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Millsboro, DE Condos for Sale

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  • 33571 Windswept Dr Unit 9101, Millsboro, DE 19966
    33571 Windswept Dr Unit 9101, Millsboro, DE 19966
    33571 Windswept Dr Unit 9101, Millsboro, DE 19966
    /75

    $340,000

    • 3 Beds
    • 2 Baths
    • 1,677 Sq Ft

    33571 Windswept Dr Unit 9101, Millsboro, DE 19966

    $5,000 SELLER CREDIT if a contract settles before 6/1/2026!! Best value three bedroom condominium in the Peninsula. Welcome to Windswept Drive, Unit 9101! Perfectly positioned along the 6th fairway of the Jack Nicklaus Signature golf course, this residence enjoys a peaceful, private backdrop of golf, ponds and woods, with glimpses stretching toward the Indian River Bay. A pergola-covered patio

    Valerie Ellenberger Compass

    33571 Windswept Dr Unit 9101, Millsboro, DE 19966
  • 33564 Windswept Dr Unit 2301, Millsboro, DE 19966
    33564 Windswept Dr Unit 2301, Millsboro, DE 19966
    33564 Windswept Dr Unit 2301, Millsboro, DE 19966
    /53

    $419,900

    • 3 Beds
    • 2.5 Baths
    • 1,860 Sq Ft

    33564 Windswept Dr Unit 2301, Millsboro, DE 19966

    UPSCALE COASTAL RETREAT WITH OVERSIZED GARAGE! Welcome to this top-floor end-unit condo in the sought-after community of The Peninsula on the Indian River Bay. This beautifully cared-for home offers a spacious, light-filled layout with 3 bedrooms and 2.5 baths, blending coastal comfort with elegant design. Gorgeous hardwood floors, thoughtful architectural touches, and large picture windows

    Lee Ann Wilkinson Berkshire Hathaway HomeServices PenFed Realty

    33564 Windswept Dr Unit 2301, Millsboro, DE 19966
  • 33584 Windswept Dr Unit 5401, Millsboro, DE 19966
    33584 Windswept Dr Unit 5401, Millsboro, DE 19966
    33584 Windswept Dr Unit 5401, Millsboro, DE 19966
    /16

    $359,000

    • 3 Beds
    • 2 Baths
    • 1,894 Sq Ft

    33584 Windswept Dr Unit 5401, Millsboro, DE 19966

    This top floor, corner unit condo is situated in the amenity-rich community of The Peninsula on the Indian River Bay. It has three bedrooms, two full baths, an open floor plan, 9-foot ceilings, built-in bookcases flanking a gas fireplace, LVP flooring throughout the living areas, carpeting in the bedrooms, tile in the kitchen and bathrooms plus a neutral color palette. The kitchen features a

    TIFFINI ANDERSON Jack Lingo - Rehoboth

    33584 Windswept Dr Unit 5401, Millsboro, DE 19966
  • 33580 Windswept Dr Unit 4307, Millsboro, DE 19966
    33580 Windswept Dr Unit 4307, Millsboro, DE 19966
    33580 Windswept Dr Unit 4307, Millsboro, DE 19966
    /34

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,860 Sq Ft

    33580 Windswept Dr Unit 4307, Millsboro, DE 19966

    Resort-style living at its finest in this quiet, top-floor end unit — one of the most unique and rarely available residences in Windswept at The Peninsula. This exceptional “Bonita” model is part of a highly limited collection — only 13 Bonita units were ever built in Windswept. They are the largest floor plans of their kind and the only end units of this size. Even more rare, only four

    Michael McKee Long & Foster Real Estate, Inc.

