Refine Search
Map
Sort by
$639,000
3 Beds ⋅ 2 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code
A timeless blend of historic charm and modern luxury awaits in this beautifully restored 1927 Florida bungalow, nestled in the highly sought-after and peaceful neighborhood of Orwin Manor in Winter Park. Rich in character and thoughtfully updated throughout, this exceptional residence seamlessly combines the elegance of its original architecture with the comfort and sophistication of modern living. Upon entering, you are welcomed by an inviting foyer featuring new tile flooring and refined vertical shiplap detailing, setting the tone for the home’s timeless design. Custom transitions lead into the spacious living room, where original hardwood floors, a cozy fireplace, and smart lighting create a warm and inviting atmosphere ideal for both entertaining and everyday living. The formal dining room comfortably accommodates gatherings of eight and is highlighted by a stunning Serena & Lily chandelier, creating the perfect setting for memorable dinners and celebrations. Just beyond, the fully renovated chef’s kitchen serves as the heart of the home. Updated in 2020, it features elegant Calacatta countertops, an oversized island, premium Samsung appliances, and stylish West Elm lighting. An adjacent eat-in dining space offers a more casual setting and opens directly to the beautifully paved backyard, perfect for outdoor dining and entertaining. The home’s accommodations are equally impressive, including a serene primary suite complete with dual closets and a beautifully appointed bathroom featuring sleek matte finishes. Additional living spaces include a versatile recreation room and a well-appointed guest bedroom, each designed with both comfort and functionality in mind. A private attic provides valuable additional storage space. Every detail of the home has been carefully considered to enhance both aesthetics and practicality, including smart exterior lighting, a durable vinyl privacy fence, low-maintenance landscaping tailored to Florida living, and an updated Carrier HVAC system with a smart thermostat for year-round comfort. Preserving the integrity of the home’s historic character, original woodwork, including baseboards and casings, has been thoughtfully maintained, while curated paint selections and Trex exterior staircases add lasting beauty and durability. Ideally located just minutes from Park Avenue, College Park, and major thoroughfares, this remarkable property offers an exceptional combination of tranquility, convenience, and community. More than just a home, it is a rare opportunity to own a beautifully preserved piece of Winter Park history where timeless charm and contemporary elegance exist in perfect harmony. New roof 2026***

1707 Harmon Avenue, Winter Park
$1,249,900
4 Beds ⋅ 4 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code
Pre-Construction. To be built. NEW CONSTRUCTION! Introducing an exquisite new construction home in Winter Park Grove, Winter Park's newest community! This residence is carefully curated by SGC Development, a highly respected local builder known for their dedication to quality and craftsmanship. This residence combines luxury living with the utmost convenience, located within walking distance to Publix and a variety of restaurants, and just minutes from vibrant Park Avenue. This light-filled, open-concept design showcases high-end finishes throughout. The chef’s kitchen is a true centerpiece, featuring premium Bosch appliances, a 36-inch gas range, a built-in coffee bar, and a spacious island with ample storage, creating a perfect culinary haven. The main level includes an ensuite bedroom, ideal for guests or a home office. Upstairs, discover two additional guest bedrooms, along with a luxurious primary suite that boasts a large walk-in closet and a spa-inspired bathroom. A versatile media/bonus room completes the upper level, perfect for entertainment or relaxation. Enjoy seamless outdoor living on the covered lanai with a fully equipped summer kitchen—ideal for gatherings and enjoying the Florida sunshine. Don’t miss this rare opportunity to own a thoughtfully designed home in Winter Park Grove, where modern elegance meets an unbeatable location. Schedule your private showing today! The pictures are of a model home with similar features- you can still customize to suit your needs!

