37

The Peninsula Homes for Sale

Section Image Section Image
  • /39

    $799,900 New Construction

    • 4 - 5 Beds
    • 3 Baths
    • 2,572+ Sq Ft

    Frank Beach (3-car) Plan at Veranda at The Peninsula - The Peninsula, Millsboro, DE 19966

    This Frank model is a two-story 40-foot wide home that is designed to fit on narrower lots. The home features 4-5 bedrooms, 3 full baths, living room, kitchen, breakfast nook, laundry room, 3 car garage.

    Builder Photo

    Insight Homes

    Builder

    27506 S Nicklaus Ave Unit 36394417, Millsboro, DE 19966
  • /60

    $860,000

    • 5 Beds
    • 4.5 Baths
    • 3,400 Sq Ft

    27582 S Nicklaus Ave Unit 11, Millsboro, DE 19966

    Welcome to The Peninsula, coastal Delaware's premier resort-style country club community! Enjoy a panoramic, 180-degree tee-to-green sunrise views of the 2nd fairway from all three levels of this upscale home! Plenty of space for everyone here, with an open-space concept floor plan and 10-foot ceiling height on the main level, 5 bedrooms, 4 full baths upstairs. Morning sun illuminates the

    Sandi Bisgood Monument Sotheby's International Realty

    27582 S Nicklaus Ave Unit 11, Millsboro, DE 19966
  • /75

    $1,150,000 Open Sun 11:30AM - 1:30PM

    • 5 Beds
    • 3.5 Baths
    • 3,016 Sq Ft

    28042 Swallowtail Dr Unit 20, Millsboro, DE 19966

    Exquisite coastal-style home perfectly situated on a premium lot, backing to the prestigious Jack Nicklaus award-winning golf course. Nestled in the sought-after Peninsula community, this residence is a masterpiece of design, craftsmanship, and sophistication. This impeccably crafted Schell home built in 2021 offers an extended bump-out floor plan in the main living area and primary bedroom and

    Judith Dourgarian Northrop Realty

    28042 Swallowtail Dr Unit 20, Millsboro, DE 19966
  • /113

    $915,000

    • 5 Beds
    • 3.5 Baths
    • 3,000 Sq Ft

    27034 Firefly Blvd Unit 115, Millsboro, DE 19966

    Welcome to 27045 Firefly Boulevard, a beautifully appointed 5 bedroom, 3.5 bath home in Delaware’s premier resort community—The Peninsula on the Indian River Bay. Being offered fully furnished and nestled in the Marina Bay section, this elegant residence backs to a tranquil pond, offering peaceful views and year-round natural beauty.Curb appeal shines with HardiPlank shake siding,

    Krystal Casey Keller Williams Realty

    27034 Firefly Blvd Unit 115, Millsboro, DE 19966
  • /63

    $895,000

    • 4 Beds
    • 3.5 Baths
    • 3,501 Sq Ft

    27580 S Nicklaus Ave Unit 12, Millsboro, DE 19966

    Beautiful sunrises, bold sunsets and a 180 degree view of the 2nd fairway, from three levels, could be yours every day of the year! Check out the Video and take in the golf views and surrounding landscape! Step into a world of comfort and sophistication in this spacious 4-bedroom, 3.5-bath home, ideally situated in the serene Veranda neighborhood of the prestigious Peninsula on the Indian River

    Valerie Ellenberger Compass

    27580 S Nicklaus Ave Unit 12, Millsboro, DE 19966
  • /109

    $995,000

    • 5 Beds
    • 3.5 Baths
    • 3,500 Sq Ft

    27434 S Nicklaus Ave Unit 76, Millsboro, DE 19966

    ***SELLER WILL PAY ENTIRE TRANSFER TAX OF 4% ON AN ACCEPTABLE OFFER - A SAVINGS OF 2% OF PURCHASE PRICE FOR THE BUYER AT SETTLEMENT*** A fantastic buyer incentive for this well-appointed, move-in ready residence...Gracious living in this elegant home, nestled in the prestigious, thoughtfully planned country club community, the Peninsula. Come visit this Miller & Smith Hampton model,

