Winter Park

3 Beds ⋅ 2 Baths ⋅ Ridge High Sub SubDv. ⋅ 32792 Zip Code

Welcome home to Winter Park! This beautifully renovated 3-bedroom, 1.5-bath home offers the perfect combination of classic Florida living and extensive modern updates. Much of the hard work has already been done—just bring your furniture and start enjoying your new home! Step inside to discover new luxury vinyl plank flooring throughout, fresh interior paint, and a bright, refreshed feel. The renovations go well beyond what you can see, including new electrical wiring and electrical panel, new plumbing, and a new HVAC system—major improvements that add comfort and peace of mind for years to come. The exterior has also been freshly painted, giving the home a clean and inviting appearance. And then there’s the backyard! This fabulous oversized outdoor space offers plenty of room to create your own Florida retreat. Add a swimming pool, outdoor kitchen, garden, play area—or perhaps all of the above. There’s room to dream! Located in the highly desirable City of Winter Park, this renovated home provides an opportunity to enjoy one of Central Florida’s most sought-after communities without having to tackle a long renovation list yourself. New flooring, new HVAC, new electrical, updated kitchen and bath, fresh paint inside and out, plus a backyard with serious potential. Come take a look—you may have just found the Winter Park home you’ve been waiting for!

2136 Linden Road, Winter Park

$5,999,990

4 Beds ⋅ 5 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code

Virtually Staged. AN ARCHITECTURAL STATEMENT IN ONE OF WINTER PARK'S MOST COVETED LOCATIONS. Set on a prominent corner lot within exclusive Via Tuscany, this extraordinary new-construction residence by Developer & Builder Group represents far more than exceptional modern design. Its distinction lies equally in what you see and in what you don't see, the extraordinary level of construction, engineering, materials, and craftsmanship behind every detail. Built with reinforced concrete, steel, and iron framing and incorporating exceptionally high construction specifications, the residence was created with an uncompromising commitment to structural integrity, durability, and long-term quality. From its substantial structural components to its impact-resistant glass and carefully sourced materials, the home reflects a philosophy rarely found in residential construction: build beautifully, but build exceptionally well. Offering approximately 4,636 square feet of heated living space and 5,260 total square feet, the residence features 4 bedrooms, 4.5 bathrooms, a private pool, and an attached two-car garage. Expansive floor-to-ceiling impact-resistant Techno Glass walls define the architecture, bringing abundant natural light into the interiors while creating a striking connection between indoor and outdoor living. At the center of the home is a dramatic 16-foot custom Costa One-Tree solid steel installation a true architectural work of art and one of the many elements created specifically for this residence. The same uncompromising approach continues throughout the interiors. Imported Italian porcelain flooring, sophisticated lighting fixtures imported from Greece, and carefully selected European finishes elevate every space. The gourmet kitchen features one-inch-thick Italian quartz countertops, imported Italian cabinetry, an extended entertaining island, premium Wolf appliances, and a Sub-Zero refrigerator. Two luxurious primary suites, one on each level provide exceptional flexibility and privacy, each complemented by a beautifully appointed bath and custom walk-in closet. Private balconies crafted with exquisite boat wood create intimate outdoor retreats, while the private pool completes the home's sophisticated indoor-outdoor lifestyle. The setting is equally exceptional. Via Tuscany offers a coveted Winter Park address near Interlachen Country Club and only minutes from Park Avenue's renowned dining, boutiques, museums, and cultural attractions, with convenient access to Downtown Orlando. This is a residence for the buyer who understands that true luxury is not defined by finishes alone. It is defined by the quality of the materials, the integrity of the construction, the precision of the craftsmanship, and the attention given to what lies behind the walls as much as what is visible within them. RESILIENT BY DESIGN. EXCEPTIONAL BY CONSTRUCTION. REFINED IN EVERY DETAIL.

