Refine Search
Sort by
870 N Phelps Avenue, Winter Park
$850,000
Osceola Or Lakeview Deed SubDv. ⋅ 32789 Zip Code
Bring your vision to life in Winter Park. Situated on N Phelps Avenue, this approximately .24-acre property offers a rare opportunity to build new in an area surrounded by custom homes, luxury residences, and ongoing redevelopment. Offered for its land value, this property is well suited for builders, investors, developers, or anyone ready to create a home designed around their own style and needs. The 75-foot frontage with 140-foot depth provides flexibility for a variety of architectural designs and potential for outdoor living, a pool, and backyard space. With new construction continuing to reshape the surrounding area, 870 N Phelps presents an exciting opportunity to secure a sizable homesite and build from the ground up.

870 N Phelps Avenue, Winter Park

266 N Ranger Boulevard, Winter Park
$724,900
4 Beds ⋅ 3 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
FULLY RENOVATED Winter Park Pines Home with Mother-in-Law Suite, NO HOA & Prime Location! Welcome to this beautifully transformed Winter Park Pines residence, where modern design, thoughtful upgrades, and flexible living spaces come together in one exceptional home. Ideally located adjacent to the Cady Way Trail, with NO HOA, this property offers the lifestyle and convenience of Winter Park with the flexibility today’s buyers are looking for. Upon entering, you’re greeted by a dramatic custom charcoal accent wall with geometric detailing, creating a distinctive architectural focal point and setting the tone for the home’s contemporary design. Inside, the open and inviting floor plan features Luxury Vinyl Plank flooring throughout, recessed LED lighting, all-new interior doors, and a stylish LED fireplace that adds warmth and ambiance to the main living area. The completely renovated kitchen is designed for both everyday living and entertaining, featuring new Shaker-style cabinetry, Quartz countertops, a large center island, luxury backsplash, stainless-steel appliances, and a dedicated coffee bar with wine refrigerator. The open layout provides an ideal gathering space for family and guests. The home also features a private Mother-in-Law Suite with its own entry and outside walkway, offering exceptional flexibility for extended family, overnight guests, a home office, or a private living area. The suite includes its own beautifully renovated bathroom with a rain shower, enclosed by a ceiling-to-threshold glass pane, and an illuminated LED mirror. The primary suite bathroom has been upgraded to a luxurious, contemporary retreat, featuring a smart toilet, dual vanities, illuminated LED mirror, and an executive-style stand-up rain shower. The shower incorporates a thoughtfully designed inclined floor that directs water into a rectangular drain, along with a striking floor-to-ceiling glass enclosure, creating a clean, open, and refined feel without the need for a traditional shower curtain. Additional major improvements include a new Carrier HVAC system, tankless water heater, updated double-pane windows, complete re-plumbing, re-wiring with an updated electrical panel, and a new roof installed 7/17/2023. Step outside and enjoy the home’s inviting outdoor spaces, including a covered front porch with dusk lighting, screened rear porch, spacious backyard, and oversized driveway. A series of cement slab walkways, separated by polished, large river stones, leads from the garage to the front door, with matching paths continuing along the rear of the home. Solar security lighting and decorative LED lighting add both functionality and evening ambiance. Ideally situated in Winter Park Pines and directly adjacent to the Cady Way Trail, the home offers convenient access to major roadways, hospitals, golf courses, colleges, shopping, dining, and highly regarded private schools—all within a short drive. With an extensive renovation, three beautifully updated bathrooms, a private Mother-in-Law Suite, modern kitchen, tankless water heater, new roof, updated electrical and plumbing, NO HOA, and an outstanding Winter Park location, this home offers a rare combination of style, functionality, and convenience. Come experience the renovation, thoughtful details, and flexible floor plan in person. Schedule your private showing today!

266 N Ranger Boulevard, Winter Park

1760 Oakhurst Avenue, Winter Park
$2,500,000
5 Beds ⋅ 5 Baths ⋅ Jenkins Second Add SubDv. ⋅ 32789 Zip Code
Experience the pinnacle of modern luxury in this architectural masterpiece, perfectly situated in the highly coveted City of Winter Park. Boasting five bedrooms and four-and-a-half bathrooms, this custom residence seamlessly blends striking contemporary lines with exceptional everyday functionality. The heart of the home is a culinary dream chef's kitchen, anchored by an oversized center island and premium quartz countertops. It comes fully equipped with custom 42-inch wood cabinetry, a dedicated walk-in pantry, and high-end appliances, including a 48-inch refrigerator, a 36-inch induction cooktop with a vented hood, a built-in microwave, a dishwasher, and double convection ovens. Entertain effortlessly in the adjacent formal dining room or mix drinks at the wet bar, which features a built-in wine chiller to keep your collection perfectly preserved. Designed for ultimate privacy, the first-floor primary suite serves as a peaceful sanctuary, complete with a spa-inspired bathroom featuring a spacious walk-in shower, a standalone soaking tub, and a thoughtfully organized his-and-hers walk-in closet with abundant storage. A generous guest retreat with a private full bath is also conveniently located on the main level. Ascend to the second floor to find soaring 11-foot ceilings and three additional well-appointed bedrooms, each designed with privacy and direct full-bath access in mind. Step through oversized sliding glass doors to transition into your private outdoor oasis, effortlessly expanding your living space into the open air. This smart-home-ready masterpiece comes equipped for integrated lighting, audio, and security, alongside pre-installed exterior accent lighting, security cameras, and a full-property irrigation system. Perfectly positioned for an elevated Florida lifestyle, this home is less than five minutes from the premier Interlachen Country Club, walking distance to Phelps Park, and just ten minutes from the world-class boutique shopping and fine dining along Park Avenue.

