Real Estate Investment Properties for Sale in Milford, CT

Looking for investment property in Milford, CT with high ROI ?

Explore a variety of short-term homes & houses in Milford, CT. Invest wisely with VRBO & Milford, CT Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Woodlawn Investment Property for Sale in Milford, CT

Search for Woodlawn Investment Property for Sale in Milford, Connecticut. Browse all of Mashvisor’s Woodlawn Investment Property listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 46 Woodlawn Investment Property listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
36 Kenwood Road Milford, CT Charming, expansive Cape, a mile from the beach!! . The solar panels will help with your e...	3 beds \| 2 baths \| 2,992 sq.ft.	$570,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 4.17% Airbnb Rental Income: $2760 Traditional Rental Income: $3768 Airbnb ROI: 1.05% Traditional ROI: 4.17%
1121 WINDWARD ROAD Milford, CT Invest with success and buy through Auction.com. This bank-owned investment property is a ...	2 beds \| 2 baths \| 1,473 sq.ft.	$392,000	Airbnb cash on cash: 0.48% Traditional cash on cash: 3.91% Airbnb Rental Income: $2062 Traditional Rental Income: $2791 Airbnb ROI: 0.48% Traditional ROI: 3.91%
35 Beachland Avenue Milford, CT This home truly has a designer's touch! Welcome to your custom home that's only 128 steps ...	3 beds \| 4 baths \| 3,000 sq.ft.	$1,195,000	Airbnb cash on cash: 0.15% Traditional cash on cash: 1.23% Airbnb Rental Income: $2760 Traditional Rental Income: $3314 Airbnb ROI: 0.15% Traditional ROI: 1.23%
253 Broadway Milford, CT Beach living in Wildemere Beach! Completely renovated 3-bedroom home, 2 full bathroom home...	3 beds \| 2 baths \| 1,504 sq.ft.	$779,999	Airbnb cash on cash: 0.72% Traditional cash on cash: 2.51% Airbnb Rental Income: $2760 Traditional Rental Income: $3412 Airbnb ROI: 0.72% Traditional ROI: 2.51%
50 Milford Point Road Milford, CT Experience panoramic water views from every room in this fully furnished coastal retreat, ...	3 beds \| 2 baths \| 1,728 sq.ft.	$975,500	Airbnb cash on cash: 0.08% Traditional cash on cash: 1.21% Airbnb Rental Income: $2760 Traditional Rental Income: $3135 Airbnb ROI: 0.08% Traditional ROI: 1.21%
22 Fairview Street Milford, CT ALL HIGHEST AND BEST OFFERS TO BE SUBMITTED BY WEDNESDAY 1/14/2026 at 5PM TO AGENTThis...	3 beds \| 2 baths \| 2,402 sq.ft.	$359,900	Airbnb cash on cash: 3.32% Traditional cash on cash: 6.52% Airbnb Rental Income: $2760 Traditional Rental Income: $3192 Airbnb ROI: 3.32% Traditional ROI: 6.52%
E Rutland Road Milford, CT Here's your chance to own a new home on a wonderful lot in North Milford, close to the gol...	4 beds \| 4 baths \| 3,200 sq.ft.	$949,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 2.6% Airbnb Rental Income: $3741 Traditional Rental Income: $5154 Airbnb ROI: 0.08% Traditional ROI: 2.6%
918 Wheelers Farms Road Milford, CT Magnificent horse farm set on over 6 acres of level, private land. Property features 28 st...	4 beds \| 3 baths \| 3,180 sq.ft.	$1,350,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 1.77% Airbnb Rental Income: $3741 Traditional Rental Income: $5240 Airbnb ROI: -0.07% Traditional ROI: 1.77%
7 Orland Street Milford, CT Don't miss this rare opportunity to live across from the water! Located in Bayview Beach A...	4 beds \| 1 baths \| 1,080 sq.ft.	$580,000	Airbnb cash on cash: 2.97% Traditional cash on cash: 3.06% Airbnb Rental Income: $3741 Traditional Rental Income: $2973 Airbnb ROI: 2.97% Traditional ROI: 3.06%