2661 Via Tuscany, Winter Park

$165,000

2 Beds ⋅ 2 Baths ⋅ Lancelot/Winter Park SubDv. ⋅ 32792 Zip Code

This is exactly what you are looking for! Adorable 2/2 close to Full Sail and UCF. Tons of shopping and restaurants and convenient to the 417 and the 408. Location makes this perfect for a primary residence or investment property. Split floor plan ideal for roommates. Walk to Full Sail. 15 minutes to downtown Orlando and approximately 30 minutes to most attractions. Exceptionally well taken care of and only needs your personal touches to make it a really cute home. Seller will offer an appliance package and a 1 year home warranty with the right contract. What are you waiting for come and get it!!

3651 N Goldenrod Road Unit C109, Winter Park

$1,350,000

Killarney Circle SubDv. ⋅ 32789 Zip Code

Prime Winter Park commercial office building with visibility of monument signage from 1-4 East bound traffic and Ideally situated on Wymore Road. This 2018 built one story office building offers Low-maintenance ownership, with approximately 3021 total square feet, creating a professional office environment with flexible layout options for investors or owner-users. The property features 10 parking spaces includes one handicap with public street parking option located in 32789. Both suites have separate entrances, with access door in between, both with reception areas, open air built-in workspaces. Each suite has its own kitchen and bathroom facilities. Building has 6 total private offices, ( 4 & 2) providing convenience for both administrative and operational functions. Well-constructed, high ceilings, attractive flooring, 2 conference rooms with high-end lighting fixtures, window treatments. Both suites are leased, generating $9,678.60 per month with the tenants' paying utilities, alarm, housekeeping, building taxes, and insurance. One of the tenants' leases (1736 Sq foot suite) expires September 1, 2029 (rental income increases every year) The other suite (1285 sq ft) lease is owner occupied and available for rent immediately or owners are willing to stay up for up to seven months based on new owners' situation. This property offers an excellent opportunity for an owner-occupant of one suite while obtaining rental income. The property manager is the listing RE Agent/seller who will provide a smooth transition upon closing. This property is a prime opportunity for businesses seeking a high-quality, move-in-ready or flex space in one of the area's most accessible commercial corridors.

436 N Wymore Road, Winter Park

$424,900

3 Beds ⋅ 3 Baths ⋅ Enclave At Hawks Crest SubDv. ⋅ 32792 Zip Code

Hawk's Crest is a care free resort style master planned community in Winter Park, Florida. With it's Modern style architecture, this 3 bedroom, 2 1/2 bathroom townhome is meticulously maintained with an HOA that covers more than most. While driving through the community you will pass the community pool and recreation area which is conveniently nestled at the end of Bantam Way. The curb appeal of the paver driveway and home design will make you feel you are home. Inside you will be greeted by a foyer before entering the home itself. On the main floor you will find a half bathroom/ guest bathroom, tile flooring throughout, excellent natural light, living room, dinette, and the statement kitchen sure to please. The kitchen boast granite counter tops, shaker style cabinets, a extra large kitchen island with a breakfast bar, ample size walk-in pantry, refrigerator 2026, all other appliances 2021, new and upgraded kitchen hardware, newer faucet, and newer large single basin sink. Upstairs you will find all the bedrooms, inside laundry room and both full bathrooms, The primary suite is an ample 20 x 15 with trey ceiling, en-suite bathroom, and walk in closet with a custom closet organizer. The en-suite bathroom is highlighted by a dual vanity sink, granite countertops, shaker style cabinets, and shower stall. Both additional bedrooms are an impressive 15 x 12 with walk in closets. The inside laundry room has upgraded cabinets. Out back you will find a quiet covered rear patio with space for seating, a grill, and more. Other highlights to mention include the tesla electric charger in the garage and freshly added cabinets and granite countertops in the drop zone just off the inside garage entrance. Community common areas include a resort style pool with covered social gathering area and a community playground. The HOA covers the cable, internet, community pool, exterior building maintenance, common area maintenance and more. Hawk's Crest is just minutes to Park Avenue Winter Park, 417, UCF, shopping, restaurants and much more. Just a short walk to the out-parcel building in the front of the community you will find local favorites like Foxtail coffee, Kelly's Ice cream, and the Park Maitland School. Don't miss this opportunity. These townhomes go quickly.