    Zane Jones Jack Lingo - Rehoboth

    27434 S Nicklaus Ave Unit 76, Millsboro, DE 19966
  • /105

    $863,900 New Construction

    • 4 - 6 Beds
    • 3 - 4 Baths
    • 3,145+ Sq Ft

    Peterman II Beach Plan at Veranda at The Peninsula - The Peninsula, Millsboro, DE 19966

    Builder Photo

    Insight Homes

    Builder

    27506 S Nicklaus Ave Unit 36394415, Millsboro, DE 19966
  • /42

    $365,000

    • 2 Beds
    • 2.5 Baths
    • 1,441 Sq Ft

    27270 18th Blvd Unit 13304, Millsboro, DE 19966

    Welcome to this top-floor condo in the Peninsula, ( 2 bedrooms W/Den) where refined finishes and resort-style living come together in a premier coastal setting. Overlooking a peaceful pond with the Jack Nicklaus Signature Golf Course in the distance, this residence offers two spacious bedrooms, each with its own private bath and walk-in closet. One of the primary suites features an atrium door

    Jim Lattanzi Northrop Realty

    27270 18th Blvd Unit 13304, Millsboro, DE 19966
  • /136

    $2,750,000

    • 4 Beds
    • 3.5 Baths
    • 5,050 Sq Ft

    33530 Tiderunner Ave Unit 22, Millsboro, DE 19966

    An Elevated Coastal Sanctuary in The PeninsulaWelcome to 33530 Tiderunner Avenue, an Echelon-built masterpiece in the prestigious Sanctuary Enclave of The Peninsula on the Indian River Bay. This custom luxury home blends coastal sophistication, smart innovation, and sweeping waterfront panoramas, creating an ideal haven for the discerning buyer who values both beauty and function. Perched on

    Gary Desch Northrop Realty

    33530 Tiderunner Ave Unit 22, Millsboro, DE 19966
  • /110

    $775,000 Open Sun 11AM - 1PM

    • 4 Beds
    • 3.5 Baths
    • 3,075 Sq Ft

    27193 Barefoot Blvd Unit 23, Millsboro, DE 19966

    Looking for luxury at the beach? Welcome to “Splendor on the Green” , a beautifully appointed coastal villa perfectly positioned on a premium lot overlooking the 12th green of the Jack Nicklaus Signature Golf Course in the sought-after, gated Peninsula community.From the moment you step inside, you'll feel the harmony of elevated design and relaxed coastal living. Natural light pours

    Catina Fair Northrop Realty

    27193 Barefoot Blvd Unit 23, Millsboro, DE 19966
  • /122

    $1,450,000 Open Sun 2PM - 4PM

    • 4 Beds
    • 4.5 Baths
    • 3,651 Sq Ft

    33437 Islander Dr, Millsboro, DE 19966

    The welcoming covered entry of 33437 Islander Drive invites you inside to explore this exceptional luxury home, designed with enduring vision for resort-style living at home. Nestled in the sought-after, amenity-rich community of The Peninsula on Indian River Bay, this expanded Cassidy model balances coastal style, colonial design cues, and contemporary flair. Every room of this residence

    Judith Dourgarian Northrop Realty

    33437 Islander Dr, Millsboro, DE 19966
  • /34

    $435,000

    • 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! Don’t miss this opportunity to live at your ultimate getaway and experience the award-winning Peninsula Golf & Country Club. This bright, spacious, and elegant 3 bedroom condominium is being sold fully furnished and turnkey, ready for you to move in and immediately start enjoying the resort lifestyle. The home even comes with a

    Michael McKee Long & Foster Real Estate, Inc.