1760 Oakhurst Avenue, Winter Park

7498 Aloma Pines Court, Winter Park
$355,000
3 Beds ⋅ 3 Baths ⋅ Aloma Trails SubDv. ⋅ 32792 Zip Code
Welcome to beautiful Winter Park. This Townhome in Gated Aloma Trails has been meticulosly maintained. With an open and spacious floor plan is great for family activities and entertaining. NEW HV/AC AND NEW WATER HEATER. kitchen features all stainless steel appliances, large island great for prep with seating for "4" or more on the oposite side. The large slider leads out to your 5' X 11" private lani, allows natural light to fill the entire space. There is a first floor powder room for convenience for you and your guest. Second floor laundry closet for your convenience. Your oversize primary bedroom features a spacious walk-in closet and ensuite with large vanity and double sinks. There are "2" additional guest bedrooms. The home has a one car garage with an extended pad for a second car. the NEW water heater is located in the garage. The A/C is also NEW. Aloma Trails is convenient to shopping directly accross the street from the complex. minutes from Aloma (426), 417, UCF, Full Sail, Rollins, a Park Ave., Airport and Beaches. SELLER IS MOTIVATED

7498 Aloma Pines Court, Winter Park

7786 Fox Knoll Place, Winter Park
$398,000
3 Beds ⋅ 2 Baths ⋅ Bridgewater SubDv. ⋅ 32792 Zip Code
PHENOMENAL DEAL, newer updates INCLUDE: beautifully renovated 4-bedroom, 2-bathroom, two car garage home that perfectly blends modern design with everyday comfort. From the moment you step inside, you’ll appreciate the open-concept floor plan, thoughtfully designed to create a bright, spacious atmosphere that’s perfect for both entertaining and daily living. This move-in-ready home features custom finishes throughout, including stylish fixtures, updated flooring, and a beautifully remodeled kitchen and living space. The expansive primary suite offers a private retreat with a generous bedroom and a stunning ensuite bathroom designed with comfort and luxury in mind. Additional updates include newer roof, AC, water heater, Updated kitchen and bathrooms, The Kitchen is Large with all major appliances: Fridge, Stove, and Dishwasher. You don't want to miss this opportunity to make this house your home!

7786 Fox Knoll Place, Winter Park

450 N Lakemont Ave, Winter Park
$200,000
32792 Zip Code
This well established Massage Therapy School has been serving Central Florida for over 30 years, of offering a strong reputation and a fully operational educational environment. With consistent enrollment and a trusted name in the community, it presents a rare opportunity for a buyer seeking a turnkey business in the wellness and education sector. The school currently operates three active classes, both day and evening, with the capacity to add a fourth class to increase revenue. The facility is fully equipped and thoughtfully designed, featuring two conference style classrooms, multiple massage therapy rooms that can be rented for additional income, two bathrooms, a fully equipped administrative office, a cafeteria for students and instructors, dedicated storage rooms, and a library store offering class books and massage therapy products for sale. Its location in a high visibility plaza provides excellent exposure and accessibility. This is an ideal opportunity for an investor or licensed massage therapist looking to expand, rebrand, or scale through modern advertising and marketing strategies. With its solid foundation, long-standing reputation, income producing layout, and retail component, the school is ready for a new owner to elevate it and unlock its full growth potential.

450 N Lakemont Ave, Winter Park

1660 Orange Avenue, Winter Park
$449,900
3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code
PRICE REDUCED!!! Don’t miss this wonderful opportunity to own a 3-bedroom, 2-bath home in the desirable Orwin Manor area of Winter Park, conveniently located just minutes from AdventHealth, Park Avenue, Downtown Orlando, and I-4. This spacious two-story home features a flexible layout with a two-car garage, remodeled bathrooms, and plenty of living space. The first floor offers a large bedroom, a beautifully remodeled full bathroom, a laundry area and access to the enclosed/screened patio and backyard. Upstairs, you’ll find an open kitchen with stainless steel appliances, a dining area, and a spacious living room. The second floor also features two bedrooms, including the primary bedroom with a remodeled bathroom. Wood flooring and carpet are featured throughout the home. Additional improvements include a roof approximately 5 years old, completely refreshed landscaping and outside power washed. Sliding doors off the kitchen and dining area lead to a new outdoor deck, creating an ideal space for outdoor dining, entertaining, and enjoying the Florida lifestyle. The convenient location provides easy access to major roads, shopping, dining, entertainment, and all that Winter Park and Downtown Orlando have to offer. This home offers a great combination of location, space, and recent updates. Schedule your showing today!

