18

Millsboro, DE Condos for Sale

Section Image Section Image
  • 2303 Caitlins Way, Millsboro, DE 19966
    2303 Caitlins Way, Millsboro, DE 19966
    2303 Caitlins Way, Millsboro, DE 19966
    /29

    $220,000

    $7K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 730 Sq Ft

    2303 Caitlins Way, Millsboro, DE 19966

    Welcome to this charming 2-bedroom, 2-bathroom condo in the desirable Villages at Millwood community of Millsboro, Delaware. This well-designed home features an open floor plan that creates a spacious and inviting atmosphere, perfect for everyday living and entertaining. The light-filled kitchen opens seamlessly to the living area, where luxury vinyl plank flooring adds both style and durability.

    Agent Photo

    Dustin Oldfather

    Compass

    2303 Caitlins Way, 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

    $235,000

    $15K PRICE DROP
    • 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
  • 33571 Windswept Dr Unit 9101, Millsboro, DE 19966
    33571 Windswept Dr Unit 9101, Millsboro, DE 19966
    33571 Windswept Dr Unit 9101, Millsboro, DE 19966
    /73

    $340,000

    Open Sat 10AM - 1PM $19K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,677 Sq Ft

    33571 Windswept Dr Unit 9101, Millsboro, DE 19966

    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 extends the living space outdoors and invites quiet mornings or

    Valerie Ellenberger Compass

    33571 Windswept Dr Unit 9101, Millsboro, DE 19966
  • 3202 Caitlins Way, Millsboro, DE 19966
    3202 Caitlins Way, Millsboro, DE 19966
    3202 Caitlins Way, Millsboro, DE 19966
    /19

    $220,000

    $9K PRICE DROP
    • 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 including washer and dryer. Sliding glass doors leading to the screened porch and deck for relaxation on these summer evenings. The Villages at Millwood is ideally located near Millsboro's shopping, dining, and

    Tina Moore The Real Estate Market

    3202 Caitlins Way, Millsboro, DE 19966
  • 33571 Windswept Dr Unit 9302, Millsboro, DE 19966
    33571 Windswept Dr Unit 9302, Millsboro, DE 19966
    33571 Windswept Dr Unit 9302, Millsboro, DE 19966
    /104

    $490,000

    Open Sun 12PM - 2PM $5K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,823 Sq Ft

    33571 Windswept Dr Unit 9302, Millsboro, DE 19966

    NEW PRICE!! Welcome to 33571 Windswept Drive #9302, a beautifully appointed third-floor condominium in The Peninsula, offering 3 bedrooms, 3 full bathrooms, and spectacular views of the 6th hole fairway, tranquil ponds, and the Indian River Bay beyond. This spacious residence combines comfort, convenience, and coastal elegance within one of Delaware's premier gated resort communities. Step inside

    Brian Barrows Monument Sotheby's International Realty

    33571 Windswept Dr Unit 9302, 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

    • 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
  • 33559 Windswept Dr Unit 11102, Millsboro, DE 19966
    33559 Windswept Dr Unit 11102, Millsboro, DE 19966
    33559 Windswept Dr Unit 11102, Millsboro, DE 19966
    /85

    $429,900

    • 3 Beds
    • 3 Baths
    • 1,808 Sq Ft

    33559 Windswept Dr Unit 11102, Millsboro, DE 19966

    Welcome to Windswept at The Peninsula - Experience resort-style living in this beautifully maintained, turnkey ground-floor condo located in the sought-after Windswept neighborhood of The Peninsula. Perfectly positioned just a short stroll from the community's world-class amenities, you'll enjoy convenient access to the clubhouse, indoor and outdoor pools, spa, fitness center, tennis courts,

    Ian Blyth 360 PROPERTY SOLUTIONS

    33559 Windswept Dr Unit 11102, Millsboro, DE 19966
  • 1306 Caitlins Way, Millsboro, DE 19966
    1306 Caitlins Way, Millsboro, DE 19966
    1306 Caitlins Way, Millsboro, DE 19966
    /17

    $249,900

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    1306 Caitlins Way, Millsboro, DE 19966

    Welcome to Villages at Millwood! This well-maintained 3-bedroom, 2-bath condo features an open-concept floor plan with fresh paint and new carpet throughout. The bright and spacious living area offers sliding doors leading to a screened porch and open balcony—perfect for relaxing or enjoying the outdoors. The community amenities include a clubhouse and outdoor pool, and the convenient location