Winter Park
$425,000
New England Bldg SubDv. ⋅ 32789 Zip Code
Prime office space just steps from Park Avenue in the heart of Winter Park. This 940-square-foot suite offers a rare and highly functional layout with two separate entrances — an uncommon feature in most office spaces. Enjoy the convenience and prestige of a walkable location surrounded by some of Winter Park’s most popular destinations, including New General for your morning coffee and AVA MediterrAegean for client lunches or team meetings. Ideal for professionals seeking a refined office presence in one of Central Florida’s most desirable business districts.

157 E New England Avenue Unit 302, Winter Park
$745,000
2 Beds ⋅ 3 Baths ⋅ Trotters Rep SubDv. ⋅ 32789 Zip Code
Rare investment opportunity in the heart of Winter Park/Rollins College area. This turnkey, fully renovated triplex is located within one of Winter Park’s highest-demand rental corridors, just steps from Rollins College, Park Avenue, and Lake Virginia. The property features three separate 1-bedroom, 1-bath units, each with its own private outdoor patio area, positioned on a charming brick street in one of Winter Park’s most walkable and desirable neighborhoods. The asset is being delivered with strong in-place cash flow. Current rents provide additional value-add potential, with at least one unit currently operating below market rental rates, creating an opportunity for future income growth and increased returns. The block construction property has undergone significant capital improvements, including updated electrical panels (2019), new hot water heater (2019), new windows (2017), and a new roof (2015). Two of the three units were completely renovated in 2019, offering updated interiors while maintaining the charm and character of the surrounding neighborhood. The front unit includes washer/dryer hookups, while the middle and rear units share a common exterior-access washer/dryer area. Utilities are currently included in the rent and have been factored into annual operating expenses. This is a rare opportunity to acquire a stabilized multifamily asset with strong rental demand driven by proximity to Rollins College, downtown Park Avenue, dining, shopping, and employment centers throughout Winter Park.

408 Holt Avenue, Winter Park
$380,000
2 Beds ⋅ 1 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 440 Cambridge Blvd in Winter Park, a charming 2-bedroom, 1-bath home featuring an open floorplan, an additional family room, and inviting indoor-outdoor spaces that offer both comfort and flexibility. Thoughtfully maintained and updated over time, this property combines functional living with key improvements that add long-term value and peace of mind. Inside, the open floorplan creates a bright, connected flow across the main living areas—ideal for both everyday living and entertaining. The separate family room adds valuable versatility, perfect as a media room, home office, playroom, or relaxed second living area. The bedroom layout is practical and comfortable, providing a solid foundation for personal touches and customization. Recent updates enhance both the appeal and functionality of the home, including a roof installed in 2020, HVAC system replaced in 2019, a new garage door with opener (2019), and fresh exterior paint completed in 2024. The bathroom has been refreshed with a new sink, toilet, and tub surround in 2025, offering a clean, updated feel. The outdoor spaces further elevate the property. An enclosed front porch provides a welcoming spot to enjoy a quiet morning or unwind in the evening, while the open rear patio is perfect for grilling, dining, or relaxing outdoors. The private backyard offers plenty of space to expand your vision, with strong potential to create a personalized outdoor retreat. With its solid layout, meaningful updates, and room to grow, this home presents an excellent opportunity for buyers looking to settle into a well-located property while continuing to enhance it over time. Situated in desirable Winter Park, the home benefits from a location known for its established charm, tree-lined streets, and convenient access to shopping, dining, parks, and everyday essentials, making it one of Central Florida’s most sought-after communities.