1660 Orange Avenue, Winter Park

2818 Ambergate Road, Winter Park
$429,900
3 Beds ⋅ 2 Baths ⋅ Winter Park Estates Sec 5 SubDv. ⋅ 32792 Zip Code
Welcome home to this charming Winter Park residence located in the desirable 32792 zip code. Nestled on a quiet street at 2818 Ambergate Road, this inviting property offers the perfect blend of comfort, style, and everyday convenience. Step inside to discover a bright, open floor plan featuring original Terrazzo, generous living spaces, natural light, and a warm atmosphere ideal for both relaxing and entertaining. Newer roof 2023. The private backyard provides a wonderful outdoor oasis for weekend gatherings or peaceful morning coffee. Situated just minutes from top-rated schools, local parks, bustling shopping centers, and vibrant downtown Winter Park, this move-in-ready home puts the best of Central Florida right at your doorstep. Don't miss this exceptional opportunity - Schedule your private showing today!

2818 Ambergate Road, Winter Park

100 S Virginia Avenue Unit 201, Winter Park
$1,450,000
3 Beds ⋅ 3 Baths ⋅ Winter Park Residential SubDv. ⋅ 32789 Zip Code
Discover luxury and effortless living in this exquisite single-story, second-floor residence at the highly sought-after Douglas Grand in the heart of Winter Park. This spacious three-bedroom, three-bath condominium beautifully balances sophisticated entertaining with everyday comfort, offering an inviting open floor plan filled with natural light, elegant crown molding, and stunning French Oak hardwood flooring. The gourmet kitchen is a true chef’s retreat, featuring a generous island with stunning quartz countertops, custom wood cabinetry, top-of-the-line Sub-Zero, Wolf, and Bosch appliances, and a spacious walk-in pantry. The serene primary suite offers a luxurious escape with an indulgent soaking tub, dual vanities with granite countertops, and two expansive walk-in closets. The second bedroom features a private ensuite bath and generous walk-in closet, while the third bedroom offers excellent flexibility and convenient access to a full bath. Thoughtful updates and amenities include a spacious utility room with a LG washer and dryer, updated light fixtures throughout, Roman shade window treatments, color-changing recessed lighting, Google smart carbon monoxide/fire detectors, Nest thermostats, and a 81-gallon water heater installed in December 2023. One of the residence’s most desirable features is the private entry directly from the secure, gated garage, with two reserved parking spaces conveniently located just outside your front door. Ideally situated in the heart of Winter Park, Douglas Grand places you moments from Park Avenue, the Winter Park Farmers’ Market, Rollins College, Hannibal Square, the Winter Park 9-hole golf course, Winter Park Tennis Center, and Winter Park Village. Experience the best of Winter Park with the comfort, privacy, and convenience of elevated condominium living at Douglas Grand.

100 S Virginia Avenue Unit 201, Winter Park

7348 Grand Avenue, Winter Park
$255,000
3 Beds ⋅ 2 Baths ⋅ Oakcrest-516 SubDv. ⋅ 32792 Zip Code
Welcome! This three-bedroom, two-bathroom home in Winter Park presents a genuine opportunity for buyers ready to reimagine this one-story residence. The open floor plan creates a flexible living space, and the thoughtful layout gives you a solid foundation to work with. Inside, the cathedral ceiling in the main living area draws the eye upward and enhances the sense of openness throughout the home. The covered rear lanai extends your entertaining and living space outdoors, perfect for relaxation or gatherings. The location delivers great convenience, with proximity to Publix-anchored shopping and Walmart for everyday needs, Red Bug Lake for outdoor recreation activities, grade schools, and the Winter Park Village for shopping and dining. Schools are nearby, making this neighborhood accessible for residents. The central location means you're less than 30 minutes from Orlando International Airport, Universal, Downtown Orlando, and UCF, offering both lifestyle flexibility and strong rental demand drivers for those considering income-producing use. Convenient access to major roadways makes commuting and daily needs straightforward. Schedule your private showing today and bring your vision for what this home can become.