    33580 Windswept Dr Unit 4307, Millsboro, DE 19966
  • /57

    $835,000

    • 4 Beds
    • 3.5 Baths
    • 3,302 Sq Ft

    22095 S Preservation Dr Unit 132, Millsboro, DE 19966

    Nestled in a serene setting within the wooded Conservancy neighborhood of the Peninsula, this rarely available Southern-inspired floor plan offers an inviting blend of charm and sophistication. Wrapped in four spacious porches across two levels, the home celebrates its lush surroundings and creates a peaceful connection to the outdoors. Check out the Video!Step inside to discover a

    Valerie Ellenberger Compass

    22095 S Preservation Dr Unit 132, Millsboro, DE 19966
  • /118

    $1,450,000 Open Sun 1PM - 3PM

    • 4 Beds
    • 3.5 Baths
    • 3,500 Sq Ft

    27558 Medallion Ave, Millsboro, DE 19966

    Coastal Elegance Perfected in the Peninsula on Indian River BayTucked into one of the most sought-after coastal communities in Delaware, this exquisite residence in the Peninsula on the Indian River Bay offers a lifestyle as elevated as its design. With over 3,000 square feet of luxury living space, three bedrooms, three and a half baths, and sweeping pond views, this home seamlessly blends

    Judith Dourgarian Northrop Realty

    27558 Medallion Ave, Millsboro, DE 19966
  • /91

    $2,395,000

    • 6 Beds
    • 5.5 Baths
    • 5,400 Sq Ft

    33521 Tiderunner Ave, Millsboro, DE 19966

    Blending timeless coastal style, superior craftsmanship, and refined finishes, this custom Echelon Grand Cayman model stands among the most impressive residences in The Peninsula. With six bedrooms and five-and-a-half baths, the home commands sweeping Indian River Bay vistas from nearly every room, perfectly framed by the 7th hole of the Jack Nicklaus Signature Golf Course—a rare combination of

    Jim Lattanzi Northrop Realty

    33521 Tiderunner Ave, Millsboro, DE 19966
  • /70

    $330,000

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

    33584 Windswept Dr Unit 5205, Millsboro, DE 19966

    Watch the golf action of the 1st fairway! Enjoy this FURNISHED Sanibel floor plan with 2 bedrooms and two ensuite baths. Enjoy the spacious open living area, with adjacent dining area, upgraded kitchen cabinets and granite countertops, stainless appliances, crown molding, recessed lighting, ceiling fans, built-ins and a lovely gas fireplace that compliments this stylish home. Sip your morning

    Valerie Ellenberger Compass

    33584 Windswept Dr Unit 5205, Millsboro, DE 19966
  • /90

    $1,999,900

    • 5 Beds
    • 5.5 Baths
    • 5,720 Sq Ft

    33442 Marina Bay Cir, Millsboro, DE 19966

    Luxurious golf course living is yours in this stunning 5720 sq ft, 5-bedroom home in the gated, private country club community, The Peninsula on the Indian River Bay. Elegantly designed, expertly appointed, & beautifully maintained, this unique & rare custom designed Echelon home is nestled in a prime location & boasts unparalleled views of the #1 handicap,11th hole. Don't miss the VIDEO. Enjoy

    Valerie Ellenberger Compass

    33442 Marina Bay Cir, Millsboro, DE 19966
  • /117

    $1,675,000

    • 4 Beds
    • 3.5 Baths
    • 6,226 Sq Ft

    27283 18th Blvd, Millsboro, DE 19966

    Nestled on a premier lot in the sought after Peninsula Golf & Country Club, this exquisite Schell Shearwater expanded floor plan offers breathtaking views of the 18th fairway and Lingo Creek on the Indian River Bay. Watch the sunrise and moonrise while eagles and herons soar overhead—nature’s beauty at your doorstep.Step inside to a light-filled, open-concept design with luxury vinyl plank