440 Cambridge Boulevard, Winter Park
$495,900
3 Beds ⋅ 3 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code
Back on market. Previous contract was canceled due to buyer circumstances. Seller is motivated and ready to move forward. Fully renovated and carefully reimagined, this 3 bedroom, 3 bath residence in the heart of Winter Park offers a compelling combination of quality, functionality, and long term value. Designed with intention and attention to detail, the property presents a refreshed, modern interior that is both visually appealing and highly practical for everyday living. The home features a completely updated kitchen with new cabinetry, brand new appliances, and a clean, contemporary design that integrates seamlessly with the main living areas. All bathrooms have been renovated, and new flooring has been installed throughout the home, creating a cohesive and polished environment. The layout has been optimized to provide comfort, flow, and usability, making the space feel open while still maintaining defined living areas. Additional improvements include updated front facing windows that enhance natural light, a new main entry door that strengthens curb appeal, and two A/C units offering efficient and flexible climate control. A detached storage structure adds valuable extra functionality, providing additional space for storage or utility use. Situated on a 0.21-acre lot, the property offers a balanced outdoor area with room for enjoyment, customization, or future enhancements. The lot configuration, which includes a portion of an adjacent lot, provides a sense of added space and flexibility not commonly found in similar properties within the area. Located in a well-established Winter Park neighborhood with consistent demand, the home benefits from convenient access to major roadways, shopping centers, dining, and key destinations. Its positioning makes it attractive for both owner occupants seeking a move-in ready home and investors looking for a well located asset with strong fundamentals. This is a property that delivers on both presentation and practicality an opportunity for buyers who recognize the value of thoughtful renovations, a strategic location and a home that is ready to be enjoyed from day one while maintaining long term upside

525 Ololu Drive, Winter Park
$1,625,000
4 Beds ⋅ 2 Baths ⋅ Virginia Heights Rep SubDv. ⋅ 32789 Zip Code
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.

446 Melrose Avenue, Winter Park
$1,040,000
4 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code
NEW PRICE!! DON'T MISS THIS OPPORTUNITY! 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 — every detail of this rennovation was completed with quality and permanence in mind. 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.

1611 Chestnut Avenue, Winter Park
$1,185,999
6 Beds ⋅ 4 Baths ⋅ Morseland Sub SubDv. ⋅ 32789 Zip Code
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.

726/720 N Pennsylvania Avenue, Winter Park
$589,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code
Tremendous value in the land. Well cared for vintage Winter Park home that has 3 BEDROOM and two bath rooms. Potential to remodel, improve and expand or simply tear down to build a new custom home. However, this home is move in ready! There is not an HOA. 1343 total square feet and 1186 heated square feet. Newer DUAL-PANE WINDOWS! New HVAC system in NOvember 2025. Home was replumbed in 2024. SEPTIC PUMP OUT, OCT 2025. No carpeting instead there is SOLID FLOORING THROUGHOUT: WOOD PARQUET, TILE, LUXURY VINYL PLANK. The kitchen has been updated with SOLID WOOD KITCHEN CABINETS + GRANITE COUNTER TOPS and newer MATCHING APPLIANCES. The home has INDOOR WASHER/DRYER and a working fireplace. The back yard is FULLY FENCED. Local top rated CITY OF WINTER PARK SCHOOLS. And CITY OF WINTER PARK UTILITIES. The land, the lot have a fantastic upside. BOTH NEXT DOOR (WEST SIDE) AND REAR (NORTH SIDE) NEIGHBORING LOTS HAVE BEEN EMPTY FOR SEVERAL YEARS. This is a great investment and the property itself offers excellent rental income. Think "down the road" value + immediate return value.

1319 Bessmor Road, Winter Park
$349,000
2 Beds ⋅ 1 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code
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!

811 Overspin Drive, Winter Park
$569,900
3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code
In the sought-after Orwin Manor neighborhood, this beautifully updated one-story residence offers a seamless blend of comfort, style and convenience. Featuring three bedrooms and two baths, the home showcases an open-concept floor plan enhanced by engineered wood flooring that extends throughout every room, creating a cohesive and inviting living environment. The kitchen is thoughtfully updated with quartz countertops, refreshed cabinetry, newer appliances and a charming breakfast nook, ideal for casual dining. The living spaces flow effortlessly to a wonderful enclosed porch, providing additional year-round enjoyment, with direct access to an open brick-paver patio complete with a firepit, all set in a fully fenced backyard ideal for entertaining or relaxing in privacy. Both baths have been tastefully updated, and a new roof installed in 2021 that adds to the home’s overall appeal and peace of mind. Ideally just minutes from vibrant shopping and dining of downtown Winter Park and College Park, with convenient access to major roadways and the AdventHealth Orlando campus, this home offers exceptional accessibility to all metro Orlando has to offer. Whether as a primary residence or an investment opportunity, this property presents an exceptional offering in a prime, established location.