7348 Grand Avenue, Winter Park

120 Broadview Avenue, Winter Park
$1,250,000
3 Beds ⋅ 2 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code
SPECTACULAR OPPORTUNITY ON SCENIC LAKE KILLARNEY Discover a rare opportunity to live on scenic Lake Killarney—a 236-acre, spring-fed private lake with no public access. Nestled along a charming, tree-canopied, lakefront dead end brick street, this 1947 bungalow offers 1,747 square feet of pure potential, featuring 3 bedrooms, 2 baths, a 2-car garage, and a lovely corner lot. Renovate the existing home or create your dream residence in this tranquil setting, where breathtaking sunsets and peaceful lake views await. Enjoy the convenience of being within walking distance of restaurants and shopping, while having easy access to Interstate 4, Rollins College, and all that Winter Park’s renowned Park Avenue has to offer. THREE UNIQUE OPPORTUNITIES: Option 1 — $1,250,000 115' x 65' property + 65' lakefront. Option 2 — $1,450,000 155' x 65' property + 65' lakefront. Option 3 — $2,250,000 155' x 95' property + 95' lakefront. A truly rare find in a quaint and desirable neighborhood, offering the flexibility to renovate, expand, or build the home you’ve always envisioned. Come experience the tranquility, privacy, and beauty of Lake Killarney. WELCOME HOME!

120 Broadview Avenue, Winter Park

120 Broadview Avenue, Winter Park
$2,400,000
Killarney Estates SubDv. ⋅ 32789 Zip Code
SPECTACULAR OPPORTUNITY ON SCENIC LAKE KILLARNEY! .39 acres: 17,100 sq ft (approx 24,000 sq ft: .55 acres including lakefront & street easement on both corner streets: 95 ft lakefront not included in FAR) Discover a rare opportunity to live on scenic Lake Killarney—a 236-acre, spring-fed private lake with no public access. Nestled along a charming, tree-canopied, lakefront dead-end brick street, this 1947 bungalow offers 1,747 square feet of pure potential, featuring 3 bedrooms, 2 baths, a 2-car garage, and a lovely corner lot. Renovate the existing home or create your dream residence in this tranquil setting, where breathtaking sunsets and peaceful lake views await. Enjoy the convenience of being within walking distance of restaurants and shopping, while having easy access to Interstate 4, Rollins College, and all that Winter Park’s renowned Park Avenue has to offer. THREE Optional OPPORTUNITIES: Option 1 — $1,450,000 155' x 65' property + 65' lakefront. Option 2 — $1,250,000 115' x 65' property + 65' lakefront. Option 3 — $2,250,000 155' x 95' property + 95' lakefront. A truly rare find in a quaint and desirable neighborhood, offering the flexibility to renovate, expand, or build the home you’ve always envisioned. Come experience the tranquility, privacy, and beauty of Lake Killarney. WELCOME HOME!

120 Broadview Avenue, Winter Park

4572 N Palmetto Avenue Unit A, Winter Park
$3,200,000
4572 Palmetto Condo SubDv. ⋅ 32792 Zip Code
Prime commercial/industrial opportunity in Winter Park! This warehouse building offers excellent visibility and exposure along high-traffic Palmetto Ave., also known as Goldenrod Road, with approximately 275+ feet of road frontage. The property is zoned Industrial and features approximately 11,500 square feet of total space, including warehouse, showroom, office, and retail/wholesale areas. Warehouse: Approximately 8,000 sq. ft. featuring:3 overhead doors, High loading dock, Exhaust fans & Mezzanine. Showroom / Wholesale & Retail: Approximately 8,843 sq. ft. of air-conditioned space, featuring:2 private offices, 3 full bathrooms, Full kitchen. This property offers a versatile layout and excellent visibility for a variety of industrial, wholesale, retail, and commercial uses. SELLING BUILDING ONLY. Business, inventory, furniture, automobiles, equipment, and other personal property do not convey with the sale.

4572 N Palmetto Avenue Unit A, Winter Park

4260 Bear Gully Road, Winter Park
$585,000
4 Beds ⋅ 4 Baths ⋅ Bear Gully Forest SubDv. ⋅ 32792 Zip Code
RENOVATED 4 BED / 3.5 BATH ON AN OVERSIZED 0.57-ACRE LOT | GOURMET KITCHEN | SCREENED LANAI | FENCED YARD | ROOF 2018 | FLOOD ZONE X | LOW HOA. Welcome to 4260 Bear Gully Road, a move-in-ready two-story home on nearly 25,000 sq ft of land, with space for a pool, garden or play area (buyer to verify). The gourmet kitchen was fully remodeled two years ago with upscale cabinetry and modern appliances, and luxury vinyl flooring gives the home a clean, low-maintenance look. The primary suite is on the first floor with a walk-in closet, and four bedrooms and three and a half baths give everyone room for family, guests or a home office. Ceiling fans, a two-car garage with opener, and concrete block and stucco construction add comfort and peace of mind. Relax on the screened lanai overlooking the large fenced backyard. Near Publix-anchored shopping and dining on Aloma Avenue, AdventHealth Winter Park, the Cross Seminole Trail and SR 417, with Winter Park Village and Park Avenue a short drive away. Seminole County schools: Eastbrook Elementary, Tuskawilla Middle and Lake Howell High (buyer to verify). Schedule your showing today!