    Susan Mills JACK LINGO MILLSBORO

    1306 Caitlins Way, Millsboro, DE 19966
  • 5106 Caitlins Way, Millsboro, DE 19966
    5106 Caitlins Way, Millsboro, DE 19966
    5106 Caitlins Way, Millsboro, DE 19966
    /33

    $275,000

    $5K PRICE DROP
    • 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

    $232,900

    $7K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 900 Sq Ft

    5205 Caitlins Way, Millsboro, DE 19966

    Seller says bring offers, motivated to sell! 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,

    Amanda Sweigert Keller Williams Realty Delmarva

    5205 Caitlins Way, Millsboro, DE 19966
  • 2204 Caitlins Way Unit 2204, Millsboro, DE 19966
    2204 Caitlins Way Unit 2204, Millsboro, DE 19966
    2204 Caitlins Way Unit 2204, Millsboro, DE 19966
    /15

    $235,000

    • 2 Beds
    • 2 Baths
    • 714 Sq Ft

    2204 Caitlins Way Unit 2204, Millsboro, DE 19966

    Welcome to this charming 2-bedroom, 2 full-bathroom second-floor unit in the Villages at Millwood. Featuring a screened-in porch, this home offers the perfect spot to enjoy your morning coffee or unwind at the end of the day. Residents enjoy access to the community pool and the convenience of being just minutes from local restaurants, shopping, and Route 113. With Delaware's beaches, golf

    Rachel Cooper Berkshire Hathaway HomeServices PenFed Realty

    2204 Caitlins Way Unit 2204, Millsboro, DE 19966
  • 30868 Crepe Myrtle Dr Unit 4, Millsboro, DE 19966
    30868 Crepe Myrtle Dr Unit 4, Millsboro, DE 19966
    30868 Crepe Myrtle Dr Unit 4, Millsboro, DE 19966
    /37

    $325,000

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft

    30868 Crepe Myrtle Dr Unit 4, Millsboro, DE 19966

    Discover Peaceful Coastal Living in Gull Point – Waterfront Charm Without the Beach Crowds Escape to the hidden gem of Gull Point, a tranquil waterfront community where you can enjoy the best of Delaware's coastal lifestyle—without the traffic, congestion, or crowds. Here, every season offers its own unique charm. Summer is filled with days on the water, while fall and winter bring a quiet,

    Tammy Nichols RE/MAX Advantage Realty

    30868 Crepe Myrtle Dr Unit 4, 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

    SPECIAL INCENTIVE UNTIL END OF AUGUST: SELLER WILL ACCEPT $325,000 , AS IS .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

    Shirley Kalvinsky Jack Lingo - Rehoboth

    33584 Windswept Dr Unit 5401, 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

    $399,000

    $26K PRICE DROP
    • 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
  • 5306 Caitlins Way, Millsboro, DE 19966
    5306 Caitlins Way, Millsboro, DE 19966
    5306 Caitlins Way, Millsboro, DE 19966
    /27

    $260,000

    $15K PRICE DROP
    • 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
  • 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

    $19K PRICE DROP
    • 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
  • 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

    Open Sat 10AM - 2PM
    • 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
  • 33580 Windswept Dr Unit 4307, Millsboro, DE 19966
    33580 Windswept Dr Unit 4307, Millsboro, DE 19966
    33580 Windswept Dr Unit 4307, Millsboro, DE 19966
    /76

    $412,500

    Open Sat 10AM - 2PM
    • 3 Beds
    • 2 Baths
    • 1,860 Sq Ft

    33580 Windswept Dr Unit 4307, Millsboro, DE 19966

    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 This fully furnished and generously sized three-bedroom residence offers an exceptional setting overlooking the first fairway of the renowned Jack Nicklaus

    Paul Maltaghati Monument Sotheby's International Realty

    33580 Windswept Dr Unit 4307, Millsboro, DE 19966
Delaware Sussex County

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

Condo Prices in Millsboro, DE

The median price for condos in Millsboro is $325,000, and there are 18 condo listings available for sale.

Condo Price Trends

Median Condo Price
$325,000
Median 1-Bedroom Condo Price
$160,000
Median 2-Bedroom Condo Price
$299,000
Median 3-Bedroom Condo Price
$329,950
How to Buy a Home How to Finance a Home How to Sell a Home

In Millsboro, there are currently 18 condos for sale, providing a variety of options for potential buyers. With condos priced between $220,000 to $490,000, there's a range to accomodate every budget. As of July, 2026 the median home price in Millsboro is $413,990, while the average sale price is $443,167, offering insights into the local housing market. On average, condos spend 71 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.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group