1521 Bantam Way, Winter Park

$2,350,000

3 Beds ⋅ 4 Baths ⋅ Versailles Winter Park Condo SubDv. ⋅ 32789 Zip Code

Welcome to The Versailles of Winter Park, an extraordinary opportunity to own one of only seven exclusive private residences in one of Winter Park's most coveted luxury communities, nestled just steps from the world-renowned Park Avenue and adjacent to the prestigious Alfond Inn & Spa. This magnificent third-floor residence offers 3,110 square feet of impeccably designed one-level living, oak hardwood floors throughout, elegant crown molding, and an abundance of natural light pouring through French doors set the tone for refined sophistication. Entertain effortlessly in the grand living area with a sprawling balcony adorned with Chicago brick and stone railing. Kitchen includes wood cabinet, granite, Monogram refrigerator, convection oven and microwave. The versatile split-bedroom floor plan ensures ultimate privacy, with the lavish primary suite accessed through double doors, walk-in closet, private balcony access, and an opulent spa bath featuring dual vanities, a soaking tub, walk-in shower. A designated office with wall-to-wall built-ins, a formal dining room accommodating up to twelve guests, a private two-car garage, and meticulously maintained landscaping. The Versailles of Winter Park is the ultimate expression of luxury living offering an unparalleled lifestyle just moments from the finest dining, boutique shopping, art festivals, and cultural events that makes Winter Park one of Florida's most desirable destinations.

200 S Interlachen Avenue Unit 350, Winter Park

$1,395,000

4 Beds ⋅ 4 Baths ⋅ Bear Gully Pointe SubDv. ⋅ 32792 Zip Code

Welcome to 2873 Old Castle Drive, an exceptional property located within the sought-after gated community of Bear Gully Pointe in Winter Park. Nestled along the shores of Bear Lake, a 137- acre spring-fed lake, this stunning estate-like property sits on more than half an acre and is surrounded by lush landscaping, mature trees and beautifully maintained grounds. From the moment you arrive, the long, newly paved driveway sets the tone for what awaits. Meticulously maintained, this impressive home offers 4 bedrooms, 4 full bathrooms, a dedicated office and a spacious upstairs loft/bonus room. The dramatic entry features soaring ceilings, expansive windows and sliding glass doors that draw your attention to the pool and picturesque backyard. The formal dining room, accented by coffered ceilings, flows seamlessly into the beautifully appointed kitchen through a wet bar and wine closet. Completely reimagined down to the studs in 2016, the kitchen features gorgeous marble countertops, custom cabinetry with built-in drawers, a brand-new gas cooktop, double wall ovens, Sub-Zero refrigerator, generous breakfast nook and a large picture window overlooking the pool. The kitchen opens directly to the spacious family room, where soaring ceilings, floor- to-ceiling windows, a gas fireplace and custom built-in cabinetry create an inviting gathering space. A secondary bedroom and full bathroom are conveniently located just off the family room. The expansive downstairs primary suite is a true retreat, featuring tall ceilings, abundant windows and a French door providing direct access to the pool and lanai. Completely remodeled in 2019, the luxurious primary bath offers two separate vanities with dual sinks, a spacious shower with dual shower heads, a beautiful soaking tub and a custom walk-in closet. Just beyond the primary suite is a dedicated office and convenient pool bath. Upstairs, a separate living area provides exceptional flexibility with a generous loft/bonus room, two spacious bedrooms and a full bath featuring dual sinks, a soaking tub and separate shower. Designed with entertaining in mind, the home’s indoor and outdoor spaces blend effortlessly together. The heated pool and spa are surrounded by a covered, screened lanai and a lush backyard oasis complete with mature trees and charming walking paths—creating a private setting for relaxing or entertaining. Bear Gully Pointe offers sidewalks throughout the community, a tennis court, playground and a brand-new gazebo overlooking Bear Lake. Ideally located just minutes from downtown Winter Park, Trinity Preparatory School, Winter Springs and Oviedo. Additional updates include a 2021 roof, 2022 gas water heater, 2024 re-pipe, 2016 pool resurfacing, 2025 driveway, 2022 exterior paint and hardwood flooring downstairs added in 2013.