4260 Bear Gully Road, Winter Park

1306 S Pennsylvania Avenue Unit 5, Winter Park
$349,000
2 Beds ⋅ 1 Baths ⋅ Virginia Heights Condo SubDv. ⋅ 32789 Zip Code
NEW PRICE! Charming Winter Park 2BR/1BA Condo with Lake Virginia Access! Beautifully renovated and ideally located near Park Avenue, Rollins College, Hannibal Square, and Mead Botanical Garden, this spacious second-floor condo combines architectural character with an unbeatable Winter Park lifestyle. Soaring cathedral/vaulted ceilings, hardwood floors, plantation shutters, custom built-ins, and French doors create a warm, cosmopolitan feel. The renovated kitchen features granite countertops, stainless-steel appliances, an induction range, bay window, and cozy dining nook. Spacious primary bedroom offers vaulted ceilings and French doors opening to a private screened outdoor space. Flexible second bedroom is ideal as a home office or guest room. Enjoy a private community dock with Lake Virginia access for kayaking, paddleboarding, or relaxing by the water. Expansive private deck overlooks picturesque Mead Gardens. Includes storage and garage space plus convenient in-unit laundry. Walk or bike to Park Avenue shops, restaurants, Rollins College, and everything that makes Winter Park so desirable!

1306 S Pennsylvania Avenue Unit 5, Winter Park

1517 Harmon Avenue, Winter Park
$1,049,000
4 Beds ⋅ 4 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code
Some houses impress you. This one welcomes you. A fully remodeled Victorian in Winter Park, reimagined from top to bottom and minutes from Park Avenue shopping and dining. The kitchen is the heart of it all, wrapped in Calacatta Viola quartz with a full height backsplash, cabinet lighting that glows after dark, and all new Bosch appliances. The open first floor flows naturally from kitchen to dining to living, anchored by a fireplace made for slow evenings, and new engineered hardwood flooring runs throughout the entire house. All 3.5 baths are completely redone with marble floors, designer tile, and brass fixtures, including a first floor half bath with wall paneling and a one of a kind vanity that stops people mid tour. This remodel went beyond the pretty parts. A brand new roof covers the entire house and detached garage, all outlets and switches were replaced throughout, and the plumbing was redone for the kitchen and all bathrooms. The water heater is new, and the laundry room has a new stacked washer and dryer too. You move in and live, nothing to fix, nothing to update. Upstairs and down, every bedroom is spacious and has custom built in closet systems, and the stairway shows off custom oak newels and handrails with black metal balusters. Outside, the charm continues with a herringbone brick-tile front porch, balconies and back porch made for morning coffee, fresh paint inside and out, new landscaping, a new paver driveway, and a detached two car garage with a newly stained concrete floor. This is not a quick flip. Every finish was chosen with intention, and every detail was completed with care. 4 bedrooms, 3.5 baths, 2,135 sq ft of living space on a 7,151 sq ft lot, in one of Winter Park's most loved pockets. This is a home you will feel from the first moment you walk in.

1517 Harmon Avenue, Winter Park

2463 Grand Teton Circle Unit 2463, Winter Park
$249,000
3 Beds ⋅ 3 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code
Virtually Staged. Don't miss this incredible opportunity in one of Winter Park's most desirable locations! This spacious 2-story condo offers over 1,700 square feet of living space, featuring an open floor plan that's perfect for everyday living and entertaining. A dedicated office space adds flexibility for remote work or a home study a rare find at this price point. While the home could use some updating, the bones and layout make this a fantastic canvas to add your personal touch and build instant equity. Currently occupied by a great tenant, this property is a perfect turnkey opportunity for investors looking to add a cash-flowing asset to their portfolio, or for buyers ready to move in once the lease ends on June 2027. With its unbeatable location near Winter Parks shopping, dining, and entertainment, this is the kind of opportunity that won't last long at $249,000. Don't miss this and make your appointment today!

2463 Grand Teton Circle Unit 2463, Winter Park

1803 Barker Drive, Winter Park
$2,190,000
4 Beds ⋅ 3 Baths ⋅ South Lakemont Shores SubDv. ⋅ 32789 Zip Code
A rare opportunity awaits to own a slice of paradise on Lake Spier in beautiful Winter Park! Set on over two acres and surrounded by mature landscaping, this stunning property offers a secluded setting that feels worlds away, while world-class dining and shopping, trails and parks, and the vibrant Village Center of renowned Baldwin Park are just moments from your door. Inside, you'll find luxury finishes and appliances, expansive hurricane-impact windows, all-new HVAC and a whole-house water filtration system, along with double master suites with vaulted ceilings and distinctive architectural details throughout. Step outside, where 158 feet of lakeshore and your private dock invite you to enjoy the water at its best, from boating and waterskiing to beautiful sunrises and sunsets on the water. With approximately 3,400 square feet, four bedrooms, three baths, a detached garage/workshop and no HOA, this is a truly unique offering in one of Winter Park's most desirable locations.

