South Dennis Massachusetts Real Estate & Homes For Sale

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$159,900
2bd
1ba
854sqft

310 Old Chatham Road # 9
South Dennis, Massachusetts 02660

Michael P Lotane
Today Real Estate
Old Chatham RV Resort- Want to spend summers on the Cape at an affordable price? This park model home has just been extensively renovated giving it an airy and comfortable feel, The annual fee has been paid and the place is fully and tastefully furnished. The kitchen and bathroom are brand new. Nothing for you to do here but come on down, load up with provisions, and then relax and enjoy.
$522,000
2bd
1ba
1102sqft
7,405Sqft

11 Leonard Road
South Dennis, Massachusetts 02660

Sandra L Schwenk
Steele Associates Real Estate
Terrific value on this long cherished year round home. And ... new septic and new furnace being installed. Hardwood floors, gas fireplace, formal dining with opening to living room, kitchen with breakfast nook leads to the heated (electric) sun room. There's a door to a spacious deck overlooking the lovely yard with 2 sheds, a fire pit, and outdoor shower.
$119,900
2bd
1ba
432sqft

310 Old Chatham Rd Road # A98
South Dennis, Massachusetts 02660

Carolyn Glynn
LAER Realty Partners
NEW Elevation Model 5 park home built in 2025 with warranties still in place! This home is located in the SEASONAL Old Chatham RV park open May 1 through October 31. This property is ideally nestled at the rear of the park on a quiet one-way street and sits on the largest corner lot available. Features two bedrooms and one and a half bathrooms, a full kitchen plus living and dining area.
$59,999
1bd
1ba
340sqft

310 Old Chatham Road # 12
South Dennis, Massachusetts 02660

Melanie Cauchon
Melanie Cauchon Real Estate
Dreaming of spending all summers on Cape Cod? Make it reality with this Like New Dutchmen Astoria 36' trailer sold w/all contents in Old Chatham Park (seasonal, NO YEAR-ROUND). Plenty of comfort & space: Central A/C , fireplace, Tall ceilings, huge kitchen with full size refrigerator & island, bathroom with double vanity and a bedroom with king size bed & laundry hook-up.
$699,900
3bd
2ba
1082sqft
12,632Sqft

10 Eastover
South Dennis, Massachusetts 02660

Ron Manzone
The Realty Cape Cod, LLC
Move-in ready ranch style home located in the desirable ''Olde Dennis on Bass River'' neighborhood. One-level living at its finest, this home features an updated kitchen with stainless steel appliances & granite countertops, gleaming hardwood floors, and an en-suite primary bedroom with a spacious, updated bath and walk-in shower.
$1,275,000
4bd
2ba
2179sqft
11,800Sqft

3 academy hill Lane
South Dennis, Massachusetts 02660

Mary Butler
ERA Cape Real Estate, LLC
Welcome to this beautifully crafted new construction Colonial, thoughtfully designed to complement the historic character of the Academy Hill neighborhood in South Dennis. This four-bedroom, two-and-a-half-bath home blends timeless New England style with modern comforts and quality craftsmanship.The inviting floor plan offers generous living spaces, ideal for both everyday living and entertaining.
$1,650,000
4bd
3ba
2132sqft
35,284Sqft

410 Main Street
South Dennis, Massachusetts 02660

Sandra Clarke
William Raveis Real Estate & Home Services
This sprawling Cape, an award winning circa 1780 home blends timeless character and modern luxury seamlessly. Recognized for its thoughtful preservation of history, this home reflects a level of craftmanship in every detail.
$349,900
2bd
1ba
1030sqft
182,952Sqft

432 Old Chatham Road APT 411
South Dennis, Massachusetts 02660

Kacy A DeFranco
Today Real Estate
Sensational Top-Floor 2-Bedroom Condominium in the Heart of DennisBeautifully situated in a centrally located and well-maintained community, this stunning top-floor 2-bedroom condo offers both comfort and convenience. Surrounded by lush, professionally landscaped grounds, the property provides a peaceful and inviting setting.
$869,000
3bd
3ba
2545sqft
16,553Sqft

10 Briarfield Road
South Dennis, Massachusetts 02660

Sofia T Naoom
Coastal Point Properties, LLC
Bright, spacious & well-maintained Colonial with peaks of Cape Cod Bay just 1.5 miles to Cold Storage Beach! This inviting 3 bedroom, 3 bathroom home offers an open kitchen/dining concept, two large living rooms perfect for entertaining, and a full bath are on the first floor. The second floor features 3 well appointed bedrooms with two full bathrooms.
$599,900
3bd
1ba
1144sqft
15,682Sqft

14 Benjamin Road
South Dennis, Massachusetts 02660

Patty M Flynn
William Raveis Real Estate & Home Services
Discover this charming and meticulously maintained 3 bedroom, 1.5 bath ranch offering 1,156 square feet of comfortable living space. Situated on a spacious lot on a cul-de-sac in a highly desirable South Dennis neighborhood, this property features a one-car attached garage and a lovely sunroom that overlooks the serene backyard.
$65,900
2bd
1ba
440sqft