2873 Old Castle Drive, Winter Park

$669,900

3 Beds ⋅ 2 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code

Bright, airy, and designed for a resort living! Welcome to a turn-key Winter Park Pine home where everyday life feels like a getaway! From the moment you enter, you will appreciate the home's refined modern aesthetic, clean architectural lines, and thoughtfully curated finishes. Brand new flooring creates a seamless sense of elegance throughout, while sleek new cabinetry, contemporary finishes, and new premium appliances, and new quartz counters is suited for dinning or entertaining! Through sliding glass doors lies the crown jewel: a sparkling, screened in-ground pool surrounded by a luxury private patio! Spend time hosting barbecues under the covered lanai or relaxing in the warm afternoon sun! Yard is fully fenced! Private backyard featuring a plenty sitting areas and a brand-new fire pit for wonderful outdoor gatherings! Whether you are doing morning exercise or watching the sunset by the water, it delivers a peaceful resort living! Living in this renown Winter Park Pine neighborhood with No HOA, yet easy access to golf courses, biking trails and parks, community amenities, Advent hospital, Park Ave, Rollin College and Baldwin Park! Renown school districts and convenient locations! Don't miss out on this rare find—call now to see it in person!

274 N Ranger Boulevard, Winter Park

$245,000

2 Beds ⋅ 2 Baths ⋅ Mead Garden SubDv. ⋅ 32789 Zip Code

Virtually Staged. Updated two-bedroom, two-bath residence offering 908 square feet and a first-floor, pool-facing location in Mead Garden Condominium. The move-in-ready interior features luxury vinyl plank flooring throughout the living areas and bedrooms, tile flooring in the baths and defined living and dining spaces. The kitchen is appointed with white transitional cabinetry, granite countertops, a white subway tile backsplash and stainless steel appliances, including a refrigerator, range, microwave and dishwasher. A pass-through to the dining area incorporates built-in cabinetry, glass-front display storage and additional counter space. The dining area flows into the living room, where sliding glass doors open to an enclosed sunroom overlooking the community pool and landscaped grounds. The primary bedroom features natural light from a pool-facing window, built-in closet storage and an en-suite bath with a walk-in shower and white tile surround. A second bedroom provides flexible space for a variety of uses, while the second full bath offers a tub and shower combination. Additional features include a newer air-conditioning system and water heater, updated plumbing fixtures and convenient access to the community laundry room just outside the residence. From 1250 South Denning Drive, Residence 127 offers proximity to Mead Botanical Garden, Rollins College, Park Avenue, Azalea Park, Seven Oaks Park and Winter Park dining and retail.

1250 S Denning Drive Unit 127, Winter Park

$299,990

3 Beds ⋅ 2 Baths ⋅ Windward Square Sec 3 SubDv. ⋅ 32792 Zip Code

Great opportunity in the established Windward Square community of Winter Park! This END-UNIT home offers 3 bedrooms, 2 full bathrooms and approximately 1,467 square feet of living space, with added privacy and plenty of potential. ROOF REPLACED IN 2017! The home is ready for some TLC and personal updates, giving the next owner the opportunity to renovate and make it their own. The spacious living and dining areas gives a functional layout, while the large screened porch provides additional space to relax, entertain, and enjoy Florida living. Being located at the end provides additional privacy and a more open feel compared with interior units. The community offers amenities including a swimming pool and tennis courts. Conveniently located near shopping, dining and major roadways, with easy access to Winter Park, Orlando and surrounding areas. Whether you’re looking for a primary residence or an investment opportunity, this property offers great potential and an excellent opportunity to add value through your own improvements. Bring your vision and make this home your own!