1803 Barker Drive, Winter Park

5080 Seminole Avenue, Winter Park
$299,900
3 Beds ⋅ 2 Baths ⋅ Suburban Homes SubDv. ⋅ 32792 Zip Code
FULLY FURNISHED and ready for its next owner! This 3-bedroom, 2-bath Winter Park home offers an excellent combination of recent improvements, location, and flexibility. Major updates include a NEW ROOF (2021), FULL HOUSE REPIPE (2025), and NEW FLOORING (2025), giving buyers peace of mind on several important big-ticket items. Situated on an OVERSIZED 0.24-ACRE LOT with NO HOA, the property offers a spacious yard with plenty of room to enjoy the outdoors. Inside, the home features a comfortable and functional layout with an eat-in kitchen, indoor laundry, and inviting living spaces. Even better, the home is being sold FULLY FURNISHED, making it an easy option for a primary residence, second home, or investment property. The location is hard to beat, with convenient access to Full Sail University, Rollins College, UCF, Park Avenue, Baldwin Park, shopping, dining, and major roadways connecting you throughout Central Florida. With NO HOA and short-term rental potential, this property provides flexibility that can be difficult to find in Winter Park. Whether you're looking for a place to call home or an investment opportunity, 5080 Seminole Ave is ready for its next chapter!

5080 Seminole Avenue, Winter Park

3334 Young Street, Winter Park
$469,900
3 Beds ⋅ 2 Baths ⋅ Winter Park Forest SubDv. ⋅ 32792 Zip Code
This beautifully transformed 3-bedroom, 2-bathroom block home offering modern updates, quality finishes, and true move-in-ready appeal in Winter Park. This standout property features a 2-car garage, spacious 3-bedroom layout, and an extensive renovation completed with today’s buyer in mind. Step inside to a bright, redesigned open-concept kitchen with a fresh, modern feel, brand new kitchen appliances, range with oven, microwave, complemented by brand-new flooring throughout and two completely renovated bathrooms. Major improvements include a new 2026 A/C system, new windows, fresh interior and exterior paint, along with an extensive list of additional upgrades throughout the home. Thoughtfully renovated, beautifully presented, and ready for its next owner—this is a home you’ll want to see in person to fully appreciate.

3334 Young Street, Winter Park

167 Jergo Road, Winter Park
$530,000
4 Beds ⋅ 4 Baths ⋅ Monroe SubDv. ⋅ 32792 Zip Code
Duplex on Two Separate Lots with No HOA! Excellent opportunity for an investor or owner-occupant! This 2-bedroom, 2-bathroom duplex offers flexibility with each unit situated on its own separate lot and no HOA. One unit is currently tenant occupied, providing immediate rental income, while the second unit is vacant and ready for a new tenant or owner-occupant. The vacant unit features an updated kitchen, giving it a fresh, move-in-ready feel. The property has also been freshly painted on the exterior, enhancing its curb appeal and making it ready for its next owner. With two separate lots, an existing income-producing unit, a vacant updated unit, and no HOA, this property offers multiple possibilities for a buyer looking to add to a rental portfolio, live in one side while renting the other, or explore the advantages of the property's existing separate lot configuration. Highlights include: 2 bedrooms and 2 bathrooms in each unit, two separate lots, one occupied income-producing unit, one vacant unit with an updated kitchen, freshly painted exterior, and no HOA. A versatile Central Florida investment opportunity with immediate income and plenty of potential!

167 Jergo Road, Winter Park

504 W Swoope Avenue, Winter Park
$1,300,000
3 Beds ⋅ 3 Baths ⋅ Vilasa Twnhms SubDv. ⋅ 32789 Zip Code
Enjoy luxury living and premium sought-after location at Vilasa Homes, the newest construction in Winter Park, FL 32789. Walk to Park Avenue lifestyle, arts and culture- a mini-version of Manhattan’s Central Park, brick streets, historic neighborhoods, area’s hottest restaurants, shopping and the prestigious Rollins College. The finishes for this 2-estory townhome personally selected by one of the nation’s top interior designers. Carefully selected design team of Nasrallah Architectural Group, Ted Maines Interiors and Jordan Builders. Alys Beach inspired incorporating wood accents, architectural stairway, wrought iron and two-story ALL block construction all steps away from downtown Winter Park. Energy-saving features such as Pella double pane windows and extra insulation. Home is prewired for surround sound, cameras, alarm system, etc. Beautifully appointed-Revwood/LVP flooring throughout from Daltile/Mohawk, recessed lights, level 4 wall finishes, 13-foot ceilings on the main floor, and 10-foot ceilings upstairs. This unit has been thoughtfully upgraded with a top modern package worth $40k. Chef’s gourmet kitchen is complete with high-end 18” flat panel cabinetry, 2.5” mitered Quartz countertops, double waterfall Quartz island, Thermador appliances, and beautiful Quartz backsplash. 6 burner Thermador SS gas cooktop, built-in butlers bar in dining room, staircase lighting are all additional upgrades. Spacious primary retreat on second floor with loft area perfect for office, Peloton or game room all wired with internet and electrical. Primary bedroom includes two separate his and hers closets with custom shelving and organizers. Generous closet and storage spaces. Relax in your garden tub and oversized walk-in shower, Quartz countertops, designer tile, Koehler fixtures/bathroom accessories and custom lighting treatments. Two more stately suites that can be used for exercise, office or bedrooms. Automated, remote window coverings. 2-car garages featuring insulated steel garage doors and additional storage. The Swoope townhomes each have an enlarged backyard measuring approx. 40ft x 20ft, including 8ft x 8ft covered patio slab which extends from the sliding doors. Each unit includes privacy fencing and landscaping. Owners maintain own backyard. Convenient and minutes from Hillstones, Whole Foods, Trader Joe's, Park Avenue restaurants and shopping! Top rated-9 hole Winter Park Golf Course, Casa Feliz, Morse Museum, water sports, Rollins, and churches are all a short stroll away.