1741 Westchester Avenue, Winter Park
$460,000
3 Beds ⋅ 2 Baths ⋅ Albert Lee Ridge 1st Add SubDv. ⋅ 32789 Zip Code
Preferred lender credit available. Welcome home to your peaceful retreat tucked away near the end of a quiet street with views of Lake Wilderness. Completely updated in 2017, move-in ready so you can lock and leave with peace of mind to enjoy the everyday lifestyle of Winter Park and Central Florida this amazing location offers. Full updates made in 2017 include new roof, plumbing, electrical, windows, recessed lighting, a/c unit, and more. Natural sunlight flows throughout the home reflecting off the refinished wood floors creating an inviting and cozy environment. The open kitchen features quartz countertops, glass crafted tile backsplash, custom cabinets, breakfast bar and stainless steel appliances. Feel refreshed and relaxed as you step into the primary suite with barn doors leading into the spa-inspired bathroom, complete with dual vanities and a large walk-in tiled shower. The backyard is fully fenced and the outdoor patio is screened-in and covered. Extra storage space can be used in the outdoor shed or the one car attached garage. No HOA and not in a flood zone. The property’s exceptional location offers close proximity to I-4 East and West, upscale award-winning Winter Park restaurants and boutiques, Winter Park Village, WP9 Golf Course, Park Ave, and the upcoming state-of-the-art Lifetime Fitness center which features over 85,000 SqFt and 5 acres of the best that wellness amenities have to offer. Nearby EV charging stations located within 2 miles away make sustainable living effortless. Rare opportunity to settle into or invest in a peaceful updated retreat located in the highly desirable and vibrant community of Winter Park.

950 Hanover Avenue, Winter Park
$1,049,000
5 Beds ⋅ 3 Baths ⋅ Parklando SubDv. ⋅ 32789 Zip Code
Welcome to this beautifully updated Winter Park home, perfectly positioned on a desirable corner lot and zoned for Audubon Park K-8 and Winter Park High School. With 5 bedrooms and 3 full baths, this spacious residence offers the ideal blend of functionality and style for modern living. Step inside to an open, light filled floor plan featuring luxury vinyl floors and a cozy wood burning fireplace that anchors the main living space. The renovated kitchen is thoughtfully designed with both everyday living and entertaining in mind, flowing seamlessly into the dining and living areas. A dedicated office provides the perfect work from home setup or quiet retreat, while the flexible layout offers plenty of room for guests, growing families, or multi generational living. Outside, enjoy a private backyard with a charming fire pit and rock gathering are deal for relaxing evenings or hosting friends. The oversized lot also offers ample space to add a pool and create your own backyard oasis. Additional highlights include a 2-car garage, roof replaced in 2018, home repiped in 2019, and updated AC for peace of mind. This is a rare opportunity to own a move-in ready home in one of Winter Park’s most sought after neighborhoods, walking distance to the Audubon Park Garden District with amazing dining, and shopping.

2702 Parkland Drive, Winter Park
$630,000
6 Beds ⋅ 3 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code
INVESTMENT OPPORTUNITY near Lake Killarney! This Winter Park gem offers a flexible layout perfect for multigenerational living, house-hacking, or rental income that can exceed the mortgage payment — true positive cash flow potential! Bright, spacious interiors with indep living areas for privacy & functionality. Large lot w/ mature landscaping, great for entertaining or tenant appeal. Recent upgrades incl. SOLAR PANELS (paid off at closing!), newer roof & updated A/C — big savings & peace of mind. Minutes to Park Ave, Rollins College, shopping, dining & major roadways. A rare find combining flexibility, location & strong ROI potential. Won’t last — schedule your showing today!