    33580 Windswept Dr Unit 4307, Millsboro, DE 19966
  • 33580 Windswept Dr Unit 4207, Millsboro, DE 19966
    33580 Windswept Dr Unit 4207, Millsboro, DE 19966
    33580 Windswept Dr Unit 4207, Millsboro, DE 19966
    /49

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,865 Sq Ft

    33580 Windswept Dr Unit 4207, Millsboro, DE 19966

    Welcome to 33580 Windswept, unit 4207, a beautifully appointed three-bedroom, two-bath condo in the sought-after Peninsula community. With an unbeatable location you will enjoy being close to the clubhouse, pools, golf course, tennis courts, bay, and more, this home places you at the center of an active, amenity-filled lifestyle while offering stylish, stress free, low-maintenance living. The

    Jim Lattanzi Northrop Realty

    33580 Windswept Dr Unit 4207, Millsboro, DE 19966
  • 33585 Windswept Dr Unit 7303, Millsboro, DE 19966
    33585 Windswept Dr Unit 7303, Millsboro, DE 19966
    33585 Windswept Dr Unit 7303, Millsboro, DE 19966
    /49

    $329,000

    • 2 Beds
    • 2 Baths
    • 1,325 Sq Ft

    33585 Windswept Dr Unit 7303, Millsboro, DE 19966

    JUST REDUCED...Welcome to 33585 Windswept Drive #7303 in the highly sought-after Peninsula community of Millsboro. This beautifully appointed Sanibel model by Schell Brothers offers coastal elegance, golf course views, and resort-style living just minutes from the Indian River Bay. Located on the second level with elevator access this 2 bedroom, 2 bath condominium offers approximately 1,325

    Chrisy Tingle Keller Williams Realty

    33585 Windswept Dr Unit 7303, Millsboro, DE 19966
  • 4306 Caitlins Way Unit 4306, Millsboro, DE 19966
    4306 Caitlins Way Unit 4306, Millsboro, DE 19966
    4306 Caitlins Way Unit 4306, Millsboro, DE 19966
    /24

    $240,000

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    4306 Caitlins Way Unit 4306, Millsboro, DE 19966

    This one will not last long! Located in the Villages at Millwood is where you will find this beautifully refreshed 3 bedroom, 2 bathroom condo located in a desirable elevator building. Step inside and discover the open floor plan designed for everyday living. The living and dining areas flow seamlessly to the kitchen with large island and new stainless steel appliances. The primary suite offers a

    SHERRY MITCHELL INDIAN RIVER LAND CO

    4306 Caitlins Way Unit 4306, Millsboro, DE 19966
  • 33564 Windswept Dr Unit 2102, Millsboro, DE 19966
    33564 Windswept Dr Unit 2102, Millsboro, DE 19966
    33564 Windswept Dr Unit 2102, Millsboro, DE 19966
    /67

    $449,000

    • 3 Beds
    • 3 Baths
    • 1,860 Sq Ft

    33564 Windswept Dr Unit 2102, Millsboro, DE 19966

    Presenting 33564 Windswept Drive, an exceptional first floor condominium nestled in the prestigious community of 'The Peninsula on the Indian River Bay'. This impeccably maintained residence boasts a spacious and inviting layout, featuring three bedrooms each with their own dedicated bathroom. Every inch of this property exudes sophistication and charm - from the elegant living space, filled with

    John Rishko Patterson-Schwartz-Rehoboth

    33564 Windswept Dr Unit 2102, Millsboro, DE 19966
  • 3202 Caitlins Way, Millsboro, DE 19966
    3202 Caitlins Way, Millsboro, DE 19966
    3202 Caitlins Way, Millsboro, DE 19966
    /19

    $229,000

    • 2 Beds
    • 2 Baths
    • 729 Sq Ft

    3202 Caitlins Way, Millsboro, DE 19966

    Welcome to the Villages of Millwood, where you'll find this cozy 2-BR, 2-BA Condo. Recent improvements include new laminate flooring and new water heater. Extras include appliances and sliding glass doors leading to the screened porch and deck. The Villages at Millwood is ideally located near Millsboro's shopping, dining, and everyday conveniences. Just a short drive away, enjoy the Delaware

    Tina Moore The Real Estate Market

    3202 Caitlins Way, Millsboro, DE 19966
  • 33586 Windswept Dr Unit 6405, Millsboro, DE 19966
    33586 Windswept Dr Unit 6405, Millsboro, DE 19966
    33586 Windswept Dr Unit 6405, Millsboro, DE 19966
    /26

    $298,500

    • 2 Beds
    • 2 Baths
    • 1,325 Sq Ft

    33586 Windswept Dr Unit 6405, Millsboro, DE 19966

    TOP FLOOR! and the lowest price! Move-in ready to this beautifully maintained, charming, 2 bedrooms, 2 en suite bath, condo. NEW Luxury vinyl plank flooring! Enjoy the spacious open living area, with adjacent dining area, GE profile stainless appliances, granite countertops , crown molding, recessed lighting, ceiling fans, built-ins and a lovely gas fireplace that compliments this stylish home.