590 Gulf Street Milford, CT Perched high atop a scenic bluff, this extraordinary coastal retreat offers some of the mo...	5 beds \| 5 baths \| 4,430 sq.ft.	$2,499,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 2.19% Airbnb Rental Income: $4663 Traditional Rental Income: $9883 Airbnb ROI: -0.48% Traditional ROI: 2.19%
139 Rogers Avenue Milford, CT An exceptional coastal compound overlooking Milford Harbor, this one-of-a-kind waterfront ...	4 beds \| 6 baths \| 6,572 sq.ft.	$1,890,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 4.28% Airbnb Rental Income: $3741 Traditional Rental Income: $10996 Airbnb ROI: -0.32% Traditional ROI: 4.28%
18 Greenview Lane unit: 18 Milford, CT This unit is leased until 2026. Tenant occupied until August 1st 2026. Lease will convey t...	1 beds \| 1 baths \| 887 sq.ft.	$265,000	Airbnb cash on cash: 1.08% Traditional cash on cash: 4.78% Airbnb Rental Income: $1729 Traditional Rental Income: $2178 Airbnb ROI: 1.08% Traditional ROI: 4.78%
29 Meetinghouse Lane Milford, CT Great Neighborhood, Home does need some TLC but it offers Vinyl siding, Vinyl replacement ...	3 beds \| 2 baths \| 1,764 sq.ft.	$399,900	Airbnb cash on cash: 2.64% Traditional cash on cash: 7.15% Airbnb Rental Income: $2760 Traditional Rental Income: $3800 Airbnb ROI: 2.64% Traditional ROI: 7.15%
103 Ford Street Milford, CT Welcome to this spacious single-family home located in a desirable Milford neighborhood. T...	4 beds \| 1 baths \| 1,327 sq.ft.	$399,000	Airbnb cash on cash: 5.3% Traditional cash on cash: 5.81% Airbnb Rental Income: $3741 Traditional Rental Income: $3116 Airbnb ROI: 5.3% Traditional ROI: 5.81%
34 Snowapple Lane Milford, CT Ranch Style Living! A home with a view. This 3 bedroom, 1 bath ranch is situated above str...	3 beds \| 1 baths \| 2,016 sq.ft.	$398,000	Airbnb cash on cash: 2.93% Traditional cash on cash: 5.22% Airbnb Rental Income: $2760 Traditional Rental Income: $2965 Airbnb ROI: 2.93% Traditional ROI: 5.22%
146 High Street unit: Apt 303 Milford, CT This fully renovated One Bedroom Unit is in the beautiful Center Walk Association directly...	1 beds \| 1 baths \| 685 sq.ft.	$235,000	Airbnb cash on cash: 1.67% Traditional cash on cash: 5.39% Airbnb Rental Income: $1729 Traditional Rental Income: $2079 Airbnb ROI: 1.67% Traditional ROI: 5.39%
85 Viscount Drive unit: 13B Milford, CT Dreaming of Living By the Beach? Now is your chance to own this 3 bedroom coastal townhous...	3 beds \| 3 baths \| 1,340 sq.ft.	$450,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 3.66% Airbnb Rental Income: $2760 Traditional Rental Income: $3381 Airbnb ROI: 0.65% Traditional ROI: 3.66%
25 A Village Road Milford, CT Gorgeous New Construction Townhouse with Water Views f Award-Winning Woodmont Beach! Exper...	4 beds \| 3 baths \| 2,400 sq.ft.	$749,900	Airbnb cash on cash: 0.53% Traditional cash on cash: 3.57% Airbnb Rental Income: $3741 Traditional Rental Income: $5048 Airbnb ROI: 0.53% Traditional ROI: 3.57%
34 Orchard Road Milford, CT Discover exceptional coastal living in this beautifully rebuilt 4-bedroom Colonial located...	4 beds \| 3 baths \| 3,290 sq.ft.	$1,699,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 1.57% Airbnb Rental Income: $3741 Traditional Rental Income: $5379 Airbnb ROI: 0.02% Traditional ROI: 1.57%
134 McQuillan Drive Milford, CT 134 McQuillan Drive is a 56 Foot long Manufactured Home in the wonderful Ryder Woods Park ...	1 beds \| 1 baths \| 784 sq.ft.	$150,000	Airbnb cash on cash: 2.58% Traditional cash on cash: 9.51% Airbnb Rental Income: $1729 Traditional Rental Income: $2247 Airbnb ROI: 2.58% Traditional ROI: 9.51%
32-1/2 Village Road Milford, CT Unique living Multi unit Home walking distance to some of the best water front in Ct. Enjo...	4 beds \| 2 baths \| 2,076 sq.ft.	$829,900	Airbnb cash on cash: 1.47% Traditional cash on cash: 2.74% Airbnb Rental Income: $3741 Traditional Rental Income: $3906 Airbnb ROI: 1.47% Traditional ROI: 2.74%