2600 Euston Road, Winter Park
$2,690,000
Sicilian Shores SubDv. ⋅ 32789 Zip Code
One of the last remaining opportunities to build on a truly exceptional street in the Winter Park Via’s, this .48-acre homesite offers a fantastic combination of a prime location, a large lot, and surrounded but gorgeous homes. The lot is cleared and ready to build! The current owners have thoughtfully commissioned architectural plans by renowned Winter Park architect Gary Hancock. With the Seller's impeccable taste and luxurious finishes, every detail was meticulous designed. The architectural and interior design plans could provide a jump start on your new stunning custom home. While plans are available, buyers also have the flexibility to bring their own vision to life. Ideally located just minutes from Park Avenue and surrounded by some of Winter Park’s most beautiful lakefront homes, this homesite also enjoys close proximity to the Winter Park Racquet Club, Kraft Azalea Garden, Phelps Park, and the Winter Park YMCA. Zoned for top-rated schools including Dommerich Elementary, Maitland Middle, and Winter Park High. A truly special opportunity to create a custom residence in one of Winter Park’s most coveted settings.

620 Pinetree Road, Winter Park
$1,350,000
South Lakemont Shores SubDv. ⋅ 32789 Zip Code
Lakefront home on over 1 acre in Winter Park with approximately 95 feet of frontage on Lake Spier. Positioned on a private, spring-fed lake, this property presents a rare opportunity to build a brand-new luxury residence or thoughtfully renovate the existing home into a refined lakefront retreat. The expansive lot widens toward the water, creating an exceptional setting for outdoor living, privacy, and long-term value. Located in one of Winter Park’s most established areas, just minutes from Park Avenue, top-rated schools, and everyday conveniences, this is a unique canvas for those looking to create something truly special. No HOA. No CDD.

1881 Lake Spier Drive, Winter Park
$1,350,000
3 Beds ⋅ 2 Baths ⋅ South Lakemont Shores SubDv. ⋅ 32789 Zip Code
Lakefront home on over 1 acre in Winter Park with direct frontage on Lake Spier. Positioned on a private, spring-fed lake, this property presents a rare opportunity to build a brand-new luxury residence or thoughtfully renovate the existing home into a refined lakefront retreat. The expansive lot, tranquil water views, and ownership extending into the lake create a setting defined by privacy, nature, and long-term value. Located in one of Winter Park’s most established areas, just minutes from Park Avenue, top-rated schools, and everyday conveniences, this is a unique canvas for those looking to create something truly exceptional. No HOA. No CDD.

1881 Lake Spier Drive, Winter Park
$1,250,000
4 Beds ⋅ 4 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code
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.