    Valerie Ellenberger Compass

    33586 Windswept Dr Unit 6405, Millsboro, DE 19966
  • 33579 Windswept Dr Unit 8205, Millsboro, DE 19966
    33579 Windswept Dr Unit 8205, Millsboro, DE 19966
    33579 Windswept Dr Unit 8205, Millsboro, DE 19966
    /47

    $299,000 Open Sun 1:15PM - 2:45PM

    • 2 Beds
    • 2 Baths
    • 1,397 Sq Ft

    33579 Windswept Dr Unit 8205, Millsboro, DE 19966

    Beautifully upgraded and freshly painted 2-bedroom condo featuring durable hardwood laminate floors, a modern kitchen with granite countertops and stainless-steel appliances, a cozy gas fireplace with built-in cabinetry, and elegant crown molding. Both bedrooms are master suites with private ensuite baths, offering comfort and privacy. Enjoy convenient living and a serene, screened porch

    Judith Dourgarian Northrop Realty

    33579 Windswept Dr Unit 8205, Millsboro, DE 19966
  • 5106 Caitlins Way, Millsboro, DE 19966
    5106 Caitlins Way, Millsboro, DE 19966
    5106 Caitlins Way, Millsboro, DE 19966
    /33

    $275,000

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    5106 Caitlins Way, Millsboro, DE 19966

    Charming 3-Bedroom Condo in Villages at Millwood – Millsboro, DEWelcome to easy living in the heart of Millsboro! This beautifully maintained 3-bedroom, 2-bath first-floor condo is located in the desirable Villages at Millwood—a vibrant community known for its comfort, convenience, and charm. Step inside to find a spacious open-concept layout with plenty of natural light, a well-appointed

    MARIAN CAMPO Iron Valley Real Estate at The Beach

    5106 Caitlins Way, Millsboro, DE 19966
  • 5205 Caitlins Way, Millsboro, DE 19966
    5205 Caitlins Way, Millsboro, DE 19966
    5205 Caitlins Way, Millsboro, DE 19966
    /30

    $239,900

    • 2 Beds
    • 2 Baths
    • 900 Sq Ft

    5205 Caitlins Way, Millsboro, DE 19966

    Welcome to 5205 Caitlins Way, located in the desirable Villages at Millwood in Millsboro—where comfort, convenience, and coastal charm come together. This beautifully maintained 2-bedroom, 2 full bath home offers effortless, move-in-ready living with an inviting open floor plan designed for both relaxation and entertaining. The spacious primary suite features a walk-in closet, while the main

    Amanda Sweigert Keller Williams Realty Delmarva

    5205 Caitlins Way, Millsboro, DE 19966
  • 33564 Windswept Dr Unit 2303, Millsboro, DE 19966
    33564 Windswept Dr Unit 2303, Millsboro, DE 19966
    33564 Windswept Dr Unit 2303, Millsboro, DE 19966
    /9

    $494,500 Coming Soon

    • 3 Beds
    • 3 Baths
    • 1,937 Sq Ft

    33564 Windswept Dr Unit 2303, Millsboro, DE 19966

    Coming Soon! Stay tuned for professional photography, detailed listing information, and full MLS details coming soon.