    Valerie Ellenberger Compass

    27283 18th Blvd, Millsboro, DE 19966
  • /93

    $434,500

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

    33570 Windswept Dr Unit 3301, Millsboro, DE 19966

    Discover 33579 Windswept Drive, Unit 3301 — an impeccably renovated luxury condo in the exclusive, gated community of The Peninsula on the Indian River Bay. Perfectly positioned with breathtaking panoramic golf course and nature views, this residence delivers a sophisticated, turn-key living experience that feels like a five-star resort every day. Step inside and be greeted by a light-filled,

    Catina Fair Northrop Realty

    33570 Windswept Dr Unit 3301, Millsboro, DE 19966
  • /88

    $1,249,000

    • 4 Beds
    • 3.5 Baths
    • 3,600 Sq Ft

    24537 Wave Maker Dr, Millsboro, DE 19966

    Exceptional, custom-built home overlooking the Signature Jack Nicklaus golf course in Marina Bay within the Peninsula. Echelon Builders thoughtfully designed and integrated technology throughout this gracious residence with outdoor space on every level. Brazilian cherry floors and decorative moldings compliment the spacious interior. Manicured golf course views can be enjoyed from the open

    Randy Mason Jack Lingo - Rehoboth

    24537 Wave Maker Dr, Millsboro, DE 19966
  • /16

    $369,000

    • 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
  • /53

    $379,000

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

    33571 Windswept Dr Unit 9101, Millsboro, DE 19966

    NEW PRICE Best value on the market for a 3-bedroom ground-level unit in the Peninsula! Welcome to 33571 Windswept Drive, Unit 9101, the only Windsor Plan, ground floor unit that includes a third bedroom within the Windswept Condominium Development, and is located within the gated confines of the Peninsula, a coastal golf and country club community. Backing off onto the 6th Fairway of the Jack

    Jason Hoenen Bryan Realty Group

    33571 Windswept Dr Unit 9101, Millsboro, DE 19966
  • /71

    $459,900

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

    33564 Windswept Dr Unit 2301, Millsboro, DE 19966

    Presenting 33564 Windswept, an exceptional top-floor coastal condominium nestled within the prestigious community of The Peninsula on the Indian River! This impeccably maintained residence boasts a spacious and inviting layout, featuring three bedrooms and two-and-a-half baths. From its new hardwood floors to its exquisite architectural details, every inch of this end unit exudes sophistication

    Jim Lattanzi Northrop Realty

    33564 Windswept Dr Unit 2301, Millsboro, DE 19966
  • /9

    $425,000

    • Land
    • 0.28 Acre
    • $1,517,857 per Acre

    33526 Tiderunner Ave, Millsboro, DE 19966

    One of the few remaining lots in The Peninsula, this 0.28 Acre lot is available for your dream home! Located in The Peninsula, you will enjoy all that this 800 acre, gated, Jack Nicklaus Signature Golf community has to offer! Resort style amenities are in abundance and include a 30,000 square foot clubhouse, indoor and outdoor heated pools and hot tubs, poolside bar, restaurants, a sandy beach

    Jim Lattanzi Northrop Realty

    33526 Tiderunner Ave, Millsboro, DE 19966
  • /30

    $802,900 New Construction

    • 4 - 5 Beds
    • 3 - 3.5 Baths
    • 2,483+ Sq Ft

    Cartwright Beach Plan at Veranda at The Peninsula - The Peninsula, Millsboro, DE 19966

    A versatile single story plan featuring a spacious foyer, formal dining room, a cook's kitchen with large breakfast bar open to the breakfast nook and family room. Right off the breakfast nook, you will find an all season morning room flooded with natural light. This plan also includes a private owners retreat with dual walk in closets and spacious bath. Two additional bedrooms and another full

    Builder Photo

    Insight Homes

    Builder

    27506 S Nicklaus Ave Unit 36394420, Millsboro, DE 19966
  • /27

    $822,900 New Construction

    • 3 - 6 Beds
    • 2 - 4 Baths
    • 2,854+ Sq Ft

    Whatley Coastal Plan at Veranda at The Peninsula - The Peninsula, Millsboro, DE 19966