1870 Staunton Avenue, Winter Park
$444,900
3 Beds ⋅ 2 Baths ⋅ Fairbanks Shores 5th Add SubDv. ⋅ 32789 Zip Code
One or more photo(s) has been virtually staged. Fully rebuilt, not just renovated. This Winter Park home at 405 Lake Fair Ln has been completely transformed from top to bottom, with all major systems updated and no detail overlooked, enhanced by custom architectural wood paneling that gives the exterior a modern, high-end presence and standout curb appeal. Positioned on a quiet dead-end street with no side or rear neighbors, this 3 bedroom, 2 bathroom home offers a level of privacy that is rarely found in the area. Inside, a clean, modern layout is complemented by new LVP flooring throughout, large-format designer tile in the bathrooms, fresh knockdown texture, and integrated recessed lighting that creates a bright, cohesive feel from room to room. The kitchen is anchored by an oversized quartz island designed as a central gathering point, paired with modern shaker cabinetry and a full suite of brand new, never-used appliances. The space is built for both everyday functionality and entertaining. Both bathrooms have been fully reimagined with large-format designer tile, a matte fixture package, and frameless glass shower enclosures, delivering a clean, elevated finish throughout. Beyond the finishes, the true value is in the infrastructure. The home features a new roof, new HVAC system, updated plumbing, and electrical brought to current standards, along with two new water heaters. Additional upgrades include all new interior and exterior doors with coordinated hardware, updated lighting, fresh interior and exterior paint, new blinds, and refined finishes throughout. This is a renovation executed with long-term quality in mind. The location ties everything together. Just minutes from Park Avenue and Winter Park Village, the home offers immediate access to some of the area’s most sought-after dining, shopping, and lifestyle amenities, along with convenient access to I-4 for commuting throughout Orlando. Continued growth in the area adds long-term appeal, including a new Life Time Fitness being developed just minutes away. Education options further strengthen the location. The home is near St. Margaret Mary School, a highly regarded PK–8 private institution, as well as Bishop Moore High School, consistently ranked among the top private schools in Florida and known for strong college preparation and athletics. Edgewater High School is also nearby, offering a well-established public school option within close proximity. Nearby Full Sail University, Rollins College, and AdventHealth Winter Park further support long-term demand and stability in the area. This is a move-in ready home positioned in one of the most stable and steadily growing pockets of Winter Park, offering both lifestyle, privacy, and long-term upside. A full home warranty is included. Seller is highly MOTIVATED. BRING YOUR OFFERS

405 Lake Fair Lane, Winter Park
$499,000
3 Beds ⋅ 3 Baths ⋅ Terrazo Del Sol SubDv. ⋅ 32789 Zip Code
Virtually Staged. **Price Improvement** Welcome home to this beautifully updated two-story end-unit, ideally located just steps from Michelin-star dining, local boutiques, and the vibrant East End Market. On weekends, enjoy leisurely strolls to the area’s popular farmers markets and neighborhood events. Situated in the heart of Winter Park, this residence offers the perfect blend of lifestyle, convenience, and charm in one of Orlando’s most sought-after communities. Designed for both everyday comfort and effortless entertaining, the first floor features an open-concept kitchen and living area filled with abundant natural light, along with a convenient half bath—ideal for hosting guests. Upstairs, the spacious primary suite boasts a private ensuite bathroom, walk-in closet, and a newly refinished balcony—perfect for morning coffee or evening cocktails. Two additional bedrooms provide generous space and share access to a second balcony, creating a seamless indoor-outdoor living experience. Recent upgrades include a new dishwasher and smart refrigerator (2022), new water heater (2025), refinished front balcony (2025), new roof, and new carpet upstairs (2026). Updated light fixtures and primary bedroom flooring within the last five years add a modern touch throughout. The $400 monthly HOA fee includes landscaping and insurance, offering low-maintenance living and added peace of mind. Zoned for some of Orlando’s top-rated schools and walking distance from the new Audubon Park K-8 School, this home presents a rare opportunity to enjoy the very best of Winter Park living. Don’t miss your chance to call this exceptional property home.