2275 Island Run, Winter Park

$639,000

3 Beds ⋅ 2 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32792 Zip Code

Completely renovated and move-in ready, this beautifully updated Winter Park home offers a fresh, modern interior without the hassle of renovations. The brand-new kitchen features new cabinetry, quartz countertops and all new appliances, while both bathrooms have been fully renovated with new finishes and fixtures. New luxury vinyl plank flooring runs throughout the home, complemented by fresh interior paint. The roof was replaced in April 2022, providing added peace of mind for today's buyer. With 3 bedrooms, 2 bathrooms and approximately 1,785 square feet of living space, this home offers a comfortable and functional floor plan in an established Winter Park location. The spacious yard offers plenty of room for outdoor enjoyment and the opportunity to create your own ideal landscaping. Enjoy easy access to Cady Way Park and the Cady Way Trail, perfect for walking, biking and recreation. Just minutes from the restaurants, shopping and charm of Park Avenue, as well as the popular Baldwin Park area. Conveniently located near AdventHealth Winter Park and numerous dining, shopping and recreational options. Agent owned property.

508 Brechin Drive, Winter Park

$1,300,000

3 Beds ⋅ 3 Baths ⋅ Edgewood Sub SubDv. ⋅ 32789 Zip Code

WELCOME TO CONTEMPORARY LUXURY IN THE HEART OF WINTER PARK! This stunning two-story pool residence has been beautifully remodeled from top to bottom and offers high end design, high-end finishes and an exceptional lifestyle location near East End Market, Baldwin Park, Audubon Park and all of Winter Parks charm. Behind the private gated courtyard and modern fencing, discover a thoughtfully designed home featuring custom built-ins, designer finishes, porcelain tile, custom wood-plank stairs and a dramatic modern glass railing. The beautifully appointed kitchen is designed for both entertaining and everyday living and features premium Wolf gas cooking appliances with range hood, Sub-Zero refrigerator, stainless steel wine refrigerator, microwave, stainless farmhouse sink, pantry and stylish pendant lighting. The open living areas provide a wonderful setting for gathering and entertaining. The downstairs primary suite offers convenience, privacy and direct access to the spectacular outdoor pool living area. The luxurious en-suite bath features dual vanities, custom cabinetry and mirrors, high-end designer fixtures, beautiful tile work and a spacious glass-enclosed shower. Upstairs, you will find generously sized bedrooms, custom closet spaces and a beautifully finished bonus room offers exceptional flexibility for a home office, fitness room, exercise space, storage or additional flex space. Additional features include a dedicated first floor laundry room and powder room, upstairs linen closet, designer lighting through out and a two-car garage. Step outside to your own private retreat! The covered lanai flows seamlessly to the beautiful custom pool and outdoor entertaining area featuring a gas fire pit. Mature bamboo landscaping, a fenced yard and contemporary entrance fencing create a private and inviting setting. LOCATION, LOCATION, LOCATION! Enjoy the highly desirable Winter Park lifestyle with convenient access to East End Market, local coffee shops, exceptional restaurants, specialty shopping, markets and community events. Nearby destinations include Leu Gardens, Baldwin Park, Park Avenue and Downtown Winter Park. Zoned for Audubon Park School (K-8) and Winter Park High School; buyers should verify school assignments and enrollment eligibility. This exceptional move-in-ready home combines contemporary luxury, resort-style outdoor living and one of Central Florida’s most desirable lifestyle locations!

