Zen and includes 2 decks along with green space. Other amenities and updates include: newer roof, newer water heater, newer windows and sliding door and new porcelain floors. Welcome home!

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

Listing Agent: Beth Logullo (772-633-0670)