96 W Main Street Milford, CT In-Town Two-Family \| Multiple Income Strategies \| Prime Walkable Location Well-located 193...	2 beds \| 2 baths \| 1,536 sq.ft.	$550,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 3.81% Airbnb Rental Income: $2062 Traditional Rental Income: $3258 Airbnb ROI: 0.45% Traditional ROI: 3.81%
6 Vernon Court Milford, CT Welcome to 6 Vernon Court, a rarely available Raised Ranch on a quiet cul-de-sac in Milfor...	3 beds \| 3 baths \| 1,092 sq.ft.	$499,000	Airbnb cash on cash: 1.84% Traditional cash on cash: 3.93% Airbnb Rental Income: $2760 Traditional Rental Income: $3085 Airbnb ROI: 1.84% Traditional ROI: 3.93%
3 Francis Street Milford, CT Meticulously maintained! Just move right in! Come and see this wonderfully accented proper...	3 beds \| 4 baths \| 3,034 sq.ft.	$1,695,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 1.02% Airbnb Rental Income: $2760 Traditional Rental Income: $4839 Airbnb ROI: -0.72% Traditional ROI: 1.02%
152 W River Street Milford, CT Embrace the timeless elegance and warmth of this home situated in the historic district of...	4 beds \| 5 baths \| 4,700 sq.ft.	$1,799,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 1.42% Airbnb Rental Income: $3741 Traditional Rental Income: $5930 Airbnb ROI: -0.38% Traditional ROI: 1.42%
65 Eastern Parkway Milford, CT Expanded 2 bedroom 1 bath Cape Cod style home in the Rivercliff area of Milford. Kitchen h...	2 beds \| 1 baths \| 1,308 sq.ft.	$425,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 2.93% Airbnb Rental Income: $2062 Traditional Rental Income: $2233 Airbnb ROI: 1.16% Traditional ROI: 2.93%
52 Stowe Avenue Milford, CT Live the coastal dream in this 3 bedroom home ideally located steps from the shoreline. Fe...	3 beds \| 2 baths \| 1,260 sq.ft.	$499,999	Airbnb cash on cash: 1.97% Traditional cash on cash: 3.83% Airbnb Rental Income: $2760 Traditional Rental Income: $2979 Airbnb ROI: 1.97% Traditional ROI: 3.83%
22 Lynmoor Street Milford, CT ALL HIGHEST & BEST OFFERS TO BE IN BY 5:00 TUESDAY 3/3. Thank you Looking for a fixer-up o...	4 beds \| 2 baths \| 2,126 sq.ft.	$375,000	Airbnb cash on cash: 4.8% Traditional cash on cash: 6.62% Airbnb Rental Income: $3741 Traditional Rental Income: $3570 Airbnb ROI: 4.8% Traditional ROI: 6.62%
36 Utica Street Milford, CT Expanded Ranch with Endless Potential on a Spacious Corner Lot! Opportunity awaits with th...	3 beds \| 1 baths \| 1,468 sq.ft.	$349,900	Airbnb cash on cash: 3.41% Traditional cash on cash: 5.15% Airbnb Rental Income: $2760 Traditional Rental Income: $2683 Airbnb ROI: 3.41% Traditional ROI: 5.15%
48 Winthrop Court Milford, CT Perfectly located near the beloved Duck Pond and vibrant downtown, this vintage 1928 colon...	4 beds \| 2 baths \| 2,081 sq.ft.	$650,000	Airbnb cash on cash: 2.26% Traditional cash on cash: 3.23% Airbnb Rental Income: $3741 Traditional Rental Income: $3515 Airbnb ROI: 2.26% Traditional ROI: 3.23%
213 Seaside Avenue Milford, CT Final & Best due by 12 Noon on Thursday, March 12th. Proudly family-owned and lovingly mai...	4 beds \| 3 baths \| 2,256 sq.ft.	$500,000	Airbnb cash on cash: 3.66% Traditional cash on cash: 5% Airbnb Rental Income: $3741 Traditional Rental Income: $3553 Airbnb ROI: 3.66% Traditional ROI: 5%
24 Matthews Street Milford, CT Beautifully Maintained Home with walk out lower level, possible in-law - Move-In Ready! St...	4 beds \| 3 baths \| 2,075 sq.ft.	$599,900	Airbnb cash on cash: 2.9% Traditional cash on cash: 4.46% Airbnb Rental Income: $3741 Traditional Rental Income: $3801 Airbnb ROI: 2.9% Traditional ROI: 4.46%