504 W Swoope Avenue, Winter Park

7560 Aloma Pines Court, Winter Park
$355,000
3 Beds ⋅ 3 Baths ⋅ Aloma Trails SubDv. ⋅ 32792 Zip Code
Welcome to 7560 Aloma Pines Ct, a move-in-ready 3-bedroom, 2.5-bathroom townhome offering 1,866 square feet of comfortable living space in a gated Winter Park community. Built in 2016, this thoughtfully designed home offers a practical layout with plenty of space to spread out, including a primary suite conveniently located on the second floor. The kitchen features stone countertops and opens naturally to the main living areas, creating an easy flow for everyday living and entertaining. Tile and carpet flooring run throughout the home, while the attached one-car garage adds everyday convenience and storage. Step outside and enjoy the ease of low-maintenance townhome living without giving up the comfort of having your own private residence. The gated community provides an added sense of privacy, while the home's location puts you close to the shopping, dining, schools, and everyday conveniences that make the Winter Park area so desirable. Whether you're looking for your first home, a place to simplify your lifestyle, or an investment property in a convenient Central Florida location, 7560 Aloma Pines Ct offers a comfortable combination of space, functionality, and location. Move in, settle in, and enjoy everything Winter Park and the surrounding area have to offer.

7560 Aloma Pines Court, Winter Park

913 Moss Lane, Winter Park
$950,000
3 Beds ⋅ 2 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code
913 Moss Lane is in the Vias of Winter Park, on a tree-lined street in Maitland Shores. Neighborhood access to the Winter Park chain of lakes is a block away. Winter Park Racquet Club is a short walk. Park Avenue is a short drive. The home is zoned for Dommerich Elementary, Maitland Middle, and Winter Park High. The house is a 1953 split-level with 3 bedrooms, 2 baths, about 1,887 square feet, and a two-car garage. The main floor has the living room, dining area, kitchen, and Florida room. The bedrooms are upstairs. The 2023 renovation added new flooring, interior and exterior paint, a kitchen with white cabinetry, stone counters, and stainless appliances, and an updated bath with a walk-in glass shower. The backyard is fenced and has a patio. There is no homeowners association. This is a renovated three-bedroom in the Vias. See it for the street, the schools, and the lakes.

913 Moss Lane, Winter Park

786 W Canton Avenue, Winter Park
$450,000
Capens Add SubDv. ⋅ 32789 Zip Code
HIGH & DRY | PRIME WINTER PARK LOCATION | BUILD YOUR DREAM HOME Rarely does an opportunity like this become available in the heart of Winter Park! This high-and-dry homesite is ideally situated in a highly desirable area surrounded by beautiful new construction homes, including a newer community of impressive million-dollar residences directly across the street. Located in coveted Old Winter Park/32789, this approximately 96' x 49' lot offers a rare opportunity to create your very own custom home in one of Central Florida’s most sought-after locations. This location offers the finest in Orange County Schools, award winning Winter Park High. Originally home to a residence years ago, this property offers an exciting opportunity to bring your favorite builder and create a home designed specifically for your lifestyle. Imagine building your own one-of-a-kind masterpiece in a neighborhood where new construction and redevelopment are transforming the area while maintaining the character and charm that makes Winter Park so special. LOCATION truly sets this property apart! Bike to Park Avenue or stroll to Winter Park Village, where premier dining, shopping, entertainment, and everyday conveniences are just minutes from your future front door. Enjoy easy access to Hannibal Square, the Park Avenue corridor, U.S. 17-92, I-4, grocery stores, specialty shops, the Winter Park Community Center and Park, Rollins College, and AdventHealth. With new construction continuing to surround the area, this is your chance to secure a piece of Winter Park before available land becomes even harder to find. Zoned R-1A and located within the desirable Winter Park area, this property offers exceptional potential for a custom residence or investment. NO HOA. Bring your imagination, creativity, and builder! If you’ve been searching for that special Winter Park homesite where location, lifestyle, and future value come together, your search may be over. This is the Winter Park sweet spot you’ve been waiting for! View Virtual tour for a live view of the street.