310 Old Chatham Road # 29
South Dennis, Massachusetts 02660

Melanie Cauchon
Melanie Cauchon Real Estate
ZILLOW adds WRONG info-NO RENTALS allowed// Spacious 2017 Destination trailer on a Rarely available E rd lower priced site, backs up to the woods w/no one behind! One of the best sites Old Chatham seasonal resort offers & it comes with a big yard, new deck, a firepit & PVC shed! --PARK is OPEN May 1st-Oct.31st. NO YEAR ROUND USE. Pets allowed with restrictions.
$475,000
2bd
1ba
624sqft
8,712Sqft

36 Old Sailors Way
South Dennis, Massachusetts 02660

Amy Hohmann
Today Real Estate
Welcome to 36 Old Sailors Way! This adorable ranch style home offers the old Cape Cod Charm with 2 bedrooms and 1 bath. Kitchen/dining room combo with tile flooring, living room with a fireplace, stackable washing machine/dryer, outdoor shower, a shed for all your storage needs and a fenced in yard.
$72,900
3bd
1ba
727sqft

310 Old Chatham Road # 21
South Dennis, Massachusetts 02660

Melanie Cauchon
Melanie Cauchon Real Estate
Beware: ZILLOW adds WRONG info to listings-NO RENTALS allowed in this park. NO YEAR ROUND LIVING // 3-Bedroom seasonal home for sale in Old Chatham Resort, Dennis, Cape Cod. Set on a spacious Elite lot that backs up to the woods, it has a great yard & plenty of space on the stone parking area. Summer only: May 1st to Oct.
$925,000
3bd
2ba
2100sqft
20,473Sqft

1354 Route 134
South Dennis, Massachusetts 02660

Nancy Cassano
Today Real Estate
Completely renovated and thoughtfully updated, this South Dennis home with 2100 sq. ft. offers the perfect blend of coastal style and modern upgrades. The open-concept living area features a vaulted beamed ceiling, gas fireplace, and a stunning kitchen with quartz countertops, island seating, floating shelving, and stainless appliances.
$569,900
2bd
1ba
840sqft
7,841Sqft

16 Hazelwood Road
South Dennis, Massachusetts 02660

Shaun P Hannon
Cape Realty Inc
Charming Move-in Ready ranch in South Dennis.
$650,000
3bd
2ba
1164sqft
72,745Sqft

194 Main Street
South Dennis, Massachusetts 02660

The Team of Cape Cod
Seaport Village Realty
Don't miss this rare opportunity to own 1.67 acres in the Historic District of Dennis. Set on an expansive lot full of character and potential, this unique property invites its next owner to bring their vision to life. Featuring two outbuildings and additional bonus rooms, there's ample space to create, expand, or reimagine to suit your needs.
$9,500,000
5bd
4ba
5814sqft
222,592Sqft

299 Main Street
South Dennis, Massachusetts 02660

Tori Harrison Farr
Sotheby's International Realty, Inc.
A truly remarkable Bass River estate, set on an extraordinary 5.11 acres of private waterfront.This stunning property is the epitome of Cape Cod elegance, where timeless character meets thoughtful modern luxury.Lovingly restored to honor its original charm, the home has been impeccably updated throughout while preserving the architectural details that make it so special.
$45,000
2bd
1ba
312sqft

310 Old Chatham Road # C14
South Dennis, Massachusetts 02660

Kim L Terrio
William Raveis Real Estate & Home Services
Looking for an affordable Cape Cod getaway for summer? This absolutely pristine 2021 Destination RV at the Old Chatham Road RV Resort Park is perfect! Offering a primary bedroom with a king size bed and second bedroom with bunks and queen foldout bed, this trailer can handle a crowd.
$46,900
2bd
1ba
258sqft

310 Old Chatham Road # E47
South Dennis, Massachusetts 02660

Melanie Cauchon
Melanie Cauchon Real Estate
BEWARE: ZILLOW adds WRONG INFO info to our listings-There are NO RENTALS ALLOWED. NO YEAR ROUND LIVING in the park. OPEN May 1st-Oct.31st.//Spend all summers on Cape Cod in Dennis seasonal Old Chatham Resort! Pets ARE allowed w/restrictions.
$800,000
35,284Sqft

293 Main Street
South Dennis, Massachusetts 02660

Tori Harrison Farr
Sotheby's International Realty, Inc.
Discover the charm and potential of this .81-acre level lot nestled in the heart of South Dennis' historic district. Whether you envision building your dream home or creating a Cape Cod retreat, this prime location offers the perfect blend of history, character, and convenience. Buyer to conduct their own due diligence.
$2,000,000
50,094Sqft

295 Main Street
South Dennis, Massachusetts 02660

Tori Harrison Farr
Sotheby's International Realty, Inc.
A Rare Waterfront Offering on Bass River.An extraordinary opportunity awaits with this 1.15-acre waterfront estate lot on the coveted Bass River. Set amidst the charm of historic South Dennis, this property presents the perfect canvas to create a bespoke residence that captures the essence of Cape Cod living.
$125,000
570sqft

35 MA-134 # 9
South Dennis, Massachusetts 02660

John E Ciluzzi
Premier Commercial
Prime commercial condo available in a sought-after plaza on Route 134 in South Dennis. This 570 sq ft unit was formerly a law office and offers a flexible layout suitable for a variety of professional, retail, or medical uses. The space includes a private office, reception area, and restroom, with potential to reconfigure as needed.
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