    This open concept, single story home features 3 bedrooms, including a spacious owner's suite with attached sitting room, en-suite bath and large walk-in closet. Entering the home, the large foyer leads you first to the formal dining room, which can be converted to a study, then to the large living room which opens to the over-sized kitchen, breakfast area and morning room... perfect for

    Builder Photo

    Insight Homes

    Builder

    27506 S Nicklaus Ave Unit 36394416, Millsboro, DE 19966
  • /58

    $837,900 New Construction

    • 3 - 6 Beds
    • 2 - 4 Baths
    • 2,947+ Sq Ft

    Whatley Beach Plan at Veranda at The Peninsula - The Peninsula, Millsboro, DE 19966

    This open concept, single story home features 3 bedrooms, including a spacious owner's suite with attached sitting room, en-suite bath and large walk-in closet. Entering the home, the large foyer leads you first to the formal dining room, which can be converted to a study, then to the large living room which opens to the over-sized kitchen, breakfast area and morning room... perfect for

    Builder Photo

    Insight Homes

    Builder

    27506 S Nicklaus Ave Unit 36394418, Millsboro, DE 19966
  • /22

    $724,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,358 Sq Ft

    Hadley To-Be-Built H Tbd, Millsboro, DE 19966

    Ask about the current builder incentives! Introducing Still Waters. The new neighborhood in the Peninsula. Basements are available. The Hadley is 3-6 bedrooms and 2.5 to 4.5 baths. 2,358 0 4,587 sq ft.. This floor plan has everything on the first floor, including an open great room, kitchen, and dining area. The Hadley offers numerous options, including additional bedrooms and bathrooms, living

    Paul Maltaghati Monument Sotheby's International Realty

    Hadley To-Be-Built H Tbd, Millsboro, DE 19966
  • /35

    $734,900 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,431 Sq Ft

    Lilac model To-Be-Bu Tbd, Millsboro, DE 19966

    Ask about the current builder incentives! The Lilac is a 4 - 6 bedroom, 2.5 -4.5 bath single-family home starting at 2,431 - 34,820 square feet. This floor plan has an open kitchen, dining area, and great room on the first floor, along with the owner's suite and flex room. The second floor has 3 bedrooms, a loft area, and an unfinished bonus room over the garage. Additional options are available

    Paul Maltaghati Monument Sotheby's International Realty

    Lilac model To-Be-Bu Tbd, Millsboro, DE 19966
  • /8

    $709,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,054 Sq Ft

    Iris To-Be-Built Hom Tbd, Millsboro, DE 19966

    Ask about the current builder incentives! Introducing Still Waters. The new neighborhood in the Peninsula. The Iris is a 3 -6 bedroom, 2.5 - 5.5 bath single-family home starting at 2,054 - 4,278 square feet. This floor plan has an open great room, kitchen, and dining area as well as an owner s suite and flex room on the first floor. The second floor includes a loft, unfinished storage, and two

    Paul Maltaghati Monument Sotheby's International Realty

    Iris To-Be-Built Hom Tbd, Millsboro, DE 19966
  • /24

    $654,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,567 Sq Ft

    Orchid To-Be-Built Tbd, Millsboro, DE 19966

    Ask about the current builder incentives! Introducing Still Waters neighborhood in the Peninsula. The Orchid is a 3 -4 bedroom, 2 -3 bath ranch home starting at 1,567 -3,250 square feet. This floor plan has everything on the first floor, including an open great room, kitchen, and dining area. Options are available to personalize this home, including a second floor, screened porch, sunroom, luxury