1807 Hammerlin Avenue Unit G, Winter Park
$1,225,000
3 Beds ⋅ 3 Baths ⋅ Osceola Heights SubDv. ⋅ 32789 Zip Code
This new residence, thoughtfully designed by Michael Wenrich, captures the timeless elegance and refined simplicity reminiscent of the iconic coastal architecture of Alys Beach. Clean architectural lines, graceful curves, and abundant natural light combine to create a home that feels sophisticated and inviting. Inside, gorgeous chevron-patterned wood floors flow throughout the main living areas, setting a warm and elegant tone. The open-concept floor plan is designed for everyday living and effortless entertaining, with expansive windows allowing natural sunlight to pour into every space. At the heart of the home is a beautifully designed kitchen that blends classic style with modern functionality. A stunning quartz waterfall island anchors the space, complemented by custom cabinetry and a suite of high-end appliances including an ILVE induction range with six elements and Café French door refrigerator, dishwasher and microwave. Designer-grade lighting and refined finishes elevate the kitchen into a centerpiece of the home. The dining room is filled with light and character, featuring three sets of French doors that open to a charming private front and side courtyard, an ideal setting for morning coffee or intimate outdoor dining. In the living room, a dramatic wall of sliding glass doors connects the interior to the brick patio and backyard, creating a seamless indoor-outdoor lifestyle. The first-floor primary suite offers a peaceful retreat, complete with a spacious walk-in closet and a spa-inspired bath featuring a large glass-enclosed shower, separate soaking tub and dual vanities. Additional conveniences on the main level include a beautifully appointed powder bath, a dedicated laundry room and a generous storage room tucked neatly beneath the staircase. Upstairs, a versatile loft provides additional living space ideal for a media area, office or lounge. Two additional bedrooms are also on the second floor, each featuring custom built-in closets, beautiful designer lighting and abundant natural light. Built with quality and efficiency in mind, the home includes numerous upgrades such as a slate roof, Trane air-conditioning system, Rheem tankless water heater and a two-car attached garage. Ideally just minutes from the renowned shopping and dining of Park Avenue and charm of downtown Winter Park, this exceptional home also offers convenient access to major roadways, Orlando International Airport, leading hospitals, and top-rated public and private schools, bringing together style, comfort and location in one remarkable new construction opportunity.

1870 Walker Avenue, Winter Park
$918,000
4 Beds ⋅ 3 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code
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.

Lot #21 Karolina Ave, Winter Park
$574,900
3 Beds ⋅ 2 Baths ⋅ Metzingers Add SubDv. ⋅ 32789 Zip Code
Virtually Staged. Fabulous location in Winter Park! Completely remodeled from top to bottom this stunning home blends modern design with everyday comfort in a highly desirable Winter Park location. Thoughtfully updated with stylish and contemporary finishes throughout this home offers a bright and open feel that’s perfect for today’s lifestyle. The beautifully renovated interior features a modern kitchen, quartz countertops, soft-close shaker cabinets overlooking the dining room & family room. The updated bathrooms and fresh finishes throughout create a move-in ready home that feels brand new! The spacious layout flows seamlessly into the outdoor living area where you’ll find a large fenced-in backyard with a pavered patio and a cozy fireplace perfect for entertaining, relaxing or enjoying Florida evenings. Located just minutes from shopping, dining, parks, and top Winter Park amenities this property is an excellent opportunity for first-time homebuyers or investors looking for a turnkey home in a prime location. A rare opportunity to own a fully updated home with modern style and a spacious backyard in the heart of Winter Park!

1354 Indiana Avenue, Winter Park
$820,000
5 Beds ⋅ 3 Baths ⋅ Lake Bell Terrace SubDv. ⋅ 32789 Zip Code
*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.

1927 Eland Avenue, Winter Park
$1,595,000
3 Beds ⋅ 2 Baths ⋅ Tuscany Terrace SubDv. ⋅ 32789 Zip Code
Exceptional opportunity in the heart of Winter Park — a truly premier and irreplaceable homesite offering rare scale, privacy, and extraordinary future build potential. The primary value is in the land, presenting an unparalleled canvas for a custom luxury residence, with virtually no comparable vacant land available in the immediate vicinity. Set on a tranquil small lake that provides remarkable serenity and picturesque water views, this property combines peaceful natural surroundings with unbeatable walkability. Ideally positioned just steps from the Racquet Club, moments to Park Avenue’s renowned dining, boutiques, and cultural venues, and within easy reach of the Winter Park Chain of Lakes. The location also offers the distinct prestige of residing within the coveted “Vias” of Winter Park, a collection of streets long regarded as one of the city’s most established and desirable residential enclaves. The existing residence is perfectly livable and has benefited from numerous upgrades, offering flexibility for immediate occupancy while planning a future custom build. The home also presents excellent rental potential. Please note the interior is currently being utilized for storage and does not reflect its full presentation potential, providing an opportunity for cosmetic refresh or personalization. Whether envisioned as a modern architectural statement or an elegant estate home, this site delivers the location, setting, and versatility sought by discerning builders, investors, and end¦users alike — a rare chance to secure one of Winter Park’s most desirable land offerings in a highly established neighborhood.