1922 Hammerlin Avenue, Winter Park

$425,000

3 Beds ⋅ 3 Baths ⋅ Enclave At Hawks Crest SubDv. ⋅ 32792 Zip Code

Welcome to the Enclave at Hawks Crest, where this modern 3-bedroom, 2.5-bath townhome gives you 1,755 square feet of space without a long list of things to maintain. A paver driveway, two-car garage, and clean exterior make a great first impression, and inside, high ceilings and plenty of natural light keep the main level feeling open and bright. The kitchen sits right in the middle of it all with a large island, stainless steel appliances, and a walk-in pantry, opening naturally to the dining and living areas. Out back, sliding doors lead to a covered, screened patio overlooking greenspace, giving you a little breathing room without a backyard to take care of. Upstairs, the primary suite is spacious with a tray ceiling, large walk-in closet, and ensuite bath with dual sinks and a tiled shower. Two additional bedrooms sit at the opposite end of the hall, along with a second full bath and, thankfully, the laundry room is upstairs too. This home has been meticulously maintained by its original owner since 2021. The HOA handles the exterior and landscaping, and the gated community includes a resort-style pool, playground, and dog park. Zoned for A-rated Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High, and you're just minutes from Park Avenue, with Kelly's Ice Cream and Foxtail Coffee a short walk from your front door. Low maintenance, high convenience, and Winter Park right outside your door. Call today for your private showing!

2349 Shadowland Loop, Winter Park

$1,000,000

Harbor East SubDv. ⋅ 32792 Zip Code

REMARKABLE LAND OPPORTUNITY IN WINTER PARK! Welcome to an exceptional real estate offering situated on 4.93 level, usable acres in the highly desirable Winter Park area (Zip Code 32792). This unique property features both an existing mobile home and a separate concrete block home, presenting an incredible value-add situation for investors, developers, or buyers looking for a place to live while planning their next big project. The vast, cleared land is the ultimate blank canvas, perfect for building your custom luxury dream home, establishing a family compound, or exploring potential multi-family development opportunities (subject to Orange County zoning and approvals). Location is everything, and this property delivers: you are just minutes from the University of Central Florida (UCF), premier shopping centers, major dining, Orlando International Airport (OIA), and all the world-class entertainment that the greater Orlando area has. Whether you want a private sanctuary with acreage, a rental income generator, or a strategic land hold with high future upside, this rare find checks every box. Do not miss out on this extraordinary piece of Central Florida real estate!

7839 University Garden Drive, Winter Park

$360,000

4 Beds ⋅ 3 Baths ⋅ Ridge High Sub SubDv. ⋅ 32792 Zip Code

Great investment opportunity in Winter Park. 4 bedroom 2.5 bathroom. Large covered patio overlooks huge completely fenced back yard. New roof 2025, HVAC system 2020, water heater 2024 and upgraded electric panel re-piping of water system with Pex in 2010. Terrazzo flooring through most of the home. Excellent Seminole County neighborhood located just minutes to Downtown Winter Park, City of Orlando, Orlando International Airport, UCF & Full Sail Universities, Rollins College, Banking, Shopping & Winter Park Hospital. Within 1 hour of area attractions, Atlantic Coast Beaches, Cap Canaveral.