    Paul Maltaghati Monument Sotheby's International Realty

    Orchid To-Be-Built Tbd, Millsboro, DE 19966
  • /43

    $689,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,785 Sq Ft

    Bluebell To-Be-Built Tbd, Millsboro, DE 19966

    Ask about the current builder incentives that are available! Introducing the new Still Waters neighborhood in the Peninsula! Basements available. The Bluebell is a 3-6 bedroom, 2-4 bath ranch home starting at 1,785 -4,567 square feet. This floor plan has everything on the first floor, including an open great room, kitchen, and dining area. Options are available to personalize this home,

    Paul Maltaghati Monument Sotheby's International Realty

    Bluebell To-Be-Built Tbd, Millsboro, DE 19966

Why Live in The Peninsula

The Peninsula in Millsboro, Delaware, is a resort-style community developed on a peninsula along Indian River Bay. Established in 2002, it features an 18-hole Jack Nicklaus Signature golf course and a boardwalk hiking trail through a 225-acre nature preserve. Residents enjoy biking to pastel-painted, shingle-style clubhouses and a private beach lined with Cape American beach grass. The neighborhood is gated, offering a sense of exclusivity. Homes, built since 2003, include Craftsman-style houses, Federal-style dwellings, coastal traditional homes, Queen Anne-style townhouses, and condos in shades of blue, white, gray, yellow, and green. The area is safer than the national average, and the community is primarily full-time residents. The Peninsula offers numerous attractions, including a 33,000-square-foot clubhouse with dining options, a zero-entry wave pool, tennis and pickleball courts, and a fitness center. The Peninsula Nature Preserve provides boardwalk trails through tidal marshes, ideal for fishing and bird-watching. Nearby, Rehoboth Beach and Boardwalk are 15 miles northeast, though residents prefer the private beach for activities like fishing, kayaking, and crabbing. Local dining includes waterside restaurants like Serendipity and Paradise Grill, known for live music and seafood. Children attend highly rated Millsboro Middle School, and essential services like grocery stores and fast-food options are accessible via John J. Williams Highway. The closest hospital is Bayhealth Emergency and Urgent Care Center, 12 miles away, and Salisbury Regional Airport is 30 miles southwest.

Frequently Asked Questions

Is The Peninsula a good place to live?
The Peninsula is a good place to live. The Peninsula is considered very car-dependent and somewhat bikeable. The Peninsula has 5 parks for recreational activities. It is sparse in population with 2.5 people per acre and a median age of 62. The average household income is $85,967 which is below the national average. College graduates make up 30.6% of residents. A majority of residents in The Peninsula are home owners, with 12.2% of residents renting and 87.8% of residents owning their home. A local real estate agent serving The Peninsula can help you decide if this neighborhood is the right one for you. Learn more on our The Peninsula neighborhood guide.
How much do you need to make to afford a house in The Peninsula?
The median home price in The Peninsula is $845,000. If you put a 20% down payment of $169,000 and had a 30-year fixed mortgage with an interest rate of 6.56%, your estimated principal and interest payment would be $4,300 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $184K a year to afford the median home price in The Peninsula. The average household income in The Peninsula is $86K.
What are the best public schools in The Peninsula?
The best public schools that serve The Peninsula are:
What are the most popular zip codes in The Peninsula, Millsboro, DE?
The most popular zip codes in The Peninsula, Millsboro, DE include 19966, 19939, 19951, 19958 and 19970.
What are the most popular neighborhoods near The Peninsula, Millsboro, DE?
The most popular neighborhoods near The Peninsula, Millsboro, DE are Long Neck and Harbeson.

Home Trends in The Peninsula, DE

Housing Trends

Median Sale Price
$851,794
Median Single Family Sale Price
$941,613
Median Townhouse Sale Price
$528,750
Median 2 Bedroom Sale Price
$332,500
Average Price Per Sq Ft
$271
Number of Homes for Sale
31
Last 12 months Home Sales
96
Months of Supply
3.90
Median List Price
$845,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
10%
How to Buy a Home How to Finance a Home How to Sell a Home