786 W Canton Avenue, Winter Park

540 N Pennsylvania Avenue, Winter Park
$3,950,000
4 Beds ⋅ 2 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code
Rare Winter Park redevelopment opportunity on a NEARLY HALF-ACRE CORNER PARCEL JUST MINUTES FROM PARK AVENUE. Newly priced at $3,950,000, this R-3 ZONED (Medium-Density Residential) property offers outstanding redevelopment potential, INCLUDING CAPACITY FOR UP TO SEVEN RESIDENTIAL UNITS. Ideally positioned between Park Avenue and Winter Park Village, the property offers convenient access to renowned dining and shopping, Rollins College, cultural attractions, AdventHealth Winter Park, and major transportation corridors. Three existing residences occupy the site and contribute no value to the offering. Properties of this size and zoning, so close to Park Avenue, are exceptionally rare. THIS PROPERTY IS CROSS-LISTED AS VACANT LAND WITH THE MLS #O6431538.

540 N Pennsylvania Avenue, Winter Park

1431 Palm Avenue, Winter Park
$799,999
Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code
Welcome to this beautiful lot located in one of Winter Park’s most desirable neighborhoods. This exceptional location presents the perfect opportunity to build your dream home in one of the most sought after school zones Winter Park has to offer. Set along picturesque brick streets shaded by mature trees, the location is hard to beat. It is within walking distance to the beautiful Lake Knowles and Lake Wilbar, just minutes from Park Avenue, the Winter Park YMCA, AdventHealth Winter Park, Rollins College, the Winter Park Chain of Lakes, golf courses, and an abundance of exceptional dining and shopping. Enjoy the chance to create a home tailored to your lifestyle with a perfect blend of classic Winter Park character, beautiful outdoor living, and an unbeatable location.

1431 Palm Avenue, Winter Park

2410 Sherbrooke Road, Winter Park
$769,000
4 Beds ⋅ 3 Baths ⋅ Sherbrooke SubDv. ⋅ 32792 Zip Code
Welcome to 2410 Sherbrooke Rd in Winter Park! This spacious single-story home offers 2,141 sq ft of living space with 4 bedrooms, 2.5 bathrooms, and an attached two-car garage, all in a convenient location within walking distance of Winter Park High School. 10 minutes to Full Sail University, Rollins College, or Downtown Winter Park. Step inside to find generous living and family spaces filled with natural light, beautiful hardwood flooring, and a flexible layout designed for both everyday living and entertaining. The upgraded kitchen features granite countertops, abundant wood cabinetry, stainless steel appliances, recessed lighting, a center island, and a breakfast bar overlooking the family room. The spacious primary suite features new vinyl flooring and an updated en-suite bathroom with dual vanities and a large walk-in shower. Three additional bedrooms provide plenty of flexibility for guests, home office space, or other needs. An additional full bathroom, half bath, and dedicated laundry room complete the interior. French doors lead to the screened patio, offering a comfortable space for outdoor dining and relaxing. Beyond the patio is an exceptionally large backyard surrounded by mature trees and landscaping, with plenty of room for gardening, recreation, entertaining, or creating your own outdoor retreat. Major improvements include a ROOF REPLACED IN 2022 and A/C REPLACED IN 2022, giving the next owner added peace of mind. With its upgraded kitchen and bathrooms, spacious floor plan, beautiful flooring, huge backyard, screened patio, two-car garage, and recently replaced major systems, this Winter Park home offers an outstanding combination of space, comfort, and location. Schedule your private showing today and discover everything this home has to offer!

2410 Sherbrooke Road, Winter Park

822 Symonds Avenue, Winter Park
$599,999
Capens Add SubDv. ⋅ 32789 Zip Code
Build in the heart of Winter Park. This cleared quarter-acre lot (approx. 10,807 sq ft, 50' x 216') sits on Symonds Avenue on the city's west side. It's just blocks from Hannibal Square, Winter Park Village and Martin Luther King Jr. Park, and minutes from the shops and restaurants of Park Avenue. The lot is ready for your plans. It's cleared, with mature shade trees, a paved street with sidewalk, and public water and sewer available. It's zoned R-2, in Flood Zone X, with no HOA. Builders and buyers have room to create a custom home or an investment project in one of Central Florida's most desirable cities. Land this close to Park Avenue rarely comes available. Buyer to verify zoning, setbacks and permitted uses with the City of Winter Park.

822 Symonds Avenue, Winter Park

How much is your home worth?

Get instant property value now!