    Adam monico Coldwell Banker Realty

    33564 Windswept Dr Unit 2303, Millsboro, DE 19966
  • 5306 Caitlins Way, Millsboro, DE 19966
    5306 Caitlins Way, Millsboro, DE 19966
    5306 Caitlins Way, Millsboro, DE 19966
    /27

    $269,999

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    5306 Caitlins Way, Millsboro, DE 19966

    Welcome to living in the Villages at Millwood! This building includes an elevator to take you to this beautiful 3-bedroom, 2-bath third-floor unit. It offers a bright and open layout designed for both comfort and convenience. Step inside to find an open-concept kitchen and living room, perfect for everyday living and entertaining. The kitchen features a center island with bar seating, providing

    Pamela Price Berkshire Hathaway HomeServices PenFed Realty

    5306 Caitlins Way, Millsboro, DE 19966
  • 33580 Windswept Dr Unit 4202, Millsboro, DE 19966
    33580 Windswept Dr Unit 4202, Millsboro, DE 19966
    33580 Windswept Dr Unit 4202, Millsboro, DE 19966
    /67

    $315,000

    • 2 Beds
    • 2 Baths
    • 1,323 Sq Ft

    33580 Windswept Dr Unit 4202, Millsboro, DE 19966

    Fully furnished - Turnkey. Welcome to Windswept Condominiums in The Peninsula, Coastal Delaware’s premier private gated country club community, where luxury living meets a resort-style lifestyle. 800 acres located on the Indian River Bay with private sandy beaches. Ideally positioned just steps from the Clubhouse, this home provides effortless access to world-class amenities, dining, and social

    Paul Maltaghati Monument Sotheby's International Realty

    33580 Windswept Dr Unit 4202, Millsboro, DE 19966
Delaware Sussex County Millsboro

Condos for Sale in Millsboro, DE

Why Live in Millsboro

Millsboro, Delaware, a small town in Sussex County, has seen significant growth over the past two decades, transforming from a 19th-century mill town into a thriving community. With a population of around 7,700, Millsboro maintains a quiet, small-town atmosphere despite its development. The town's proximity to Rehoboth Beach and Bethany Beach, both about a 30-minute drive away, has contributed to its appeal. Millsboro features New Traditional-style homes, with ongoing developments like The Peninsula offering craftsman-style and stilt-style houses along the bay and golf courses. Other notable golf course communities include Plantation Lakes and Baywood Greens. The town experiences all four seasons, with occasional heavy rainfall and tropical storms necessitating flood insurance for homes near the river. Cupola Park, home to Delaware's largest bald cypress tree, offers boat ramps and fishing, while W.B. Atkins Memorial Park hosts the annual Stars and Stripes event. Downtown Millsboro boasts breakfast cafes, antique stores, and the Millsboro Christmas Parade, while Peninsula Crossing provides grocery stores and big-box retailers. The Indian River School District, serving the town, is highly rated, offering quality education to nearly 10,800 students. Major highways like U.S. Route 113 facilitate access to Dover, Philadelphia, and Washington, D.C., with the Salisbury Regional Airport 25 miles south. Medical facilities include Beebe Healthcare's South Coastal Emergency Department, with plans for a new emergency room featuring a pediatric unit and helicopter pad.

Learn more about living in Millsboro

Home Trends in Millsboro, DE

On average, homes in Millsboro, DE sell after 74 days on the market compared to the national average of 56 days. The median sale price for homes in Millsboro, DE over the last 12 months is $393,020, down 9% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$393,020
Median Single Family Sale Price
$424,990
Median Townhouse Sale Price
$334,320
Median 2 Bedroom Sale Price
$310,000
Median 1 Bedroom Sale Price
$160,000
Average Price Per Sq Ft
$216
Number of Homes for Sale
446
Last 12 months Home Sales
969
Months of Supply
5.50
Median List Price
$409,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-9%
How to Buy a Home How to Finance a Home How to Sell a Home

In Millsboro, there are currently 16 condos for sale, providing a variety of options for potential buyers. With condos priced between $229,000 to $494,500, there's a range to accomodate every budget. As of April, 2026 the median home price in Millsboro is $409,900, while the average sale price is $449,230, offering insights into the local housing market. On average, condos spend 74 days listed before being sold. Whether you're considering condominiums, apartments for sale, or modern condos, there are options to cater to different lifestyles. Browse the range of condos for sale in Millsboro, DE, and discover your ideal residence.

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