2122 Ridge Drive, Winter Park

$349,500

2 Beds ⋅ 1 Baths ⋅ Village Condos SubDv. ⋅ 32789 Zip Code

Virtually Staged. **Rare opportunity to own in the highly desired Downtown of Winter Park for under $350,000!** Enjoy the highly desired downtown Winter Park lifestyle with Park Avenue’s boutiques, restaurants, cafés, arts and culture, Rollins College, the Winter Park Train station, Casa Feliz, seasonal festivals and community events all just a short walk from your front door. This charming 2-bedroom, 1-bath condo offers an inviting open-concept living and dining area, along with a kitchen featuring granite countertops and convenient counter seating. Condo is highlighted with beautiful plantation shutters. Located within a charming, intimate condominium community, it offers a wonderful combination of comfort, location and low-maintenance living, all within an area known for its highly regarded Winter Park-area schools. Whether you’re searching for a primary residence, a second home, a great option for downsizing, or an investment property, this is your opportunity to own a piece of one of Central Florida’s most desirable cities. Imagine strolling to dinner on Park Avenue, meeting friends for coffee, walking to Rollins College, enjoying the beauty and history of Casa Feliz, browsing the shops, attending an art festival or catching the train — all without worrying about finding a parking space. Simply walk out your front door and enjoy the incredible lifestyle that makes Winter Park such a special place to call home. **Opportunities to own downtown Winter Park real estate at this price point are rare. Don’t miss your chance — schedule your private showing today before this one is sold. A location and lifestyle like this won’t last long!**

500 N Pennsylvania Avenue Unit G, Winter Park

$135,000

2 Beds ⋅ 2 Baths ⋅ Parkview Village SubDv. ⋅ 32792 Zip Code

VALUE OPPORTUNITY IN WINTER PARK! Welcome to 3020 Antique Oaks Circle #129, a spacious 2-bedroom, 2-bath FIRST-FLOOR CONDO offering approximately 1,018 square feet in the conveniently located Parkview Village community in Winter Park, FL 32792. If you have been searching for an affordable Winter Park condo, investment property, renovation opportunity, first-floor condo or 2-bedroom condo in Winter Park, this property deserves your attention. The functional floor plan offers generous living space, two full bathrooms, an interior laundry area and the convenience of first-floor living. Parkview Village offers desirable community amenities including a COMMUNITY POOL, SPA, TENNIS COURTS and recreational areas, creating an appealing combination of location, convenience and value. LOCATION IS A MAJOR HIGHLIGHT! Enjoy easy access to Semoran Boulevard/436, Aloma Avenue, University Boulevard, Downtown Winter Park, Park Avenue, Rollins College, UCF and major Central Florida roadways. Shopping, restaurants, grocery stores and everyday conveniences are close by, making this an excellent option for buyers looking for a Winter Park condo close to dining, shopping, entertainment and employment centers. The property is currently served by Aloma Elementary School, Glenridge Middle School and Winter Park High School. Buyers are encouraged to independently verify current school zoning and assignments with Orange County Public Schools. IMPORTANT VALUE OPPORTUNITY: The property has known mold present in the kitchen area that requires professional remediation, and the asking price has been positioned to reflect the property's current condition and the work needed. This creates an opportunity for a buyer who is prepared to complete the necessary remediation and customize the property to their own style. Buyers are encouraged to perform their own inspections, obtain professional remediation evaluations and verify all property and association information. With a Winter Park address, first-floor location, 2 bedrooms, 2 full bathrooms, community amenities and convenient access to shopping, dining and major roadways, this condo offers significant potential for the buyer willing to address the existing condition. Bring your vision and take advantage of this affordable Winter Park condo opportunity!

3020 Antique Oaks Circle Unit 129, Winter Park

$130,000

1 Beds ⋅ 1 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code

It doesn't get much better than this: Living in a Lakefront and Winter Park community, that is convenient to I-4 providing easy access to points north and south, downtown Winter Park, shopping, fine dining, and the price can't be beat. The HOA dues includes water, trash pickup, a full package from Spectrum including internet. Lakeside Manor is situated on the north side of Lake Killarney, a 239 acre lake that is perfect for sailing, motor boating and skiing. The lush courtyard, lakeside pool, clubhouse and gazebo, updated dock and private boat ramp make this a serene place to enjoy the best of Central Florida in a noisy world. This one bedroom condo is in original condition, with 3 year old A/C unit, and is ready for your personal touches to make it your own.