1113 Via Del Mar, Winter Park
$1,380,000
4 Beds ⋅ 4 Baths ⋅ Sylvan Heights SubDv. ⋅ 32789 Zip Code
Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park! This 4-bedroom, 3.5-bath home showcases thoughtful contemporary architecture with 10' ceilings on both floors, and an open-concept layout that effortlessly blends style and function. With large double paned windows throughout, this home is drenched with an abundance of natural light. High-end finishes continue through the home with a level 5 finish on all walls, spray foam insulation, solid-wood doors, designer shades on every window, and custom closet systems. The showstopping chef-inspired kitchen was designed to entertain with an expansive island, seating 6, and premium finishes- including custom cabinetry, quartz countertops, soft close cabinets and drawers, a concealed Bosh dishwasher, a 48" Thermidor 6-burner gas range, and a Viking Refrigerator. The kitchen seamlessly flows into the living room and dinning space, and also offers easy access for indoor/outdoor entertaining with the telescoping sliding glass door. Outside, you will find the extended patio with plenty of room for hosting friends and family under the bistro-lighting while cooking at the summer kitchen (grill, fridge, range hood). Back inside, you will find a laundry room, half bathroom, and downstairs bedroom with an ensuite offering flexibility to the first floor. Upstairs, you are greeted with a small loft space, 2 bedrooms with a Jack-and-Jill bathroom, and an exquisite primary suite. The primary suite is a true retreat with a large balcony, his and her walk-in closets, and a spacious primary ensuite, featuring a beautiful soaking tub, designer tile, quartz countertops, and great natural light. All upstairs bedrooms are also equipped with motorized black-out shades. This residence is modern, refined, and impeccably curated, offering elevated indoor-outdoor living just minutes from Park Avenue, AdventHealth Winter Park, Rollins College, museums, dining, shopping, and all that Winter Park has to offer! Reach out to schedule your private tour today.

1751 Goodrich Avenue, Winter Park
$695,000
4 Beds ⋅ 4 Baths ⋅ Swoope Park SubDv. ⋅ 32789 Zip Code
A short stroll to Park Avenue in 5 minutes. Beautiful townhome, move in ready. Spacious and open floor plan with 4 bedrooms and 3.5 baths.

432 W Swoope Avenue, Winter Park
$459,900
Golfview SubDv. ⋅ 32789 Zip Code
Ready to build your dream home or invest in one of Winter Park’s most desirable locations? This oversized, one-of-a-kind lot is ideally situated just across from Dubsdread Golf Course and only minutes from Park Avenue, Winter Park Village, dining, shopping, and entertainment. Enjoy convenient access to major roads while still being nestled in a highly sought-after neighborhood. Located within a top-rated school district, including Princeton Elementary. A rare opportunity in Winter Park—don’t wait to make this exceptional property yours.

3601 Midiron Drive, Winter Park
$899,000
Fairbanks Park SubDv. ⋅ 32789 Zip Code
Rare corner lot with stunning views of Lake Midget, located in the heart of Winter Park within an area of modern new-construction homes. This build-ready property offers an exceptional opportunity to create a custom residence in one of the city’s most desirable neighborhoods. Just minutes from Park Avenue and Winter Park Village, with easy access to premier dining, shopping, and entertainment. Lots like this are seldom available. Whether you’re envisioning a custom residence or an investment in one of Central Florida’s most desirable neighborhoods, this is a truly rare opportunity in the heart of Winter Park.

731 Midget Drive, Winter Park