Your search for investment property begins and ends here

Woodlawn Investment Property for Sale in Milford, CT

36 Kenwood Road

Milford, CT

3 beds | 2 baths | 2,992 sq.ft.

$570,000

Airbnb cash on cash: 1.05%

Traditional cash on cash: 4.17%

Airbnb Rental Income: $2760

Traditional Rental Income: $3768

Airbnb ROI: 1.05%

Traditional ROI: 4.17%

1121 WINDWARD ROAD

Milford, CT

2 beds | 2 baths | 1,473 sq.ft.

$392,000

Airbnb cash on cash: 0.48%

Traditional cash on cash: 3.91%

Airbnb Rental Income: $2062

Traditional Rental Income: $2791

Airbnb ROI: 0.48%

Traditional ROI: 3.91%

35 Beachland Avenue

Milford, CT

3 beds | 4 baths | 3,000 sq.ft.

$1,195,000

Airbnb cash on cash: 0.15%

Traditional cash on cash: 1.23%

Airbnb Rental Income: $2760

Traditional Rental Income: $3314

Airbnb ROI: 0.15%

Traditional ROI: 1.23%

253 Broadway

Milford, CT

3 beds | 2 baths | 1,504 sq.ft.

$779,999

Airbnb cash on cash: 0.72%

Traditional cash on cash: 2.51%

Airbnb Rental Income: $2760

Traditional Rental Income: $3412

Airbnb ROI: 0.72%

Traditional ROI: 2.51%

50 Milford Point Road

Milford, CT

3 beds | 2 baths | 1,728 sq.ft.

$975,500

Airbnb cash on cash: 0.08%

Traditional cash on cash: 1.21%

Airbnb Rental Income: $2760

Traditional Rental Income: $3135

Airbnb ROI: 0.08%

Traditional ROI: 1.21%

22 Fairview Street

Milford, CT

3 beds | 2 baths | 2,402 sq.ft.

$359,900

Airbnb cash on cash: 3.32%

Traditional cash on cash: 6.52%

Airbnb Rental Income: $2760

Traditional Rental Income: $3192

Airbnb ROI: 3.32%

Traditional ROI: 6.52%

E Rutland Road

Milford, CT

4 beds | 4 baths | 3,200 sq.ft.

$949,000

Airbnb cash on cash: 0.08%

Traditional cash on cash: 2.6%

Airbnb Rental Income: $3741

Traditional Rental Income: $5154

Airbnb ROI: 0.08%

Traditional ROI: 2.6%

918 Wheelers Farms Road

Milford, CT

4 beds | 3 baths | 3,180 sq.ft.

$1,350,000

Airbnb cash on cash: -0.07%

Traditional cash on cash: 1.77%

Airbnb Rental Income: $3741

Traditional Rental Income: $5240

Airbnb ROI: -0.07%