2500 Lee Road Unit 143, Winter Park

$1,350,000

4 Beds ⋅ 4 Baths ⋅ Elizabeth Heights Sub SubDv. ⋅ 32789 Zip Code

Modern Winter Park living meets exceptional convenience at this beautifully designed 2023 residence, ideally positioned near Park Avenue and just minutes from Downtown Orlando. Offering nearly 3,000 square feet of thoughtfully designed living space, this 4-bedroom, 4-bath home combines contemporary architecture, abundant natural light, and elevated finishes in one of Central Florida’s most sought-after locations. Oversized windows and an open-concept layout create a bright, seamless connection between the living, dining, and kitchen spaces—equally suited for everyday living and entertaining. At the heart of the home, the gourmet kitchen features premium stainless steel appliances, custom cabinetry, designer backsplash and lighting, and an oversized island with dramatic waterfall-edge quartz countertops and generous seating. The thoughtfully designed floor plan includes a first-floor guest suite and full bath, providing privacy and flexibility for overnight guests, multigenerational living, or a private home office. Upstairs, the spacious primary retreat features a spa-inspired bath with dual vanities, soaking tub, oversized walk-in shower, and a generous walk-in closet enhanced with a custom organization system. Two additional bedroom suites complete the second level. Outside, the fully fenced backyard and covered lanai with summer kitchen create an inviting extension of the home’s living space—perfect for outdoor dining and entertaining year-round. Additional highlights include designer LED lighting, abundant storage, a two-car garage, manicured landscaping, and no HOA. Located near shopping, dining, highly rated schools, Park Avenue, and the best of Winter Park and Orlando, 1320 Orchid Avenue offers the rare opportunity to enjoy newer construction, modern design, and an exceptional location without sacrificing space or privacy. Schedule your private showing today.

1320 Orchid Avenue, Winter Park

$495,000

4 Beds ⋅ 2 Baths ⋅ Wrenwood Unit 3 3rd Add SubDv. ⋅ 32792 Zip Code

UPDATED 4-BEDROOM POOL HOME IN WINTER PARK WITH NO HOA! Welcome to 3020 Nicholson Drive, a beautifully updated 4-bedroom, 2-bath home with a private pool, 2-car garage, and NO HOA, tucked into the established Wrenwood neighborhood of Winter Park. From the thoughtfully updated interior to the backyard designed for Florida living, this home offers the space, flexibility, and location you've been looking for. Step inside to a bright and inviting interior featuring new LVP flooring throughout, a split-bedroom floor plan, and multiple living and dining spaces that provide plenty of room to spread out, gather, and entertain. The kitchen features abundant cabinetry and counter space, stone countertops, a built-in oven and cooktop, and a window overlooking the backyard. Custom epoxy flooring in the kitchen and entry adds durability and a unique finishing touch. The primary suite is one of the home's standout spaces, featuring a beautifully remodeled bathroom with a double vanity and an oversized glass-enclosed shower, along with a custom-built closet with shelving and organization designed to maximize storage and functionality. But the backyard may be where you'll want to spend most of your time. Step outside to a private in-ground pool, covered screened patio, fenced backyard, and an expanded pool deck with additional pavers, creating multiple spaces to lounge, entertain, dine outdoors, or simply enjoy the Florida sunshine. There's even green space beyond the pool, giving the backyard a more open feel than you might expect from a pool home. The home also offers important improvements already completed for you, including a roof replaced in 2019, re-pipe completed in 2013, and HVAC system replaced in 2018/2019. A professionally installed security system and security cameras add another layer of functionality. The location ties it all together. Situated in Winter Park's Wrenwood neighborhood, 3020 Nicholson Drive puts you within easy reach of some of Central Florida's favorite destinations, including Park Avenue, Winter Park Village, and Baldwin Park, with shopping, dining, entertainment, and everyday conveniences nearby. Convenient access to SR 436 and the 408 also makes it easy to reach Downtown Orlando and destinations throughout Central Florida.

3020 Nicholson Drive, Winter Park

Downtown Winter Park

Brand New Winter Park Listings